NP-MRD: Showing NP-Card for (3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one (NP0195009)

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Record Information

Version

2.0

Created at

2022-09-04 12:47:11 UTC

Updated at

2022-09-04 12:47:11 UTC

NP-MRD ID

NP0195009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

Description

(3S)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. (3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one is found in Saracha punctata. Based on a literature review very few articles have been published on (3S)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.1149   -1.4584   -0.9380 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4674   -0.4701   -0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308   -0.4364   -0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6818   -1.2096   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1471   -2.0409   -2.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812   -1.1157   -1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601   -0.2914   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0548   -0.2342   -0.1440 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595    0.4605    0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.4185    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932    1.1957    1.3570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148    0.9575    1.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092    0.7634    0.0194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6696    0.6701   -0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4813    1.5722   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8625    1.4272   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4617    0.3817   -0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8629    0.2491   -0.0555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583   -0.5241    0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2948   -1.5725    1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2826   -0.3945    0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -2.1841   -2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7109   -1.7120   -1.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5173    0.4576   -0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971    1.1134    1.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408    1.7426    1.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946   -0.0499    1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172    1.6514   -0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0080    2.3949   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839    2.1477   -1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3181   -0.5160    0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571   -2.2622    1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896   -1.1313    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
  9  7  1  0
 21 14  1  0
 10  3  1  0
  8 24  1  0
  6 23  1  0
  5 22  1  0
 13 28  1  6
 12 26  1  0
 12 27  1  0
  9 25  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
 20 32  1  0
 21 33  1  0
M  END


  Mrv1652309042214472D          

 21 23  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 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  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(=O)[C@H](COC2=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-5,9,16-19H,6H2/t9-/m1/s1

> <INCHI_KEY>
DYLLIDCIKLUGBZ-SECBINFHSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.255

> <EXACT_MASS>
288.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.90289689877166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
2.424092792333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.074688412621013

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.834240766323199

> <JCHEM_PKA_STRONGEST_BASIC>
-4.916250439049249

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
73.65740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    2   14                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₆

Average Mass

288.2550 Da

Monoisotopic Mass

288.06339 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)[C@H](COC2=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H12O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-5,9,16-19H,6H2/t9-/m1/s1

InChI Key

DYLLIDCIKLUGBZ-SECBINFHSA-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

Species Name	Source	Reference
Saracha punctata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanol
Isoflavanone
Hydroxyisoflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Organooxygen 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
logP	2.42	ChemAxon
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	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

162886634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one (NP0195009)

MOL for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0195009 ((3s)-3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one)