8-desoxy-3alpha,4alpha-epoxyrupiculin-B - Compound Card

8-desoxy-3alpha,4alpha-epoxyrupiculin-B

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8-desoxy-3alpha,4alpha-epoxyrupiculin-B

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC1=C2[C@@H]3O[C@]([C@@H]2[C@H]2[C@@H](CC1)C(=C)C(=O)O2)([C@H]3O)C
InChI InChI=1S/C15H18O4/c1-6-4-5-8-7(2)14(17)18-11(8)10-9(6)12-13(16)15(10,3)19-12/h8,10-13,16H,2,4-5H2,1,3H3/t8-,10-,11+,12-,13-,15+/m0/s1
InChIKey YTVDEYRARRBPLE-WTWTUEHUSA-N
Formula C15H18O4
HBA 4
HBD 1
MW 262.3
Rotatable Bonds 0
TPSA 55.76
LogP 1.34
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 262.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Warionia saharae Asteraceae Plantae 40727

Showing of synonyms

  • Hilmi F, Sticher O, et al. (2002). New cytotoxic 6,7-cis and 6,7-trans configured guaianolides from Warionia saharae. Journal of Natural Products,2002,65,523-526. [View] [PubMed]
Pubchem: 11139915
Nmrshiftdb2: 20170335

No compound-protein relationship available.

Structure

SMILES: C1CCC(C(=C)C(=O)O2)C2C(C(O3)C4)C=1C34

Level: 0

Mol. Weight: 262.3 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
40.37
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
10.37
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.34
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.59
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.33
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
1.57
Rat (Acute)
3.5
Rat (Chronic Oral)
1.72
Fathead Minnow
3.9
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
346.75
Hydration Free Energy
-7.85
Log(D) at pH=7.4
0.94
Log(P)
1.23
Log S
-2.36
Log(Vapor Pressure)
-6.89
Melting Point
171.99
pKa Acid
8.33
pKa Basic
5.38
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 0.8239
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8239
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7792
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7792
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7520
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7520
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7090
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7090

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