NP-MRD: Showing NP-Card for (6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan (NP0062619)

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Record Information

Version

2.0

Created at

2022-04-28 07:13:48 UTC

Updated at

2022-04-28 07:13:48 UTC

NP-MRD ID

NP0062619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan

Description

(1R,13R)-6,6-dimethyl-7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]Icosa-2(10),3,8,14,16,18-hexaene 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. (6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan is found in Oroxylum indicum . Based on a literature review very few articles have been published on (1R,13R)-6,6-dimethyl-7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]Icosa-2(10),3,8,14,16,18-hexaene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -4.8119    0.4039   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4939   -0.1177   -0.0761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7921   -0.3380    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5952    0.8721    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449    0.2969    0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588    0.8198    0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553    0.0478    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -1.2547   -0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313   -1.7685   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3735   -0.9940   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208   -1.3136   -0.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1974   -1.9463   -0.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3368   -1.8297    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4808   -0.4672    1.1041 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7986    0.0711    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0815   -0.0548    1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1650    0.5589    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9218    1.3087   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.4351   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590    0.8211   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811    0.7815   -0.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5308    0.5552    0.5221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1451    1.4588   -1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6779   -0.1549   -1.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9253    0.3307   -2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6180   -0.5435   -0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0558    0.5583    1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7223   -1.2375    1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6803    1.8917    0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    0.8550    1.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8519    1.8382    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373   -2.7913   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051   -2.5772    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2217   -2.1221   -0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3889   -0.5097    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2837   -0.6495    2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1737    0.4655    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7247    1.8135   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4442    2.0298   -1.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747    1.4566    1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 22  7  1  0
  7  6  2  0
 11  2  1  0
  7  8  1  0
  6  5  1  0
 15 14  1  0
 15 20  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  1
 22 40  1  1
 19 39  1  0
 18 38  1  0
 17 37  1  0
 16 36  1  0
  6 31  1  0
M  END


  Mrv1652304282209132D          

 22 26  0  0  1  0            999 V2000
    5.1294    0.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495    0.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    0.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053    0.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7853    1.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973    1.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532    2.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4411    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612    1.1870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6933    0.5565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2581   -0.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570    0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7744   -0.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318   -0.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6546    1.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3971    0.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1836    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9540    0.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7223   -0.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9972    0.3114    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
 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
  9 17  1  6  0  0  0
 12 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC2=C(O1)C=C1OC[C@@H]3[C@@H](OC4=CC=CC=C34)C1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O3/c1-19(2)9-11-7-13-17(8-16(11)22-19)20-10-14-12-5-3-4-6-15(12)21-18(13)14/h3-8,14,18H,9-10H2,1-2H3/t14-,18-/m0/s1

> <INCHI_KEY>
IJFVPUHMYGBKPS-KSSFIOAISA-N

> <FORMULA>
C19H18O3

> <MOLECULAR_WEIGHT>
294.35

> <EXACT_MASS>
294.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.777884732790774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,13R)-6,6-dimethyl-7,11,20-trioxapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,19}]icosa-2,4(8),9,14,16,18-hexaene

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
3.5498289173333326

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.404317699276416

> <JCHEM_POLAR_SURFACE_AREA>
27.69

> <JCHEM_REFRACTIVITY>
83.44680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13R)-6,6-dimethyl-7,11,20-trioxapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,19}]icosa-2,4(8),9,14,16,18-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       9.575   1.854   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.052   0.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.536   0.134   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.543   1.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.066   2.759   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.582   3.031   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.073   3.936   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.557   3.664   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.034   2.216   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.027   1.039   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.215  -0.269   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.720   0.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.445  -0.766   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.059  -0.095   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.052   1.441   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.222   2.306   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.608   1.635   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.269  -0.539   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.543   0.325   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.114   1.805   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.548  -0.841   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.061   0.581   0.000  0.00  0.00           C+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3   18                                                  
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   17                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   12                                                  
CONECT   18    2   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19    1                                                       
CONECT   21   19                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₈O₃

Average Mass

294.3500 Da

Monoisotopic Mass

294.12559 Da

IUPAC Name

(1R,13R)-6,6-dimethyl-7,11,20-trioxapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,19}]icosa-2,4(8),9,14,16,18-hexaene

Traditional Name

(1R,13R)-6,6-dimethyl-7,11,20-trioxapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,19}]icosa-2,4(8),9,14,16,18-hexaene

CAS Registry Number

Not Available

SMILES

CC1(C)CC2=C(O1)C=C1OC[C@@H]3[C@@H](OC4=CC=CC=C34)C1=C2

InChI Identifier

InChI=1S/C19H18O3/c1-19(2)9-11-7-13-17(8-16(11)22-19)20-10-14-12-5-3-4-6-15(12)21-18(13)14/h3-8,14,18H,9-10H2,1-2H3/t14-,18-/m0/s1

InChI Key

IJFVPUHMYGBKPS-KSSFIOAISA-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
Oroxylum indicum	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
Benzopyran
1-benzopyran
Coumaran
Benzofuran
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	4.36	ALOGPS
logP	3.55	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.45 m³·mol⁻¹	ChemAxon
Polarizability	32.78 Å³	ChemAxon
Number of Rings	5	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

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Chemspider ID

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KEGG Compound ID

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METLIN ID

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PubChem Compound

15867393

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References

General References

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Showing NP-Card for (6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan (NP0062619)

MOL for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

3D MOL for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

3D SDF for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

3D-SDF for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

PDB for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

3D PDB for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

SMILES for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

INCHI for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

Structure for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)

3D Structure for NP0062619 ((6aR,11aR)-5',5'-Dimethyl-4',5'-dihydrofurano[2',3':3:2]pterocarpan)