17-O-[N-(3-Chloropropyl)carbamoyl]latrunculin A - Compound Card

17-O-[N-(3-Chloropropyl)carbamoyl]latrunculin A

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17-O-[N-(3-Chloropropyl)carbamoyl]latrunculin A

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Polyketide
    • Subclass: Macrolide
Canonical Smiles ClCCCNC(=O)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
InChI InChI=1S/C26H37ClN2O6S/c1-18-8-5-3-4-6-9-19(2)14-23(30)33-21-15-20(11-10-18)34-26(16-21,22-17-36-25(32)29-22)35-24(31)28-13-7-12-27/h3-5,8,14,18,20-22H,6-7,9-13,15-17H2,1-2H3,(H,28,31)(H,29,32)/b4-3+,8-5-,19-14-/t18-,20-,21-,22+,26+/m1/s1
InChIKey ZBKZGKOPNVIOTD-QUIXEILKSA-N
Formula C26H37ClN2O6S
HBA 7
HBD 2
MW 541.11
Rotatable Bonds 5
TPSA 102.96
LogP 5.22
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 540.21
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: 24853810
Nmrshiftdb2: 60076717

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 541.11 g/mol

Structure

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

Level: 0

Mol. Weight: 541.11 g/mol

Structure

SMILES: O=C1NCCS1

Level: 0

Mol. Weight: 541.11 g/mol

Antitumor

Absorption

Caco-2 (logPapp)
-5.0
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.37
Plasma Protein Binding
76.55
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
3.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.57
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.83
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.6
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
-484.08
Rat (Acute)
2.79
Rat (Chronic Oral)
1.67
Fathead Minnow
4.81
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
498.39
Hydration Free Energy
-2.94
Log(D) at pH=7.4
3.74
Log(P)
3.63
Log S
-4.8
Log(Vapor Pressure)
-9.05
Melting Point
118.02
pKa Acid
7.09
pKa Basic
6.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7124
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7124
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7018
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7018

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