NP-MRD: Showing NP-Card for 7,4'-dihydroxyflavan (NP0147995)

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Record Information

Version

2.0

Created at

2022-09-02 03:41:26 UTC

Updated at

2022-09-02 03:41:26 UTC

NP-MRD ID

NP0147995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,4'-dihydroxyflavan

Description

7,4'-Dihydroxyflavan belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. Thus, 7,4'-dihydroxyflavan is considered to be a flavonoid. 7,4'-dihydroxyflavan is found in Botrytis cinerea, Brosimum acutifolium, Broussonetia kazinoki, Broussonetia papyrifera, Dracaena draco, Soymida febrifuga and Habranthus brachyandrus. 7,4'-dihydroxyflavan was first documented in 2012 (PMID: 22450131). Based on a literature review a small amount of articles have been published on 7,4'-Dihydroxyflavan (PMID: 25142217) (PMID: 27497307) (PMID: 33335132).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.7598   -0.1051   -0.8680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3850   -0.3013   -0.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942   -1.3326   -1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191   -1.5213   -1.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6025   -0.6933   -0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1314   -0.8942   -0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2619   -1.5846    0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7583   -1.5856    0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3218   -0.2225    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4966    0.0822    1.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505    1.3525    1.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073    2.2847    0.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511    3.5527    0.2878 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466    1.9579   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875    0.7030   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5271    0.3531   -0.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2127    0.3430   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5875    0.5383   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1761    0.6639   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897   -2.0068   -2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9445   -2.3397   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210   -1.5379   -1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0679   -2.6453    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2391   -1.1654    1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1772   -2.2426    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0268   -1.9629    1.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -0.6182    1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9603    1.6479    1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942    4.2480   -0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7288    2.6777   -0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5879    1.0054    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394    1.3488    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 17  1  0
 17 18  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  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  2  0
 15 16  1  0
 18  2  1  0
 16  6  1  0
 15  9  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
 17 31  1  0
 18 32  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
M  END


  Mrv1652309022205412D          

 18 20  0  0  1  0            999 V2000
   -2.1434   -2.8875    0.0000 O   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
    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  2  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
    4.2868   -1.6500    0.0000 O   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
    0.0000   -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  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1CCC2=CC=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c16-12-5-1-10(2-6-12)14-8-4-11-3-7-13(17)9-15(11)18-14/h1-3,5-7,9,14,16-17H,4,8H2/t14-/m0/s1

> <INCHI_KEY>
YXMLGIGHGPSEKA-AWEZNQCLSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.924654537121047

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
3.4771412656666665

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.985418184589651

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.312992132885645

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889630779662077

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
68.6764

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,4'-dihydroxyflavan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   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       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       6.668  -0.770   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15    6                                                       
CONECT   17    5   18                                                       
CONECT   18   17    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

(2S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

7,4'-dihydroxyflavan

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1CCC2=CC=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H14O3/c16-12-5-1-10(2-6-12)14-8-4-11-3-7-13(17)9-15(11)18-14/h1-3,5-7,9,14,16-17H,4,8H2/t14-/m0/s1

InChI Key

YXMLGIGHGPSEKA-AWEZNQCLSA-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
Botrytis cinerea	LOTUS Database	35616633
Brosimum acutifolium	LOTUS Database	35616633
Broussonetia kazinoki	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Dracaena draco	LOTUS Database	35616633
Soymida febrifuga	LOTUS Database	35616633
Zephyranthes brachyandra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavan
1-benzopyran
Chromane
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyflavonoid (CHEBI:2246 )
flavans (C09641 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020233 )

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	2.94	ALOGPS
logP	3.48	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.9	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	68.68 m³·mol⁻¹	ChemAxon
Polarizability	25.92 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

C00000950

Chemspider ID

139262

KEGG Compound ID

C09641

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

158280

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Anh DT, Duong TB, Hoang VD: A new chromone from Hymenocallis littoralis Salisb. (Amaryllidaceae). Nat Prod Res. 2014;28(21):1869-72. doi: 10.1080/14786419.2014.951931. Epub 2014 Aug 21. [PubMed:25142217 ]
Xu X, Cheng K, Cheng W, Zhou T, Jiang M, Xu J: Isolation and chatacterization of homoisoflavonoids from Dracaena cochinchinensis and their osteogenic activities in mouse mesenchymal stem cells. J Pharm Biomed Anal. 2016 Sep 10;129:466-472. doi: 10.1016/j.jpba.2016.07.017. Epub 2016 Jul 13. [PubMed:27497307 ]
Nguyen KV, Ho DV, Le NT, Van Phan K, Heinamaki J, Raal A, Nguyen HT: Flavonoids and alkaloids from the rhizomes of Zephyranthes ajax Hort. and their cytotoxicity. Sci Rep. 2020 Dec 17;10(1):22193. doi: 10.1038/s41598-020-78785-2. [PubMed:33335132 ]
Ahn JH, Liu Q, Lee C, Ahn MJ, Yoo HS, Hwang BY, Lee MK: A new pancreatic lipase inhibitor from Broussonetia kanzinoki. Bioorg Med Chem Lett. 2012 Apr 15;22(8):2760-3. doi: 10.1016/j.bmcl.2012.02.088. Epub 2012 Mar 7. [PubMed:22450131 ]
LOTUS database [Link]

Showing NP-Card for 7,4'-dihydroxyflavan (NP0147995)

MOL for NP0147995 (7,4'-dihydroxyflavan)

3D MOL for NP0147995 (7,4'-dihydroxyflavan)

3D SDF for NP0147995 (7,4'-dihydroxyflavan)

3D-SDF for NP0147995 (7,4'-dihydroxyflavan)

PDB for NP0147995 (7,4'-dihydroxyflavan)

3D PDB for NP0147995 (7,4'-dihydroxyflavan)

SMILES for NP0147995 (7,4'-dihydroxyflavan)

INCHI for NP0147995 (7,4'-dihydroxyflavan)

Structure for NP0147995 (7,4'-dihydroxyflavan)

3D Structure for NP0147995 (7,4'-dihydroxyflavan)