17-O-[N-(2-Bromoethyl)carbamoyl]latrunculin A - Compound Card

17-O-[N-(2-Bromoethyl)carbamoyl]latrunculin A

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17-O-[N-(2-Bromoethyl)carbamoyl]latrunculin A

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Polyketide
    • Subclass: Macrolide
Canonical Smiles BrCCNC(=O)O[C@@]1(C[C@@H]2OC(=O)/C=C(/C)\CC/C=C/C=C\[C@H](CC[C@@H](O1)C2)C)[C@@H]1CSC(=O)N1
InChI InChI=1S/C25H35BrN2O6S/c1-17-7-5-3-4-6-8-18(2)13-22(29)32-20-14-19(10-9-17)33-25(15-20,21-16-35-24(31)28-21)34-23(30)27-12-11-26/h3-5,7,13,17,19-21H,6,8-12,14-16H2,1-2H3,(H,27,30)(H,28,31)/b4-3+,7-5-,18-13-/t17-,19-,20-,21+,25+/m1/s1
InChIKey ZPHSMQHQJGJQEQ-ODVPECJOSA-N
Formula C25H35BrN2O6S
HBA 7
HBD 2
MW 571.53
Rotatable Bonds 4
TPSA 102.96
LogP 4.99
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 570.14
Number of Lipinski Rule Violations 1
# 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: 24853809
Nmrshiftdb2: 60076718

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 571.53 g/mol

Structure

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

Level: 0

Mol. Weight: 571.53 g/mol

Structure

SMILES: O=C1NCCS1

Level: 0

Mol. Weight: 571.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.03
Plasma Protein Binding
79.51
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.18
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.65
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.66
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-299.62
Rat (Acute)
3.17
Rat (Chronic Oral)
1.43
Fathead Minnow
4.41
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
494.05
Hydration Free Energy
-2.79
Log(D) at pH=7.4
3.59
Log(P)
3.7
Log S
-5.45
Log(Vapor Pressure)
-8.94
Melting Point
106.09
pKa Acid
7.1
pKa Basic
6.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9355
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9355
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8978
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8978
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7766
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7766
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7561
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7561
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7459
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7459
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7343
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7343

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