Inuloxin C - Compound Card

Inuloxin C

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Inuloxin C

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2[C@@H](C1=C)C[C@]1([C@@](C2)(C)C(=C)CCC1)O
InChI InChI=1S/C15H20O3/c1-9-5-4-6-15(17)7-11-10(2)13(16)18-12(11)8-14(9,15)3/h11-12,17H,1-2,4-8H2,3H3/t11-,12-,14-,15-/m1/s1
InChIKey LRRAPLGHLCOGIZ-QHSBEEBCSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.36
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 Inula viscosa Asteraceae 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: 71573979

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 248.32 g/mol

Phytotoxicity

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
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)
0.52
Plasma Protein Binding
45.58
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.07
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.79
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.85
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
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)
2.6
Rat (Chronic Oral)
1.52
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
317.83
Hydration Free Energy
-5.56
Log(D) at pH=7.4
1.76
Log(P)
1.95
Log S
-2.65
Log(Vapor Pressure)
-4.99
Melting Point
127.88
pKa Acid
8.86
pKa Basic
6.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9127
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9127
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9028
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9028
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8667
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8667
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8629
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8629
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8487
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8487
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8378
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8378
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8216
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8216
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8140
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8140
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8083
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8083
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8039
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8039
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8027
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8027
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7947
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7947
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7837
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7837
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7836
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7836
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7547
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7547
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7547
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7547
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7543
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7543
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7483
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7483
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7385
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7385
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7359
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7359
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7266
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7266
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7243
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7243
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7211
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7211
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7159
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7159
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7156
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7156
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7151
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7151
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7093
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7093
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7071
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7071
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7068
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7068
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7050
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7050
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7050
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7050
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7047
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7047
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7034
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7034

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