1-epi-inuviscolide - Compound Card

1-epi-inuviscolide

Select a section from the left sidebar

1-epi-inuviscolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@@H]2C(C1=C)C[C@@H]1[C@H](CC2)CC[C@@]1(C)O
InChI InChI=1S/C14H20O3/c1-8-10-7-11-9(5-6-14(11,2)16)3-4-12(10)17-13(8)15/h9-12,16H,1,3-7H2,2H3/t9-,10?,11-,12+,14-/m1/s1
InChIKey VKYKPIJTOAOAIG-ULQVNCBJSA-N
Formula C14H20O3
HBA 3
HBD 1
MW 236.31
Rotatable Bonds 0
TPSA 46.53
LogP 2.05
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 236.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae Plantae 119186

Showing of synonyms

  • Hegazy MEF, Nakamura S, et al. (2015). Rare hydroperoxyl guaianolide sesquiterpenes from Pulicaria undulata. Phytochemistry Letters,2015,12,177-181. [View]
Pubchem: 162895096
Nmrshiftdb2: 60045949

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CCC3C(C2)CCC3

Level: 0

Mol. Weight: 236.31 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
39.04
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
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
10.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.51
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.29
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
-0.47
Rat (Acute)
2.02
Rat (Chronic Oral)
1.67
Fathead Minnow
3.87
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
314.07
Hydration Free Energy
-5.79
Log(D) at pH=7.4
1.43
Log(P)
1.86
Log S
-2.41
Log(Vapor Pressure)
-4.57
Melting Point
121.15
pKa Acid
10.16
pKa Basic
7.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8815
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8815
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8412
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8412
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8325
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8325
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8042
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8042
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7736
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7736
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7663
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7663
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7540
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7540
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7503
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7503
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7493
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7493
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7485
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7485
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7469
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7469
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7461
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7461
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7352
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7352
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7321
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7321
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7314
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7314
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7305
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7305
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7239
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7239
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7095
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7095
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7036
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7036

Download SDF