NP-MRD: Showing NP-Card for megastigmatrienone a (NP0257664)

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Record Information

Version

2.0

Created at

2022-09-07 22:51:07 UTC

Updated at

2022-09-07 22:51:07 UTC

NP-MRD ID

NP0257664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

megastigmatrienone a

Description

Megastigmatrienone 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. Megastigmatrienone is an extremely weak basic (essentially neutral) compound (based on its pKa). Megastigmatrienone may be a unique S. megastigmatrienone a is found in Nelumbo nucifera. Cerevisiae (yeast) metabolite.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    4.4814    0.7870   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894    1.0517    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464    0.3057   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7249    0.6373    0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615   -0.0349    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -1.2162   -0.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107   -2.1231   -0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -1.4396   -1.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470   -0.4726   -1.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9908   -0.4753   -2.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5410    0.5369   -0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7402    0.3804    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3359   -0.6427    1.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    1.7288    1.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319   -0.2913   -0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7192    1.1947   -1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    1.3020    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8468    1.8727    1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238   -0.4227   -0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5261    1.5106    1.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4075   -1.9767    0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -3.1109   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136   -2.4143   -1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713   -2.3072   -2.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    1.5209   -1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257    0.6032   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351   -0.4589    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1361   -1.6778    1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772   -0.5496    2.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1748    1.6919    2.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825    2.4694    0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7411    2.0206    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  4 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  END


  Mrv0541 02241223242D          

 14 14  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  2 13  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C=C1/C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O/c1-5-6-7-12-10(2)8-11(14)9-13(12,3)4/h5-8H,9H2,1-4H3/b6-5+,12-7+

> <INCHI_KEY>
CBQXHTWJSZXYSK-DVIJZSFDSA-N

> <FORMULA>
C13H18O

> <MOLECULAR_WEIGHT>
190.2814

> <EXACT_MASS>
190.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.850111272017728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-4-[(2E)-but-2-en-1-ylidene]-3,5,5-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
3.1696691956666676

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.659426530328395

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
62.9646

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-4-[(2E)-but-2-en-1-ylidene]-3,5,5-trimethylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    2                                                       
CONECT   14    4                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈O

Average Mass

190.2814 Da

Monoisotopic Mass

190.13577 Da

IUPAC Name

(4Z)-4-[(2E)-but-2-en-1-ylidene]-3,5,5-trimethylcyclohex-2-en-1-one

Traditional Name

(4Z)-4-[(2E)-but-2-en-1-ylidene]-3,5,5-trimethylcyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

C\C=C\C=C1/C(C)=CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C13H18O/c1-5-6-7-12-10(2)8-11(14)9-13(12,3)4/h5-8H,9H2,1-4H3/b6-5+,12-7+

InChI Key

CBQXHTWJSZXYSK-DVIJZSFDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Nelumbo nucifera	LOTUS Database	35616633

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
Organic oxide
Hydrocarbon derivative
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	4.26	ALOGPS
logP	3.17	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.96 m³·mol⁻¹	ChemAxon
Polarizability	22.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6437599

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for megastigmatrienone a (NP0257664)

MOL for NP0257664 (megastigmatrienone a)

3D MOL for NP0257664 (megastigmatrienone a)

3D SDF for NP0257664 (megastigmatrienone a)

3D-SDF for NP0257664 (megastigmatrienone a)

PDB for NP0257664 (megastigmatrienone a)

3D PDB for NP0257664 (megastigmatrienone a)

SMILES for NP0257664 (megastigmatrienone a)

INCHI for NP0257664 (megastigmatrienone a)

Structure for NP0257664 (megastigmatrienone a)

3D Structure for NP0257664 (megastigmatrienone a)