NP-MRD: Showing NP-Card for Flavan-3,4-diol (NP0083999)

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Record Information

Version

2.0

Created at

2022-04-29 04:52:15 UTC

Updated at

2022-04-29 04:52:15 UTC

NP-MRD ID

NP0083999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Flavan-3,4-diol

Description

Flavan-3,4-diol 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. Flavan-3,4-diol is found in Glycine max and Terminalia alata. Flavan-3,4-diol was first documented in 2011 (PMID: 21412691). Based on a literature review a small amount of articles have been published on flavan-3,4-diol (PMID: 35306369) (PMID: 35263118) (PMID: 29463813) (PMID: 25894212).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.9072   -2.4828    0.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5364   -1.2783    0.7416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1910   -0.1373    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5078    0.1147    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1458    1.1803   -0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5189    2.0149   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994    1.7542   -1.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5324    0.6772   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186    0.3970   -1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.6035   -0.4913 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9114   -0.0671   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0146   -0.8327   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2905   -0.3527   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138    0.9034    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4022    1.6603    0.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    1.1917    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366   -1.1755    0.7603 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4534   -2.4937    0.9071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075   -3.1235    0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135   -1.3357    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0249   -0.5235    1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1995    1.4130    0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515    2.8552   -1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6419    2.3758   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6380   -1.4339   -1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -1.8277   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1203   -1.0010   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5268    1.2814    0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574    2.6403    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400    1.7801    0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624   -0.5990    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670   -2.9717    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17  2  1  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 16 11  1  0
  8  3  1  0
 18 32  1  0
 17 31  1  1
  2 20  1  1
  1 19  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
 10 25  1  6
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1652304292206522D          

 18 20  0  0  0  0            999 V2000
    1.4289   -2.4750    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
    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 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
    0.0000    0.0000    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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    0.8250    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  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  5 12  1  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 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083999

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,13-17H

> <INCHI_KEY>
XIMADJWJJOMVID-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.594528594254747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
2.0903721549999994

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.201452071395813

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.738300693800287

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6043921322858354

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
67.28360000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leucoanthocyanidin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   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  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   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
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    5   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13    2                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₃

Average Mass

242.2740 Da

Monoisotopic Mass

242.09429 Da

IUPAC Name

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

Traditional Name

leucoanthocyanidin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H14O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,13-17H

InChI Key

XIMADJWJJOMVID-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, 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
Glycine max	Plant	KNApSAcK
Terminalia alata	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
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
1,2-diol
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	1.85	ALOGPS
logP	2.09	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.28 m³·mol⁻¹	ChemAxon
Polarizability	25.59 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

C00053174

Chemspider ID

4477408

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leucoanthocyanidin

METLIN ID

Not Available

PubChem Compound

5318979

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhong T, Li M, Wu H, Wang D, Liu J, Xu Y, Fan Y: Novel Flavan-3,4-diol vernicidin B from Toxicodendron Vernicifluum (Anacardiaceae) as potent antioxidant via IL-6/Nrf2 cross-talks pathways. Phytomedicine. 2022 Jun;100:154041. doi: 10.1016/j.phymed.2022.154041. Epub 2022 Mar 11. [PubMed:35306369 ]
Lee TH, Hong SM, Yoon DH, Kim SY, Kim CS, Lee KR: Procyanidins and Phlobatannins from the Twigs of Rosa multiflora and Their Neuroprotective Activity. J Nat Prod. 2022 Apr 22;85(4):917-926. doi: 10.1021/acs.jnatprod.1c01033. Epub 2022 Mar 9. [PubMed:35263118 ]
Toden S, Ravindranathan P, Gu J, Cardenas J, Yuchang M, Goel A: Oligomeric proanthocyanidins (OPCs) target cancer stem-like cells and suppress tumor organoid formation in colorectal cancer. Sci Rep. 2018 Feb 20;8(1):3335. doi: 10.1038/s41598-018-21478-8. [PubMed:29463813 ]
Joycharat N, Boonma C, Thammavong S, Yingyongnarongkul BE, Limsuwan S, Voravuthikunchai SP: Chemical constituents and biological activities of Albizia myriophylla wood. Pharm Biol. 2016;54(1):62-73. doi: 10.3109/13880209.2015.1014920. Epub 2015 Apr 20. [PubMed:25894212 ]
Ferreira D, Coleman CM: Towards the synthesis of proanthocyanidins: half a century of innovation. Planta Med. 2011 Jul;77(11):1071-85. doi: 10.1055/s-0030-1270908. Epub 2011 Mar 16. [PubMed:21412691 ]

Showing NP-Card for Flavan-3,4-diol (NP0083999)

MOL for NP0083999 (Flavan-3,4-diol)

3D MOL for NP0083999 (Flavan-3,4-diol)

3D SDF for NP0083999 (Flavan-3,4-diol)

3D-SDF for NP0083999 (Flavan-3,4-diol)

PDB for NP0083999 (Flavan-3,4-diol)

3D PDB for NP0083999 (Flavan-3,4-diol)

SMILES for NP0083999 (Flavan-3,4-diol)

INCHI for NP0083999 (Flavan-3,4-diol)

Structure for NP0083999 (Flavan-3,4-diol)

3D Structure for NP0083999 (Flavan-3,4-diol)