NP-MRD: Showing NP-Card for 7-Hydroxy-3',4'-methylenedioxyflavan (NP0056040)

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Record Information

Version

2.0

Created at

2022-04-28 01:55:53 UTC

Updated at

2022-04-28 01:55:53 UTC

NP-MRD ID

NP0056040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Hydroxy-3',4'-methylenedioxyflavan

Description

7-Hydroxy-3',4'-methylenedioxyflavan, also known as 7-H-MDF, 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-hydroxy-3',4'-methylenedioxyflavan is considered to be a flavonoid. 7-Hydroxy-3',4'-methylenedioxyflavan is found in Iryanthera lancifolia, Habranthus brachyandrus and Zephyranthes flava. 7-Hydroxy-3',4'-methylenedioxyflavan was first documented in 2013 (PMID: 23738449). Based on a literature review a small amount of articles have been published on 7-Hydroxy-3',4'-methylenedioxyflavan (PMID: 33335132) (PMID: 32519564) (PMID: 25431196).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
    3.9311    2.2500    2.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713    1.3414    1.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8472    0.0449    1.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3184   -0.8738    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -0.5200   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926    0.7504   -0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    1.6890    0.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618    1.1573   -0.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.3329   -1.7386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1884   -0.0503   -1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995   -1.3297   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9184   -1.6055   -0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466   -0.6203    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1361    0.6602    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9351    0.9218   -0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599    1.4328    0.8617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9472    0.6141    1.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650   -0.6037    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9330   -0.8350   -2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724   -1.4894   -1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7179    2.8118    2.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6669   -0.2466    2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6963   -1.8872    0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9391    2.6905    0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1572    0.9753   -2.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489   -2.1107   -1.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127   -2.6083   -0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5339    1.9410   -0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9723    1.0156    1.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5022    0.4783    2.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7132   -0.4159   -2.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005   -1.5931   -2.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0456   -2.2518   -0.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293   -2.0664   -1.4820 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 20  1  0
 20 19  1  0
 19  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  9 10  1  0
 10 15  2  0
 15 14  1  0
 14 13  2  0
 13 18  1  0
 18 17  1  0
 17 16  1  0
 13 12  1  0
 12 11  2  0
  7  2  1  0
 11 10  1  0
  6  5  1  0
 16 14  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
 20 33  1  0
 20 34  1  0
 19 31  1  0
 19 32  1  0
  9 25  1  6
  7 24  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 12 27  1  0
 11 26  1  0
M  END

  Mrv1652304282203552D          

 20 23  0  0  1  0            999 V2000
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    4.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    3.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -0.1271    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
  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2CC[C@H](OC2=C1)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c17-12-4-1-10-2-5-13(20-15(10)8-12)11-3-6-14-16(7-11)19-9-18-14/h1,3-4,6-8,13,17H,2,5,9H2/t13-/m0/s1

> <INCHI_KEY>
DGOAORIWKTZFLK-ZDUSSCGKSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.284

> <EXACT_MASS>
270.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.904654008618884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.4039400549999996

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.826385695947208

> <JCHEM_PKA_STRONGEST_BASIC>
-4.508735470910002

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
72.46240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.199   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.199   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.865   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.531   6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   8.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530   9.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.268   8.709   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.173   7.463   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.268   6.217   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.865  -0.237   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
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   19                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13                                                       
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
7-H-MDF	MeSH
7-Hydroxy-3',4'-(methylenedioxy)flavan	MeSH

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2840 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

(2S)-2-(2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

(2S)-2-(2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-7-ol

CAS Registry Number

Not Available

SMILES

OC1=CC=C2CC[C@H](OC2=C1)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C16H14O4/c17-12-4-1-10-2-5-13(20-15(10)8-12)11-3-6-14-16(7-11)19-9-18-14/h1,3-4,6-8,13,17H,2,5,9H2/t13-/m0/s1

InChI Key

DGOAORIWKTZFLK-ZDUSSCGKSA-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
Iryanthera lancifolia	LOTUS Database	35616633
Zephyranthes brachyandra	LOTUS Database	35616633
Zephyranthes flava	Plant	KNApSAcK

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

7-hydroxyflavonoid
Flavan
Chromane
Benzopyran
1-benzopyran
Benzodioxole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Organoheterocyclic compound
Oxacycle
Ether
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020248 )

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	3.16	ALOGPS
logP	3.4	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.83	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.46 m³·mol⁻¹	ChemAxon
Polarizability	27.9 Å³	ChemAxon
Number of Rings	4	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

C00008773

Chemspider ID

409699

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

466078

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 ]
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 ]
Pham TV, Bach HKT, Ho DV, Nguyen BC: Chemical constituents from the Knema globularia fruits and their in vitro cytotoxicity. Nat Prod Res. 2022 Jan;36(1):256-262. doi: 10.1080/14786419.2020.1777416. Epub 2020 Jun 10. [PubMed:32519564 ]
Oluyemisi OO, Oriabure AE, Adekunle AJ, Ramsay KS, Shyyaula S, Choudhary MI: Bioassay-guided isolation of Poliovirus-inhibiting constituents from Zephyranthes candida. Pharm Biol. 2015 Jun;53(6):882-7. doi: 10.3109/13880209.2014.946061. Epub 2014 Nov 28. [PubMed:25431196 ]

Showing NP-Card for 7-Hydroxy-3',4'-methylenedioxyflavan (NP0056040)

MOL for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

3D MOL for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

3D SDF for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

3D-SDF for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

PDB for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

3D PDB for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

SMILES for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

INCHI for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

Structure for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)

3D Structure for NP0056040 (7-Hydroxy-3',4'-methylenedioxyflavan)