NP-MRD: Showing NP-Card for 3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one (NP0222771)

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Record Information

Version

2.0

Created at

2022-09-06 00:41:44 UTC

Updated at

2022-09-06 00:41:44 UTC

NP-MRD ID

NP0222771

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one

Description

3-Hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-4-one 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. 3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one is found in Angelica pubescens and Ostericum grosseserratum. 3-Hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004151520032D          

 18 19  0  0  0  0            999 V2000
   -1.8212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   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
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5314   -1.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    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
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  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  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 17  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC=C1OC2CC(C)=CC(=O)C2C1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9(2)5-6-13-15(4,17)14-11(16)7-10(3)8-12(14)18-13/h5-7,12,14,17H,8H2,1-4H3

> <INCHI_KEY>
GNWNPLBSEQDDQV-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.87693406025419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-4-one

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.9501461409999994

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.476999729688643

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.27114763830184

> <JCHEM_PKA_STRONGEST_BASIC>
-3.554106407888715

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
73.6148

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3aH-1-benzofuran-4-one

> <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      -3.400  -3.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   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  -2.843   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.430  -4.058   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.992  -3.591   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13    5   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    9                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-4-one

Traditional Name

3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3aH-1-benzofuran-4-one

CAS Registry Number

Not Available

SMILES

CC(C)=CC=C1OC2CC(C)=CC(=O)C2C1(C)O

InChI Identifier

InChI=1S/C15H20O3/c1-9(2)5-6-13-15(4,17)14-11(16)7-10(3)8-12(14)18-13/h5-7,12,14,17H,8H2,1-4H3

InChI Key

GNWNPLBSEQDDQV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Angelica pubescens	LOTUS Database	35616633
Ostericum grosseserratum	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
Cyclohexenone
Tertiary alcohol
Oxolane
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.24	ALOGPS
logP	1.95	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.27	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.61 m³·mol⁻¹	ChemAxon
Polarizability	27.88 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

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 3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one (NP0222771)

MOL for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

3D MOL for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

3D SDF for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

3D-SDF for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

PDB for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

3D PDB for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

SMILES for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

INCHI for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

Structure for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)

3D Structure for NP0222771 (3-hydroxy-3,6-dimethyl-2-(3-methylbut-2-en-1-ylidene)-7,7a-dihydro-3ah-1-benzofuran-4-one)