Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:52:05 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036701

Secondary Accession Numbers

HMDB36701

Metabolite Identification

Common Name

(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid

Description

(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid, also known as (ent-6α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-Oate, 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-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid.

Structure

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


  Mrv0541 05061309172D          

 25 28  0  0  0  0            999 V2000
    0.0008    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4152    1.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613   -0.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0336    1.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2241    1.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008    0.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727    2.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4168    0.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8194    0.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383    1.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    2.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620    1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4100   -0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488    0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905   -0.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646   -0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818    1.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584    0.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    0.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    3.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6832   -1.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756   -0.7496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1869    0.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4487   -1.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
 10  1  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  5  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19  6  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  2  0  0  0  0
 25 17  1  0  0  0  0
M  END

HMDB0036701
     RDKit          3D
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.7662    0.2762    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247   -0.3987    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6569   -0.3335    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -0.7642    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -1.9703   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0882   -1.3328   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403   -0.5840   -1.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    0.4309   -2.4074 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1465   -0.0505   -1.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9667    0.3243   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473    0.8542   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930    1.9260    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8749    1.4196   -1.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476    2.0327   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1996    1.2685   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7737   -0.1477   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825   -0.9768   -1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249   -0.5823    0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -1.6325    0.8469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8976    0.1809    2.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3459   -0.3319    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -0.9219    1.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -0.0562    2.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -1.2120    1.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8852   -0.8626    3.0294 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    0.9138    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    0.2034   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.7549    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9107   -0.9859    2.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399   -2.7156    0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457   -2.3384   -0.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628   -2.0617   -1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982   -1.3162   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1263    0.1044   -2.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4415   -0.8128   -2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0798    0.8751   -2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6200    1.2408   -0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763    2.8913    0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    1.6911    1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285    1.9967    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    2.2890   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9365    0.6770   -2.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    3.0595   -0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6238    2.1932   -2.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1619    1.1734   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5581    1.8241    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2276   -1.3043   -1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620   -0.3934   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263   -1.8899   -1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4553    1.0027    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9518   -1.1189   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -1.8145    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9150   -0.3371    3.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5048   -2.3448    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -0.0122    3.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  6  2  1  0
 21 11  1  0
 10  4  1  0
 24  4  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
M  END


  Mrv0541 05061309172D          

 25 28  0  0  0  0            999 V2000
    0.0008    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4152    1.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613   -0.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0336    1.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2241    1.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008    0.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727    2.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4168    0.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8194    0.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383    1.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    2.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620    1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4100   -0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488    0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905   -0.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646   -0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818    1.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584    0.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    0.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    3.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6832   -1.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756   -0.7496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1869    0.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4487   -1.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
 10  1  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  5  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19  6  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  2  0  0  0  0
 25 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036701

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-10-8-20-9-11(10)12(21)7-13(20)18(2)5-4-6-19(3,17(24)25)15(18)14(22)16(20)23/h11-16,21-23H,1,4-9H2,2-3H3,(H,24,25)

> <INCHI_KEY>
GDUDOACZUAVXMK-UHFFFAOYSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.4492

> <EXACT_MASS>
350.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.93515317555391

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3,12-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.2713050233333338

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.516162490590627

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.471766508490703

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8946606933706124

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
91.75609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,12-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036701
     RDKit          3D
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.7662    0.2762    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247   -0.3987    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6569   -0.3335    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -0.7642    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -1.9703   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0882   -1.3328   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403   -0.5840   -1.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    0.4309   -2.4074 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1465   -0.0505   -1.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9667    0.3243   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473    0.8542   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930    1.9260    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8749    1.4196   -1.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476    2.0327   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1996    1.2685   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7737   -0.1477   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825   -0.9768   -1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249   -0.5823    0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -1.6325    0.8469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8976    0.1809    2.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3459   -0.3319    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -0.9219    1.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -0.0562    2.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -1.2120    1.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8852   -0.8626    3.0294 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    0.9138    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    0.2034   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.7549    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9107   -0.9859    2.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399   -2.7156    0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457   -2.3384   -0.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628   -2.0617   -1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982   -1.3162   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1263    0.1044   -2.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4415   -0.8128   -2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0798    0.8751   -2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6200    1.2408   -0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763    2.8913    0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    1.6911    1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285    1.9967    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    2.2890   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9365    0.6770   -2.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    3.0595   -0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6238    2.1932   -2.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1619    1.1734   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5581    1.8241    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2276   -1.3043   -1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620   -0.3934   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263   -1.8899   -1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4553    1.0027    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9518   -1.1189   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -1.8145    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9150   -0.3371    3.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5048   -2.3448    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -0.0122    3.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  6  2  1  0
 21 11  1  0
 10  4  1  0
 24  4  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.001   1.633   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.375   3.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.328  -1.044   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.396   3.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.885   3.306   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.895   1.553   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.989   4.032   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.645   0.633   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.320   2.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.530   1.823   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.312   3.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.436   4.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.342   2.449   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.365  -0.488   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.371   0.689   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.836  -0.196   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.201  -0.403   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.873   2.146   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.882   0.392   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.200   1.263   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.004   5.880   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.875  -1.940   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.874  -1.399   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      11.549   0.341   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.171  -1.943   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    5    6                                                       
CONECT    5    4   18                                                       
CONECT    6    4   19                                                       
CONECT    7   12   13                                                       
CONECT    8   10   20                                                       
CONECT    9   11   20                                                       
CONECT   10    1    8   11                                                  
CONECT   11    9   10   12                                                  
CONECT   12    7   11   21                                                  
CONECT   13    7   18   20                                                  
CONECT   14   15   16   22                                                  
CONECT   15   14   18   19                                                  
CONECT   16   14   20   23                                                  
CONECT   17   19   24   25                                                  
CONECT   18    2    5   13   15                                             
CONECT   19    3    6   15   17                                             
CONECT   20    8    9   13   16                                             
CONECT   21   12                                                            
CONECT   22   14                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   17                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0036701
HETATM    1  C1  UNL     1       4.766   0.276   0.201  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.625  -0.399   0.239  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.657  -0.334   1.367  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.349  -0.764   0.671  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.907  -1.970  -0.106  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.088  -1.333  -0.801  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.540  -0.584  -1.985  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.401   0.431  -2.407  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.147  -0.050  -1.720  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.967   0.324  -0.241  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.447   0.854  -0.079  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.493   1.926   0.964  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.875   1.420  -1.414  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.248   2.033  -1.275  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.200   1.268  -0.433  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.774  -0.148  -0.103  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.182  -0.977  -1.344  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.725  -0.582   0.970  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.387  -1.632   0.847  1.00  0.00           O  
HETATM   20  O3  UNL     1      -3.898   0.181   2.144  1.00  0.00           O  
HETATM   21  C18 UNL     1      -1.346  -0.332   0.214  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.029  -0.922   1.567  1.00  0.00           C  
HETATM   23  O4  UNL     1      -1.361  -0.056   2.620  1.00  0.00           O  
HETATM   24  C20 UNL     1       0.437  -1.212   1.729  1.00  0.00           C  
HETATM   25  O5  UNL     1       0.885  -0.863   3.029  1.00  0.00           O  
HETATM   26  H1  UNL     1       5.018   0.914   1.031  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.452   0.203  -0.644  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.596   0.755   1.650  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.911  -0.986   2.199  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.240  -2.716   0.621  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.146  -2.338  -0.814  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.863  -2.062  -1.089  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.498  -1.316  -2.832  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.126   0.104  -2.988  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.441  -0.813  -2.045  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.080   0.875  -2.340  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.620   1.241  -0.125  1.00  0.00           H  
HETATM   38  H13 UNL     1      -0.176   2.891   0.520  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.305   1.691   1.728  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.429   1.997   1.535  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.195   2.289  -1.654  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.937   0.677  -2.211  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.155   3.060  -0.849  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.624   2.193  -2.327  1.00  0.00           H  
HETATM   45  H20 UNL     1      -4.162   1.173  -1.021  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.558   1.824   0.484  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.228  -1.304  -1.824  1.00  0.00           H  
HETATM   48  H23 UNL     1      -3.762  -0.393  -2.062  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.726  -1.890  -1.043  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.455   1.003   2.179  1.00  0.00           H  
HETATM   51  H26 UNL     1      -0.952  -1.119  -0.511  1.00  0.00           H  
HETATM   52  H27 UNL     1      -1.673  -1.815   1.697  1.00  0.00           H  
HETATM   53  H28 UNL     1      -0.915  -0.337   3.448  1.00  0.00           H  
HETATM   54  H29 UNL     1       0.505  -2.345   1.773  1.00  0.00           H  
HETATM   55  H30 UNL     1       1.339  -0.012   3.060  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3    6
CONECT    3    4   28   29
CONECT    4    5   10   24
CONECT    5    6   30   31
CONECT    6    7   32
CONECT    7    8    9   33
CONECT    8   34
CONECT    9   10   35   36
CONECT   10   11   37
CONECT   11   12   13   21
CONECT   12   38   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   45   46
CONECT   16   17   18   21
CONECT   17   47   48   49
CONECT   18   19   19   20
CONECT   20   50
CONECT   21   22   51
CONECT   22   23   24   52
CONECT   23   53
CONECT   24   25   54
CONECT   25   55
END

HMDB0036701
     RDKit          3D
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.7662    0.2762    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247   -0.3987    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6569   -0.3335    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -0.7642    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -1.9703   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0882   -1.3328   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403   -0.5840   -1.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    0.4309   -2.4074 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1465   -0.0505   -1.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9667    0.3243   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473    0.8542   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930    1.9260    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8749    1.4196   -1.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476    2.0327   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1996    1.2685   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7737   -0.1477   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825   -0.9768   -1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249   -0.5823    0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -1.6325    0.8469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8976    0.1809    2.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3459   -0.3319    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -0.9219    1.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -0.0562    2.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -1.2120    1.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8852   -0.8626    3.0294 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    0.9138    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    0.2034   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.7549    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9107   -0.9859    2.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399   -2.7156    0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457   -2.3384   -0.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628   -2.0617   -1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982   -1.3162   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1263    0.1044   -2.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4415   -0.8128   -2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0798    0.8751   -2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6200    1.2408   -0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763    2.8913    0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    1.6911    1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285    1.9967    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    2.2890   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9365    0.6770   -2.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    3.0595   -0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6238    2.1932   -2.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1619    1.1734   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5581    1.8241    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2276   -1.3043   -1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620   -0.3934   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263   -1.8899   -1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4553    1.0027    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9518   -1.1189   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -1.8145    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9150   -0.3371    3.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5048   -2.3448    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -0.0122    3.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  6  2  1  0
 21 11  1  0
 10  4  1  0
 24  4  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(ent-6a,7a,12a)-6,7,12-Trihydroxy-16-kauren-19-Oate	Generator
(ent-6a,7a,12a)-6,7,12-Trihydroxy-16-kauren-19-Oic acid	Generator
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-Oate	Generator
(ent-6Α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-Oate	Generator
(ent-6Α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-Oic acid	Generator
2,3,12-Trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	Generator

Chemical Formula

C₂₀H₃₀O₅

Average Molecular Weight

350.4492

Monoisotopic Molecular Weight

350.20932407

IUPAC Name

2,3,12-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

2,3,12-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

90806-33-0

SMILES

CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O

InChI Identifier

InChI=1S/C20H30O5/c1-10-8-20-9-11(10)12(21)7-13(20)18(2)5-4-6-19(3,17(24)25)15(18)14(22)16(20)23/h11-16,21-23H,1,4-9H2,2-3H3,(H,24,25)

InChI Key

GDUDOACZUAVXMK-UHFFFAOYSA-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
Cyclic alcohol
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036701)

Source

Endogenous

Endogenous (HMDB: HMDB0036701)

Plant

Plant (HMDB: HMDB0036701)
Cucurbitaceae (HMDB: HMDB0036701)

Animal

Animal (HMDB: HMDB0036701)

Exogenous

Food

Food (HMDB: HMDB0036701)

Gourd

Japanese pumpkin (FooDB: FOOD00886)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0036701)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036701)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036701)

Lipid metabolism pathway (HMDB: HMDB0036701)

Cellular process

Cell signaling (HMDB: HMDB0036701)

Biochemical process

Lipid transport (HMDB: HMDB0036701)

Role

Biological role

Energy source (HMDB: HMDB0036701)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036701)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.49 g/L	ALOGPS
logP	0.99	ALOGPS
logP	1.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-0.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.76 m³·mol⁻¹	ChemAxon
Polarizability	37.94 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	182.016	31661259
DarkChem	[M-H]-	176.465	31661259
DeepCCS	[M-2H]-	222.279	30932474
DeepCCS	[M+Na]+	198.569	30932474
AllCCS	[M+H]+	185.7	32859911
AllCCS	[M+H-H2O]+	183.0	32859911
AllCCS	[M+NH4]+	188.1	32859911
AllCCS	[M+Na]+	188.8	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	188.0	32859911
AllCCS	[M+HCOO]-	188.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.02 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3102 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2095.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	188.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	154.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	389.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	529.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	844.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	409.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1266.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	337.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	216.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	99.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid	CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O	3066.3	Standard polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid	CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O	2793.1	Standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid	CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O	3016.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TMS,isomer #1	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C)C3O	3015.8	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TMS,isomer #2	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O[Si](C)(C)C	3007.0	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TMS,isomer #3	C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O	3030.9	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TMS,isomer #4	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O)C3O	2947.1	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #1	C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C)C3O	2946.1	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #2	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O[Si](C)(C)C)C3O	2913.3	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #3	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C)C3O[Si](C)(C)C	2985.5	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #4	C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O[Si](C)(C)C	2956.6	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #5	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O)C3O[Si](C)(C)C	2891.2	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #6	C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O)C3O	2939.6	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TMS,isomer #1	C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O[Si](C)(C)C)C3O	2862.4	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TMS,isomer #2	C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C)C3O[Si](C)(C)C	2912.1	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TMS,isomer #3	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O[Si](C)(C)C)C3O[Si](C)(C)C	2902.4	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TMS,isomer #4	C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O)C3O[Si](C)(C)C	2862.8	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,4TMS,isomer #1	C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O[Si](C)(C)C)C3O[Si](C)(C)C	2875.8	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TBDMS,isomer #1	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C(C)(C)C)C3O	3266.2	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TBDMS,isomer #2	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O[Si](C)(C)C(C)(C)C	3250.6	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TBDMS,isomer #3	C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O	3275.5	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TBDMS,isomer #4	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O)C3O	3224.6	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #1	C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C(C)(C)C)C3O	3424.2	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #2	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O[Si](C)(C)C(C)(C)C)C3O	3413.7	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #3	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C	3483.0	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #4	C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O[Si](C)(C)C(C)(C)C	3424.3	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #5	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O)C3O[Si](C)(C)C(C)(C)C	3387.8	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #6	C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O)C3O	3431.7	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TBDMS,isomer #1	C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O[Si](C)(C)C(C)(C)C)C3O	3566.4	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TBDMS,isomer #2	C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C	3622.4	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TBDMS,isomer #3	C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C	3618.8	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TBDMS,isomer #4	C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O)C3O[Si](C)(C)C(C)(C)C	3566.8	Semi standard non polar	33892256
(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,4TBDMS,isomer #1	C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C	3792.3	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015637

KNApSAcK ID

Not Available

Chemspider ID

35014210

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752042

PDB ID

Not Available

ChEBI ID

175482

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid (HMDB0036701)

MOL for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

3D MOL for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

3D SDF for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

3D-SDF for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

PDB for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

3D PDB for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

SMILES for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

INCHI for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

Structure for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

3D Structure for HMDB0036701 ((ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized