methyl (Z)-2-[(3E)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate

Details

• Internal ID: 8658ef48-d88c-4dc2-8aa6-7bc291a81fbe
• Taxonomy: Alkaloids and derivatives > Corynanthean-type alkaloids
• IUPAC Name: methyl (Z)-2-[(3E)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate
• SMILES (Canonical): CC=C1CN2CCC3=C(C2CC1C(=CO)C(=O)OC)NC4=CC=CC=C34
• SMILES (Isomeric): C/C=C\1/CN2CCC3=C(C2CC1/C(=C/O)/C(=O)OC)NC4=CC=CC=C34
• InChI: InChI=1S/C21H24N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,12,16,19,22,24H,8-11H2,1-2H3/b13-3-,17-12-
• InChI Key: WKWHYFHGTWZCLM-BJSCZJAFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.40 g/mol
• Exact Mass: 352.17869263 g/mol
• Topological Polar Surface Area (TPSA): 65.60 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.65
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	+	0.7624	76.24%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7461	74.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8860	88.60%
OATP1B3 inhibitior	+	0.9288	92.88%
MATE1 inhibitior	-	0.6637	66.37%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8796	87.96%
P-glycoprotein inhibitior	+	0.6069	60.69%
P-glycoprotein substrate	+	0.5460	54.60%
CYP3A4 substrate	+	0.7157	71.57%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.7984	79.84%
CYP3A4 inhibition	-	0.6016	60.16%
CYP2C9 inhibition	-	0.5758	57.58%
CYP2C19 inhibition	-	0.8994	89.94%
CYP2D6 inhibition	+	0.6994	69.94%
CYP1A2 inhibition	+	0.5713	57.13%
CYP2C8 inhibition	+	0.6356	63.56%
CYP inhibitory promiscuity	-	0.7598	75.98%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6907	69.07%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9823	98.23%
Skin irritation	-	0.7518	75.18%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8806	88.06%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8655	86.55%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5864	58.64%
Acute Oral Toxicity (c)	III	0.5600	56.00%
Estrogen receptor binding	+	0.6217	62.17%
Androgen receptor binding	+	0.6461	64.61%
Thyroid receptor binding	+	0.5236	52.36%
Glucocorticoid receptor binding	+	0.6370	63.70%
Aromatase binding	-	0.7565	75.65%
PPAR gamma	-	0.5463	54.63%
Honey bee toxicity	-	0.8098	80.98%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9718	97.18%

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	98.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.22%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.08%	94.45%
CHEMBL240	Q12809	HERG	95.94%	89.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.41%	95.56%
CHEMBL2535	P11166	Glucose transporter	88.98%	98.75%
CHEMBL5028	O14672	ADAM10	87.72%	97.50%
CHEMBL1914	P06276	Butyrylcholinesterase	86.25%	95.00%
CHEMBL255	P29275	Adenosine A2b receptor	84.82%	98.59%
CHEMBL4208	P20618	Proteasome component C5	82.42%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.27%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.68%	97.09%

Plants that contains it

• Catharanthus roseus
• Rauvolfia volkensii
• Rhazya stricta

Cross-Links

• PubChem: 10043592
• LOTUS: LTS0228806
• wikiData: Q105246515