Perakine - Compound Card

Perakine

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Perakine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles O=C[C@@H]1C2C[C@@H]3N([C@H]1C)[C@@H]1C2[C@@H](OC(=O)C)[C@]2(C3=Nc3c2cccc3)C1
InChI InChI=1S/C21H22N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,9-10,12-13,16-18,20H,7-8H2,1-2H3/t10-,12?,13-,16-,17-,18?,20+,21+/m0/s1
InChIKey GDXJMOGWONJRHL-HWUILILVSA-N
Formula C21H22N2O3
HBA 5
HBD 0
MW 350.42
Rotatable Bonds 2
TPSA 58.97
LogP 2.25
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 350.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Rauvolfia caffra Apocynaceae Plantae 947877
2 Tabernaemontana inconspicua Apocynaceae Plantae 761075

Showing of synonyms

  • Foudjo Melacheu Laura G, Mfotie Njoya E, et al. (2021). A new cytotoxic indole alkaloid from Tabernaemontana inconspicua stapf. Natural product research,2021, 35(10), 1590-1595. [View] [PubMed]
  • Bitombo AN, Zintchem AAA, et al. (2022). Antimicrobial and cytotoxic activities of indole alkaloids and other constituents from the stem barks of Rauvolfia caffra Sond (Apocynaceae). Natural product research,2022, 36(6), 1467-1475. [View] [PubMed]
Pubchem: 453213
Nmrshiftdb2: 60064064

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1C234)N=C2C5N6C(C4)C(C3)C(C5)CC6

Level: 0

Mol. Weight: 350.42 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.89
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.800
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.520
Plasma Protein Binding
50.31
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.060
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-0.570
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.380
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.000
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
-10.450
Rat (Acute)
4.350
Rat (Chronic Oral)
1.060
Fathead Minnow
4.110
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
430.510
Hydration Free Energy
-3.100
Log(D) at pH=7.4
1.360
Log(P)
1.65
Log S
-3.22
Log(Vapor Pressure)
-8.75
Melting Point
212.39
pKa Acid
6.36
pKa Basic
7.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8567
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8550
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7576
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7572
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7153
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7130
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7061
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7019

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