Np mrd loader

Showing NP-Card for Chaulmoogric acid (NP0050648)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-27 22:00:27 UTC
Updated at2022-04-27 22:00:27 UTC
NP-MRD IDNP0050648
Secondary Accession NumbersNone
Natural Product Identification
Common NameChaulmoogric acid
Description(R)-chaulmoogric acid, also known as acide (R)-chaulmoogrique or (R)-chaulmoograte, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Chaulmoogric acid is found in Caloncoba echinata, Carpotroche brasiliensis, Hydnocarpus anthelminticus and Hydnocarpus wightiana. Chaulmoogric acid was first documented in 2010 (PMID: 20730968). Based on a literature review very few articles have been published on (R)-chaulmoogric acid (PMID: 27280046).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050648 (Chaulmoogric acid)


  Mrv1652304282200002D          

 20 20  0  0  1  0            999 V2000
    7.4110   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6966   -7.1890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4110   -5.9515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1255   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8400   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5544   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2689   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9834   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4123   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1268   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5557   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2702   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9847   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6991   -7.1890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4528   -6.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0049   -7.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924   -8.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7854   -8.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
M  END
Download

3D MOL for NP0050648 (Chaulmoogric acid)

Download
3D SDF for NP0050648 (Chaulmoogric acid)

  Mrv1652304282200002D          

 20 20  0  0  1  0            999 V2000
    7.4110   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6966   -7.1890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4110   -5.9515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1255   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8400   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5544   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2689   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9834   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4123   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1268   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5557   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2702   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9847   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6991   -7.1890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4528   -6.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0049   -7.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924   -8.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7854   -8.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCCCCCCCCCCC[C@@H]1CCC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O2/c19-18(20)16-10-8-6-4-2-1-3-5-7-9-13-17-14-11-12-15-17/h11,14,17H,1-10,12-13,15-16H2,(H,19,20)/t17-/m0/s1

> <INCHI_KEY>
XMVQWNRDPAAMJB-KRWDZBQOSA-N

> <FORMULA>
C18H32O2

> <MOLECULAR_WEIGHT>
280.452

> <EXACT_MASS>
280.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.460017121913964

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-[(1R)-cyclopent-2-en-1-yl]tridecanoic acid

> <ALOGPS_LOGP>
7.24

> <JCHEM_LOGP>
6.162522979666667

> <ALOGPS_LOGS>
-6.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
85.54759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-chaulmoograsauere

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050648 (Chaulmoogric acid)
Download
PDB for NP0050648 (Chaulmoogric acid)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.834 -12.649   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.500 -13.419   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.834 -11.109   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.168 -13.419   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.501 -12.649   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.835 -13.419   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.169 -12.649   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.502 -13.419   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.836 -12.649   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.170 -13.419   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.503 -12.649   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.837 -13.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.171 -12.649   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.504 -13.419   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.838 -12.649   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.172 -13.419   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.579 -12.793   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.609 -13.937   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.839 -15.271   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.333 -14.951   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

Download
3D PDB for NP0050648 (Chaulmoogric acid)
Download
SMILES for NP0050648 (Chaulmoogric acid)
OC(=O)CCCCCCCCCCCC[C@@H]1CCC=C1
Download
INCHI for NP0050648 (Chaulmoogric acid)
InChI=1S/C18H32O2/c19-18(20)16-10-8-6-4-2-1-3-5-7-9-13-17-14-11-12-15-17/h11,14,17H,1-10,12-13,15-16H2,(H,19,20)/t17-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
(+)-ChaulmoograsauereChEBI
(R)-13-(Cyclopent-2-en-1-yl)tridecanoic acidChEBI
(R)-2-Cyclopentene-1-tridecanoic acidChEBI
13-(R)-Cyclopent-2-enyl-tridecanoic acidChEBI
13-(R)-Cyclopent-2-enyl-tridecansaeureChEBI
13-[(R)-Cyclopent-2-enyl]-tridecanoic acidChEBI
13-[(R)-Cyclopent-2-enyl]-tridecansauereChEBI
Acide (R)-chaulmoogriqueChEBI
Acido (R)-chaulmogricoChEBI
(R)-13-(Cyclopent-2-en-1-yl)tridecanoateGenerator
(R)-2-Cyclopentene-1-tridecanoateGenerator
13-(R)-Cyclopent-2-enyl-tridecanoateGenerator
13-[(R)-Cyclopent-2-enyl]-tridecanoateGenerator
(R)-ChaulmoograteGenerator
Chaulmoogric acid sodium saltMeSH
Chemical FormulaC18H32O2
Average Mass280.4520 Da
Monoisotopic Mass280.24023 Da
IUPAC Name13-[(1R)-cyclopent-2-en-1-yl]tridecanoic acid
Traditional Name(+)-chaulmoograsauere
CAS Registry NumberNot Available
SMILES
OC(=O)CCCCCCCCCCCC[C@@H]1CCC=C1
InChI Identifier
InChI=1S/C18H32O2/c19-18(20)16-10-8-6-4-2-1-3-5-7-9-13-17-14-11-12-15-17/h11,14,17H,1-10,12-13,15-16H2,(H,19,20)/t17-/m0/s1
InChI KeyXMVQWNRDPAAMJB-KRWDZBQOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Caloncoba echinataLOTUS Database
Carpotroche brasiliensisLOTUS Database
Hydnocarpus anthelminticusPlant
Hydnocarpus wightianaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentLong-chain fatty acids  
Alternative Parents
Substituents
  • Long-chain fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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
logP7.24ALOGPS
logP6.16ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity85.55 m³·mol⁻¹ChemAxon
Polarizability36.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12302887  
PDB IDNot Available
ChEBI ID61389  
Good Scents IDNot Available
References
General References
  1. Firashathulla S, Inamdar MN, Rafiq M, Viswanatha GL, Sharath Kumar LM, Babu UV, Ramakrishnan S, Paramesh R: IM-133N - A Useful Herbal Combination for Eradicating Disease-triggering Pathogens in Mice via Immunotherapeutic Mechanisms. J Pharmacopuncture. 2016 Mar;19(1):21-7. doi: 10.3831/KPI.2016.19.003. [PubMed:27280046  ] 
  2. Wang JF, Dai HQ, Wei YL, Zhu HJ, Yan YM, Wang YH, Long CL, Zhong HM, Zhang LX, Cheng YX: Antituberculosis agents and an inhibitor of the para-aminobenzoic acid biosynthetic pathway from Hydnocarpus anthelminthica seeds. Chem Biodivers. 2010 Aug;7(8):2046-53. doi: 10.1002/cbdv.201000072. [PubMed:20730968  ]