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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2C[C@@H](CC[C@]2(CCC1)C)C(=C)C(=O)O
InChI InChI=1S/C15H22O3/c1-10(14(17)18)11-5-7-15(2)6-3-4-12(9-16)13(15)8-11/h11,16H,1,3-9H2,2H3,(H,17,18)/t11-,15-/m1/s1
InChIKey AZBXHHKPJVBKTN-IAQYHMDHSA-N
Formula C15H22O3
HBA 2
HBD 2
MW 250.34
Rotatable Bonds 3
TPSA 57.53
LogP 2.91
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 250.16
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: 163059403
Nmrshiftdb2: 60045854

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C1=2)CCCC2

Level: 0

Mol. Weight: 250.34 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
52.26
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
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
3.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.88
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.17
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
0.16
Rat (Acute)
2.35
Rat (Chronic Oral)
2.57
Fathead Minnow
3.93
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
337.02
Hydration Free Energy
-7.9
Log(D) at pH=7.4
0.12
Log(P)
2.76
Log S
-2.8
Log(Vapor Pressure)
-5.73
Melting Point
133.92
pKa Acid
4.56
pKa Basic
8.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9299
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9299
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9194
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9194
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.9115
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.9115
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8887
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8887
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8597
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8597
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8513
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8513
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8432
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8432
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8138
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8138
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8126
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8126
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7987
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7987
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7971
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7971
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7910
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7910
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7905
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7905
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7871
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7871
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7677
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7677
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7602
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7602
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7595
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7595
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7458
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7458
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7319
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7319
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7305
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7305
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7288
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7288
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7234
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7234
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7066
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7066
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7059
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7059
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7010
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7010

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