NP-MRD: Showing NP-Card for (4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid (NP0239680)

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Record Information

Version

2.0

Created at

2022-09-06 23:19:46 UTC

Updated at

2022-09-06 23:19:46 UTC

NP-MRD ID

NP0239680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid

Description

Canophyllic acid, also known as canophyllate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid is found in Calophyllum calaba, Calophyllum inophyllum and Semialarium mexicanum. (4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid was first documented in 2005 (PMID: 15468303). Based on a literature review a small amount of articles have been published on Canophyllic acid (PMID: 31391686) (PMID: 20188156) (PMID: 23083817).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201192D          

 33 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072201192D          

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    2.7770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0239680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H](O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@@]3(CC[C@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O3/c1-19-20(31)8-9-21-26(19,4)11-10-22-27(21,5)13-14-29(7)23-18-25(2,3)12-16-30(23,24(32)33)17-15-28(22,29)6/h19-23,31H,8-18H2,1-7H3,(H,32,33)/t19-,20-,21+,22-,23-,26+,27-,28+,29-,30-/m0/s1

> <INCHI_KEY>
SWXBCXVNBGHVGG-VKGQNDASSA-N

> <FORMULA>
C30H50O3

> <MOLECULAR_WEIGHT>
458.727

> <EXACT_MASS>
458.37599547

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
55.68153604144912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6aR,6bS,8aS,9R,10S,12aS,12bS,14aS,14bS)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-docosahydropicene-4a-carboxylic acid

> <JCHEM_LOGP>
6.922459184666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.215333803187104

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.681379261362774

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9550139976975874

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
132.8515

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6aR,6bS,8aS,9R,10S,12aS,12bS,14aS,14bS)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.206 -11.137   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.644  -7.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.076  -5.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.791  -6.610   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.574 -11.137   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.804 -12.471   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.114 -11.137   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9   10   29                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   27                                             
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   14   22   25                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   12   28   29                                             
CONECT   28   27                                                            
CONECT   29   27    8   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    7    2   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Canophyllate	Generator

Chemical Formula

C₃₀H₅₀O₃

Average Mass

458.7270 Da

Monoisotopic Mass

458.37600 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H](O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@@]3(CC[C@]12C)C(O)=O

InChI Identifier

InChI=1S/C30H50O3/c1-19-20(31)8-9-21-26(19,4)11-10-22-27(21,5)13-14-29(7)23-18-25(2,3)12-16-30(23,24(32)33)17-15-28(22,29)6/h19-23,31H,8-18H2,1-7H3,(H,32,33)/t19-,20-,21+,22-,23-,26+,27-,28+,29-,30-/m0/s1

InChI Key

SWXBCXVNBGHVGG-VKGQNDASSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Calophyllum calaba	LOTUS Database	35616633
Calophyllum inophyllum	LOTUS Database	35616633
Semialarium mexicanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

68027293

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12082783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Desai TH, Joshi SV: In silico evaluation of apoptogenic potential and toxicological profile of triterpenoids. Indian J Pharmacol. 2019 May-Jun;51(3):181-207. doi: 10.4103/ijp.IJP_90_18. [PubMed:31391686 ]
Li YZ, Li ZL, Yin SL, Shi G, Liu MS, Jing YK, Hua HM: Triterpenoids from Calophyllum inophyllum and their growth inhibitory effects on human leukemia HL-60 cells. Fitoterapia. 2010 Sep;81(6):586-9. doi: 10.1016/j.fitote.2010.02.005. Epub 2010 Feb 24. [PubMed:20188156 ]
Prasad J, Shrivastava A, Khanna AK, Bhatia G, Awasthi SK, Narender T: Antidyslipidemic and antioxidant activity of the constituents isolated from the leaves of Calophyllum inophyllum. Phytomedicine. 2012 Nov 15;19(14):1245-9. doi: 10.1016/j.phymed.2012.09.001. Epub 2012 Oct 16. [PubMed:23083817 ]
Laure F, Herbette G, Faure R, Bianchini JP, Raharivelomanana P, Fogliani B: Structures of new secofriedelane and friedelane acids from Calophyllum inophyllum of French Polynesia. Magn Reson Chem. 2005 Jan;43(1):65-8. doi: 10.1002/mrc.1476. [PubMed:15468303 ]
LOTUS database [Link]

Showing NP-Card for (4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid (NP0239680)

MOL for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

3D MOL for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

3D SDF for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

3D-SDF for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

PDB for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

3D PDB for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

SMILES for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

INCHI for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

Structure for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)

3D Structure for NP0239680 ((4as,6ar,6bs,8as,9r,10s,12as,12bs,14as,14bs)-10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid)