NP-MRD: Showing NP-Card for ehretine (NP0041496)

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Record Information

Version

2.0

Created at

2021-06-20 23:23:53 UTC

Updated at

2021-06-30 00:16:02 UTC

NP-MRD ID

NP0041496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ehretine

Provided By

JEOL Database JEOL Logo

Description

Ehretin belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. ehretine is found in Ehretia longiflora. ehretine was first documented in 2012 (Chien, Y.-C., et al.). Based on a literature review very few articles have been published on Ehretin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101233D          

 23 23  0  0  0  0            999 V2000
    1.9004    0.9082    3.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962    0.4605    2.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    0.3654    0.8899 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2112    0.5850    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -0.3902   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.1562   -1.0569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0928   -0.2775   -2.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9411   -0.3315   -3.6608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848   -1.8149   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017   -2.7189   -0.5439 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593   -2.1089    0.6897 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6909   -0.9991    0.5446 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5904    0.9409    4.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1972    1.9163    2.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    0.2227    2.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891    1.1582    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5226    1.6233    0.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6607    0.8468   -0.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483   -0.8543   -0.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0914   -3.0496    0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3648   -2.2417    1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -0.9809   -0.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5479   -1.2251    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  6  1  0  0  0  0
 12 11  1  0  0  0  0
  6  7  1  0  0  0  0
 12  3  1  0  0  0  0
  7  8  3  0  0  0  0
 11  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9  5  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  2  1  1  0  0  0  0
 12 22  1  0  0  0  0
 12 23  1  0  0  0  0
 11 20  1  0  0  0  0
 11 21  1  0  0  0  0
  4 17  1  0  0  0  0
  3 16  1  6  0  0  0
  6 18  1  0  0  0  0
  6 19  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C(=O)C([H])([H])C([H])([H])[C@]1([H])OC([H])([H])[H])C([H])([H])C#N

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO2/c1-12-8-2-3-9(11)7(6-8)4-5-10/h6,8H,2-4H2,1H3/t8-/m0/s1

> <INCHI_KEY>
WJWHYIKCMZCOKH-QMMMGPOBSA-N

> <FORMULA>
C9H11NO2

> <MOLECULAR_WEIGHT>
165.192

> <EXACT_MASS>
165.078978598

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.2835130768012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3S)-3-methoxy-6-oxocyclohex-1-en-1-yl]acetonitrile

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.47615944700000035

> <ALOGPS_LOGS>
-1.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.71933039435485

> <JCHEM_PKA_STRONGEST_BASIC>
-4.148649649501985

> <JCHEM_POLAR_SURFACE_AREA>
50.089999999999996

> <JCHEM_REFRACTIVITY>
45.2102

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3S)-3-methoxy-6-oxocyclohex-1-en-1-yl]acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.900   0.908   3.057  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.796   0.461   2.281  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.092   0.365   0.890  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.211   0.585   0.180  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.981  -0.390  -0.337  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.279  -0.156  -1.057  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.093  -0.278  -2.511  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.941  -0.332  -3.661  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.585  -1.815  -0.120  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.302  -2.719  -0.544  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.659  -2.109   0.690  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.691  -0.999   0.545  0.00  0.00           C+0
HETATM   13  H   UNK     0       1.590   0.941   4.105  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.197   1.916   2.752  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.747   0.223   2.967  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.789   1.158   0.590  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.523   1.623   0.090  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.661   0.847  -0.828  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.048  -0.854  -0.707  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.091  -3.050   0.331  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.365  -2.242   1.736  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.056  -0.981  -0.491  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.548  -1.225   1.188  0.00  0.00           H+0
CONECT    1    2   13   14   15                                             
CONECT    2    3    1                                                       
CONECT    3    4   12    2   16                                             
CONECT    4    3    5   17                                                  
CONECT    5    6    9    4                                                  
CONECT    6    5    7   18   19                                             
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9   11   10    5                                                  
CONECT   10    9                                                            
CONECT   11   12    9   20   21                                             
CONECT   12   11    3   22   23                                             
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    3                                                            
CONECT   17    4                                                            
CONECT   18    6                                                            
CONECT   19    6                                                            
CONECT   20   11                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23   12                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₁NO₂

Average Mass

165.1920 Da

Monoisotopic Mass

165.07898 Da

IUPAC Name

2-[(3S)-3-methoxy-6-oxocyclohex-1-en-1-yl]acetonitrile

Traditional Name

2-[(3S)-3-methoxy-6-oxocyclohex-1-en-1-yl]acetonitrile

CAS Registry Number

Not Available

SMILES

[H]C1=C(C(=O)C([H])([H])C([H])([H])[C@]1([H])OC([H])([H])[H])C([H])([H])C#N

InChI Identifier

InChI=1S/C9H11NO2/c1-12-8-2-3-9(11)7(6-8)4-5-10/h6,8H,2-4H2,1H3/t8-/m0/s1

InChI Key

WJWHYIKCMZCOKH-QMMMGPOBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ehretia longiflora	JEOL database	Chien, Y.-C., et al, Phytochem. 80, 50 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Nitrile
Carbonitrile
Ether
Dialkyl ether
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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
logP	0.53	ALOGPS
logP	0.48	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	18.72	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	50.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.21 m³·mol⁻¹	ChemAxon
Polarizability	17.28 Å³	ChemAxon
Number of Rings	1	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

Not Available

Chemspider ID

61488388

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60202034

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chien, Y.-C., et al. (2012). Chien, Y.-C., et al, Phytochem. 80, 50 (2012). Phytochem..

Showing NP-Card for ehretine (NP0041496)

MOL for NP0041496 (ehretine)

3D MOL for NP0041496 (ehretine)

3D SDF for NP0041496 (ehretine)

3D-SDF for NP0041496 (ehretine)

PDB for NP0041496 (ehretine)

3D PDB for NP0041496 (ehretine)

SMILES for NP0041496 (ehretine)

INCHI for NP0041496 (ehretine)

Structure for NP0041496 (ehretine)

3D Structure for NP0041496 (ehretine)