Pleiocarpine

Details

• Internal ID: 51b3f159-08ff-451b-8a66-750a19006900
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: dimethyl (1R,9R,16R,18R,21S)-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3,5,7-triene-2,18-dicarboxylate
• SMILES (Canonical): COC(=O)C1CC23CCCN4C2C5(C1(CC3)N(C6=CC=CC=C65)C(=O)OC)CC4
• SMILES (Isomeric): COC(=O)[C@@H]1C[C@]23CCCN4[C@@H]2[C@@]5([C@]1(CC3)N(C6=CC=CC=C65)C(=O)OC)CC4
• InChI: InChI=1S/C23H28N2O4/c1-28-18(26)16-14-21-8-5-12-24-13-11-22(19(21)24)15-6-3-4-7-17(15)25(20(27)29-2)23(16,22)10-9-21/h3-4,6-7,16,19H,5,8-14H2,1-2H3/t16-,19-,21+,22+,23+/m0/s1
• InChI Key: SQVLFJQJOPEBAA-VTDVIBAZSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈N₂O₄
• Molecular Weight: 396.50 g/mol
• Exact Mass: 396.20490738 g/mol
• Topological Polar Surface Area (TPSA): 59.10 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9170	91.70%
Caco-2	+	0.7109	71.09%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6720	67.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8967	89.67%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.8089	80.89%
P-glycoprotein inhibitior	+	0.6137	61.37%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6673	66.73%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	+	0.4097	40.97%
CYP3A4 inhibition	-	0.5776	57.76%
CYP2C9 inhibition	-	0.6895	68.95%
CYP2C19 inhibition	-	0.6635	66.35%
CYP2D6 inhibition	-	0.7436	74.36%
CYP1A2 inhibition	-	0.6257	62.57%
CYP2C8 inhibition	-	0.6965	69.65%
CYP inhibitory promiscuity	-	0.6803	68.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6612	66.12%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9789	97.89%
Skin irritation	-	0.8262	82.62%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7494	74.94%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8795	87.95%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5621	56.21%
Acute Oral Toxicity (c)	III	0.5594	55.94%
Estrogen receptor binding	+	0.5950	59.50%
Androgen receptor binding	+	0.7443	74.43%
Thyroid receptor binding	-	0.6022	60.22%
Glucocorticoid receptor binding	+	0.5622	56.22%
Aromatase binding	+	0.5259	52.59%
PPAR gamma	-	0.5197	51.97%
Honey bee toxicity	-	0.8908	89.08%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9678	96.78%

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	96.65%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.49%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.16%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.10%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.77%	86.33%
CHEMBL4208	P20618	Proteasome component C5	90.29%	90.00%
CHEMBL5028	O14672	ADAM10	87.24%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.58%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.43%	82.69%

Plants that contains it

• Hunteria camerunensis
• Hunteria umbellata
• Kopsia arborea
• Kopsia dasyrachis
• Kopsia griffithii

Cross-Links

• PubChem: 101650372
• LOTUS: LTS0207273
• wikiData: Q105258647