NP-MRD: Showing NP-Card for fisetinidol (NP0240217)

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Record Information

Version

2.0

Created at

2022-09-06 23:58:30 UTC

Updated at

2022-09-06 23:58:30 UTC

NP-MRD ID

NP0240217

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fisetinidol

Description

Fisetinidol 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. Thus, fisetinidol is considered to be a flavonoid. Fisetinidol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. fisetinidol is found in Acacia mearnsii, Acacia terminalis, Burkea africana, Castela tortuosa and Colophospermum mopane. fisetinidol was first documented in 2002 (PMID: 11933117). Based on a literature review a small amount of articles have been published on fisetinidol (PMID: 21660093) (PMID: 21799697) (PMID: 21830887).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    4.9505    2.5971   -0.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1095    1.5076    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174    0.2677    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7653   -0.8174    0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4194   -0.6803    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9468    0.5536   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657    1.6712   -0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6106    0.6988   -0.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390   -0.3891   -0.6513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6282    0.0529   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    0.7529    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2075    1.1709    1.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2501    0.8904    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5465    1.3017    0.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929    0.1970   -0.9202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9957   -0.1105   -1.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -0.2116   -1.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375   -1.6563    0.0070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312   -2.7519   -0.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5686   -1.8723    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9321    2.5454    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6609    0.1532    0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -1.7868    0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    2.6474   -0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1863   -0.5526   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1087    0.9633    1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4388    1.7148    2.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3302    1.1230   -0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9528    0.1180   -1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -0.7559   -2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349   -1.7301    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076   -2.6587   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7257   -2.3122    1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170   -2.6413   -0.4133 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  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2  7  1  0
  7  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
  9 18  1  0
 17 10  1  0
  6  5  1  0
 19 32  1  0
 18 31  1  1
 20 33  1  0
 20 34  1  0
  4 23  1  0
  3 22  1  0
  1 21  1  0
  7 24  1  0
  9 25  1  6
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
M  END


  Mrv1652309072201592D          

 20 22  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 O   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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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  0  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
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 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  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  5 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=CC=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C1

> <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/t13-,15+/m0/s1

> <INCHI_KEY>
VFZYLYJWCROVLO-DZGCQCFKSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.272

> <EXACT_MASS>
274.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.16225099805272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.098672337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.829698341787033

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.089225628657278

> <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

> <JCHEM_TRADITIONAL_IUPAC>
fisetinidol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10                                                       
CONECT   18    9   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    5                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
3,7,3',4'-Tetrahydroxyflavan	ChEBI

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2720 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

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

Traditional Name

fisetinidol

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=CC=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C1

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/t13-,15+/m0/s1

InChI Key

VFZYLYJWCROVLO-DZGCQCFKSA-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
Acacia terminalis	LOTUS Database	35616633
Burkea africana	LOTUS Database	35616633
Castela tortuosa	LOTUS Database	35616633
Colophospermum mopane	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

catechin (CHEBI:5066 )
tetrahydroxyflavan (CHEBI:5066 )
Flavans, Flavanols and Leucoanthocyanidins (C09735 )
Flavan 3-ols (C09735 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020013 )

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	2.1	ChemAxon
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	27.16 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008822

Chemspider ID

390840

KEGG Compound ID

C09735

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fisetinidol

METLIN ID

Not Available

PubChem Compound

442397

PDB ID

Not Available

ChEBI ID

5066

Good Scents ID

Not Available

References

General References

Mathisen E, Diallo D, Andersen OM, Malterud KE: Antioxidants from the bark of Burkea africana, an African medicinal plant. Phytother Res. 2002 Mar;16(2):148-53. doi: 10.1002/ptr.936. [PubMed:11933117 ]
Ikarashi N, Takeda R, Ito K, Ochiai W, Sugiyama K: The inhibition of lipase and glucosidase activities by acacia polyphenol. Evid Based Complement Alternat Med. 2011;2011:272075. doi: 10.1093/ecam/neq043. Epub 2011 Feb 14. [PubMed:21660093 ]
Ikarashi N, Toda T, Okaniwa T, Ito K, Ochiai W, Sugiyama K: Anti-Obesity and Anti-Diabetic Effects of Acacia Polyphenol in Obese Diabetic KKAy Mice Fed High-Fat Diet. Evid Based Complement Alternat Med. 2011;2011:952031. doi: 10.1093/ecam/nep241. Epub 2011 Apr 14. [PubMed:21799697 ]
Li XC, Liu C, Yang LX, Chen RY: Phenolic compounds from the aqueous extract of Acacia catechu. J Asian Nat Prod Res. 2011 Sep;13(9):826-30. doi: 10.1080/10286020.2011.597384. [PubMed:21830887 ]
LOTUS database [Link]

Showing NP-Card for fisetinidol (NP0240217)

MOL for NP0240217 (fisetinidol)

3D MOL for NP0240217 (fisetinidol)

3D SDF for NP0240217 (fisetinidol)

3D-SDF for NP0240217 (fisetinidol)

PDB for NP0240217 (fisetinidol)

3D PDB for NP0240217 (fisetinidol)

SMILES for NP0240217 (fisetinidol)

INCHI for NP0240217 (fisetinidol)

Structure for NP0240217 (fisetinidol)

3D Structure for NP0240217 (fisetinidol)