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Showing NP-Card for Elephantopin (NP0050274)

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Record Information
Version2.0
Created at2022-04-27 20:50:55 UTC
Updated at2022-04-27 20:50:55 UTC
NP-MRD IDNP0050274
Secondary Accession NumbersNone
Natural Product Identification
Common NameElephantopin
DescriptionElephantopin belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Thus, elephantopin is considered to be an isoprenoid. Elephantopin is found in Elephantopus elatus, Elephantopus mollis, Elephantopus nudatus and Orthopappus angustifolius. Elephantopin was first documented in 2014 (PMID: 22336595). Based on a literature review very few articles have been published on Elephantopin.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050274 (Elephantopin)


  Mrv1652304272222502D          

 26 29  0  0  1  0            999 V2000
    3.9019    2.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265    2.7439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    3.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6234    4.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193    3.0860    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6469    2.2615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4660    2.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    1.8731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4025    1.0486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7022    0.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743    1.0007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1735    0.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7373    1.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    1.5182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467    1.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911    3.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    3.4743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8637    4.2989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1358    4.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356    4.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    5.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803    5.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084    5.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    1.4848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387    0.3484    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
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  1  7  1  0  0  0  0
  6  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  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  9 25  1  0  0  0  0
  8 25  1  1  0  0  0
  9 26  1  1  0  0  0
M  END
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3D MOL for NP0050274 (Elephantopin)

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3D SDF for NP0050274 (Elephantopin)

  Mrv1652304272222502D          

 26 29  0  0  1  0            999 V2000
    3.9019    2.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265    2.7439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    3.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6234    4.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193    3.0860    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6469    2.2615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4660    2.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    1.8731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4025    1.0486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7022    0.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743    1.0007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1735    0.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7373    1.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    1.5182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467    1.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911    3.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    3.4743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8637    4.2989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1358    4.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356    4.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    5.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803    5.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084    5.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    1.4848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387    0.3484    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
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  1  7  1  0  0  0  0
  6  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  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  9 25  1  0  0  0  0
  8 25  1  1  0  0  0
  9 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050274

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C(=O)O[C@H]1CC2=C[C@@H](C[C@@]3(C)O[C@@H]3[C@H]3OC(=O)C(=C)[C@H]13)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O7/c1-8(2)16(20)24-12-6-10-5-11(23-18(10)22)7-19(4)15(26-19)14-13(12)9(3)17(21)25-14/h5,11-15H,1,3,6-7H2,2,4H3/t11-,12-,13+,14-,15+,19+/m0/s1

> <INCHI_KEY>
WIQOUTANBFOBPB-KIVXNUBRSA-N

> <FORMULA>
C19H20O7

> <MOLECULAR_WEIGHT>
360.362

> <EXACT_MASS>
360.120902984

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.54121321487544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,5R,6S,10R,11S)-3-methyl-9-methylidene-8,14-dioxo-4,7,15-trioxatetracyclo[11.2.1.0^{3,5}.0^{6,10}]hexadec-13(16)-en-11-yl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
2.3383250223333323

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.488289576502883

> <JCHEM_PKA_STRONGEST_BASIC>
-4.241429460123731

> <JCHEM_POLAR_SURFACE_AREA>
91.43

> <JCHEM_REFRACTIVITY>
87.9768

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,5R,6S,10R,11S)-3-methyl-9-methylidene-8,14-dioxo-4,7,15-trioxatetracyclo[11.2.1.0^{3,5}.0^{6,10}]hexadec-13(16)-en-11-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050274 (Elephantopin)
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PDB for NP0050274 (Elephantopin)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       7.284   5.070   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.823   5.122   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.337   6.285   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.764   7.765   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.889   5.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.941   4.221   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.470   4.007   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.300   3.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.351   1.957   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.044   1.143   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.685   1.868   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.191   1.498   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.376   2.805   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.163   2.834   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.275   4.132   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.634   3.407   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.223   5.671   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.531   6.485   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.479   8.025   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.120   8.749   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.813   7.935   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.069  10.289   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.710  11.013   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.376  11.103   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.658   2.772   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.166   0.650   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   25                                                  
CONECT    9    8   10   25   26                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    9    8                                                       
CONECT   26    9                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

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3D PDB for NP0050274 (Elephantopin)
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SMILES for NP0050274 (Elephantopin)
CC(=C)C(=O)O[C@H]1CC2=C[C@@H](C[C@@]3(C)O[C@@H]3[C@H]3OC(=O)C(=C)[C@H]13)OC2=O
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INCHI for NP0050274 (Elephantopin)
InChI=1S/C19H20O7/c1-8(2)16(20)24-12-6-10-5-11(23-18(10)22)7-19(4)15(26-19)14-13(12)9(3)17(21)25-14/h5,11-15H,1,3,6-7H2,2,4H3/t11-,12-,13+,14-,15+,19+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC19H20O7
Average Mass360.3620 Da
Monoisotopic Mass360.12090 Da
IUPAC Name(1R,3R,5R,6S,10R,11S)-3-methyl-9-methylidene-8,14-dioxo-4,7,15-trioxatetracyclo[11.2.1.0^{3,5}.0^{6,10}]hexadec-13(16)-en-11-yl 2-methylprop-2-enoate
Traditional Name(1R,3R,5R,6S,10R,11S)-3-methyl-9-methylidene-8,14-dioxo-4,7,15-trioxatetracyclo[11.2.1.0^{3,5}.0^{6,10}]hexadec-13(16)-en-11-yl 2-methylprop-2-enoate
CAS Registry NumberNot Available
SMILES
CC(=C)C(=O)O[C@H]1CC2=C[C@@H](C[C@@]3(C)O[C@@H]3[C@H]3OC(=O)C(=C)[C@H]13)OC2=O
InChI Identifier
InChI=1S/C19H20O7/c1-8(2)16(20)24-12-6-10-5-11(23-18(10)22)7-19(4)15(26-19)14-13(12)9(3)17(21)25-14/h5,11-15H,1,3,6-7H2,2,4H3/t11-,12-,13+,14-,15+,19+/m0/s1
InChI KeyWIQOUTANBFOBPB-KIVXNUBRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Elephantopus elatusPlant
Elephantopus mollisLOTUS Database
Elephantopus nudatusPlant
Orthopappus angustifoliusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassTricarboxylic acids and derivatives  
Direct ParentTricarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
    • 

  • 2-furanone
    • 

  • Gamma butyrolactone
    • 

  • Dihydrofuran
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Dialkyl ether
    • 

  • Oxirane
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP0.99ALOGPS
logP2.34ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area91.43 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.98 m³·mol⁻¹ChemAxon
Polarizability34.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000312  
Chemspider ID23311194  
KEGG Compound IDC09403  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkElephantopin  
METLIN IDNot Available
PubChem Compound442206  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ooi KL, Tengku Muhammad TS, Lam LY, Sulaiman SF: Cytotoxic and Apoptotic Effects of Ethyl Acetate Extract of Elephantopus mollis Kunth. in Human Liver Carcinoma HepG2 Cells Through Caspase-3 Activation. Integr Cancer Ther. 2014 May;13(3):NP1-9. doi: 10.1177/1534735411433203. Epub 2012 Feb 15. [PubMed:22336595  ]