NP-MRD: Showing NP-Card for 8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one (NP0270608)

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Record Information

Version

2.0

Created at

2022-09-08 16:36:56 UTC

Updated at

2022-09-08 16:36:56 UTC

NP-MRD ID

NP0270608

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Oroselone, also known as kvannin, 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. Oroselone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Oroselone has been detected, but not quantified in, a few different foods, such as fats and oils, green vegetables, and herbs and spices. 8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one is found in Angelica archangelica and Angelica cincta. This could make oroselone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307272D          

 17 19  0  0  0  0            999 V2000
    5.0883   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355   -1.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1=CC2=C(O1)C=CC1=C2OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O3/c1-8(2)12-7-10-11(16-12)5-3-9-4-6-13(15)17-14(9)10/h3-7H,1H2,2H3

> <INCHI_KEY>
FQCPXIJRWHRHIP-UHFFFAOYSA-N

> <FORMULA>
C14H10O3

> <MOLECULAR_WEIGHT>
226.2274

> <EXACT_MASS>
226.062994186

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.772836981193947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.8985808126666663

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.174168268297907

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
64.2355

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.498  -0.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.093  -2.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.141  -0.731   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.719   1.616   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.062  -0.587   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    5    9                                                       
CONECT    4    6    9                                                       
CONECT    5    3   11                                                       
CONECT    6    4   13                                                       
CONECT    7   10   12                                                       
CONECT    8    1    2   12                                                  
CONECT    9    3    4   14                                                  
CONECT   10    7   11   14                                                  
CONECT   11    5   10   16                                                  
CONECT   12    7    8   16                                                  
CONECT   13    6   15   17                                                  
CONECT   14    9   10   17                                                  
CONECT   15   13                                                            
CONECT   16   11   12                                                       
CONECT   17   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
8-(1-Methylethenyl)-2H-furo(2,3-H)-1-benzopyran-2-one	HMDB
8-(1-Methylethenyl)-2H-furo[2,3-H]-1-benzopyran-2-one	HMDB
8-(1-Methylethenyl)-2H-furo[2,3-H]-1-benzopyran-2-one, 9ci	HMDB
8-Isopropenyl-2H-furo[2,3-H]-1-benzopyran-2-one	HMDB
Kvannin	HMDB

Chemical Formula

C₁₄H₁₀O₃

Average Mass

226.2274 Da

Monoisotopic Mass

226.06299 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=C)C1=CC2=C(O1)C=CC1=C2OC(=O)C=C1

InChI Identifier

InChI=1S/C14H10O3/c1-8(2)12-7-10-11(16-12)5-3-9-4-6-13(15)17-14(9)10/h3-7H,1H2,2H3

InChI Key

FQCPXIJRWHRHIP-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
Angelica archangelica	LOTUS Database	35616633
Angelica cincta	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
Benzofuran
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen 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	3.03	ALOGPS
logP	2.9	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.24 m³·mol⁻¹	ChemAxon
Polarizability	23.77 Å³	ChemAxon
Number of Rings	3	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

HMDB0033925

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012125

KNApSAcK ID

Not Available

Chemspider ID

67063

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one (NP0270608)

MOL for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

3D MOL for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

3D SDF for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

3D-SDF for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

PDB for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

3D PDB for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

SMILES for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

INCHI for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

Structure for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)

3D Structure for NP0270608 (8-(prop-1-en-2-yl)furo[2,3-h]chromen-2-one)