NP-MRD: Showing NP-Card for Betavulgarin (NP0047564)

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Record Information

Version

2.0

Created at

2022-03-17 20:42:14 UTC

Updated at

2022-03-17 20:42:14 UTC

NP-MRD ID

NP0047564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Betavulgarin

Description

Betavulgarin is found in Baptisia spp., Beta corolliflora, Beta lomatogona, Beta procumbens, Beta trigyna, Cercospora beticola, Cotoneaster pannosa, Dalbergia spp., Dianthus spp., Iris tenuifolia, Iris tingitana and Trifolium spp.. Betavulgarin was first documented in 1994 (PMID: 7765684).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216182D          

 23 26  0  0  0  0            999 V2000
    0.7008    0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -2.2682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833   -3.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -3.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    3.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857    1.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1857   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  2  0  0  0  0
  4 22  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 15 16  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OCOC2=CC2=C1C(=O)C(=CO2)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/c1-20-17-14-12(6-13-16(17)23-8-22-13)21-7-10(15(14)19)9-4-2-3-5-11(9)18/h2-7,18H,8H2,1H3

> <INCHI_KEY>
NDVRQFZUJRMKKP-UHFFFAOYSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.729210145598593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(2-hydroxyphenyl)-9-methoxy-2H,8H-[1,3]dioxolo[4,5-g]chromen-8-one

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.499565235

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.664087504966249

> <JCHEM_PKA_STRONGEST_BASIC>
-4.501913481120293

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
79.9512

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
betavulgarin

> <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  O   UNK     0       1.308   1.154   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.078   0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.078  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.308  -1.924   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.308  -3.464   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.694  -4.234   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.462  -5.774   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.078  -5.774   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.078  -4.234   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.308  -3.464   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.308  -1.924   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.694  -1.154   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.694   0.384   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.308   1.154   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.462   2.694   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.078   3.464   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.078   5.004   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.308   5.774   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.694   5.004   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.694   3.464   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.080   2.694   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.694  -1.154   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.080  -0.384   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    5    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    3   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    2   13   15                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   15   19   21                                                  
CONECT   21   20                                                            
CONECT   22    4   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
2'-Hydroxy-5-methoxy-6,7-methylenedioxyisoflavone	ChEBI

Chemical Formula

C₁₇H₁₂O₆

Average Mass

312.2736 Da

Monoisotopic Mass

312.06339 Da

IUPAC Name

7-(2-hydroxyphenyl)-9-methoxy-2H,8H-[1,3]dioxolo[4,5-g]chromen-8-one

Traditional Name

betavulgarin

CAS Registry Number

51068-94-1

SMILES

COC1=C2OCOC2=CC2=C1C(=O)C(=CO2)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C17H12O6/c1-20-17-14-12(6-13-16(17)23-8-22-13)21-7-10(15(14)19)9-4-2-3-5-11(9)18/h2-7,18H,8H2,1H3

InChI Key

NDVRQFZUJRMKKP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Baptisia spp.	Plant	KNApSAcK
Beta corolliflora	Plant	KNApSAcK
Beta lomatogona	Plant	KNApSAcK
Beta procumbens	Plant	KNApSAcK
Beta trigyna	Plant	KNApSAcK
Beta vulgaris	FooDB	KNAPSACK
Cercospora beticola	-	KNApSAcK
Cicer arietinum	FooDB	KNAPSACK
Cotoneaster pannosa	Plant	KNApSAcK
Dalbergia spp.	Plant	KNApSAcK
Dianthus spp.	Plant	KNApSAcK
Iris tenuifolia	Plant	KNApSAcK
Iris tingitana	LOTUS Database	35616633
Trifolium spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Benzodioxole
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:3081 )
methoxyisoflavone (CHEBI:3081 )
isoflavones (C10201 )
Isoflavonoids (C10201 )
Isoflavonoids (LMPK12050361 )

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	2.67	ALOGPS
logP	2.5	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.95 m³·mol⁻¹	ChemAxon
Polarizability	30.73 Å³	ChemAxon
Number of Rings	4	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011161

KNApSAcK ID

C00002509

Chemspider ID

Not Available

KEGG Compound ID

C10201

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442668

PDB ID

Not Available

ChEBI ID

3081

Good Scents ID

Not Available

References

General References

Choudhary MI, Hareem S, Siddiqui H, Anjum S, Ali S, Atta-Ur-Rahman, Zaidi MI: A benzil and isoflavone from Iris tenuifolia. Phytochemistry. 2008 Jun;69(9):1880-5. doi: 10.1016/j.phytochem.2008.03.011. Epub 2008 May 9. [PubMed:18472117 ]
Elliger CA, Halloin JM: Phenolics induced in Beta vulgaris by Rhizoctonia solani infection. Phytochemistry. 1994 Oct;37(3):691-3. doi: 10.1016/s0031-9422(00)90340-6. [PubMed:7765684 ]

Showing NP-Card for Betavulgarin (NP0047564)

MOL for NP0047564 (Betavulgarin)

3D MOL for NP0047564 (Betavulgarin)

3D SDF for NP0047564 (Betavulgarin)

3D-SDF for NP0047564 (Betavulgarin)

PDB for NP0047564 (Betavulgarin)

3D PDB for NP0047564 (Betavulgarin)

SMILES for NP0047564 (Betavulgarin)

INCHI for NP0047564 (Betavulgarin)

Structure for NP0047564 (Betavulgarin)

3D Structure for NP0047564 (Betavulgarin)