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15-O-butyllatrunculin B
- Family: Animalia - Podospongiidae
- Kingdom: Animalia
-
Class: Polyketide
- Subclass: Macrolide
| Canonical Smiles | CCCCO[C@@]1(C[C@@H]2OC(=O)/C=C(/C)\CC/C=C\[C@H](CC[C@@H](O1)C2)C)[C@@H]1CSC(=O)N1 |
|---|---|
| InChI | InChI=1S/C24H37NO5S/c1-4-5-12-28-24(21-16-31-23(27)25-21)15-20-14-19(30-24)11-10-17(2)8-6-7-9-18(3)13-22(26)29-20/h6,8,13,17,19-21H,4-5,7,9-12,14-16H2,1-3H3,(H,25,27)/b8-6-,18-13-/t17-,19-,20-,21+,24-/m1/s1 |
| InChIKey | FLXXYAPFRVVUIF-LOJUFBAJSA-N |
| Formula | C24H37NO5S |
| HBA | 6 |
| HBD | 1 |
| MW | 451.63 |
| Rotatable Bonds | 5 |
| TPSA | 73.86 |
| LogP | 5.13 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 451.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Negombata magnifica | Podospongiidae | Animalia | 344322 |
Showing of synonyms
15-O-butyllatrunculin B
(4R)-4-((1R,4S,5Z,9Z,13R,15R)-15-butoxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo(11.3.1)heptadeca-5,9-dien-15-yl)-1,3-thiazolidin-2-one
(4R)-4-((1R,4Z,8Z,10S,13R,15R)-15-butoxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo(11.3.1)heptadeca-4,8-dien-15-yl)-1,3-thiazolidin-2-one
(4R)-4-[(1R,4S,5Z,9Z,13R,15R)-15-butoxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]-1,3-thiazolidin-2-one
(4R)-4-[(1R,4Z,8Z,10S,13R,15R)-15-butoxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one
CHEMBL522801
(4R)-4-[(1R,4S,5Z,9Z,13R,15R)-15-butoxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]thiazolidin-2-one
2-Thiazolidinone, 4-[(1R,4Z,8Z,10S,13R,15R)-15-butoxy-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: 451.63 g/mol
SMILES: C1COC(CC12)CCCC=CCCC=CC(=O)O2
Level: 0
Mol. Weight: 451.63 g/mol
SMILES: O=C1NCCS1
Level: 0
Mol. Weight: 451.63 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
- -2.4
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.05
- Plasma Protein Binding
- 70.39
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.27
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.9
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.18
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.57
- 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
- -50.16
- Rat (Acute)
- 2.25
- Rat (Chronic Oral)
- 1.53
- Fathead Minnow
- 3.96
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 467.05
- Hydration Free Energy
- -2.86
- Log(D) at pH=7.4
- 4.09
- Log(P)
- 4.55
- Log S
- -5.11
- Log(Vapor Pressure)
- -8.21
- Melting Point
- 87.93
- pKa Acid
- 8.98
- pKa Basic
- 5.09
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.8377 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.8377 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7819 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7819 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7774 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7774 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7529 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7529 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7476 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7476 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7348 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7348 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7191 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7191 |