Vismiaquinone B - Compound Card

Vismiaquinone B

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Vismiaquinone B

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc2c(c(c1CC(=O)C(C)C)O)C(=O)c1c(C2=O)cc(cc1O)C
InChI InChI=1S/C21H20O6/c1-9(2)14(22)7-11-16(27-4)8-13-18(20(11)25)21(26)17-12(19(13)24)5-10(3)6-15(17)23/h5-6,8-9,23,25H,7H2,1-4H3
InChIKey POZKRJDVQGSFPR-UHFFFAOYSA-N
Formula C21H20O6
HBA 6
HBD 2
MW 368.39
Rotatable Bonds 4
TPSA 100.9
LogP 2.96
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 368.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Vismia laurentii Clusiaceae Plantae 2704497
2 Vismia guineensis Guttiferae Plantae 999599
3 Harungana madagascariensis Hypericaceae Plantae 198768

Showing of synonyms

  • Kouam SF, Khan SN, et al. (2006). Alpha-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis.. Journal of natural products,2006, 69(2), 229-233. [View] [PubMed]
  • Tala M, Talontsi F, et al. (2013). Anthraquinones and triterpenoids from seeds of Vismia guineensis. Biochemical Systematics and Ecology, 2013, 50, 310-312. [View]
  • Kemegne GA, Mkounga P, et al. (2017). Antimicrobial structure activity relationship of five anthraquinones of emodine type isolated from Vismia laurentii.. BMC microbiology,2017, 17(1), 41. [View] [PubMed]
Pubchem: 14729072
Nmrshiftdb2: 60025849

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 368.39 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.740
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.090
Plasma Protein Binding
69.49
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.270
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.680
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.890
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.210
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
0.660
Rat (Acute)
2.590
Rat (Chronic Oral)
3.110
Fathead Minnow
4.890
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
462.290
Hydration Free Energy
-9.270
Log(D) at pH=7.4
2.760
Log(P)
4.25
Log S
-6.97
Log(Vapor Pressure)
-8.13
Melting Point
184.12
pKa Acid
6.45
pKa Basic
4.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9586
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9205
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8938
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8859
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8799
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8608
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8602
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8601
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8595
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8593
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8541
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8518
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8454
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8443
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8391
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8302
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8286
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8169
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8075
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8070
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8022
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7901
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7851
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7815
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7807
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7795
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7683
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7676
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7628
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7592
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7590
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7583
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7577
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7571
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7545
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7542
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7540
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7537
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7534
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7484
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7420
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7408
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7399
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7373
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7359
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7347
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7315
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7284
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7259
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7255
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7242
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7225
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7213
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7209
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7197
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7195
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7183
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7156
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7143
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7135
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7124
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7108
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7107
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7087
Bifunctional F420 biosynthesis protein FbiB P9WP79 FBIB_MYCTU Mycobacterium tuberculosis 5 0.7039
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7026
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7020
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7019
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7014
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7012
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7006
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7004

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