(1R,3S,3'R,3'aS,4aR,6'S,6aS,6bS,7'aR,9R,11aS,11bS)-1,3-dihydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,4a,5,6,6a,6b,7,8,11a-dodecahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-11-one

Details

• Internal ID: dab804a1-3cd7-4255-a091-db3ad6165e39
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Jerveratrum-type alkaloids
• IUPAC Name: (1R,3S,3'R,3'aS,4aR,6'S,6aS,6bS,7'aR,9R,11aS,11bS)-1,3-dihydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,4a,5,6,6a,6b,7,8,11a-dodecahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-11-one
• SMILES (Canonical): CC1CC2C(C(C3(O2)CCC4C5CCC6CC(CC(C6(C5C(=O)C4=C3C)C)O)O)C)NC1
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC[C@@H]6C[C@@H](C[C@H]([C@@]6([C@H]5C(=O)C4=C3C)C)O)O)C)NC1
• InChI: InChI=1S/C27H41NO4/c1-13-9-20-24(28-12-13)15(3)27(32-20)8-7-18-19-6-5-16-10-17(29)11-21(30)26(16,4)23(19)25(31)22(18)14(27)2/h13,15-21,23-24,28-30H,5-12H2,1-4H3/t13-,15+,16+,17-,18-,19-,20+,21+,23+,24-,26+,27-/m0/s1
• InChI Key: RGTMFUMMFMNSOX-ZFSYBBPOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₁NO₄
• Molecular Weight: 443.60 g/mol
• Exact Mass: 443.30355879 g/mol
• Topological Polar Surface Area (TPSA): 78.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9584	95.84%
Caco-2	-	0.5642	56.42%
Blood Brain Barrier	-	0.5144	51.44%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5704	57.04%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.8573	85.73%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7128	71.28%
BSEP inhibitior	-	0.5117	51.17%
P-glycoprotein inhibitior	-	0.6156	61.56%
P-glycoprotein substrate	+	0.5069	50.69%
CYP3A4 substrate	+	0.6879	68.79%
CYP2C9 substrate	-	0.7688	76.88%
CYP2D6 substrate	-	0.8070	80.70%
CYP3A4 inhibition	-	0.9741	97.41%
CYP2C9 inhibition	-	0.9259	92.59%
CYP2C19 inhibition	-	0.9258	92.58%
CYP2D6 inhibition	-	0.9412	94.12%
CYP1A2 inhibition	-	0.8775	87.75%
CYP2C8 inhibition	+	0.4590	45.90%
CYP inhibitory promiscuity	-	0.9179	91.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4574	45.74%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9593	95.93%
Skin irritation	-	0.6619	66.19%
Skin corrosion	-	0.9136	91.36%
Ames mutagenesis	-	0.6465	64.65%
Human Ether-a-go-go-Related Gene inhibition	-	0.3808	38.08%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7980	79.80%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.4874	48.74%
Acute Oral Toxicity (c)	III	0.6133	61.33%
Estrogen receptor binding	+	0.6679	66.79%
Androgen receptor binding	+	0.7124	71.24%
Thyroid receptor binding	+	0.6130	61.30%
Glucocorticoid receptor binding	+	0.8021	80.21%
Aromatase binding	+	0.6625	66.25%
PPAR gamma	-	0.5417	54.17%
Honey bee toxicity	-	0.7182	71.82%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7335	73.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL241	Q14432	Phosphodiesterase 3A	95.00%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.40%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.28%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.20%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.97%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.22%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.10%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.68%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	89.19%	94.75%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	88.84%	90.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.58%	95.56%
CHEMBL1871	P10275	Androgen Receptor	87.55%	96.43%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.09%	89.05%
CHEMBL4072	P07858	Cathepsin B	85.84%	93.67%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.28%	93.03%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.20%	96.38%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.68%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.52%	86.33%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	80.95%	88.84%
CHEMBL3045	P05771	Protein kinase C beta	80.52%	97.63%

Plants that contains it

• Artemisia lagocephala
• Tanacetum parthenium

Cross-Links

• PubChem: 16723933
• NPASS: NPC300682