NP-MRD: Showing NP-Card for (-)-Homopterocarpin (NP0056680)

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Record Information

Version

2.0

Created at

2022-04-28 02:22:16 UTC

Updated at

2022-04-28 02:22:16 UTC

NP-MRD ID

NP0056680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Homopterocarpin

Description

Homopterocarpin 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. (-)-Homopterocarpin is found in Erycibe expansa , Maackia amurensis , Ononis viscosa, Ononis viscosa subsp. breviflora , Pericopsis angolensis , Pericopsis schliebenii, Platymiscium floribundum, Pterocarpus indicus , Pterocarpus macrocarpus, Pterocarpus spp., Swartzia madagascariensis and Trifolium hybridum . (-)-Homopterocarpin was first documented in 2018 (PMID: 30174522). Based on a literature review a small amount of articles have been published on Homopterocarpin (PMID: 32555159) (PMID: 32495561) (PMID: 30174520) (PMID: 29716873).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    5.6995   -1.7549   -1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6245   -0.6244   -0.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -0.1110    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028    0.9936    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894    1.5305    1.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466    0.9117    0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9980   -0.2079   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2445   -0.7055   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -0.6136   -0.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232   -0.1514    0.7437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5504   -0.0427    0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422   -1.2042    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6776   -1.1068    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2788    0.0757   -0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6096    0.1882   -0.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4646   -0.9292   -0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966    1.2098   -0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395    1.1533    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3529    2.2988    0.0105 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0255    2.0907   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4969    1.2079    0.9492 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0614   -1.7280   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602   -1.8912   -1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802   -2.6489   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2081    1.4859    1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273    2.4077    1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682   -1.5940   -1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0682   -0.8246    1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -2.1343    0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2937   -1.9931    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5286   -0.5962   -0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3640   -1.4962   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2811   -1.5807    0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059    2.1714   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5980    3.0378   -0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    1.5238   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2582    1.6522    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  4  3  1  0
 10 21  1  0
  9  7  1  0
 11 18  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  8 27  1  0
  5 26  1  0
  4 25  1  0
 21 37  1  1
 20 35  1  0
 20 36  1  0
 17 34  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 13 30  1  0
 12 29  1  0
 10 28  1  1
M  END


  Mrv1652304282204222D          

 21 24  0  0  1  0            999 V2000
    5.1672    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382   -0.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.1829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6962    0.5068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1801    1.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521    1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435    1.0079    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
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)[C@H]1COC3=CC(OC)=CC=C3[C@H]1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-18-10-4-6-13-15(7-10)20-9-14-12-5-3-11(19-2)8-16(12)21-17(13)14/h3-8,14,17H,9H2,1-2H3/t14-,17-/m1/s1

> <INCHI_KEY>
VPGIGLKLCFOWDN-RHSMWYFYSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.311

> <EXACT_MASS>
284.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.6293108873668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10S)-5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaene

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
2.655117452333333

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.258805634402126

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
77.54339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10S)-5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaene

> <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       9.645   0.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.953   2.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.415   2.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.570   0.858   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.263  -0.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.800  -0.606   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.418  -1.805   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.881  -1.717   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.188  -0.341   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.033   0.946   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.070   2.147   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.629   1.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.702   0.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.407  -0.768   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.038  -0.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.035   1.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.260   2.308   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.404   2.181   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.699   1.349   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.183   0.594   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.028   1.881   0.000  0.00  0.00           C+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                                                       
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                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20    1   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₄

Average Mass

284.3110 Da

Monoisotopic Mass

284.10486 Da

IUPAC Name

(1S,10S)-5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaene

Traditional Name

(1S,10S)-5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaene

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)[C@H]1COC3=CC(OC)=CC=C3[C@H]1O2

InChI Identifier

InChI=1S/C17H16O4/c1-18-10-4-6-13-15(7-10)20-9-14-12-5-3-11(19-2)8-16(12)21-17(13)14/h3-8,14,17H,9H2,1-2H3/t14-,17-/m1/s1

InChI Key

VPGIGLKLCFOWDN-RHSMWYFYSA-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
Erycibe expansa	Plant	KNApSAcK
Maackia amurensis	Plant	KNApSAcK
Ononis viscosa	LOTUS Database	35616633
Ononis viscosa subsp. breviflora	Plant	KNApSAcK
Pericopsis angolensis	Plant	KNApSAcK
Pericopsis schliebenii	Plant	KNApSAcK
Platymiscium floribundum	LOTUS Database	35616633
Pterocarpus indicus	Plant	KNApSAcK
Pterocarpus macrocarpus	LOTUS Database	35616633
Pterocarpus spp.	Plant	KNApSAcK
Swartzia madagascariensis	Plant	KNApSAcK
Trifolium hybridum	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

Pterocarpan
Isoflavanol
Isoflavan
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
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	3.38	ALOGPS
logP	2.66	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.54 m³·mol⁻¹	ChemAxon
Polarizability	30.63 Å³	ChemAxon
Number of Rings	4	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

C00002536

Chemspider ID

323286

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

364159

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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Showing NP-Card for (-)-Homopterocarpin (NP0056680)

MOL for NP0056680 ((-)-Homopterocarpin)

3D MOL for NP0056680 ((-)-Homopterocarpin)

3D SDF for NP0056680 ((-)-Homopterocarpin)

3D-SDF for NP0056680 ((-)-Homopterocarpin)

PDB for NP0056680 ((-)-Homopterocarpin)

3D PDB for NP0056680 ((-)-Homopterocarpin)

SMILES for NP0056680 ((-)-Homopterocarpin)

INCHI for NP0056680 ((-)-Homopterocarpin)

Structure for NP0056680 ((-)-Homopterocarpin)

3D Structure for NP0056680 ((-)-Homopterocarpin)