Desacetylvindoline - Compound Card

Desacetylvindoline

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Desacetylvindoline

Structure
Zoomed Structure
  • Family: Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COc1ccc2c(c1)N(C)[C@@H]1[C@@]32CCN2[C@H]3[C@@]([C@H]([C@]1(O)C(=O)OC)O)(CC)C=CC2
InChI InChI=1S/C23H30N2O5/c1-5-21-9-6-11-25-12-10-22(17(21)25)15-8-7-14(29-3)13-16(15)24(2)18(22)23(28,19(21)26)20(27)30-4/h6-9,13,17-19,26,28H,5,10-12H2,1-4H3/t17-,18+,19+,21+,22+,23-/m0/s1
InChIKey ZDKMPOJNYNVYLA-PEGGBQQISA-N
Formula C23H30N2O5
HBA 7
HBD 2
MW 414.5
Rotatable Bonds 3
TPSA 82.47
LogP 1.07
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 414.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pachypodium lamerei Apocynaceae Plantae 69385

Showing of synonyms

  • Mina S.A, Mohamed S.A, et al. (2020). LC-ESI-MS/MS profiling of alkaloids and antiproliferative activity of Pachypoduim lamerei drake leaves. Natural product research, 2020, 34(9), 1292-1296. [View] [PubMed]
Pubchem: 260534
Kegg Ligand: C01091
Chebi: 18362
Nmrshiftdb2: 60027776
Metabolights: MTBLC18362

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1C234)NC3CCC5C2N(CC4)CC=C5

Level: 0

Mol. Weight: 252.36 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.900
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.720
Plasma Protein Binding
53.54
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.790
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.050
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.540
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.640
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
Toxic
T. Pyriformis
-50.340
Rat (Acute)
3.390
Rat (Chronic Oral)
2.020
Fathead Minnow
4.000
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
444.600
Hydration Free Energy
-3.870
Log(D) at pH=7.4
2.460
Log(P)
1.54
Log S
-2.23
Log(Vapor Pressure)
-9.72
Melting Point
181.68
pKa Acid
6.04
pKa Basic
7.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8870
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.8361
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7984
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7779
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7650
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7603
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7600
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7587
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7565
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7423
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7420
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7416
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7389
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7383
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7328
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7318
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7309
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7301
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7274
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7256
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7250
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7249
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7242
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7218
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7217
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7180
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7173
Cytochrome P450 monooxygenase PikC O87605 PIKC_STRVZ Streptomyces venezuelae 3 0.7146
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7142
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7138
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7128
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7127
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7108
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7103
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7063
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7046
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7001

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