Sciadonic acid - Compound Card

Sciadonic acid

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Sciadonic acid

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Lipid
    • Subclass: Unsaturated Fatty Acid
Canonical Smiles CCCCC/C=C\C/C=C\CCCC/C=C\CCCC(=O)O
InChI InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,15-16H,2-5,8,11-14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,16-15-
InChIKey PRHHYVQTPBEDFE-URZBRJKDSA-N
Formula C20H34O2
HBA 1
HBD 1
MW 306.49
Rotatable Bonds 15
TPSA 37.3
LogP 6.44
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 306.26
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Juniperus phoenicea Cupressaceae Plantae 61308

Showing of synonyms

  • Nasri N, Tlili N, et al. (2011). Chemical compounds from Phoenician juniper berries (Juniperus phoenicea). Natural Product Research,2011,25(18),1733-1742. [View]
Pubchem: 445084
Chebi: 82832
Nmrshiftdb2: 60059229
Metabolights: MTBLC82832
CPRiL: 30347

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.32
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.5
Plasma Protein Binding
60.27
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
-1.44
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.46
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.23
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.17
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
Toxic
NR-TR
Safe
T. Pyriformis
1.87
Rat (Acute)
1.47
Rat (Chronic Oral)
2.43
Fathead Minnow
4.18
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
373.48
Hydration Free Energy
-4.64
Log(D) at pH=7.4
2.85
Log(P)
7.58
Log S
-3.95
Log(Vapor Pressure)
-6.27
Melting Point
-11.1
pKa Acid
6.25
pKa Basic
8.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.9910
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.9910
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.8666
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.8666
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.8571
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.8571
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7727
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7727
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7480
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7480
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7450
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7450
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7419
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7419
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7364
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7364
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7346
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7346
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7335
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7335
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7205
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7205
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7178
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7178
12-oxophytodienoate reductase 1 Q9XG54 OPR1_SOLLC Solanum lycopersicum 2 0.7128
12-oxophytodienoate reductase 1 Q9XG54 OPR1_SOLLC Solanum lycopersicum 2 0.7128
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7106
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7106
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7101
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7101
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7088
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7088
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7082
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7082
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7012
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7012

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