NP-MRD: Showing NP-Card for Luvangetin (NP0051452)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:48 UTC

Updated at

2022-04-27 22:48:48 UTC

NP-MRD ID

NP0051452

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luvangetin

Description

Luvangetin belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Luvangetin is found in Aegle marmelos , Atalantia racemosa, Boenninghausenia albiflora , Brosimum gaudichaudii, Brosimum parinarioides, Brosimum rubescens , Chloroxylon swietenia , Citrus paradisi, Citrus trifoliata, Hesperethusa crenulata, Limonia acidissima, Luvunga scandens , Pamburus missionis, Phebalium clavatum, Phebalium tuberculosum, Toddalia asiatica, Zanthoxylum ailanthoides and Zanthoxylum avicennae. Luvangetin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    1.1642   -2.8494   -0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9421   -1.6239   -1.6035 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9438   -0.4397   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844   -0.0256   -0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708    1.1500    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    1.8707    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0909    1.4549    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670    2.1571    0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4094    1.6475   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3856    0.4728   -1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4610    0.0007   -1.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2465   -0.1451   -1.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1148    0.2822   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5451    1.5963    0.9069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6480    0.8974    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555   -0.3653   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6647   -0.2063   -1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139   -1.5237    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4263   -0.7690   -0.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1932   -2.8217   -0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4376   -2.9969   -0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1348   -3.6488   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8932    2.7983    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310    3.0746    0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3462    2.1957   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5612    2.5328    1.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018    1.2639    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829   -0.9398   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    0.8004   -1.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1650   -0.4211   -2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7600   -1.1340    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2415   -2.0047    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5994   -2.2801    0.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 13  2  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4 19  1  0
 19 16  1  0
 16 17  1  0
 16 18  1  0
 16 15  1  0
 15 14  2  0
  4  3  1  0
  7 13  1  0
 14  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  9 25  1  0
  8 24  1  0
  6 23  1  0
 17 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
 15 27  1  0
 14 26  1  0
M  END


  Mrv1533004251505342D          

 19 21  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    2.8579    0.8250    0.0000 C   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
    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 O   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
    3.5724   -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
    2.1434   -0.4125    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  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  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
 12 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(=O)C=CC2=CC2=C1OC(C)(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-15(2)7-6-10-8-9-4-5-11(16)18-12(9)14(17-3)13(10)19-15/h4-8H,1-3H3

> <INCHI_KEY>
XYPWCJWXFYYGPA-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.273

> <EXACT_MASS>
258.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.779197976050398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.5263117516666664

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.675759667437073

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
72.40520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luvangetin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18    3   12                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
10-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one	Kegg

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2730 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

10-methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one

Traditional Name

luvangetin

CAS Registry Number

Not Available

SMILES

COC1=C2OC(=O)C=CC2=CC2=C1OC(C)(C)C=C2

InChI Identifier

InChI=1S/C15H14O4/c1-15(2)7-6-10-8-9-4-5-11(16)18-12(9)14(17-3)13(10)19-15/h4-8H,1-3H3

InChI Key

XYPWCJWXFYYGPA-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
Aegle marmelos	Plant	KNApSAcK
Atalantia racemosa	LOTUS Database	35616633
Boenninghausenia albiflora	Plant	KNApSAcK
Brosimum gaudichaudii	LOTUS Database	35616633
Brosimum parinarioides	LOTUS Database	35616633
Brosimum rubescens	Plant	KNApSAcK
Chloroxylon swietenia	Plant	KNApSAcK
Citrus paradisi	LOTUS Database	35616633
Citrus trifoliata	LOTUS Database	35616633
Hesperethusa crenulata	Plant	KNApSAcK
Limonia acidissima	LOTUS Database	35616633
Luvunga scandens	Plant	KNApSAcK
Pamburus missionis	LOTUS Database	35616633
Phebalium clavatum	Plant	KNApSAcK
Phebalium tuberculosum	LOTUS Database	35616633
Toddalia asiatica	LOTUS Database	35616633
Zanthoxylum ailanthoides	LOTUS Database	35616633
Zanthoxylum avicennae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:6586 )
coumarins (C09273 )

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	3.04	ALOGPS
logP	2.53	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.41 m³·mol⁻¹	ChemAxon
Polarizability	26.78 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

C00002481

Chemspider ID

Not Available

KEGG Compound ID

C09273

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

343582

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Luvangetin (NP0051452)

MOL for NP0051452 (Luvangetin)

3D MOL for NP0051452 (Luvangetin)

3D SDF for NP0051452 (Luvangetin)

3D-SDF for NP0051452 (Luvangetin)

PDB for NP0051452 (Luvangetin)

3D PDB for NP0051452 (Luvangetin)

SMILES for NP0051452 (Luvangetin)

INCHI for NP0051452 (Luvangetin)

Structure for NP0051452 (Luvangetin)

3D Structure for NP0051452 (Luvangetin)