NAV

Latrunculin B

Identification

Generic Name
Latrunculin B
DrugBank Accession Number
DB08080
Background

Latrunculin B is a 14-membered macrolide attached to 2-thiazolidinone moiety, isolated from Red Sea sponge Latrunculia magnifica.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 395.513
Monoisotopic: 395.176643733
Chemical Formula
C20H29NO5S
Synonyms
  • (+)-latrunculin B
  • LAT-B
External IDs
  • NSC-339663
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UActin, alpha skeletal muscleNot AvailableHumans
UMKL/myocardin-like protein 1Not AvailableHumans
UProtein spire homolog 2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolides and analogues
Sub Class
Not Available
Direct Parent
Macrolides and analogues
Alternative Parents
Oxanes / Thiazolidines / Enoate esters / Thiocarbamic acid derivatives / Organic carbonic acids and derivatives / Lactones / Hemiacetals / Oxacyclic compounds / Monocarboxylic acids and derivatives / Azacyclic compounds
show 5 more
Substituents
Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Azacycle / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Enoate ester / Hemiacetal / Hydrocarbon derivative
show 14 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cyclic hemiketal, macrolide, oxabicycloalkane, thiazolidinone (CHEBI:49703)
Affected organisms
Not Available

Chemical Identifiers

UNII
LW7U308U7U
CAS number
76343-94-7
InChI Key
NSHPHXHGRHSMIK-JRIKCGFMSA-N
InChI
InChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23)/b5-3-,14-9-/t13-,15-,16-,17+,20-/m1/s1
IUPAC Name
(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]-1,3-thiazolidin-2-one
SMILES
[H][C@]1(CSC(=O)N1)[C@@]1(O)C[C@H]2C[C@@H](CC[C@H](C)\C=C/CC\C(C)=C/C(=O)O2)O1

References

General References
Not Available
PubChem Compound
6436219
PubChem Substance
99444551
ChemSpider
10192733
ChEBI
49703
ChEMBL
CHEMBL411879
ZINC
ZINC000005751767
PDBe Ligand
LAB
Wikipedia
Latrunculin
PDB Entries
2q0u / 2v51 / 2v52 / 2yje / 2yjf / 3mn5 / 4b1u / 4b1v / 4b1w / 4b1x …
show 16 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0713 mg/mLALOGPS
logP1.98ALOGPS
logP3.79Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.36Chemaxon
pKa (Strongest Basic)-4.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area84.86 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity105.64 m3·mol-1Chemaxon
Polarizability42.08 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9326
Blood Brain Barrier-0.6164
Caco-2 permeable-0.6528
P-glycoprotein substrateSubstrate0.7551
P-glycoprotein inhibitor INon-inhibitor0.9337
P-glycoprotein inhibitor IINon-inhibitor0.9835
Renal organic cation transporterNon-inhibitor0.9164
CYP450 2C9 substrateNon-substrate0.8888
CYP450 2D6 substrateNon-substrate0.7955
CYP450 3A4 substrateSubstrate0.6295
CYP450 1A2 substrateNon-inhibitor0.7519
CYP450 2C9 inhibitorNon-inhibitor0.8065
CYP450 2D6 inhibitorNon-inhibitor0.9166
CYP450 2C19 inhibitorNon-inhibitor0.7339
CYP450 3A4 inhibitorNon-inhibitor0.9353
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8956
Ames testNon AMES toxic0.6894
CarcinogenicityNon-carcinogens0.9643
BiodegradationNot ready biodegradable0.8779
Rat acute toxicity2.7374 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9832
hERG inhibition (predictor II)Non-inhibitor0.9064
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ue9-2592000000-c9f0d689a268c3ff1dae
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-0019000000-775e76ff46c51f2fa803
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0049000000-b384ea43b3471ebbac54
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-0159000000-973a14b972849c707cc9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-9026000000-a6871f1c10bfd81d0cf5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0umr-0294000000-a72b255c5e1bf99d3db3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f8c-9377000000-61d7e3c41fb50a74bf1e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-194.6729183
predicted
DarkChem Lite v0.1.0
[M-H]-202.56776
predicted
DeepCCS 1.0 (2019)
[M+H]+191.5691183
predicted
DarkChem Lite v0.1.0
[M+H]+204.46315
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.0162183
predicted
DarkChem Lite v0.1.0
[M+Na]+210.14783
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Actin, alpha skeletal muscle
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Structural constituent of cytoskeleton
Specific Function
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name
ACTA1
Uniprot ID
P68133
Uniprot Name
Actin, alpha skeletal muscle
Molecular Weight
42050.67 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. MKL/myocardin-like protein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription regulatory region sequence-specific dna binding
Specific Function
Transcriptional coactivator of serum response factor (SRF) with the potential to modulate SRF target genes. Suppresses TNF-induced cell death by inhibiting activation of caspases; its transcription...
Gene Name
MKL1
Uniprot ID
Q969V6
Uniprot Name
MKL/myocardin-like protein 1
Molecular Weight
98917.94 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details3. Protein spire homolog 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Acts as an actin nucleation factor, remains associated with the slow-growing pointed end of the new filament. Involved in intracellular vesicle transport along actin fibers, providing a novel link ...
Gene Name
SPIRE2
Uniprot ID
Q8WWL2
Uniprot Name
Protein spire homolog 2
Molecular Weight
79669.945 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:28 / Updated at June 12, 2020 16:52