5-O-acetyl-inuloxin C - Compound Card

5-O-acetyl-inuloxin C

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5-O-acetyl-inuloxin C

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@]12CCCC(=C)[C@@]2(C)C[C@@H]2[C@H](C1)C(=C)C(=O)O2
InChI InChI=1S/C17H22O4/c1-10-6-5-7-17(21-12(3)18)8-13-11(2)15(19)20-14(13)9-16(10,17)4/h13-14H,1-2,5-9H2,3-4H3/t13-,14-,16-,17-/m1/s1
InChIKey LHEQUPDIFVGKIX-MUIFIZLQSA-N
Formula C17H22O4
HBA 4
HBD 0
MW 290.36
Rotatable Bonds 1
TPSA 52.6
LogP 2.93
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 290.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Inula viscosa Asteraceae-Compositae Plantae 56525

Showing of synonyms

  • Andolfi A, Zermane N, et al. (2013). Inuloxins A-D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: potential for broomrapes and field dodder management. Phytochemistry,2013,86,112-120. [View]
Pubchem: 71573982

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC3C(C2)CCCC3=C

Level: 0

Mol. Weight: 218.3 g/mol

Phytotoxicity

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
52.76
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
11.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.19
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.53
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
1.07
Rat (Acute)
2.44
Rat (Chronic Oral)
1.79
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
327.8
Hydration Free Energy
-4.12
Log(D) at pH=7.4
2.18
Log(P)
2.9
Log S
-3.6
Log(Vapor Pressure)
-4.82
Melting Point
110.08
pKa Acid
10.09
pKa Basic
6.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9060
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9060
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9026
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9026
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8750
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8750
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8666
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8666
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8616
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8616
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8112
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8112
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7968
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7968
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7830
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7830
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7813
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7813
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7800
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7800
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7783
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7783
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7774
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7774
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7710
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7710
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7677
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7677
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7612
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7612
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7564
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7564
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7497
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7497
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7492
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7492
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7436
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7436
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7405
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7405
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7382
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7382
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7371
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7371
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7356
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7356
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7326
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7326
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7244
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7244
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7243
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7243
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7236
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7236
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7223
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7223
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7179
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7179
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7103
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7103
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7050
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7050
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7037
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7037

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