[(1S,8S,10S,11R,12S,13S)-3,11-dihydroxy-4,12-dimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.18,11.01,10.02,7]octadeca-2(7),3,5-trien-13-yl] (E)-3-phenylprop-2-enoate

Details

• Internal ID: c94ef9f5-f745-44ea-9c54-99ba7598b8c2
• Taxonomy: Alkaloids and derivatives > Hasubanan alkaloids
• IUPAC Name: [(1S,8S,10S,11R,12S,13S)-3,11-dihydroxy-4,12-dimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.18,11.01,10.02,7]octadeca-2(7),3,5-trien-13-yl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CN1CCC23C14CC(C5=C2C(=C(C=C5)OC)O)OC4(C(C(C3)OC(=O)C=CC6=CC=CC=C6)OC)O
• SMILES (Isomeric): CN1CC[C@@]23[C@]14C[C@@H](C5=C2C(=C(C=C5)OC)O)O[C@]4([C@H]([C@H](C3)OC(=O)/C=C/C6=CC=CC=C6)OC)O
• InChI: InChI=1S/C28H31NO7/c1-29-14-13-26-15-21(35-22(30)12-9-17-7-5-4-6-8-17)25(34-3)28(32)27(26,29)16-20(36-28)18-10-11-19(33-2)24(31)23(18)26/h4-12,20-21,25,31-32H,13-16H2,1-3H3/b12-9+/t20-,21-,25-,26-,27-,28-/m0/s1
• InChI Key: HIDHXGLBVLLDSU-DRIBXIMTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₁NO₇
• Molecular Weight: 493.50 g/mol
• Exact Mass: 493.21005233 g/mol
• Topological Polar Surface Area (TPSA): 97.70 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8655	86.55%
Caco-2	-	0.6049	60.49%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4391	43.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8878	88.78%
OATP1B3 inhibitior	+	0.9124	91.24%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9349	93.49%
P-glycoprotein inhibitior	+	0.8043	80.43%
P-glycoprotein substrate	+	0.6442	64.42%
CYP3A4 substrate	+	0.6948	69.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7794	77.94%
CYP3A4 inhibition	-	0.7561	75.61%
CYP2C9 inhibition	-	0.8849	88.49%
CYP2C19 inhibition	-	0.8250	82.50%
CYP2D6 inhibition	-	0.8605	86.05%
CYP1A2 inhibition	-	0.9070	90.70%
CYP2C8 inhibition	+	0.6941	69.41%
CYP inhibitory promiscuity	-	0.9135	91.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4873	48.73%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9405	94.05%
Skin irritation	-	0.7989	79.89%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8279	82.79%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6092	60.92%
skin sensitisation	-	0.8611	86.11%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.9235	92.35%
Acute Oral Toxicity (c)	III	0.5209	52.09%
Estrogen receptor binding	+	0.7930	79.30%
Androgen receptor binding	+	0.7856	78.56%
Thyroid receptor binding	+	0.6815	68.15%
Glucocorticoid receptor binding	+	0.7682	76.82%
Aromatase binding	+	0.5702	57.02%
PPAR gamma	+	0.6766	67.66%
Honey bee toxicity	-	0.8054	80.54%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5055	50.55%
Fish aquatic toxicity	+	0.9813	98.13%

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	98.29%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.65%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.57%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.39%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.82%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.95%	98.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	92.00%	94.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.31%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.83%	93.99%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	88.43%	96.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.44%	96.00%
CHEMBL5028	O14672	ADAM10	85.79%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.51%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.20%	97.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.04%	99.23%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.52%	89.44%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.13%	91.07%
CHEMBL2056	P21728	Dopamine D1 receptor	82.72%	91.00%
CHEMBL2535	P11166	Glucose transporter	81.06%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.55%	97.14%

Plants that contains it

• Stephania longa

Cross-Links

• PubChem: 11656161
• LOTUS: LTS0089905
• wikiData: Q105028772