Lacitemzine - Compound Card

Lacitemzine

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Lacitemzine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC(=O)C(=C)[C@H]1CC2=C(C)CC[C@@]32O[C@H]1C[C@@H]3C
InChI InChI=1S/C15H20O3/c1-8-4-5-15-9(2)6-13(18-15)11(7-12(8)15)10(3)14(16)17/h9,11,13H,3-7H2,1-2H3,(H,16,17)/t9-,11+,13-,15+/m0/s1
InChIKey DYMHDZYYXFBFRO-XPGAZNKBSA-N
Formula C15H20O3
HBA 2
HBD 1
MW 248.32
Rotatable Bonds 2
TPSA 46.53
LogP 2.92
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria laciniata Asteraceae Plantae 557695

Showing of synonyms

  • Ghouila H, Beyaoui A, et al. (2008). Lacitemzine, a novel sesquiterpene acid from the Tunisian plant Pulicaria laciniata ( Coss. et Kral.) Thell. Tetrahedron Letters,2008,49,5721-5723. [View]
Pubchem: 102475426
Nmrshiftdb2: 60056649

No compound-protein relationship available.

Structure

SMILES: C1CC=C(C123)CCC(O3)CC2

Level: 0

Mol. Weight: 248.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
47.02
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
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
6.62
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.38
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.8
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.0
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
1.25
Rat (Acute)
2.29
Rat (Chronic Oral)
1.85
Fathead Minnow
3.92
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
331.57
Hydration Free Energy
-7.51
Log(D) at pH=7.4
0.16
Log(P)
3.12
Log S
-2.82
Log(Vapor Pressure)
-5.94
Melting Point
137.36
pKa Acid
4.14
pKa Basic
8.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8797
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8797
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8357
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8357
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7983
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7983
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7623
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7623
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7534
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7534
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7394
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7394
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7389
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7389
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7347
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7347
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7335
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7335
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7258
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7258
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7233
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7233
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7218
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7218
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7205
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7205
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7202
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7202
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7174
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7174
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7093
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7093
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7071
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7071
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7027
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7027
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7002
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7002

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