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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:37 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002121

Secondary Accession Numbers

HMDB02121

Metabolite Identification

Common Name

Carnosol

Description

Carnosol is a naturally occurring phenolic diterpene found in rosemary (Rosemarinus officinalis, Labiatae). It has been known that an extract of rosemary leaves contains high antioxidative activity. Ninety percent of this antioxidative activity can be attributed to carnosol and carnosic acid. Carnosic acid is easily converted to carnosol by oxidation. Carnosol has multiple beneficial medicinal effects including anti-inflammatory, anti-microbial and anti-cancer activities in various disease models. Carnosol may possess important neuroprotective effects against rotenone-induced DA neuronal damage. Naturally occurring antioxidants reduce the risk of neurodegenerative diseases. In addition, carnosol and carnosic acid promoted the synthesis of nerve growth factor in glial cells. Carnosol-mediated neuroprotection in DA neurons is involved in the attenuation of caspase-3 activity, which was induced by rotenone. Furthermore, carnosol-mediated tyrosine hydroxylase (TH) increase, which is dependent on the Raf-mitogen-activated protein kinase (MEK)-extracellular signal-regulated kinase (ERK)1/2 signaling pathway, is responsible for the neuroprotection in SN4741 DA cells. (PMID: 17047462 ). Carnosol, a phenolic diterpene compound of the labiate herbs rosemary and sage, is an activator of the human peroxisome proliferator-activated receptor gamma (PPARgamma), a ligand activated transcription factor, belonging to the metazoan family of nuclear hormone receptors. Activation of PPARgamma increases the transcription of enzymes involved in primary metabolism, leading to lower blood levels of fatty acids and glucose. Hence, PPARgamma represents the major target for the glitazone type of drugs currently being used clinically for the treatment of type 2 diabetes. (PMID: 16858665 ).

Structure

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

HMDB0002121
     RDKit          3D
Carnosol
 50 53  0  0  0  0  0  0  0  0999 V2000
    4.7420    0.8444    1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4596   -0.1855    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389    0.5995   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867   -0.3452    0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184    0.7070   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9749    0.4957   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -0.6933   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153   -1.7175    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583   -2.8907    0.3908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515   -1.5541    0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -2.5915    1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1249   -0.6600   -0.7415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8376   -1.8580   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.7107   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341   -0.3394   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    0.6404    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6145    2.0166    0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    0.3894    1.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615    0.6060    0.0253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1798    1.7734   -0.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1394    1.4503   -1.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2828    0.5580   -2.6595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508   -0.4251   -2.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9017   -1.0675   -2.9501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533    1.0391    2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1293    1.8031    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5665    0.3871    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816   -1.1097    0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790    1.6541   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0441    0.4587   -1.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993    0.2582   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7448    1.6431   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -3.7205    0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814   -2.5068    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -2.7041   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989   -2.0496    0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8269   -2.4538    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848   -2.1339   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1811    0.0971   -1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891   -0.4303    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9504    2.7807    0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5728    2.0223    0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831    2.2577   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    1.3061    2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686    0.1566    2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -0.3627    2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9523    0.7417    0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    1.7800   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334    2.7497   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161    2.2938   -1.9337 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  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 10  4  1  0
 19 12  1  0
 21  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 21 50  1  6
M  END

carnosol
  Mrv1572001071617062D          

 24 27  0  0  1  0            999 V2000
    6.5770   -0.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272    0.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8251    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3888    0.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1481    1.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3660    1.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8244    0.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651    0.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8473    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2613   -0.6798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8882    0.8322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2818    0.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4707    0.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4984    2.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3587    1.5040    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9279    2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526    2.1165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4092    1.3662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5390    0.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9800   -0.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 21 20  1  1  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  6  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002121

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC2=C(C(O)=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1

> <INCHI_KEY>
XUSYGBPHQBWGAD-PJSUUKDQSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.425804880412805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
4.575294142333332

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.853185894259425

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.18507529801697

> <JCHEM_PKA_STRONGEST_BASIC>
-6.051906167096008

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
91.42909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,10S)-3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002121
     RDKit          3D
Carnosol
 50 53  0  0  0  0  0  0  0  0999 V2000
    4.7420    0.8444    1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4596   -0.1855    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389    0.5995   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867   -0.3452    0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184    0.7070   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9749    0.4957   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -0.6933   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153   -1.7175    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583   -2.8907    0.3908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515   -1.5541    0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -2.5915    1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1249   -0.6600   -0.7415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8376   -1.8580   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.7107   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341   -0.3394   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    0.6404    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6145    2.0166    0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    0.3894    1.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615    0.6060    0.0253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1798    1.7734   -0.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1394    1.4503   -1.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2828    0.5580   -2.6595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508   -0.4251   -2.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9017   -1.0675   -2.9501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533    1.0391    2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1293    1.8031    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5665    0.3871    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816   -1.1097    0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790    1.6541   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0441    0.4587   -1.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993    0.2582   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7448    1.6431   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -3.7205    0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814   -2.5068    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -2.7041   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989   -2.0496    0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8269   -2.4538    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848   -2.1339   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1811    0.0971   -1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891   -0.4303    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9504    2.7807    0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5728    2.0223    0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831    2.2577   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    1.3061    2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686    0.1566    2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -0.3627    2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9523    0.7417    0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    1.7800   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334    2.7497   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161    2.2938   -1.9337 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  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 10  4  1  0
 19 12  1  0
 21  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 21 50  1  6
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: carnosol                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      12.277  -0.531   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.624   0.894   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.740   1.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.059   1.205   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.610   2.632   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.150   2.956   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.139   1.854   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.588   0.427   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.366  -0.827   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.048   0.103   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.821  -1.269   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.391   1.553   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.259   0.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.745   0.121   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.071   1.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.825   2.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.355   3.422   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.797   4.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.403   2.807   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.465   3.989   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.005   3.951   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.364   2.550   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.606   0.888   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.429  -0.711   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13   19   23                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    6   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   12   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0002121
HETATM    1  C1  UNL     1       4.742   0.844   1.424  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.460  -0.186   0.325  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.939   0.600  -0.973  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.987  -0.345   0.140  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.318   0.707  -0.450  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.975   0.496  -0.740  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.359  -0.693  -0.449  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.015  -1.718   0.125  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.358  -2.891   0.391  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.352  -1.554   0.429  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.060  -2.591   1.031  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.125  -0.660  -0.741  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.838  -1.858  -0.302  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.315  -1.711  -0.467  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.834  -0.339  -0.320  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.976   0.640   0.403  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.614   2.017   0.181  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.129   0.389   1.898  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.562   0.606   0.025  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.180   1.773  -0.897  1.00  0.00           C  
HETATM   21  C19 UNL     1       0.139   1.450  -1.550  1.00  0.00           C  
HETATM   22  O3  UNL     1      -0.283   0.558  -2.659  1.00  0.00           O  
HETATM   23  C20 UNL     1      -1.151  -0.425  -2.201  1.00  0.00           C  
HETATM   24  O4  UNL     1      -1.902  -1.067  -2.950  1.00  0.00           O  
HETATM   25  H1  UNL     1       3.853   1.039   2.053  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.129   1.803   1.054  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.566   0.387   2.045  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.982  -1.110   0.369  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.679   1.654  -0.767  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.044   0.459  -1.085  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.399   0.258  -1.849  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.745   1.643  -0.688  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.709  -3.721   0.804  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.981  -2.507   1.325  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.485  -2.704  -0.894  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.699  -2.050   0.797  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.827  -2.454   0.249  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.585  -2.134  -1.470  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.181   0.097  -1.269  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.789  -0.430   0.292  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.950   2.781   0.623  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.573   2.022   0.709  1.00  0.00           H  
HETATM   43  H19 UNL     1      -3.783   2.258  -0.864  1.00  0.00           H  
HETATM   44  H20 UNL     1      -3.490   1.306   2.443  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.169   0.157   2.381  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.910  -0.363   2.097  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.952   0.742   0.929  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.974   1.780  -1.716  1.00  0.00           H  
HETATM   49  H25 UNL     1      -1.233   2.750  -0.415  1.00  0.00           H  
HETATM   50  H26 UNL     1       0.716   2.294  -1.934  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   28
CONECT    3   29   30   31
CONECT    4    5    5   10
CONECT    5    6   32
CONECT    6    7    7   21
CONECT    7    8   12
CONECT    8    9   10   10
CONECT    9   33
CONECT   10   11
CONECT   11   34
CONECT   12   13   19   23
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   39   40
CONECT   16   17   18   19
CONECT   17   41   42   43
CONECT   18   44   45   46
CONECT   19   20   47
CONECT   20   21   48   49
CONECT   21   22   50
CONECT   22   23
CONECT   23   24   24
END

HMDB0002121
     RDKit          3D
Carnosol
 50 53  0  0  0  0  0  0  0  0999 V2000
    4.7420    0.8444    1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4596   -0.1855    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389    0.5995   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867   -0.3452    0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184    0.7070   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9749    0.4957   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -0.6933   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153   -1.7175    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583   -2.8907    0.3908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515   -1.5541    0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -2.5915    1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1249   -0.6600   -0.7415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8376   -1.8580   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.7107   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341   -0.3394   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    0.6404    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6145    2.0166    0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    0.3894    1.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615    0.6060    0.0253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1798    1.7734   -0.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1394    1.4503   -1.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2828    0.5580   -2.6595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508   -0.4251   -2.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9017   -1.0675   -2.9501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8533    1.0391    2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1293    1.8031    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5665    0.3871    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816   -1.1097    0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790    1.6541   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0441    0.4587   -1.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993    0.2582   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7448    1.6431   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -3.7205    0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814   -2.5068    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -2.7041   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989   -2.0496    0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8269   -2.4538    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5848   -2.1339   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1811    0.0971   -1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891   -0.4303    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9504    2.7807    0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5728    2.0223    0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831    2.2577   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    1.3061    2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686    0.1566    2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -0.3627    2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9523    0.7417    0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    1.7800   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334    2.7497   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161    2.2938   -1.9337 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  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 10  4  1  0
 19 12  1  0
 21  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 21 50  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,4,9,10,10AS-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4ar-(epoxymethano)phenanthren-12-one	HMDB

Chemical Formula

C₂₀H₂₆O₄

Average Molecular Weight

330.424

Monoisotopic Molecular Weight

330.183109317

IUPAC Name

(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

Traditional Name

(1R,8S,10S)-3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

CAS Registry Number

5957-80-2

SMILES

CC(C)C1=CC2=C(C(O)=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O

InChI Identifier

InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1

InChI Key

XUSYGBPHQBWGAD-PJSUUKDQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Phenanthrene
Benzopyran
Isochromane
2-benzopyran
Tetralin
1-hydroxy-4-unsubstituted benzenoid
Delta valerolactone
Delta_valerolactone
Benzenoid
Oxane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

diterpenoid (CHEBI:3429 )
Abietanes (C09069 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002121)
Membrane (HMDB: HMDB0002121)

Source

Exogenous

Exogenous (HMDB: HMDB0002121)

Herbs and Spices (FooDB: FOOD00866)

Tea

Process

Not Available

Role

Industrial applicationBiological role

Modulator

Inhibitor

EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (HMDB: HMDB0002121)

Enzyme inhibitor

Protease inhibitor (HMDB: HMDB0002121)
5-lipoxygenase inhibitor (HMDB: HMDB0002121)
Cyclooxygenase inhibitor (HMDB: HMDB0002121)
Ornithine-decarboxylase inhibitor (HMDB: HMDB0002121)

Anti hepatotoxic (HMDB: HMDB0002121)
Anti HIV (HMDB: HMDB0002121)
Anti-inflammatory (HMDB: HMDB0002121)
Anti lipoperoxidant (HMDB: HMDB0002121)
Anti mutagenic (HMDB: HMDB0002121)
Anti radicular (HMDB: HMDB0002121)
Candidicide (HMDB: HMDB0002121)
Metal chelator (HMDB: HMDB0002121)
Quinone-reductase inducer (HMDB: HMDB0002121)

Physical Properties

State

Solid

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	0.04 g/L	ALOGPS
logP	4.35	ALOGPS
logP	4.58	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.43 m³·mol⁻¹	ChemAxon
Polarizability	36.43 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]+	177.949	31661259
DarkChem	[M-H]-	172.678	31661259
DeepCCS	[M-2H]-	217.3	30932474
DeepCCS	[M+Na]+	192.911	30932474
AllCCS	[M+H]+	178.9	32859911
AllCCS	[M+H-H2O]+	175.9	32859911
AllCCS	[M+NH4]+	181.6	32859911
AllCCS	[M+Na]+	182.4	32859911
AllCCS	[M-H]-	187.9	32859911
AllCCS	[M+Na-2H]-	187.9	32859911
AllCCS	[M+HCOO]-	188.1	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. Predicted by Afia on May 17, 2022.	8.13 minutes	32390414
Predicted by Siyang on May 30, 2022	18.0175 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.92 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2800.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	457.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	220.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	924.5 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	1043.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1518.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	579.5 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	1748.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	521.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	505.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	317.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	312.6 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carnosol	CC(C)C1=CC2=C(C(O)=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	3609.7	Standard polar	33892256
Carnosol	CC(C)C1=CC2=C(C(O)=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	2587.5	Standard non polar	33892256
Carnosol	CC(C)C1=CC2=C(C(O)=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	2895.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carnosol,1TMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	2655.7	Semi standard non polar	33892256
Carnosol,1TMS,isomer #2	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	2645.2	Semi standard non polar	33892256
Carnosol,2TMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	2601.8	Semi standard non polar	33892256
Carnosol,1TBDMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	2878.4	Semi standard non polar	33892256
Carnosol,1TBDMS,isomer #2	CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	2888.7	Semi standard non polar	33892256
Carnosol,2TBDMS,isomer #1	CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O	3021.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carnosol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00s9-6098000000-26001744db43187e05ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carnosol GC-MS (2 TMS) - 70eV, Positive	splash10-0159-2000900000-f32732b369e071f050f3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carnosol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 10V, Positive-QTOF	splash10-001i-0019000000-08dcb84c59b0d280b13f	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 20V, Positive-QTOF	splash10-001r-6097000000-b2894527af41d8c29ad8	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 40V, Positive-QTOF	splash10-067l-9041000000-63e8a7af26ccd9f942f7	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 10V, Negative-QTOF	splash10-004i-0009000000-a5b241b8344c36c2f0bf	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 20V, Negative-QTOF	splash10-004i-0019000000-e7accf1a4d2c8280c2f4	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 40V, Negative-QTOF	splash10-03y0-1093000000-a5175230ca7dfd038446	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 10V, Positive-QTOF	splash10-001i-0009000000-17bca84b51a62d59a8e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 20V, Positive-QTOF	splash10-001i-0009000000-1287a0e9fae051b5c6df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 40V, Positive-QTOF	splash10-014i-5092000000-c5b1e9ba0e2ffa3d96cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 10V, Negative-QTOF	splash10-004i-0009000000-f547833d1942b8c5fe90	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 20V, Negative-QTOF	splash10-004i-0009000000-590265a71dc7bb39a643	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carnosol 40V, Negative-QTOF	splash10-0udi-1090000000-c84740a4e1e940011547	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carnosol

METLIN ID

Not Available

PubChem Compound

442009

PDB ID

Not Available

ChEBI ID

468005

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1598201

References

Synthesis Reference

Luxenburger, Andreas. The synthesis of carnosol derivatives. Tetrahedron (2003), 59(18), 3297-3305

Material Safety Data Sheet (MSDS)

Not Available

General References

Kim SJ, Kim JS, Cho HS, Lee HJ, Kim SY, Kim S, Lee SY, Chun HS: Carnosol, a component of rosemary (Rosmarinus officinalis L.) protects nigral dopaminergic neuronal cells. Neuroreport. 2006 Nov 6;17(16):1729-33. [PubMed:17047462 ]
Rau O, Wurglics M, Paulke A, Zitzkowski J, Meindl N, Bock A, Dingermann T, Abdel-Tawab M, Schubert-Zsilavecz M: Carnosic acid and carnosol, phenolic diterpene compounds of the labiate herbs rosemary and sage, are activators of the human peroxisome proliferator-activated receptor gamma. Planta Med. 2006 Aug;72(10):881-7. Epub 2006 Jul 20. [PubMed:16858665 ]

Showing metabocard for Carnosol (HMDB0002121)

MOL for HMDB0002121 (Carnosol)

3D MOL for HMDB0002121 (Carnosol)

3D SDF for HMDB0002121 (Carnosol)

3D-SDF for HMDB0002121 (Carnosol)

PDB for HMDB0002121 (Carnosol)

3D PDB for HMDB0002121 (Carnosol)

SMILES for HMDB0002121 (Carnosol)

INCHI for HMDB0002121 (Carnosol)

Structure for HMDB0002121 (Carnosol)

3D Structure for HMDB0002121 (Carnosol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra