2-hydroxymethyl-3-O-prenylanthraquinone - Compound Card

2-hydroxymethyl-3-O-prenylanthraquinone

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2-hydroxymethyl-3-O-prenylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles OCc1cc2C(=O)c3ccccc3C(=O)c2cc1OCC=C(C)C
InChI InChI=1S/C20H18O4/c1-12(2)7-8-24-18-10-17-16(9-13(18)11-21)19(22)14-5-3-4-6-15(14)20(17)23/h3-7,9-10,21H,8,11H2,1-2H3
InChIKey CEHOEMUCIIRQDR-UHFFFAOYSA-N
Formula C20H18O4
HBA 4
HBD 1
MW 322.36
Rotatable Bonds 4
TPSA 63.6
LogP 3.3
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 322.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas schimperi Rubiaceae Plantae 25384

Showing of synonyms

  • Goffin E, Ziemons E, et al. (2002). In vitro antiplasmodial activity of Tithonia diversifolia and identification of its main active constituent: tagitinin C.. Planta medica,2002, 68(6), 543-545. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 322.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.38
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
62.52
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
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
4.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.56
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.46
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
2.43
Rat (Acute)
2.49
Rat (Chronic Oral)
2.2
Fathead Minnow
4.94
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
436.7
Hydration Free Energy
-8.69
Log(D) at pH=7.4
2.19
Log(P)
4.48
Log S
-5.48
Log(Vapor Pressure)
-7.99
Melting Point
156.27
pKa Acid
8.33
pKa Basic
4.93
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 0.9357
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.9230
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8927
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8714
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8450
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8406
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8305
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8262
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8158
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8092
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8090
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8079
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8065
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7990
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7955
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7907
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7890
Aclacinomycin 10-hydroxylase RdmB Q54527 RDMB_STREF Streptomyces purpurascens 3 0.7867
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7828
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7805
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7799
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7775
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7678
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7676
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7655
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7634
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7622
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7621
Peroxisome proliferator-activated receptor delta Q03181 PPARD_HUMAN Homo sapiens 4 0.7619
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7582
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7578
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7569
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7543
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7540
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7534
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7534
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7532
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7523
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7509
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7503
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7494
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7490
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7460
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7460
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7450
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7439
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7423
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7416
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7406
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7391
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7383
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7364
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7360
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7356
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7351
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7349
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7320
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7317
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7314
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7308
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7298
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7275
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7255
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7238
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7222
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7209
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7208
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7206
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7196
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7192
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7167
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7158
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7126
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7117
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7107
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7080
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7073
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7051
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7039
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7034
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7034
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7027
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7000

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