NP-MRD: Showing NP-Card for Isobergapten (NP0046907)

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Record Information

Version

2.0

Created at

2022-03-17 20:31:30 UTC

Updated at

2022-03-17 20:31:30 UTC

NP-MRD ID

NP0046907

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isobergapten

Description

Isobergapten is found in Alocasia macrorrhizos, Angelica pubescens f.biserrata , Deverra triradiata, Dorstenia asaroides, Dorstenia bahiensis, Dorstenia barnimiana, Dorstenia brasiliensis , Dorstenia bryonifolia, Dorstenia cayapia, Dorstenia cayapiaa, Dorstenia contrajerva , Dorstenia drakena , Dorstenia excentria, Dorstenia heringerii, Dorstenia lindeniana, Dorstenia psilurus, Heracleum asperum, Heracleum canescens, Heracleum dissectum, Heracleum granatense, Heracleum grandiflorum, Heracleum lehmannianum, Heracleum leskovii, Heracleum moellendorffii Hance, Heracleum moellendorffii Hance var.paucivitatum, Heracleum nepalense , Heracleum pastinacifolium, Heracleum persicum, Heracleum pinnatum, Heracleum ponticum, Heracleum rapula, Heracleum sphondylium , Heracleum wallichii, Heracleum woroschiklowii, Heracleum yungningense, Pimpinella magna, Pimpinella saxifraga , Ruta pinnata, Saposhnikovia divaricata, Stellera chamaejasme and Tordylium apulum .

Structure

MOL SDF PDB SMILES InChI

Isobergapten
  Mrv1572001071617272D          

 16 18  0  0  0  0            999 V2000
    1.6283    3.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.5420    0.0000 O   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
    2.4083    1.7892    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
    3.5995    0.8656    0.0000 O   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
    2.8963   -0.2691    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
    1.5391    0.3867    0.0000 C   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
    0.2799   -0.2887    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
   -0.1101    0.4383    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
    1.1491    1.1137    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  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  2  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
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 10 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046907

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=CO2)C2=C1C=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C12H8O4/c1-14-9-6-10-8(4-5-15-10)12-7(9)2-3-11(13)16-12/h2-6H,1H3

> <INCHI_KEY>
AJSPSRWWZBBIOR-UHFFFAOYSA-N

> <FORMULA>
C12H8O4

> <MOLECULAR_WEIGHT>
216.192

> <EXACT_MASS>
216.042258738

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.90285302320591

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-2H-furo[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
1.7848117503333332

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8270283772676734

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
56.85290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxyfuro[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Isobergapten                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       3.039   6.054   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.228   4.745   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.719   1.616   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.062  -0.587   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    3   10                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₈O₄

Average Mass

216.1920 Da

Monoisotopic Mass

216.04226 Da

IUPAC Name

5-methoxy-2H-furo[2,3-h]chromen-2-one

Traditional Name

5-methoxyfuro[2,3-h]chromen-2-one

CAS Registry Number

482-48-4

SMILES

COC1=CC2=C(C=CO2)C2=C1C=CC(=O)O2

InChI Identifier

InChI=1S/C12H8O4/c1-14-9-6-10-8(4-5-15-10)12-7(9)2-3-11(13)16-12/h2-6H,1H3

InChI Key

AJSPSRWWZBBIOR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alocasia macrorrhiza	LOTUS Database	35616633
Angelica pubescens f.biserrata	Plant	KNApSAcK
Deverra triradiata	LOTUS Database	35616633
Dorstenia asaroides	Plant	KNApSAcK
Dorstenia bahiensis	Plant	KNApSAcK
Dorstenia barnimiana	Plant	KNApSAcK
Dorstenia brasiliensis	Plant	KNApSAcK
Dorstenia bryonifolia	Plant	KNApSAcK
Dorstenia cayapia	LOTUS Database	35616633
Dorstenia cayapiaa	Plant	KNApSAcK
Dorstenia contrajerva	Plant	KNApSAcK
Dorstenia drakena	Plant	KNApSAcK
Dorstenia excentria	Plant	KNApSAcK
Dorstenia heringerii	Plant	KNApSAcK
Dorstenia lindeniana	Plant	KNApSAcK
Dorstenia psilurus	Plant	KNApSAcK
Heracleum asperum	Plant	KNApSAcK
Heracleum canescens	Plant	KNApSAcK
Heracleum dissectum	Plant	KNApSAcK
Heracleum granatense	Plant	KNApSAcK
Heracleum grandiflorum	Plant	KNApSAcK
Heracleum lehmannianum	Plant	KNApSAcK
Heracleum leskovii	LOTUS Database	35616633
Heracleum moellendorffii Hance	Plant	KNApSAcK
Heracleum moellendorffii Hance var.paucivitatum	Plant	KNApSAcK
Heracleum nepalense	Plant	KNApSAcK
Heracleum pastinacifolium	LOTUS Database	35616633
Heracleum persicum	LOTUS Database	35616633
Heracleum pinnatum	Plant	KNApSAcK
Heracleum ponticum	Plant	KNApSAcK
Heracleum rapula	LOTUS Database	35616633
Heracleum sphondylium	Plant	KNApSAcK
Heracleum wallichii	Plant	KNApSAcK
Heracleum woroschiklowii	Plant	KNApSAcK
Heracleum yungningense	Plant	KNApSAcK
Pastinaca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pimpinella magna	Plant	KNApSAcK
Pimpinella saxifraga	Plant	KNApSAcK
Ruta pinnata	Plant	KNApSAcK
Saposhnikovia divaricata	LOTUS Database	35616633
Stellera chamaejasme	Plant	KNApSAcK
Tordylium apulum	Plant	KNApSAcK

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
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Furan
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

furanocoumarin (CHEBI:81487 )

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	2.06	ALOGPS
logP	1.78	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.85 m³·mol⁻¹	ChemAxon
Polarizability	20.9 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

FDB006431

KNApSAcK ID

C00037321

Chemspider ID

Not Available

KEGG Compound ID

C18082

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68082

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isobergapten (NP0046907)

MOL for NP0046907 (Isobergapten)

3D MOL for NP0046907 (Isobergapten)

3D SDF for NP0046907 (Isobergapten)

3D-SDF for NP0046907 (Isobergapten)

PDB for NP0046907 (Isobergapten)

3D PDB for NP0046907 (Isobergapten)

SMILES for NP0046907 (Isobergapten)

INCHI for NP0046907 (Isobergapten)

Structure for NP0046907 (Isobergapten)

3D Structure for NP0046907 (Isobergapten)