(5S)-3-[(3E,5S)-5-Hydroxy-3-hepten-6-yn-1-yl]-5-methyl2(5H)-furanone - Compound Card

(5S)-3-[(3E,5S)-5-Hydroxy-3-hepten-6-yn-1-yl]-5-methyl2(5H)-furanone

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(5S)-3-[(3E,5S)-5-Hydroxy-3-hepten-6-yn-1-yl]-5-methyl2(5H)-furanone

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles C[C@@H]1OC(=O)C(=C1)CC/C=C/[C@@H](C#C)O
InChI InChI=1S/C12H14O3/c1-3-11(13)7-5-4-6-10-8-9(2)15-12(10)14/h1,5,7-9,11,13H,4,6H2,2H3/b7-5+/t9-,11+/m0/s1
InChIKey HXDXTMOGRXPNNT-ACFJMREFSA-N
Formula C12H14O3
HBA 3
HBD 1
MW 206.24
Rotatable Bonds 4
TPSA 46.53
LogP 1.19
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 206.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton trocheliophorum Alcyoniidae Animalia 205097

Showing of synonyms

  • Gomaa M.N, Soliman K, et al. (2015). Antibacterial effect of the red sea soft coral Sarcophyton trocheliophorum. Natural Product Research, 2015, 30(6), 729–734.. [View] [PubMed]
Pubchem: 10352939
Nmrshiftdb2: 70023942

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 206.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.87
Plasma Protein Binding
38.87
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
-0.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.13
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-2.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.46
Micronucleos
Toxic
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
-1.72
Rat (Acute)
2.66
Rat (Chronic Oral)
1.72
Fathead Minnow
4.23
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
297.27
Hydration Free Energy
-7.34
Log(D) at pH=7.4
1.27
Log(P)
1.0
Log S
-1.41
Log(Vapor Pressure)
-5.17
Melting Point
63.3
pKa Acid
8.18
pKa Basic
4.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9577
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9516
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9409
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9293
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8862
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8665
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8398
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8109
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7907
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7871
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7615
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7602
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7591
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7559
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7545
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7522
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7484
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7450
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7445
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7341
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7341
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7313
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7309
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7308
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7257
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7240
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7193
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7191
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7126
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7112
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7111
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7086
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7073
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7027
Alanine aminotransferase Q9P9M8 Q9P9M8_9EURY Pyrococcus furiosus 2 0.7004

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