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Latrunculin A
- Family: Animalia - Podospongiidae
- Kingdom: Animalia
-
Class: Polyketide
- Subclass: Macrolide
| Canonical Smiles | O=C1SC[C@H](N1)[C@@]1(O)C[C@H]2C[C@H](O1)CC[C@H](C)/C=C\C=C\CC/C(=C\C(=O)O2)/C |
|---|---|
| InChI | InChI=1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/b4-3+,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1 |
| InChIKey | DDVBPZROPPMBLW-IZGXTMSKSA-N |
| Formula | C22H31NO5S |
| HBA | 6 |
| HBD | 2 |
| MW | 421.56 |
| Rotatable Bonds | 1 |
| TPSA | 84.86 |
| LogP | 3.86 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.64 |
| Exact Mass | 421.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Negombata magnifica | Podospongiidae | Animalia | 344322 |
Showing of synonyms
Latrunculin A
LAT-A
76343-93-6
(+)-latrunculin A
NSC 613011
UNII-SRQ9WWM084
SRQ9WWM084
LATRUNCULIN
CHEBI:69136
(4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
NSC-613011
LATRUNCULIN A [MI]
DTXSID90893488
2-Thiazolidinone, 4-((1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo(13.3.1)nonadeca-4,8,10-trien-17-yl)-, (4R)-
2-Thiazolidinone, 4-(17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo(13.3.1)nonadeca-4,8,10-trien-17-yl)-, (1R*,4Z,8E,10Z,12S*,15R*,17R*(R*))-(+)-
2-THIAZOLIDINONE, 4-(17-HYDROXY-5,12-DIMETHYL-3-OXO-2,16-DIOXABICYCLO(13.3.1)NONADECA-4,8,10-TRIEN-17-YL)-, (1R-(1R*,4Z,8E,10Z,12S*,15R*,17R*(R*)))-
(4R)-4-((1R,4Z,8E,10Z,12R,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo(13.3.1)nonadeca-4,8,10-trien-17-yl)-1,3-thiazolidin-2-one
(4R)-4-((1R,4Z,8E,10Z,12S,15R,17R)-17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo(13.3.1)nonadeca-4,8,10-trien-17-yl)-1,3-thiazolidin-2-one
(4R)-4-[(1R,4S,5Z,7E,11Z,15R,17R)-17-hydroxy-4,11-dimethyl-13-oxo-14,18-dioxabicyclo[13.3.1]nonadeca-5,7,11-trien-17-yl]-1,3-thiazolidin-2-one
(4R)-4-[(1R,4Z,8E,10Z,12R,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
(4S)-4-((1R,4Z,8E,10Z,12R,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo(13.3.1)nonadeca-4,8,10-trien-17-yl)-1,3-thiazolidin-2-one
(4S)-4-[(1R,4Z,8E,10Z,12R,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
2-Thiazolidinone, 4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-, (4R)-
DTXCID501323505
(4R)-4-((1R,4S,5Z,7E,11Z,15R,17R)-17-hydroxy-4,11-dimethyl-13-oxo-14,18-dioxabicyclo(13.3.1)nonadeca-5,7,11-trien-17-yl)-1,3-thiazolidin-2-one
LatA
NSC613011
(R)-4-((1R,4Z,8E,10Z,12S,15R,17R)-17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)thiazolidin-2-one
CHEMBL404116
SCHEMBL12998892
BDBM65515
DDVBPZROPPMBLW-IZGXTMSKSA-N
Latrunculin A, Latrunculia magnifica
HB0375
AKOS024457907
DB02621
HY-16929
CS-0012976
Q4255014
(4R)-4-[(1R,4S,5Z,7E,11Z,15R,17R)-17-hydroxy-4,11-dimethyl-13-oxo-14,18-dioxabicyclo[13.3.1]nonadeca-5,7,11-trien-17-yl]thiazolidin-2-one
2-Thiazolidinone,12-dimethyl-3-oxo-2,16- dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)-, [1R-[1R*,4Z,8E,10Z,12S*,15R*,17R*(R*)]]-
Pubchem:
445420
Cas:
76343-93-6
Zinc:
ZINC000005766575
Chebi:
69136
Nmrshiftdb2:
60060909
Metabolights:
MTBLC69136
Chembl:
CHEMBL404116
Comptox:
DTXSID90893488
Drugbank:
DB02621
Pdb Ligand:
LAR
Bindingdb:
65515
CPRiL:
56684
SMILES: O=C1NC(CS1)C(CC23)OC(C2)CCCC=CC=CCCC=CC(=O)O3
Level: 1
Mol. Weight: 421.56 g/mol
SMILES: C1COC(CC12)CCCC=CC=CCCC=CC(=O)O2
Level: 0
Mol. Weight: 421.56 g/mol
SMILES: O=C1NCCS1
Level: 0
Mol. Weight: 421.56 g/mol
Antitumor
Absorption
- Caco-2 (logPapp)
- -4.72
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.83
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.34
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.05
- Plasma Protein Binding
- 64.95
- 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
- 4.53
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.19
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.15
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.37
- 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
- -18.76
- Rat (Acute)
- 2.32
- Rat (Chronic Oral)
- 1.73
- 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
- 469.62
- Hydration Free Energy
- -5.75
- Log(D) at pH=7.4
- 3.38
- Log(P)
- 3.12
- Log S
- -4.37
- Log(Vapor Pressure)
- -8.99
- Melting Point
- 161.3
- pKa Acid
- 8.44
- pKa Basic
- 5.68
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.9591 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.9591 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.8426 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.8426 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8351 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8351 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8235 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8235 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.8215 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.8215 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8200 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8200 |
| Actin, alpha skeletal muscle | P68134 | ACTS_MOUSE | Mus musculus | 3 | 0.7297 |
| Actin, alpha skeletal muscle | P68134 | ACTS_MOUSE | Mus musculus | 3 | 0.7297 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7251 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7251 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7132 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7132 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7112 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7112 |