NP-MRD: Showing NP-Card for 3-Methoxy-8,9-methylenedioxypterocarpan (NP0056683)

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Record Information

Version

2.0

Created at

2022-04-28 02:22:23 UTC

Updated at

2022-04-28 02:22:23 UTC

NP-MRD ID

NP0056683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Methoxy-8,9-methylenedioxypterocarpan

Description

NSC649972 belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. 3-Methoxy-8,9-methylenedioxypterocarpan is found in Baphia nitida , Erycibe expansa , Lathyrus odoratus, Onionis viscosa ssp. breviflora, Ononis viscosa, Ononis viscosa subsp. breviflora , Pterocarpus indicus , Pterocarpus macrocarpus, Pterocarpus osun, Pterocarpus santalinus , Pterocarpus spp., Sophora angustifolia, Sophora flavescens, Sophora subprostrata, Sophora substrata and Swartzia madagascariensis . Based on a literature review very few articles have been published on NSC649972.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 40  0  0  0  0  0  0  0  0999 V2000
    6.4494    0.5522   -0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5457   -0.5407   -0.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -0.2619   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7616    1.0185   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4470    1.3246   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    0.2891   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9350   -1.0027   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2468   -1.2620   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9437   -1.9708   -0.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404   -1.9549    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402   -0.5860    1.0311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9764   -0.3152    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1499   -0.5871    1.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3874   -0.2196    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4276    0.4459   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484    0.7135   -0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0080    0.3486   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6940    0.5068   -0.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200    0.5245    0.2410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7769    0.6936   -0.5245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5156    0.5057    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6940   -0.3814    1.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4495    0.2496   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4766    0.9889    0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613    1.3481   -1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5126    1.8155   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359    2.3557    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478   -2.2943   -0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0126   -2.4314    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1195   -2.6260    1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062   -0.4090    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1464   -1.1123    2.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2905    1.2428   -1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612    1.4626    0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5060    0.0735    0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6027    1.4954    1.1644 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 17  1  0
 17 12  2  0
 12 13  1  0
 13 14  2  0
 14 22  1  0
 22 21  1  0
 21 20  1  0
 20 15  1  0
 15 16  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  8  3  1  0
  7  6  1  0
 11 19  1  0
 16 17  1  0
 15 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 19 34  1  1
 13 32  1  0
 21 35  1  0
 21 36  1  0
 16 33  1  0
 11 31  1  1
 10 29  1  0
 10 30  1  0
  8 28  1  0
M  END


  Mrv1652304282204222D          

 22 26  0  0  1  0            999 V2000
    7.0888    1.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7270    2.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9040    2.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4428    1.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8046    0.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6276    0.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3435    0.1548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205    0.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1586    0.9536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6198    1.6377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1117    2.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3366    2.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655    1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6660    0.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375    1.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    1.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6080    2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1154    2.1824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    1.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.8483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9118    1.4082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3730    2.0923    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
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  6  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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2[C@H]3OC4=C(C=C5OCOC5=C4)[C@H]3COC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O5/c1-18-9-2-3-10-13(4-9)19-7-12-11-5-15-16(21-8-20-15)6-14(11)22-17(10)12/h2-6,12,17H,7-8H2,1H3/t12-,17-/m1/s1

> <INCHI_KEY>
YLZYAUCOYZKLMA-SJKOYZFVSA-N

> <FORMULA>
C17H14O5

> <MOLECULAR_WEIGHT>
298.294

> <EXACT_MASS>
298.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.148895848578924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S)-16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13,15,17-hexaene

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.4360221856666664

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.229144998879641

> <JCHEM_POLAR_SURFACE_AREA>
46.150000000000006

> <JCHEM_REFRACTIVITY>
76.84710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S)-16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13,15,17-hexaene

> <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      13.232   2.736   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.557   4.120   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.021   4.227   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.160   2.950   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.835   1.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.372   1.459   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.974   0.289   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.438   0.396   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.763   1.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.624   3.057   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.675   4.270   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.228   3.743   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.282   2.204   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.977   1.388   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.617   2.111   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.563   3.650   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.868   4.466   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.082   4.074   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.221   2.797   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.170   1.583   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.769   2.629   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.630   3.906   0.000  0.00  0.00           C+0
CONECT    1    2    6   21                                                  
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                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄O₅

Average Mass

298.2940 Da

Monoisotopic Mass

298.08412 Da

IUPAC Name

(1S,12S)-16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13,15,17-hexaene

Traditional Name

(1S,12S)-16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13,15,17-hexaene

CAS Registry Number

Not Available

SMILES

COC1=CC=C2[C@H]3OC4=C(C=C5OCOC5=C4)[C@H]3COC2=C1

InChI Identifier

InChI=1S/C17H14O5/c1-18-9-2-3-10-13(4-9)19-7-12-11-5-15-16(21-8-20-15)6-14(11)22-17(10)12/h2-6,12,17H,7-8H2,1H3/t12-,17-/m1/s1

InChI Key

YLZYAUCOYZKLMA-SJKOYZFVSA-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
Baphia nitida	Plant	KNApSAcK
Erycibe expansa	Plant	KNApSAcK
Lathyrus odoratus	LOTUS Database	35616633
Onionis viscosa ssp. breviflora	-	KNApSAcK
Ononis viscosa	LOTUS Database	35616633
Ononis viscosa subsp. breviflora	Plant	KNApSAcK
Pterocarpus indicus	Plant	KNApSAcK
Pterocarpus macrocarpus	LOTUS Database	35616633
Pterocarpus osun	Plant	KNApSAcK
Pterocarpus santalinus	Plant	KNApSAcK
Pterocarpus spp.	Plant	KNApSAcK
Sophora angustifolia	Plant	KNApSAcK
Sophora flavescens	LOTUS Database	35616633
Sophora subprostrata	Plant	KNApSAcK
Sophora substrata	Plant	KNApSAcK
Swartzia madagascariensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Benzofuran
Coumaran
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	2.94	ALOGPS
logP	2.44	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.85 m³·mol⁻¹	ChemAxon
Polarizability	31.15 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

331375

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

373519

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Methoxy-8,9-methylenedioxypterocarpan (NP0056683)

MOL for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

3D MOL for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

3D SDF for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

3D-SDF for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

PDB for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

3D PDB for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

SMILES for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

INCHI for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

Structure for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)

3D Structure for NP0056683 (3-Methoxy-8,9-methylenedioxypterocarpan)