17-O-acetylnortetraphyllicine - Compound Card

17-O-acetylnortetraphyllicine

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17-O-acetylnortetraphyllicine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles C/C=C\1/CN2C3C4C1CC2C1C(C4OC(=O)C)(C3)c2c(N1)cccc2
InChI InChI=1S/C21H24N2O2/c1-3-12-10-23-16-8-13(12)18-17(23)9-21(20(18)25-11(2)24)14-6-4-5-7-15(14)22-19(16)21/h3-7,13,16-20,22H,8-10H2,1-2H3/b12-3-
InChIKey FKJUTPWOUBGWAP-BASWHVEKSA-N
Formula C21H24N2O2
HBA 4
HBD 1
MW 336.44
Rotatable Bonds 1
TPSA 41.57
LogP 2.7
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 336.18
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]

No compound-protein relationship available.

Structure

SMILES: C=C(C1)C(C2)C(C3)C(C4)N1C2C5Nc(c6C345)cccc6

Level: 0

Mol. Weight: 336.44 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.05
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
33.94
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
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.49
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-0.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.13
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.27
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
-2.85
Rat (Acute)
4.39
Rat (Chronic Oral)
1.64
Fathead Minnow
4.86
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
418.59
Hydration Free Energy
-1.23
Log(D) at pH=7.4
1.78
Log(P)
2.81
Log S
-3.44
Log(Vapor Pressure)
-8.06
Melting Point
197.43
pKa Acid
7.81
pKa Basic
7.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cyclomaltodextrin glucanotransferase P05618 CDGT_BACS0 Bacillus sp 3 0.8624
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8583
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7746
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7469
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7340
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7290
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7134
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7121
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7094
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7072
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7055

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