(R)-20-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxypentacosan-2-yl]nonadecanamide - Compound Card

(R)-20-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxypentacosan-2-yl]nonadecanamide

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(R)-20-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxypentacosan-2-yl]nonadecanamide

Structure
Zoomed Structure
  • Family: Alcyoniidae
  • Kingdom: Animalia
  • Class: Ceramide
Canonical Smiles CCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H]([C@@H](CCCCCCCCCCCCCCC[C@@H](CCCCC)O)O)O)CO
InChI InChI=1S/C44H89NO5/c1-3-5-7-8-9-10-11-12-13-14-18-21-24-27-30-34-38-43(49)45-41(39-46)44(50)42(48)37-33-29-26-23-20-17-15-16-19-22-25-28-32-36-40(47)35-31-6-4-2/h40-42,44,46-48,50H,3-39H2,1-2H3,(H,45,49)/t40-,41+,42-,44+/m1/s1
InChIKey AJPPZRXWZRUURX-RLWYSASNSA-N
Formula C44H89NO5
HBA 5
HBD 5
MW 712.2
Rotatable Bonds 41
TPSA 110.02
LogP 11.63
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 50
Formal Charge 0
Fraction CSP3 0.98
Exact Mass 711.67
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Sinularia candidula Alcyoniidae Animalia 3286459

Showing of synonyms

  • Ahmed S, Ibrahim A and Arafa AS. (2013). Anti-H5N1 virus metabolites from the Red Sea soft coral, Sinularia candidula. Tetrahedron Letters,2013,54(19),2377-2381. [View]
Pubchem: 163024895
Nmrshiftdb2: 70091020

No compound-protein relationship available.

No scaffolds available.

Antiviral

Absorption

Caco-2 (logPapp)
-5.37
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.12
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
121.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.9
Plasma Protein Binding
72.6
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
1.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.43
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.3
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
4.52
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
-227016.76
Rat (Acute)
1.95
Rat (Chronic Oral)
3.79
Fathead Minnow
298.86
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
23531.21
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.9
Log(P)
15.45
Log S
-7.1
Log(Vapor Pressure)
-695.9
Melting Point
98.93
pKa Acid
9.39
pKa Basic
3.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9334
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9334
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9291
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9291
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9092
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9092
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.9063
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.9063
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9000
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9000
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8867
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8867
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8856
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8856
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8798
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8798
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8702
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8702
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.8567
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.8567
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8351
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8351
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.8130
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.8130
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8033
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8033
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7768
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7768
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7605
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7605
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7589
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7589
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7563
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7563
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7537
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7537
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7492
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7492
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7486
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7486
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7434
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7434
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7410
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7410
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 2 0.7399
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 2 0.7399
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7384
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7384
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7371
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7371
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7347
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7347
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7344
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7344
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7338
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7338
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7335
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7335
Actin, alpha skeletal muscle P68134 ACTS_MOUSE Mus musculus 4 0.7332
Actin, alpha skeletal muscle P68134 ACTS_MOUSE Mus musculus 4 0.7332
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7310
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7310
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7309
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7309
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7308
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7308
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7304
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7304
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7290
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7290
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7287
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7287
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7280
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7280
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7279
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7279
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.7275
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.7275
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7266
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7266
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7242
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7242
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7237
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7237
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.7233
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.7233
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7206
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7206
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7194
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7194
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7183
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7183
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7169
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7169
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7166
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7166
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.7160
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 4 0.7160
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7150
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7150
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 2 0.7137
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 2 0.7137
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 3 0.7119
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 3 0.7119
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7075
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7075
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 2 0.7049
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 2 0.7049
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7048
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7048
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7013
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7013

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