(1S,4S,5S,6S,9E,11S,14S,15R,16S)-4,6-dihydroxy-5-methoxy-9,13,14-trimethyl-16-(2-methylpropyl)-17-azatricyclo[9.7.0.01,15]octadeca-9,12-diene-2,18-dione

Details

• Internal ID: 0c727603-994c-44b3-9b97-2542c032ffeb
• Taxonomy: Alkaloids and derivatives > Cytochalasans > Aspochalasins
• IUPAC Name: (1S,4S,5S,6S,9E,11S,14S,15R,16S)-4,6-dihydroxy-5-methoxy-9,13,14-trimethyl-16-(2-methylpropyl)-17-azatricyclo[9.7.0.01,15]octadeca-9,12-diene-2,18-dione
• SMILES (Canonical): CC1C2C(NC(=O)C23C(C=C(CCC(C(C(CC3=O)O)OC)O)C)C=C1C)CC(C)C
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H](NC(=O)[C@@]23[C@@H](/C=C(/CC[C@@H]([C@@H]([C@H](CC3=O)O)OC)O)\C)C=C1C)CC(C)C
• InChI: InChI=1S/C25H39NO5/c1-13(2)9-18-22-16(5)15(4)11-17-10-14(3)7-8-19(27)23(31-6)20(28)12-21(29)25(17,22)24(30)26-18/h10-11,13,16-20,22-23,27-28H,7-9,12H2,1-6H3,(H,26,30)/b14-10+/t16-,17+,18+,19+,20+,22+,23+,25-/m1/s1
• InChI Key: VDFBOYQHOXIVOC-LJICDNDHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₉NO₅
• Molecular Weight: 433.60 g/mol
• Exact Mass: 433.28282334 g/mol
• Topological Polar Surface Area (TPSA): 95.90 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9824	98.24%
Caco-2	-	0.5470	54.70%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6242	62.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8913	89.13%
OATP1B3 inhibitior	+	0.9212	92.12%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6322	63.22%
BSEP inhibitior	-	0.6517	65.17%
P-glycoprotein inhibitior	-	0.6352	63.52%
P-glycoprotein substrate	+	0.5962	59.62%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8329	83.29%
CYP3A4 inhibition	-	0.8850	88.50%
CYP2C9 inhibition	-	0.6960	69.60%
CYP2C19 inhibition	-	0.7481	74.81%
CYP2D6 inhibition	-	0.9268	92.68%
CYP1A2 inhibition	-	0.7829	78.29%
CYP2C8 inhibition	-	0.7187	71.87%
CYP inhibitory promiscuity	-	0.6465	64.65%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5686	56.86%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9668	96.68%
Skin irritation	-	0.7157	71.57%
Skin corrosion	-	0.9138	91.38%
Ames mutagenesis	-	0.6991	69.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.6549	65.49%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.5194	51.94%
skin sensitisation	-	0.8509	85.09%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8214	82.14%
Acute Oral Toxicity (c)	III	0.4290	42.90%
Estrogen receptor binding	+	0.6442	64.42%
Androgen receptor binding	+	0.6655	66.55%
Thyroid receptor binding	+	0.5822	58.22%
Glucocorticoid receptor binding	+	0.6683	66.83%
Aromatase binding	-	0.5070	50.70%
PPAR gamma	+	0.5815	58.15%
Honey bee toxicity	-	0.7979	79.79%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.6801	68.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.33%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.25%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.99%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.15%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.33%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.83%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.32%	93.03%
CHEMBL2996	Q05655	Protein kinase C delta	86.95%	97.79%
CHEMBL213	P08588	Beta-1 adrenergic receptor	86.23%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.62%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.33%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.25%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.24%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.75%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.31%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.28%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.86%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.68%	86.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.86%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.26%	94.75%

Plants that contains it

• Ericameria laricifolia

Cross-Links

• PubChem: 44575563
• NPASS: NPC474725
• ChEMBL: CHEMBL480485
• LOTUS: LTS0055945
• wikiData: Q105284117