12-Hydroxy-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,18,20-triene-26,2'-oxirane]-11,17,22-trione

Details

• Internal ID: 017422b2-6cfc-4024-af63-ad0517c2004d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Trichothecenes
• IUPAC Name: 12-hydroxy-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,18,20-triene-26,2'-oxirane]-11,17,22-trione
• SMILES (Canonical): CC1CCOC(=O)C=CC=CC(=O)OC2CC3C4(C2(C5(CCC(=CC5O3)C)COC(=O)C1O)C)CO4
• SMILES (Isomeric): CC1CCOC(=O)C=CC=CC(=O)OC2CC3C4(C2(C5(CCC(=CC5O3)C)COC(=O)C1O)C)CO4
• InChI: InChI=1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3
• InChI Key: NLUGUZJQJYVUHS-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₉
• Molecular Weight: 502.60 g/mol
• Exact Mass: 502.22028266 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.17
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• MLS002703008
• 379Y
• Neuro_000061
• CHEMBL1733059
• SMR001566816
• FT-0603630

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9407	94.07%
Caco-2	-	0.6936	69.36%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8006	80.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8417	84.17%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6150	61.50%
BSEP inhibitior	+	0.9770	97.70%
P-glycoprotein inhibitior	+	0.7448	74.48%
P-glycoprotein substrate	+	0.7892	78.92%
CYP3A4 substrate	+	0.6809	68.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8833	88.33%
CYP3A4 inhibition	-	0.9097	90.97%
CYP2C9 inhibition	-	0.8623	86.23%
CYP2C19 inhibition	-	0.8906	89.06%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	-	0.7872	78.72%
CYP2C8 inhibition	-	0.6433	64.33%
CYP inhibitory promiscuity	-	0.9756	97.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5899	58.99%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9539	95.39%
Skin irritation	-	0.5638	56.38%
Skin corrosion	-	0.9255	92.55%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6860	68.60%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.8616	86.16%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6572	65.72%
Acute Oral Toxicity (c)	I	0.5069	50.69%
Estrogen receptor binding	+	0.8256	82.56%
Androgen receptor binding	+	0.7478	74.78%
Thyroid receptor binding	-	0.5235	52.35%
Glucocorticoid receptor binding	+	0.7976	79.76%
Aromatase binding	+	0.6699	66.99%
PPAR gamma	+	0.6445	64.45%
Honey bee toxicity	-	0.6900	69.00%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9785	97.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	< 195 nM	AC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.43%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.22%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.71%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.29%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.86%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.61%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.58%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.03%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.79%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.06%	94.80%
CHEMBL1871	P10275	Androgen Receptor	84.88%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.86%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.03%	93.04%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.16%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.03%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.80%	93.40%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.85%	98.75%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.57%	81.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.34%	96.95%
CHEMBL2581	P07339	Cathepsin D	80.10%	98.95%

Plants that contains it

• Baccharis coridifolia
• Gymnanthemum amygdalinum

Cross-Links

• PubChem: 104830
• NPASS: NPC313921
• ChEMBL: CHEMBL1733059
• LOTUS: LTS0197272
• wikiData: Q105181570