MiMeDB: Showing metabocard for 17-Hydroxyprogesterone (MMDBc0047909)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:14:28 UTC

Update Date

2024-04-30 20:32:13 UTC

Metabolite ID

MMDBc0047909

Metabolite Identification

Common Name

17-Hydroxyprogesterone

Description

17-Hydroxyprogesterone also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. Formally it is a 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone. 17-Hydroxyprogesterone is found in all vertebrates. It is a chemical intermediate in the biosynthesis of many endogenous steroids, including androgens, estrogens, glucocorticoids, mineralocorticoids and neurosteroids. In particular, 17-Hydroxyprogesterone serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones. It is derived from progesterone via the enzyme known as 17-hydroxylase, a cytochrome P450 enzyme also known as CYP17A1. It can also be biosynthesized from 17-hydroxypregnenolone via the enzyme 3beta-hydroxysteroid dehydrogenase/delta5-4 isomerase (PMID: 1955079 ). 17-OHP is an agonist of the progesterone receptor (PR). It is also an antagonist of the mineralocorticoid receptor (MR) as well as a partial agonist of the glucocorticoid receptor (GR). 17-Hydroxyprogesterone is a natural progestin and in pregnancy it increases in the third trimester primarily due to fetal adrenal production. 17-Hydroxyprogesterone is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to ovulation, and 35-290 ng/dl during the luteal phase. Measurements of levels of 17-hydroxyprogesterone are useful in the evaluation of patients with suspected congenital adrenal hyperplasia as the typical enzymes that are defective, namely 21-hydroxylase, lead to a build-up of 17-OHP. 17-OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but not 17-OHP is also contributed by the placenta.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

17-Hydroxyprogesterone.mol
  Mrv1652305261923522D          

 27 30  0  0  0  0            999 V2000
   -1.8185   -0.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0393   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8240   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    0.7797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5717    1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0393    0.5248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0393    1.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1041   -0.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1041    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884    1.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.1123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0393   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 13 24  1  6  0  0  0
 21 25  1  6  0  0  0
  9 26  1  1  0  0  0
 10 27  1  6  0  0  0
M  END

HMDB0000374
     RDKit          3D
17-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.9720   -0.9828    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846   -1.0946   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.9423   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758   -0.2365   -0.7900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7515   -0.4888   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4507    1.2496   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    1.9005   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.7532   -0.6698 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2188    0.9180   -0.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9390    2.0000   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384    2.2767   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    1.0106   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3306    1.1015   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -0.0866   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785   -0.0314    0.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212   -1.3908   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805   -1.2421   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069   -0.3198    0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6521   -0.8555    1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -0.3761   -0.3318 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2163   -1.4788    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.6138   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9298   -0.3419    0.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1562    0.0498    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950   -1.0724    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650    0.0122    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -1.8333    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692    0.0719   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9467    1.6225   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630    1.4812    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    2.5670   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    2.4630    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.4456   -1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    1.1641    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    1.5393   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    2.8947   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    3.0794   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    2.5885    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009    2.0675   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921   -1.7421   -1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378   -2.0862    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -2.2217   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.7457   -1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -0.5539    1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -0.4327    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.9538    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.5886   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -2.4524    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -1.1923    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -1.8965   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6798   -2.4036    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7340    0.9886    1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    0.1626    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7073   -0.7509    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

17-Hydroxyprogesterone.mol
  Mrv1652305261923522D          

 27 30  0  0  0  0            999 V2000
   -1.8185   -0.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0393   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8240   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    0.7797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5717    1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0393    0.5248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0393    1.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1041   -0.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1041    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884    1.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.1123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0393   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 13 24  1  6  0  0  0
 21 25  1  6  0  0  0
  9 26  1  1  0  0  0
 10 27  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047909

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

> <INCHI_KEY>
DBPWSSGDRRHUNT-CEGNMAFCSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.4611

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.895190581319426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.4011792776666674

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.598886675440433

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.699646444874293

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8049652826185154

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
94.10529999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000374
     RDKit          3D
17-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.9720   -0.9828    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846   -1.0946   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.9423   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758   -0.2365   -0.7900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7515   -0.4888   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4507    1.2496   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    1.9005   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.7532   -0.6698 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2188    0.9180   -0.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9390    2.0000   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384    2.2767   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    1.0106   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3306    1.1015   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -0.0866   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785   -0.0314    0.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212   -1.3908   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805   -1.2421   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069   -0.3198    0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6521   -0.8555    1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -0.3761   -0.3318 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2163   -1.4788    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.6138   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9298   -0.3419    0.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1562    0.0498    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950   -1.0724    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650    0.0122    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -1.8333    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692    0.0719   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9467    1.6225   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630    1.4812    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    2.5670   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    2.4630    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.4456   -1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    1.1641    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    1.5393   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    2.8947   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    3.0794   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    2.5885    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009    2.0675   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921   -1.7421   -1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378   -2.0862    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -2.2217   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.7457   -1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -0.5539    1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -0.4327    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.9538    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.5886   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -2.4524    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -1.1923    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -1.8965   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6798   -2.4036    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7340    0.9886    1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    0.1626    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7073   -0.7509    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 17-Hydroxyprogesterone.mol                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.395  -0.560   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.728  -1.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.728  -2.870   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.062  -3.640   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.395  -3.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.061  -2.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.727  -3.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.606  -2.870   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.606  -1.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.940  -0.560   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.405  -1.036   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.310   0.210   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.405   1.455   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.801   2.106   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.062   1.223   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.935   3.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.940   0.980   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.940   2.520   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.606   1.750   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.727   0.980   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.727  -0.560   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.061  -1.330   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.061   0.210   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.778   2.862   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      -0.727  -2.100   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.606   0.210   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.940  -2.100   0.000  0.00  0.00           H+0
CONECT    1    2   22                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21   26                                             
CONECT   10    9   11   17   27                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17   24                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    9   22   25                                             
CONECT   22   21    1    6   23                                             
CONECT   23   22                                                            
CONECT   24   13                                                            
CONECT   25   21                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0000374
HETATM    1  C1  UNL     1      -4.972  -0.983   0.875  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.285  -1.095  -0.423  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.672  -1.942  -1.210  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.176  -0.236  -0.790  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.751  -0.489  -2.123  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.451   1.250  -0.717  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.074   1.901  -0.521  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.124   0.753  -0.670  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.219   0.918  -0.068  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.939   2.000  -0.875  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.238   2.277  -0.120  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.011   1.011  -0.059  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.331   1.101  -0.096  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.193  -0.087  -0.043  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.379  -0.031   0.325  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.621  -1.391  -0.443  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.180  -1.242  -0.887  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.407  -0.320   0.038  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.652  -0.855   1.456  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.966  -0.376  -0.332  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.216  -1.479   0.395  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.191  -1.614  -0.116  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.930  -0.342   0.067  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.156   0.050   1.486  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.095  -1.072   0.693  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.865   0.012   1.327  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.757  -1.833   1.557  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.269   0.072  -2.740  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.947   1.622  -1.638  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.063   1.481   0.172  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.925   2.567  -1.398  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.996   2.463   0.406  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.039   0.446  -1.710  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.221   1.164   1.004  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.158   1.539  -1.861  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.318   2.895  -0.927  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.753   3.079  -0.643  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.961   2.588   0.894  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.801   2.068  -0.168  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.192  -1.742  -1.339  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.738  -2.086   0.394  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.713  -2.222  -1.009  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.209  -0.746  -1.884  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.650  -0.554   1.820  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.919  -0.433   2.170  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.530  -1.954   1.474  1.00  0.00           H  
HETATM   47  H23 UNL     1       0.839  -0.589  -1.422  1.00  0.00           H  
HETATM   48  H24 UNL     1       0.777  -2.452   0.286  1.00  0.00           H  
HETATM   49  H25 UNL     1       0.165  -1.192   1.461  1.00  0.00           H  
HETATM   50  H26 UNL     1      -1.233  -1.897  -1.187  1.00  0.00           H  
HETATM   51  H27 UNL     1      -1.680  -2.404   0.521  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.734   0.989   1.597  1.00  0.00           H  
HETATM   53  H29 UNL     1      -1.204   0.163   2.060  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.707  -0.751   2.014  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5    6   23
CONECT    5   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   23   33
CONECT    9   10   20   34
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   13   18
CONECT   13   14   39
CONECT   14   15   15   16
CONECT   16   17   40   41
CONECT   17   18   42   43
CONECT   18   19   20
CONECT   19   44   45   46
CONECT   20   21   47
CONECT   21   22   48   49
CONECT   22   23   50   51
CONECT   23   24
CONECT   24   52   53   54
END

HMDB0000374
     RDKit          3D
17-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.9720   -0.9828    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846   -1.0946   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.9423   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758   -0.2365   -0.7900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7515   -0.4888   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4507    1.2496   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    1.9005   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.7532   -0.6698 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2188    0.9180   -0.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9390    2.0000   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384    2.2767   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    1.0106   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3306    1.1015   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -0.0866   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785   -0.0314    0.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212   -1.3908   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805   -1.2421   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069   -0.3198    0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6521   -0.8555    1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -0.3761   -0.3318 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2163   -1.4788    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.6138   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9298   -0.3419    0.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1562    0.0498    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950   -1.0724    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650    0.0122    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -1.8333    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692    0.0719   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9467    1.6225   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630    1.4812    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    2.5670   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    2.4630    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.4456   -1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    1.1641    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    1.5393   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    2.8947   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    3.0794   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    2.5885    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009    2.0675   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921   -1.7421   -1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378   -2.0862    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -2.2217   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.7457   -1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -0.5539    1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -0.4327    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.9538    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.5886   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -2.4524    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -1.1923    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -1.8965   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6798   -2.4036    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7340    0.9886    1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    0.1626    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7073   -0.7509    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

Synonyms

Value	Source
17-Hydroxypregn-4-en-3,20-dione	ChEBI
17alpha-Hydroxy-4-pregnene-3,20-dione	ChEBI
17alpha-Hydroxy-progesterone	ChEBI
delta(4)-Pregnene-17alpha-ol-3,20-dione	ChEBI
Hidroxiprogesterona	ChEBI
Hydroxyprogesterone	ChEBI
Hydroxyprogesteronum	ChEBI
Pregn-4-ene-3,20-dione-17-ol	ChEBI
17a-Hydroxy-4-pregnene-3,20-dione	Generator
17Α-hydroxy-4-pregnene-3,20-dione	Generator
17a-Hydroxy-progesterone	Generator
17Α-hydroxy-progesterone	Generator
delta(4)-Pregnene-17a-ol-3,20-dione	Generator
Δ(4)-pregnene-17α-ol-3,20-dione	Generator
Δ(4)-pregnene-17a-ol-3,20-dione	HMDB
17-alpha-Hydroxyprogesterone	HMDB
17-Hydroxypregn-4-ene-3,20-dione	HMDB
17-OH Progesterone	HMDB
17-OHP	HMDB
17a-Hydroxypregn-4-ene-3,20-dione	HMDB
17a-Hydroxyprogesterone	HMDB
17alpha-Hydroxyprogesterone	HMDB
D4-Pregnen-17a-ol-3,20-dione	HMDB
Gestageno	HMDB
Gestageno gador	HMDB
Pregn-4-en-17a-ol-3,20-dione	HMDB
Prodix	HMDB
Prodox	HMDB
17 Hydroxyprogesterone	HMDB
17-Hydroxyprogesterone, (17 alpha)-isomer	HMDB
17 alpha Hydroxyprogesterone	HMDB
17 alpha-Hydroxyprogesterone	HMDB
17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomer	HMDB

Molecular Formula

C₂₁H₃₀O₃

Average Mass

330.4611

Monoisotopic Mass

330.219494826

IUPAC Name

(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

68-96-2

SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

DBPWSSGDRRHUNT-CEGNMAFCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:17252 )
Progestagens (C01176 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030161 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	2.99	ALOGPS
logP	3.4	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.11 m³·mol⁻¹	ChemAxon
Polarizability	37.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)	splash10-004l-4911000000-d40ba45835d1ee1b6c41	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002o-9651000000-b44110f9abcffa42ce35	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-4911000000-d40ba45835d1ee1b6c41	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k9f-4595000000-89ccbf45dbf9f474bd2f	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-007c-3249000000-3570f5d248c0ee0716ee	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0009000000-a157e4b4aa18bdbc2531	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-5900000000-42494c0ef4b45cfa5cf4	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9700000000-d8a942a3dfdb061bd5c3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-002o-9651000000-b0c55e50343bf8ab3077	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4j-4930000000-c5056c0aac78a148ea92	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-052b-5910000000-fcf792a46552ed6e0028	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-052b-6900000000-6970a665800f041e9612	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0532-6966000000-f57233040f10efef4ba9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0009000000-0cff8a9a4549636b3f42	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0a4j-9800000000-3aaefadc8d2e4ad3a522	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0a6s-9600000000-17d56b65d46a46d9f653	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0029000000-0af1b9a61aa5a9d514a4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0lzi-0295000000-0510776f8fa0d9ddcb6a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00li-3970000000-1655d52be304b45389ae	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-bc250df2e599669d113e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-0097000000-41db31593b4f58cd4bc4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-0092000000-464375e5c4a93d5d20b3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0019000000-bf0f51dc62b5855371a3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0922000000-6997f50bd7502e7518f2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0cdi-3910000000-051d81ed4aaf877bebaf	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0039000000-8b733a2d2a661578ddbe	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-0049000000-1387b7ed039fc5504c87	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-0091000000-dc494a2f8f424f99a574	2021-09-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9731000000-48d2266d41955ffa9ce4	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Blood
Feces
Saliva
Testis
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192053	Aldo-keto reductase family 1 member C1	Unknown	Q04828	Homo sapiens
MMDBp0192107	Cytochrome P450 11B1, mitochondrial	Unknown	P15538	Homo sapiens
MMDBp0192653	Steroid 17-alpha-hydroxylase/17,20 lyase	Unknown	P05093	Homo sapiens
MMDBp0193970	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1	Unknown	P14060	Homo sapiens
MMDBp0193971	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2	Unknown	P26439	Homo sapiens
MMDBp0193997	Cytochrome P450 11B2, mitochondrial	Unknown	P19099	Homo sapiens
MMDBp0195936	Cytochrome P450, family 21, subfamily A, polypeptide 2	Enzyme	Q08AG9	Homo sapiens
MMDBp0196723	Steroid 21-hydroxylase	Unknown	P08686

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001478	17a-Hydroxypregnenolone	17-Hydroxyprogesterone	Not Available	3 Beta-Hydroxysteroid Dehydrogenase/Delta 5->4-Isomerase Type I	VMH	12205101
MMDBr0001479	17a-Hydroxypregnenolone	17-Hydroxyprogesterone	Hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2	3 Beta-Hydroxysteroid Dehydrogenase/Delta 5->4-Isomerase Type I	VMH	12205101
MMDBr0001846	Hydrogen Ion	17-Hydroxyprogesterone	Cytochrome p450, family 17, subfamily a, polypeptide 1	Cytochrome P450 17A1	VMH	7893148
MMDBr0001850	17-Hydroxyprogesterone	Cortexolone	Cytochrome p450, family 21, subfamily a, polypeptide 2	Steroid 21-Hydroxylase	VMH	16541276 18381579 18381580
MMDBr0008858	17-Hydroxyprogesterone	17-Hydroxyprogesterone	Atp binding cassette subfamily b member 1	Transport of 17Alpha-Hydroxyprogesterone, Extracellular	VMH	30371894
MMDBr0009624	Hydrogen Ion	17-Hydroxyprogesterone	Cytochrome p450, family 17, subfamily a, polypeptide 1	Steroid 17Alpha-Monooxygenase	VMH	30371894
MMDBr0009626	pregn-5-ene-3,20-dione-17-ol	17-Hydroxyprogesterone	Hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	Steroid Delta-Isomerase	VMH	30371894
MMDBr0009627	17-Hydroxyprogesterone	Cortexolone	Cytochrome p450, family 21, subfamily a, polypeptide 2	Steroid 21-Monooxygenase	VMH	30371894
MMDBr0009628	17-Hydroxyprogesterone	Water	Cytochrome p450, family 11, subfamily b, polypeptide 1	Steroid, Reduced-Adrenal-Ferredoxin:Oxygen Oxidoreductase (11-Hydroxylating)	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
11-beta-hydroxylase deficiency	Slight Increase	Association	Human Blood	HMDB	8933406
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	11038205
21-hydroxylase deficiency		Association	Human Blood	HMDB	26336836
21-hydroxylase deficiency		Association	Human Blood	HMDB	10857554
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	11826238
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	25850025
Phenylketonuria	Slight Increase	Association	Human Blood	HMDB	17574536
Rheumatoid arthritis	Decreased	Association	Human Urine	HMDB	15249323
21-hydroxylase deficiency	Slight Decrease	Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
21-hydroxylase deficiency	Increased	Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified			0.00130	0.0591	uM	Children (1-13 years old)	Both	11-beta-hydroxylase deficiency	HMDB	8933406
Human Blood	Detected and Quantified			0.216	0.265	uM	Newborn (0-30 days old)	Female	11-beta-hydroxylase deficiency	HMDB	8933406
Human Blood	Detected and Quantified	6.99				uM	Newborn (0-30 days old)	Female	21-hydroxylase deficiency	HMDB	11038205
Human Blood	Detected and Quantified	484.17				uM	Adolescent (13-18 years old)	Female	21-hydroxylase deficiency	HMDB	11038205
Human Blood	Detected and Quantified	<0.00300				uM	Newborn (0-30 days old)	Not Specified	21-hydroxylase deficiency	HMDB	26336836
Human Blood	Detected and Quantified	>0.300				uM	Newborn (0-30 days old)	Not Specified	21-hydroxylase deficiency	HMDB	26336836
Human Blood	Detected and Quantified	>0.303				uM	Children (1-13 years old)	Male	21-hydroxylase deficiency	HMDB	10857554
Human Blood	Detected and Quantified	>0.605				uM	Newborn (0-30 days old)	Male	21-hydroxylase deficiency	HMDB	10857554
Human Blood	Detected and Quantified			0.0388	0.252	uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	HMDB	11826238
Human Blood	Detected and Quantified	0.238		0.0251	0.611	uM	Adult (>18 years old)	Both	21-hydroxylase deficiency	HMDB	25850025
Human Blood	Detected and Quantified			3873.39	12951.64	uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	HMDB	11038205
Human Blood	Detected and Quantified	0.000908				uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	7951484
Human Blood	Detected and Quantified	0.0057				uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.009				uM	Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00170	0.00190			uM	Children (1-13 years old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00178	0.00144			uM	Infant (0-1 year old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00189	0.00100			uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00240	0.00220			uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00294	0.000900			uM	Newborn (0-30 days old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.00330	0.00180			uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.00450	0.184	uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.00740	0.296	uM	Newborn (0-30 days old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified			0.0832	0.339	uM	Newborn (0-30 days old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	27476613
Human Blood	Detected and Quantified	<0.000605				uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	HMDB	18182448
Human Blood	Detected and Quantified			0.0147	0.0420	uM	Infant (0-1 year old)	Both	Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis	HMDB	16439592
Human Blood	Detected and Quantified	0.0032				uM	Newborn (0-30 days old)	Female	Bartter Syndrome, Type 2, Antenatal	HMDB	26069767
Human Blood	Detected and Quantified	1.522				uM	Infant (0-1 year old)	Both	Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency (CAH)	HMDB	19390483
Human Blood	Detected and Quantified	<0.000450				uM	Adult (>18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	<0.000450				uM	Infant (0-1 year old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	<0.000450				uM	Adolescent (13-18 years old)	Female	Lipoid Adrenal Hyperplasia	HMDB	9077535
Human Blood	Detected and Quantified	0.152		0.0022	0.302	uM	Adult (>18 years old)	Both	Phenylketonuria	HMDB	17574536
Human Urine	Detected and Quantified	0.00065	0.00011			umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323
Human Urine	Detected and Quantified	0.00077	0.0002			umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	HMDB	15249323
Human Urine	Detected and Quantified	<0.00015				umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	23159298
Human Blood	Detected and Quantified	<0.00250				uM	Children (1-13 years old)	Both	Normal	HMDB	26336836
Human Blood	Detected and Quantified	<0.00500				uM	Not Specified	Both	Normal	HMDB	8933406
Human Blood	Detected and Quantified	<0.00600				uM	Adult (>18 years old)	Male	Normal	HMDB	26336836
Human Blood	Detected and Quantified	<0.0121				uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	19390483
Human Blood	Detected and Quantified	<0.0450				uM	Newborn (0-30 days old)	Both	Normal	HMDB	8933406
Human Saliva	Detected and Quantified	<1.00				uM	Adult (>18 years old)	Both	Normal	HMDB	16155259
Human Blood	Detected and Quantified			0.000212	0.00233	uM	Newborn (0-30 days old)	Female	Normal	HMDB	18182448
Human Blood	Detected and Quantified			0.000300	0.00510	uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	16439592
Human Blood	Detected and Quantified			0.000500	0.0200	uM	Not Specified	Not Specified	Normal	HMDB	26069767
Human Urine	Detected and Quantified	0.0011		0	0.0019	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	23159298
Human Urine	Detected and Quantified	0.0013	0.00026			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15249323
Human Blood	Detected and Quantified	0.00151	0.000303			uM	Adult (>18 years old)	Female	Normal	HMDB	7951484
Human Blood	Detected and Quantified	0.00357		0.00109	0.00539	uM	Adult (>18 years old)	Both	Normal	HMDB	25850025
Human Blood	Detected and Quantified	0.00454	0.00363			uM	Adult (>18 years old)	Female	Normal	HMDB	11826238
Human Blood	Detected and Quantified	0.011		0.0003	0.023	uM	Infant (0-1 year old)	Both	Normal	HMDB	7776113
Human Blood	Detected and Quantified	0.0014		0.000030	0.0028	uM	Adult (>18 years old)	Both	21-hydroxylase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	0.016		0.0090	0.024	uM	Children (1-13 years old)	Both	21-Hydroxylase Deficiency (CYP21)	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified			0.000300	0.00950	uM	Children (1 - 13 years old)	Both	Normal	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Blood	Detected and Quantified			0.00061	0.00700	uM	Adult (>18 years old)	Male	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Blood	Detected and Quantified			0.00061	0.0136	uM	Adult (>18 years old)	Female	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal cortex	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000374

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021992

KNApSAcK ID

Not Available

Chemspider ID

6002

KEGG Compound ID

C01176

BioCyc ID

17-ALPHA-HYDROXYPROGESTERONE

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17252

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hampl R, Lachman M, Novak Z, Sulcova J, Starka L: Serum levels of steroid hormones in men with varicocele and oligospermia as compared to normozoospermic men. Exp Clin Endocrinol. 1992;100(3):117-9. doi: 10.1055/s-0029-1211189. [PubMed:1305061 ]
Lorence MC, Naville D, Graham-Lorence SE, Mack SO, Murry BA, Trant JM, Mason JI: 3 beta-hydroxysteroid dehydrogenase/delta 5----4-isomerase expression in rat and characterization of the testis isoform. Mol Cell Endocrinol. 1991 Sep;80(1-3):21-31. doi: 10.1016/0303-7207(91)90139-j. [PubMed:1955079 ]
Toscano V, Sancesario G, Bianchi P, Cicardi C, Casilli D, Giacomini P: Cerebrospinal fluid estrone in pseudotumor cerebri: a change in cerebral steroid hormone metabolism? J Endocrinol Invest. 1991 Feb;14(2):81-6. doi: 10.1007/BF03350271. [PubMed:2061573 ]
Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. doi: 10.1172/JCI114325. [PubMed:2808702 ]
Wilson SC, Hodgins MB, Scott JS: Incomplete masculinization due to a deficiency of 17 beta-hydroxysteroid dehydrogenase: comparison of prepubertal and peripubertal siblings. Clin Endocrinol (Oxf). 1987 Apr;26(4):459-69. doi: 10.1111/j.1365-2265.1987.tb00803.x. [PubMed:2820622 ]
al Saedi S, Dean H, Dent W, Cronin C: Reference ranges for serum cortisol and 17-hydroxyprogesterone levels in preterm infants. J Pediatr. 1995 Jun;126(6):985-7. doi: 10.1016/s0022-3476(95)70229-6. [PubMed:7776113 ]
Katagiri M, Kagawa N, Waterman MR: The role of cytochrome b5 in the biosynthesis of androgens by human P450c17. Arch Biochem Biophys. 1995 Mar 10;317(2):343-7. doi: 10.1006/abbi.1995.1173. [PubMed:7893148 ]
White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. doi: 10.1002/humu.1380030408. [PubMed:8081391 ]
Sahin Y, Kelestimur F: 17-Hydroxyprogesterone responses to gonadotrophin-releasing hormone agonist buserelin and adrenocorticotrophin in polycystic ovary syndrome: investigation of adrenal and ovarian cytochrome P450c17alpha dysregulation. Hum Reprod. 1997 May;12(5):910-3. doi: 10.1093/humrep/12.5.910. [PubMed:9194638 ]
Kirchengast S, Hartmann B, Huber J: Serum levels of sex hormones, thyroid hormones, growth hormone, IGF I, and cortisol and their relations to body fat distribution in healthy women dependent on their menopausal status. Z Morphol Anthropol. 1996 Sep;81(2):223-34. [PubMed:9270338 ]
Ibanez L, de Zegher F, Potau N: Anovulation after precocious pubarche: early markers and time course in adolescence. J Clin Endocrinol Metab. 1999 Aug;84(8):2691-5. doi: 10.1210/jcem.84.8.5883. [PubMed:10443661 ]
Escobar-Morreale HF, San Millan JL, Smith RR, Sancho J, Witchel SF: The presence of the 21-hydroxylase deficiency carrier status in hirsute women: phenotype-genotype correlations. Fertil Steril. 1999 Oct;72(4):629-38. doi: 10.1016/s0015-0282(99)00317-9. [PubMed:10521100 ]
Bolt RJ, Van Weissenbruch MM, Popp-Snijders C, Sweep FG, Lafeber HN, Delemarre-van de Waal HA: Maturity of the adrenal cortex in very preterm infants is related to gestational age. Pediatr Res. 2002 Sep;52(3):405-10. doi: 10.1203/00006450-200209000-00017. [PubMed:12193676 ]
Gupta MK, Guryev OL, Auchus RJ: 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. Arch Biochem Biophys. 2003 Oct 15;418(2):151-60. doi: 10.1016/j.abb.2003.07.003. [PubMed:14522586 ]
Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. doi: 10.1016/s0039-128x(03)00115-6. [PubMed:14625002 ]
Gibney MJ, Walsh M, Brennan L, Roche HM, German B, van Ommen B: Metabolomics in human nutrition: opportunities and challenges. Am J Clin Nutr. 2005 Sep;82(3):497-503. doi: 10.1093/ajcn.82.3.497. [PubMed:16155259 ]

Showing metabocard for 17-Hydroxyprogesterone (MMDBc0047909)

MOL for #<Metabolite:0x0000564af39fb340>

3D MOL for #<Metabolite:0x0000564af39fb340>

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3D-SDF for #<Metabolite:0x0000564af39fb340>

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3D PDB for #<Metabolite:0x0000564af39fb340>

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Structure for #<Metabolite:0x0000564af39fb340>

3D Structure for #<Metabolite:0x0000564af39fb340>