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Showing NP-Card for Carnosic acid (NP0048443)

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Record Information
Version2.0
Created at2022-03-17 20:56:33 UTC
Updated at2022-03-17 20:56:33 UTC
NP-MRD IDNP0048443
Secondary Accession NumbersNone
Natural Product Identification
Common NameCarnosic acid
DescriptionCarnosic acid, also known as carnosate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Carnosic acid is found in Hypis dilatata, Lepechinia hastata, Lepechinia salviae, Nocardia sp. NRRL5646, Rosamarinus officinalis, Salvia aurea, Salvia apiana, Salvia canariensis, Salvia columbariae, Salvia mellifera, Salvia munzii, Salvia pachyphylla and Salvia tomentosa. Carnosic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048443 (Carnosic acid)


  Mrv1652305221920282D          

 24 26  0  0  0  0            999 V2000
    7.4106   -1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3778   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537    0.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476    0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619   -1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4747    0.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6499    0.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0331   -0.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7283   -0.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9818   -0.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035   -0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570   -0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2539   -0.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075   -0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7610   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8534   -1.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1114   -1.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6827   -0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1897   -2.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402   -2.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9362   -1.4921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154   -2.2347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20  9  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  2  0  0  0  0
 24 18  1  0  0  0  0
M  END
Download

3D MOL for NP0048443 (Carnosic acid)

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3D SDF for NP0048443 (Carnosic acid)

  Mrv1652305221920282D          

 24 26  0  0  0  0            999 V2000
    7.4106   -1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3778   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537    0.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476    0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619   -1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4747    0.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6499    0.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0331   -0.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7283   -0.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9818   -0.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035   -0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570   -0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2539   -0.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075   -0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7610   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8534   -1.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1114   -1.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291   -0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6827   -0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1897   -2.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5402   -2.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9362   -1.4921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154   -2.2347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20  9  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  2  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(O)C(O)=C2C(CCC3C(C)(C)CCCC23C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)

> <INCHI_KEY>
QRYRORQUOLYVBU-UHFFFAOYSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.4339

> <EXACT_MASS>
332.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.27944937558823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
5.141634084666667

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.551732124188296

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.292945414120731

> <JCHEM_PKA_STRONGEST_BASIC>
-6.00916058522994

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
93.40579999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carnosic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048443 (Carnosic acid)
Download
PDB for NP0048443 (Carnosic acid)
HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      13.833  -2.679   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.772  -0.013   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.767   1.298   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.076   0.269   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.595  -2.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.353   1.197   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.813   1.162   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.795  -1.575   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.135  -2.856   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.693  -0.083   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.033  -1.364   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.153  -0.119   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.493  -1.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.074  -0.189   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.414  -1.469   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.754  -2.750   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.060  -3.420   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.675  -2.820   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.534  -0.224   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.874  -1.505   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.554  -4.066   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.475  -4.136   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.214  -2.785   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.935  -4.171   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    8    9                                                       
CONECT    6    7   12                                                       
CONECT    7    6   14                                                       
CONECT    8    5   19                                                       
CONECT    9    5   20                                                       
CONECT   10   12   13                                                       
CONECT   11    1    2   13                                                  
CONECT   12    6   10   15                                                  
CONECT   13   10   11   16                                                  
CONECT   14    7   19   20                                                  
CONECT   15   12   17   20                                                  
CONECT   16   13   17   21                                                  
CONECT   17   15   16   22                                                  
CONECT   18   20   23   24                                                  
CONECT   19    3    4    8   14                                             
CONECT   20    9   14   15   18                                             
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   18                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

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3D PDB for NP0048443 (Carnosic acid)
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SMILES for NP0048443 (Carnosic acid)
CC(C)C1=C(O)C(O)=C2C(CCC3C(C)(C)CCCC23C(O)=O)=C1
Download
INCHI for NP0048443 (Carnosic acid)
InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)
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View in JSmol
Synonyms
ValueSource
CarnosateGenerator
Chemical FormulaC20H28O4
Average Mass332.4339 Da
Monoisotopic Mass332.19876 Da
IUPAC Name5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid
Traditional Namecarnosic acid
CAS Registry Number3650-09-7
SMILES
CC(C)C1=C(O)C(O)=C2C(CCC3C(C)(C)CCCC23C(O)=O)=C1
InChI Identifier
InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)
InChI KeyQRYRORQUOLYVBU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Carum carviFooDB
Cinnamomum verumFooDB
Cuminum cyminumFooDB
Hypis dilatata-
Illicium verumFooDB
Laurus nobilis L.FooDB
Lepechinia hastataLOTUS Database
Lepechinia salviaeLOTUS Database
Myristica fragransFooDB
Nocardia sp. NRRL5646Bacteria
Origanum X majoricumFooDB
Piper nigrum L.FooDB
Rosamarinus officinalis-
Salvia africana-luteaLOTUS Database
Salvia apianaLOTUS Database
Salvia canariensisLOTUS Database
Salvia columbariaeLOTUS Database
Salvia melliferaLOTUS Database
Salvia munziiLOTUS Database
Salvia officinalisFooDB
Salvia pachyphyllaPlant
Salvia rosmarinusFooDB
Salvia tomentosaLOTUS Database
Syzygium aromaticumFooDB
Thymus vulgarisFooDB
Zingiber officinaleFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentDiterpenoids  
Alternative Parents
Substituents
  • Abietane diterpenoid
    • 

  • Diterpenoid
    • 

  • Hydrophenanthrene
    • 

  • Phenanthrene
    • 

  • 1-naphthalenecarboxylic acid
    • 

  • 1-naphthalenecarboxylic acid or derivatives
    • 

  • Tetralin
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.16ALOGPS
logP5.14ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.29ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.41 m³·mol⁻¹ChemAxon
Polarizability37.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014905  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarnosic acid  
METLIN IDNot Available
PubChem Compound5024746  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available