9alpha-hydroxy-4alpha,15-dihydro-zaluzanin C - Compound Card

9alpha-hydroxy-4alpha,15-dihydro-zaluzanin C

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9alpha-hydroxy-4alpha,15-dihydro-zaluzanin C

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O[C@@H]1C[C@@H]2[C@H]([C@H]1C)[C@H]1OC(=O)[C@H]([C@@H]1C[C@H](C2=C)O)C
InChI InChI=1S/C15H22O4/c1-6-9-4-12(17)8(3)13(9)14-10(5-11(6)16)7(2)15(18)19-14/h7-14,16-17H,1,4-5H2,2-3H3/t7-,8-,9-,10-,11+,12+,13-,14-/m0/s1
InChIKey FZHVZHPJLXWJIZ-OPEDVLRTSA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 0
TPSA 66.76
LogP 1.12
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Launaea arborescens Asteraceae Plantae 43199

Showing of synonyms

  • Bitam F, Ciavatta ML, et al. (2008). Chemical characterisation of the terpenoid constituents of the Algerian plant Launaea arborescens. Phytochemistry,2008,69,2984-2992. [View] [PubMed]
Pubchem: 163078533

No compound-protein relationship available.

Structure

SMILES: C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 266.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.42
Plasma Protein Binding
50.38
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
9.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.56
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.94
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
3.93
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
-1.11
Rat (Acute)
3.83
Rat (Chronic Oral)
1.92
Fathead Minnow
3.89
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
359.43
Hydration Free Energy
-8.57
Log(D) at pH=7.4
0.37
Log(P)
0.5
Log S
-1.64
Log(Vapor Pressure)
-6.64
Melting Point
173.7
pKa Acid
8.23
pKa Basic
5.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8926
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8926
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8638
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8638
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8602
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8602
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8383
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8383
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8347
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8347
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8109
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8109
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7985
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7985
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7922
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7922
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7779
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7779
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7772
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7772
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7590
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7590
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7580
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7580
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7519
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7519
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7457
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7457
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7366
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7366
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7304
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7304
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7291
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7291
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7256
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7256
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7201
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7201
Bile acid receptor Q62735 NR1H4_RAT Rattus norvegicus 4 0.7190
Bile acid receptor Q62735 NR1H4_RAT Rattus norvegicus 4 0.7190
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7124
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7124

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