Laurenquinone A - Compound Card

Laurenquinone A

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Laurenquinone A

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Anthraquinone
    • Subclass: Prenylated Anthraquinone
Canonical Smiles COC(=O)c1c(C)cc2c(c1O)C(=O)c1c(C2=O)cc(c(c1O)CC=C(C)C)O
InChI InChI=1S/C22H20O7/c1-9(2)5-6-11-14(23)8-13-16(19(11)25)21(27)17-12(18(13)24)7-10(3)15(20(17)26)22(28)29-4/h5,7-8,23,25-26H,6H2,1-4H3
InChIKey VHXGADCMKFUNJN-UHFFFAOYSA-N
Formula C22H20O7
HBA 7
HBD 3
MW 396.4
Rotatable Bonds 3
TPSA 121.13
LogP 3.18
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 396.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Vismia laurentii Guttiferae Plantae 2704497

Showing of synonyms

  • Wabo HK, Kouam SF, et al. (2007). Prenylated anthraquinones and other constituents from the seeds of Vismia laurentii.. Chemical & pharmaceutical bulletin,2007, 55(11), 1640-1642. [View] [PubMed]
Pubchem: 23661635
Nmrshiftdb2: 60076365

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 396.4 g/mol

Algicidal

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.760
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.040
Plasma Protein Binding
57.84
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.170
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.700
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.850
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-5.410
Rat (Acute)
2.550
Rat (Chronic Oral)
3.780
Fathead Minnow
4.970
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
489.360
Hydration Free Energy
-8.660
Log(D) at pH=7.4
3.420
Log(P)
5.95
Log S
-7.49
Log(Vapor Pressure)
-8.32
Melting Point
199.21
pKa Acid
5.85
pKa Basic
5.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9484
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9275
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8834
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8780
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8591
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8568
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8534
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8309
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8208
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8197
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7962
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7917
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7864
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7781
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7736
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7717
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7557
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7504
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7454
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7438
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7421
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7403
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7388
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7358
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7345
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7338
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7327
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7253
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7210
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7208
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7207
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7184
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7159
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7104
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7066
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7039
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7029
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7024
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7022

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