NP-MRD: Showing NP-Card for [(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid (NP0299221)

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Record Information

Version

2.0

Created at

2022-09-10 10:55:34 UTC

Updated at

2022-09-10 10:55:34 UTC

NP-MRD ID

NP0299221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid

Description

(?)-Herbaric acid, also known as (?)-Herbarate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Based on a literature review very few articles have been published on (?)-Herbaric acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102212552D          

 16 17  0  0  1  0            999 V2000
   -0.1781   -3.1062    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
   -0.4752   -1.7084    0.0000 O   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
    2.6378    0.9521    0.0000 O   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  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 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
  9 16  1  0  0  0  0
  5 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299221

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O6/c11-4-1-5-7(3-8(13)14)16-10(15)9(5)6(12)2-4/h1-2,7,11-12H,3H2,(H,13,14)/t7-/m0/s1

> <INCHI_KEY>
YIQRZXRYUUYARN-ZETCQYMHSA-N

> <FORMULA>
C10H8O6

> <MOLECULAR_WEIGHT>
224.168

> <EXACT_MASS>
224.032087978

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.010457718096166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S)-4,6-dihydroxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl]acetic acid

> <JCHEM_LOGP>
1.3455825526666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.43021830419716

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0813704496778533

> <JCHEM_PKA_STRONGEST_BASIC>
-4.017285223193732

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
51.053900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S)-4,6-dihydroxy-3-oxo-1H-2-benzofuran-1-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.333  -5.798   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+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   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9    5                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(?)-herbarate	Generator

Chemical Formula

C₁₀H₈O₆

Average Mass

224.1680 Da

Monoisotopic Mass

224.03209 Da

IUPAC Name

2-[(1S)-4,6-dihydroxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl]acetic acid

Traditional Name

[(1S)-4,6-dihydroxy-3-oxo-1H-2-benzofuran-1-yl]acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H8O6/c11-4-1-5-7(3-8(13)14)16-10(15)9(5)6(12)2-4/h1-2,7,11-12H,3H2,(H,13,14)/t7-/m0/s1

InChI Key

YIQRZXRYUUYARN-ZETCQYMHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
Benzofuranone
Phthalide
Isobenzofuranone
Isocoumaran
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen 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	1.35	ChemAxon
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.05 m³·mol⁻¹	ChemAxon
Polarizability	20.01 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

28288260

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

49840812

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid (NP0299221)

MOL for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

3D MOL for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

3D SDF for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

3D-SDF for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

PDB for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

3D PDB for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

SMILES for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

INCHI for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

Structure for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)

3D Structure for NP0299221 ([(1s)-4,6-dihydroxy-3-oxo-1h-2-benzofuran-1-yl]acetic acid)