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Showing NP-Card for 7,4'-Dihydroxy-8-methylflavan (NP0050580)

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Record Information
Version2.0
Created at2022-04-27 21:57:54 UTC
Updated at2022-04-27 21:57:54 UTC
NP-MRD IDNP0050580
Secondary Accession NumbersNone
Natural Product Identification
Common Name7,4'-Dihydroxy-8-methylflavan
Description7,4'-Dihydroxy-8-methylflavan 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'-dihydroxy-8-methylflavan is considered to be a flavonoid. 7,4'-Dihydroxy-8-methylflavan is found in Botrytis cinerea, Dracaena cochinchinensis, Dracaena draco , Hymenocallis littoralis, Narcissus pseudonarcissus and Soymida febrifuga . 7,4'-Dihydroxy-8-methylflavan was first documented in 2016 (PMID: 27497307). Based on a literature review a small amount of articles have been published on 7,4'-Dihydroxy-8-methylflavan (PMID: 33335132) (PMID: 28597686).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050580 (7,4'-Dihydroxy-8-methylflavan)


  Mrv1652304272223572D          

 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
    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  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
  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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  6  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
 15 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
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3D MOL for NP0050580 (7,4'-Dihydroxy-8-methylflavan)

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3D SDF for NP0050580 (7,4'-Dihydroxy-8-methylflavan)

  Mrv1652304272223572D          

 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
    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  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
  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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  6  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
 15 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2O[C@@H](CCC2=CC=C1O)C1=CC=C(O)C=C1

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

> <INCHI_KEY>
GDHZZZRERDPSTA-HNNXBMFYSA-N

> <FORMULA>
C16H16O3

> <MOLECULAR_WEIGHT>
256.301

> <EXACT_MASS>
256.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.553116221017707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(4-hydroxyphenyl)-8-methyl-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.9905626549999993

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.318508857161797

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.405306587577169

> <JCHEM_PKA_STRONGEST_BASIC>
-4.885338513145726

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
73.7176

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,4'-dihydroxy-8-methylflavan

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050580 (7,4'-Dihydroxy-8-methylflavan)
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PDB for NP0050580 (7,4'-Dihydroxy-8-methylflavan)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-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  C   UNK     0       0.000   1.540   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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

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3D PDB for NP0050580 (7,4'-Dihydroxy-8-methylflavan)
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SMILES for NP0050580 (7,4'-Dihydroxy-8-methylflavan)
CC1=C2O[C@@H](CCC2=CC=C1O)C1=CC=C(O)C=C1
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INCHI for NP0050580 (7,4'-Dihydroxy-8-methylflavan)
InChI=1S/C16H16O3/c1-10-14(18)8-4-12-5-9-15(19-16(10)12)11-2-6-13(17)7-3-11/h2-4,6-8,15,17-18H,5,9H2,1H3/t15-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC16H16O3
Average Mass256.3010 Da
Monoisotopic Mass256.10994 Da
IUPAC Name(2S)-2-(4-hydroxyphenyl)-8-methyl-3,4-dihydro-2H-1-benzopyran-7-ol
Traditional Name7,4'-dihydroxy-8-methylflavan
CAS Registry NumberNot Available
SMILES
CC1=C2O[C@@H](CCC2=CC=C1O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C16H16O3/c1-10-14(18)8-4-12-5-9-15(19-16(10)12)11-2-6-13(17)7-3-11/h2-4,6-8,15,17-18H,5,9H2,1H3/t15-/m0/s1
InChI KeyGDHZZZRERDPSTA-HNNXBMFYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Botrytis cinereaLOTUS Database
Dracaena cochinchinensisLOTUS Database
Dracaena dracoPlant
Hymenocallis littoralisLOTUS Database
Narcissus pseudonarcissusPlant
Soymida febrifugaPlant
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassHydroxyflavonoids  
Direct Parent7-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.17ALOGPS
logP3.99ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.72 m³·mol⁻¹ChemAxon
Polarizability27.55 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000953  
Chemspider ID390813  
KEGG Compound IDC09650  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442361  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. 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  ] 
  3. Li FX, Wang H, Gai CJ, Chen HQ, Li W, Mei WL, Dai HF: Three new flavanoids from artificially induced dragon's blood of Dracaena cambodiana. J Asian Nat Prod Res. 2018 Jan;20(1):55-61. doi: 10.1080/10286020.2017.1322583. Epub 2017 Jun 9. [PubMed:28597686  ]