(3S,4R,5S)-4-hydroxy-5-methyl-3-(130-phenyl-10-n-tridecyl)-butanolide - Compound Card

(3S,4R,5S)-4-hydroxy-5-methyl-3-(130-phenyl-10-n-tridecyl)-butanolide

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(3S,4R,5S)-4-hydroxy-5-methyl-3-(130-phenyl-10-n-tridecyl)-butanolide

Structure
Zoomed Structure
  • Family: Plantae - Lauraceae
  • Kingdom: Plantae
  • Class: Glycoside
Canonical Smiles C[C@@H]1OC(=O)[C@H]([C@H]1O)CCCCCCCCCCCCCc1ccccc1
InChI InChI=1S/C24H38O3/c1-20-23(25)22(24(26)27-20)19-15-10-8-6-4-2-3-5-7-9-12-16-21-17-13-11-14-18-21/h11,13-14,17-18,20,22-23,25H,2-10,12,15-16,19H2,1H3/t20-,22-,23-/m0/s1
InChIKey PBJHEIRFTYGACF-PMVMPFDFSA-N
Formula C24H38O3
HBA 3
HBD 1
MW 374.56
Rotatable Bonds 14
TPSA 46.53
LogP 5.83
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 374.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Beilschmiedia obscura Lauraceae Plantae 88849

Showing of synonyms

  • Waleguele CC, Mba'ning BM, et al. (2020). Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae). Molecules. 2020, 25(12), 2862. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCC(C1=O)CCCCCCCCCCCCCc2ccccc2

Level: 1

Mol. Weight: 374.56 g/mol

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 374.56 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 374.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.12
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.95
Plasma Protein Binding
86.44
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-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
3.36
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.18
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.7
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.22
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
-2.31
Rat (Acute)
1.94
Rat (Chronic Oral)
2.41
Fathead Minnow
4.25
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
445.46
Hydration Free Energy
-5.4
Log(D) at pH=7.4
4.75
Log(P)
7.15
Log S
-5.59
Log(Vapor Pressure)
-8.59
Melting Point
79.82
pKa Acid
9.96
pKa Basic
5.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.9252
Peridinin-chlorophyll a protein, high-salt form O76183 O76183_AMPCA Amphidinium carterae 3 0.8748
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8740
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8438
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7899
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7742
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7631
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7581
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7563
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7501
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7484
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7466
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7379
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7353
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7335
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7325
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7277
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7261
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7236
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7215
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7212
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7165
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7126
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7116
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7110
Heat shock cognate 71 kDa protein P11142 HSP7C_HUMAN Homo sapiens 2 0.7109
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7089
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7083
Metallophosphoesterase A3DJ38 A3DJ38_HUNT2 Clostridium thermocellum 2 0.7061
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7019

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