Voacristine hydroxyindolenine - Compound Card

Voacristine hydroxyindolenine

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Voacristine hydroxyindolenine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COC(=O)[C@@]12C[C@@H]3CN([C@H]1[C@H](C3)[C@@H](O)C)CCC1(C2=Nc2c1cc(cc2)OC)O
InChI InChI=1S/C22H28N2O5/c1-12(25)15-8-13-10-21(20(26)29-3)18(15)24(11-13)7-6-22(27)16-9-14(28-2)4-5-17(16)23-19(21)22/h4-5,9,12-13,15,18,25,27H,6-8,10-11H2,1-3H3/t12-,13+,15+,18-,21-,22?/m0/s1
InChIKey MMANMJCGIGNJGH-DCDXYTRWSA-N
Formula C22H28N2O5
HBA 7
HBD 2
MW 400.48
Rotatable Bonds 3
TPSA 91.59
LogP 1.62
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 400.2
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: 101281074

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 400.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.970
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.570
Plasma Protein Binding
50.41
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.770
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.470
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.570
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.010
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
-26.610
Rat (Acute)
2.920
Rat (Chronic Oral)
1.890
Fathead Minnow
4.060
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
420.490
Hydration Free Energy
-5.290
Log(D) at pH=7.4
1.640
Log(P)
0.85
Log S
-2.67
Log(Vapor Pressure)
-9.0
Melting Point
185.51
pKa Acid
6.66
pKa Basic
6.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8857
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8659
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8249
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7867
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7819
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7578
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7493
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7484
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7481
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7475
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7365
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7344
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7242
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7211
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7155
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7141
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7102
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7060

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