Trihydroxy-octadecenoic acid - Compound Card

Trihydroxy-octadecenoic acid

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Trihydroxy-octadecenoic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Lipid
    • Subclass: Fatty Acid
Canonical Smiles CCCCCC(C(C=CC(CCCCCCCC(=O)O)O)O)O
InChI InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)
InChIKey MDIUMSLCYIJBQC-UHFFFAOYSA-N
Formula C18H34O5
HBA 4
HBD 4
MW 330.46
Rotatable Bonds 15
TPSA 97.99
LogP 3.02
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.83
Exact Mass 330.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cynara cardunculus Asteraceae Plantae 4265

Showing of synonyms

  • Farag MA, El-Ahmady SH, et al. (2013). Metabolomics driven analysis of artichoke leaf and its commercial products via UHPLC–q-TOF-MS and chemometrics. Phytochemistry,2013,95,177-187. [View] [PubMed]
Pubchem: 5282966
Nmrshiftdb2: 70019515

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
1.03
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.52
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.33
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.87
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.38
Micronucleos
Safe
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
0.94
Rat (Acute)
1.71
Rat (Chronic Oral)
2.96
Fathead Minnow
4.04
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
385.03
Hydration Free Energy
-9.07
Log(D) at pH=7.4
0.07
Log(P)
2.72
Log S
-2.43
Log(Vapor Pressure)
-9.34
Melting Point
63.05
pKa Acid
4.7
pKa Basic
6.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.9413
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.9413
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9280
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9280
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9265
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9265
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9264
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9264
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9151
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9151
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.9093
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.9093
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.9073
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.9073
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.9050
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.9050
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9011
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9011
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8988
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8988
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.8974
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.8974
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8962
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8962
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8946
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8946
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.8906
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.8906
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.8897
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.8897
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.8653
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.8653
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8616
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8616
Fluoroacetyl-CoA thioesterase Q1EMV2 FLK_STRCT Streptantibioticus cattleyicolor 3 0.8581
Fluoroacetyl-CoA thioesterase Q1EMV2 FLK_STRCT Streptantibioticus cattleyicolor 3 0.8581
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8527
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8527
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 4 0.8473
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 4 0.8473
Menin O00255 MEN1_HUMAN Homo sapiens 3 0.8464
Menin O00255 MEN1_HUMAN Homo sapiens 3 0.8464
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8452
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8452
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8437
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8437
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.8429
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.8429
Bile salt hydrolase/transferase P54965 CBH_CLOPE Clostridium perfringens 3 0.8417
Bile salt hydrolase/transferase P54965 CBH_CLOPE Clostridium perfringens 3 0.8417
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8311
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8311
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.8291
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.8291
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8287
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8287
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8205
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8205
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.8176
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.8176
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.8139
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.8139
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8061
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8061
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7938
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7938
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 4 0.7912
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 4 0.7912
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7900
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7900
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7884
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7884
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7864
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7864
Isocitrate/homoisocitrate dehydrogenase Q5SIJ1 HICDH_THET8 Thermus thermophilus 3 0.7843
Isocitrate/homoisocitrate dehydrogenase Q5SIJ1 HICDH_THET8 Thermus thermophilus 3 0.7843
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.7839
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.7839
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7808
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7808
Regucalcin Q64374 RGN_MOUSE Mus musculus 3 0.7748
Regucalcin Q64374 RGN_MOUSE Mus musculus 3 0.7748
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7744
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7744
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7731
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7731
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7695
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7695
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7663
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7663
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7662
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7662
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7662
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7662
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7642
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7642
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7633
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7633
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7629
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7629
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7604
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7604
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7561
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7561
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7543
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7543
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7541
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7541
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7533
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7533
Suppressor of disruption of TFIIS P53078 SDT1_YEAST Saccharomyces cerevisiae 3 0.7487
Suppressor of disruption of TFIIS P53078 SDT1_YEAST Saccharomyces cerevisiae 3 0.7487
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7476
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7476
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7460
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7460
Fatty acid-binding protein 2, liver P81400 FABP2_AMBME Ambystoma mexicanum 3 0.7453
Fatty acid-binding protein 2, liver P81400 FABP2_AMBME Ambystoma mexicanum 3 0.7453
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7357
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7357
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7347
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7347
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7342
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7342
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7337
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7337
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7308
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7308
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7306
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7306
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7303
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7303
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7223
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7223
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7209
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7209
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.7208
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.7208
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7190
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7190
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7189
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7189
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7128
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7128
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7123
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7123
Strictosidine-O-beta-D-glucosidase Q8GU20 SG1_RAUSE Rauvolfia serpentina 4 0.7093
Strictosidine-O-beta-D-glucosidase Q8GU20 SG1_RAUSE Rauvolfia serpentina 4 0.7093
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7092
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7092
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7088
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7088
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7040
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7040
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7039
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7039
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7031
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7031
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7012
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7012
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7008
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7008

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