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Showing NP-Card for Carnosic acid 12-methyl ether (NP0047014)

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Record Information
Version2.0
Created at2022-03-17 20:33:13 UTC
Updated at2022-03-17 20:33:13 UTC
NP-MRD IDNP0047014
Secondary Accession NumbersNone
Natural Product Identification
Common NameCarnosic acid 12-methyl ether
DescriptionCarnosic acid 12-methyl ether belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Carnosic acid 12-methyl ether is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047014 (Carnosic acid 12-methyl ether)


  Mrv0541 02241223372D          

 25 27  0  0  0  0            999 V2000
   -2.5003   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    1.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8243    1.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    1.9661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160   -2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2559   -2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    1.5536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  2  0  0  0  0
  9 10  2  0  0  0  0
 10 16  1  0  0  0  0
 10 23  1  0  0  0  0
 11 12  2  0  0  0  0
 12 25  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
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3D MOL for NP0047014 (Carnosic acid 12-methyl ether)

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3D SDF for NP0047014 (Carnosic acid 12-methyl ether)

  Mrv0541 02241223372D          

 25 27  0  0  0  0            999 V2000
   -2.5003   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    1.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8243    1.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567    1.9661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160   -2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2559   -2.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    0.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    1.5536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  2  0  0  0  0
  9 10  2  0  0  0  0
 10 16  1  0  0  0  0
 10 23  1  0  0  0  0
 11 12  2  0  0  0  0
 12 25  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047014

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(CCC3C2C(CCC3(C)C)C(O)=O)C=C1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-11(2)14-10-12-6-7-15-17(16(12)18(22)19(14)25-5)13(20(23)24)8-9-21(15,3)4/h10-11,13,15,17,22H,6-9H2,1-5H3,(H,23,24)

> <INCHI_KEY>
LGAMCBOKOMIWEL-UHFFFAOYSA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.4605

> <EXACT_MASS>
346.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.43515481725433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
5.0185329350000005

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.97606212050637

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.456658783417427

> <JCHEM_PKA_STRONGEST_BASIC>
-4.884428277822123

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
97.93570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-3,4,4a,9,10,10a-hexahydro-2H-phenanthrene-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047014 (Carnosic acid 12-methyl ether)
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PDB for NP0047014 (Carnosic acid 12-methyl ether)
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      -4.667  -2.489   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.667  -0.949   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.335  -0.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001  -0.949   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -2.489   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.666  -3.259   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.666  -2.489   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.666  -0.949   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.001  -0.180   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.001   1.360   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.667   2.130   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.335   1.360   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.539   2.643   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.666  -0.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.666   1.360   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.666   2.130   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.666   3.670   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.001   4.440   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.323  -4.440   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.335  -3.259   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.344  -4.440   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.667   1.360   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.333   2.130   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.333   3.670   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.335   2.900   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   16   23                                                  
CONECT   11   12                                                            
CONECT   12    3   11   25                                                  
CONECT   13   15                                                            
CONECT   14    4    8   15                                                  
CONECT   15   13   14   16                                                  
CONECT   16   10   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20    1    5   19   21                                             
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23   10   22   24                                                  
CONECT   24   23                                                            
CONECT   25   12                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

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3D PDB for NP0047014 (Carnosic acid 12-methyl ether)
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SMILES for NP0047014 (Carnosic acid 12-methyl ether)
COC1=C(O)C2=C(CCC3C2C(CCC3(C)C)C(O)=O)C=C1C(C)C
Download
INCHI for NP0047014 (Carnosic acid 12-methyl ether)
InChI=1S/C21H30O4/c1-11(2)14-10-12-6-7-15-17(16(12)18(22)19(14)25-5)13(20(23)24)8-9-21(15,3)4/h10-11,13,15,17,22H,6-9H2,1-5H3,(H,23,24)
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Synonyms
ValueSource
Carnosate 12-methyl etherGenerator
Chemical FormulaC21H30O4
Average Mass346.4605 Da
Monoisotopic Mass346.21441 Da
IUPAC Name5-hydroxy-6-methoxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4-carboxylic acid
Traditional Name5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-3,4,4a,9,10,10a-hexahydro-2H-phenanthrene-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C2=C(CCC3C2C(CCC3(C)C)C(O)=O)C=C1C(C)C
InChI Identifier
InChI=1S/C21H30O4/c1-11(2)14-10-12-6-7-15-17(16(12)18(22)19(14)25-5)13(20(23)24)8-9-21(15,3)4/h10-11,13,15,17,22H,6-9H2,1-5H3,(H,23,24)
InChI KeyLGAMCBOKOMIWEL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Salvia officinalisFooDB
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
    • 

  • Tetralin
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP4.16ALOGPS
logP5.02ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.94 m³·mol⁻¹ChemAxon
Polarizability39.44 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 IDFDB006989  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available