NP-MRD: Showing NP-Card for isopsoralen (NP0331806)

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Record Information

Version

2.0

Created at

2023-09-08 08:26:34 UTC

Updated at

2024-09-03 04:17:01 UTC

NP-MRD ID

NP0331806

Natural Product DOI

https://doi.org/10.57994/0893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isopsoralen

Description

Angelicin, also known as isopsoralen or bakuchicin, 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. Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. Furocoumarins can cause photosensitization dermatitis especially if these compounds come into contact with the skin. If inhaled, remove to fresh air. Angelicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Angelicin is found, on average, in the highest concentration within parsnips. Angelicin has also been detected, but not quantified in, several different foods, such as fats and oils, figs, wild celeries, corianders, and herbs and spices. This could make angelicin a potential biomarker for the consumption of these foods. Angelicin is a potentially toxic compound. All photobiological effects of furocoumarins result from their photochemical reactions. The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts.

Structure

MOL SDF PDB SMILES InChI

Angelicin
  Mrv1572001071617262D          

 20 22  0  0  0  0            999 V2000
    2.1315   -1.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6133    0.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    1.8848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9121   -0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6265   -0.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9121   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6265   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315   -0.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0918   -0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542    1.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7840   -1.7280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6265   -2.3963    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9726    0.0903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5318   -0.4901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385   -1.0598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5423    0.8842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
  2  5  1  0  0  0  0
  2 14  1  0  0  0  0
  3 14  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  2  0  0  0  0
  8 15  1  0  0  0  0
  9 16  1  0  0  0  0
 10 12  2  0  0  0  0
 10 17  1  0  0  0  0
 11 13  2  0  0  0  0
 11 18  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H

> <INCHI_KEY>
XDROKJSWHURZGO-UHFFFAOYSA-N

> <FORMULA>
C11H6O3

> <MOLECULAR_WEIGHT>
186.166

> <EXACT_MASS>
186.031694053

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
17.932909064997382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.9424830159999997

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.891181088107437

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
50.389700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
angelicin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Angelicin                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0       3.979  -3.218   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.745   1.166   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.122   3.518   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.436  -1.208   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.769  -0.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.103  -1.208   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.436  -2.748   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.103  -2.748   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.769  -3.518   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.979  -0.739   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.505  -0.428   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -1.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.517   1.176   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.128   1.978   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       8.930  -3.226   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       6.769  -4.473   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.682   0.169   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      10.326  -0.915   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.125  -1.978   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0      10.346   1.651   0.000  0.00  0.00           H+0
CONECT    1    7   12                                                       
CONECT    2    5   14                                                       
CONECT    3   14                                                            
CONECT    4    5    7   10                                                  
CONECT    5    2    4    6                                                  
CONECT    6    5    8   11                                                  
CONECT    7    1    4    9                                                  
CONECT    8    6    9   15                                                  
CONECT    9    7    8   16                                                  
CONECT   10    4   12   17                                                  
CONECT   11    6   13   18                                                  
CONECT   12    1   10   19                                                  
CONECT   13   11   14   20                                                  
CONECT   14    2    3   13                                                  
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Isopsoralen	ChEBI
2H-Furo[2,3-H]-1-benzopyran-2-one	HMDB
2H-Furo[2,3-H]chromen-2-one	HMDB
3-(4-Hydroxy-5-benzofuranyl)-2-propenoic acid gamma-lactone	HMDB
4-Hydroxy-5-benzofuranacrylic acid gamma-lactone	HMDB
Angecin	HMDB
Angelecin	HMDB
Bakuchicin	HMDB
Furo[2,3-H]coumarin	HMDB
Furo[5',4':7,8]coumarin	HMDB
Isopsoralin	HMDB

Chemical Formula

C₁₁H₆O₃

Average Mass

186.1660 Da

Monoisotopic Mass

186.03169 Da

IUPAC Name

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

Traditional Name

angelicin

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]

InChI Identifier

InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H

InChI Key

XDROKJSWHURZGO-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

furanocoumarin (CHEBI:28928 )
Furanocoumarins (C09060 )
a small molecule (CPD-9815 )

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	2.03	ALOGPS
logP	1.94	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-2.9	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	0	ChemAxon
Refractivity	50.39 m³·mol⁻¹	ChemAxon
Polarizability	17.93 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