NP-MRD: Showing NP-Card for 4'-Hydroxy-7-methoxyflavan (NP0056021)

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Record Information

Version

2.0

Created at

2022-04-28 01:55:06 UTC

Updated at

2022-04-28 01:55:06 UTC

NP-MRD ID

NP0056021

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-Hydroxy-7-methoxyflavan

Description

4'-Hydroxy-7-methoxyflavan, also known as 4-HMF CPD, belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 4'-hydroxy-7-methoxyflavan is considered to be a flavonoid. 4'-Hydroxy-7-methoxyflavan is found in Bauhinia manca, Bauhinia roxburghiana, Crinum asiaticum, Crinum asiaticum var.japonicum , Garcinia dulcis , Genista tricuspidata, Lycoris radiata, Pancratium maritimum, Soymida febrifuga and Stypandra grandis. 4'-Hydroxy-7-methoxyflavan was first documented in 2005 (PMID: 16317657). Based on a literature review a small amount of articles have been published on 4'-Hydroxy-7-methoxyflavan (PMID: 23738449) (PMID: 26230303) (PMID: 18941821).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -5.1722    1.3575    0.9980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9784    0.1115    0.3938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7406   -0.4715    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7425   -1.7111   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087   -2.3166   -0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274   -1.7057   -0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174   -0.4556    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458    0.1225    0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1240    0.1369    0.6296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.5407    0.4070 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2497    0.3407    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245    1.2073    1.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    2.0271    1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4982    2.0166    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6199    2.8354    0.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2300    1.1680   -0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107    0.3333   -0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -1.3223   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -2.4233   -0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1785    1.3123    1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4029    1.5100    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2016    2.1895    0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479   -2.2240   -0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007   -3.2775   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649    1.0894    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -1.2443    1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    1.2159    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8670    2.7154    2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5342    3.7414   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8936    1.1360   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0132   -0.2844   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626   -1.8283   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075   -0.7238   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297   -3.0751   -1.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -2.9624    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 19  1  0
 19 18  1  0
 18 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  8  3  1  0
 17 11  1  0
  7  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
 19 34  1  0
 19 35  1  0
 18 32  1  0
 18 33  1  0
 10 26  1  1
  8 25  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv1652304282203552D          

 19 21  0  0  1  0            999 V2000
   -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  1  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 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
    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
    4.2868   -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
    5.0013    1.2375    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  6  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
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2CC[C@H](OC2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O3/c1-18-14-8-4-12-5-9-15(19-16(12)10-14)11-2-6-13(17)7-3-11/h2-4,6-8,10,15,17H,5,9H2,1H3/t15-/m0/s1

> <INCHI_KEY>
HQIYVJDLRVEGDX-HNNXBMFYSA-N

> <FORMULA>
C16H16O3

> <MOLECULAR_WEIGHT>
256.301

> <EXACT_MASS>
256.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.735233163388873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenol

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.623035321666666

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.47202256654861

> <JCHEM_PKA_STRONGEST_BASIC>
-4.556624518061465

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
73.15870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -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       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  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   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  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18    1   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
4-HMF CPD	MeSH

Chemical Formula

C₁₆H₁₆O₃

Average Mass

256.3010 Da

Monoisotopic Mass

256.10994 Da

IUPAC Name

4-[(2S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenol

Traditional Name

4-[(2S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CC[C@H](OC2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H16O3/c1-18-14-8-4-12-5-9-15(19-16(12)10-14)11-2-6-13(17)7-3-11/h2-4,6-8,10,15,17H,5,9H2,1H3/t15-/m0/s1

InChI Key

HQIYVJDLRVEGDX-HNNXBMFYSA-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
Bauhinia manca	Plant	KNApSAcK
Bauhinia roxburghiana	LOTUS Database	35616633
Crinum asiaticum	LOTUS Database	35616633
Crinum asiaticum var.japonicum	Plant	KNApSAcK
Garcinia dulcis	Plant	KNApSAcK
Genista tricuspidata	LOTUS Database	35616633
Lycoris radiata	LOTUS Database	35616633
Pancratium maritimum	Plant	KNApSAcK
Soymida febrifuga	Plant	KNApSAcK
Stypandra grandis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020234 )

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	3.55	ALOGPS
logP	3.62	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.16 m³·mol⁻¹	ChemAxon
Polarizability	27.74 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008752

Chemspider ID

161360

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185609

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Al-Mekhlafi NA, Shaaria K, Abas F, Jeyaraj EJ, Stanslas J, Khalivulla SI, Lajis NH: New flavan and alkyl alpha,beta-lactones from the stem bark of Horsfieldia superba. Nat Prod Commun. 2013 Apr;8(4):447-51. [PubMed:23738449 ]
Trinh PT, Tri MD, Hien DC, An NH, Minh PN, An PN, Dung le T: A new flavan from the Drynaria bonii H. Christ rhizomes. Nat Prod Res. 2016;30(7):761-7. doi: 10.1080/14786419.2015.1063054. Epub 2015 Jul 31. [PubMed:26230303 ]
Wu ZP, Chen Y, Xia B, Wang M, Dong YF, Feng X: Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida. Lipids. 2009 Jan;44(1):63-70. doi: 10.1007/s11745-008-3246-6. Epub 2008 Oct 22. [PubMed:18941821 ]
Kissling J, Ioset JR, Marston A, Hostettmann K: Bio-guided isolation of cholinesterase inhibitors from the bulbs of Crinum x powellii. Phytother Res. 2005 Nov;19(11):984-7. doi: 10.1002/ptr.1770. [PubMed:16317657 ]

Showing NP-Card for 4'-Hydroxy-7-methoxyflavan (NP0056021)

MOL for NP0056021 (4'-Hydroxy-7-methoxyflavan)

3D MOL for NP0056021 (4'-Hydroxy-7-methoxyflavan)

3D SDF for NP0056021 (4'-Hydroxy-7-methoxyflavan)

3D-SDF for NP0056021 (4'-Hydroxy-7-methoxyflavan)

PDB for NP0056021 (4'-Hydroxy-7-methoxyflavan)

3D PDB for NP0056021 (4'-Hydroxy-7-methoxyflavan)

SMILES for NP0056021 (4'-Hydroxy-7-methoxyflavan)

INCHI for NP0056021 (4'-Hydroxy-7-methoxyflavan)

Structure for NP0056021 (4'-Hydroxy-7-methoxyflavan)

3D Structure for NP0056021 (4'-Hydroxy-7-methoxyflavan)