NP-MRD: Showing NP-Card for methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate (NP0301283)

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Record Information

Version

2.0

Created at

2022-09-10 14:08:25 UTC

Updated at

2022-09-10 14:08:26 UTC

NP-MRD ID

NP0301283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate

Description

methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate is found in Grangea maderaspatana. Methyl (1E)-6-[2-(5-methoxy-2-oxo-2,5-dihydrofuran-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004151514202D          

 27 28  0  0  0  0            999 V2000
    1.6024   -0.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8880   -0.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8880   -1.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554   -1.8680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3005   -2.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -3.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4755   -2.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205   -1.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -3.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3261   -4.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466   -4.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0890   -3.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -3.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -2.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481   -3.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937   -4.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663   -5.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -4.7481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216   -3.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -4.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7077   -4.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2928   -5.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923   -5.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9192   -4.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187   -5.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 14 13  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv1533004151514202D          

 27 28  0  0  0  0            999 V2000
    1.6024   -0.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8880   -0.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8880   -1.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554   -1.8680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3005   -2.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -3.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4755   -2.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205   -1.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -3.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3261   -4.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466   -4.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0890   -3.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -3.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -3.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -2.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481   -3.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937   -4.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663   -5.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -4.7481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216   -3.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -4.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7077   -4.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2928   -5.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923   -5.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9192   -4.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187   -5.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 14 13  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1OC(=O)C(CCC2(C)CC=C\C=C(C(=O)OC)/C(=C)CCC2C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-15-9-10-16(2)22(3,12-7-6-8-18(15)21(24)26-5)13-11-17-14-19(25-4)27-20(17)23/h6-8,14,16,19H,1,9-13H2,2-5H3/b7-6?,18-8+

> <INCHI_KEY>
WKBFUNWYGOKFCQ-SOUTVTLHSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.12721112941796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1E)-6-[2-(5-methoxy-2-oxo-2,5-dihydrofuran-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
5.096925932000001

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.37219323967119

> <JCHEM_PKA_STRONGEST_BASIC>
-4.321456354846267

> <JCHEM_POLAR_SURFACE_AREA>
61.83

> <JCHEM_REFRACTIVITY>
106.49329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1E)-6-[2-(5-methoxy-2-oxo-5H-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       2.991  -0.272   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.658  -1.042   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.658  -2.582   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.903  -3.487   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.428  -4.952   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.333  -6.197   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.888  -4.952   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.412  -3.487   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.018  -6.197   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.609  -7.604   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.140  -7.765   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.033  -6.229   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.635  -7.393   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.059  -5.912   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.553  -5.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.623  -6.648   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.199  -8.128   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.268  -9.236   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.844 -10.716   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.763  -8.863   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.187  -7.383   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.704  -8.500   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.188  -8.233   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.280  -9.981   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.786 -10.353   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.716  -9.246   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.222  -9.618   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   26                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   11   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1E)-6-[2-(5-methoxy-2-oxo-2,5-dihydrofuran-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylic acid	Generator

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

methyl (1E)-6-[2-(5-methoxy-2-oxo-2,5-dihydrofuran-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate

Traditional Name

methyl (1E)-6-[2-(5-methoxy-2-oxo-5H-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC1OC(=O)C(CCC2(C)CC=C\C=C(C(=O)OC)/C(=C)CCC2C)=C1

InChI Identifier

InChI=1S/C22H30O5/c1-15-9-10-16(2)22(3,12-7-6-8-18(15)21(24)26-5)13-11-17-14-19(25-4)27-20(17)23/h6-8,14,16,19H,1,9-13H2,2-5H3/b7-6?,18-8+

InChI Key

WKBFUNWYGOKFCQ-SOUTVTLHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Grangea maderaspatana	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.6	ALOGPS
logP	5.1	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.49 m³·mol⁻¹	ChemAxon
Polarizability	41.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate (NP0301283)

MOL for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

3D MOL for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

3D SDF for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

3D-SDF for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

PDB for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

3D PDB for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

SMILES for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

INCHI for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

Structure for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)

3D Structure for NP0301283 (methyl (1e)-6-[2-(5-methoxy-2-oxo-5h-furan-3-yl)ethyl]-6,7-dimethyl-10-methylidenecyclodeca-1,3-diene-1-carboxylate)