methyl (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11S,11aS,11bR)-3,11-dihydroxy-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-carboxylate

Details

• Internal ID: 3266c8fd-ca47-4c0e-88a3-9369c83f7908
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Jerveratrum-type alkaloids
• IUPAC Name: methyl (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11S,11aS,11bR)-3,11-dihydroxy-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-carboxylate
• SMILES (Canonical): CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(C4=C3C)O)C)O)C)N(C1)C(=O)OC
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5[C@@H](C4=C3C)O)C)O)C)N(C1)C(=O)OC
• InChI: InChI=1S/C29H43NO5/c1-15-12-22-25(30(14-15)27(33)34-5)17(3)29(35-22)11-9-20-21-7-6-18-13-19(31)8-10-28(18,4)24(21)26(32)23(20)16(29)2/h6,15,17,19-22,24-26,31-32H,7-14H2,1-5H3/t15-,17+,19-,20-,21-,22+,24+,25-,26+,28-,29-/m0/s1
• InChI Key: WPMPQHGQKMKABD-KIFCXFACSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₃NO₅
• Molecular Weight: 485.70 g/mol
• Exact Mass: 485.31412347 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 4.45
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9497	94.97%
Caco-2	-	0.6318	63.18%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5223	52.23%
OATP2B1 inhibitior	-	0.7164	71.64%
OATP1B1 inhibitior	+	0.8866	88.66%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9299	92.99%
P-glycoprotein inhibitior	+	0.5920	59.20%
P-glycoprotein substrate	+	0.6827	68.27%
CYP3A4 substrate	+	0.7284	72.84%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.7166	71.66%
CYP3A4 inhibition	-	0.8755	87.55%
CYP2C9 inhibition	-	0.8829	88.29%
CYP2C19 inhibition	-	0.8603	86.03%
CYP2D6 inhibition	-	0.8913	89.13%
CYP1A2 inhibition	-	0.8275	82.75%
CYP2C8 inhibition	+	0.6936	69.36%
CYP inhibitory promiscuity	-	0.8981	89.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4613	46.13%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9450	94.50%
Skin irritation	-	0.7566	75.66%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6515	65.15%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8498	84.98%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.5728	57.28%
Acute Oral Toxicity (c)	III	0.5305	53.05%
Estrogen receptor binding	+	0.7536	75.36%
Androgen receptor binding	+	0.7299	72.99%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.6962	69.62%
Aromatase binding	+	0.6448	64.48%
PPAR gamma	+	0.5812	58.12%
Honey bee toxicity	-	0.5819	58.19%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9388	93.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.95%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.26%	94.45%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	93.59%	89.05%
CHEMBL1871	P10275	Androgen Receptor	91.65%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.98%	97.09%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	88.74%	95.52%
CHEMBL5028	O14672	ADAM10	88.46%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.37%	96.95%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	88.13%	86.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.48%	94.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.17%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.23%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.10%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.93%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.74%	100.00%
CHEMBL2581	P07339	Cathepsin D	85.59%	98.95%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	85.20%	98.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.17%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.79%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	84.58%	90.17%
CHEMBL4072	P07858	Cathepsin B	84.31%	93.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.95%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.92%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.40%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.25%	91.07%
CHEMBL226	P30542	Adenosine A1 receptor	82.50%	95.93%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.35%	97.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.96%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.77%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	81.38%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.24%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.83%	95.89%

Plants that contains it

• Artemisia lagocephala
• Tanacetum parthenium

Cross-Links

• PubChem: 16723827
• NPASS: NPC166552