NP-MRD: Showing NP-Card for Pumilaisoflavone B (NP0056909)

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Record Information

Version

2.0

Created at

2022-04-28 02:30:55 UTC

Updated at

2022-04-28 02:30:55 UTC

NP-MRD ID

NP0056909

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pumilaisoflavone B

Description

(2S)-6-{3,5-dimethoxy-4-[(2-methylbut-3-en-2-yl)oxy]phenyl}-4-hydroxy-2-(prop-1-en-2-yl)-2H,3H,5H-furo[3,2-g]chromen-5-one belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Pumilaisoflavone B is found in Tephrosia pumila . Based on a literature review very few articles have been published on (2S)-6-{3,5-dimethoxy-4-[(2-methylbut-3-en-2-yl)oxy]phenyl}-4-hydroxy-2-(prop-1-en-2-yl)-2H,3H,5H-furo[3,2-g]chromen-5-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204302D          

 34 37  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  1 31  1  0  0  0  0
 30 32  1  1  0  0  0
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M  END

     RDKit          3D

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    5.1303   -1.0021   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8034    0.2055    0.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936    0.6145    0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1640    1.8306    0.9793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694   -0.1696   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1590    0.2512   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227    1.3664    0.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270    0.7907    0.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
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 21 50  1  0
M  END


  Mrv1652304282204302D          

 34 37  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0056909

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC(C)(C)C=C)C1=COC2=CC3=C(C[C@H](O3)C(C)=C)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O7/c1-8-27(4,5)34-26-21(30-6)9-15(10-22(26)31-7)17-13-32-20-12-19-16(11-18(33-19)14(2)3)24(28)23(20)25(17)29/h8-10,12-13,18,28H,1-2,11H2,3-7H3/t18-/m0/s1

> <INCHI_KEY>
XUNJCHOQUWRGCB-SFHVURJKSA-N

> <FORMULA>
C27H28O7

> <MOLECULAR_WEIGHT>
464.514

> <EXACT_MASS>
464.183503242

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.56007188955142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-6-{3,5-dimethoxy-4-[(2-methylbut-3-en-2-yl)oxy]phenyl}-4-hydroxy-2-(prop-1-en-2-yl)-2H,3H,5H-furo[3,2-g]chromen-5-one

> <ALOGPS_LOGP>
5.03

> <JCHEM_LOGP>
5.555986158000001

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.491122774394739

> <JCHEM_PKA_STRONGEST_BASIC>
-4.295730002292976

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
128.21810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-6-{3,5-dimethoxy-4-[(2-methylbut-3-en-2-yl)oxy]phenyl}-4-hydroxy-2-(prop-1-en-2-yl)-2H,3H-furo[3,2-g]chromen-5-one

> <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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.875   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.795   6.160   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.245   0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.015   2.104   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.015  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4   28                                                  
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   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   24   25                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   21                                                            
CONECT   26   14   27                                                       
CONECT   27   26                                                            
CONECT   28    3                                                            
CONECT   29    2   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30    1                                                       
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₇

Average Mass

464.5140 Da

Monoisotopic Mass

464.18350 Da

IUPAC Name

(2S)-6-{3,5-dimethoxy-4-[(2-methylbut-3-en-2-yl)oxy]phenyl}-4-hydroxy-2-(prop-1-en-2-yl)-2H,3H,5H-furo[3,2-g]chromen-5-one

Traditional Name

(2S)-6-{3,5-dimethoxy-4-[(2-methylbut-3-en-2-yl)oxy]phenyl}-4-hydroxy-2-(prop-1-en-2-yl)-2H,3H-furo[3,2-g]chromen-5-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC(C)(C)C=C)C1=COC2=CC3=C(C[C@H](O3)C(C)=C)C(O)=C2C1=O

InChI Identifier

InChI=1S/C27H28O7/c1-8-27(4,5)34-26-21(30-6)9-15(10-22(26)31-7)17-13-32-20-12-19-16(11-18(33-19)14(2)3)24(28)23(20)25(17)29/h8-10,12-13,18,28H,1-2,11H2,3-7H3/t18-/m0/s1

InChI Key

XUNJCHOQUWRGCB-SFHVURJKSA-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
Tephrosia pumila	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
3p-methoxyisoflavone
Furanoisoflavonoid skeleton
Isoflavone
Hydroxyisoflavonoid
Furanochromone
Chromone
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Coumaran
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	5.03	ALOGPS
logP	5.56	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	7.49	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.22 m³·mol⁻¹	ChemAxon
Polarizability	50.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162981635

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pumilaisoflavone B (NP0056909)

MOL for NP0056909 (Pumilaisoflavone B)

3D MOL for NP0056909 (Pumilaisoflavone B)

3D SDF for NP0056909 (Pumilaisoflavone B)

3D-SDF for NP0056909 (Pumilaisoflavone B)

PDB for NP0056909 (Pumilaisoflavone B)

3D PDB for NP0056909 (Pumilaisoflavone B)

SMILES for NP0056909 (Pumilaisoflavone B)

INCHI for NP0056909 (Pumilaisoflavone B)

Structure for NP0056909 (Pumilaisoflavone B)

3D Structure for NP0056909 (Pumilaisoflavone B)