(4R,5R,6R)-4,5-dihydroxy-6-(6'-methylsalicyloxy)-2-methyl-2-cyclohexen-1-one - Compound Card

(4R,5R,6R)-4,5-dihydroxy-6-(6'-methylsalicyloxy)-2-methyl-2-cyclohexen-1-one

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(4R,5R,6R)-4,5-dihydroxy-6-(6'-methylsalicyloxy)-2-methyl-2-cyclohexen-1-one

Structure
Zoomed Structure
  • Family: Fungi - Incertae sedis
  • Kingdom: Fungi
  • Class: Ketone
Canonical Smiles O[C@@H]1C=C(C)C(=O)[C@@H]([C@@H]1O)OCc1c(C)cccc1O
InChI InChI=1S/C15H18O5/c1-8-4-3-5-11(16)10(8)7-20-15-13(18)9(2)6-12(17)14(15)19/h3-6,12,14-17,19H,7H2,1-2H3/t12-,14-,15+/m1/s1
InChIKey CYPPRAKLFXLYKK-YUELXQCFSA-N
Formula C15H18O5
HBA 5
HBD 3
MW 278.3
Rotatable Bonds 3
TPSA 86.99
LogP 0.84
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 278.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Geosmithia langdonii Incertae sedis Fungi 240214

Showing of synonyms

  • Malak LG, Ibrahim MA, et al. (2014). Antileishmanial metabolites from geosmithia langdonii. Journal of Natural Products,2014,77(9),1987-1991. [View] [PubMed]
Pubchem: 162817181
Nmrshiftdb2: 60033067

No compound-protein relationship available.

Structure

SMILES: c1ccccc1COC2CCC=CC2=O

Level: 1

Mol. Weight: 278.3 g/mol

Structure

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 278.3 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 278.3 g/mol

Anti-leishmanial

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.37
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
49.76
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-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
9.08
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.62
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.86
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.65
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
-0.73
Rat (Acute)
2.29
Rat (Chronic Oral)
2.75
Fathead Minnow
3.99
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
355.12
Hydration Free Energy
-12.64
Log(D) at pH=7.4
1.29
Log(P)
1.06
Log S
-1.9
Log(Vapor Pressure)
-7.79
Melting Point
153.78
pKa Acid
6.62
pKa Basic
4.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8927
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8927
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 4 0.8797
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 4 0.8797
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8745
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8745
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8693
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8693
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8456
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8456
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8415
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8415
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8321
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8321
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 3 0.8252
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 3 0.8252
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8116
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8116
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8107
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8107
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8003
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8003
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7903
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7903
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7766
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7766
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 3 0.7765
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 3 0.7765
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7695
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7695
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7689
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7689
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7640
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7640
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7639
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7639
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7606
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7606
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7598
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7598
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7591
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7591
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7571
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7571
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7568
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7568
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7504
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7504
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7454
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7454
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7446
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7446
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7433
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7433
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7430
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7430
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7393
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7393
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7378
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7378
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 4 0.7372
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 4 0.7372
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7346
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7346
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7341
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7341
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7326
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7326
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7319
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7319
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7302
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7302
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7291
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7291
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7274
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7274
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7274
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7274
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7243
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7243
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7216
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7216
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7190
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7190
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7190
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7190
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7177
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7177
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7172
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7172
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 4 0.7167
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 4 0.7167
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7165
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7165
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7159
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7159
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7132
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7132
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7127
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7127
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7091
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7091
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7082
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7082
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7065
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7065
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7062
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7062
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7037
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7037
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7033
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7033
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7032
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7032
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7013
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7013
cAMP-dependent protein kinase regulatory subunit P07278 KAPR_YEAST Saccharomyces cerevisiae 3 0.7011
cAMP-dependent protein kinase regulatory subunit P07278 KAPR_YEAST Saccharomyces cerevisiae 3 0.7011
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7009
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7009

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