NP-MRD: Showing NP-Card for 7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol (NP0056235)

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Record Information

Version

2.0

Created at

2022-04-28 02:04:12 UTC

Updated at

2022-04-28 02:04:12 UTC

NP-MRD ID

NP0056235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol

Description

7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol is found in Acacia acuminata, Acacia concurrens, Acacia excelsa, Acacia harpophylla, Acacia holosericea , Acacia homalophylla , Acacia longifolia, Acacia melanoxylon , Acacia obtusifolia, Acacia oswaldii, Acacia pendula, Acacia retinodes, Acacia rigens, Acacia verniciflua and Acacia nigrescens.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    5.8486    0.1331   -0.0585 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4715    0.0524    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9737   -0.1399    1.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6089   -0.2206    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6866   -0.1134    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -0.2035    0.9336 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4184    0.8397    0.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7719    0.8016   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2686   -0.4337   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5917   -0.5597   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4423    0.5429   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9716    1.7705   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8582    2.8304   -0.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6286    1.8842    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1092    3.1015    0.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805   -1.5271   -0.5768 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9426   -2.7368   -0.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410   -1.5448    0.6127 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6750   -2.4847    0.3838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1899    0.0783   -0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    0.1604   -0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814    0.3533   -2.1465 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2639    0.2721   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6986   -0.2251    2.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -0.3715    2.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269   -0.0145    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9750   -1.5301   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4976    0.3931   -0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6166    3.7663    0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6402    3.9491    0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298   -1.4022   -1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6671   -3.3918   -0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9317   -1.9441    1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7641   -2.6782   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4685    0.1627   -1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9156    0.4301   -2.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 20  2  0
 20 21  1  0
 21 22  1  0
 21  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  6 18  1  0
  4  5  1  0
  8  9  1  0
 19 34  1  0
 18 33  1  1
 16 31  1  6
 17 32  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 15 30  1  0
  6 26  1  1
 20 35  1  0
 22 36  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
M  END


  Mrv1652302211917532D          

 22 24  0  0  0  0            999 V2000
 9997.325610000.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7505 9996.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.894710001.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.321710000.5172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.1769 9997.6251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8964 9999.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3256 9999.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6110 9998.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6110 9998.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3255 9997.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.607110000.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.892710000.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.178010000.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.1780 9999.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8926 9998.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6071 9999.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7513 9999.2773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0368 9998.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0368 9998.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7513 9997.6275    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.4657 9998.0398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.4657 9998.8648    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
 11  4  1  0  0  0  0
 12  3  1  0  0  0  0
  8  6  1  0  0  0  0
  1  7  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 21  5  1  6  0  0  0
 20  2  1  1  0  0  0
 18  7  2  0  0  0  0
 10 19  2  0  0  0  0
 22 14  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0056235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)C2=CC=C(O)C(O)=C2O[C@@H]1C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O7/c16-8-3-1-6(5-10(8)18)14-13(21)11(19)7-2-4-9(17)12(20)15(7)22-14/h1-5,11,13-14,16-21H/t11-,13+,14+/m0/s1

> <INCHI_KEY>
JEUXGAUBSWADEA-IACUBPJLSA-N

> <FORMULA>
C15H14O7

> <MOLECULAR_WEIGHT>
306.27

> <EXACT_MASS>
306.073952791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.224582088613865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,7,8-tetrol

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.8761108683333332

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.64006513983993

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.007456759146379

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6145948201125737

> <JCHEM_POLAR_SURFACE_AREA>
130.61

> <JCHEM_REFRACTIVITY>
75.2072

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epimesquitol-4β-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-FEB-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-FEB-19         0                                  
HETATM    1  O   UNK     0    8661.6748666.870   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8664.3348660.686   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8668.3378669.172   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8671.0018667.632   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8666.9978662.233   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8659.0078665.326   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8661.6748665.318   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8660.3418664.548   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8660.3418663.008   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.6748662.238   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8669.6678666.865   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.3338667.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.9998666.865   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.9998665.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.3338664.555   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.6678665.325   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8664.3368665.318   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8663.0028664.548   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.0028663.008   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.3368662.238   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.6698663.008   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8665.6698664.548   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   20                                                            
CONECT    3   12                                                            
CONECT    4   11                                                            
CONECT    5   21                                                            
CONECT    6    8                                                            
CONECT    7    8    1   18                                                  
CONECT    8    7    9    6                                                  
CONECT    9    8   10                                                       
CONECT   10    9   19                                                       
CONECT   11   12   16    4                                                  
CONECT   12   11   13    3                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   18   22                                                       
CONECT   18   19   17    7                                                  
CONECT   19   18   20   10                                                  
CONECT   20   19   21    2                                                  
CONECT   21   20   22    5                                                  
CONECT   22   21   17   14                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₇

Average Mass

306.2700 Da

Monoisotopic Mass

306.07395 Da

IUPAC Name

(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,7,8-tetrol

Traditional Name

epimesquitol-4β-ol

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)C2=CC=C(O)C(O)=C2O[C@@H]1C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O7/c16-8-3-1-6(5-10(8)18)14-13(21)11(19)7-2-4-9(17)12(20)15(7)22-14/h1-5,11,13-14,16-21H/t11-,13+,14+/m0/s1

InChI Key

JEUXGAUBSWADEA-IACUBPJLSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 acuminata	Plant	KNApSAcK
Acacia concurrens	Plant	KNApSAcK
Acacia excelsa	Plant	KNApSAcK
Acacia harpophylla	Plant	KNApSAcK
Acacia holosericea	Plant	KNApSAcK
Acacia homalophylla	Plant	KNApSAcK
Acacia longifolia	Plant	KNApSAcK
Acacia melanoxylon	Plant	KNApSAcK
Acacia obtusifolia	Plant	KNApSAcK
Acacia oswaldii	Plant	KNApSAcK
Acacia pendula	Plant	KNApSAcK
Acacia retinodes	Plant	KNApSAcK
Acacia rigens	Plant	KNApSAcK
Acacia verniciflua	Plant	KNApSAcK
Senegalia nigrescens	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	0.5	ALOGPS
logP	0.88	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.21 m³·mol⁻¹	ChemAxon
Polarizability	29.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for 7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol (NP0056235)

MOL for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

3D MOL for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

3D SDF for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

3D-SDF for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

PDB for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

3D PDB for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

SMILES for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

INCHI for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

Structure for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)

3D Structure for NP0056235 (7,8,3',4'-Tetrahydroxy-2,3-cis-flavan-3,4-trans-diol)