Angelicin
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Basic Info
| Common Name | Angelicin(F03904) |
| 2D Structure | |
| Description | Angelicin is found in coriander. Angelicin is a constituent of roots and leaves of angelica (Angelica archangelica). Angelicin is found in roots and on surface of parsnips and diseased celery.Angelicin is a furanocoumarin. It can be found in Bituminaria bituminosa. It is present in the list of IARC Group 3 carcinogens (Angelicin plus ultraviolet A radiation). (Wikipedia). |
| FRCD ID | F03904 |
| CAS Number | 523-50-2 |
| PubChem CID | 10658 |
| Formula | C11H6O3 |
| IUPAC Name | furo[2,3-h]chromen-2-one |
| InChI Key | XDROKJSWHURZGO-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H |
| Canonical SMILES | C1=CC2=C(C=CO2)C3=C1C=CC(=O)O3 |
| Isomeric SMILES | C1=CC2=C(C=CO2)C3=C1C=CC(=O)O3 |
| Wikipedia | Angelicin |
| Synonyms |
2H-Furo[2,3-H]chromen-2-one
Angelicin
ISOPSORALEN
523-50-2
Angecin
furo[2,3-h]chromen-2-one
Isopsoralin
Furo(2,3-h)coumarin
Angelecin
Angelicin (coumarin derivative)
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Coumarins and derivatives |
| Subclass | Furanocoumarins |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Angular furanocoumarins |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 186.166 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Complexity | 284 |
| Monoisotopic Mass | 186.032 |
| Exact Mass | 186.032 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9719 |
| Human Intestinal Absorption | HIA+ | 0.9966 |
| Caco-2 Permeability | Caco2+ | 0.6155 |
| P-glycoprotein Substrate | Non-substrate | 0.6821 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8056 |
| Non-inhibitor | 0.8922 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8028 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6286 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8208 |
| CYP450 2D6 Substrate | Non-substrate | 0.9092 |
| CYP450 3A4 Substrate | Non-substrate | 0.7451 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9107 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5345 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.6769 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7951 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7675 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6336 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9023 |
| Non-inhibitor | 0.9689 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.9509 |
| Fish Toxicity | High FHMT | 0.8638 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9449 |
| Honey Bee Toxicity | High HBT | 0.7961 |
| Biodegradation | Not ready biodegradable | 0.7153 |
| Acute Oral Toxicity | II | 0.7408 |
| Carcinogenicity (Three-class) | Warning | 0.4491 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2949 | LogS |
| Caco-2 Permeability | 1.2133 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4984 | LD50, mol/kg |
| Fish Toxicity | 0.3975 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5187 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Quantitative Analysis of Psoralea corylifolia Linne and its Neuroprotective and Anti-Neuroinflammatory Effects in HT22 Hippocampal Cells and BV-2 Microglia. | Molecules | 2016 Aug 17 | 27548120 |
| Isolation and purification of psoralen and isopsoralen and their efficacy and safety in the treatment of osteosarcoma in nude rats. | Afr Health Sci | 2014 Sep | 25352883 |
Targets
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 Da
References
- Girennavar B, Jayaprakasha GK, Patil BS: Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J Food Sci. 2007 Oct;72(8):C417-21. [17995595 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Girennavar B, Jayaprakasha GK, Patil BS: Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J Food Sci. 2007 Oct;72(8):C417-21. [17995595 ]
- General Function:
- Transcriptional repressor activity, rna polymerase ii transcription regulatory region sequence-specific binding
- Specific Function:
- NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related to many biological processes such as inflammation, immunity, differentiation, cell growth, tumorigenesis and apoptosis. NF-kappa-B is a homo- or heterodimeric complex formed by the Rel-like domain-containing proteins RELA/p65, RELB, NFKB1/p105, NFKB1/p50, REL and NFKB2/p52 and the heterodimeric p65-p50 complex appears to be most abundant one. The dimers bind at kappa-B sites in the DNA of their target genes and the individual dimers have distinct preferences for different kappa-B sites that they can bind with distinguishable affinity and specificity. Different dimer combinations act as transcriptional activators or repressors, respectively. NF-kappa-B is controlled by various mechanisms of post-translational modification and subcellular compartmentalization as well as by interactions with other cofactors or corepressors. NF-kappa-B complexes are held in the cytoplasm in an inactive state complexed with members of the NF-kappa-B inhibitor (I-kappa-B) family. In a conventional activation pathway, I-kappa-B is phosphorylated by I-kappa-B kinases (IKKs) in response to different activators, subsequently degraded thus liberating the active NF-kappa-B complex which translocates to the nucleus. NF-kappa-B heterodimeric p65-p50 and RelB-p50 complexes are transcriptional activators. The NF-kappa-B p50-p50 homodimer is a transcriptional repressor, but can act as a transcriptional activator when associated with BCL3. NFKB1 appears to have dual functions such as cytoplasmic retention of attached NF-kappa-B proteins by p105 and generation of p50 by a cotranslational processing. The proteasome-mediated process ensures the production of both p50 and p105 and preserves their independent function, although processing of NFKB1/p105 also appears to occur post-translationally. p50 binds to the kappa-B consensus sequence 5'-GGRNNYYCC-3', located in the enhancer region of genes involved in immune response and acute phase reactions. In a complex with MAP3K8, NFKB1/p105 represses MAP3K8-induced MAPK signaling; active MAP3K8 is released by proteasome-dependent degradation of NFKB1/p105.
- Gene Name:
- NFKB1
- Uniprot ID:
- P19838
- Molecular Weight:
- 105355.175 Da
References
- Piccagli L, Borgatti M, Nicolis E, Bianchi N, Mancini I, Lampronti I, Vevaldi D, Dall'Acqua F, Cabrini G, Gambari R: Virtual screening against nuclear factor kappaB (NF-kappaB) of a focus library: Identification of bioactive furocoumarin derivatives inhibiting NF-kappaB dependent biological functions involved in cystic fibrosis. Bioorg Med Chem. 2010 Dec 1;18(23):8341-9. doi: 10.1016/j.bmc.2010.09.063. Epub 2010 Oct 1. [20980154 ]