Voacangine hydroxyindolenine - Compound Card

Voacangine hydroxyindolenine

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Voacangine hydroxyindolenine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CC[C@H]1C[C@@H]2CN3[C@@H]1[C@](C2)(C(=O)OC)C1=Nc2c([C@@]1(CC3)O)cc(cc2)OC
InChI InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(25)28-3)18(14)24(12-13)8-7-22(26)16-10-15(27-2)5-6-17(16)23-19(21)22/h5-6,10,13-14,18,26H,4,7-9,11-12H2,1-3H3/t13-,14-,18-,21-,22+/m0/s1
InChIKey AVRFPRAAVSCSSZ-AIYLNWPXSA-N
Formula C22H28N2O4
HBA 6
HBD 1
MW 384.48
Rotatable Bonds 3
TPSA 71.36
LogP 2.65
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 384.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tabernaemontana penduliflora Apocynaceae Plantae 761088

Showing of synonyms

  • Bitombo AN, Zintchem AAA, et al. (2021). Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia,2021, 153, 104941. [View] [PubMed]
Pubchem: 14061707

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)N=C3C2CCN4C5C3CC(C4)CC5

Level: 0

Mol. Weight: 384.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
59.66
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.23
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.53
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.03
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
-19.8
Rat (Acute)
3.3
Rat (Chronic Oral)
1.84
Fathead Minnow
3.96
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
444.73
Hydration Free Energy
-5.99
Log(D) at pH=7.4
2.48
Log(P)
2.29
Log S
-3.36
Log(Vapor Pressure)
-8.17
Melting Point
192.28
pKa Acid
7.22
pKa Basic
6.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8909
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7964
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7933
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7617
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7573
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7486
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7483
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7372
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7303
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7219
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7161
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7118
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7101

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