14-hydroxy-11,13-dihydrohypocretenolide - Compound Card

14-hydroxy-11,13-dihydrohypocretenolide

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14-hydroxy-11,13-dihydrohypocretenolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2C(=O)C=C([C@]32C[C@@H](CC1)[C@H](C(=O)O3)C)C
InChI InChI=1S/C15H18O4/c1-8-5-12(17)13-11(7-16)4-3-10-6-15(8,13)19-14(18)9(10)2/h5,9-10,16H,3-4,6-7H2,1-2H3/t9-,10-,15+/m1/s1
InChIKey JMNFCQSRPSOEKG-FCHSOHFDSA-N
Formula C15H18O4
HBA 4
HBD 1
MW 262.3
Rotatable Bonds 1
TPSA 63.6
LogP 1.54
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 262.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hedypnois cretica Asteraceae Plantae 268036

Showing of synonyms

  • Harraz FM, Kassem FF, et al. (1988). Hypnocretenolide derivatives from Hedypnois cretica. Phytochemistry,1988,27,6,1866-1867. [View]
Pubchem: 162952963
Nmrshiftdb2: 70029324

No compound-protein relationship available.

Structure

SMILES: C1=CC(=O)C(C123)=CCCC(C2)CC(=O)O3

Level: 0

Mol. Weight: 262.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.34
Plasma Protein Binding
44.66
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
5.75
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.23
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.16
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.44
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.38
Rat (Acute)
2.56
Rat (Chronic Oral)
2.06
Fathead Minnow
3.92
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
347.79
Hydration Free Energy
-8.52
Log(D) at pH=7.4
0.54
Log(P)
1.46
Log S
-2.0
Log(Vapor Pressure)
-5.92
Melting Point
138.31
pKa Acid
8.55
pKa Basic
5.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7897
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7897
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7477
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7477
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7167
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7167
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7096
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7096

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