Melinonine A - Compound Card

Melinonine A

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Melinonine A

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COC(=O)C1=CO[C@H]([C@@H]2[C@@H]1C[C@H]1c3[nH]c4c(c3CC[N+]1(C2)C)cccc4)C
InChI InChI=1S/C22H27N2O3/c1-13-17-11-24(2)9-8-15-14-6-4-5-7-19(14)23-21(15)20(24)10-16(17)18(12-27-13)22(25)26-3/h4-7,12-13,16-17,20,23H,8-11H2,1-3H3/q+1/t13-,16-,17+,20-,24?/m0/s1
InChIKey PGWDPYAZSCNZHS-OXIZCCONSA-N
Formula C22H27N2O3+
HBA 3
HBD 1
MW 367.47
Rotatable Bonds 1
TPSA 51.32
LogP 3.32
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 1
Fraction CSP3 0.5
Exact Mass 367.2
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: 20054968
Nmrshiftdb2: 60063047

No compound-protein relationship available.

Structure

SMILES: c1cccc2[nH]c(c3c12)C4[NH+](CC3)CC5C(C4)C=COC5

Level: 0

Mol. Weight: 367.47 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.93
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.760
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.760
Plasma Protein Binding
49.48
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
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
11.600
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.770
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.770
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.770
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
-12.730
Rat (Acute)
3.050
Rat (Chronic Oral)
1.540
Fathead Minnow
4.080
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
429.200
Hydration Free Energy
-5.540
Log(D) at pH=7.4
2.480
Log(P)
0.25
Log S
-1.07
Log(Vapor Pressure)
-9.46
Melting Point
231.36
pKa Acid
7.84
pKa Basic
6.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8454
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.8224
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7618
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7555
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7397
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7274
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7227
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7225
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7208
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7192
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7078
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7076

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