Grandiquinone A - Compound Card

Grandiquinone A

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Grandiquinone A

Structure
Zoomed Structure
  • Family: Plantae - Verbenaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles CC(=O)Oc1cc2C(=O)c3cccc(c3C(=O)c2cc1C)O
InChI InChI=1S/C17H12O5/c1-8-6-11-12(7-14(8)22-9(2)18)16(20)10-4-3-5-13(19)15(10)17(11)21/h3-7,19H,1-2H3
InChIKey ZRTWZYGPGCNMLX-UHFFFAOYSA-N
Formula C17H12O5
HBA 5
HBD 1
MW 296.28
Rotatable Bonds 1
TPSA 80.67
LogP 2.4
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 296.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tectona grandis Verbenaceae Plantae 41396

Showing of synonyms

  • Kopa T, Tchinda A, et al. (2014). Antiplasmodial anthraquinones and hemisynthetic derivatives from the leaves of Tectona grandis (Verbenaceae). Phytochemistry Letters, 2014, 8, 41-45. [View]
Pubchem: 102236728

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 296.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.09
Plasma Protein Binding
58.65
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.39
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.47
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
4.45
Rat (Acute)
2.48
Rat (Chronic Oral)
2.58
Fathead Minnow
4.69
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
425.63
Hydration Free Energy
-8.75
Log(D) at pH=7.4
2.44
Log(P)
3.7
Log S
-5.89
Log(Vapor Pressure)
-7.54
Melting Point
198.07
pKa Acid
6.76
pKa Basic
4.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9504
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9489
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9485
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9372
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9090
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8920
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8877
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8828
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8780
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8777
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8769
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.8513
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8499
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8385
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8188
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8114
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8075
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8068
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8034
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8028
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8016
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7983
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7981
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7977
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7975
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7925
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7894
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7890
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7832
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7792
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7742
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7717
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7690
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7681
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7648
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7642
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7624
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7617
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7617
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7598
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7590
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7590
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7581
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7579
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7576
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7562
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7542
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7541
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7539
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7472
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7427
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7408
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7403
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7396
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7391
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7383
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7372
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7358
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7349
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7344
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7327
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7308
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7305
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7300
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7297
Bifunctional dihydrofolate reductase-thymidylate synthase Q27783 DRTS_TRYBB Trypanosoma brucei brucei 4 0.7247
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7246
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7240
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7238
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7227
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7208
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7189
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7188
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7168
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7159
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7158
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7133
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7131
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7120
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7108
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7091
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7086
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7064
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7051
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7030
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7023
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7021
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7020
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 4 0.7018
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7017
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7007

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