Sibthorpine - Compound Card

Sibthorpine

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Sibthorpine

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC[C@@]1(O)C(=O)O[C@H]2[C@H]1CCC(=C)[C@H]1[C@@H]2C(=C)[C@@H](C1)O
InChI InChI=1S/C15H20O5/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h9-13,16-17,19H,1-6H2/t9-,10+,11+,12-,13-,15-/m0/s1
InChIKey LWOZDCFSMDBOSA-WJLGXSQGSA-N
Formula C15H20O5
HBA 5
HBD 3
MW 280.32
Rotatable Bonds 1
TPSA 86.99
LogP 0.15
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 280.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cynara sibthorpiana Asteraceae Plantae 935151

Showing of synonyms

  • Omar A, Sarg TA, et al. (1984). Guaianolides from Cynara sibthorpiana. Phytochemistry,1984,23(10),2381-2382. [View]
Pubchem: 101320294
Nmrshiftdb2: 70093721

No compound-protein relationship available.

Structure

SMILES: C=C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 280.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
49.23
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
4.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.14
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.62
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.02
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
-1.28
Rat (Acute)
3.34
Rat (Chronic Oral)
2.3
Fathead Minnow
3.97
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
365.77
Hydration Free Energy
-11.66
Log(D) at pH=7.4
0.4
Log(P)
0.49
Log S
-1.77
Log(Vapor Pressure)
-8.54
Melting Point
170.87
pKa Acid
6.69
pKa Basic
5.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8240
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8240
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8204
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8204
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7284
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7284

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