(3aR,6S,7aR)-octahydro-7-(1-hydroxyprop-2-en-2-yl)-6-methyl-3-methylene-2-oxo-6-vinylbenzofuran-4-yl 2-(hydroxymethyl)acrylate - Compound Card

(3aR,6S,7aR)-octahydro-7-(1-hydroxyprop-2-en-2-yl)-6-methyl-3-methylene-2-oxo-6-vinylbenzofuran-4-yl 2-(hydroxymethyl)acrylate

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(3aR,6S,7aR)-octahydro-7-(1-hydroxyprop-2-en-2-yl)-6-methyl-3-methylene-2-oxo-6-vinylbenzofuran-4-yl 2-(hydroxymethyl)acrylate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC(=C)C(=O)OC1C[C@](C)(C=C)[C@H]([C@@H]2[C@@H]1C(=C)C(=O)O2)C(=C)CO
InChI InChI=1S/C19H24O6/c1-6-19(5)7-13(24-17(22)11(3)9-21)14-12(4)18(23)25-16(14)15(19)10(2)8-20/h6,13-16,20-21H,1-4,7-9H2,5H3/t13?,14-,15+,16+,19+/m1/s1
InChIKey NUWSDQMCCHNVBZ-BUIIFPGESA-N
Formula C19H24O6
HBA 6
HBD 2
MW 348.4
Rotatable Bonds 6
TPSA 93.06
LogP 1.31
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 348.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus intybaceus Asteraceae Plantae 64995

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 162880468

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CCCC2

Level: 0

Mol. Weight: 348.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.490
Plasma Protein Binding
56.9
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
9.550
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.420
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.330
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.200
Micronucleos
Safe
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
1.670
Rat (Acute)
3.460
Rat (Chronic Oral)
2.190
Fathead Minnow
3.930
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
364.570
Hydration Free Energy
-8.860
Log(D) at pH=7.4
1.470
Log(P)
1.36
Log S
-3.11
Log(Vapor Pressure)
-7.85
Melting Point
117.77
pKa Acid
6.63
pKa Basic
4.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8118
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8118
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7667
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7667
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7533
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7533
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7181
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7181

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