NP-MRD: Showing NP-Card for 12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol (NP0248430)

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Record Information

Version

2.0

Created at

2022-09-07 10:41:49 UTC

Updated at

2022-09-07 10:41:49 UTC

NP-MRD ID

NP0248430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol

Description

12-[5-(7-Hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphene-9,12a-diol belongs to the class of organic compounds known as rotenoids. These are phenolic compounds containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many rotenoids contain an additional ring, e.G. Rotenone. They are isoflavonoids characterized by the presence of an extra carbon atom in an additional heterocyclic ring. 12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol is found in Gliricidia sepium. Based on a literature review very few articles have been published on 12-[5-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphene-9,12a-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072212412D          

 41 47  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072212412D          

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    1.4120   -6.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221   -5.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922   -5.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -5.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -4.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -4.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -3.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -4.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -2.5302    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 24 34  1  0  0  0  0
 23 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 21 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 20 40  1  0  0  0  0
  6 40  1  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(OCC3OC4=CC(O)=CC=C4C(C4=CC(=CC=C4OC)C4COC5=CC(O)=CC=C5C4)C23O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H30O8/c1-37-23-7-9-26-30(15-23)40-17-31-33(26,36)32(24-8-6-22(35)14-29(24)41-31)25-12-18(4-10-27(25)38-2)20-11-19-3-5-21(34)13-28(19)39-16-20/h3-10,12-15,20,31-32,34-36H,11,16-17H2,1-2H3

> <INCHI_KEY>
AAYNXSSLTTZFMB-UHFFFAOYSA-N

> <FORMULA>
C33H30O8

> <MOLECULAR_WEIGHT>
554.595

> <EXACT_MASS>
554.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
57.625760920523376

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-[5-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphene-9,12a-diol

> <JCHEM_LOGP>
5.005807135666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.960502777282914

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.30704686055898

> <JCHEM_PKA_STRONGEST_BASIC>
-3.922622242579629

> <JCHEM_POLAR_SURFACE_AREA>
106.84000000000002

> <JCHEM_REFRACTIVITY>
150.8551

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
12-[5-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6H-5,7-dioxatetraphene-9,12a-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.140  -5.887   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.644  -4.432   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.677  -0.940   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.709  -1.522   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.750  -3.268   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.197  -5.887   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.685  -6.178   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.181  -7.633   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -7.924   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.660  -6.760   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.148  -7.051   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.644  -8.507   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.132  -8.798   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.628 -10.253   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.115 -10.544   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.636 -11.417   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.148 -11.126   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.652  -9.671   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.164  -9.380   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.189  -8.798   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.701  -8.507   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.205  -7.051   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.726  -7.924   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.189  -4.723   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   40                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   40                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21   40                                                  
CONECT   21   20   22   37                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   35                                                  
CONECT   24   23   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33   24                                                       
CONECT   35   23   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   21   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   20    6   11   41                                             
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₀O₈

Average Mass

554.5950 Da

Monoisotopic Mass

554.19407 Da

IUPAC Name

12-[5-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphene-9,12a-diol

Traditional Name

12-[5-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6H-5,7-dioxatetraphene-9,12a-diol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(OCC3OC4=CC(O)=CC=C4C(C4=CC(=CC=C4OC)C4COC5=CC(O)=CC=C5C4)C23O)=C1

InChI Identifier

InChI=1S/C33H30O8/c1-37-23-7-9-26-30(15-23)40-17-31-33(26,36)32(24-8-6-22(35)14-29(24)41-31)25-12-18(4-10-27(25)38-2)20-11-19-3-5-21(34)13-28(19)39-16-20/h3-10,12-15,20,31-32,34-36H,11,16-17H2,1-2H3

InChI Key

AAYNXSSLTTZFMB-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, 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
Gliricidia sepium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenoids. These are phenolic compounds containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many rotenoids contain an additional ring, e.G. Rotenone. They are isoflavonoids characterized by the presence of an extra carbon atom in an additional heterocyclic ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenoids

Alternative Parents

Substituents

Chromeno-3,4b-chromene
4p-methoxyisoflavonoid
Rotenoid
Hydroxyisoflavonoid
Isoflavanol
Neolignan skeleton
Isoflavan
Neoflavan
Chromane
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
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	5.01	ChemAxon
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	150.86 m³·mol⁻¹	ChemAxon
Polarizability	57.63 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85183418

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol (NP0248430)

MOL for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

3D MOL for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

3D SDF for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

3D-SDF for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

PDB for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

3D PDB for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

SMILES for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

INCHI for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

Structure for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)

3D Structure for NP0248430 (12-[5-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6h-5,7-dioxatetraphene-9,12a-diol)