NP-MRD: Showing NP-Card for 3,7,3',4'-tetrahydroxyflavan (NP0178278)

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Record Information

Version

2.0

Created at

2022-09-03 16:14:45 UTC

Updated at

2022-09-03 16:14:45 UTC

NP-MRD ID

NP0178278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,7,3',4'-tetrahydroxyflavan

Description

3,3',4',7-Tetrahydroxyflavan belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. 3,7,3',4'-tetrahydroxyflavan is found in Acacia mearnsii and Castela tortuosa. 3,3',4',7-Tetrahydroxyflavan is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    5.1390    1.3610   -1.9975 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2413    0.6553   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6473   -0.2722   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6834   -0.9161    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269   -0.6965    0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301    0.2298   -0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8848    0.8969   -1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592    0.4906   -0.8181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2899    0.0754    0.2369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7087    0.3012   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -0.0338   -1.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731    0.2063   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3885    0.7689   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7420    1.0096   -0.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549    1.1004    0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6691    1.6605    1.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161    0.8569    0.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213   -1.4035    0.4697 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1102   -2.0383   -0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3670   -1.4556    1.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1376    1.2176   -1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7116   -0.4337   -0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9993   -1.6425    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535    1.6295   -2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0229    0.6027    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6473   -0.4718   -2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0141   -0.0493   -2.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1300    0.7608   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6437    1.8227    1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1185    1.1306    1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -1.8555    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0273   -2.0769   -1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2335   -0.9246    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -2.5064    1.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 20  5  1  0
  5  6  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  6  7  1  0
  7  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  9 18  1  0
 17 10  1  0
  4  5  1  0
 19 32  1  0
 18 31  1  1
 20 33  1  0
 20 34  1  0
  9 25  1  1
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
  7 24  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
M  END


  Mrv0541 02241211242D          

 20 22  0  0  0  0            999 V2000
   -0.4048    1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4048    1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243    2.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0557    1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0557    1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243    0.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -0.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4048   -0.6098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4048   -1.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557   -1.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557   -2.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4048   -3.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -2.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -1.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0557   -1.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0557   -0.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -0.2017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -3.0468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440    3.0468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7068    2.2352    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 19  1  0  0  0  0
  4  5  2  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 18  1  0  0  0  0
 12 13  2  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
M  END
> <DATABASE_ID>
NP0178278

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(OC1C1=CC=C(O)C(O)=C1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c16-10-3-1-8-5-13(19)15(20-14(8)7-10)9-2-4-11(17)12(18)6-9/h1-4,6-7,13,15-19H,5H2

> <INCHI_KEY>
VFZYLYJWCROVLO-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.544127718895513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,7-diol

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
2.098672337

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.829698341787028

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.089225628657067

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2675792215127473

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
72.01880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7,3',4'-tetrahydroxyflavan

> <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      -0.756   1.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.756   3.411   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.605   4.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.971   3.411   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.971   1.896   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.605   1.138   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.605  -0.377   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.756  -1.138   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.756  -2.653   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.971  -3.411   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.971  -4.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.756  -5.687   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.605  -4.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.605  -3.411   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.971  -2.653   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.971  -1.138   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.336  -0.377   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.336  -5.687   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.455   5.687   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.186   4.172   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    9   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    7   15   17                                                  
CONECT   17   16                                                            
CONECT   18   11                                                            
CONECT   19    3                                                            
CONECT   20    4                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,7-diol, 9ci	HMDB
3',4',7-Trihydroxy-3-flavanol	HMDB

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2687 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,7-diol

Traditional Name

3,7,3',4'-tetrahydroxyflavan

CAS Registry Number

Not Available

SMILES

OC1CC2=C(OC1C1=CC=C(O)C(O)=C1)C=C(O)C=C2

InChI Identifier

InChI=1S/C15H14O5/c16-10-3-1-8-5-13(19)15(20-14(8)7-10)9-2-4-11(17)12(18)6-9/h1-4,6-7,13,15-19H,5H2

InChI Key

VFZYLYJWCROVLO-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
Acacia mearnsii	LOTUS Database	35616633
Castela tortuosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan-3-ol
1-benzopyran
Chromane
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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	1.33	ALOGPS
logP	2.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-3.3	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	72.02 m³·mol⁻¹	ChemAxon
Polarizability	27.54 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

HMDB0030541

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002415

KNApSAcK ID

Not Available

Chemspider ID

3204168

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3984814

PDB ID

Not Available

ChEBI ID

891043

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,7,3',4'-tetrahydroxyflavan (NP0178278)

MOL for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

3D MOL for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

3D SDF for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

3D-SDF for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

PDB for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

3D PDB for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

SMILES for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

INCHI for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

Structure for NP0178278 (3,7,3',4'-tetrahydroxyflavan)

3D Structure for NP0178278 (3,7,3',4'-tetrahydroxyflavan)