1beta,6alpha-dihydroxy-8-alpha-(3'-hydroxy-isobutanoyloxy)-11-carboxymethyl-eudesm-11(13)-en-4-one - Compound Card

1beta,6alpha-dihydroxy-8-alpha-(3'-hydroxy-isobutanoyloxy)-11-carboxymethyl-eudesm-11(13)-en-4-one

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1beta,6alpha-dihydroxy-8-alpha-(3'-hydroxy-isobutanoyloxy)-11-carboxymethyl-eudesm-11(13)-en-4-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC(C(=O)O[C@H]1C[C@H]2[C@H](O)CCC(=O)[C@@H]2[C@H]([C@@H]1C(=C)C(=O)OC)O)C
InChI InChI=1S/C18H26O8/c1-8(7-19)17(23)26-13-6-10-11(20)4-5-12(21)15(10)16(22)14(13)9(2)18(24)25-3/h8,10-11,13-16,19-20,22H,2,4-7H2,1,3H3/t8?,10-,11+,13-,14+,15+,16-/m0/s1
InChIKey KIHQNRJQWOHYTL-SAHCHJOYSA-N
Formula C18H26O8
HBA 8
HBD 3
MW 370.4
Rotatable Bonds 5
TPSA 130.36
LogP -0.41
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 370.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Onopordon ambiguum Asteraceae Plantae —

Showing of synonyms

  • El-Moghazy SA, Ahmed AA, et al. (2002). A new eudesmane derivative from Onopordon ambiguum. Fitoterapia,2002,73,97-98. [View] [PubMed]
Pubchem: 162816889

No compound-protein relationship available.

Structure

SMILES: O=C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 370.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.330
Plasma Protein Binding
45.3
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
4.610
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.330
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.760
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.870
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
-3.030
Rat (Acute)
4.410
Rat (Chronic Oral)
2.700
Fathead Minnow
4.000
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
405.880
Hydration Free Energy
-11.690
Log(D) at pH=7.4
0.250
Log(P)
-0.45
Log S
-1.3
Log(Vapor Pressure)
-8.38
Melting Point
139.81
pKa Acid
6.52
pKa Basic
4.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8242
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8242
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7210
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7210
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7071
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7071
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7024
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7024

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