NP-MRD: Showing NP-Card for Bowdichione (NP0051465)

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Record Information

Version

2.0

Created at

2022-04-27 22:49:21 UTC

Updated at

2022-04-27 22:49:21 UTC

NP-MRD ID

NP0051465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bowdichione

Description

Bowdichione belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. Thus, bowdichione is considered to be a flavonoid lipid molecule. Bowdichione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. A hydroxyisoflavone with a quinone structure in ring B. Bowdichione is found in Bowdichia nitida, Dalbergia odorifera and Dalbergia parviflora . Bowdichione was first documented in 1998 (PMID: 9525107). Isolated from Dalbergia parviflora, it exhibits antineoplastic and anti-inflammatory activities (PMID: 19928832).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    6.0096   -0.8301    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215   -0.2926   -0.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386   -0.2410   -0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975    0.2695   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    0.3463   -1.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6466    0.8543   -2.5649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356   -0.1716   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -0.0594   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9101    0.2171   -1.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2188    0.3643   -1.9025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0322    0.2688   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096    0.4337   -1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2560    0.3285    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6278    0.4944   -0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7694    0.0538    1.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3990   -0.1089    1.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5505   -0.0045    0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589   -0.1688    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7903   -0.4109    1.6503 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6791   -0.6767    0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -0.7495    0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -1.2514    1.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7758   -1.8780    1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7155   -0.1780    2.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1093   -0.7354    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1400    0.6584   -2.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3254    0.3180   -2.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801    0.6485   -2.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0568    0.6965   -0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4337   -0.0288    2.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9730   -0.3277    2.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0753   -1.0984    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7 20  2  0
 20 21  1  0
 21 22  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 21  3  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
 20 32  1  0
  9 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
M  END


  Mrv1533004161504532D          

 22 24  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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   -1.6500    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   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
    2.8579    0.0000    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
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C(=CC1=O)C1=COC2=CC(O)=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c1-21-15-6-12(18)10(5-13(15)19)11-7-22-14-4-8(17)2-3-9(14)16(11)20/h2-7,17H,1H3

> <INCHI_KEY>
GCAIEHBYLQNGAF-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.25

> <EXACT_MASS>
298.047738042

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.835834534161165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(7-hydroxy-4-oxo-4H-chromen-3-yl)-5-methoxycyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
1.4224365030000001

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.06897982164579

> <JCHEM_PKA_STRONGEST_BASIC>
-4.794493339270195

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
78.72639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bowdichione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   11   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₀O₆

Average Mass

298.2500 Da

Monoisotopic Mass

298.04774 Da

IUPAC Name

2-(7-hydroxy-4-oxo-4H-chromen-3-yl)-5-methoxycyclohexa-2,5-diene-1,4-dione

Traditional Name

bowdichione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C(=CC1=O)C1=COC2=CC(O)=CC=C2C1=O

InChI Identifier

InChI=1S/C16H10O6/c1-21-15-6-12(18)10(5-13(15)19)11-7-22-14-4-8(17)2-3-9(14)16(11)20/h2-7,17H,1H3

InChI Key

GCAIEHBYLQNGAF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bowdichia nitida	Plant	KNApSAcK
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia parviflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
P-benzoquinone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Ketone
Cyclic ketone
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinone (CHEBI:3162 )
hydroxyisoflavone (CHEBI:3162 )
methoxyisoflavone (CHEBI:3162 )
oxoisoflavone (CHEBI:3162 )
isoflavones (C10202 )
isoflavans (C10202 )
Isoflavans (LMPK12080050 )

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	2.6	ALOGPS
logP	1.42	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.07	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.73 m³·mol⁻¹	ChemAxon
Polarizability	28.84 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002511

Chemspider ID

Not Available

KEGG Compound ID

C10202

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281705

PDB ID

Not Available

ChEBI ID

3162

Good Scents ID

Not Available

References

General References

Chan SC, Chang YS, Wang JP, Chen SC, Kuo SC: Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera. Planta Med. 1998 Mar;64(2):153-8. doi: 10.1055/s-2006-957394. [PubMed:9525107 ]
Umehara K, Nemoto K, Matsushita A, Terada E, Monthakantirat O, De-Eknamkul W, Miyase T, Warashina T, Degawa M, Noguchi H: Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. J Nat Prod. 2009 Dec;72(12):2163-8. doi: 10.1021/np900676y. [PubMed:19928832 ]

Showing NP-Card for Bowdichione (NP0051465)

MOL for NP0051465 (Bowdichione)

3D MOL for NP0051465 (Bowdichione)

3D SDF for NP0051465 (Bowdichione)

3D-SDF for NP0051465 (Bowdichione)

PDB for NP0051465 (Bowdichione)

3D PDB for NP0051465 (Bowdichione)

SMILES for NP0051465 (Bowdichione)

INCHI for NP0051465 (Bowdichione)

Structure for NP0051465 (Bowdichione)

3D Structure for NP0051465 (Bowdichione)