Trioxsalen

Details

• Internal ID: ed48a266-4985-4ff5-93b6-579f7bbf5842
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: 2,5,9-trimethylfuro[3,2-g]chromen-7-one
• SMILES (Canonical): CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C
• SMILES (Isomeric): CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C
• 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
• InChI Key: FMHHVULEAZTJMA-UHFFFAOYSA-N
• Popularity: 804 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24 g/mol
• Exact Mass: 228.078644241 g/mol
• Topological Polar Surface Area (TPSA): 39.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 3902-71-4
• Trisoralen
• Trioxysalen
• Trimethylpsoralen
• 4,5',8-Trimethylpsoralen
• 2',4,8-Trimethylpsoralen
• NSC-71047
• 2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-one
• Elder 8011
• Trioxisaleno
• Trioxysalene
• Trioxysalenum
• 4,5',8-Trimethylpsoralene
• NSC71047
• Trioxsalen [USAN]
• 2,5,9-trimethylfuro[3,2-g]chromen-7-one
• 7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-
• Tmp (psoralen)
• 4,8,5'-Trimethylpsoralen
• Trioxysalene [INN-French]
• Trioxysalenum [INN-Latin]
• Trioxisaleno [INN-Spanish]
• NSC 71047
• 2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one
• Trioxysalen [INN]
• TRIOXSALIN
• Trioxsalen [USAN:USP]
• EINECS 223-459-0
• MFCD00005010
• 2,5,9-Trimethylpsoralen
• 4,5,8-Trimethylpsoralen
• Trisoralen;Trioxysalen;TMP
• UNII-Y6UY8OV51T
• BRN 0221723
• Y6UY8OV51T
• 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-
• DTXSID3023716
• CHEBI:28329
• 7-Oxo-2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyron
• NCGC00016643-01
• CAS-3902-71-4
• 6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid gamma-lactone
• 5-19-04-00472 (Beilstein Handbook Reference)
• DTXCID403716
• LACTONE
• 2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one
• 6-hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone
• SR-01000812969
• antipsoriatic
• Trioxalen
• Trixsalen
• Trisoralen (TN)
• Trioxsalen (USP)
• Prestwick_148
• 4,8-Trimethylpsoralen
• Spectrum_000169
• 4,8-Trimethylpsoralene
• TRIOXSALEN [MI]
• 2',8-Trimethylpsoralen
• Trioxysalen (JAN/INN)
• Prestwick0_000709
• Prestwick1_000709
• Prestwick2_000709
• Prestwick3_000709
• Spectrum2_001083
• Spectrum3_001378
• Spectrum4_000883
• Spectrum5_001557
• TRIOXYSALEN [JAN]
• TRIOXSALEN [VANDF]
• D0FA2O
• SCHEMBL1252
• CHEMBL1475
• TRIOXSALEN [USP-RS]
• TRIOXYSALEN [MART.]
• Oprea1_203343
• BSPBio_000897
• BSPBio_002936
• KBioGR_001286
• KBioSS_000649
• TRIOXYSALEN [WHO-DD]
• MLS001173417
• DivK1c_000380
• SPECTRUM1500596
• SPBio_001126
• SPBio_002818
• BPBio1_000987
• MEGxm0_000462
• TRIOXSALEN [ORANGE BOOK]
• ACon0_000603
• ACon1_000251
• HMS501C22
• KBio1_000380
• KBio2_000649
• KBio2_003217
• KBio2_005785
• KBio3_002156
• TRIOXSALEN [USP IMPURITY]
• 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
• 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
• LS-70743
• NCI60_038883
• SMR000538905
• 4,5',8-TRIMETHYLPSORALEN [IARC]
• SBI-0051547.P002
• FT-0603651
• 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
• Z1544404499
• 5-Benzofuranacrylic acid,2,7-trimethyl-, .delta.-lactone
• Trioxsalen, United States Pharmacopeia (USP) Reference Standard
• 6-hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid delta-lactone
• 5-Benzofuranacrylic acid, 6-hydroxy-.beta.,2,7-trimethyl-, .delta.-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.8587	85.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6853	68.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8061	80.61%
P-glycoprotein inhibitior	-	0.8491	84.91%
P-glycoprotein substrate	-	0.8908	89.08%
CYP3A4 substrate	-	0.5917	59.17%
CYP2C9 substrate	-	0.6642	66.42%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	+	0.6141	61.41%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.7328	73.28%
CYP2D6 inhibition	-	0.8415	84.15%
CYP1A2 inhibition	+	0.9217	92.17%
CYP2C8 inhibition	-	0.8743	87.43%
CYP inhibitory promiscuity	-	0.6083	60.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.3501	35.01%
Eye corrosion	-	0.9384	93.84%
Eye irritation	-	0.9541	95.41%
Skin irritation	+	0.5950	59.50%
Skin corrosion	-	0.9764	97.64%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6448	64.48%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.7874	78.74%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4691	46.91%
Acute Oral Toxicity (c)	IV	0.6314	63.14%
Estrogen receptor binding	+	0.6629	66.29%
Androgen receptor binding	+	0.7252	72.52%
Thyroid receptor binding	-	0.5836	58.36%
Glucocorticoid receptor binding	+	0.6894	68.94%
Aromatase binding	+	0.8213	82.13%
PPAR gamma	+	0.5983	59.83%
Honey bee toxicity	-	0.9241	92.41%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8952	89.52%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL251	P29274	Adenosine A2a receptor	1312 nM	IC50	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	3548.1 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	1000 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 3981.1 nM; 7943.3 nM; 3981.1 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	5623.4 nM; 281.8 nM; 281.8 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	6309.6 nM	Potency	via CMAUP
CHEMBL1951	P21397	Monoamine oxidase A	831 nM	IC50	via CMAUP
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	2356 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.62%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.59%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.44%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.47%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	86.64%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.32%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.84%	93.65%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	81.44%	95.70%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.07%	85.00%

Plants that contains it

• Apium graveolens
• Phellodendron amurense
• Phellodendron chinense

Cross-Links

• PubChem: 5585
• NPASS: NPC262635
• ChEMBL: CHEMBL1475
• LOTUS: LTS0132749
• wikiData: Q854263