(R)-4-hydroxyeleutherin - Compound Card

(R)-4-hydroxyeleutherin

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(R)-4-hydroxyeleutherin

Structure
Zoomed Structure
  • Family: Plantae - Iridaceae
  • Kingdom: Plantae
  • Class: Polyketide
Canonical Smiles COc1cccc2c1C(=O)C1=C(C2=O)[C@H]([C@@H](O[C@@H]1C)C)O
InChI InChI=1S/C16H16O5/c1-7-11-13(14(17)8(2)21-7)15(18)9-5-4-6-10(20-3)12(9)16(11)19/h4-8,14,17H,1-3H3/t7-,8+,14+/m1/s1
InChIKey WKNIPFDPSCAKRN-KXEKKFMESA-N
Formula C16H16O5
HBA 5
HBD 1
MW 288.3
Rotatable Bonds 1
TPSA 72.83
LogP 1.54
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 288.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Eleutherine bulbosa Iridaceae Plantae 1210469

Showing of synonyms

  • Gallo FR, Palazzino G, et al. (2010). Polyketides from Eleutherine bulbosa.. Natural product research,2010, 24(16), 1578-1586. [View] [PubMed]
Pubchem: 162993454
Nmrshiftdb2: 70032405

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)C3=C(C2=O)CCOC3

Level: 0

Mol. Weight: 288.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.860
Plasma Protein Binding
64.43
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
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
4.410
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.260
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.980
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.820
Micronucleos
Toxic
NR-AhR
Toxic
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
1.350
Rat (Acute)
3.210
Rat (Chronic Oral)
2.620
Fathead Minnow
4.070
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
383.120
Hydration Free Energy
-10.120
Log(D) at pH=7.4
1.300
Log(P)
2.13
Log S
-3.01
Log(Vapor Pressure)
-6.33
Melting Point
154.82
pKa Acid
6.3
pKa Basic
3.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8802
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8366
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8076
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7775
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7437
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7302
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7271
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7190
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7160
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7085
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7064
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7064

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