[(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-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: 2faa08ae-30c4-4ce2-bf68-48610cf29d43
• Taxonomy: Alkaloids and derivatives > Hasubanan alkaloids
• IUPAC Name: [(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-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): COC1C(CC23CCNC24C1(OC(C4)C5=C3C(=C(C=C5)OC)O)OC)OC(=O)C=CC6=CC=CC=C6
• SMILES (Isomeric): CO[C@H]1[C@H](C[C@]23CCN[C@]24[C@]1(O[C@@H](C4)C5=C3C(=C(C=C5)OC)O)OC)OC(=O)/C=C/C6=CC=CC=C6
• InChI: InChI=1S/C28H31NO7/c1-32-19-11-10-18-20-16-27-26(13-14-29-27,23(18)24(19)31)15-21(25(33-2)28(27,34-3)36-20)35-22(30)12-9-17-7-5-4-6-8-17/h4-12,20-21,25,29,31H,13-16H2,1-3H3/b12-9+/t20-,21-,25-,26-,27-,28-/m0/s1
• InChI Key: OKJXULSSFGSEHT-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): 95.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9430	94.30%
Caco-2	-	0.6255	62.55%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4974	49.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8754	87.54%
OATP1B3 inhibitior	+	0.9239	92.39%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9810	98.10%
P-glycoprotein inhibitior	+	0.7971	79.71%
P-glycoprotein substrate	+	0.5563	55.63%
CYP3A4 substrate	+	0.6737	67.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8011	80.11%
CYP3A4 inhibition	-	0.6446	64.46%
CYP2C9 inhibition	-	0.8328	83.28%
CYP2C19 inhibition	-	0.7791	77.91%
CYP2D6 inhibition	-	0.8457	84.57%
CYP1A2 inhibition	-	0.8178	81.78%
CYP2C8 inhibition	+	0.8234	82.34%
CYP inhibitory promiscuity	-	0.7873	78.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4704	47.04%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9502	95.02%
Skin irritation	-	0.7650	76.50%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8631	86.31%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5092	50.92%
skin sensitisation	-	0.7742	77.42%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8544	85.44%
Acute Oral Toxicity (c)	III	0.4512	45.12%
Estrogen receptor binding	+	0.8266	82.66%
Androgen receptor binding	+	0.7825	78.25%
Thyroid receptor binding	+	0.7229	72.29%
Glucocorticoid receptor binding	+	0.7612	76.12%
Aromatase binding	+	0.6186	61.86%
PPAR gamma	+	0.7710	77.10%
Honey bee toxicity	-	0.8050	80.50%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	+	0.8509	85.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.48%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	97.08%	94.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.13%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.93%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.87%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.35%	97.09%
CHEMBL4302	P08183	P-glycoprotein 1	92.17%	92.98%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.05%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.90%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	90.76%	94.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.64%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.59%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.52%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.86%	93.00%
CHEMBL5028	O14672	ADAM10	87.60%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.37%	95.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	87.02%	97.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.06%	89.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.87%	93.99%
CHEMBL2535	P11166	Glucose transporter	84.54%	98.75%
CHEMBL221	P23219	Cyclooxygenase-1	83.38%	90.17%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.87%	89.44%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.77%	91.07%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.66%	91.71%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.28%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	80.07%	91.19%

Plants that contains it

• Stephania longa

Cross-Links

• PubChem: 11620179
• LOTUS: LTS0234742
• wikiData: Q105193599