NP-MRD: Showing NP-Card for Lanceolatin B (flavonoid) (NP0062437)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 07:05:54 UTC

Updated at

2022-04-28 07:05:54 UTC

NP-MRD ID

NP0062437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lanceolatin B (flavonoid)

Description

LANCEOLATIN B belongs to the class of organic compounds known as furanoflavones. These are polycyclic aromatic compounds containing a furan ring fused to a flavan-3-one. Lanceolatin B (flavonoid) is found in Dahlstedtia pinnata, Lonchocarpus heptaphyllus, Millettia erythrocalyx, Millettia leucantha, Millettia peguensis, Millettia pulchra, Millettia pinnata and Tephrosia purpurea . Lanceolatin B (flavonoid) was first documented in 2015 (PMID: 26426474). Based on a literature review a small amount of articles have been published on LANCEOLATIN B (PMID: 34203624) (PMID: 31656737) (PMID: 30448188) (PMID: 28845653).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 33  0  0  0  0  0  0  0  0999 V2000
    1.4659   -3.4847   -0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744   -2.3020   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2813   -2.0206   -0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7638   -0.7343   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1734   -0.3904   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1488   -1.3323   -0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5105   -0.9966   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8523    0.3325   -0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8874    1.3165   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503    0.9349   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.2246    0.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4390    0.0548    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504   -1.2473   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3177   -1.4182   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2035   -0.3652    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041    0.9192    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117    2.1003    0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4087    3.0518    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1516    2.4658    0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    1.1019    0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001   -2.8351   -0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8932   -2.3764   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2617   -1.7797   -0.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9183    0.5952   -0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1723    2.3693    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8018    1.7195    0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6830   -2.4508   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734   -0.5068    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5510    4.1053    0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1779    2.9488    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 11  1  0
 11 12  1  0
 12 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 13  2  1  0
 10  5  1  0
 13 12  1  0
 16 20  1  0
  3 21  1  0
 19 30  1  0
 18 29  1  0
 15 28  1  0
 14 27  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
M  END


  Mrv1652304282209052D          

 20 23  0  0  0  0            999 V2000
   -1.0169   -1.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -1.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   -0.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5015   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8468   -2.2790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5461    1.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807    2.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8053    1.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1953    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607    0.5517    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  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
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C=C(OC2=C3C=COC3=CC=C12)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H10O3/c18-14-10-16(11-4-2-1-3-5-11)20-17-12(14)6-7-15-13(17)8-9-19-15/h1-10H

> <INCHI_KEY>
NQNOTBRHBRJKKH-UHFFFAOYSA-N

> <FORMULA>
C17H10O3

> <MOLECULAR_WEIGHT>
262.264

> <EXACT_MASS>
262.062994182

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
27.366159305371248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenyl-4H-furo[2,3-h]chromen-4-one

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
3.126508499333333

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.409316448950271

> <JCHEM_PKA_STRONGEST_BASIC>
-2.884706996001189

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
75.81230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-phenylfuro[2,3-h]chromen-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.898  -2.753   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.170  -4.110   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.369  -4.158   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.180  -2.849   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.452  -1.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.087  -1.444   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.081  -0.268   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.507  -0.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.394  -2.386   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.263  -0.183   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.803  -0.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.531  -1.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.719  -2.897   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.447  -4.254   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.614   1.078   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.886   2.435   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.697   3.744   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.237   3.696   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.965   2.339   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.153   1.030   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    1                                                       
CONECT   10    5   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    4   14                                                  
CONECT   14   13                                                            
CONECT   15   11   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-Phenyl-4H-furo(2,3-H)chromen-4-one	MeSH

Chemical Formula

C₁₇H₁₀O₃

Average Mass

262.2640 Da

Monoisotopic Mass

262.06299 Da

IUPAC Name

2-phenyl-4H-furo[2,3-h]chromen-4-one

Traditional Name

2-phenylfuro[2,3-h]chromen-4-one

CAS Registry Number

Not Available

SMILES

O=C1C=C(OC2=C3C=COC3=CC=C12)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H10O3/c18-14-10-16(11-4-2-1-3-5-11)20-17-12(14)6-7-15-13(17)8-9-19-15/h1-10H

InChI Key

NQNOTBRHBRJKKH-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
Dahlstedtia pinnata	LOTUS Database	35616633
Lonchocarpus latifolius	LOTUS Database	35616633
Millettia erythrocalyx	LOTUS Database	35616633
Millettia leucantha	LOTUS Database	35616633
Millettia peguensis	LOTUS Database	35616633
Millettia pulchra	LOTUS Database	35616633
Pongamia pinnata	Plant	KNApSAcK
Tephrosia purpurea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoflavones. These are polycyclic aromatic compounds containing a furan ring fused to a flavan-3-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Furanoflavones

Alternative Parents

Substituents

Furanoflavone
Furanoflavonoid or dihydroflavonoid
Chromone
Benzopyran
1-benzopyran
Benzofuran
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.91	ALOGPS
logP	3.13	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.81 m³·mol⁻¹	ChemAxon
Polarizability	27.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00019016

Chemspider ID

9153466

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10978265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vo TH, Liaw CC, Lin YC, Nguyen DH, Nguyen TTN, Lee CK, Kuo YH: Quantification and Optimization of Ethanolic Extract Containing the Bioactive Flavonoids from Millettia pulchra Radix. Molecules. 2021 Jun 15;26(12):3641. doi: 10.3390/molecules26123641. [PubMed:34203624 ]
Kumar G, Gupta R, Sharan S, Roy P, Pandey DM: Anticancer activity of plant leaves extract collected from a tribal region of India. 3 Biotech. 2019 Nov;9(11):399. doi: 10.1007/s13205-019-1927-x. Epub 2019 Oct 12. [PubMed:31656737 ]
Sharma R, Williams IS, Gatchie L, Sonawane VR, Chaudhuri B, Bharate SB: Furanoflavones pongapin and lanceolatin B blocks the cell cycle and induce senescence in CYP1A1-overexpressing breast cancer cells. Bioorg Med Chem. 2018 Dec 15;26(23-24):6076-6086. doi: 10.1016/j.bmc.2018.11.013. Epub 2018 Nov 10. [PubMed:30448188 ]
Wang HR, Li XB, Yang QN, Tang MH, Xiao CB, Wan L: [Metabolic stability and metabolic enzyme phaenotypes of lanceolatin B in liver microsomes of different species by UPLC-MS/MS]. Zhongguo Zhong Yao Za Zhi. 2016 Jan;41(1):124-128. doi: 10.4268/cjcmm20160124. [PubMed:28845653 ]
Sharma R, Vishwakarma RA, Bharate SB: An efficient transformation of furano-hydroxychalcones to furanoflavones via base mediated intramolecular tandem O-arylation and C-O bond cleavage: a new approach for the synthesis of furanoflavones. Org Biomol Chem. 2015 Nov 14;13(42):10461-5. doi: 10.1039/c5ob01802a. Epub 2015 Oct 1. [PubMed:26426474 ]

Showing NP-Card for Lanceolatin B (flavonoid) (NP0062437)

MOL for NP0062437 (Lanceolatin B (flavonoid))

3D MOL for NP0062437 (Lanceolatin B (flavonoid))

3D SDF for NP0062437 (Lanceolatin B (flavonoid))

3D-SDF for NP0062437 (Lanceolatin B (flavonoid))

PDB for NP0062437 (Lanceolatin B (flavonoid))

3D PDB for NP0062437 (Lanceolatin B (flavonoid))

SMILES for NP0062437 (Lanceolatin B (flavonoid))

INCHI for NP0062437 (Lanceolatin B (flavonoid))

Structure for NP0062437 (Lanceolatin B (flavonoid))

3D Structure for NP0062437 (Lanceolatin B (flavonoid))