Sarpagine - Compound Card

Sarpagine

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Sarpagine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles OC[C@H]1[C@@H]2Cc3c([C@H]4N2C/C(=C/C)/[C@@H]1C4)[nH]c1c3cc(O)cc1
InChI InChI=1S/C19H22N2O2/c1-2-10-8-21-17-7-14-13-5-11(23)3-4-16(13)20-19(14)18(21)6-12(10)15(17)9-22/h2-5,12,15,17-18,20,22-23H,6-9H2,1H3/b10-2-/t12-,15+,17-,18-/m0/s1
InChIKey VTVQHYQGTTVKDE-CCUKBNNFSA-N
Formula C19H22N2O2
HBA 3
HBD 3
MW 310.4
Rotatable Bonds 1
TPSA 59.49
LogP 2.73
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 310.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Rauvolfia caffra Apocynaceae Plantae 947877

Showing of synonyms

  • Bitombo AN, Zintchem AAA, et al. (2022). Antimicrobial and cytotoxic activities of indole alkaloids and other constituents from the stem barks of Rauvolfia caffra Sond (Apocynaceae). Natural product research,2022, 36(6), 1467-1475. [View] [PubMed]
Pubchem: 12314884
Chebi: 9036
Nmrshiftdb2: 60061978
Metabolights: MTBLC9036
CPRiL: 455075
Structure

SMILES: C=C(C1)C(C2)CC(C3)N1C2c(c3c45)[nH]c4cccc5

Level: 0

Mol. Weight: 310.4 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.340
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.140
Plasma Protein Binding
58.42
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
16.150
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.410
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.830
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.450
Micronucleos
Toxic
NR-AhR
Toxic
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
-1.090
Rat (Acute)
2.690
Rat (Chronic Oral)
2.420
Fathead Minnow
4.100
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
437.210
Hydration Free Energy
-6.920
Log(D) at pH=7.4
1.650
Log(P)
2.1
Log S
-3.29
Log(Vapor Pressure)
-9.86
Melting Point
285.86
pKa Acid
8.44
pKa Basic
8.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9545
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9038
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8702
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8619
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.8606
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8542
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8518
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7896
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7838
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7671
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7308
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7226
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7199
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7164
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7104
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7079
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7066
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7053
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7047
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7022
Nicotinamide phosphoribosyltransferase Q80Z29 NAMPT_RAT Rattus norvegicus 3 0.7018
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7006

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