9,12,13-trihydroxyoctadecadienoic acid - Compound Card

9,12,13-trihydroxyoctadecadienoic acid

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9,12,13-trihydroxyoctadecadienoic acid

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Fatty Acid
Canonical Smiles CCCCCC(C(CCC(CCC/C=C/C=C/C(=O)O)O)O)O
InChI InChI=1S/C18H32O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h4,6,9,12,15-17,19-21H,2-3,5,7-8,10-11,13-14H2,1H3,(H,22,23)/b6-4+,12-9+
InChIKey CIIIRTKAWCRSFV-ISVYGWFVSA-N
Formula C18H32O5
HBA 4
HBD 4
MW 328.45
Rotatable Bonds 14
TPSA 97.99
LogP 2.8
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 328.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ammoides atlantica Apiaceae Plantae 386050
2 Rosmarinuseriocalyx Lamiaceae Plantae

Showing of synonyms

  • Benteldjoune M, Boudiar T, et al. (2021). Antioxidant activity and characterization of flavonoids and phenolic acids of Ammoides atlantica by RP–UHPLC– ESI–QTOF–MS. Nat Prod Res, 2021, 35(10), 1639-1643.. [View] [PubMed]
  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.54
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
14.32
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
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
1.91
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.6
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.96
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.33
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
4.12
Rat (Acute)
1.73
Rat (Chronic Oral)
3.01
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
388.8
Hydration Free Energy
-9.75
Log(D) at pH=7.4
-0.13
Log(P)
2.64
Log S
-2.74
Log(Vapor Pressure)
-8.88
Melting Point
84.33
pKa Acid
5.78
pKa Basic
5.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9474
Bile salt hydrolase/transferase P54965 CBH_CLOPE Clostridium perfringens 3 0.9269
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9053
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8959
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8892
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8845
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.8728
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 4 0.8711
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8699
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.8630
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8535
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8526
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8481
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.8405
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.8402
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8362
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8328
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.8270
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.8233
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.8197
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8185
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8078
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.8074
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8064
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8020
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8015
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 4 0.7961
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7868
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7864
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7850
Fluoroacetyl-CoA thioesterase Q1EMV2 FLK_STRCT Streptantibioticus cattleyicolor 3 0.7841
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7778
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7770
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7746
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7731
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7725
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7700
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7694
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7651
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7650
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7630
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7588
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7584
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7571
Fatty acid-binding protein 2, liver P81400 FABP2_AMBME Ambystoma mexicanum 3 0.7548
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7474
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7406
Regucalcin Q64374 RGN_MOUSE Mus musculus 3 0.7382
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7320
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7313
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7300
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7294
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7283
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7202
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7194
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.7178
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.7172
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7160
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7142
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7140
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7140
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7120
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7117
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7100
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7095
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7063
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7051
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7029
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7000

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