MiMeDB: Showing metabocard for ent-kaurenoate (MMDBc0053223)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:17:49 UTC

Update Date

2022-09-01 02:19:41 UTC

Metabolite ID

MMDBc0053223

Metabolite Identification

Common Name

ent-kaurenoate

Description

ent-kaur-16-en-19-oic acid, also known as kaurenic acid or ent-kaurenoate, belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review a significant number of articles have been published on ent-kaur-16-en-19-oic acid.

Structure

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

HMDB0302664
     RDKit          3D
(-)-Kaur-16-en-19-oic acid
 52 55  0  0  0  0  0  0  0  0999 V2000
    5.1288    0.5247   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.3965    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239    1.4259   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    0.7208    0.4345 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6816    1.6973    1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    0.8506    1.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772    0.5613    0.3558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5362   -0.2970   -0.6030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6815   -1.7713   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359   -0.0295   -1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -0.3819   -1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    0.1010   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037    0.2319    0.5738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2869    1.4980    1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0007   -0.8287    1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0730   -1.3507    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -1.3029    1.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8886    0.1570   -0.7760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7969   -0.8125   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280   -1.6643   -0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733   -0.8435    0.5565 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1225   -0.2587    1.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5244    1.4642   -0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8491   -0.2878   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0541    2.2239    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709    1.7825   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278    2.0995    2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926    2.4299    0.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343    1.5062    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -0.0256    2.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3068    1.5951   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1930   -2.2160    0.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -2.2824   -1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799   -2.0207   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1519    1.0672   -2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7642   -0.5877   -2.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398   -1.4741   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497    0.0981   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -0.6325   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542    1.0507   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1585    1.4009    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338    2.3920    0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3921    1.4627    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666   -2.2685    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197    1.0590   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.2217   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -1.4514   -2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1245   -2.5069   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4745   -2.0765   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336   -1.4166    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994   -1.0879    1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    0.3003    2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 15 16  2  0
 15 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  2  1  0
 18  4  1  0
 22  4  1  0
 13  7  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  6
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 17 44  1  0
 18 45  1  6
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  1
 22 51  1  0
 22 52  1  0
M  END

 
  Mrv1652303102018242D          

 24 27  0  0  1  0            999 V2000
   26.7034  -19.9804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.9929  -19.5648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.7034  -20.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4216  -19.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2756  -19.9733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.0001  -18.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9896  -21.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4288  -18.7511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.2756  -20.7976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.5645  -19.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2684  -19.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7141  -18.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5574  -21.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.8434  -19.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8434  -20.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1418  -21.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9896  -20.4068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.2720  -21.6359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.4335  -20.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1516  -19.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9668  -18.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7757  -22.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5513  -22.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3499  -22.7548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  1  0  0  0
  7  9  1  0  0  0  0
  8 12  1  0  0  0  0
 14 15  1  0  0  0  0
  2 17  1  1  0  0  0
  9 18  1  1  0  0  0
  1 19  1  1  0  0  0
  1  2  1  0  0  0  0
  8 20  1  1  0  0  0
 19 20  1  0  0  0  0
  1  3  1  0  0  0  0
 20 21  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
 13 22  1  6  0  0  0
  2  6  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053223

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CCC[C@@]21C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,18-,19-,20-/m1/s1

> <INCHI_KEY>
NIKHGUQULKYIGE-OTCXFQBHSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.31868003107545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
4.8078307643333345

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.839023750520022

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.36359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302664
     RDKit          3D
(-)-Kaur-16-en-19-oic acid
 52 55  0  0  0  0  0  0  0  0999 V2000
    5.1288    0.5247   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.3965    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239    1.4259   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    0.7208    0.4345 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6816    1.6973    1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    0.8506    1.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772    0.5613    0.3558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5362   -0.2970   -0.6030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6815   -1.7713   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359   -0.0295   -1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -0.3819   -1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    0.1010   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037    0.2319    0.5738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2869    1.4980    1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0007   -0.8287    1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0730   -1.3507    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -1.3029    1.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8886    0.1570   -0.7760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7969   -0.8125   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280   -1.6643   -0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733   -0.8435    0.5565 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1225   -0.2587    1.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5244    1.4642   -0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8491   -0.2878   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0541    2.2239    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709    1.7825   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278    2.0995    2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926    2.4299    0.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343    1.5062    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -0.0256    2.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3068    1.5951   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1930   -2.2160    0.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -2.2824   -1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799   -2.0207   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1519    1.0672   -2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7642   -0.5877   -2.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398   -1.4741   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497    0.0981   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -0.6325   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542    1.0507   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1585    1.4009    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338    2.3920    0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3921    1.4627    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666   -2.2685    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197    1.0590   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.2217   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -1.4514   -2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1245   -2.5069   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4745   -2.0765   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336   -1.4166    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994   -1.0879    1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    0.3003    2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 15 16  2  0
 15 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  2  1  0
 18  4  1  0
 22  4  1  0
 13  7  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  6
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 17 44  1  0
 18 45  1  6
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  1
 22 51  1  0
 22 52  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      49.846 -37.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      48.520 -36.521   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      49.846 -38.835   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      51.187 -36.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.181 -37.283   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      48.534 -34.982   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.514 -39.598   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      51.200 -35.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      47.181 -38.822   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.854 -36.514   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      47.168 -35.745   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.866 -34.226   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      45.840 -39.598   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      44.508 -37.283   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.508 -38.822   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.065 -40.926   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      48.514 -38.093   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      47.174 -40.387   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      51.209 -38.076   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      52.550 -35.788   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      54.071 -35.393   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.248 -41.119   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      47.696 -41.866   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      45.453 -42.476   0.000  0.00  0.00           O+0
CONECT    1   19    2    3    4                                             
CONECT    2   17    1    5    6                                             
CONECT    3    7    1                                                       
CONECT    4    8    1                                                       
CONECT    5    9   10   11    2                                             
CONECT    6   12    2                                                       
CONECT    7    3    9                                                       
CONECT    8    4   12   20                                                  
CONECT    9    5   13    7   18                                             
CONECT   10    5   14                                                       
CONECT   11    5                                                            
CONECT   12    6    8                                                       
CONECT   13    9   15   16   22                                             
CONECT   14   10   15                                                       
CONECT   15   13   14                                                       
CONECT   16   13                                                            
CONECT   17    2                                                            
CONECT   18    9                                                            
CONECT   19    1   20                                                       
CONECT   20    8   19   21                                                  
CONECT   21   20                                                            
CONECT   22   13   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0302664
HETATM    1  C1  UNL     1       5.129   0.525  -0.347  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.875   0.396   0.006  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.824   1.426  -0.067  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.552   0.721   0.434  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.682   1.697   1.188  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.523   0.851   1.635  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.277   0.561   0.356  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.536  -0.297  -0.603  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.681  -1.771  -0.422  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.236  -0.029  -1.956  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.688  -0.382  -1.898  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.428   0.101  -0.717  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.704   0.232   0.574  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.287   1.498   1.268  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.001  -0.829   1.545  1.00  0.00           C  
HETATM   16  O1  UNL     1      -2.073  -1.351   2.197  1.00  0.00           O  
HETATM   17  O2  UNL     1      -4.281  -1.303   1.795  1.00  0.00           O  
HETATM   18  C16 UNL     1       0.889   0.157  -0.776  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.797  -0.813  -1.430  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.628  -1.664  -0.515  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.273  -0.844   0.557  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.123  -0.259   1.387  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.524   1.464  -0.749  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.849  -0.288  -0.262  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.054   2.224   0.644  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.671   1.783  -1.110  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.228   2.100   2.038  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.293   2.430   0.477  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.134   1.506   2.250  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.202  -0.026   2.196  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.307   1.595  -0.140  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.193  -2.216   0.436  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.322  -2.282  -1.343  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.780  -2.021  -0.427  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.152   1.067  -2.108  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.764  -0.588  -2.767  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.840  -1.474  -2.076  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.150   0.098  -2.815  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.272  -0.633  -0.534  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.954   1.051  -0.947  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.158   1.401   2.360  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.834   2.392   0.842  1.00  0.00           H  
HETATM   43  H21 UNL     1      -4.392   1.463   1.073  1.00  0.00           H  
HETATM   44  H22 UNL     1      -4.467  -2.269   1.539  1.00  0.00           H  
HETATM   45  H23 UNL     1       0.820   1.059  -1.468  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.562  -0.222  -2.026  1.00  0.00           H  
HETATM   47  H25 UNL     1       1.316  -1.451  -2.213  1.00  0.00           H  
HETATM   48  H26 UNL     1       2.124  -2.507  -0.061  1.00  0.00           H  
HETATM   49  H27 UNL     1       3.475  -2.077  -1.143  1.00  0.00           H  
HETATM   50  H28 UNL     1       3.934  -1.417   1.203  1.00  0.00           H  
HETATM   51  H29 UNL     1       1.499  -1.088   1.694  1.00  0.00           H  
HETATM   52  H30 UNL     1       2.518   0.300   2.259  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   21
CONECT    3    4   25   26
CONECT    4    5   18   22
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   13   31
CONECT    8    9   10   18
CONECT    9   32   33   34
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   39   40
CONECT   13   14   15
CONECT   14   41   42   43
CONECT   15   16   16   17
CONECT   17   44
CONECT   18   19   45
CONECT   19   20   46   47
CONECT   20   21   48   49
CONECT   21   22   50
CONECT   22   51   52
END

HMDB0302664
     RDKit          3D
(-)-Kaur-16-en-19-oic acid
 52 55  0  0  0  0  0  0  0  0999 V2000
    5.1288    0.5247   -0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.3965    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239    1.4259   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    0.7208    0.4345 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6816    1.6973    1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    0.8506    1.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772    0.5613    0.3558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5362   -0.2970   -0.6030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6815   -1.7713   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359   -0.0295   -1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -0.3819   -1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    0.1010   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037    0.2319    0.5738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2869    1.4980    1.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0007   -0.8287    1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0730   -1.3507    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -1.3029    1.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8886    0.1570   -0.7760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7969   -0.8125   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280   -1.6643   -0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733   -0.8435    0.5565 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1225   -0.2587    1.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5244    1.4642   -0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8491   -0.2878   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0541    2.2239    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709    1.7825   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278    2.0995    2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926    2.4299    0.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1343    1.5062    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -0.0256    2.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3068    1.5951   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1930   -2.2160    0.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -2.2824   -1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799   -2.0207   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1519    1.0672   -2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7642   -0.5877   -2.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398   -1.4741   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497    0.0981   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -0.6325   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542    1.0507   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1585    1.4009    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338    2.3920    0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3921    1.4627    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666   -2.2685    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197    1.0590   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.2217   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -1.4514   -2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1245   -2.5069   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4745   -2.0765   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336   -1.4166    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994   -1.0879    1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    0.3003    2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 15 16  2  0
 15 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  2  1  0
 18  4  1  0
 22  4  1  0
 13  7  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  6
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 17 44  1  0
 18 45  1  6
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  1
 22 51  1  0
 22 52  1  0
M  END

Synonyms

Value	Source
(-)-Kaur-16-en-19-Oic acid	ChEBI
(5beta,8alpha,9beta,10alpha,13alpha)-Kaur-16-en-18-Oic acid	ChEBI
ent-Kaur-16(17)-en-19-Oic acid	ChEBI
ent-Kaurenoic acid	ChEBI
Kaur-16-en-18-Oic acid	ChEBI
Kauren-19-Oic acid	ChEBI
Kaurenic acid	ChEBI
Kaurenoic acid	ChEBI
ent-Kaur-16-en-19-Oate	Kegg
(-)-Kaur-16-en-19-Oate	Generator
(5b,8a,9b,10a,13a)-Kaur-16-en-18-Oate	Generator
(5b,8a,9b,10a,13a)-Kaur-16-en-18-Oic acid	Generator
(5beta,8alpha,9beta,10alpha,13alpha)-Kaur-16-en-18-Oate	Generator
(5Β,8α,9β,10α,13α)-kaur-16-en-18-Oate	Generator
(5Β,8α,9β,10α,13α)-kaur-16-en-18-Oic acid	Generator
ent-Kaur-16(17)-en-19-Oate	Generator
ent-Kaurenoate	Generator
Kaur-16-en-18-Oate	Generator
Kauren-19-Oate	Generator
Kaurenate	Generator
Kaurenoate	Generator
ent-Kaur-16-en-18-Oic acid	MeSH
3beta-Hydroxy-kaurenoic acid	MeSH
ent-Kaur-16-en-19-Oic acid	KEGG

Molecular Formula

C₂₀H₃₀O₂

Average Mass

302.458

Monoisotopic Mass

302.224580206

IUPAC Name

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

Traditional Name

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CCC[C@@]21C)C(O)=O

InChI Identifier

InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,18-,19-,20-/m1/s1

InChI Key

NIKHGUQULKYIGE-OTCXFQBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

ent-kaurane diterpenoid (CHEBI:15417 )
Kaurane and phyllocladane diterpenoids (C11874 )
Kaurenes (C11874 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	4.13	ALOGPS
logP	4.81	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.36 m³·mol⁻¹	ChemAxon
Polarizability	35.32 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0189000000-e32ee1de5a9c608c2a44	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0391000000-e394ed814c12150daac8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kr-4980000000-a62048379e0c65cfa374	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0049000000-7e4d4b429d5eff18ab7e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-0094000000-8f1bdf9553eed92d0c8c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052o-1090000000-0d495a6257dc2d019e9c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zfr-0089000000-c65698a8dba37e012d50	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zmr-0943000000-2ffd59d91ab4e2b79ac4	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014u-9720000000-930c6014a094be91c659	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-16d58525184e918518fa	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-16d58525184e918518fa	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udj-0097000000-208d1681517a7ae9b6f9	2021-10-21	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces

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

External Links

HMDB ID

HMDB0302664

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15417

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for ent-kaurenoate (MMDBc0053223)

MOL for #<Metabolite:0x00007fecd3801840>

3D MOL for #<Metabolite:0x00007fecd3801840>

3D SDF for #<Metabolite:0x00007fecd3801840>

3D-SDF for #<Metabolite:0x00007fecd3801840>

PDB for #<Metabolite:0x00007fecd3801840>

3D PDB for #<Metabolite:0x00007fecd3801840>

SMILES for #<Metabolite:0x00007fecd3801840>

INCHI for #<Metabolite:0x00007fecd3801840>

Structure for #<Metabolite:0x00007fecd3801840>

3D Structure for #<Metabolite:0x00007fecd3801840>