Pleiocarpine - Compound Card

Pleiocarpine

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Pleiocarpine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COC(=O)[C@@H]1CC23CCCN4[C@@H]3[C@@]3(C1(CC2)N(C(=O)OC)c1c3cccc1)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
InChIKey SQVLFJQJOPEBAA-AUEHJUDRSA-N
Formula C23H28N2O4
HBA 5
HBD 0
MW 396.49
Rotatable Bonds 1
TPSA 59.08
LogP 3.09
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 396.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pleiocarpa pycnantha Apocynaceae Plantae 1220085

Showing of synonyms

  • Ndongo JT, Mbing JN, et al. (2018). Carbazole-, aspidofractinine-, and aspidocarpamine-type alkaloids from Pleiocarpa pycnantha.. Journal of natural products,2018, 81(5), 1193-1202. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc2c1NC3(C245)CCC6(CC3)C4N(CC5)CCC6

Level: 0

Mol. Weight: 396.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.48
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.890
Plasma Protein Binding
54.79
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.300
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.550
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.620
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.320
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-51.580
Rat (Acute)
3.890
Rat (Chronic Oral)
2.220
Fathead Minnow
3.970
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
460.720
Hydration Free Energy
-2.870
Log(D) at pH=7.4
2.840
Log(P)
2.59
Log S
-3.6
Log(Vapor Pressure)
-7.68
Melting Point
211.61
pKa Acid
9.18
pKa Basic
6.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8555
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7806
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7754
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7664
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7543
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7540
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7466
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7268
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7200
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7194
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7147
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7122
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7091
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7019

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