MiMeDB: Showing metabocard for Pregnenolone (MMDBc0047904)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:14:12 UTC

Update Date

2024-10-15 19:45:50 UTC

Metabolite ID

MMDBc0047904

Metabolite Identification

Common Name

Pregnenolone

Description

Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962 , 15823613 , 16632873 , 15134809 ).

Structure

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


  Mrv1652305271900262D          

 26 29  0  0  1  0            999 V2000
   -1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435   -1.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4290   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2134   -0.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4685    1.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164    2.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  9  1  0  0  0  0
 22 16  1  0  0  0  0
 11  8  1  0  0  0  0
 11 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16  7  1  0  0  0  0
 14  5  1  0  0  0  0
 14  1  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  3 26  1  1  0  0  0
 22 10  1  6  0  0  0
 11 12  1  6  0  0  0
 19 13  1  1  0  0  0
 14 15  1  1  0  0  0
 16 17  1  1  0  0  0
 18 23  1  1  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  2  0  0  0  0
M  END

HMDB0000253
     RDKit          3D
Pregnenolone
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.9957   -0.2681   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054    0.0711   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    0.7658   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -0.4433    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6667    0.0621    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    0.5651    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4075   -0.1353    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0163    0.3226    0.8327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7109    0.1085    2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    0.5472    1.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268    0.4477    0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354    0.9131    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9786   -0.1566   -0.0007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3535    0.2929   -1.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -1.4312   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2413   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086   -0.1085   -0.4095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0902    0.9668   -1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062   -0.6095   -0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0068   -0.7834   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -0.9798   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    0.0206   -0.4036 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0943    1.3798   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    0.1365   -1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.2460    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -1.3616   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.5507   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3986    0.8867    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101   -0.7813    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.6533    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1258    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204   -1.2135    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747    1.3685    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -0.9783    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668    0.7366    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    0.9771    2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048    1.0411    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2360    1.9040    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9156   -0.3729    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5526    1.2579   -1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7660   -2.3026   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7735   -1.5448    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.0430   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -2.1893   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230    0.5085   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.6248   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002    1.6161   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -1.5889    0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    0.0163   -2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -1.7151   -1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029   -0.8566   -2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -2.0340   -1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    2.0106   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    1.2713   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    1.8455   -0.8595 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  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END


  Mrv1652305271900262D          

 26 29  0  0  1  0            999 V2000
   -1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435   -1.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4290   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2134   -0.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4685    1.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164    2.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  9  1  0  0  0  0
 22 16  1  0  0  0  0
 11  8  1  0  0  0  0
 11 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16  7  1  0  0  0  0
 14  5  1  0  0  0  0
 14  1  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  3 26  1  1  0  0  0
 22 10  1  6  0  0  0
 11 12  1  6  0  0  0
 19 13  1  1  0  0  0
 14 15  1  1  0  0  0
 16 17  1  1  0  0  0
 18 23  1  1  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047904

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1

> <INCHI_KEY>
ORNBQBCIOKFOEO-QGVNFLHTSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.08645703431432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
3.581358452666668

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.403038799839706

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972432940071755

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.7567

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000253
     RDKit          3D
Pregnenolone
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.9957   -0.2681   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054    0.0711   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    0.7658   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -0.4433    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6667    0.0621    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    0.5651    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4075   -0.1353    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0163    0.3226    0.8327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7109    0.1085    2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    0.5472    1.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268    0.4477    0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354    0.9131    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9786   -0.1566   -0.0007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3535    0.2929   -1.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -1.4312   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2413   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086   -0.1085   -0.4095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0902    0.9668   -1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062   -0.6095   -0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0068   -0.7834   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -0.9798   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    0.0206   -0.4036 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0943    1.3798   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    0.1365   -1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.2460    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -1.3616   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.5507   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3986    0.8867    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101   -0.7813    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.6533    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1258    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204   -1.2135    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747    1.3685    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -0.9783    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668    0.7366    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    0.9771    2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048    1.0411    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2360    1.9040    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9156   -0.3729    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5526    1.2579   -1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7660   -2.3026   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7735   -1.5448    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.0430   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -2.1893   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230    0.5085   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.6248   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002    1.6161   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -1.5889    0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    0.0163   -2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -1.7151   -1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029   -0.8566   -2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -2.0340   -1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    2.0106   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    1.2713   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    1.8455   -0.8595 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  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.608   3.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.114   3.801   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.577   4.625   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   14    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2   26                                                  
CONECT    4    5    3                                                       
CONECT    5   14    4    6                                                  
CONECT    6    7    5                                                       
CONECT    7   16    6                                                       
CONECT    8   11    9                                                       
CONECT    9   19    8                                                       
CONECT   10   22                                                            
CONECT   11    8   14   16   12                                             
CONECT   12   11                                                            
CONECT   13   19                                                            
CONECT   14   11    5    1   15                                             
CONECT   15   14                                                            
CONECT   16   22   11    7   17                                             
CONECT   17   16                                                            
CONECT   18   23   19   21                                                  
CONECT   19    9   13   18   22                                             
CONECT   20   21   22                                                       
CONECT   21   20   18                                                       
CONECT   22   16   10   19   20                                             
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0000253
HETATM    1  C1  UNL     1       5.996  -0.268  -0.410  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.605   0.071  -0.793  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.425   0.766  -1.759  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.500  -0.443   0.006  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.667   0.062   1.444  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.302   0.565   1.870  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.407  -0.135   0.902  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.016   0.323   0.833  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.711   0.108   2.173  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.107   0.547   1.976  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.727   0.448   0.818  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.135   0.913   0.709  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.979  -0.157  -0.001  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.353   0.293  -1.241  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.184  -1.431  -0.004  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.977  -1.241  -0.895  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.109  -0.109  -0.409  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.090   0.967  -1.466  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.706  -0.610  -0.151  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.007  -0.783  -1.442  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.472  -0.980  -1.360  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.120   0.021  -0.404  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.094   1.380  -1.002  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.738   0.137  -1.131  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.202   0.246   0.563  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.138  -1.362  -0.246  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.502  -1.551  -0.035  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.399   0.887   1.503  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.010  -0.781   2.087  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.225   1.653   1.870  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.109   0.126   2.891  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.420  -1.213   1.155  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.175   1.369   0.586  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.656  -0.978   2.456  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.167   0.737   2.902  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.676   0.977   2.807  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.605   1.041   1.715  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.236   1.904   0.226  1.00  0.00           H  
HETATM   39  H16 UNL     1      -5.916  -0.373   0.565  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.553   1.258  -1.203  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.766  -2.303  -0.310  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.774  -1.545   1.042  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.380  -1.043  -1.921  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.404  -2.189  -0.987  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.223   0.509  -2.485  1.00  0.00           H  
HETATM   46  H23 UNL     1      -2.965   1.625  -1.319  1.00  0.00           H  
HETATM   47  H24 UNL     1      -1.200   1.616  -1.426  1.00  0.00           H  
HETATM   48  H25 UNL     1      -0.778  -1.589   0.363  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.203   0.016  -2.195  1.00  0.00           H  
HETATM   50  H27 UNL     1      -0.424  -1.715  -1.916  1.00  0.00           H  
HETATM   51  H28 UNL     1       1.903  -0.857  -2.378  1.00  0.00           H  
HETATM   52  H29 UNL     1       1.718  -2.034  -1.061  1.00  0.00           H  
HETATM   53  H30 UNL     1       2.892   2.011  -0.546  1.00  0.00           H  
HETATM   54  H31 UNL     1       2.201   1.271  -2.107  1.00  0.00           H  
HETATM   55  H32 UNL     1       1.108   1.846  -0.859  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5   22   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   22   32
CONECT    8    9   19   33
CONECT    9   10   34   35
CONECT   10   11   11   36
CONECT   11   12   17
CONECT   12   13   37   38
CONECT   13   14   15   39
CONECT   14   40
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   19
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23
CONECT   23   53   54   55
END

HMDB0000253
     RDKit          3D
Pregnenolone
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.9957   -0.2681   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054    0.0711   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    0.7658   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -0.4433    0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6667    0.0621    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    0.5651    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4075   -0.1353    0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0163    0.3226    0.8327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7109    0.1085    2.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    0.5472    1.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268    0.4477    0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354    0.9131    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9786   -0.1566   -0.0007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3535    0.2929   -1.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -1.4312   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2413   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086   -0.1085   -0.4095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0902    0.9668   -1.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062   -0.6095   -0.1513 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0068   -0.7834   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -0.9798   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    0.0206   -0.4036 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0943    1.3798   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7376    0.1365   -1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.2460    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -1.3616   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.5507   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3986    0.8867    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101   -0.7813    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    1.6533    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1258    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204   -1.2135    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747    1.3685    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -0.9783    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668    0.7366    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    0.9771    2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048    1.0411    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2360    1.9040    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9156   -0.3729    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5526    1.2579   -1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7660   -2.3026   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7735   -1.5448    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -1.0430   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -2.1893   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230    0.5085   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.6248   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002    1.6161   -1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -1.5889    0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    0.0163   -2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -1.7151   -1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029   -0.8566   -2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -2.0340   -1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    2.0106   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    1.2713   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    1.8455   -0.8595 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  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

Synonyms

Value	Source
(3BETA)-3-HYDROXYPREGN-5-en-20-one	ChEBI
3beta-Hydroxypregn-5-en-20-one	ChEBI
5-Pregnen-3beta-ol-20-one	ChEBI
(3b)-3-HYDROXYPREGN-5-en-20-one	Generator
(3Β)-3-hydroxypregn-5-en-20-one	Generator
3b-Hydroxypregn-5-en-20-one	Generator
3Β-hydroxypregn-5-en-20-one	Generator
5-Pregnen-3b-ol-20-one	Generator
5-Pregnen-3β-ol-20-one	Generator
5-Pregnen-3-beta-ol-20-one	HMDB
5 Pregnen 3 beta ol 20 one	HMDB

Molecular Formula

C₂₁H₃₂O₂

Average Mass

316.4776

Monoisotopic Mass

316.240230268

IUPAC Name

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

Traditional Name

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

CAS Registry Number

145-13-1

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1

InChI Key

ORNBQBCIOKFOEO-QGVNFLHTSA-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-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:16581 )
20-oxo steroid (CHEBI:16581 )
C21-steroid (CHEBI:16581 )
Pregnane and derivatives [Fig] (C01953 )
Progestagens (C01953 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030088 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.06	ALOGPS
logP	3.58	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.76 m³·mol⁻¹	ChemAxon
Polarizability	38.09 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0fic-5910000000-4b4de0891180a420522a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05o0-2982000000-90eb349ceb4f7cdf4bf0	2017-09-12	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_1) - 70eV, Positive	Not Available	2021-11-05	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0195000000-742fffef9b8fa170f05e	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0391000000-7f19b3f9aed012b1e539	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kbo-3390000000-f6f0115bbcd9afb5ddb9	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0039000000-5c36ec019f325626a9b6	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0089000000-99239f61c3086ee3d434	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0592-1090000000-66cb81b0a398e104af3c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0059000000-29a13c8b5bcf95bf2c0e	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ls-0091000000-ceb36b1daa98969bf576	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0069000000-4c14a1135d3725f8f03a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mk-0591000000-a85817c6a0529a583cdf	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2920000000-465c7c1e069f6588a706	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-6920000000-2b11c86505b10fe4485f	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, CDCl₃, experimental)		2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Adrenal Cortex
Adrenal Gland
Blood
Brain
Cerebrospinal Fluid (CSF)
Feces
Kidney
Neuron
Ovary
Placenta
Testis
Urine

Tissue Locations

Adrenal Cortex
Adrenal Gland
Brain
Kidney
Neuron
Ovary
Placenta
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192023	Sulfotransferase family cytosolic 2B member 1	Enzyme	O00204	Homo sapiens
MMDBp0192150	Steryl-sulfatase	Unknown	P08842	Homo sapiens
MMDBp0192362	Cholesterol side-chain cleavage enzyme, mitochondrial	Unknown	P05108	Homo sapiens
MMDBp0192653	Steroid 17-alpha-hydroxylase/17,20 lyase	Unknown	P05093	Homo sapiens
MMDBp0193172	25-hydroxycholesterol 7-alpha-hydroxylase	Unknown	O75881	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
MMDBp0194155	Cytochrome P450 21-hydroxylase	Enzyme	Q16874	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
Aldosterone from Steroidogenesis

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001476	Pregnenolone	Progesterone	Not Available	VMH	16023337
MMDBr0001477	Pregnenolone	Progesterone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2	VMH	16023337
MMDBr0001840	Cholesterol	4-Methylpentanal	cytochrome P450, family 11, subfamily A, polypeptide 1	VMH	16232916
MMDBr0001844	Pregnenolone	17a-Hydroxypregnenolone	cytochrome P450, family 17, subfamily A, polypeptide 1	VMH	7893148
MMDBr0001990	Phosphoadenosine phosphosulfate	Adenosine 3',5'-diphosphate	sulfotransferase family, cytosolic, 1A, phenol-preferring, member 3	VMH	12145317 9799594
MMDBr0003960	Pregnenolone sulfate	Pregnenolone	steroid sulfatase (microsomal), isozyme S	VMH	10049998 1606923
MMDBr0003961	Pregnenolone sulfate	Pregnenolone	steroid sulfatase (microsomal), isozyme S	VMH	10049998 1606923
MMDBr0003962	Pregnenolone sulfate	Pregnenolone	steroid sulfatase (microsomal), isozyme S	VMH	10049998 1606923
MMDBr0003963	Pregnenolone sulfate	Pregnenolone	steroid sulfatase (microsomal), isozyme S	VMH	10049998 1606923
MMDBr0009608	20a,22b-Dihydroxycholesterol	4-Methylpentanal	cytochrome P450, family 11, subfamily A, polypeptide 1	VMH; KEGG	30371894
MMDBr0009610	Pregnenolone	21-Hydroxypregnenolone	cytochrome P450, family 21, subfamily A, polypeptide 2	VMH; KEGG	30371894
MMDBr0009612	Pregnenolone	3Beta,7Alpha-Dihydroxy-5-Pregnen-20-One	cytochrome P450, family 7, subfamily B, polypeptide 1	VMH; KEGG	30371894
MMDBr0009613	Pregnenolone	17a-Hydroxypregnenolone	cytochrome P450, family 17, subfamily A, polypeptide 1	VMH	30371894
MMDBr0009622	Pregnenolone	pregn-5-ene-3,20-dione	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Postpartum depression		Association	Human Blood	HMDB	11739473
Premenstrual dysphoric disorder	Decreased	Association	Human Blood	HMDB	12215085
Prepartum depression		Association	Human Blood	HMDB	11739473

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	3	Human feces; Human	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

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	0.00401				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	0.00209	0.00090			uM	Adult (>18 years old)	Female	Postpartum depression	HMDB	11739473
Human Blood	Detected and Quantified	0.00974	0.00371			uM	Adult (>18 years old)	Female	Postpartum depression	HMDB	11739473
Human Blood	Detected and Quantified	0.00082	0.00071			uM	Adult (>18 years old)	Female	Premenstrual dysphoric disorder (follicular stage of menstrual cycle)	HMDB	12215085
Human Blood	Detected and Quantified	0.00169	0.00107			uM	Adult (>18 years old)	Female	Premenstrual dysphoric disorder (late luteal stage of menstrual cycle)	HMDB	12215085
Human Blood	Detected and Quantified	0.00179	0.00108			uM	Adult (>18 years old)	Female	Premenstrual dysphoric disorder (mid luteal stage of menstrual cycle)	HMDB	12215085
Human Blood	Detected and Quantified	0.0423	0.0130			uM	Adult (>18 years old)	Female	Prepartum depression	HMDB	11739473
Human Blood	Detected and Quantified	0.0684	0.0222			uM	Adult (>18 years old)	Female	Prepartum depression	HMDB	11739473
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00013		0.000082	0.00019	uM	Adult (>18 years old)	Both	Normal	HMDB	10625505
Human Blood	Detected and Quantified	0.00054	0.00033			uM	Adult (>18 years old)	Female	Normal	HMDB	12215085
Human Blood	Detected and Quantified	0.00083	0.00080			uM	Adult (>18 years old)	Both	Normal	HMDB	12215085
Human Blood	Detected and Quantified	0.00088	0.00062			uM	Adult (>18 years old)	Female	Normal	HMDB	12215085
Human Blood	Detected and Quantified	0.00168	0.00137			uM	Adult (>18 years old)	Female	Normal	HMDB	11739473
Human Blood	Detected and Quantified	0.00186	0.00090			uM	Adult (>18 years old)	Female	Normal	HMDB	11739473
Human Blood	Detected and Quantified	0.00373	0.00214			uM	Adult (>18 years old)	Female	Normal	HMDB	11739473
Human Blood	Detected and Quantified	0.00424	0.00236			uM	Adult (>18 years old)	Female	Normal	HMDB	11739473
Human Blood	Detected and Quantified			0.00474	0.0632	uM	Newborn (0-30 days old)	Female	Normal	HMDB	18182448
Human Blood	Detected and Quantified	0.00985	0.00851			uM	Adult (>18 years old)	Female	Normal	HMDB	11739473
Human Blood	Detected and Quantified	0.013	0.0027			uM	Adult (>18 years old)	Both	Normal	HMDB	10625505
Human Blood	Detected and Quantified	0.0147	0.0084			uM	Adult (>18 years old)	Female	Normal	HMDB	11739473
Human Blood	Detected and Quantified	0.0429	0.0325			uM	Adult (>18 years old)	Female	Normal	HMDB	11739473
Human Blood	Detected and Quantified	0.0573	0.0133			uM	Adult (>18 years old)	Female	Normal	HMDB	11739473
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 Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Ovary	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	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 Blood	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22944140
Human Blood	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	22944140
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

HMDB0000253

DrugBank ID

DB02789

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00047082

Chemspider ID

8611

KEGG Compound ID

C01953

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pregnenolone

METLIN ID

Not Available

PubChem Compound

8955

PDB ID

Not Available

ChEBI ID

16581

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Doouss TW, Skinner SJ, Couch RA: Synthesis of dehydroepiandrosterone and dehydroepiandrosterone sulphate by the human adrenal. J Endocrinol. 1975 Jul;66(1):1-12. [PubMed:126268 ]
Nishida S, Matsumura S, Horino M, Matsuki M, Oyama H, Tenku A, Kakita K, Tanaka H, Omukai Y: Dexamethasone suppressibility of plasma pregnenolone or dehydroepiandrosterone in gonadectomized patients. Steroids. 1979 Oct;34(4):471-6. doi: 10.1016/0039-128x(79)90107-7. [PubMed:229589 ]
Morfin R, Young J, Corpechot C, Egestad B, Sjovall J, Baulieu EE: Neurosteroids: pregnenolone in human sciatic nerves. Proc Natl Acad Sci U S A. 1992 Aug 1;89(15):6790-3. doi: 10.1073/pnas.89.15.6790. [PubMed:1386671 ]
Weusten JJ, Smals AG, Hofman JA, Kloppenborg PW, Benraad TJ: Early time sequence in pregnenolone metabolism to testosterone in homogenates of human and rat testis. Endocrinology. 1987 May;120(5):1909-13. doi: 10.1210/endo-120-5-1909. [PubMed:3569120 ]
Lykkesfeldt G, Nielsen MD, Lykkesfeldt AE: Placental steroid sulfatase deficiency: biochemical diagnosis and clinical review. Obstet Gynecol. 1984 Jul;64(1):49-54. [PubMed:6234482 ]
Eriksson CJ, Widenius TV, Leinonen P, Harkonen M, Ylikahri RH: Inhibition of testosterone biosynthesis by ethanol: relation to the pregnenolone-to-testosterone pathway. FEBS Lett. 1984 Jul 9;172(2):177-82. doi: 10.1016/0014-5793(84)81121-7. [PubMed:6540203 ]
Schoneshofer M, Weber B: Specific estimation of fifteen unconjugated, non-metabolized steroid hormones in human urine. J Steroid Biochem. 1983 Jan;18(1):65-73. doi: 10.1016/0022-4731(83)90332-1. [PubMed:6865405 ]
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Showing metabocard for Pregnenolone (MMDBc0047904)

MOL for #<Metabolite:0x00007fdb71a681d8>

3D MOL for #<Metabolite:0x00007fdb71a681d8>

3D SDF for #<Metabolite:0x00007fdb71a681d8>

3D-SDF for #<Metabolite:0x00007fdb71a681d8>

PDB for #<Metabolite:0x00007fdb71a681d8>

3D PDB for #<Metabolite:0x00007fdb71a681d8>

SMILES for #<Metabolite:0x00007fdb71a681d8>

INCHI for #<Metabolite:0x00007fdb71a681d8>

Structure for #<Metabolite:0x00007fdb71a681d8>

3D Structure for #<Metabolite:0x00007fdb71a681d8>