9alpha-hydroxy-11beta,13-dihydro-3-epi-zaluzanin C - Compound Card

9alpha-hydroxy-11beta,13-dihydro-3-epi-zaluzanin C

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9alpha-hydroxy-11beta,13-dihydro-3-epi-zaluzanin C

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1[C@H](O)C[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@H](C3=C)O)OC(=O)[C@H]2C
InChI InChI=1S/C15H20O4/c1-6-9-4-12(17)8(3)13(9)14-10(5-11(6)16)7(2)15(18)19-14/h7,9-14,16-17H,1,3-5H2,2H3/t7-,9-,10-,11+,12+,13-,14-/m0/s1
InChIKey GLMKTMOFCGDFFQ-YITKKWGKSA-N
Formula C15H20O4
HBA 4
HBD 2
MW 264.32
Rotatable Bonds 0
TPSA 66.76
LogP 1.04
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Launaea arborescens Asteraceae-Compositae 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: 25180957
Nmrshiftdb2: 70022814

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 218.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.36
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
47.56
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
8.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.52
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.55
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.8
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
-1.42
Rat (Acute)
3.71
Rat (Chronic Oral)
1.96
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
358.75
Hydration Free Energy
-8.52
Log(D) at pH=7.4
0.22
Log(P)
0.24
Log S
-1.64
Log(Vapor Pressure)
-6.8
Melting Point
172.09
pKa Acid
7.46
pKa Basic
5.94
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 0.9130
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.9130
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8740
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8740
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8445
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8445
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8366
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8366
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8150
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8150
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8023
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8023
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7933
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7933
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7928
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7928
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7909
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7909
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7841
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7841
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7830
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7830
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7757
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7757
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7703
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7703
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7588
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7588
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7548
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7548
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7538
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7538
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7509
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7509
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7428
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7428
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7415
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7415
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7405
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7405
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7323
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7323
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7256
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7256
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7240
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7240
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7215
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7215
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7214
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7214
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7180
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7180
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7117
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7117

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