NP-MRD: Showing NP-Card for favan-3-ol (NP0197923)

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Record Information

Version

2.0

Created at

2022-09-04 16:16:55 UTC

Updated at

2022-09-04 16:16:55 UTC

NP-MRD ID

NP0197923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

favan-3-ol

Description

Flavan-3-ol, also known as 3-flavan-ol, 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. favan-3-ol is found in Cinnamomum triplinerve and Malus sylvestris. favan-3-ol was first documented in 2022 (PMID: 36014504). Based on a literature review a small amount of articles have been published on Flavan-3-ol (PMID: 35986624) (PMID: 35976259) (PMID: 35931563).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.6470   -1.2289    2.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183   -0.4359    1.2247 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5356   -1.0204    1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3295   -0.0910    0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6800    0.0133    0.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892    0.8685   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8839    1.6114   -1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    1.4994   -1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229    0.6549   -0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    0.5644   -0.8930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3650   -0.4545   -0.2110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8165   -0.3234   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3963    0.9080   -0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724    1.0346   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772   -0.0474   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0040   -1.2899   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296   -1.4036   -0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071   -1.0638    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1826    0.6142    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812   -1.0655    2.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4317   -2.0219    0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1310   -0.5807    1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5386    0.8928    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    2.2907   -1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0858    2.1024   -2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763   -1.4249   -0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    1.7791    0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2003    2.0331   -0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6578    0.0899   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6466   -2.1337   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1911   -2.3711   -0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11  2  1  0
 17 12  1  0
  9  4  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  6
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv1652309042218162D          

 17 19  0  0  0  0            999 V2000
    0.0000    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
    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
    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
    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=CC=CC=C2OC1C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O2/c16-13-10-12-8-4-5-9-14(12)17-15(13)11-6-2-1-3-7-11/h1-9,13,15-16H,10H2

> <INCHI_KEY>
OEIJRRGCTVHYTH-UHFFFAOYSA-N

> <FORMULA>
C15H14O2

> <MOLECULAR_WEIGHT>
226.275

> <EXACT_MASS>
226.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.6705365720926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenyl-3,4-dihydro-2H-1-benzopyran-3-ol

> <JCHEM_LOGP>
3.0093683019999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.903836063572925

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2782621057932024

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
66.07610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
favan-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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       0.000   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+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  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydro-2-phenyl-2H-1-benzopyran-3-ol	HMDB
3-Flavan-ol	HMDB
3-Flavanol	HMDB
3-Flavanol (mixed isomers)	HMDB

Chemical Formula

C₁₅H₁₄O₂

Average Mass

226.2750 Da

Monoisotopic Mass

226.09938 Da

IUPAC Name

2-phenyl-3,4-dihydro-2H-1-benzopyran-3-ol

Traditional Name

favan-3-ol

CAS Registry Number

Not Available

SMILES

OC1CC2=CC=CC=C2OC1C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H14O2/c16-13-10-12-8-4-5-9-14(12)17-15(13)11-6-2-1-3-7-11/h1-9,13,15-16H,10H2

InChI Key

OEIJRRGCTVHYTH-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
Cinnamomum triplinerve	LOTUS Database	35616633
Malus sylvestris	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
Flavan-3-ol
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyflavonoid (CHEBI:79987 )

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	3.01	ChemAxon
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.08 m³·mol⁻¹	ChemAxon
Polarizability	24.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0252291

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000947

Chemspider ID

2938726

KEGG Compound ID

C15598

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flavan-3-ol

METLIN ID

Not Available

PubChem Compound

3707243

PDB ID

Not Available

ChEBI ID

79987

Good Scents ID

Not Available

References

General References

Okafor JNC, Meyer M, Le Roes-Hill M, Jideani VA: Flavonoid and Phenolic Acid Profiles of Dehulled and Whole Vigna subterranea (L.) Verdc Seeds Commonly Consumed in South Africa. Molecules. 2022 Aug 18;27(16):5265. doi: 10.3390/molecules27165265. [PubMed:36014504 ]
Ren Y, Qin Z, Wang Z, Wei S, Chen H, Zhu T, Liu L, Zhao Y, Ding B, Song W: Condensed tannins from Ulmus pumila L. leaves induce G2/M phase arrest and apoptosis via caspase-cascade activation in TFK-1 cholangiocarcinoma cells. J Food Biochem. 2022 Oct;46(10):e14374. doi: 10.1111/jfbc.14374. Epub 2022 Aug 20. [PubMed:35986624 ]
VanderWeide J, Falchi R, Calderan A, Peterlunger E, Vrhovsek U, Sivilotti P, Sabbatini P: Juxtaposition of the Source-to-Sink Ratio and Fruit Exposure to Solar Radiation on cv. Merlot (Vitis vinifera L.) Berry Phenolics in a Cool versus Warm Growing Region. J Agric Food Chem. 2022 Aug 31;70(34):10429-10442. doi: 10.1021/acs.jafc.2c01528. Epub 2022 Aug 17. [PubMed:35976259 ]
Di Pede G, Mena P, Bresciani L, Almutairi TM, Del Rio D, Clifford MN, Crozier A: Human colonic catabolism of dietary flavan-3-ol bioactives. Mol Aspects Med. 2023 Feb;89:101107. doi: 10.1016/j.mam.2022.101107. Epub 2022 Aug 2. [PubMed:35931563 ]
LOTUS database [Link]

Showing NP-Card for favan-3-ol (NP0197923)

MOL for NP0197923 (favan-3-ol)

3D MOL for NP0197923 (favan-3-ol)

3D SDF for NP0197923 (favan-3-ol)

3D-SDF for NP0197923 (favan-3-ol)

PDB for NP0197923 (favan-3-ol)

3D PDB for NP0197923 (favan-3-ol)

SMILES for NP0197923 (favan-3-ol)

INCHI for NP0197923 (favan-3-ol)

Structure for NP0197923 (favan-3-ol)

3D Structure for NP0197923 (favan-3-ol)