NP-MRD: Showing NP-Card for bolusanthin (NP0279966)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 05:32:45 UTC

Updated at

2022-09-09 05:32:45 UTC

NP-MRD ID

NP0279966

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bolusanthin

Description

Bolusanthin belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, bolusanthin is considered to be a flavonoid lipid molecule. bolusanthin is found in Bolusanthus speciosus. Bolusanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -6.0108    0.1173    0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8303    0.8503    0.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6010    0.3155    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4581   -1.0265    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -1.5614   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -0.7635   -0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -1.3132   -0.5548 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2205   -2.7070   -0.3644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475   -1.0537   -1.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883   -0.7287   -2.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255   -0.0641   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524    0.5911   -1.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6664    1.2467   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8127    1.9282   -1.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3674    1.2560    0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2502    0.6039    0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9297    0.5968    2.1893 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355   -0.0518   -0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -0.7598    0.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446   -0.9000    1.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451    0.5787    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4720    1.1036    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6239    2.4511    0.7443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7643   -0.8732    1.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7604    0.5741    1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4284   -0.1112   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080   -1.6824    0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0947   -2.6075   -0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629   -3.1949   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210   -1.8708   -2.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0629   -0.1582   -2.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054    0.5958   -2.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7274    1.5146   -1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9977    1.7659    1.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191    1.0732    2.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.2039    0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8326    3.0612    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  2  0
 22 23  1  0
 22 21  1  0
 21  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  1  6
  7  9  1  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  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  4  3  1  0
 19  7  1  0
 18 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 37  1  0
 21 36  1  0
  5 28  1  0
  4 27  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
M  END


  Mrv1533004241520102D          

 23 25  0  0  0  0            999 V2000
    0.1161   -4.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -4.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320   -3.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623   -2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804   -3.4200    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 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
    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
    2.8579   -2.4750    0.0000 O   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
   -0.0980   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -3.0745    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
 16 20  1  0  0  0  0
 14 21  1  0  0  0  0
  9 22  1  0  0  0  0
  4 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0279966

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O7/c1-22-12-3-2-8(4-10(12)18)16(21)7-23-13-6-9(17)5-11(19)14(13)15(16)20/h2-6,17-19,21H,7H2,1H3

> <INCHI_KEY>
XCIMIGGTZKYBOR-UHFFFAOYSA-N

> <FORMULA>
C16H14O7

> <MOLECULAR_WEIGHT>
318.281

> <EXACT_MASS>
318.073952791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.705388581169103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
1.9784691853333332

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.219480280768563

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.736837049213385

> <JCHEM_PKA_STRONGEST_BASIC>
-4.353268793533698

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
79.3857

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bolusanthin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.217  -9.278   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.773  -8.099   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.246  -6.651   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.236  -5.472   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.710  -4.025   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.797  -4.937   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.270  -6.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.183  -2.043   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.753  -5.739   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   18   22                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17    9   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
CONECT   21   14                                                            
CONECT   22    9                                                            
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₇

Average Mass

318.2810 Da

Monoisotopic Mass

318.07395 Da

IUPAC Name

3,5,7-trihydroxy-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

bolusanthin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H14O7/c1-22-12-3-2-8(4-10(12)18)16(21)7-23-13-6-9(17)5-11(19)14(13)15(16)20/h2-6,17-19,21H,7H2,1H3

InChI Key

XCIMIGGTZKYBOR-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Bolusanthus speciosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

3'-hydroxy,4'-methoxyisoflavonoid
Isoflavanol
Isoflavanone
Hydroxyisoflavonoid
Isoflavan
Chromone
Methoxyphenol
Benzopyran
1-benzopyran
Chromane
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acyloin
Tertiary alcohol
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050510 )

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	1.16	ALOGPS
logP	1.98	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.39 m³·mol⁻¹	ChemAxon
Polarizability	30.71 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for bolusanthin (NP0279966)

MOL for NP0279966 (bolusanthin)

3D MOL for NP0279966 (bolusanthin)

3D SDF for NP0279966 (bolusanthin)

3D-SDF for NP0279966 (bolusanthin)

PDB for NP0279966 (bolusanthin)

3D PDB for NP0279966 (bolusanthin)

SMILES for NP0279966 (bolusanthin)

INCHI for NP0279966 (bolusanthin)

Structure for NP0279966 (bolusanthin)

3D Structure for NP0279966 (bolusanthin)