3-(1′,1′-dimethylallyl)-3-(3′′,3′′-dimethylallyl)-1,2,3,4-tetrahydro-2,4-quinoldione - Compound Card

3-(1′,1′-dimethylallyl)-3-(3′′,3′′-dimethylallyl)-1,2,3,4-tetrahydro-2,4-quinoldione

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3-(1′,1′-dimethylallyl)-3-(3′′,3′′-dimethylallyl)-1,2,3,4-tetrahydro-2,4-quinoldione

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Quinoline Alkaloid
Canonical Smiles C=CC(C1(CC=C(C)C)C(=O)Nc2c(C1=O)cccc2)(C)C
InChI InChI=1S/C19H23NO2/c1-6-18(4,5)19(12-11-13(2)3)16(21)14-9-7-8-10-15(14)20-17(19)22/h6-11H,1,12H2,2-5H3,(H,20,22)
InChIKey LAXFAGHIJVQGNK-UHFFFAOYSA-N
Formula C19H23NO2
HBA 2
HBD 1
MW 297.4
Rotatable Bonds 4
TPSA 46.17
LogP 4.38
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.37
Exact Mass 297.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Haplophyllum tuberculatum Rutaceae Plantae 452784

Showing of synonyms

  • M. Sheriha G, Abouamer K, et al. (1987). Quinoline alkaloids and cytotoxic lignans from Haplophyllum tuberculatum. Phytochemistry, 1987, 26(12), 3339-3341. [View]
Pubchem: 461150
Chebi: 65535
Nmrshiftdb2: 20180072
Metabolights: MTBLC65535
Bindingdb: 50478415

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)NC(=O)CC2=O

Level: 0

Mol. Weight: 297.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.38
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.31
Plasma Protein Binding
41.22
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
4.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.34
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.42
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.57
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
3.1
Rat (Acute)
2.18
Rat (Chronic Oral)
1.86
Fathead Minnow
4.53
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
363.63
Hydration Free Energy
-9.21
Log(D) at pH=7.4
3.08
Log(P)
4.94
Log S
-4.94
Log(Vapor Pressure)
-6.38
Melting Point
100.24
pKa Acid
8.56
pKa Basic
4.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9335
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.9034
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8940
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8688
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8590
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8071
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7998
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7979
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7843
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7785
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7762
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7759
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7688
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7635
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7610
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7601
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7591
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7548
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7507
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7496
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7491
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7436
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7429
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7428
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7399
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7394
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7381
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7373
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7364
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7343
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7339
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7320
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7315
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7292
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7289
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7289
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7260
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7220
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7218
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7215
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7201
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7180
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7174
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7165
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7164
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7159
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7146
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7110
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7076
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7064
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7062
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7051
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7050
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7038
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7012
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7008

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