NP-MRD: Showing NP-Card for Afrormosin (NP0047741)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:11 UTC

Updated at

2022-03-17 20:45:11 UTC

NP-MRD ID

NP0047741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Afrormosin

Description

Alfalone belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, alfalone is considered to be a flavonoid lipid molecule. Alfalone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Alfalone has been detected, but not quantified in, alfalfa and pulses. Afrormosin is found in Afrormosia elata, Amphimas pterocarpoides, Andira inermis , Astragalus clusii, Baptisia arachnifera, Baptisia australis, Baptisia bracteata, Baptisia cinerea, Baptisia lanceolata, Baptisia lecontei, Baptisia megacarpa, Baptisia nuttalliana, Baptisia perfoliata, Baptisia simplicifolia, Baptisia tinctoria , Castanea mollissima , Castanospermum australe , Centrosema haitiense, Centrosema pubescens, Cladrastis kentukea, Cladrastis platycarpa, Cladrastis sikokiana, Dalbergia frutescens, Dipteryx odorata , Gliricidia sepium , Glycyrrhiza glabra , Glycyrrhiza pallidiflora, Medicago truncatula, Millettia dielsiana, Millettia reticulata , Myrocarpus fastigiatus, Myroxylon balsamum , Myroxylon peruiferum , Onobrychis viciifolia , Pericopsis elata , Pericopsis mooniana, Pterodon apparicioi, Rhodomyrtus tomentosa , Spatholobus suberectus , Taverniera abyssinica , Wisteria brachybotrys and Wisteria floribunda . This could make alfalone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061310402D          

 22 24  0  0  0  0            999 V2000
    6.4302    4.5375    0.0000 C   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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    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
    1.4289    0.8250    0.0000 C   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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    3.5724    2.0625    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
    2.1434    1.2375    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 16 14  2  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 17  2  0  0  0  0
 20  1  1  0  0  0  0
 20 11  1  0  0  0  0
 21  2  1  0  0  0  0
 21 16  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=CC(OC)=C(O)C=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)13-9-22-15-8-16(21-2)14(18)7-12(15)17(13)19/h3-9,18H,1-2H3

> <INCHI_KEY>
CQULNEWSZBPFNL-UHFFFAOYSA-N

> <FORMULA>
C17H14O5

> <MOLECULAR_WEIGHT>
298.2901

> <EXACT_MASS>
298.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.920928295031473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
2.7186605016666663

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.603620723179315

> <JCHEM_PKA_STRONGEST_BASIC>
-4.500986979184478

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
80.6475

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alfalone

> <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      12.003   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7   12   14                                                       
CONECT    8   15   16                                                       
CONECT    9   13   22                                                       
CONECT   10    3    4   13                                                  
CONECT   11    5    6   20                                                  
CONECT   12    7   15   17                                                  
CONECT   13    9   10   17                                                  
CONECT   14    7   16   18                                                  
CONECT   15    8   12   22                                                  
CONECT   16    8   14   21                                                  
CONECT   17   12   13   19                                                  
CONECT   18   14                                                            
CONECT   19   17                                                            
CONECT   20    1   11                                                       
CONECT   21    2   16                                                       
CONECT   22    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-4',7-dimethoxyisoflavone	HMDB
6-Hydroxy-7,4'-dimethoxyisoflavone	HMDB

Chemical Formula

C₁₇H₁₄O₅

Average Mass

298.2901 Da

Monoisotopic Mass

298.08412 Da

IUPAC Name

6-hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

alfalone

CAS Registry Number

550-79-8

SMILES

COC1=CC=C(C=C1)C1=COC2=CC(OC)=C(O)C=C2C1=O

InChI Identifier

InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)13-9-22-15-8-16(21-2)14(18)7-12(15)17(13)19/h3-9,18H,1-2H3

InChI Key

CQULNEWSZBPFNL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Afrormosia elata	Plant	KNApSAcK
Amphimas pterocarpoides	Plant	KNApSAcK
Andira inermis	Plant	KNApSAcK
Astragalus clusii	Plant	KNApSAcK
Baptisia arachnifera	Plant	KNApSAcK
Baptisia australis	Plant	KNApSAcK
Baptisia bracteata	Plant	KNApSAcK
Baptisia cinerea	Plant	KNApSAcK
Baptisia lanceolata	Plant	KNApSAcK
Baptisia lecontei	Plant	KNApSAcK
Baptisia megacarpa	Plant	KNApSAcK
Baptisia nuttalliana	Plant	KNApSAcK
Baptisia perfoliata	Plant	KNApSAcK
Baptisia simplicifolia	Plant	KNApSAcK
Baptisia tinctoria	Plant	KNApSAcK
Castanea mollissima	Plant	KNApSAcK
Castanospermum australe	Plant	KNApSAcK
Centrosema haitiense	Plant	KNApSAcK
Centrosema pubescens	Plant	KNApSAcK
Cladrastis kentukea	Plant	KNApSAcK
Cladrastis platycarpa	Plant	KNApSAcK
Cladrastis sikokiana	Plant	KNApSAcK
Dalbergia frutescens	Plant	KNApSAcK
Dipteryx odorata	Plant	KNApSAcK
Gliricidia sepium	Plant	KNApSAcK
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza pallidiflora	Plant	KNApSAcK
Medicago sativa	FooDB	KNAPSACK
Medicago truncatula	Plant	KNApSAcK
Millettia dielsiana	Plant	KNApSAcK
Millettia reticulata	Plant	KNApSAcK
Myrocarpus fastigiatus	Plant	KNApSAcK
Myroxylon balsamum	Plant	KNApSAcK
Myroxylon peruiferum	Plant	KNApSAcK
Onobrychis viciifolia	Plant	KNApSAcK
Pericopsis elata	Plant	KNApSAcK
Pericopsis mooniana	Plant	KNApSAcK
Pisum sativum	FooDB	KNAPSACK
Pterodon apparicioi	Plant	KNApSAcK
Rhodomyrtus tomentosa	Plant	KNApSAcK
Spatholobus suberectus	Plant	KNApSAcK
Taverniera abyssinica	Plant	KNApSAcK
Wisteria brachybotrys	Plant	KNApSAcK
Wisteria floribunda	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylisoflavones

Alternative Parents

Substituents

4p-o-methylisoflavone
7-o-methylisoflavone
Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050105 )

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	3.51	ALOGPS
logP	2.72	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.6	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.65 m³·mol⁻¹	ChemAxon
Polarizability	30.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038811

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018237

KNApSAcK ID

C00009850

Chemspider ID

10289904

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12132870

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Afrormosin (NP0047741)

MOL for NP0047741 (Afrormosin)

3D MOL for NP0047741 (Afrormosin)

3D SDF for NP0047741 (Afrormosin)

3D-SDF for NP0047741 (Afrormosin)

PDB for NP0047741 (Afrormosin)

3D PDB for NP0047741 (Afrormosin)

SMILES for NP0047741 (Afrormosin)

INCHI for NP0047741 (Afrormosin)

Structure for NP0047741 (Afrormosin)

3D Structure for NP0047741 (Afrormosin)