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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OO[C@@]1(C)C[C@@H]2OC(=O)C(=C)[C@H]2C[C@@H]2C1=CC[C@]2(C)O
InChI InChI=1S/C15H20O5/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,20-18)7-12(9)19-13(8)16/h4,9,11-12,17-18H,1,5-7H2,2-3H3/t9-,11-,12+,14+,15+/m1/s1
InChIKey LTPWXJPRGRSAIO-FWTMIXAASA-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 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: 122206365
Nmrshiftdb2: 60045950

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(CC2)C1CC(C2=3)CCC3

Level: 0

Mol. Weight: 280.32 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.500
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.400
Plasma Protein Binding
43.86
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
9.290
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.090
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.680
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.510
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.250
Rat (Acute)
3.530
Rat (Chronic Oral)
1.760
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
328.870
Hydration Free Energy
-10.240
Log(D) at pH=7.4
0.480
Log(P)
0.4
Log S
-1.89
Log(Vapor Pressure)
-5.84
Melting Point
157.73
pKa Acid
7.87
pKa Basic
5.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9012
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9012
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8452
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8452
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8316
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8316
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8150
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8150
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8082
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8082
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8006
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8006
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7947
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7947
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7612
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7612
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7551
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7551
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7539
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7539
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7441
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7441
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7330
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7330
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7273
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7273
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7178
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7178
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7155
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7155
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7089
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7089
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7056
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7056

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