NP-MRD: Showing NP-Card for (±)-Sphaerosin (NP0049028)

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Record Information

Version

2.0

Created at

2022-03-17 21:05:59 UTC

Updated at

2022-03-17 21:05:59 UTC

NP-MRD ID

NP0049028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(±)-Sphaerosin

Description

(±)-Sphaerosin, also known as laxifloran, belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, (±)-sphaerosin is considered to be a flavonoid lipid molecule (±)-Sphaerosin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (±)-Sphaerosin has been detected, but not quantified in, several different foods, such as common beans, green beans, hyacinth beans, pulses, and yellow wax beans. (±)-Sphaerosin is found in Endosamara racemosa, Lablab niger, Lonchocarpus laxiflorus , Mucuna poggei and Sphaerophysa salsula. This could make (±)-sphaerosin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061310142D          

 22 24  0  0  0  0            999 V2000
    3.5724    2.0625    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  2  0  0  0  0
 16 13  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20  1  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049028

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-20-16-13(5-6-14(19)17(16)21-2)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3

> <INCHI_KEY>
HHNUTZFOMIAQMX-UHFFFAOYSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.3218

> <EXACT_MASS>
302.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.005051086629095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-2,3-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.8763353459999994

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.376626338188515

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.654108980790125

> <JCHEM_PKA_STRONGEST_BASIC>
-4.428364034807329

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
81.8866

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sphaerosin

> <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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   1.540   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4   10                                                       
CONECT    4    3   12                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7   10   11                                                       
CONECT    8   12   15                                                       
CONECT    9   11   22                                                       
CONECT   10    3    7   15                                                  
CONECT   11    7    9   13                                                  
CONECT   12    4    8   18                                                  
CONECT   13    5   11   16                                                  
CONECT   14    6   17   19                                                  
CONECT   15    8   10   22                                                  
CONECT   16   13   17   20                                                  
CONECT   17   14   16   21                                                  
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20    1   16                                                       
CONECT   21    2   17                                                       
CONECT   22    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(+/-)-sphaerosin	HMDB
7,4'-Dihydroxy-2',3'-dimethoxyisoflavan	HMDB
Laxifloran	HMDB

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3218 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

3-(4-hydroxy-2,3-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

sphaerosin

CAS Registry Number

52305-06-3

SMILES

COC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC

InChI Identifier

InChI=1S/C17H18O5/c1-20-16-13(5-6-14(19)17(16)21-2)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3

InChI Key

HHNUTZFOMIAQMX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Endosamara racemosa	LOTUS Database	35616633
Lablab niger	Plant	KNApSAcK
Lablab purpureus	FooDB	KNAPSACK
Lonchocarpus laxiflorus	Plant	KNApSAcK
Mucuna poggei	Plant	KNApSAcK
Phaseolus vulgaris	FooDB	KNAPSACK
Sphaerophysa salsula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
3p-methoxyisoflavonoid-skeleton
Isoflavanol
Hydroxyisoflavonoid
Isoflavan
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080034 )

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	2.83	ALOGPS
logP	2.88	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.65	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.89 m³·mol⁻¹	ChemAxon
Polarizability	32.01 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

HMDB0038128

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017355

KNApSAcK ID

C00009717

Chemspider ID

153700

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

176471

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (±)-Sphaerosin (NP0049028)

MOL for NP0049028 ((±)-Sphaerosin)

3D MOL for NP0049028 ((±)-Sphaerosin)

3D SDF for NP0049028 ((±)-Sphaerosin)

3D-SDF for NP0049028 ((±)-Sphaerosin)

PDB for NP0049028 ((±)-Sphaerosin)

3D PDB for NP0049028 ((±)-Sphaerosin)

SMILES for NP0049028 ((±)-Sphaerosin)

INCHI for NP0049028 ((±)-Sphaerosin)

Structure for NP0049028 ((±)-Sphaerosin)

3D Structure for NP0049028 ((±)-Sphaerosin)