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Showing NP-Card for Elephantin (NP0050273)

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Record Information
Version2.0
Created at2022-04-27 20:50:53 UTC
Updated at2022-04-27 20:50:53 UTC
NP-MRD IDNP0050273
Secondary Accession NumbersNone
Natural Product Identification
Common NameElephantin
DescriptionElephantin belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Elephantin is found in Elephantopus elatus. Elephantin was first documented in 1969 (PMID: 5357527). Based on a literature review a small amount of articles have been published on elephantin.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050273 (Elephantin)


  Mrv1652304272222502D          

 27 30  0  0  1  0            999 V2000
    1.1407   -0.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646   -0.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249   -1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668   -1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1253   -0.1785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8673    0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507   -0.2799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4700   -0.9882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7502   -1.4636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6917   -2.2865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9497   -2.6472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2663   -2.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -3.4702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1493   -3.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659   -3.3688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0907   -4.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -5.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -5.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346   -4.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4562   -2.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6549   -3.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873   -1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8102   -2.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5509   -1.2649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -0.7420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0128    0.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  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
  4 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 11 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 10 25  1  6  0  0  0
  9 26  1  6  0  0  0
  8 26  1  0  0  0  0
  8 27  1  6  0  0  0
M  END
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3D MOL for NP0050273 (Elephantin)

Download
3D SDF for NP0050273 (Elephantin)

  Mrv1652304272222502D          

 27 30  0  0  1  0            999 V2000
    1.1407   -0.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646   -0.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249   -1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668   -1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1253   -0.1785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8673    0.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5507   -0.2799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4700   -0.9882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7502   -1.4636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6917   -2.2865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9497   -2.6472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2663   -2.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -3.4702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1493   -3.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659   -3.3688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0907   -4.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -5.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -5.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346   -4.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4562   -2.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6549   -3.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873   -1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8102   -2.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5509   -1.2649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341   -0.7420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0128    0.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  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
  4 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 11 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 10 25  1  6  0  0  0
  9 26  1  6  0  0  0
  8 26  1  0  0  0  0
  8 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=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/C20H22O7/c1-9(2)5-14(21)25-13-7-11-6-12(24-19(11)23)8-20(4)17(27-20)16-15(13)10(3)18(22)26-16/h5-6,12-13,15-17H,3,7-8H2,1-2,4H3/t12-,13-,15+,16-,17+,20+/m0/s1

> <INCHI_KEY>
HSTUUCOYVIWGLJ-DXUAHVLSSA-N

> <FORMULA>
C20H22O7

> <MOLECULAR_WEIGHT>
374.389

> <EXACT_MASS>
374.136553048

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.00499946213938

> <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 3-methylbut-2-enoate

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
2.572770799333334

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.488289586369309

> <JCHEM_PKA_STRONGEST_BASIC>
-4.241346351085584

> <JCHEM_POLAR_SURFACE_AREA>
91.43

> <JCHEM_REFRACTIVITY>
93.5752

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e-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 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050273 (Elephantin)
Download
PDB for NP0050273 (Elephantin)
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  O   UNK     0       2.129  -0.075   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.405  -1.434   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.121  -1.646   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.473  -2.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.858  -1.869   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.967  -0.333   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.352   0.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.628  -0.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.477  -1.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.134  -2.732   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.024  -4.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.640  -4.942   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.364  -4.079   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.530  -6.478   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.145  -7.151   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.870  -6.288   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.036  -8.687   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.651  -9.361   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.542 -10.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.625  -8.498   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.452  -4.847   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.822  -6.341   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.443  -3.668   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.979  -3.777   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.628  -2.361   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.904  -1.385   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.491   0.753   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   26   27                                             
CONECT    9    8   10   26                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10   12   21                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    4                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   11   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   10                                                       
CONECT   26    9    8                                                       
CONECT   27    8                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

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3D PDB for NP0050273 (Elephantin)
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SMILES for NP0050273 (Elephantin)
CC(C)=CC(=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 NP0050273 (Elephantin)
InChI=1S/C20H22O7/c1-9(2)5-14(21)25-13-7-11-6-12(24-19(11)23)8-20(4)17(27-20)16-15(13)10(3)18(22)26-16/h5-6,12-13,15-17H,3,7-8H2,1-2,4H3/t12-,13-,15+,16-,17+,20+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H22O7
Average Mass374.3890 Da
Monoisotopic Mass374.13655 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 3-methylbut-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 3-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
CC(C)=CC(=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/C20H22O7/c1-9(2)5-14(21)25-13-7-11-6-12(24-19(11)23)8-20(4)17(27-20)16-15(13)10(3)18(22)26-16/h5-6,12-13,15-17H,3,7-8H2,1-2,4H3/t12-,13-,15+,16-,17+,20+/m0/s1
InChI KeyHSTUUCOYVIWGLJ-DXUAHVLSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Elephantopus elatusPlant
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
    • 

  • Fatty acid ester
    • 

  • 2-furanone
    • 

  • Fatty acyl
    • 

  • 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
logP1.06ALOGPS
logP2.57ChemAxon
logS-3.1ALOGPS
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
Refractivity93.58 m³·mol⁻¹ChemAxon
Polarizability37 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 IDC00000311  
Chemspider ID390710  
KEGG Compound IDC09402  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442205  
PDB IDNot Available
ChEBI ID520527  
Good Scents IDNot Available
References
General References
  1. Kupchan SM, Aynehchi Y, Cassady JM, Schnoes HK, Burlingame AL: Tumor inhibitors XL. The isolation and structural elucidation of elephantin and elephantopin, two novel sesquiterpenoid tumor inhibitors from Elephantopus elatus. J Org Chem. 1969 Dec;34(12):3867-75. doi: 10.1021/jo01264a028. [PubMed:5357527  ]