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N-acetyllatrunculin B
- Family: Animalia - Podospongiidae
- Kingdom: Animalia
-
Class: Polyketide
- Subclass: Macrolide
| Canonical Smiles | C/C/1=C/C(=O)O[C@@H]2C[C@@H](CC[C@@H](/C=C\CC1)C)O[C@@](C2)(O)[C@@H]1CSC(=O)N1C(=O)C |
|---|---|
| InChI | InChI=1S/C22H31NO6S/c1-14-6-4-5-7-15(2)10-20(25)28-18-11-17(9-8-14)29-22(27,12-18)19-13-30-21(26)23(19)16(3)24/h4,6,10,14,17-19,27H,5,7-9,11-13H2,1-3H3/b6-4-,15-10-/t14-,17-,18-,19+,22-/m1/s1 |
| InChIKey | LNEREMNREKXZQC-ITIRMEDBSA-N |
| Formula | C22H31NO6S |
| HBA | 7 |
| HBD | 1 |
| MW | 437.56 |
| Rotatable Bonds | 1 |
| TPSA | 93.14 |
| LogP | 3.56 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.68 |
| Exact Mass | 437.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Negombata magnifica | Podospongiidae | Animalia | 344322 |
Showing of synonyms
N-acetyllatrunculin B
(4R)-3-acetyl-4-((1R,4S,5Z,9Z,13R,15R)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo(11.3.1)heptadeca-5,9-dien-15-yl)-1,3-thiazolidin-2-one
(4R)-3-acetyl-4-((1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo(11.3.1)heptadeca-4,8-dien-15-yl)-1,3-thiazolidin-2-one
(4R)-3-acetyl-4-[(1R,4S,5Z,9Z,13R,15R)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]-1,3-thiazolidin-2-one
(4R)-3-acetyl-4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one
CHEMBL491161
(4R)-3-acetyl-4-[(1R,4S,5Z,9Z,13R,15R)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]thiazolidin-2-one
2-Thiazolidinone, 3-acetyl-4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-, (4R)-
No compound-protein relationship available.
SMILES: O=C1NC(CS1)C(CC23)OC(C2)CCCC=CCCC=CC(=O)O3
Level: 1
Mol. Weight: 437.56 g/mol
SMILES: C1COC(CC12)CCCC=CCCC=CC(=O)O2
Level: 0
Mol. Weight: 437.56 g/mol
SMILES: O=C1NCCS1
Level: 0
Mol. Weight: 437.56 g/mol
Antimicrobial
Antimigratory
Absorption
- Caco-2 (logPapp)
- -4.74
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.74
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.03
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.88
- Plasma Protein Binding
- 62.4
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.34
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.76
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.63
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.72
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -25.36
- Rat (Acute)
- 2.36
- Rat (Chronic Oral)
- 1.96
- Fathead Minnow
- 3.92
- 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
- 438.88
- Hydration Free Energy
- -4.46
- Log(D) at pH=7.4
- 2.43
- Log(P)
- 3.56
- Log S
- -4.5
- Log(Vapor Pressure)
- -8.43
- Melting Point
- 126.03
- pKa Acid
- 8.77
- pKa Basic
- 5.09
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9760 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9760 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.9116 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.9116 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8704 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8704 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7741 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7741 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7705 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7705 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7246 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7246 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7218 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7218 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7152 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7152 |