Natural Product (NP) Details

General Information of the NP (ID: NP9823)
Name
Xanthotoxin
Synonyms
methoxsalen; 8-Methoxypsoralen; 298-81-7; XANTHOTOXIN; Ammoidin; Meladinine; Xanthotoxine; 8-MOP; Meloxine; Oxsoralen; 9-Methoxy-7H-furo[3,2-g]chromen-7-one; Meladinin; Oxypsoralen; Puvalen; Meladoxen; Ammodin; Uvadex; Methoxa-Dome; 8-Methoxypsoralene; Oxsoralen-ultra; New-Meladinin; Geroxalen; Methoxalen; Puvamet; Oxsoralen lotion; Zanthotoxin; Psoralon-MOP; 9-Methoxypsoralen; 8-MP; 8-Methoxyfuranocoumarin; 9-methoxyfuro[3,2-g]chromen-7-one; 9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one; O-methylxanthotoxol; 8-Methoxy-2',3',6,7-furocoumarin; 7H-Furo[3,2-g][1]benzopyran-7-one, 9-methoxy-; NCI-C55903; Methoxy-8-psoralen; 8-Methoxy-4',5',6,7-furocoumarin; 6-Hydroxy-7-methoxy-5-benzofuranacrylic acid delta-lactone; Methoxsalen-d3; UNII-U4VJ29L7BQ; 8-Methoxy-[furano-3'.2':6.7-coumarin]; NSC45923; MFCD00005009; NSC 45923; 8-Methoxy-4',5':6,7-furocoumarin; 8-Methoxy-(furano-3'.2':6.7-coumarin); 9-Methoxyfuro[3,2-g][1]benzopyran-7-one; Methoxsalen (Oxsoralen); 9-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one; 9-Methoxyfuro(3,2-g)chromen-7-one; CHEMBL416; Oxsoralen Ultra; 7H-Furo(3,2-G)(1)benzopyran-7-one, 9-methoxy-; U4VJ29L7BQ; 8-Methoxy-6,7-furanocoumarin; CHEBI:18358; 9-(methyloxy)-7H-furo[3,2-g]chromen-7-one; Proralone-mop; NSC-45923; 9-methoxyfurano[3,2-g]chromen-2-one; Meladinin (VAN); NCGC00016418-07; CAS-298-81-7; Methoxaten; Oxoralen; ST041029; DSSTox_CID_830; 8-Methoxypsoralen, 99%; Ultra Mop; DSSTox_RID_75816; DSSTox_GSID_20830; 1246819-63-5; Deltapsoralen; Dltasoralen; Methoxsalene; Metoxaleno; Methoxsalen, 8-; SMR000071170; CCRIS 2083; HSDB 2505; 8-Methoxypsoralen with ultraviolet A therapy; OXSORALEN (TN); SR-01000629727; EINECS 206-066-9; Methoxsalen plus ultraviolet radiation; BRN 0196453; Vitpso; Methoxsalen [USP:BAN:JAN]; 9-Methoxy-7H-furo(3,2-g)benzopyran-7-one; 5-Benzofuranacrylic acid, 6-hydroxy-7-methoxy-, delta-lactone; Prestwick_661; Spectrum_001023; 5-Demethoxyisoimpinellin; 8-Methoxy(furano-3'.2':6.7-coumarin); Prestwick0_000479; Prestwick1_000479; Prestwick2_000479; Prestwick3_000479; Spectrum2_001052; Spectrum3_000499; Spectrum4_000052; Spectrum5_001891; UVADEX (TN); Methoxsalen (JP17/USP); 7H-Furo[3, 9-methoxy-; Oprea1_166319; SCHEMBL19168; BSPBio_000618; BSPBio_001997; KBioGR_000543; KBioSS_001503; 5-19-06-00015 (Beilstein Handbook Reference); 8MO; MLS000062633; MLS002303011; DivK1c_000763; SPECTRUM1500400; SPBio_001004; SPBio_002557; BPBio1_000680; MEGxp0_000095; Xanthotoxin, analytical standard; DTXSID8020830; ACon1_000174; HMS502G05; KBio1_000763; KBio2_001503; KBio2_004071; KBio2_006639; KBio3_001497; 8-Methoxy Psoralen-[13C,d3]; 8-Methoxy-2',6,7-furocoumarin; 8-Methoxy-4',6,7-furocoumarin; NINDS_000763; HMS1569O20; HMS1920N05; HMS2091D20; HMS2096O20; HMS2269P03; HMS3259L13; HMS3655B05; HMS3884K16; Pharmakon1600-01500400; 5-Benzofuranacrylic acid, 6-hydroxy-7-methoxy-, .delta.-lactone; BCP28212; SM-88 COMPONENT METHOXSALEN; ZINC2548959; Tox21_110432; Tox21_201767; Tox21_302816; 8-Methoxypsoralen;Xanthotoxin;8-MOP; BDBM50041234; CCG-36366; NSC757114; s1952; SBB005950; STK735539; WLN: T C566 DO LVOJ BO1; 8-Methoxypsoralen, analytical standard; AKOS000277012; Tox21_110432_1; 9-Methoxy-furo[3,2-g]chromen-7-one; AC-4259; AM84906; CS-1983; DB00553; DS-5159; MCULE-2500932325; NC00652; NSC-757114; SDCCGMLS-0042377.P002; IDI1_000763; 8-methoxy-2'',3'',6,7-furocoumarin; 8-methoxy-4'',5'':6,7-furocoumarin; NCGC00016418-01; NCGC00016418-02; NCGC00016418-03; NCGC00016418-04; NCGC00016418-05; NCGC00016418-06; NCGC00016418-08; NCGC00016418-09; NCGC00016418-10; NCGC00016418-11; NCGC00016418-12; NCGC00016418-14; NCGC00016418-15; NCGC00060938-02; NCGC00060938-03; NCGC00060938-04; NCGC00060938-05; NCGC00060938-06; NCGC00178871-01; NCGC00178871-02; NCGC00178871-03; NCGC00256435-01; NCGC00259316-01; AK111265; HY-30151; NCI60_004085; Q039; SBI-0051443.P003; FT-0602101; FT-0671145; N1305; SW167762-4; 8-methoxy-[furano-3''.2'':6.7-coumarin]; 9-Methoxy-7H-furo[3,2-g]chromen-7-one #; EN300-52504; C01864; D00139; J10204; 9-(Trideuteriomethoxy)furo[3,2-g]chromen-7-one; AB00052042-14; AB00052042-15; AB00052042_16; AB00052042_17; 298M817; 9-METHOXY-2H-FURO[3,2-G]CHROMEN-2-ONE; 9-Methoxy-7H-furo[3,2- g][1]benzopyran-7-one; Q408570; Q-100381; SR-01000629727-2; SR-01000629727-4; BRD-K63430059-001-03-2; BRD-K63430059-001-06-5; BRD-K63430059-001-09-9; Z1258578369; Methoxsalen, United States Pharmacopeia (USP) Reference Standard; 12692-94-3
    Click to Show/Hide
Species Origin Cullen corylifolium ...     Click to Show/Hide
Cullen corylifolium
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Cullen
Species: Cullen corylifolium
Disease Mycosis fungoides [ICD-11: 2B01] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C12H8O4
PubChem CID
4114
Canonical SMILES
COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2
InChI
1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChIKey
QXKHYNVANLEOEG-UHFFFAOYSA-N
CAS Number
CAS 298-81-7
ChEBI ID
CHEBI:18358
Herb ID
HBIN048463
SymMap ID
SMIT01660
TTD Drug ID
D08SKH
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Levetiracetam + Valproic acid     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Adult male Albino Swiss mice weighing 22-26 g were used in this study.
                    Experimental
                    Result(s)		 XANT in combination with levetiracetam exerts beneficial anticonvulsant pharmacodynamic interactions in the 6 Hz mouse psychomotor seizure model.
          Ketoconazole + Amphotericin B     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Candida albicans ATCC 22972 Microorganism model Candida albicans
Candida glabrata ATCC 90525 Microorganism model Candida glabrata
Candida guilliermondii ATCC 20216 Microorganism model Candida guilliermondii
Candida krusei ATCC 6258 Microorganism model Candida krusei
Candida parapsilosis ATCC 7330 Microorganism model Candida parapsilosis
Candida tropicalis ATCC 42678 Microorganism model Candida tropicalis
                    Experimental
                    Result(s)		 1/2 MIC dose of xanthorrhizol in combination with 1/2 MIC dose of ketoconazole or 1/2 MIC dose of amphotericin B exhibited growth inhibition of all Candida species tested and reduced viable cells by several logs within 4 h.
Target and Pathway
Target(s) Cytochrome P450 2A6 (CYP2A6)  Molecule Info  [4]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 009048.
Reference 2 Xanthotoxin enhances the anticonvulsant potency of levetiracetam and valproate in the 6-Hz corneal stimulation model in mice. Fundam Clin Pharmacol. 2021 Jul 2.
Reference 3 Synergistic anticandidal activity of xanthorrhizol in combination with ketoconazole or amphotericin B. FEMS Yeast Res. 2009 Dec;9(8):1302-11.
Reference 4 Mutagenicity and carcinogenicity of methoxsalen plus UV-A. Arch Dermatol. 1984 May;120(5):662-9.
 Download Picture         KEGG Link