Acriquinoline A - Compound Card

Acriquinoline A

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Acriquinoline A

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone-Quinoline Alkaloid
Canonical Smiles Cc1cc2ccc(=O)n3c2c(c1)C(=O)C3(O)c1c(O)ccc2c1n(C)c1c(c2=O)c(O)cc2c1C=CC(O2)(C)C
InChI InChI=1S/C31H24N2O7/c1-14-11-15-5-8-22(36)33-25(15)18(12-14)29(38)31(33,39)24-19(34)7-6-17-27(24)32(4)26-16-9-10-30(2,3)40-21(16)13-20(35)23(26)28(17)37/h5-13,34-35,39H,1-4H3
InChIKey CFFHHTXFJWCHGE-UHFFFAOYSA-N
Formula C31H24N2O7
HBA 9
HBD 3
MW 536.54
Rotatable Bonds 1
TPSA 130.99
LogP 3.8
Number Rings 7
Number Aromatic Rings 5
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 536.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus reticulata Rutaceae Plantae 85571

Showing of synonyms

  • Fomani M, Ngeufa Happi E, et al. (2016). Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco).. Bioorganic & medicinal chemistry letters,2016, 26(2), 306-309. [View] [PubMed]
Pubchem: 127026993

No compound-protein relationship available.

Structure

SMILES: c1ccc(c2c13)ccc(=O)n2C(C3=O)c4cccc(c5=O)c4[nH]c(c56)c7c(cc6)OCC=C7

Level: 1

Mol. Weight: 536.54 g/mol

Structure

SMILES: C1=CCOc(cc2)c1c(c23)[nH]c4c(c3=O)cccc4

Level: 0

Mol. Weight: 536.54 g/mol

Structure

SMILES: c1ccc(c2c13)ccc(=O)n2CC3=O

Level: 0

Mol. Weight: 536.54 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.5
Plasma Protein Binding
66.1
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
4.13
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.38
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.57
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
Toxic
T. Pyriformis
-5364.13
Rat (Acute)
2.56
Rat (Chronic Oral)
3.03
Fathead Minnow
18.59
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
555.1
Hydration Free Energy
-3.11
Log(D) at pH=7.4
2.47
Log(P)
3.18
Log S
-4.97
Log(Vapor Pressure)
-8.64
Melting Point
369.27
pKa Acid
9.86
pKa Basic
5.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8694
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8547
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8338
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8265
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8051
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7928
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7909
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7897
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7839
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7734
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7698
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7664
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7559
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7517
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7499
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7483
Enoyl-acyl carrier reductase C6KSZ2 C6KSZ2_PLAF7 Plasmodium falciparum 4 0.7459
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7407
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7379
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7354
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7333
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7326
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7198
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7080
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7069
Albumin P14639 ALBU_SHEEP Ovis aries 3 0.7057
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7018

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