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N-hydroxymethyllatrunculin B
- Family: Animalia - Podospongiidae
- Kingdom: Animalia
-
Class: Polyketide
- Subclass: Macrolide
| Canonical Smiles | OCN1C(=O)SC[C@H]1[C@@]1(O)C[C@H]2C[C@H](O1)CC[C@H](C)/C=C\CC/C(=C\C(=O)O2)/C |
|---|---|
| InChI | InChI=1S/C21H31NO6S/c1-14-5-3-4-6-15(2)9-19(24)27-17-10-16(8-7-14)28-21(26,11-17)18-12-29-20(25)22(18)13-23/h3,5,9,14,16-18,23,26H,4,6-8,10-13H2,1-2H3/b5-3-,15-9-/t14-,16-,17-,18+,21-/m1/s1 |
| InChIKey | OFLWPNGXBLYXIX-LDYNUQMTSA-N |
| Formula | C21H31NO6S |
| HBA | 7 |
| HBD | 2 |
| MW | 425.55 |
| Rotatable Bonds | 2 |
| TPSA | 96.3 |
| LogP | 2.97 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.71 |
| Exact Mass | 425.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Negombata magnifica | Podospongiidae | Animalia | 344322 |
Showing of synonyms
N-hydroxymethyllatrunculin B
(4R)-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)-3-(hydroxymethyl)-1,3-thiazolidin-2-one
(4R)-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]-3-(hydroxymethyl)-1,3-thiazolidin-2-one
CHEMBL491355
(4R)-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]-3-(hydroxymethyl)thiazolidin-2-one
(4R)-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]-3-(hydroxymethyl)-1,3-thiazolidin-2-one
No compound-protein relationship available.
SMILES: O=C1NC(CS1)C(CC23)OC(C2)CCCC=CCCC=CC(=O)O3
Level: 1
Mol. Weight: 425.55 g/mol
SMILES: C1COC(CC12)CCCC=CCCC=CC(=O)O2
Level: 0
Mol. Weight: 425.55 g/mol
SMILES: O=C1NCCS1
Level: 0
Mol. Weight: 425.55 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.71
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.85
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.94
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.89
- Plasma Protein Binding
- 56.31
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.01
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.43
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.12
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.89
- 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
- -18.1
- Rat (Acute)
- 2.32
- Rat (Chronic Oral)
- 1.9
- Fathead Minnow
- 3.87
- 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
- 466.4
- Hydration Free Energy
- -7.32
- Log(D) at pH=7.4
- 2.51
- Log(P)
- 2.71
- Log S
- -3.51
- Log(Vapor Pressure)
- -9.47
- Melting Point
- 133.9
- pKa Acid
- 7.99
- pKa Basic
- 5.85
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.9095 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.9095 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7892 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7892 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7780 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7780 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7571 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7571 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7479 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7479 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7286 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7286 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.7253 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.7253 |
| Lysosomal acid glucosylceramidase | P04062 | GLCM_HUMAN | Homo sapiens | 3 | 0.7067 |
| Lysosomal acid glucosylceramidase | P04062 | GLCM_HUMAN | Homo sapiens | 3 | 0.7067 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7033 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7033 |