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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 21:51:01 UTC

Update Date

2021-09-23 21:51:01 UTC

HMDB ID

HMDB0302928

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Carnosolic acid

Description

Carnosolic acid, also known as carnosolate, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Carnosolic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Carnosolic acid can be found in common sage and rosemary, which makes carnosolic acid a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302928
     RDKit          3D
Carnosolic acid
 53 55  0  0  0  0  0  0  0  0999 V2000
    5.3410    1.5668   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243    0.3167   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994   -0.9618   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069    0.4147   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    0.8382   -0.9486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7587    0.6857   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218    0.1195    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207   -0.2977    1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9141   -0.8515    2.5929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6503   -0.1586    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.5671    2.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883   -0.1197    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095   -1.3396    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -1.3590    2.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702   -2.4459    1.1498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    0.9968    1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    1.6899    0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    0.8461    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3321   -0.4790   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439   -0.7885   -1.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8173   -1.5840    0.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330   -0.5435   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    0.1426   -1.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736    1.1013   -1.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4120    1.0476   -2.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0629    1.4506    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0158    1.7047   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7595    2.4689   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631    0.1897   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1818   -0.8964    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -1.6206    0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2955   -1.6200   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.2968   -1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735   -1.1549    3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175   -0.9833    2.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960   -2.3519    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906    1.8067    1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    0.6219    2.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4307    2.2110    1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103    2.5596    0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848    1.4238   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7676    0.6655    0.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6749   -1.6546   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -1.1251   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5615    0.0357   -2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -1.1493    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7790   -2.0078    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1292   -2.4169    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055   -1.6263   -0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471    0.7253   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -0.5998   -2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6228    2.1251   -1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    1.6513   -3.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 10  4  1  0
 22 12  1  0
 24  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
M  END


  Mrv0541 02241223402D          

 25 27  0  0  0  0            999 V2000
   -2.4992   -0.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847   -1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847    0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -0.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675    0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    1.3861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    1.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    2.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1977   -2.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3718   -2.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    2.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3105    0.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    1.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 23  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 15  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 13 22  1  0  0  0  0
 14 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302928

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC2=C(C(O)=C1O)C1(CCCC(C)(C)C1CC2O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-10(2)11-8-12-13(21)9-14-19(3,4)6-5-7-20(14,18(24)25)15(12)17(23)16(11)22/h8,10,13-14,21-23H,5-7,9H2,1-4H3,(H,24,25)

> <INCHI_KEY>
XMKKZBYHMFTMOJ-UHFFFAOYSA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.4333

> <EXACT_MASS>
348.193674006

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.93028700628983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6,9-trihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.910823017666666

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.27550692752116

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.130596294655545

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0614762560128295

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
94.92129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6,9-trihydroxy-7-isopropyl-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302928
     RDKit          3D
Carnosolic acid
 53 55  0  0  0  0  0  0  0  0999 V2000
    5.3410    1.5668   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243    0.3167   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994   -0.9618   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069    0.4147   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    0.8382   -0.9486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7587    0.6857   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218    0.1195    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207   -0.2977    1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9141   -0.8515    2.5929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6503   -0.1586    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.5671    2.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883   -0.1197    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095   -1.3396    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -1.3590    2.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702   -2.4459    1.1498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    0.9968    1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    1.6899    0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    0.8461    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3321   -0.4790   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439   -0.7885   -1.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8173   -1.5840    0.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330   -0.5435   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    0.1426   -1.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736    1.1013   -1.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4120    1.0476   -2.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0629    1.4506    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0158    1.7047   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7595    2.4689   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631    0.1897   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1818   -0.8964    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -1.6206    0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2955   -1.6200   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.2968   -1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735   -1.1549    3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175   -0.9833    2.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960   -2.3519    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906    1.8067    1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    0.6219    2.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4307    2.2110    1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103    2.5596    0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848    1.4238   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7676    0.6655    0.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6749   -1.6546   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -1.1251   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5615    0.0357   -2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -1.1493    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7790   -2.0078    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1292   -2.4169    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055   -1.6263   -0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471    0.7253   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -0.5998   -2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6228    2.1251   -1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    1.6513   -3.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 10  4  1  0
 22 12  1  0
 24  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 15 36  1  0
 16 37  1  0
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 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.665  -0.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.665  -2.022   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.331  -2.793   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.000  -2.022   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.000  -0.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.331   0.288   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667  -2.793   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.664  -2.022   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.664  -0.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667   0.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.993   0.288   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.993   1.822   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.664   2.587   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.667   1.822   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.667  -1.251   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.000   2.587   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.329   2.587   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.665   1.822   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.329   4.129   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.102  -4.129   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.561  -4.129   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.664   4.129   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.771   0.856   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.313   0.856   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.771   2.397   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20   21                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   23                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   22                                                  
CONECT   14   10   13   16                                                  
CONECT   15    8                                                            
CONECT   16   14                                                            
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22   13                                                            
CONECT   23    5   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0302928
HETATM    1  C1  UNL     1       5.341   1.567  -0.469  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.524   0.317  -0.491  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.199  -0.962  -0.153  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.107   0.415  -0.065  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.123   0.838  -0.949  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.759   0.686  -0.658  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.322   0.120   0.507  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.321  -0.298   1.404  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.914  -0.851   2.593  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.650  -0.159   1.131  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.614  -0.567   2.029  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.088  -0.120   0.772  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.110  -1.340   1.692  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.626  -1.359   2.801  1.00  0.00           O  
HETATM   15  O4  UNL     1      -0.470  -2.446   1.150  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.714   0.997   1.529  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.855   1.690   0.877  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.839   0.846   0.158  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.332  -0.479  -0.306  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.944  -0.789  -1.667  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.817  -1.584   0.614  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.833  -0.543  -0.474  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.425   0.143  -1.699  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.274   1.101  -1.636  1.00  0.00           C  
HETATM   25  O5  UNL     1       0.412   1.048  -2.886  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.063   1.451   0.435  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.016   1.705  -1.359  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.759   2.469  -0.220  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.363   0.190  -1.696  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.182  -0.896   0.362  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.543  -1.621   0.494  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.295  -1.620  -1.089  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.447   1.297  -1.858  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.574  -1.155   3.267  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.517  -0.983   2.903  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.296  -2.352   0.474  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.991   1.807   1.837  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.133   0.622   2.528  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.431   2.211   1.710  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.510   2.560   0.240  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.185   1.424  -0.752  1.00  0.00           H  
HETATM   42  H17 UNL     1      -4.768   0.666   0.739  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.675  -1.655  -1.603  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.193  -1.125  -2.382  1.00  0.00           H  
HETATM   45  H20 UNL     1      -4.561   0.036  -2.065  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.071  -1.149   1.626  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.779  -2.008   0.252  1.00  0.00           H  
HETATM   48  H23 UNL     1      -3.129  -2.417   0.711  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.605  -1.626  -0.600  1.00  0.00           H  
HETATM   50  H25 UNL     1      -2.247   0.725  -2.185  1.00  0.00           H  
HETATM   51  H26 UNL     1      -1.144  -0.600  -2.512  1.00  0.00           H  
HETATM   52  H27 UNL     1      -0.623   2.125  -1.518  1.00  0.00           H  
HETATM   53  H28 UNL     1       0.029   1.651  -3.544  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   29
CONECT    3   30   31   32
CONECT    4    5    5   10
CONECT    5    6   33
CONECT    6    7    7   24
CONECT    7    8   12
CONECT    8    9   10   10
CONECT    9   34
CONECT   10   11
CONECT   11   35
CONECT   12   13   16   22
CONECT   13   14   14   15
CONECT   15   36
CONECT   16   17   37   38
CONECT   17   18   39   40
CONECT   18   19   41   42
CONECT   19   20   21   22
CONECT   20   43   44   45
CONECT   21   46   47   48
CONECT   22   23   49
CONECT   23   24   50   51
CONECT   24   25   52
CONECT   25   53
END

HMDB0302928
     RDKit          3D
Carnosolic acid
 53 55  0  0  0  0  0  0  0  0999 V2000
    5.3410    1.5668   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243    0.3167   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1994   -0.9618   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069    0.4147   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    0.8382   -0.9486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7587    0.6857   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218    0.1195    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207   -0.2977    1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9141   -0.8515    2.5929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6503   -0.1586    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.5671    2.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883   -0.1197    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095   -1.3396    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255   -1.3590    2.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702   -2.4459    1.1498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    0.9968    1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    1.6899    0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394    0.8461    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3321   -0.4790   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439   -0.7885   -1.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8173   -1.5840    0.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330   -0.5435   -0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    0.1426   -1.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736    1.1013   -1.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4120    1.0476   -2.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0629    1.4506    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0158    1.7047   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7595    2.4689   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631    0.1897   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1818   -0.8964    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -1.6206    0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2955   -1.6200   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.2968   -1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735   -1.1549    3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175   -0.9833    2.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960   -2.3519    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906    1.8067    1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    0.6219    2.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4307    2.2110    1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103    2.5596    0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848    1.4238   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7676    0.6655    0.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6749   -1.6546   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -1.1251   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5615    0.0357   -2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -1.1493    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7790   -2.0078    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1292   -2.4169    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055   -1.6263   -0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471    0.7253   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -0.5998   -2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6228    2.1251   -1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    1.6513   -3.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 10  4  1  0
 22 12  1  0
 24  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6,9-Trihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylate	Generator
Carnosolate	Generator

Chemical Formula

C₂₀H₂₈O₅

Average Molecular Weight

348.4333

Monoisotopic Molecular Weight

348.193674006

IUPAC Name

5,6,9-trihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid

Traditional Name

5,6,9-trihydroxy-7-isopropyl-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=C(C(O)=C1O)C1(CCCC(C)(C)C1CC2O)C(O)=O

InChI Identifier

InChI=1S/C20H28O5/c1-10(2)11-8-12-13(21)9-14-19(3,4)6-5-7-20(14,18(24)25)15(12)17(23)16(11)22/h8,10,13-14,21-23H,5-7,9H2,1-4H3,(H,24,25)

InChI Key

XMKKZBYHMFTMOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
1-naphthalenecarboxylic acid
1-naphthalenecarboxylic acid or derivatives
Tetralin
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Rosemary (FooDB: FOOD00159)
Common sage (FooDB: FOOD00165)

Not Available

protease inhibitor (HMDB: HMDB0302928)

Indirect biological role

antioxidant (HMDB: HMDB0302928)

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
logP	2.96	ALOGPS
logP	3.91	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-3.1	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	2	ChemAxon
Refractivity	94.92 m³·mol⁻¹	ChemAxon
Polarizability	37.93 Å³	ChemAxon
Number of Rings	3	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
AllCCS	[M+H]+	182.666	32859911
AllCCS	[M+H-H2O]+	179.843	32859911
AllCCS	[M+Na]+	186.022	32859911
AllCCS	[M+NH4]+	185.274	32859911
AllCCS	[M-H]-	189.436	32859911
AllCCS	[M+Na-2H]-	189.818	32859911
AllCCS	[M+HCOO]-	190.38	32859911
DeepCCS	[M+H]+	184.832	30932474
DeepCCS	[M-H]-	182.474	30932474
DeepCCS	[M-2H]-	216.306	30932474
DeepCCS	[M+Na]+	191.533	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 10V, Positive-QTOF	splash10-001j-0029000000-28f733fa6fe524fa2324	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 20V, Positive-QTOF	splash10-0f79-2379000000-427ae0dde798041032bf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 40V, Positive-QTOF	splash10-0079-4191000000-0b4e25f339b4099e3fe7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 10V, Negative-QTOF	splash10-0002-0019000000-66cb4210fadd62bacc7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 20V, Negative-QTOF	splash10-0uds-0059000000-ea2e0022679ea0912d4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 40V, Negative-QTOF	splash10-0f79-1493000000-8c82c23e91e1873a6acb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 10V, Positive-QTOF	splash10-0f72-0029000000-2edfd512cb334a1720d4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 20V, Positive-QTOF	splash10-0uds-0749000000-6c5a9d152fc41ad1d424	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 40V, Positive-QTOF	splash10-00xr-3911000000-7cfc03591df2eadcd634	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 10V, Negative-QTOF	splash10-0002-0029000000-283500a6f5515a0b930c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 20V, Negative-QTOF	splash10-000i-0093000000-38395c3361a15a508ada	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosolic acid 40V, Negative-QTOF	splash10-0079-0391000000-0ba3b5ff68afed68c9a1	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB006923

KNApSAcK ID

Not Available

Chemspider ID

9741216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11566445

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Carnosolic acid (HMDB0302928)

MOL for HMDB0302928 (Carnosolic acid)

3D MOL for HMDB0302928 (Carnosolic acid)

3D SDF for HMDB0302928 (Carnosolic acid)

3D-SDF for HMDB0302928 (Carnosolic acid)

PDB for HMDB0302928 (Carnosolic acid)

3D PDB for HMDB0302928 (Carnosolic acid)

SMILES for HMDB0302928 (Carnosolic acid)

INCHI for HMDB0302928 (Carnosolic acid)

Structure for HMDB0302928 (Carnosolic acid)

3D Structure for HMDB0302928 (Carnosolic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra