Lochnerine - Compound Card

Lochnerine

Select a section from the left sidebar

Lochnerine

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(OC)cc1
InChI InChI=1S/C20H24N2O2/c1-3-11-9-22-18-8-15-14-6-12(24-2)4-5-17(14)21-20(15)19(22)7-13(11)16(18)10-23/h3-6,13,16,18-19,21,23H,7-10H2,1-2H3/b11-3-/t13-,16+,18-,19-/m0/s1
InChIKey YTIVOMMYBBBYFH-BOPWJTLDSA-N
Formula C20H24N2O2
HBA 3
HBD 2
MW 324.42
Rotatable Bonds 2
TPSA 48.49
LogP 3.03
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 324.18
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: 6436184
Nmrshiftdb2: 60062267
Bindingdb: 50480330

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 324.42 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.120
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.360
Plasma Protein Binding
57.79
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.650
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.070
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.000
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.380
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
-2.660
Rat (Acute)
2.770
Rat (Chronic Oral)
2.110
Fathead Minnow
4.230
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
442.350
Hydration Free Energy
-4.990
Log(D) at pH=7.4
2.180
Log(P)
2.81
Log S
-3.46
Log(Vapor Pressure)
-9.17
Melting Point
229.0
pKa Acid
10.36
pKa Basic
8.43
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 0.9719
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9248
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8969
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8951
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8055
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8042
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7868
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7426
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7399
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7388
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7387
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7352
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7338
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7320
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7299
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7271
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7254
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7238
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7218
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7176
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7164
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7130
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7122
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7117
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7104
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7098
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7037
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7032
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7010
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7002

Download SDF