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Latrunculin B

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\CC/C(=C\C(=O)O2)/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
InChIKey	NSHPHXHGRHSMIK-JRIKCGFMSA-N
Formula	C₂₀H₂₉NO₅S
HBA	6
HBD	2
MW	395.52
Rotatable Bonds	1
TPSA	84.86
LogP	3.3
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.7
Exact Mass	395.18
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Negombata magnifica	Podospongiidae	Animalia	344322
2	Negombata magnifica	Podospongiidae	Animalia	344322

Showing of synonyms

El Sayed KA, Youssef DT, et al. (2006). Bioactive natural and semisynthetic latrunculins. Journal of Natural Products,2006,69(2),219-223. [View] [PubMed]
Sayed KA, Khanfar MA, et al. (2008). Latrunculin A and its C-17-O-carbamates inhibit prostate tumor cell invasion and HIF-1 activation in breast tumor cells. Journal of Natural Products,2008,71(3),396-402. [View] [PubMed]

Pubchem: 6436219

Cas: 76343-94-7

Zinc: ZINC000005751767

Chebi: 49703

Nmrshiftdb2: 60027877

Metabolights: MTBLC49703

Chembl: CHEMBL411879

Comptox: DTXSID10881387

Drugbank: DB08080

Pdb Ligand: LAB

Bindingdb: 50508923

CPRiL: 63632

SMILES: O=C1NC(CS1)C(CC23)OC(C2)CCCC=CCCC=CC(=O)O3

Level: 1

Mol. Weight: 395.52 g/mol

SMILES: C1COC(CC12)CCCC=CCCC=CC(=O)O2

Level: 0

Mol. Weight: 395.52 g/mol

SMILES: O=C1NCCS1

Level: 0

Mol. Weight: 395.52 g/mol

Antimicrobial

Antimigratory

Antitumor

Absorption

Caco-2 (logPapp): -4.73
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.83
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.9
Plasma Protein Binding: 53.6
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: 5.07
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.04
Biodegradation: Safe
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: 4.79
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: -8.61
Rat (Acute): 2.35
Rat (Chronic Oral): 1.64
Fathead Minnow: 3.81
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: 446.6
Hydration Free Energy: -7.7
Log(D) at pH=7.4: 2.84
Log(P): 2.67
Log S: -4.05
Log(Vapor Pressure): -8.59
Melting Point: 149.82
pKa Acid: 8.43
pKa Basic: 5.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8656
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8656
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8396
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8396
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8239
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8239
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	4	0.8172
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	4	0.8172
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7665
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7665
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7416
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7416
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7233
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7233
Regulatory protein SdiA	P07026	SDIA_ECOLI	Escherichia coli	4	0.7209
Regulatory protein SdiA	P07026	SDIA_ECOLI	Escherichia coli	4	0.7209
Actin, alpha skeletal muscle	P68134	ACTS_MOUSE	Mus musculus	3	0.7180
Actin, alpha skeletal muscle	P68134	ACTS_MOUSE	Mus musculus	3	0.7180
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7047
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7047

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