1,5-dihroxy-3-hydroxymethylanthraquinone - Compound Card

1,5-dihroxy-3-hydroxymethylanthraquinone

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1,5-dihroxy-3-hydroxymethylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles OCc1cc(O)c2c(c1)C(=O)c1c(C2=O)cccc1O
InChI InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)14(19)8-2-1-3-10(17)12(8)15(9)20/h1-5,16-18H,6H2
InChIKey WPKQIGIVDUYIBC-UHFFFAOYSA-N
Formula C15H10O5
HBA 5
HBD 3
MW 270.24
Rotatable Bonds 1
TPSA 94.83
LogP 1.37
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 270.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe excelsa Asphodelaceae Plantae 992640

Showing of synonyms

  • Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
Pubchem: 617886
Nmrshiftdb2: 60076477

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 270.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
57.05
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
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.96
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.97
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
3.7
Rat (Acute)
2.49
Rat (Chronic Oral)
3.21
Fathead Minnow
4.1
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
428.26
Hydration Free Energy
-10.65
Log(D) at pH=7.4
1.7
Log(P)
2.71
Log S
-4.72
Log(Vapor Pressure)
-8.42
Melting Point
202.25
pKa Acid
6.23
pKa Basic
5.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.9340
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.9340
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8945
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8945
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8889
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8889
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8790
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8790
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8292
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8292
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8272
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8272
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8253
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8253
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.8103
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.8103
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8066
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8066
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8004
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8004
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7943
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7943
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7891
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7891
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7823
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7823
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7798
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7798
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7789
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7789
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7757
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7757
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7701
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7701
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7691
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7691
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7688
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7688
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7677
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7677
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7607
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7607
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7586
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7586
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 4 0.7527
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 4 0.7527
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7505
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7505
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7502
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7502
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7489
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7489
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7471
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7471
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7466
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7466
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7420
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7420
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7397
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7397
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7365
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7365
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7347
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7347
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7283
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7283
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7216
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7216
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7216
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7216
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7172
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7172
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7171
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7171
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7162
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7162
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7150
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7150
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7105
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7105
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7082
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7082
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7079
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7079
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7066
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7066
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7050
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7050
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7035
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7035
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 4 0.7033
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 4 0.7033
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7007
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7007
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7003
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7003

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