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Showing NP-Card for Carnosolic acid (NP0047002)

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Record Information
Version2.0
Created at2022-03-17 20:33:00 UTC
Updated at2022-03-17 20:33:00 UTC
NP-MRD IDNP0047002
Secondary Accession NumbersNone
Natural Product Identification
Common NameCarnosolic acid
DescriptionCarnosolic acid, also known as carnosolate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Carnosolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047002 (Carnosolic acid)


  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
Download

3D MOL for NP0047002 (Carnosolic acid)

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3D SDF for NP0047002 (Carnosolic acid)

  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>
NP0047002

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

Download
3D-SDF for NP0047002 (Carnosolic acid)
Download
PDB for NP0047002 (Carnosolic acid)
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

Download
3D PDB for NP0047002 (Carnosolic acid)
Download
SMILES for NP0047002 (Carnosolic acid)
CC(C)C1=CC2=C(C(O)=C1O)C1(CCCC(C)(C)C1CC2O)C(O)=O
Download
INCHI for NP0047002 (Carnosolic acid)
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)
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View in JSmol
Synonyms
ValueSource
CarnosolateGenerator
Chemical FormulaC20H28O5
Average Mass348.4333 Da
Monoisotopic Mass348.19367 Da
IUPAC Name5,6,9-trihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid
Traditional Name5,6,9-trihydroxy-7-isopropyl-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
CAS Registry NumberNot 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 KeyXMKKZBYHMFTMOJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Salvia officinalisFooDB
Salvia rosmarinusFooDB
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
    • 

  • 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 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
logP2.96ALOGPS
logP3.91ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.92 m³·mol⁻¹ChemAxon
Polarizability37.93 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006923  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11566445  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available