(2S,3S,4R,2’R,9E)-[2’-hydroxytetraeicosanoyl]-2-aminooctadec-9-ene-1,3,4-triol - Compound Card

(2S,3S,4R,2’R,9E)-[2’-hydroxytetraeicosanoyl]-2-aminooctadec-9-ene-1,3,4-triol

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(2S,3S,4R,2’R,9E)-[2’-hydroxytetraeicosanoyl]-2-aminooctadec-9-ene-1,3,4-triol

Structure
Zoomed Structure
  • Family: Plantae - Primulaceae
  • Kingdom: Plantae
  • Class: Fatty Alcohol
Canonical Smiles CCCCCCCCCCCCCC[C@H](C(=O)N[C@H]([C@@H](CCCCC/C=C/CCCCCCCC)O)CO)O
InChI InChI=1S/C34H67NO4/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-32(37)31(30-36)35-34(39)33(38)29-27-25-23-21-18-16-14-12-10-8-6-4-2/h17,19,31-33,36-38H,3-16,18,20-30H2,1-2H3,(H,35,39)/b19-17+/t31-,32+,33+/m0/s1
InChIKey BBRIOHLRVCBZKX-PEIIVYKSSA-N
Formula C34H67NO4
HBA 4
HBD 4
MW 553.91
Rotatable Bonds 30
TPSA 89.79
LogP 8.53
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.91
Exact Mass 553.51
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Maesa lanceolata Primulaceae Plantae 992730

Showing of synonyms

  • Seumo AS, Nanfack ARD, et al. (2022). Alkenylbenzoquinones and other compounds from the fruit of Maesa lanceolata exhibited potent cytotoxic, antibacterial, and antiradical scavenging activities.. Natural product research,2022, 36(17), 4379-4387. [View] [PubMed]

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.36
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.72
Plasma Protein Binding
64.59
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
-0.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.84
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
4.59
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
-1208.57
Rat (Acute)
1.93
Rat (Chronic Oral)
3.44
Fathead Minnow
6.62
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
483.01
Hydration Free Energy
-2.9
Log(D) at pH=7.4
4.95
Log(P)
11.24
Log S
-6.3
Log(Vapor Pressure)
-10.62
Melting Point
79.5
pKa Acid
9.24
pKa Basic
4.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9474
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9202
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9081
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9072
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.9032
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.8830
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.8806
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8746
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8651
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.8625
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.8621
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.8486
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8467
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.8380
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8355
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8231
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.8159
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.8113
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8110
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8085
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.8044
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7953
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.7948
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7850
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7755
Regucalcin Q64374 RGN_MOUSE Mus musculus 3 0.7706
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7676
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7672
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7666
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7519
Peridinin-chlorophyll a protein, high-salt form O76183 O76183_AMPCA Amphidinium carterae 2 0.7490
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7458
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7334
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 4 0.7295
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7263
Procathepsin L P07711 CATL1_HUMAN Homo sapiens 4 0.7192
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7103
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7036
Conserved hypthetical protein Q8GGP1 Q8GGP1_STRAZ Streptomyces atroolivaceus 3 0.7023

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