17-O-[N-(Phenyl)carbamoyl]latrunculin A - Compound Card

17-O-[N-(Phenyl)carbamoyl]latrunculin A

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17-O-[N-(Phenyl)carbamoyl]latrunculin A

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Polyketide
    • Subclass: Macrolide
Canonical Smiles O=C(O[C@]1(O[C@@H]2CC[C@H](C)/C=C\C=C\CC/C(=C\C(=O)O[C@@H](C1)C2)/C)[C@@H]1CSC(=O)N1)Nc1ccccc1
InChI InChI=1S/C29H36N2O6S/c1-20-10-6-3-4-7-11-21(2)16-26(32)35-24-17-23(15-14-20)36-29(18-24,25-19-38-28(34)31-25)37-27(33)30-22-12-8-5-9-13-22/h3-6,8-10,12-13,16,20,23-25H,7,11,14-15,17-19H2,1-2H3,(H,30,33)(H,31,34)/b4-3+,10-6-,21-16-/t20-,23-,24-,25+,29+/m1/s1
InChIKey AJLVAOHKVXQLIG-WOZHBFIZSA-N
Formula C29H36N2O6S
HBA 7
HBD 2
MW 540.68
Rotatable Bonds 3
TPSA 102.96
LogP 6.12
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 540.23
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Negombata magnifica Podospongiidae Animalia 344322

Showing of synonyms

  • 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: 24853748
Nmrshiftdb2: 60076716

No compound-protein relationship available.

Structure

SMILES: c1ccccc1NC(=O)OC(CC23)(C(CS4)NC4=O)OC(C2)CCCC=CC=CCCC=CC(=O)O3

Level: 2

Mol. Weight: 540.68 g/mol

Structure

SMILES: c1ccccc1NC(=O)OC(C2)OC(CC23)CCCC=CC=CCCC=CC(=O)O3

Level: 1

Mol. Weight: 540.68 g/mol

Structure

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

Level: 1

Mol. Weight: 540.68 g/mol

Structure

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

Level: 0

Mol. Weight: 540.68 g/mol

Structure

SMILES: O=C1NCCS1

Level: 0

Mol. Weight: 540.68 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 540.68 g/mol

Antitumor

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.48
Plasma Protein Binding
98.92
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.01
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.73
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
-1764.49
Rat (Acute)
2.43
Rat (Chronic Oral)
1.7
Fathead Minnow
9.12
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
499.75
Hydration Free Energy
-2.92
Log(D) at pH=7.4
4.17
Log(P)
4.46
Log S
-5.28
Log(Vapor Pressure)
-9.11
Melting Point
161.33
pKa Acid
8.65
pKa Basic
6.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8445
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8445
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7980
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7980
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7662
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7662
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7440
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7440
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7362
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7362
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7311
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7311

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