3beta-O-(1,2-didehydro-3-oxo-costoyloxy)- 4beta,10beta-dihydroxy-guaia-1(2)-en-6alpha,12-olide - Compound Card

3beta-O-(1,2-didehydro-3-oxo-costoyloxy)- 4beta,10beta-dihydroxy-guaia-1(2)-en-6alpha,12-olide

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3beta-O-(1,2-didehydro-3-oxo-costoyloxy)- 4beta,10beta-dihydroxy-guaia-1(2)-en-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone Dimer
Canonical Smiles O=C(C(=C)[C@@H]1CC[C@@]2([C@@H](C1)C(=C)C(=O)C=C2)C)O[C@H]1C=C2[C@H]([C@@]1(C)O)[C@H]1OC(=O)C(=C)[C@@H]1CC[C@]2(C)O
InChI InChI=1S/C30H36O7/c1-15(18-7-10-28(4)11-9-22(31)17(3)20(28)13-18)26(32)36-23-14-21-24(30(23,6)35)25-19(8-12-29(21,5)34)16(2)27(33)37-25/h9,11,14,18-20,23-25,34-35H,1-3,7-8,10,12-13H2,4-6H3/t18-,19+,20+,23+,24+,25+,28+,29+,30+/m1/s1
InChIKey WNMONLFBVHNRQS-OVWBIBOFSA-N
Formula C30H36O7
HBA 7
HBD 2
MW 508.61
Rotatable Bonds 3
TPSA 110.13
LogP 3.52
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 508.25
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Warionia saharae Asteraceae Plantae 40727

Showing of synonyms

  • Hilmi F, Gertsch J, et al. (2003). Cytotoxic versus anti-inflammatory effects in HeLa, Jurkat T and human peripheral blood cells caused by guaianolide-type sesquiterpene lactones. Bioorganic and Medicinal Chemistry,2003,11,3659-3663. [View] [PubMed]
Pubchem: 162911069
Nmrshiftdb2: 70111665

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)C=CC(C12)CCC(C2)C(=C)C(=O)OC(C3)CC(C=34)C5C(C(=C)C(=O)O5)CCC4

Level: 1

Mol. Weight: 508.61 g/mol

Structure

SMILES: C1CCC(C(=C)C(=O)O2)C2C(C1=3)CCC3

Level: 0

Mol. Weight: 508.61 g/mol

Structure

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

Level: 0

Mol. Weight: 508.61 g/mol

Anti-inflammatory
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.100
Plasma Protein Binding
86.05
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.370
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.150
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.710
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
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
-694.300
Rat (Acute)
4.360
Rat (Chronic Oral)
2.240
Fathead Minnow
4.370
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
464.820
Hydration Free Energy
-2.900
Log(D) at pH=7.4
3.310
Log(P)
2.98
Log S
-4.91
Log(Vapor Pressure)
-9.14
Melting Point
204.16
pKa Acid
7.23
pKa Basic
3.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7724
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7724
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7669
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7669
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7319
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7319
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7306
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7306

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