NP-MRD: Showing NP-Card for (8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one (NP0318801)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 19:30:37 UTC

Updated at

2022-09-11 19:30:37 UTC

NP-MRD ID

NP0318801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one

Description

CHEMBL3950578 belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. (8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one is found in Oldenlandia corymbosa. Based on a literature review very few articles have been published on CHEMBL3950578.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    4.1203   -0.4834    1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5265    0.0346   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3489    0.8285   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1105   -0.1409   -0.2772 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3564   -0.9483    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465   -0.5452    0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313    0.6852   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1602    1.3065   -0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0565    2.5452   -1.1930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2368    3.2005   -1.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940    0.7315   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444   -0.5085    0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6660   -1.1296    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6438   -2.3546    1.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451   -2.9231    1.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4380   -4.0699    2.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112   -2.3086    1.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2684   -1.1444    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    1.0720   -0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.3592    1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5608   -1.0732    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8409    0.9995   -1.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6074    1.8292   -0.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564    0.2219   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6040   -1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481   -0.6423    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169   -2.0323    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889    2.5112   -2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8491    3.4634   -0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099    4.1153   -2.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044    1.2243   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5641   -0.6267    0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5724   -2.8747    1.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7 19  1  0
 19  4  1  0
  4  5  1  0
  5  6  1  0
  6 18  2  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 11  8  1  0
  6  7  1  0
 12 18  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
  4 25  1  6
  5 26  1  0
  5 27  1  0
 14 33  1  0
 13 32  1  0
 11 31  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652309112221302D          

 19 21  0  0  1  0            999 V2000
    5.0883    0.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355    2.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4529   -2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 O   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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  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
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  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 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  2  0  0  0  0
 12 18  1  0  0  0  0
  7 19  1  0  0  0  0
  4 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2O[C@H](CC2=C2OC(=O)C=CC2=C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-8(2)11-7-10-14-9(4-5-13(16)19-14)6-12(17-3)15(10)18-11/h4-6,11H,1,7H2,2-3H3/t11-/m1/s1

> <INCHI_KEY>
ZNTWWRJQOSQMFP-LLVKDONJSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.273

> <EXACT_MASS>
258.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.84903540367795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8R)-6-methoxy-8-(prop-1-en-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one

> <JCHEM_LOGP>
2.542283755333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.618906131342423

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
70.89950000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(8R)-6-methoxy-8-(prop-1-en-2-yl)-8H,9H-furo[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       9.498   1.543   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.141   2.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.093   3.811   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.307  -3.109   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.579  -4.466   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.062   2.127   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.719  -0.076   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    6   12                                                  
CONECT   19    7    4                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2730 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

(8R)-6-methoxy-8-(prop-1-en-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one

Traditional Name

(8R)-6-methoxy-8-(prop-1-en-2-yl)-8H,9H-furo[2,3-h]chromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=C2O[C@H](CC2=C2OC(=O)C=CC2=C1)C(C)=C

InChI Identifier

InChI=1S/C15H14O4/c1-8(2)11-7-10-14-9(4-5-13(16)19-14)6-12(17-3)15(10)18-11/h4-6,11H,1,7H2,2-3H3/t11-/m1/s1

InChI Key

ZNTWWRJQOSQMFP-LLVKDONJSA-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
Oldenlandia corymbosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Angular furanocoumarins

Alternative Parents

Substituents

Angular furanocoumarin
Benzopyran
1-benzopyran
Coumaran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	2.54	ChemAxon
pKa (Strongest Basic)	-4.6	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	2	ChemAxon
Refractivity	70.9 m³·mol⁻¹	ChemAxon
Polarizability	26.85 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

28283264

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60150692

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one (NP0318801)

MOL for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D MOL for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D SDF for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D-SDF for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

PDB for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D PDB for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

SMILES for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

INCHI for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

Structure for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D Structure for NP0318801 ((8r)-6-methoxy-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)