[(1R,2S,5S,6S,9S,10S,13R,15R,16S,20S,23S,24R,25S,26S)-1,10,15,24,25,26-hexahydroxy-6,20,24-trimethyl-12-oxa-18-azaheptacyclo[13.12.0.02,13.05,10.06,13.016,25.018,23]heptacosan-9-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 3dfc00e6-f375-4615-a41c-2a597b3d8325
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
• IUPAC Name: [(1R,2S,5S,6S,9S,10S,13R,15R,16S,20S,23S,24R,25S,26S)-1,10,15,24,25,26-hexahydroxy-6,20,24-trimethyl-12-oxa-18-azaheptacyclo[13.12.0.02,13.05,10.06,13.016,25.018,23]heptacosan-9-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2(C3C1(COC24CC5(C6CN7CC(CCC7C(C6(C(CC5(C4CC3)O)O)O)(C)O)C)O)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC[C@]2([C@H]3[C@@]1(CO[C@@]24C[C@]5([C@@H]6CN7C[C@H](CC[C@H]7[C@@]([C@]6([C@H](C[C@]5([C@@H]4CC3)O)O)O)(C)O)C)O)O)C
• InChI: InChI=1S/C33H51NO9/c1-6-19(3)26(36)43-25-11-12-27(4)20-8-9-21-30(39)13-24(35)33(41)22(15-34-14-18(2)7-10-23(34)28(33,5)37)31(30,40)16-32(21,27)42-17-29(20,25)38/h6,18,20-25,35,37-41H,7-17H2,1-5H3/b19-6-/t18-,20-,21-,22-,23-,24-,25-,27-,28+,29+,30+,31+,32+,33-/m0/s1
• InChI Key: UWGBIKPRXRSRNM-MDGXCQEFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₁NO₉
• Molecular Weight: 605.80 g/mol
• Exact Mass: 605.35638220 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6210	62.10%
Caco-2	-	0.8001	80.01%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4630	46.30%
OATP2B1 inhibitior	-	0.5730	57.30%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9322	93.22%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8776	87.76%
BSEP inhibitior	+	0.8353	83.53%
P-glycoprotein inhibitior	+	0.6598	65.98%
P-glycoprotein substrate	+	0.6022	60.22%
CYP3A4 substrate	+	0.7164	71.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8026	80.26%
CYP3A4 inhibition	-	0.9724	97.24%
CYP2C9 inhibition	-	0.9252	92.52%
CYP2C19 inhibition	-	0.9262	92.62%
CYP2D6 inhibition	-	0.9362	93.62%
CYP1A2 inhibition	-	0.9352	93.52%
CYP2C8 inhibition	+	0.4901	49.01%
CYP inhibitory promiscuity	-	0.9785	97.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.5061	50.61%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9302	93.02%
Skin irritation	-	0.7181	71.81%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3615	36.15%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8387	83.87%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.8282	82.82%
Acute Oral Toxicity (c)	III	0.5749	57.49%
Estrogen receptor binding	+	0.7090	70.90%
Androgen receptor binding	+	0.7527	75.27%
Thyroid receptor binding	-	0.5252	52.52%
Glucocorticoid receptor binding	+	0.5962	59.62%
Aromatase binding	+	0.7448	74.48%
PPAR gamma	+	0.6594	65.94%
Honey bee toxicity	-	0.6997	69.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7386	73.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL284	P27487	Dipeptidyl peptidase IV	97.74%	95.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.14%	96.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	96.50%	89.05%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.93%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.75%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.02%	96.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.26%	92.94%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.36%	82.69%
CHEMBL2581	P07339	Cathepsin D	87.38%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.18%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.06%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.05%	97.21%
CHEMBL221	P23219	Cyclooxygenase-1	86.57%	90.17%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	86.28%	94.78%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.13%	97.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.06%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.00%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.43%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.39%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.35%	91.11%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.86%	89.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.73%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.22%	91.07%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	83.52%	80.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.63%	96.38%
CHEMBL340	P08684	Cytochrome P450 3A4	82.40%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	81.45%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.44%	97.09%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.16%	91.03%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.13%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.80%	99.23%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.13%	100.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.03%	95.71%

Plants that contains it

• Veratrum oblongum

Cross-Links

• PubChem: 162889893
• LOTUS: LTS0271019
• wikiData: Q105280341