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(˗)pinellic acid
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Lipid
- Subclass: Fatty Acid
| Canonical Smiles | CCCCC[C@@H]([C@H](/C=C/[C@H](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)/b14-13+/t15-,16-,17-/m0/s1 |
| InChIKey | MDIUMSLCYIJBQC-MVFSOIOZSA-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 | Helianthemum sessiliflorum | Cistaceae | Plantae | 2650562 |
| 2 | Ganoderma sp | Ganodermataceae | Plantae | 1869158 |
| 3 | Galium brunneum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
(˗)pinellic acid
Pinellic acid
97134-11-7
9,12,13-TriHOME
Dihydrofulgidic acid
(E,9S,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid
CHEBI:34506
9S,12S,13S-trihydroxy-10E-octadecenoate
9(S),12(S),13(S)-Trihydroxy-10(E)-octadecenoate
(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoate
(9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid
9S,12S,13S-trihydroxy-10E-octadecenoic acid
9(S),12(S),13(S)-Trihydroxy-10(E)-octadecenoic acid
9(S),12(S),13(S)-TriHOME
(10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoic acid
9,12,13-Trihydroxyoctadec-10-enoic acid
SCHEMBL3989371
CHEMBL4436085
MDIUMSLCYIJBQC-MVFSOIOZSA-N
DTXSID001317644
LMFA02000014
AKOS040755725
DA-60617
PD131487
Q27116118
(9s,12s,13s)-e-9,12,13-trihydroxy-10-octadecaenoic acid
- Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]
- Benabdelaziz I, Haba H, et al. (2015). Lignans and other constituents from Helianthemum sessiliflorum Pers.. Records of Natural Products,2015,9(3),342-348. [View]
- Kojom Foko L.P, Jakhan J, et al. (2024). New antimalarial lanostane triterpenes from a new isolate of Egyptian Ganoderma species. Journal of parasitic diseases : official organ of the Indian Society for Parasitology, 2024, 48(3), 610-623. [View] [PubMed]
Pubchem:
9858729
Cas:
97134-11-7
Zinc:
ZINC000012496469
Kegg Ligand:
C14833
Chebi:
34506
Nmrshiftdb2:
60023178
Metabolights:
MTBLC34506
Chembl:
CHEMBL4436085
CPRiL:
259677
No scaffolds available.
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.59
- 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
- -3.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.66
- Plasma Protein Binding
- 54.02
- 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
- 2.5
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.58
- 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
- 4.41
- 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
- -1.44
- Rat (Acute)
- 1.7
- Rat (Chronic Oral)
- 2.94
- 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
- 390.46
- Hydration Free Energy
- -9.13
- Log(D) at pH=7.4
- 0.16
- Log(P)
- 2.72
- Log S
- -2.53
- Log(Vapor Pressure)
- -9.74
- Melting Point
- 66.58
- pKa Acid
- 4.71
- pKa Basic
- 6.03
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9105 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9105 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8931 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8931 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.8816 |
| thiamine diphosphokinase | Q82ZE3 | Q82ZE3_ENTFA | Enterococcus faecalis | 3 | 0.8816 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.8783 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.8783 |
| Glycogenin-1 | P46976 | GLYG_HUMAN | Homo sapiens | 3 | 0.8764 |
| Glycogenin-1 | P46976 | GLYG_HUMAN | Homo sapiens | 3 | 0.8764 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 3 | 0.8738 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 3 | 0.8738 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 3 | 0.8738 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 3 | 0.8738 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8707 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8707 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8698 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8698 |
| Phenolphthiocerol/phthiocerol polyketide synthase subunit C | P96202 | PPSC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8689 |
| Phenolphthiocerol/phthiocerol polyketide synthase subunit C | P96202 | PPSC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8689 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.8656 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.8656 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8641 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8641 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.8618 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.8618 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8541 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8541 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.8372 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.8372 |
| Beta-glucosidase 1A | Q25BW5 | BGL1A_PHACH | Phanerodontia chrysosporium | 3 | 0.8353 |
| Beta-glucosidase 1A | Q25BW5 | BGL1A_PHACH | Phanerodontia chrysosporium | 3 | 0.8353 |
| Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.8331 |
| Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.8331 |
| Bile salt hydrolase/transferase | P54965 | CBH_CLOPE | Clostridium perfringens | 3 | 0.8320 |
| Bile salt hydrolase/transferase | P54965 | CBH_CLOPE | Clostridium perfringens | 3 | 0.8320 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8142 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8142 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8141 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8141 |
| Suppressor of disruption of TFIIS | P53078 | SDT1_YEAST | Saccharomyces cerevisiae | 3 | 0.8087 |
| Suppressor of disruption of TFIIS | P53078 | SDT1_YEAST | Saccharomyces cerevisiae | 3 | 0.8087 |
| 4-alpha-glucanotransferase | O87172 | MALQ_THETH | Thermus thermophilus | 3 | 0.8041 |
| 4-alpha-glucanotransferase | O87172 | MALQ_THETH | Thermus thermophilus | 3 | 0.8041 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 3 | 0.7986 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 3 | 0.7986 |
| Regucalcin | Q64374 | RGN_MOUSE | Mus musculus | 3 | 0.7897 |
| Regucalcin | Q64374 | RGN_MOUSE | Mus musculus | 3 | 0.7897 |
| Conserved hypthetical protein | Q8GGP1 | Q8GGP1_STRAZ | Streptomyces atroolivaceus | 4 | 0.7780 |
| Conserved hypthetical protein | Q8GGP1 | Q8GGP1_STRAZ | Streptomyces atroolivaceus | 4 | 0.7780 |
| Probable phosphoketolase | D6PAH1 | D6PAH1_BIFBR | Bifidobacterium breve | 4 | 0.7689 |
| Probable phosphoketolase | D6PAH1 | D6PAH1_BIFBR | Bifidobacterium breve | 4 | 0.7689 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7604 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7604 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7581 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7581 |
| Glucosidase II subunit alpha | Q9STC1 | Q9STC1_GRALE | Gracilariopsis lemaneiformis | 3 | 0.7505 |
| Glucosidase II subunit alpha | Q9STC1 | Q9STC1_GRALE | Gracilariopsis lemaneiformis | 3 | 0.7505 |
| Fluoroacetyl-CoA thioesterase | Q1EMV2 | FLK_STRCT | Streptantibioticus cattleyicolor | 3 | 0.7499 |
| Fluoroacetyl-CoA thioesterase | Q1EMV2 | FLK_STRCT | Streptantibioticus cattleyicolor | 3 | 0.7499 |
| Lactose operon repressor | P03023 | LACI_ECOLI | Escherichia coli | 3 | 0.7479 |
| Lactose operon repressor | P03023 | LACI_ECOLI | Escherichia coli | 3 | 0.7479 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7427 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7427 |
| Raucaffricine-O-beta-D-glucosidase | Q9SPP9 | RG1_RAUSE | Rauvolfia serpentina | 3 | 0.7414 |
| Raucaffricine-O-beta-D-glucosidase | Q9SPP9 | RG1_RAUSE | Rauvolfia serpentina | 3 | 0.7414 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7345 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7345 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7323 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7323 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7304 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7304 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7293 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7293 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7290 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7290 |
| Glyoxylate carboligase | P0AEP7 | GCL_ECOLI | Escherichia coli | 3 | 0.7241 |
| Glyoxylate carboligase | P0AEP7 | GCL_ECOLI | Escherichia coli | 3 | 0.7241 |
| Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 3 | 0.7202 |
| Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 3 | 0.7202 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7189 |
| Sodium/potassium-transporting ATPase subunit alpha | Q4H132 | Q4H132_SQUAC | Squalus acanthias | 2 | 0.7189 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7167 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7167 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7152 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7152 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7120 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7120 |
| Fatty acid-binding protein 2, liver | P81400 | FABP2_AMBME | Ambystoma mexicanum | 3 | 0.7104 |
| Fatty acid-binding protein 2, liver | P81400 | FABP2_AMBME | Ambystoma mexicanum | 3 | 0.7104 |
| TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 2 | 0.7073 |
| TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 2 | 0.7073 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.7064 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 2 | 0.7064 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 2 | 0.7064 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.7064 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 2 | 0.7055 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 2 | 0.7055 |