Voacamine A - Compound Card

Voacamine A

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Voacamine A

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Iboga Alkaloid
Canonical Smiles c1(c(cc2c(c1)c1c([nH]2)[C@]2(C3N(CC1)CC(C2)C[C@@H]3CC)C(=O)OC)[C@H]1CC2/C(=C/C)/CN(C(Cc3c1[nH]c1c3cccc1)C2C(=O)OC)C)OC
InChI InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8+/t23?,24-,28?,31+,35?,37?,40?,43+/m0/s1
InChIKey VCMIRXRRQJNZJT-URFPYPRBSA-N
Formula C43H52N4O5
HBA 7
HBD 2
MW 704.91
Rotatable Bonds 5
TPSA 99.89
LogP 6.49
Number Rings 10
Number Aromatic Rings 4
Heavy Atom Count 52
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 704.39
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Voacanga africana Apocynaceae Plantae 141630

Showing of synonyms

  • Babiaka SB, Simoben CV, et al. (2020). Alkaloids with anti-onchocercal activity from Voacanga africana Stapf (Apocynaceae): identification and molecular modeling. Molecules, 2020, 26(1), 70. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc2[nH]c(c3c12)C(CC4C(=C)CNC(C4)C3)c(cc5)cc6[nH]c(c7c56)C8C9N(CC7)CC(C8)CC9

Level: 1

Mol. Weight: 704.91 g/mol

Structure

SMILES: c1cccc2[nH]c(c3c12)C4C5N(CC3)CC(C4)CC5

Level: 0

Mol. Weight: 704.91 g/mol

Structure

SMILES: C1C(C2)NCC(=C)C1CCc(c2c34)[nH]c3cccc4

Level: 0

Mol. Weight: 704.91 g/mol

Anti-onchocercal

Absorption

Caco-2 (logPapp)
-5.88
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
17.41
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3028.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.27
Plasma Protein Binding
63.1
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
12.04
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-74.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.56
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.51
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
-5495962.2
Rat (Acute)
2.81
Rat (Chronic Oral)
2.35
Fathead Minnow
6940.46
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
614697.94
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.54
Log(P)
5.97
Log S
-5.75
Log(Vapor Pressure)
-20183.68
Melting Point
264.01
pKa Acid
-109.29
pKa Basic
6.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8567
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8493
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8100
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8041
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.8030
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.8003
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7932
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7828
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7800
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7785
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7753
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7662
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7661
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7586
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7554
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7419
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7409
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7286
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7279
Transcriptional regulator URE2 P23202 URE2_YEAST Saccharomyces cerevisiae 3 0.7238
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7237
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7205
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7188
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7156
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7143
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7120
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7111
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7109
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.7095
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7065
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7050
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7049
(R)-S-adenosyl-L-methionine hydrolase O58212 O58212_PYRHO Pyrococcus horikoshii OT3 3 0.7033

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