Diacetoxyscirpenol

Details

• Internal ID: dfd0eb01-a9fc-405a-87f8-f6d404f9c764
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Trichothecenes
• IUPAC Name: [(1S,2R,7R,9R,10R,11S,12S)-11-acetyloxy-10-hydroxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-2-yl]methyl acetate
• InChI: InChI=1S/C19H26O7/c1-10-5-6-18(8-23-11(2)20)13(7-10)26-16-14(22)15(25-12(3)21)17(18,4)19(16)9-24-19/h7,13-16,22H,5-6,8-9H2,1-4H3/t13-,14-,15-,16-,17-,18-,19+/m1/s1
• InChI Key: AUGQEEXBDZWUJY-NMAPUUFXSA-N
• Popularity: 260 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₇
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.16785316 g/mol
• Topological Polar Surface Area (TPSA): 94.60 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Anguidine
• 2270-40-8
• Diazetoxyskirpenol [German]
• NSC 141537
• CCRIS 3536
• Diazetoxyskirpenol
• HSDB 7244
• EINECS 218-873-3
• UNII-UYL28I099N
• DTXSID80891791
• 12,13-Epoxytrichothec-9-ene-3alpha,4beta,15-triol 4,15-diacetate
• Scirpenetriol 4,15-diacetate
• ANG 66
• Scirp-9-ene-3alpha,4beta,15-triol, 4,15-diacetate
• NSC-177378
• 4beta,15-Diacetoxy-3alpha-hydroxy-12,13-epoxytrichothec-9-ene
• 3-alpha-Hydroxy-4-beta,15-diacetoxy-12,13-epoxytrichothec-9-ene
• Trichothec-9-ene, 12,13-epoxy-4beta,15-diazetoxy-3alpha-hydroxy-
• [(1S,2R,7R,9R,10R,11S,12S)-11-acetyloxy-10-hydroxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-2-yl]methyl acetate
• Trichothec-9-3n3-3,4,15-triol, 12,13-epoxy-, 4,15-diacetate, (3alpha,4beta)-
• NSC141537
• ((1S,2R,7R,9R,10R,11S,12S)-11-acetyloxy-10-hydroxy-1,5-dimethylspiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-2-yl)methyl acetate
• 11'-(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro(oxirane-2,12'-tricyclo(7.2.1.02,7)dodecan)-5'-en-2'-ylmethyl acetate
• 11'-(acetyloxy)-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.02,7]dodecan]-5'-en-2'-ylmethyl acetate
• 4alpha-hydroxy-12,13-epoxytrichothec-9-ene
• 4,15Diacetoxyscirpenol
• 4,15DiOacetylscirpenol
• 4,15Diacetoxyscirpen3ol
• RefChem:132551
• 4,15Diacetoxyscirp9en3ol
• Scirp-9-ene-3.alpha.,4.beta.,15-triol, 4,15-diacetate
• Scirpenetriol 4,15diacetate
• 4.beta.,15-Diacetoxy-3.alpha.-hydroxy-12,13-epoxytrichothec-9-ene
• Trichothec-9-ene, 12,13-epoxy-4-.beta.,15-diacetoxy-3-.alpha.-hydroxy-
• Trichothec-9-ene, 12,13-epoxy-4.beta.,15-diazetoxy-3.alpha.-hydroxy-
• DTXCID901031029
• ((1S,2R,7R,9R,10R,11S,12R)-11-acetyloxy-10-hydroxy-1,5-dimethylspiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-2-yl)methyl acetate
• (11-acetyloxy-10-hydroxy-1,5-dimethylspiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-2-yl)methyl acetate
• (11-acetyloxy-10-hydroxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-2-yl)methyl acetate
• [(1S,2R,7R,9R,10R,11S,12R)-11-acetyloxy-10-hydroxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-2-yl]methyl acetate
• Spiro(2,5-methano-1-benzoxepin-10,2'-oxirane)-5a(6H)-methanol, 2,3,4,5,7,9a-hexahydro-3,4-dihydroxy-5,8-dimethyl-, 4,5a-diacetate
• UN3462
• trichothec-9-ene-3alpha, 4beta, 15-triol, 12,13-epoxy-, 4,15-diacetate
• Scirp9ene3alpha,4beta,15triol, 4,15diacetate
• 3alphaHydroxy4beta,15diacetoxy12,13epoxytrichothec9ene
• 4beta,15Diacetoxy3alphahydroxy12,13epoxytrichothec9ene
• Trichothec9ene3,4,15triol, 12,13epoxy, 4,15diacetate
• Trichothec9ene, 12,13epoxy4beta,15diazetoxy3alphahydroxy
• 3Alpha,4Beta, 15-triol, 12, 13-epoxy-,4, 15-diacetate
• 3Alpha,4Beta, 15-triol, 12, 13-epoxy-,4, 15-diacetate (8CI)
• 4Beta, 15-diacetoxy-3alpha-hydroxy-12, 13-epoxytrichothec-9-ene
• Trichothec-9-ene-3,4, 15-triol, 12,13-epoxy-, 4,15-diacetate
• Trichothec-9-ene-3,4,15-triol, 12,13-epoxy-, 4, 15-diacetate
• Trichothec-9-ene, 12,13-epoxy-4-beta,15-diacetoxy-3-alpha-hydroxy-
• Trichothec-9-ene-3, 4, 15-triol, 12, 13-epoxy-, 4, 15-diacetate (3alpha, 4beta)-
• Trichothec-9-ene-3, 4,15-triol, 12,13-epoxy-, 4,15-diacetate, (3alpha,4beta)-
• Trichothec-9-ene-3,4, 15-triol, 12,13-epoxy-, 4,15-diacetate, (3alpha,4beta)-
• Trichothec-9-ene-3, 4, 15-triol, 12, 13-epoxy-, 4, 15-diacetate (3alpha, 4beta)-(9CI)
• Trichothec-9-ene-3, 4,15-triol, 12,13-epoxy-, 4,15-diacetate, (3.alpha.,4.beta.)-(9CI)
• Trichothec-9-ene-3,4, 15-triol, 12,13-epoxy-, 4,15-diacetate, (3.alpha.,4.beta.)-(9CI)
• AUGQEEXBDZWUJY-UHFFFAOYSA-N
• NSC177378
• Anguidin
• 4,15-Diacetoxyscirpen-3-ol
• 4,15-Di-O-acetylscirpenol
• MLS000863617
• UYL28I099N
• 4,15-Diacetoxyscirp-9-en-3-ol
• NSC-141537
• SMR000440757
• MM 4462
• Trichothec-9-ene-3.alpha.,4.beta.,15-triol, 12,13-epoxy-, 4,15-diacetate
• CHEMBL433680
• MEGxm0_000187
• SCHEMBL10994355
• ACon0_000396
• ACon1_002033
• BDBM68181
• MSK7223
• cid_15571694
• HMS2269N24
• HY-N6692
• MSK7223-100A
• NCGC00179895-01
• CS-0081332
• NS00018335
• C09662
• BRD-K51321215-001-01-2
• Diacetoxyscirpenol solution in Acetonitrile, 100ug/mL
• 3-Hydroxy-3alpha,4beta-12,13-epoxytrichothec-9-ene-4,15-diyl diacetate
• Trichothec-9-ene-3alpha,4beta,15-triol, 12,13-epoxy-, 4,15-diacetate
• 109547-11-7
• Trichothec-9-ene-3,4,15-triol, 12,13-epoxy-, 4,15-diacetate, (3.alpha.,4.beta.,12.alpha.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9004	90.04%
Caco-2	+	0.5815	58.15%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7705	77.05%
OATP2B1 inhibitior	-	0.8637	86.37%
OATP1B1 inhibitior	+	0.8695	86.95%
OATP1B3 inhibitior	+	0.9367	93.67%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6271	62.71%
BSEP inhibitior	-	0.5218	52.18%
P-glycoprotein inhibitior	-	0.6241	62.41%
P-glycoprotein substrate	-	0.8147	81.47%
CYP3A4 substrate	+	0.6531	65.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8358	83.58%
CYP3A4 inhibition	-	0.9190	91.90%
CYP2C9 inhibition	-	0.7978	79.78%
CYP2C19 inhibition	-	0.8500	85.00%
CYP2D6 inhibition	-	0.9276	92.76%
CYP1A2 inhibition	-	0.7389	73.89%
CYP2C8 inhibition	-	0.6038	60.38%
CYP inhibitory promiscuity	-	0.8829	88.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6371	63.71%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9228	92.28%
Skin irritation	-	0.5631	56.31%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6703	67.03%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.6499	64.99%
skin sensitisation	-	0.8433	84.33%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.8551	85.51%
Acute Oral Toxicity (c)	I	0.8324	83.24%
Estrogen receptor binding	+	0.8453	84.53%
Androgen receptor binding	+	0.6431	64.31%
Thyroid receptor binding	+	0.5382	53.82%
Glucocorticoid receptor binding	+	0.6492	64.92%
Aromatase binding	-	0.5745	57.45%
PPAR gamma	+	0.6592	65.92%
Honey bee toxicity	-	0.7947	79.47%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6755	67.55%
Fish aquatic toxicity	+	0.9899	98.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	100 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	89.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.40%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.88%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.76%	97.25%
CHEMBL2581	P07339	Cathepsin D	88.47%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.52%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.77%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.63%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.31%	94.00%
CHEMBL5028	O14672	ADAM10	84.85%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	83.98%	94.73%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.68%	98.75%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.27%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.54%	89.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 15571694
• LOTUS: LTS0109227
• wikiData: Q104918914