(6R,7R,8S,3'R) -8alpha-(3,4-dihydroxy-2-methylenebutanoyloxy)-15-acetoxyhelianga-1(10),4(5),11(13)-trien-6-olide - Compound Card

(6R,7R,8S,3'R) -8alpha-(3,4-dihydroxy-2-methylenebutanoyloxy)-15-acetoxyhelianga-1(10),4(5),11(13)-trien-6-olide

Select a section from the left sidebar

(6R,7R,8S,3'R) -8alpha-(3,4-dihydroxy-2-methylenebutanoyloxy)-15-acetoxyhelianga-1(10),4(5),11(13)-trien-6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC[C@H](C(=C)C(=O)O[C@H]1C/C(=C/CC/C(=C\[C@@H]2[C@@H]1C(=C)C(=O)O2)/COC(=O)C)/C)O
InChI InChI=1S/C22H28O8/c1-12-6-5-7-16(11-28-15(4)24)9-19-20(14(3)22(27)30-19)18(8-12)29-21(26)13(2)17(25)10-23/h6,9,17-20,23,25H,2-3,5,7-8,10-11H2,1,4H3/b12-6+,16-9+/t17-,18+,19-,20-/m1/s1
InChIKey WRINAAVIHYRMOF-DLWFREQBSA-N
Formula C22H28O8
HBA 8
HBD 2
MW 420.46
Rotatable Bonds 6
TPSA 119.36
LogP 1.53
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 420.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea tougourensis Asteraceae Plantae 1486586

Showing of synonyms

  • Nacer A, Merza J, et al. (2012). Sesquiterpene lactones from Centaurea tougourensis. Biochemical Systematics and Ecology,2012,43,163-165. [View]
Pubchem: 162885999
Nmrshiftdb2: 70046330

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 420.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
54.88
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.26
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.73
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.12
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-16.33
Rat (Acute)
3.27
Rat (Chronic Oral)
2.57
Fathead Minnow
4.48
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
423.07
Hydration Free Energy
-6.12
Log(D) at pH=7.4
1.73
Log(P)
1.48
Log S
-2.9
Log(Vapor Pressure)
-8.9
Melting Point
133.47
pKa Acid
7.54
pKa Basic
4.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8744
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8744
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7904
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7904
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7812
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7812
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7763
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7763
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7589
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7589
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7587
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7587
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7293
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7293
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7042
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7042

Download SDF