latrunculin B

Details

• Internal ID: 074b8ab9-0723-494f-b1f8-b1716e6a27d2
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• 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 (Canonical): CC1CCC2CC(CC(O2)(C3CSC(=O)N3)O)OC(=O)C=C(CCC=C1)C
• SMILES (Isomeric): C[C@H]/1CC[C@@H]2C[C@H](C[C@@](O2)([C@@H]3CSC(=O)N3)O)OC(=O)/C=C(\CC/C=C1)/C
• 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
• InChI Key: NSHPHXHGRHSMIK-JRIKCGFMSA-N
• Popularity: 1,139 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₉NO₅S
• Molecular Weight: 395.50 g/mol
• Exact Mass: 395.17664420 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• LAT-B
• 76343-94-7
• (+)-latrunculin B
• LW7U308U7U
• CHEBI:49703
• INS-115644
• NSC-339663
• INS115644
• (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
• 2-Thiazolidinone, 4-(15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo(11.3.1)heptadeca-4,8-dien-15-yl)-, (1R*,4Z,8Z,10S*,13R*,15R*(R*))-(+)-
• DTXSID10881387
• (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
• RefChem:152464
• DTXCID201022649
• 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)-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
• (4S)-4-((1R,4Z,8Z,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
• 4-((1R,4Z,8Z,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
• NSC 339663
• UNII-LW7U308U7U
• latrunculin-B
• NSC339663
• NSHPHXHGRHSMIK-JRIKCGFMSA-N
• 2-THIAZOLIDINONE, 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)-
• 2-Thiazolidinone, 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)-
• Lat B
• Latrunculin B from Latruncula magnifica
• LATRUNCULIN B [MI]
• BSPBio_001189
• CHEMBL411879
• SCHEMBL2531366
• BCBcMAP01_000226
• HMS1362K11
• HMS1792K11
• HMS1990K11
• HMS3403K11
• BDA34394
• LAT-B; NSC 339663
• BDBM50508923
• MFCD00270879
• AKOS032947159
• DB08080
• IDI1_002180
• SMP2_000317
• NCGC00163459-03
• AS-83262
• DA-49463
• HY-101848
• CS-0022006
• Q4255012
• BRD-K30455030-001-03-3
• BRD-K61292460-001-02-3
• Latrunculin B from Latruncula magnifica, >=80% (HPLC), solid
• (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]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]thiazolidin-2-one
• 2-THIAZOLIDINONE, 4-(15-HYDROXY-5,10-DIMETHYL-3-OXO-2,14-DIOXABICYCLO(11.3.1)HEPTADECA-4,8-DIEN-15-YL)-, (1R-(1R*,4Z,8Z,10S*,13R*,15R*(R*)))-
• 2-Thiazolidinone,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)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9383	93.83%
Caco-2	-	0.6042	60.42%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6824	68.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9049	90.49%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9250	92.50%
P-glycoprotein inhibitior	-	0.6593	65.93%
P-glycoprotein substrate	+	0.5100	51.00%
CYP3A4 substrate	+	0.6416	64.16%
CYP2C9 substrate	-	0.5998	59.98%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.9353	93.53%
CYP2C9 inhibition	-	0.8065	80.65%
CYP2C19 inhibition	-	0.7339	73.39%
CYP2D6 inhibition	-	0.9166	91.66%
CYP1A2 inhibition	-	0.7519	75.19%
CYP2C8 inhibition	-	0.6860	68.60%
CYP inhibitory promiscuity	-	0.8956	89.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5503	55.03%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9941	99.41%
Skin irritation	-	0.7451	74.51%
Skin corrosion	-	0.9165	91.65%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3892	38.92%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.6119	61.19%
skin sensitisation	-	0.8293	82.93%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8034	80.34%
Nephrotoxicity	-	0.6824	68.24%
Acute Oral Toxicity (c)	III	0.5542	55.42%
Estrogen receptor binding	+	0.8124	81.24%
Androgen receptor binding	+	0.5805	58.05%
Thyroid receptor binding	+	0.5351	53.51%
Glucocorticoid receptor binding	+	0.7324	73.24%
Aromatase binding	-	0.5060	50.60%
PPAR gamma	+	0.6948	69.48%
Honey bee toxicity	-	0.8201	82.01%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9575	95.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.01%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.30%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.98%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.10%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.76%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	91.75%	89.63%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.44%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.45%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.76%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.40%	89.00%
CHEMBL1871	P10275	Androgen Receptor	84.78%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.05%	92.94%
CHEMBL4208	P20618	Proteasome component C5	83.65%	90.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.32%	85.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.51%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6436219
• LOTUS: LTS0150176
• wikiData: Q4255012