1beta-hydroperoxyl,4alpha-hydroxy-5alphaH,7alphaH,8betaH-guaia-10(14),11(13)-dien-8alpha,12-olide - Compound Card

1beta-hydroperoxyl,4alpha-hydroxy-5alphaH,7alphaH,8betaH-guaia-10(14),11(13)-dien-8alpha,12-olide

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1beta-hydroperoxyl,4alpha-hydroxy-5alphaH,7alphaH,8betaH-guaia-10(14),11(13)-dien-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OO[C@@]12CC[C@@]([C@@H]2C[C@H]2[C@H](CC1=C)OC(=O)C2=C)(C)O
InChI InChI=1S/C15H20O5/c1-8-6-11-10(9(2)13(16)19-11)7-12-14(3,17)4-5-15(8,12)20-18/h10-12,17-18H,1-2,4-7H2,3H3/t10-,11+,12+,14-,15+/m1/s1
InChIKey JPJJVAXMKUXVAG-NUNXZZDCSA-N
Formula C15H20O5
HBA 5
HBD 2
MW 280.32
Rotatable Bonds 1
TPSA 75.99
LogP 1.82
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 280.13
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: 122206364
Nmrshiftdb2: 70006310

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC(=C)C3C(C2)CCC3

Level: 0

Mol. Weight: 218.3 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.540
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.390
Plasma Protein Binding
49.63
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
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.440
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.670
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.360
Micronucleos
Toxic
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
-0.240
Rat (Acute)
3.330
Rat (Chronic Oral)
1.850
Fathead Minnow
3.920
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
330.550
Hydration Free Energy
-10.640
Log(D) at pH=7.4
0.500
Log(P)
0.72
Log S
-2.27
Log(Vapor Pressure)
-6.48
Melting Point
150.85
pKa Acid
7.66
pKa Basic
5.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9268
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9268
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8262
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8262
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8170
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8170
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8112
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8112
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7912
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7912
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7877
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7877
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7639
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7639
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7538
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7538
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7486
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7486
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7352
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7352
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7166
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7166
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7077
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7077
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7046
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7046
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7004
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7004

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