(-)-apparicin-21-one - Compound Card

(-)-apparicin-21-one

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(-)-apparicin-21-one

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles C/C=C\1/C(=O)N2CC[C@@H]1C(=C)c1c(C2)c2c([nH]1)cccc2
InChI InChI=1S/C18H18N2O/c1-3-12-13-8-9-20(18(12)21)10-15-14-6-4-5-7-16(14)19-17(15)11(13)2/h3-7,13,19H,2,8-10H2,1H3/b12-3+/t13-/m1/s1
InChIKey NFNIHHIOHAKFCI-ACDNVWSCSA-N
Formula C18H18N2O
HBA 1
HBD 1
MW 278.35
Rotatable Bonds 0
TPSA 36.1
LogP 3.49
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 278.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tabernaemontana contorta Apocynaceae Plantae 761060

Showing of synonyms

  • Foudjo Melacheu G, Mfotie Njoya E, et al. (2019). Two new indole alkaloids from Tabernaemontana contorta Stapf. Phytochemistry Letters, 2019, 30, 116-119. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CN(C2)C(=O)C(=C)C1C(=C)c(c2c34)[nH]c3cccc4

Level: 0

Mol. Weight: 278.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.95
Plasma Protein Binding
60.32
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.52
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.58
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.08
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.48
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
2.48
Rat (Acute)
2.58
Rat (Chronic Oral)
2.5
Fathead Minnow
4.57
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
415.51
Hydration Free Energy
-8.66
Log(D) at pH=7.4
2.76
Log(P)
3.22
Log S
-4.38
Log(Vapor Pressure)
-9.05
Melting Point
240.58
pKa Acid
11.13
pKa Basic
6.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8946
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8920
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8631
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8609
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8335
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8325
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8250
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8170
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8152
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7936
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7930
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7879
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7855
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7819
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7782
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7757
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.7742
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7639
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7618
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7603
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7583
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7540
DNA double-strand break repair protein Mre11 Q9X1X0 Q9X1X0_THEMA Thermotoga maritima MSB8 3 0.7532
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7530
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7529
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7529
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7439
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7421
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7389
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7341
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7312
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7309
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7306
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7304
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7292
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7259
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7259
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7257
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7244
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7235
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 2 0.7221
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7181
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7156
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7142
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7140
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7117
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7106
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7089
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7052
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7051
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7042
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7042
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7031
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.7030
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7022
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7017

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