NP-MRD: Showing NP-Card for (3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one (NP0256991)

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Record Information

Version

2.0

Created at

2022-09-07 21:59:34 UTC

Updated at

2022-09-07 21:59:34 UTC

NP-MRD ID

NP0256991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one

Description

(3S)-5-hydroxy-3-[(3R)-3-hydroxybutyl]-1,3-dihydro-2-benzofuran-1-one belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone. (3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one is found in Foeniculum vulgare. Based on a literature review very few articles have been published on (3S)-5-hydroxy-3-[(3R)-3-hydroxybutyl]-1,3-dihydro-2-benzofuran-1-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072223592D          

 16 17  0  0  1  0            999 V2000
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    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
    4.0668   -1.5229    0.0000 O   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
    1.9233   -1.1104    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  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  6 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)CC[C@@H]1OC(=O)C2=CC=C(O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-7(13)2-5-11-10-6-8(14)3-4-9(10)12(15)16-11/h3-4,6-7,11,13-14H,2,5H2,1H3/t7-,11+/m1/s1

> <INCHI_KEY>
IMUDJPJBCPARAW-HQJQHLMTSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.24

> <EXACT_MASS>
222.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.044297313728794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-5-hydroxy-3-[(3R)-3-hydroxybutyl]-1,3-dihydro-2-benzofuran-1-one

> <JCHEM_LOGP>
1.5879472523333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.613731014434556

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.350419604234675

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5105017318049816

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
58.5101

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5-hydroxy-3-[(3R)-3-hydroxybutyl]-3H-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10    6                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄O₄

Average Mass

222.2400 Da

Monoisotopic Mass

222.08921 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H](O)CC[C@@H]1OC(=O)C2=CC=C(O)C=C12

InChI Identifier

InChI=1S/C12H14O4/c1-7(13)2-5-11-10-6-8(14)3-4-9(10)12(15)16-11/h3-4,6-7,11,13-14H,2,5H2,1H3/t7-,11+/m1/s1

InChI Key

IMUDJPJBCPARAW-HQJQHLMTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Foeniculum vulgare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Benzofuranones

Direct Parent

Benzofuranones

Alternative Parents

Substituents

Benzofuranone
Phthalide
Isobenzofuranone
Isocoumaran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

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

162975897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one (NP0256991)

MOL for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

3D MOL for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

3D SDF for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

3D-SDF for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

PDB for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

3D PDB for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

SMILES for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

INCHI for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

Structure for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)

3D Structure for NP0256991 ((3s)-5-hydroxy-3-[(3r)-3-hydroxybutyl]-3h-2-benzofuran-1-one)