1alpha,10beta-dihydroxyguaia-3-en-6alpha,12-olide - Compound Card

1alpha,10beta-dihydroxyguaia-3-en-6alpha,12-olide

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1alpha,10beta-dihydroxyguaia-3-en-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC1=CC[C@@]2([C@H]1[C@H]1OC(=O)[C@H]([C@@H]1CC[C@]2(C)O)C)O
InChI InChI=1S/C15H22O4/c1-8-4-7-15(18)11(8)12-10(5-6-14(15,3)17)9(2)13(16)19-12/h4,9-12,17-18H,5-7H2,1-3H3/t9-,10-,11+,12-,14-,15-/m0/s1
InChIKey VBQMPXNFLQSHMH-HRSNZQSQSA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 0
TPSA 66.76
LogP 1.41
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia argentea Asteraceae Plantae 669119

Showing of synonyms

  • El-Emary NA, Makboul MA, et al. (1987). Sesquiterpene lactones from Artemisia argentea.. Phytochemistry,1987,26(1),314-315. [View]
Pubchem: 162903975
Nmrshiftdb2: 70003738

No compound-protein relationship available.

Structure

SMILES: O=C(O1)CC(C1C23)CCCC3CC=C2

Level: 0

Mol. Weight: 266.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
40.24
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
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
6.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.49
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.2
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
-0.71
Rat (Acute)
2.79
Rat (Chronic Oral)
1.64
Fathead Minnow
3.75
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
339.21
Hydration Free Energy
-8.23
Log(D) at pH=7.4
0.75
Log(P)
1.55
Log S
-1.85
Log(Vapor Pressure)
-6.21
Melting Point
179.74
pKa Acid
8.77
pKa Basic
6.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8130
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8130
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7352
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7352
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7294
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7294
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7261
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7261
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7067
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7067

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