NP-MRD: Showing NP-Card for 7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate (NP0182324)

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Record Information

Version

2.0

Created at

2022-09-03 20:58:53 UTC

Updated at

2022-09-03 20:58:53 UTC

NP-MRD ID

NP0182324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate

Description

7A-(hydroxymethyl)-4,4-dimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate is found in Melia azedarach. 7A-(hydroxymethyl)-4,4-dimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191521452D          

 23 24  0  0  0  0            999 V2000
    5.4957    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    0.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045   -0.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505    3.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251    3.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C(C)CC(=O)OC1C=CC2(CO)OC(=O)CC2C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O5/c1-11(2)12(3)8-15(20)22-14-6-7-18(10-19)13(17(14,4)5)9-16(21)23-18/h6-7,13-14,19H,8-10H2,1-5H3

> <INCHI_KEY>
MEOOEKUHUBRFQB-UHFFFAOYSA-N

> <FORMULA>
C18H26O5

> <MOLECULAR_WEIGHT>
322.401

> <EXACT_MASS>
322.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.516560117301

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.129878902333334

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.289099758833117

> <JCHEM_PKA_STRONGEST_BASIC>
-3.109747765486393

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
86.712

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3H-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      10.259  10.543   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.258   6.693   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.429   0.541   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.675  -0.364   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.201   5.743   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.647   5.743   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.592   8.233   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15   19                                             
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19    9   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    2                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
7a-(Hydroxymethyl)-4,4-dimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-1-benzofuran-5-yl 3,4-dimethylpent-3-enoic acid	Generator

Chemical Formula

C₁₈H₂₆O₅

Average Mass

322.4010 Da

Monoisotopic Mass

322.17802 Da

IUPAC Name

7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate

Traditional Name

7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3H-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate

CAS Registry Number

Not Available

SMILES

CC(C)=C(C)CC(=O)OC1C=CC2(CO)OC(=O)CC2C1(C)C

InChI Identifier

InChI=1S/C18H26O5/c1-11(2)12(3)8-15(20)22-14-6-7-18(10-19)13(17(14,4)5)9-16(21)23-18/h6-7,13-14,19H,8-10H2,1-5H3

InChI Key

MEOOEKUHUBRFQB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.35	ALOGPS
logP	2.13	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.29	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.71 m³·mol⁻¹	ChemAxon
Polarizability	34.52 Å³	ChemAxon
Number of Rings	2	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

78385578

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate (NP0182324)

MOL for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

3D MOL for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

3D SDF for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

3D-SDF for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

PDB for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

3D PDB for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

SMILES for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

INCHI for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

Structure for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)

3D Structure for NP0182324 (7a-(hydroxymethyl)-4,4-dimethyl-2-oxo-3a,5-dihydro-3h-1-benzofuran-5-yl 3,4-dimethylpent-3-enoate)