2,3-dihydroxypropyl-1,6,8-trihydroxy-3-methyl-9,10-dioxoanthracen-2-carboxylate - Compound Card

2,3-dihydroxypropyl-1,6,8-trihydroxy-3-methyl-9,10-dioxoanthracen-2-carboxylate

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2,3-dihydroxypropyl-1,6,8-trihydroxy-3-methyl-9,10-dioxoanthracen-2-carboxylate

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Anthracene
Canonical Smiles OCC(COC(=O)c1c(C)cc2c(c1O)C(=O)c1c(C2=O)cc(cc1O)O)O
InChI InChI=1S/C19H16O9/c1-7-2-10-15(17(25)13(7)19(27)28-6-9(22)5-20)18(26)14-11(16(10)24)3-8(21)4-12(14)23/h2-4,9,20-23,25H,5-6H2,1H3
InChIKey WRGYUPQTNNDKAT-UHFFFAOYSA-N
Formula C19H16O9
HBA 9
HBD 5
MW 388.33
Rotatable Bonds 4
TPSA 161.59
LogP 0.4
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 388.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus wentii Trichocomaceae Fungi 5066

Showing of synonyms

  • Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]
Pubchem: 85180730

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 388.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.7
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.970
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.840
Plasma Protein Binding
48.61
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.210
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.940
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.640
Micronucleos
Toxic
NR-AhR
Safe
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
-2.230
Rat (Acute)
2.540
Rat (Chronic Oral)
3.710
Fathead Minnow
4.170
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
532.730
Hydration Free Energy
-11.590
Log(D) at pH=7.4
1.270
Log(P)
2.48
Log S
-4.33
Log(Vapor Pressure)
-9.04
Melting Point
201.76
pKa Acid
5.35
pKa Basic
4.15
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 0.9479
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9245
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8999
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8994
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8976
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8944
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8928
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8815
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8775
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8611
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8538
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8511
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8504
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8389
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8383
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8329
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8252
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8215
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8197
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8135
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8103
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8102
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8083
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7988
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7978
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7965
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7951
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7935
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7855
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7815
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7803
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7795
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7782
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7779
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7776
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7760
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7755
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7716
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7698
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7655
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7652
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7644
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7639
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7631
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7601
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7575
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7566
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7540
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7532
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7507
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7501
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7462
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7455
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7431
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7428
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7414
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 3 0.7350
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7323
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7322
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7322
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7319
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7313
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7313
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7301
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 3 0.7293
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7262
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7238
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7221
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7205
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7185
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7171
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7110
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7107
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7098
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7079
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7070
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7053
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7045
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7019
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7016
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7016
Dimethylsulfonioproprionate demethylase DmdA Q4FP21 DMDA_PELUB Pelagibacter ubique 4 0.7002

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