NP-MRD: Showing NP-Card for 4-(gamma,gamma-Dimethylallyl)-phaseollidin (NP0047256)

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Record Information

Version

2.0

Created at

2022-03-17 20:37:09 UTC

Updated at

2022-03-17 20:37:09 UTC

NP-MRD ID

NP0047256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(gamma,gamma-Dimethylallyl)-phaseollidin

Description

4-(gamma,gamma-Dimethylallyl)-phaseollidin is found in Erythrina burttii, Erythrina eriotriocha, Erythrina latissima, Erythrina lysistemon , Erythrina mildbraedii, Erythrina sigmoidea, Erythrina subumbrans, Erythrina zeyheri, Lespedeza cyrtobotrya and Lespedeza floribunda.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212542D          

 31 34  0  0  0  0            999 V2000
   -4.2723    2.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9868    2.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9868    3.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723    3.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    3.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    2.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8434    3.8736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289    3.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145    3.0486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    1.8110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7013    3.8736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723    4.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    5.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    5.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8434    6.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723    6.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145    2.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145    1.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000    2.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145    2.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145    1.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000    0.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000    0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -0.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -1.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000   -1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289   -1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289    0.9860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289    2.6361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8434    2.2235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8434    1.3985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 30  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 29  1  0  0  0  0
 29  9  1  6  0  0  0
 30 10  1  6  0  0  0
  3 11  1  0  0  0  0
  4 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
 14 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 28  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 29 17  1  0  0  0  0
 30 31  1  0  0  0  0
 31 18  1  0  0  0  0
 29 30  1  0  0  0  0
 18 17  2  0  0  0  0
M  END


  Mrv0541 02241212542D          

 31 34  0  0  0  0            999 V2000
   -4.2723    2.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9868    2.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9868    3.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723    3.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    3.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    2.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8434    3.8736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289    3.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145    3.0486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    1.8110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7013    3.8736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723    4.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    5.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    5.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8434    6.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2723    6.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145    2.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145    1.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000    2.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145    2.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145    1.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000    0.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000    0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -0.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -1.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000   -1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289   -1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289    0.9860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289    2.6361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8434    2.2235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8434    1.3985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 30  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 29  1  0  0  0  0
 29  9  1  6  0  0  0
 30 10  1  6  0  0  0
  3 11  1  0  0  0  0
  4 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
 14 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 28  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 29 17  1  0  0  0  0
 30 31  1  0  0  0  0
 31 18  1  0  0  0  0
 29 30  1  0  0  0  0
 18 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12COC3=C(CC=C(C)C)C(O)=CC=C3[C@]1([H])OC1=C2C=CC(O)=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O4/c1-14(2)5-7-17-21(26)12-10-19-23(17)28-13-20-16-9-11-22(27)18(8-6-15(3)4)24(16)29-25(19)20/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3/t20-,25-/m0/s1

> <INCHI_KEY>
HOGHBEDTLGAJAS-CPJSRVTESA-N

> <FORMULA>
C25H28O4

> <MOLECULAR_WEIGHT>
392.4874

> <EXACT_MASS>
392.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.683735859053606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,10R)-6,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

> <ALOGPS_LOGP>
5.24

> <JCHEM_LOGP>
5.820463339000002

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.598031412817402

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.985475419290314

> <JCHEM_PKA_STRONGEST_BASIC>
-4.597682998266057

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
117.0644

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10R)-6,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.975   4.151   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.309   4.921   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.309   6.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.975   7.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.641   6.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.641   4.921   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.308   7.231   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.974   6.461   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -2.640   5.691   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0      -6.641   3.381   0.000  0.00  0.00           H+0
HETATM   11  O   UNK     0     -10.642   7.231   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -7.975   8.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.641   9.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.641  11.081   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.308  11.851   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.975  11.851   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.640   4.151   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.640   2.611   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.307   4.921   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.027   4.151   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.027   2.611   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.307   1.841   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.307   0.301   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.027  -0.469   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.027  -2.009   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.307  -2.779   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.361  -2.779   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.361   1.841   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.974   4.921   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.308   4.151   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.308   2.611   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1   30    5                                                  
CONECT    7    5    8                                                       
CONECT    8    7   29                                                       
CONECT    9   29                                                            
CONECT   10   30                                                            
CONECT   11    3                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   19   29   18                                                  
CONECT   18   22   31   17                                                  
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   18   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21                                                            
CONECT   29    8    9   17   30                                             
CONECT   30    6   10   31   29                                             
CONECT   31   30   18                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(6AR,11ar-cis)-6a,11a-dihydro-4,10-bis(3-methyl-2-butenyl)-6H-benzofuro(3,2-c)(1)benzopyran-3,9-diol	ChEBI
4-Prenylphaseollidin	ChEBI
4-(g,g-Dimethylallyl)-phaseollidin	Generator
4-(Γ,γ-dimethylallyl)-phaseollidin	Generator

Chemical Formula

C₂₅H₂₈O₄

Average Mass

392.4874 Da

Monoisotopic Mass

392.19876 Da

IUPAC Name

(1R,10R)-6,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

Traditional Name

(1R,10R)-6,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

CAS Registry Number

119269-76-0

SMILES

[H][C@@]12COC3=C(CC=C(C)C)C(O)=CC=C3[C@]1([H])OC1=C2C=CC(O)=C1CC=C(C)C

InChI Identifier

InChI=1S/C25H28O4/c1-14(2)5-7-17-21(26)12-10-19-23(17)28-13-20-16-9-11-22(27)18(8-6-15(3)4)24(16)29-25(19)20/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3/t20-,25-/m0/s1

InChI Key

HOGHBEDTLGAJAS-CPJSRVTESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Erythrina burttii	Plant	KNApSAcK
Erythrina eriotriocha	Plant	KNApSAcK
Erythrina latissima	LOTUS Database	35616633
Erythrina lysistemon	Plant	KNApSAcK
Erythrina mildbraedii	Plant	KNApSAcK
Erythrina sigmoidea	LOTUS Database	35616633
Erythrina subumbrans	Plant	KNApSAcK
Erythrina zeyheri	Plant	KNApSAcK
Lespedeza cyrtobotrya	Plant	KNApSAcK
Lespedeza floribunda	Plant	KNApSAcK
Phaseolus lunatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Benzofuran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:65862 )
pterocarpans (CHEBI:65862 )

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	5.24	ALOGPS
logP	5.82	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.06 m³·mol⁻¹	ChemAxon
Polarizability	43.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

FDB008012

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

21141346

PDB ID

Not Available

ChEBI ID

65862

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4-(gamma,gamma-Dimethylallyl)-phaseollidin (NP0047256)

MOL for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

3D MOL for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

3D SDF for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

3D-SDF for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

PDB for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

3D PDB for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

SMILES for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

INCHI for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

Structure for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)

3D Structure for NP0047256 (4-(gamma,gamma-Dimethylallyl)-phaseollidin)