Psoralen
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Basic Info
| Common Name | Psoralen(F03909) |
| 2D Structure | |
| Description | Psoralen is found in carrot. Psoralen is found in common vegetables, e.g. parsnip, celery especially if diseased or `spoiled' Psoralen is a significant mutagen and is used for this purpose in molecular biology research. Psoralen has been shown to exhibit anti-proliferative, anti-allergenic and anti-histamine functions (A7781, A7782, A7782). Psoralen belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity. |
| FRCD ID | F03909 |
| CAS Number | 66-97-7 |
| PubChem CID | 6199 |
| Formula | C11H6O3 |
| IUPAC Name | furo[3,2-g]chromen-7-one |
| InChI Key | ZCCUUQDIBDJBTK-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H |
| Canonical SMILES | C1=CC(=O)OC2=CC3=C(C=CO3)C=C21 |
| Isomeric SMILES | C1=CC(=O)OC2=CC3=C(C=CO3)C=C21 |
| Wikipedia | Psoralen |
| Synonyms |
7H-Furo[3,2-g][1]benzopyran-7-one
Psoralen
66-97-7
Ficusin
7H-Furo[3,2-g]chromen-7-one
Furocoumarin
Psoralene
Psorline-P
6,7-Furanocoumarin
furo[3,2-g]chromen-7-one
|
| 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 | Linear furanocoumarins |
| Direct Parent | Psoralens |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Psoralen - Benzopyran - 1-benzopyran - Benzofuran - Pyranone - Benzenoid - Pyran - Furan - Heteroaromatic compound - Lactone - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. |
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 | 2.3 |
| 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 |
|---|---|---|---|
| Topical Bixin Confers NRF2-Dependent Protection Against Photodamage and HairGraying in Mouse Skin. | Front Pharmacol | 2018 Mar 27 | 29636694 |
| Antimicrobial evaluation of red, phytoalexin-rich sorghum food biocolorant. | PLoS One | 2018 Mar 21 | 29561885 |
| Resveratrol-Potential Antibacterial Agent against Foodborne Pathogens. | Front Pharmacol | 2018 Feb 19 | 29515440 |
| Isoflavones and anti-inflammatory constituents from the fruits of Psoralea corylifolia. | Phytochemistry | 2017 Nov | 28825980 |
| Resveratrol Reactivates Latent HIV through Increasing Histone Acetylation andActivating Heat Shock Factor 1. | J Agric Food Chem | 2017 Jun 7 | 28471170 |
| Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I. | Molecules | 2017 Jul 27 | 28749423 |
| Protective effects of resveratrol against mancozeb induced apoptosis damage inmouse oocytes. | Oncotarget | 2017 Jan 24 | 28031523 |
| An Overview of Stress-Induced Resveratrol Synthesis in Grapes: Perspectives forResveratrol-Enriched Grape Products. | Molecules | 2017 Feb 14 | 28216605 |
| Psoralea corylifolia extract induces vasodilation in rat arteries through bothendothelium-dependent and -independent mechanisms involving inhibition of TRPC3channel activity and elaboration of prostaglandin. | Pharm Biol | 2017 Dec | 28982307 |
| Involvement of endogenous salicylic acid in iron-deficiency responses inArabidopsis. | J Exp Bot | 2016 Jul | 27208542 |
| 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 |
| Resveratrol attenuates lipopolysaccharide-induced acute kidney injury by suppressing inflammation driven by macrophages. | Mol Nutr Food Res | 2015 May | 25643926 |
| The Phytoalexin Resveratrol Ameliorates Ochratoxin A Toxicity in Human Embryonic Kidney (HEK293) Cells. | J Cell Biochem | 2015 Dec | 26095584 |
| Secondary metabolites in fungus-plant interactions. | Front Plant Sci | 2015 Aug 6 | 26300892 |
| 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 |
| Resveratrol inhibits IgE-mediated basophilic mast cell degranulation and passive cutaneous anaphylaxis in mice. | J Nutr | 2013 May | 23514766 |
| Phytoalexin transgenics in crop protection--fairy tale with a happy end? | Plant Sci | 2012 Oct | 22920999 |
| Grape variety related trans-resveratrol induction affects Aspergillus carbonarius growth and ochratoxin A biosynthesis. | Int J Food Microbiol | 2012 May 15 | 22483545 |
| Metabolism and metabolites of dithiocarbamates in the plant pathogenic fungusLeptosphaeria maculans. | J Agric Food Chem | 2012 Aug 15 | 22823278 |
| [Study on the chemical constituents of Psoralea corylifolia]. | Zhong Yao Cai | 2011 Aug | 22233033 |
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 ]