NP-MRD: Showing NP-Card for Erybraedin A (NP0049254)

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Record Information

Version

2.0

Created at

2022-03-17 21:09:32 UTC

Updated at

2022-03-17 21:09:32 UTC

NP-MRD ID

NP0049254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erybraedin A

Description

Erybraedin A 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. Thus, erybraedin a is considered to be a flavonoid lipid molecule. Erybraedin A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Erybraedin A has been detected, but not quantified in, lima beans and pulses. Erybraedin A is found in Erythrina burttii, Erythrina latissima, Erythrina lysistemon, Erythrina mildbraedii, Erythrina sigmoidea, Erythrina subumbrans, Erythrina zeyheri, Lespedeza cyrtobotrya and Lespedeza floribunda. This could make erybraedin a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310422D          

 29 32  0  0  0  0            999 V2000
    6.3346    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6109    0.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921   -5.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -5.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4163   -0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -4.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926   -0.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -3.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7873    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980   -4.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  2  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 10  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 21 17  2  0  0  0  0
 22 11  1  0  0  0  0
 22 18  2  0  0  0  0
 23 17  1  0  0  0  0
 23 19  2  0  0  0  0
 24 16  2  0  0  0  0
 24 18  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28 13  1  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
M  END


  Mrv0541 05061310422D          

 29 32  0  0  0  0            999 V2000
    6.3346    0.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6109    0.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921   -5.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -5.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4163   -0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -4.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926   -0.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -3.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7873    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980   -4.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  2  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 10  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 21 17  2  0  0  0  0
 22 11  1  0  0  0  0
 22 18  2  0  0  0  0
 23 17  1  0  0  0  0
 23 19  2  0  0  0  0
 24 16  2  0  0  0  0
 24 18  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28 13  1  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2CC=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

> <INCHI_KEY>
HOGHBEDTLGAJAS-UHFFFAOYSA-N

> <FORMULA>
C25H28O4

> <MOLECULAR_WEIGHT>
392.4874

> <EXACT_MASS>
392.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.680919635112815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(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>
9.598031417007714

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.985475419290314

> <JCHEM_PKA_STRONGEST_BASIC>
-4.597682998266057

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
117.06439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erybraedin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.825   1.819   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.207   0.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.652  -9.963   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.987  -9.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.977  -0.844   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.429  -7.592   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.440  -0.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.134  -6.760   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.670   0.531   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.356  -9.130   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    7   14                                                       
CONECT    6    8   15                                                       
CONECT    7    5   17                                                       
CONECT    8    6   18                                                       
CONECT    9   11   16                                                       
CONECT   10   12   19                                                       
CONECT   11    9   22                                                       
CONECT   12   10   21                                                       
CONECT   13   20   28                                                       
CONECT   14    1    2    5                                                  
CONECT   15    3    4    6                                                  
CONECT   16    9   20   24                                                  
CONECT   17    7   21   23                                                  
CONECT   18    8   22   24                                                  
CONECT   19   10   23   25                                                  
CONECT   20   13   16   25                                                  
CONECT   21   12   17   26                                                  
CONECT   22   11   18   27                                                  
CONECT   23   17   19   28                                                  
CONECT   24   16   18   29                                                  
CONECT   25   19   20   29                                                  
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   13   23                                                       
CONECT   29   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(6AR,11ar)-3,9-dihydroxy-4,10-diprenylpterocarpan	HMDB
4-Prenylphaseollidin	HMDB
6a,11a-Dihydro-4,10-bis(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-3,9-diol, 9ci	HMDB

Chemical Formula

C₂₅H₂₈O₄

Average Mass

392.4874 Da

Monoisotopic Mass

392.19876 Da

IUPAC Name

6,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

Traditional Name

erybraedin A

CAS Registry Number

119269-76-0

SMILES

CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2CC=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

InChI Key

HOGHBEDTLGAJAS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Erythrina burttii	LOTUS Database	35616633
Erythrina latissima	LOTUS Database	35616633
Erythrina lysistemon	LOTUS Database	35616633
Erythrina mildbraedii	LOTUS Database	35616633
Erythrina sigmoidea	LOTUS Database	35616633
Erythrina subumbrans	LOTUS Database	35616633
Erythrina zeyheri	LOTUS Database	35616633
Lespedeza cyrtobotrya	LOTUS Database	35616633
Lespedeza floribunda	LOTUS Database	35616633
Phaseolus lunatus	FooDB	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
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

Pterocarpans (LMPK12070044 )

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	44.68 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

HMDB0038872

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018318

KNApSAcK ID

C00010016

Chemspider ID

321822

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

362562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Erybraedin A (NP0049254)

MOL for NP0049254 (Erybraedin A)

3D MOL for NP0049254 (Erybraedin A)

3D SDF for NP0049254 (Erybraedin A)

3D-SDF for NP0049254 (Erybraedin A)

PDB for NP0049254 (Erybraedin A)

3D PDB for NP0049254 (Erybraedin A)

SMILES for NP0049254 (Erybraedin A)

INCHI for NP0049254 (Erybraedin A)

Structure for NP0049254 (Erybraedin A)

3D Structure for NP0049254 (Erybraedin A)