NP-MRD: Showing NP-Card for methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate (NP0225234)

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Record Information

Version

2.0

Created at

2022-09-06 03:54:17 UTC

Updated at

2022-09-06 03:54:17 UTC

NP-MRD ID

NP0225234

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate

Description

Methyl 2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate is found in Bedfordia salicina. Based on a literature review very few articles have been published on methyl 2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205542D          

 19 19  0  0  1  0            999 V2000
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5724    2.1882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421    3.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5724    3.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270   -1.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497   -1.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8077   -1.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6304   -2.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -2.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0861   -1.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225234

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)[C@@H]1CC[C@H](C)C(CCC(C)=O)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O3/c1-11-5-7-15(13(3)16(18)19-4)10-9-14(11)8-6-12(2)17/h9,11,15H,3,5-8,10H2,1-2,4H3/t11-,15+/m0/s1

> <INCHI_KEY>
JZZHOKITGPASIG-XHDPSFHLSA-N

> <FORMULA>
C16H24O3

> <MOLECULAR_WEIGHT>
264.365

> <EXACT_MASS>
264.172544633

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.272429949038866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate

> <JCHEM_LOGP>
3.420841489

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.595438466794175

> <JCHEM_PKA_STRONGEST_BASIC>
-6.707085381238588

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
76.5347

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.933   4.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599   4.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.265   4.855   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.068   4.085   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.265   6.395   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.068   7.165   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.986   1.876   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.037  -2.216   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.573  -2.331   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241  -3.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.777  -3.834   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.373  -4.991   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.161  -2.216   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.211   1.876   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    7                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoic acid	Generator

Chemical Formula

C₁₆H₂₄O₃

Average Mass

264.3650 Da

Monoisotopic Mass

264.17254 Da

IUPAC Name

methyl 2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate

Traditional Name

methyl 2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)[C@@H]1CC[C@H](C)C(CCC(C)=O)=CC1

InChI Identifier

InChI=1S/C16H24O3/c1-11-5-7-15(13(3)16(18)19-4)10-9-14(11)8-6-12(2)17/h9,11,15H,3,5-8,10H2,1-2,4H3/t11-,15+/m0/s1

InChI Key

JZZHOKITGPASIG-XHDPSFHLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bedfordia salicina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Xanthane sesquiterpenoid
Sesquiterpenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.42	ChemAxon
pKa (Strongest Acidic)	19.6	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	76.53 m³·mol⁻¹	ChemAxon
Polarizability	30.27 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

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

163006741

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate (NP0225234)

MOL for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

3D MOL for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

3D SDF for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

3D-SDF for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

PDB for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

3D PDB for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

SMILES for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

INCHI for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

Structure for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)

3D Structure for NP0225234 (methyl 2-[(1r,5s)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoate)