NP-MRD: Showing NP-Card for 3,4,4',7-Tetrahydroxyflavan (NP0138407)

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Record Information

Version

1.0

Created at

2022-05-31 17:58:02 UTC

Updated at

2022-05-31 17:58:03 UTC

NP-MRD ID

NP0138407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,4',7-Tetrahydroxyflavan

Description

(2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (2S,3S,4R)-3,4,4',7-Tetrahydroxyflavan has been detected, but not quantified in, fruits. 3,4,4',7-Tetrahydroxyflavan is found in Brucea javanica and Guibourtia coleosperma. This could make (2S,3S,4R)-3,4,4',7-tetrahydroxyflavan a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9074    0.7810    0.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5675    0.4770    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    1.5278   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3947    1.2787   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8401   -0.0058   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842   -0.1911   -0.3933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2976    0.8443    0.3111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6904    0.7661    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    1.9552    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8120    1.9157    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6123    3.0443    0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3850    0.6643    0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6661   -0.4914    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2734   -0.4655    0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972   -1.7061    0.3505 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6408   -2.3016    1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567   -1.5395    0.0786 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3127   -2.5315   -0.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7086   -1.0378    0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607   -0.8042    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5194    0.7798   -0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678    2.5499   -0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7045    2.0769   -0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221   -0.1462   -1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541    2.9205    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9780    3.5307    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4815    0.6199    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -1.4881    0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -2.4297   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1900   -1.7246    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5392   -1.8014    1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0024   -3.4103   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552   -2.0511    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649   -1.6062    0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 20  1  0
 20 19  2  0
  6 17  1  0
 19  5  1  0
  8 14  1  0
 18 32  1  0
 17 31  1  1
 15 29  1  6
 16 30  1  0
 13 28  1  0
 12 27  1  0
 11 26  1  0
  9 25  1  0
  6 24  1  6
  4 23  1  0
  3 22  1  0
  1 21  1  0
 20 34  1  0
 19 33  1  0
M  END


  Mrv0541 02241210282D          

 20 22  0  0  0  0            999 V2000
    1.8144   -1.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -1.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8144    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8144   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 15  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C2=CC=C(O)C=C2OC1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-14(19)13(18)11-6-5-10(17)7-12(11)20-15/h1-7,13-19H

> <INCHI_KEY>
NTLUSUFJOUMRLA-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.52740731244312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,7-triol

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.4832415116666668

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.738987737853373

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.134618961218838

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5993488556195237

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
71.24539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.387  -3.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001  -2.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.387  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.619  -1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.619  -2.694   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.005  -3.464   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.619   1.154   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.387   1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.001   1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.615   1.924   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.615   3.464   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.001   1.924   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.615   1.154   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.615  -0.384   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.615  -1.154   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.001  -0.384   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.387  -1.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.619  -0.384   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.005  -1.154   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9   19                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   11   13   15                                                  
CONECT   15    3   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19    8   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2687 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,7-triol

Traditional Name

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,7-triol

CAS Registry Number

38412-82-7

SMILES

OC1C(O)C2=CC=C(O)C=C2OC1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-14(19)13(18)11-6-5-10(17)7-12(11)20-15/h1-7,13-19H

InChI Key

NTLUSUFJOUMRLA-UHFFFAOYSA-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
Brucea javanica	LOTUS Database	35616633
Guibourtia coleosperma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Leucoanthocyanidins

Alternative Parents

Substituents

Leucoanthocyanidin-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
4-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
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	1.05	ALOGPS
logP	1.48	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.25 m³·mol⁻¹	ChemAxon
Polarizability	27.53 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

HMDB0040828

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020648

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

13886894

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,4,4',7-Tetrahydroxyflavan (NP0138407)

MOL for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

3D MOL for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

3D SDF for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

3D-SDF for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

PDB for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

3D PDB for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

SMILES for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

INCHI for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

Structure for NP0138407 (3,4,4',7-Tetrahydroxyflavan)

3D Structure for NP0138407 (3,4,4',7-Tetrahydroxyflavan)