NP-MRD: Showing NP-Card for (2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid (NP0325847)

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Record Information

Version

2.0

Created at

2022-09-12 06:55:15 UTC

Updated at

2022-09-12 06:55:15 UTC

NP-MRD ID

NP0325847

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

Description

(2S)-2alpha-(4-Hydroxyphenyl)-3beta-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylic acid belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid is found in Selaginella moellendorffii. Based on a literature review very few articles have been published on (2S)-2alpha-(4-Hydroxyphenyl)-3beta-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122208552D          

 21 23  0  0  1  0            999 V2000
    4.7812    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    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
    1.9233    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
    1.1387    2.1904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  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
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 13 21  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325847

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1[C@H](OC2=CC=C(C=C12)C(O)=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c17-8-13-12-7-10(16(19)20)3-6-14(12)21-15(13)9-1-4-11(18)5-2-9/h1-7,13,15,17-18H,8H2,(H,19,20)/t13-,15+/m0/s1

> <INCHI_KEY>
ACJPWQXRDQNVEB-DZGCQCFKSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.273142540145106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <JCHEM_LOGP>
1.963571767

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.471457119855296

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.326715309229708

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7214438670873022

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
75.65220000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       8.925   3.613   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.591   5.923   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.143   5.874   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.940   2.843   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   21                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
CONECT   21   13    7                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2a-(4-Hydroxyphenyl)-3b-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylate	Generator
(2S)-2a-(4-Hydroxyphenyl)-3b-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylic acid	Generator
(2S)-2alpha-(4-Hydroxyphenyl)-3beta-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylate	Generator
(2S)-2Α-(4-hydroxyphenyl)-3β-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylate	Generator
(2S)-2Α-(4-hydroxyphenyl)-3β-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylic acid	Generator

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

(2S,3R)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

Traditional Name

(2S,3R)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC[C@@H]1[C@H](OC2=CC=C(C=C12)C(O)=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O5/c17-8-13-12-7-10(16(19)20)3-6-14(12)21-15(13)9-1-4-11(18)5-2-9/h1-7,13,15,17-18H,8H2,(H,19,20)/t13-,15+/m0/s1

InChI Key

ACJPWQXRDQNVEB-DZGCQCFKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Selaginella moellendorffii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Ether
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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
logP	1.96	ChemAxon
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.65 m³·mol⁻¹	ChemAxon
Polarizability	29.27 Å³	ChemAxon
Number of Rings	3	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

102262565

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid (NP0325847)

MOL for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

3D MOL for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

3D SDF for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

3D-SDF for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

PDB for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

3D PDB for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

SMILES for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

INCHI for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

Structure for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)

3D Structure for NP0325847 ((2s,3r)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid)