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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:42:16 UTC

Update Date

2023-02-21 17:23:46 UTC

HMDB ID

HMDB0033930

Secondary Accession Numbers

HMDB33930

Metabolite Identification

Common Name

Angelicin

Description

Angelicin, also known as isopsoralen, 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. Angelicin is found, on average, in the highest concentration within parsnips (Pastinaca sativa). Angelicin has also been detected, but not quantified in, several different foods, such as figs (Ficus carica), green vegetables, wild celeries (Apium graveolens), corianders (Coriandrum sativum), and herbs and spices. This could make angelicin a potential biomarker for the consumption of these foods. Angelicin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Angelicin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0033930

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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 Molecular Weight

186.166

Monoisotopic Molecular Weight

186.031694053

IUPAC Name

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

Traditional Name

angelicin

CAS Registry Number

523-50-2

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

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 )

Ontology

Physiological effect

Health effect

Edema (HMDB: HMDB0033930)

Skin and subcutaneous tissue disorder

Erythema (HMDB: HMDB0033930)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033930)
Cytoplasm (HMDB: HMDB0033930)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033930)

Source

Exogenous

Food

Food (HMDB: HMDB0033930)

Vegetable

Root vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Coriander (FooDB: FOOD00061)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Other fruit

Fig (FooDB: FOOD00081)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0033930)

Process

Not Available

Role

Biological role

Industrial application

Antiviral agent (HMDB: HMDB0033930)
Central nervous system depressant (HMDB: HMDB0033930)

Pharmaceutical industry

Hepatoprotective (HMDB: HMDB0033930)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Sedative (HMDB: HMDB0033930)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	138 - 139.5 °C	Not Available
Boiling Point	360.00 to 362.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	859.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.08	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.603	31661259
DarkChem	[M-H]-	137.836	31661259
DeepCCS	[M+H]+	155.892	30932474
DeepCCS	[M-H]-	153.496	30932474
DeepCCS	[M-2H]-	187.202	30932474
DeepCCS	[M+Na]+	162.205	30932474
AllCCS	[M+H]+	137.3	32859911
AllCCS	[M+H-H2O]+	132.7	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	137.2	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	136.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Angelicin	[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]	3057.9	Standard polar	33892256
Angelicin	[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]	1826.2	Standard non polar	33892256
Angelicin	[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]	1848.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Angelicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-052o-1900000000-e433073a06547646bc69	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Angelicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-2900000000-b75bda2977a6c5f4a825	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 10V, Positive-QTOF	splash10-000i-0900000000-aa1adff2459dc4ba52de	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 20V, Positive-QTOF	splash10-000i-0900000000-e3913fd1e50c49b503cc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 40V, Positive-QTOF	splash10-00kb-0900000000-1a7322ca712708e85891	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 10V, Negative-QTOF	splash10-000i-0900000000-0fb3e93d63c26fc514f3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 20V, Negative-QTOF	splash10-000i-0900000000-9305ce66dc73cd6363e7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 40V, Negative-QTOF	splash10-00ko-1900000000-d860e98711eaf835ef5d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 10V, Positive-QTOF	splash10-000i-0900000000-f3f07adc83a68e9e76ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 20V, Positive-QTOF	splash10-0a4r-0900000000-5d2c49a45303742805c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 40V, Positive-QTOF	splash10-0a59-0900000000-a5ec76b52b95bb267d30	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 10V, Negative-QTOF	splash10-000i-0900000000-89e4df10d3690e5a6d15	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 20V, Negative-QTOF	splash10-000i-0900000000-89e4df10d3690e5a6d15	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Angelicin 40V, Negative-QTOF	splash10-0a4r-0900000000-97a40f647a23cfa5279b	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Angelicin

METLIN ID

Not Available

PubChem Compound

10658

PDB ID

Not Available

ChEBI ID

28928

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1010821

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Angelicin (HMDB0033930)

MOL for HMDB0033930 (Angelicin)

3D MOL for HMDB0033930 (Angelicin)

3D SDF for HMDB0033930 (Angelicin)

3D-SDF for HMDB0033930 (Angelicin)

PDB for HMDB0033930 (Angelicin)

3D PDB for HMDB0033930 (Angelicin)

SMILES for HMDB0033930 (Angelicin)

INCHI for HMDB0033930 (Angelicin)

Structure for HMDB0033930 (Angelicin)

3D Structure for HMDB0033930 (Angelicin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra