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15-O-octyllatrunculin B

Family: Animalia - Podospongiidae
Kingdom: Animalia
Class: Polyketide
- Subclass: Macrolide

Canonical Smiles	CCCCCCCCO[C@]1(O[C@@H]2CC[C@H](C)/C=C\CC/C(=C\C(=O)O[C@@H](C1)C2)/C)[C@@H]1CSC(=O)N1
InChI	InChI=1S/C28H45NO5S/c1-4-5-6-7-8-11-16-32-28(25-20-35-27(31)29-25)19-24-18-23(34-28)15-14-21(2)12-9-10-13-22(3)17-26(30)33-24/h9,12,17,21,23-25H,4-8,10-11,13-16,18-20H2,1-3H3,(H,29,31)/b12-9-,22-17-/t21-,23-,24-,25+,28-/m1/s1
InChIKey	VZIJRUYGPMQTFM-JLQOQYJLSA-N
Formula	C₂₈H₄₅NO₅S
HBA	6
HBD	1
MW	507.74
Rotatable Bonds	9
TPSA	73.86
LogP	6.69
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.79
Exact Mass	507.3
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	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]

Pubchem: 11540713

Zinc: ZINC000049878228

Nmrshiftdb2: 60055169

Chembl: CHEMBL490517

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 507.74 g/mol

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

Level: 0

Mol. Weight: 507.74 g/mol

SMILES: O=C1NCCS1

Level: 0

Mol. Weight: 507.74 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp): -4.81
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.77
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.32
Plasma Protein Binding: 88.96
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-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: 3.35
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.81
Biodegradation: Toxic
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: Toxic
Daphnia Maga: 5.9
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: -340.77
Rat (Acute): 2.32
Rat (Chronic Oral): 1.77
Fathead Minnow: 4.49
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: 498.19
Hydration Free Energy: -2.88
Log(D) at pH=7.4: 4.82
Log(P): 6.49
Log S: -5.5
Log(Vapor Pressure): -8.87
Melting Point: 75.36
pKa Acid: 9.27
pKa Basic: 4.92

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8410
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8410
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7908
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7908
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7862
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7862
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7737
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7737
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7456
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7456
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7437
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7437
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7312
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7312
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7170
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7170
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7118
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7118
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7077
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7077
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7030
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7030

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