Laurentiquinone B - Compound Card

Laurentiquinone B

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Laurentiquinone B

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COC(=O)c1c(C)cc2c(c1O)C(=O)c1c(C2=O)cc2c(c1O)C=CC(O2)(C)C
InChI InChI=1S/C22H18O7/c1-9-7-11-16(19(25)14(9)21(27)28-4)20(26)15-12(17(11)23)8-13-10(18(15)24)5-6-22(2,3)29-13/h5-8,24-25H,1-4H3
InChIKey YELMGJGNPKYOJB-UHFFFAOYSA-N
Formula C22H18O7
HBA 7
HBD 2
MW 394.38
Rotatable Bonds 1
TPSA 110.13
LogP 3.15
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 394.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Vismia guineensis Guttiferae Plantae 999599
2 Vismia laurentii Guttiferae Plantae 2704497

Showing of synonyms

  • Tala M, Talontsi F, et al. (2013). Anthraquinones and triterpenoids from seeds of Vismia guineensis. Biochemical Systematics and Ecology, 2013, 50, 310-312. [View]
  • 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: 24750385
Nmrshiftdb2: 60076364

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c2)c1cc(c23)C(=O)c4c(C3=O)cccc4

Level: 0

Mol. Weight: 394.38 g/mol

Algicidal

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
50.99
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
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.110
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.030
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
6.120
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-8.070
Rat (Acute)
2.830
Rat (Chronic Oral)
3.220
Fathead Minnow
4.850
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
483.080
Hydration Free Energy
-7.810
Log(D) at pH=7.4
3.750
Log(P)
5.56
Log S
-7.19
Log(Vapor Pressure)
-8.59
Melting Point
217.58
pKa Acid
5.96
pKa Basic
4.5
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 0.9468
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8985
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8934
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8819
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8649
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8553
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8112
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8004
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7983
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7866
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7517
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7441
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7367
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7354
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7346
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7303
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7298
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7291
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7281
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7279
Squalene--hopene cyclase P33247 SQHC_ALIAD Alicyclobacillus acidocaldarius subsp. acidocaldarius 4 0.7136
Squalene--hopene cyclase P33247 SQHC_ALIAD Alicyclobacillus acidocaldarius subsp. acidocaldarius 5 0.7129
Squalene--hopene cyclase P33247 SQHC_ALIAD Alicyclobacillus acidocaldarius subsp. acidocaldarius 4 0.7121
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7108
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7080
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7046
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7042
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7034
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7023

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