Epiloliolide - Compound Card

Epiloliolide

Select a section from the left sidebar

Epiloliolide

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzofuran
Canonical Smiles O[C@@H]1C[C@]2(C)OC(=O)C=C2C(C1)(C)C
InChI InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11-/m0/s1
InChIKey XEVQXKKKAVVSMW-CPCISQLKSA-N
Formula C11H16O3
HBA 3
HBD 1
MW 196.25
Rotatable Bonds 0
TPSA 46.53
LogP 1.41
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 196.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lampranthus spectabilis Aizoaceae Plantae 188836
2 Heliotropium bacciferum Boraginaceae Plantae 244092

Showing of synonyms

  • Aïssaoui H, Mencherini T, et al. (2019). Heliotropium bacciferum Forssk. (Boraginaceae) extracts: chemical constituents, antioxidant activity and cytotoxic effect in human cancer cell lines. Natural product research, 2019, 33(12), 1813-1818. [View] [PubMed]
  • Samy M. N, Khalil H. E, et al. (2018). Phytoconstituents from the aerial parts of Lampranthus spectabilis. South African Journal of Botany, 2018, 118, 179–182. [View]
Pubchem: 11019783
Nmrshiftdb2: 60021694
CPRiL: 450058
Structure

SMILES: C1C(=O)OC(C=12)CCCC2

Level: 0

Mol. Weight: 196.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.03
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
Penetrable
Fraction Unbound (Human)
0.24
Plasma Protein Binding
29.34
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.44
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.35
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.06
Micronucleos
Safe
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
-1.04
Rat (Acute)
1.86
Rat (Chronic Oral)
1.53
Fathead Minnow
3.59
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
269.88
Hydration Free Energy
-6.14
Log(D) at pH=7.4
1.22
Log(P)
0.53
Log S
-1.5
Log(Vapor Pressure)
-2.51
Melting Point
94.67
pKa Acid
9.66
pKa Basic
4.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7320
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7217
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7187
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7177
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7159
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7035
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7020

Download SDF