Voacorine - Compound Card

Voacorine

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Voacorine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COC(=O)C1C2CC(c3cc4[nH]c5c(c4cc3OC)CCN3C4C5(CC(C3)CC4C(O)C)C(=O)OC)c3c(CC1N(C/C/2=C\C)C)c1ccccc1[nH]3
InChI InChI=1S/C43H52N4O6/c1-7-24-21-46(3)35-17-32-25-10-8-9-11-33(25)44-38(32)31(15-28(24)37(35)41(49)52-5)30-16-34-29(18-36(30)51-4)26-12-13-47-20-23-14-27(22(2)48)40(47)43(19-23,39(26)45-34)42(50)53-6/h7-11,16,18,22-23,27-28,31,35,37,40,44-45,48H,12-15,17,19-21H2,1-6H3/b24-7+
InChIKey UIEKMUULTFWIHX-HCBMXOAHSA-N
Formula C43H52N4O6
HBA 8
HBD 3
MW 720.91
Rotatable Bonds 5
TPSA 120.12
LogP 5.46
Number Rings 10
Number Aromatic Rings 4
Heavy Atom Count 53
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 720.39
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Tabernaemontana brachyantha Apocynaceae Plantae 761053

Showing of synonyms

  • Patel Mb, Thompson LS, et al. (1973). Alcaldoïes de Tabernaemontana brachyantha. Phytochemistry, 1973, 12, 451-456. [View]
Pubchem: 6444471

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: 720.91 g/mol

Structure

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

Level: 0

Mol. Weight: 720.91 g/mol

Structure

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

Level: 0

Mol. Weight: 720.91 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.0
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
26.970
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
4290.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.120
Plasma Protein Binding
31.45
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
11.470
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-105.000
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.660
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.340
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
-7785384.450
Rat (Acute)
2.860
Rat (Chronic Oral)
2.430
Fathead Minnow
9830.670
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
872021.480
Hydration Free Energy
-2.920
Log(D) at pH=7.4
4.640
Log(P)
4.51
Log S
-5.32
Log(Vapor Pressure)
-28660.76
Melting Point
262.95
pKa Acid
-165.63
pKa Basic
5.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9399
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8829
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8090
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8073
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7935
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7823
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.7773
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7738
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7727
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7712
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7709
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7549
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7486
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7479
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7426
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7393
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7318
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7309
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7243
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7226
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7226
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7199
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7184
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7181
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7129
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7117
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7085
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7074
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7031
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7020

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