Zenkequinone B - Compound Card

Zenkequinone B

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Zenkequinone B

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles c1ccc2c(c1)C(=O)c1c(C2=O)ccc2c1CC(CC2)(C)O
InChI InChI=1S/C19H16O3/c1-19(22)9-8-11-6-7-14-16(15(11)10-19)18(21)13-5-3-2-4-12(13)17(14)20/h2-7,22H,8-10H2,1H3
InChIKey SIJURHHKUFYDRK-UHFFFAOYSA-N
Formula C19H16O3
HBA 3
HBD 1
MW 292.33
Rotatable Bonds 0
TPSA 54.37
LogP 2.7
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 292.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Stereospermum zenkeri Bignoniaceae Plantae 260324

Showing of synonyms

  • Lenta BN, Weniger B, et al. (2007). Anthraquinones from the stem bark of Stereospermum zenkeri with antimicrobial activity.. Phytochemistry,2007, 68(11), 1595-1599. [View] [PubMed]
Pubchem: 16741799

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc4c3CCCC4

Level: 0

Mol. Weight: 292.33 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.24
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.0
Plasma Protein Binding
61.21
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.26
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.52
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.08
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.85
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
3.68
Rat (Acute)
2.71
Rat (Chronic Oral)
1.91
Fathead Minnow
4.5
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
419.6
Hydration Free Energy
-8.19
Log(D) at pH=7.4
2.04
Log(P)
3.83
Log S
-4.84
Log(Vapor Pressure)
-8.2
Melting Point
227.54
pKa Acid
8.11
pKa Basic
4.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9493
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9173
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8850
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8612
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.8567
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8459
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8408
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8154
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8095
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8063
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7965
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7892
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7883
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7873
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7860
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7846
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7831
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7809
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7803
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7800
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7774
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7753
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7751
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7659
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7650
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7633
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7609
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7608
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7590
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7578
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7567
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7548
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7544
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 3 0.7497
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7470
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7466
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7446
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7443
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7420
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7414
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7406
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7383
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7368
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7340
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7299
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7257
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7251
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7230
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7226
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7201
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7197
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7191
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7191
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7133
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7122
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7119
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7114
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7110
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7099
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7079
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7046
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7025
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7018
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7018

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