NP-MRD: Showing NP-Card for Anantine (NP0051340)

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Record Information

Version

2.0

Created at

2022-04-27 22:44:04 UTC

Updated at

2022-04-27 22:44:04 UTC

NP-MRD ID

NP0051340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Anantine

Description

Anantine belongs to the class of organic compounds known as n-substituted imidazoles. These are heterocyclic compounds containing an imidazole ring substituted at position 1. Anantine is found in Cynometra ananta, Cynometra anata and Cynometra lujae. Anantine was first documented in 1997 (PMID: 9433762). Based on a literature review very few articles have been published on Anantine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.6770    2.5639    1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528    1.5578    0.3910 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987    1.6802   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680    0.5136   -1.2604 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657   -0.3613   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -1.7154   -0.2863 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3419   -2.5972    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -3.8809    0.3900 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -3.6276   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4340   -4.4480   -0.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551   -2.1232   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7960   -1.5136   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308   -0.0867   -0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945    0.4383   -1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8317    1.7841   -1.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040    2.6801   -0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408    2.1832    0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163    0.8246    0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326    0.2999    0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570    2.8046    2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188    2.0981    1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988    3.4348    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8582    2.6001   -1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312   -2.2421   -1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -2.5844    0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8956   -2.2803    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094   -4.8143    0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6997   -2.1574   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550   -0.2395   -2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3583    2.1723   -2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053    3.7312   -0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3917    2.8697    1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087    0.4948    1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148   -0.0594    1.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 19  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 19  2  1  0
 11  6  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 19 34  1  0
  6 24  1  6
  7 25  1  0
  7 26  1  0
  8 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1652304282200442D          

 19 21  0  0  1  0            999 V2000
   -2.7512    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5846    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -0.2169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    0.5678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4888    0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1562    0.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8236    0.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5687    1.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7437    1.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6083    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC(=C1)[C@H]1CNC(=O)\C1=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H15N3O/c1-18-9-14(17-10-18)13-8-16-15(19)12(13)7-11-5-3-2-4-6-11/h2-7,9-10,13H,8H2,1H3,(H,16,19)/b12-7+/t13-/m0/s1

> <INCHI_KEY>
UKNFHVAQMUDAFF-WHGQRRHOSA-N

> <FORMULA>
C15H15N3O

> <MOLECULAR_WEIGHT>
253.305

> <EXACT_MASS>
253.121512115

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.93309453582939

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,4R)-4-(1-methyl-1H-imidazol-4-yl)-3-(phenylmethylidene)pyrrolidin-2-one

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.2866570336666665

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.258911040363987

> <JCHEM_PKA_STRONGEST_BASIC>
6.230508537323178

> <JCHEM_POLAR_SURFACE_AREA>
46.92

> <JCHEM_REFRACTIVITY>
74.3475

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,4R)-4-(1-methylimidazol-4-yl)-3-(phenylmethylidene)pyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -5.136   5.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.136   4.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.469   3.505   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.803   4.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.803   5.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.469   6.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.802   3.505   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.802   1.965   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.556   1.060   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.091   1.536   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -3.032  -0.405   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.572  -0.405   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.048   1.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.512   1.536   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.758   0.631   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -9.004   1.536   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -8.528   3.000   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -6.988   3.000   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0     -10.469   1.060   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₅N₃O

Average Mass

253.3050 Da

Monoisotopic Mass

253.12151 Da

IUPAC Name

(3E,4R)-4-(1-methyl-1H-imidazol-4-yl)-3-(phenylmethylidene)pyrrolidin-2-one

Traditional Name

(3E,4R)-4-(1-methylimidazol-4-yl)-3-(phenylmethylidene)pyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CN1C=NC(=C1)[C@H]1CNC(=O)\C1=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H15N3O/c1-18-9-14(17-10-18)13-8-16-15(19)12(13)7-11-5-3-2-4-6-11/h2-7,9-10,13H,8H2,1H3,(H,16,19)/b12-7+/t13-/m0/s1

InChI Key

UKNFHVAQMUDAFF-WHGQRRHOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cynometra ananta	Plant	KNApSAcK
Cynometra anata	Plant	KNApSAcK
Cynometra lujae	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-substituted imidazoles. These are heterocyclic compounds containing an imidazole ring substituted at position 1.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

N-substituted imidazoles

Alternative Parents

Substituents

Monocyclic benzene moiety
N-substituted imidazole
Pyrrolidone
2-pyrrolidone
Benzenoid
Pyrrolidine
Heteroaromatic compound
Secondary carboxylic acid amide
Lactam
Carboxamide group
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:2701 )

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
logP	1.87	ALOGPS
logP	1.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.26	ChemAxon
pKa (Strongest Basic)	6.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.35 m³·mol⁻¹	ChemAxon
Polarizability	26.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002313

Chemspider ID

4445126

KEGG Compound ID

C10568

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281815

PDB ID

Not Available

ChEBI ID

2701

Good Scents ID

Not Available

References

General References

Naito T, Honda Y, Bhavakul V, Yamaguchi S, Fujiwara A, Miyata O, Ninomiya I: Radical cyclization in heterocycle synthesis. II. Total synthesis of (+/-)-anantine and (+/-)-isoanantine. Chem Pharm Bull (Tokyo). 1997 Dec;45(12):1932-9. doi: 10.1248/cpb.45.1932. [PubMed:9433762 ]

Showing NP-Card for Anantine (NP0051340)

MOL for NP0051340 (Anantine)

3D MOL for NP0051340 (Anantine)

3D SDF for NP0051340 (Anantine)

3D-SDF for NP0051340 (Anantine)

PDB for NP0051340 (Anantine)

3D PDB for NP0051340 (Anantine)

SMILES for NP0051340 (Anantine)

INCHI for NP0051340 (Anantine)

Structure for NP0051340 (Anantine)

3D Structure for NP0051340 (Anantine)