Trioxsalen
PubChem CID: 5585
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| Compound Synonyms | trioxsalen, 3902-71-4, Trioxysalen, Trisoralen, 4,5',8-Trimethylpsoralen, Trimethylpsoralen, Trioxisaleno, Trioxysalene, 2',4,8-Trimethylpsoralen, Trioxysalenum, NSC-71047, 2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-one, Elder 8011, 4,5',8-Trimethylpsoralene, NSC71047, Tmp (psoralen), 4,8,5'-Trimethylpsoralen, 2,5,9-trimethylfuro[3,2-g]chromen-7-one, 7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-, Y6UY8OV51T, 2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one, Trioxysalen [INN], TRIOXSALIN, DTXSID3023716, CHEBI:28329, MFCD00005010, Trisoralen, Trioxysalen, TMP, 2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyran-7-one, 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,5,9-trimethyl-, DTXCID403716, NCGC00016643-01, CAS-3902-71-4, 6-hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone, TRIOXSALEN (USP-RS), TRIOXSALEN [USP-RS], TRIOXYSALEN (MART.), TRIOXYSALEN [MART.], Trioxsalen [USAN], 2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one, TRIOXSALEN (USP IMPURITY), TRIOXSALEN [USP IMPURITY], Trioxisalenum, Trioxysalene [INN-French], Trioxysalenum [INN-Latin], Trioxisaleno [INN-Spanish], NSC 71047, 4,5',8-TRIMETHYLPSORALEN (IARC), 4,5',8-TRIMETHYLPSORALEN [IARC], LACTONE, 2,5,9-trimethyl-7H-furo(3,2-g)chromen-7-one, SR-01000812969, Trioxsalen [USAN:USP], EINECS 223-459-0, 2,5,9-Trimethylpsoralen, 4,5,8-Trimethylpsoralen, UNII-Y6UY8OV51T, antipsoriatic, BRN 0221723, trioxisalene, Trioxalen, Trixsalen, Trisoralen (TN), Trioxsalen (USP), Prestwick_148, 7-Oxo-2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyron, Trioxsalen (Standard), 4,8-Trimethylpsoralen, Spectrum_000169, 4,8-Trimethylpsoralene, TRIOXSALEN [MI], 2',8-Trimethylpsoralen, Trioxysalen (JAN/INN), 6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid gamma-lactone, Prestwick0_000709, Prestwick1_000709, Prestwick2_000709, Prestwick3_000709, Spectrum2_001083, Spectrum3_001378, Spectrum4_000883, Spectrum5_001557, TRIOXYSALEN [JAN], TRIOXSALEN [VANDF], SCHEMBL1252, CHEMBL1475, Oprea1_203343, BSPBio_000897, BSPBio_002936, KBioGR_001286, KBioSS_000649, TRIOXYSALEN [WHO-DD], 5-19-04-00472 (Beilstein Handbook Reference), MLS001173417, DivK1c_000380, SPECTRUM1500596, 2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-one, SPBio_001126, SPBio_002818, BPBio1_000987, MEGxm0_000462, TRIOXSALEN [ORANGE BOOK], ACon0_000603, ACon1_000251, HMS501C22, HY-B1157R, KBio1_000380, KBio2_000649, KBio2_003217, KBio2_005785, KBio3_002156, D05AD01, D05BA01, NINDS_000380, HMS1570M19, HMS1921I05, HMS2092A12, HMS2097M19, HMS2879M06, HMS3714M19, Pharmakon1600-01500596, 7H-Furo[3, 2,5,9-trimethyl-, HY-B1157, Tox21_110541, CCG-39937, NSC757371, STL564342, AKOS015912601, Tox21_110541_1, Trioxsalen, >=98% (HPLC), powder, CS-4760, DB04571, FT47227, KS-5184, NSC-757371, SDCCGMLS-0066609.P001, IDI1_000380, NCGC00016643-02, NCGC00016643-03, NCGC00016643-04, NCGC00016643-05, NCGC00016643-06, NCGC00016643-09, NCGC00016643-10, NCGC00094804-01, NCGC00094804-02, NCGC00178384-01, NCGC00178384-02, NCGC00178384-03, 1ST40159, NCI60_038883, SMR000538905, SBI-0051547.P002, DB-049366, NS00015856, T2267, BENZOFURANACRYLIC ACID,2,7-TRIMETHYL-,, C09314, D01034, EN300-122631, T72416, 4,7,9-trimethyl-2H-furo[3,2-g]chromen-2-one, AB00052119_09, 2,5,9-trimethyl-7-furo[3,2-g][1]benzopyranone, A824380, Q854263, 2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-one #, SR-01000812969-2, SR-01000812969-5, SR-01000812969-6, SR-01000812969-7, 2,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one, BRD-K54790157-001-06-4, BRD-K54790157-001-10-6, BRD-K54790157-001-15-5, Z1544404499, 5-Benzofuranacrylic acid,2,7-trimethyl-, .delta.-lactone, Trioxsalen, 2,5,9-Trimethyl-furo[3,2-g]benzopyran-7-one, 5-Benzofuranacrylic acid, 6-hydroxy-.beta.,2,7-trimethyl-, .delta.-lactone, 223-459-0 |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 39.4 |
| Hydrogen Bond Donor Count | 0.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | CC1CCC2CC3CCCC3CC2C1 |
| Np Classifier Class | Furocoumarins, Simple coumarins |
| Deep Smiles | Ccccco5)cC)ccc6)cC)cc=O)o6 |
| Heavy Atom Count | 17.0 |
| Classyfire Class | Coumarins and derivatives |
| Description | Trioxsalen, also known as trimethylpsoralen or trisoralen, is a member of the class of compounds known as psoralens. Psoralens 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. Trioxsalen is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Trioxsalen can be found in wild celery, which makes trioxsalen a potential biomarker for the consumption of this food product. Trioxsalen can be found primarily in blood and urine. Trioxsalen (trimethylpsoralen, Trioxysalen or Trisoralen) is a furanocoumarin and a psoralen derivative. It is obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo and hand eczema. After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage. The compound is also being explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair . Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue (DrugBank). |
| Scaffold Graph Node Level | OC1CCC2CC3CCOC3CC2O1 |
| Classyfire Subclass | Furanocoumarins |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 374.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | n.a., B2RXH2, P00352, P28482, P08684, Q96QE3, P05177, P83916, P29274, P21397, P28335, P43220, P01215, O42275, P81908, Q9Y6L6, Q9NPD5, P27695, O95342, P0DTD1, P10275 |
| Iupac Name | 2,5,9-trimethylfuro[3,2-g]chromen-7-one |
| Prediction Hob | 1.0 |
| Class | Coumarins and derivatives |
| Veber Rule | True |
| Classyfire Superclass | Phenylpropanoids and polyketides |
| Target Id | NPT48, NPT94, NPT282, NPT109, NPT208, NPT217, NPT261, NPT292 |
| Xlogp | 3.0 |
| Superclass | Phenylpropanoids and polyketides |
| Subclass | Furanocoumarins |
| Gsk 4 400 Rule | True |
| Molecular Formula | C14H12O3 |
| Scaffold Graph Node Bond Level | O=c1ccc2cc3ccoc3cc2o1 |
| Prediction Swissadme | 0.0 |
| Inchi Key | FMHHVULEAZTJMA-UHFFFAOYSA-N |
| Silicos It Class | Moderately soluble |
| Fcsp3 | 0.2142857142857142 |
| Logs | -5.546 |
| Rotatable Bond Count | 0.0 |
| State | Solid |
| Logd | 3.304 |
| Synonyms | 2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyran-7-one, 2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one, 2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-one, 2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one, 2,5,9-Trimethylpsoralen, 2',4,8-Trimethylpsoralen, 4,5',8-Trimethylpsoralen, 7-Oxo-2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyron, 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,5,9-trimethyl-, 7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-, Antipsoriatic, Trimethylpsoralen, Trioxysalen, Trisoralen, 4,8,5'-Trimethylpsoralen, 6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone, Trioxisaleno, Trioxysalene, Trioxysalenum, 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, delta-lactone, 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone, 6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylate, delta-lactone, 6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylate, δ-lactone, 6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactone, 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, δ-lactone, 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactone, Trioxisalenum, 2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-one, ICN brand OF trioxsalen, trimethylpsoralen, trioxsalen |
| Esol Class | Soluble |
| Functional Groups | c=O, coc |
| Compound Name | Trioxsalen |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 228.079 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 228.079 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 228.24 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Lipinski Rule Of 5 | True |
| Esol | -3.270013752941176 |
| Inchi | InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3 |
| Smiles | CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C |
| Nring | 3.0 |
| Np Classifier Biosynthetic Pathway | Shikimates and Phenylpropanoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Psoralens |
| Np Classifier Superclass | Coumarins |
- 1. Outgoing r'ship
FOUND_INto/from Apium Graveolens (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Phellodendron Amurense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Phellodendron Chinense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Phellodendron Chinese (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all