Laurentiquinone A - Compound Card

Laurentiquinone A

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Laurentiquinone A

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COC1CC(=O)C(C(C1=O)OC)C1COc2c(C1)ccc(c2OC)O
InChI InChI=1S/C18H22O7/c1-22-13-7-12(20)14(18(24-3)15(13)21)10-6-9-4-5-11(19)17(23-2)16(9)25-8-10/h4-5,10,13-14,18-19H,6-8H2,1-3H3
InChIKey YBMCFJXGQFZICJ-UHFFFAOYSA-N
Formula C18H22O7
HBA 7
HBD 1
MW 350.37
Rotatable Bonds 4
TPSA 91.29
LogP 1.14
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 350.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Vismia guineensis Guttiferae Plantae 999599

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]
Pubchem: 15895792

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OCC(C2)C(C3=O)CC(=O)CC3

Level: 1

Mol. Weight: 350.37 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 350.37 g/mol

Structure

SMILES: O=C1CCC(=O)CC1

Level: 0

Mol. Weight: 350.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.790
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.780
Plasma Protein Binding
9.32
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
10.200
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.490
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.500
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.060
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.620
Rat (Acute)
2.640
Rat (Chronic Oral)
2.160
Fathead Minnow
4.310
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
392.550
Hydration Free Energy
-9.640
Log(D) at pH=7.4
1.430
Log(P)
0.73
Log S
-2.38
Log(Vapor Pressure)
-6.81
Melting Point
141.6
pKa Acid
6.29
pKa Basic
2.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9445
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9394
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.9264
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9258
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9015
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8969
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8967
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8922
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8892
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8876
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8852
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8823
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8812
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8795
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8781
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8762
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8700
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8638
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8629
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8590
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8580
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8578
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8498
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8469
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8430
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8398
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8330
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8301
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8240
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8238
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8215
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8164
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8147
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8146
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8137
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8130
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8105
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8071
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8040
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8039
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8032
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8021
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7957
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7923
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7922
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7921
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7907
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7886
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7844
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7811
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7782
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7734
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7694
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7681
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7664
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7653
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7645
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7638
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7617
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7581
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7551
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7532
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7525
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7510
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7501
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7452
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7451
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7451
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7431
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 4 0.7422
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7412
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7405
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7388
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7383
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7377
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7367
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7363
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7362
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7357
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7344
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7321
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7287
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7280
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7268
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7266
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7264
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7259
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7259
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7258
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7252
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7249
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7248
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7246
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7240
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7233
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7231
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7226
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7219
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7213
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7207
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7205
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7203
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7200
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7189
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7174
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7172
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7157
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7149
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7136
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7127
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7126
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7126
Bifunctional protein GAL10 P04397 GAL10_YEAST Saccharomyces cerevisiae 4 0.7124
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7116
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7116
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7111
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7109
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7106
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7099
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7097
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7085
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7081
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7079
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7068
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7057
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7047
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7045
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7040
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7031
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7031
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7026
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7023
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7022
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7022
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7017
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7014
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7011
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7009
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7001

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