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Showing NP-Card for Kaurenoic acid (NP0049896)

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Record Information
Version2.0
Created at2022-03-17 21:19:51 UTC
Updated at2022-03-17 21:19:51 UTC
NP-MRD IDNP0049896
Secondary Accession NumbersNone
Natural Product Identification
Common NameKaurenoic acid
DescriptionKaurenoic acid, also known as kaurenoate, belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Kaurenoic acid is found in Annona cherimola, Annona glabra, Annona senegalensis, Annona squamosa, Aralia cordata, Aspilia mossambicensis, Athrixia elata, Baccharis minutiflora, Baccharis ramosissima, Baccharis retusa, Bedfordia arborescens, Calocephalus knappii, Casearia corymbosa, Chrozophora oblongifolia, Copaifera paupera, Croton argyrophyllus, Dendroviguiera insignis, Eleutherococcus trifoliatus, Libanothamnus spectabilis, Espeletiopsis guacharaca, Filago congesta, Goyazianthus tetrastichus, Helianthus annuus, Helianthus debilis, Helianthus niveus, Helianthus petiolaris, Helianthus radula, Helianthus simulans, Helichrysum chionosphaerum, Ichthyothere terminalis, Iostephane heterophylla, Wollastonia biflora, Mikania hirsutissima, Mikania micrantha, Mikania vitifolia, Mitrephora celebica, Montanoa leucantha, Montanoa tomentosa, Nassauvia lagascae, Othonna sedifolia, Oyedaea verbesinoides, Ozothamnus diosmifolius, Ozothamnus retusus, Pappobolus stuebelii, Perymenium jelskii, Pleurothyrium cinereum, Pseudognaphalium oligandrum, Pteris haenkeana, Sagittaria trifolia, Smallanthus fruticosus, Smallanthus maculatus, Smallanthus sonchifolius, Smallanthus uvedalia, Solidago missouriensis, Solidago nemoralis, Solidago rugosa, Sphagneticola trilobata, Steiractinia sodiroi, Stevia lucida, Tithonia longiradiata, Viguiera cordifolia, Viguiera decurrens, Viguiera hypargyrea, Viguiera incana, Wedelia acapulcensis, Xylopia aethiopica and Xylopia frutescens. Kaurenoic acid is a weakly acidic compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049896 (Kaurenoic acid)


  Mrv0541 02241221572D          

 22 25  0  0  0  0            999 V2000
    1.1251   -0.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -1.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263   -2.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -1.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3490    0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    2.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1156    1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490    0.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704    1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5824    2.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477    2.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924    0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924   -0.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1937   -0.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2803   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803   -2.7555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043   -2.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937   -2.9108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 17  1  0  0  0  0
  4 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
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3D MOL for NP0049896 (Kaurenoic acid)

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3D SDF for NP0049896 (Kaurenoic acid)

  Mrv0541 02241221572D          

 22 25  0  0  0  0            999 V2000
    1.1251   -0.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -1.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263   -2.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -1.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3490    0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    2.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1156    1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490    0.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704    1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5824    2.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477    2.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924    0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924   -0.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1937   -0.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2803   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803   -2.7555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043   -2.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937   -2.9108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 17  1  0  0  0  0
  4 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)

> <INCHI_KEY>
NIKHGUQULKYIGE-UHFFFAOYSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.451

> <EXACT_MASS>
302.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.26195420899826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
4.8078307643333345

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.839023750520022

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.36359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049896 (Kaurenoic acid)
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PDB for NP0049896 (Kaurenoic 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       2.100  -1.666   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.100  -3.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.796  -3.839   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.651  -3.259   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.101  -2.969   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.651   0.796   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.810   1.811   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.810   3.405   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.362   3.984   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.216   2.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.651   1.665   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.811   2.679   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.087   4.129   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.956   5.433   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.666   0.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.666  -0.941   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.362  -1.666   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.941  -0.796   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.390  -0.218   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.390  -5.144   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.941  -4.709   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.362  -5.433   0.000  0.00  0.00           O+0
CONECT    1    2   18                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   17   21                                             
CONECT    5    4                                                            
CONECT    6    7   11   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10   12   15                                             
CONECT   12   11   13                                                       
CONECT   13    9   12   14                                                  
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17    4   16   18                                                  
CONECT   18    1    6   17   19                                             
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21    4   20   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

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3D PDB for NP0049896 (Kaurenoic acid)
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SMILES for NP0049896 (Kaurenoic acid)
CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3)C(O)=O
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INCHI for NP0049896 (Kaurenoic acid)
InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)
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Synonyms
ValueSource
KaurenoateGenerator
ent-Kaur-16-en-18-Oic acidMeSH
Kaur-16-en-18-Oic acidMeSH
3beta-Hydroxy-kaurenoic acidMeSH
Chemical FormulaC20H30O2
Average Mass302.4510 Da
Monoisotopic Mass302.22458 Da
IUPAC Name5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
Traditional Name5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
CAS Registry Number6730-83-2
SMILES
CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3)C(O)=O
InChI Identifier
InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)
InChI KeyNIKHGUQULKYIGE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annona cherimolaLOTUS Database
Annona glabraLOTUS Database
Annona senegalensisLOTUS Database
Annona squamosaLOTUS Database
Aralia cordataLOTUS Database
Aspilia mossambicensisLOTUS Database
Athrixia elataLOTUS Database
Baccharis minutifloraLOTUS Database
Baccharis ramosissimaLOTUS Database
Baccharis retusaLOTUS Database
Bedfordia arborescensLOTUS Database
Calocephalus knappiiLOTUS Database
Casearia corymbosaLOTUS Database
Chrozophora oblongifoliaLOTUS Database
Copaifera pauperaLOTUS Database
Croton argyrophyllusLOTUS Database
Dendroviguiera insignisLOTUS Database
Eleutherococcus trifoliatusLOTUS Database
Espeletia spectabilisLOTUS Database
Espeletiopsis guacharacaLOTUS Database
Filago congestaLOTUS Database
Goyazianthus tetrastichusLOTUS Database
Helianthus annuusLOTUS Database
Helianthus annuus L.FooDB
Helianthus debilisLOTUS Database
Helianthus niveusLOTUS Database
Helianthus petiolarisLOTUS Database
Helianthus radulaLOTUS Database
Helianthus simulansLOTUS Database
Helichrysum chionosphaerumLOTUS Database
Ichthyothere terminalisLOTUS Database
Iostephane heterophyllaLOTUS Database
Melanthera bifloraLOTUS Database
Mikania hirsutissimaLOTUS Database
Mikania micranthaLOTUS Database
Mikania vitifoliaLOTUS Database
Mitrephora celebicaLOTUS Database
Montanoa leucanthaLOTUS Database
Montanoa tomentosaLOTUS Database
Nassauvia lagascaeLOTUS Database
Othonna sedifoliaLOTUS Database
Oyedaea verbesinoidesLOTUS Database
Ozothamnus diosmifoliusLOTUS Database
Ozothamnus retususLOTUS Database
Pappobolus stuebeliiLOTUS Database
Perymenium jelskiiLOTUS Database
Pleurothyrium cinereumLOTUS Database
Pseudognaphalium oligandrumLOTUS Database
Pteris haenkeanaLOTUS Database
Sagittaria trifoliaLOTUS Database
Smallanthus fruticosusLOTUS Database
Smallanthus maculatusLOTUS Database
Smallanthus sonchifoliusLOTUS Database
Smallanthus uvedaliaLOTUS Database
Solidago missouriensisLOTUS Database
Solidago nemoralisLOTUS Database
Solidago rugosaLOTUS Database
Sphagneticola trilobataLOTUS Database
Steiractinia sodiroiLOTUS Database
Stevia lucidaLOTUS Database
Tithonia longiradiataLOTUS Database
Viguiera cordifoliaLOTUS Database
Viguiera decurrensLOTUS Database
Viguiera hypargyreaLOTUS Database
Viguiera incanaLOTUS Database
Wedelia acapulcensisLOTUS Database
Xylopia aethiopicaLOTUS Database
Xylopia frutescensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentKaurane diterpenoids  
Alternative Parents
Substituents
  • Kaurane diterpenoid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic 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
logP4.13ALOGPS
logP4.81ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity87.36 m³·mol⁻¹ChemAxon
Polarizability35.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021671  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound433869  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available