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

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

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1beta,4beta-dihydroxy-5alphaH,7alphaH,8beta-guaia-10(14),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@@](C)(O)CC[C@@]1(C(=C)C2)O
InChI InChI=1S/C15H20O4/c1-8-6-11-10(9(2)13(16)19-11)7-12-14(3,17)4-5-15(8,12)18/h10-12,17-18H,1-2,4-7H2,3H3/t10-,11+,12+,14+,15+/m1/s1
InChIKey TUXMPYMXQNASGF-SQLGEJSKSA-N
Formula C15H20O4
HBA 4
HBD 2
MW 264.32
Rotatable Bonds 0
TPSA 66.76
LogP 1.33
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 264.14
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: 162853377
Nmrshiftdb2: 60045951

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)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
42.11
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
Non-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
7.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.42
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.75
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.48
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
-0.26
Rat (Acute)
3.19
Rat (Chronic Oral)
1.65
Fathead Minnow
3.92
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
332.72
Hydration Free Energy
-7.89
Log(D) at pH=7.4
0.64
Log(P)
1.03
Log S
-2.01
Log(Vapor Pressure)
-6.65
Melting Point
155.42
pKa Acid
7.33
pKa Basic
6.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8913
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8913
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8445
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8445
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8354
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8354
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8319
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8319
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8245
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8245
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8138
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8138
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8072
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8072
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7941
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7941
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7749
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7749
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7744
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7744
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7714
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7714
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7564
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7564
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7491
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7491
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7431
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7431
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7408
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7408
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7351
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7351
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7309
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7309
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7088
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7088
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7022
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7022

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