9alpha-hydroxy-11beta,13-dihydroparthenolide-9-O-beta-D-glucopyranoside - Compound Card

9alpha-hydroxy-11beta,13-dihydroparthenolide-9-O-beta-D-glucopyranoside

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9alpha-hydroxy-11beta,13-dihydroparthenolide-9-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone Glycoside
Canonical Smiles OCC1O[C@H](O[C@@H]2C[C@H]3[C@H](C)C(=O)O[C@@H]3[C@@H]3O[C@@]3(CC/C=C/2\C)C)[C@@H](C([C@H]1O)O)O
InChI InChI=1S/C21H32O9/c1-9-5-4-6-21(3)18(30-21)17-11(10(2)19(26)29-17)7-12(9)27-20-16(25)15(24)14(23)13(8-22)28-20/h5,10-18,20,22-25H,4,6-8H2,1-3H3/b9-5+/t10-,11-,12+,13?,14-,15?,16+,17-,18-,20-,21+/m0/s1
InChIKey HAIUWTQIMLYRIO-HUTOTJRPSA-N
Formula C21H32O9
HBA 9
HBD 4
MW 428.48
Rotatable Bonds 3
TPSA 138.21
LogP -0.36
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 428.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Asteriscus graveolens Asteraceae Plantae 73976

Showing of synonyms

  • Achoub H, Mencherini T, et al. (2021). New sesquiterpenes from Asteriscus graveolens. Natural product research, 2021, 35(13), 2190-2198. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC=CC(CC3C1OC(=O)C3)OC4CCCCO4

Level: 1

Mol. Weight: 428.48 g/mol

Structure

SMILES: C12C(O2)CCC=CCCC3C1OC(=O)C3

Level: 0

Mol. Weight: 428.48 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 428.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.32
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
40.82
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.45
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.62
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
-36.38
Rat (Acute)
3.25
Rat (Chronic Oral)
2.82
Fathead Minnow
3.81
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
481.47
Hydration Free Energy
-6.06
Log(D) at pH=7.4
0.05
Log(P)
0.25
Log S
-2.19
Log(Vapor Pressure)
-11.92
Melting Point
151.8
pKa Acid
6.27
pKa Basic
4.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7683
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7579
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7451
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7393
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7387

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