1beta,4beta-peroxide-5alphaH,7alphaH,8beta,10betaH-guaia-2,11(13)- dien-8beta,12-olide - Compound Card

1beta,4beta-peroxide-5alphaH,7alphaH,8beta,10betaH-guaia-2,11(13)- dien-8beta,12-olide

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1beta,4beta-peroxide-5alphaH,7alphaH,8beta,10betaH-guaia-2,11(13)- dien-8beta,12-olide

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1C(=O)O[C@@H]2[C@@H]1C[C@H]1[C@@]3(C)OO[C@]1([C@@H](C2)C)C=C3
InChI InChI=1S/C15H18O4/c1-8-6-11-10(9(2)13(16)17-11)7-12-14(3)4-5-15(8,12)19-18-14/h4-5,8,10-12H,2,6-7H2,1,3H3/t8-,10-,11+,12+,14+,15+/m1/s1
InChIKey OAGNQVQMOBMOOP-VDBHERJRSA-N
Formula C15H18O4
HBA 4
HBD 0
MW 262.3
Rotatable Bonds 0
TPSA 44.76
LogP 2.16
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 262.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae-Compositae 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: 162816867

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(CC2)C1CC(C234)C(OO4)C=C3

Level: 0

Mol. Weight: 234.25 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
39.24
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.54
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.5
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.26
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
0.62
Rat (Acute)
3.27
Rat (Chronic Oral)
1.68
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
325.0
Hydration Free Energy
-4.63
Log(D) at pH=7.4
1.74
Log(P)
2.44
Log S
-3.29
Log(Vapor Pressure)
-4.27
Melting Point
110.53
pKa Acid
8.1
pKa Basic
5.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9121
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9121
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8805
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8805
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8754
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8754
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8306
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8306
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7951
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7951
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7716
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7716
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7704
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7704
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7696
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7696
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7518
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7518
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7319
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7319
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7314
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7314
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7149
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7149
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7038
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7038
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7014
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7014

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