14-hydroxyhypocretenolide - Compound Card

14-hydroxyhypocretenolide

Select a section from the left sidebar

14-hydroxyhypocretenolide

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(=C)C(=O)O3)C
InChI InChI=1S/C15H16O4/c1-8-5-12(17)13-11(7-16)4-3-10-6-15(8,13)19-14(18)9(10)2/h5,10,16H,2-4,6-7H2,1H3/t10-,15+/m1/s1
InChIKey SPZKJZJNPQNEKT-BMIGLBTASA-N
Formula C15H16O4
HBA 4
HBD 1
MW 260.29
Rotatable Bonds 1
TPSA 63.6
LogP 1.46
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 260.1
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: 15378302
Nmrshiftdb2: 70029327

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(C2)CCC=C(C123)C(=O)C=C3

Level: 0

Mol. Weight: 260.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
48.33
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
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
7.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.08
Micronucleos
Toxic
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
0.09
Rat (Acute)
2.68
Rat (Chronic Oral)
1.92
Fathead Minnow
3.94
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
348.03
Hydration Free Energy
-8.73
Log(D) at pH=7.4
0.75
Log(P)
1.37
Log S
-2.34
Log(Vapor Pressure)
-6.31
Melting Point
133.69
pKa Acid
7.27
pKa Basic
5.69
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 0.7725
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7725
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7585
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7585
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7527
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7527
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7429
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7429
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7421
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7421

Download SDF