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

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

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

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Polyketide
    • Subclass: Macrolide
Canonical Smiles C[C@@H]1/C=C\C=C\CC/C(=C\C(=O)O[C@@H]2C[C@@H](CC1)O[C@@](C2)(OC(=O)NCc1ccccc1)[C@@H]1CSC(=O)N1)/C
InChI InChI=1S/C30H38N2O6S/c1-21-10-6-3-4-7-11-22(2)16-27(33)36-25-17-24(15-14-21)37-30(18-25,26-20-39-29(35)32-26)38-28(34)31-19-23-12-8-5-9-13-23/h3-6,8-10,12-13,16,21,24-26H,7,11,14-15,17-20H2,1-2H3,(H,31,34)(H,32,35)/b4-3+,10-6-,22-16-/t21-,24-,25-,26+,30+/m1/s1
InChIKey KNDBQBZVXDCVTR-JRNQGUQKSA-N
Formula C30H38N2O6S
HBA 7
HBD 2
MW 554.71
Rotatable Bonds 4
TPSA 102.96
LogP 5.79
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 554.25
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: 24853811
Nmrshiftdb2: 60076720
Bindingdb: 50478377

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CNC(=O)OC(CC23)(C(CS4)NC4=O)OC(C2)CCCC=CC=CCCC=CC(=O)O3

Level: 2

Mol. Weight: 554.71 g/mol

Structure

SMILES: c1ccccc1CNC(=O)OC(C2)OC(CC23)CCCC=CC=CCCC=CC(=O)O3

Level: 1

Mol. Weight: 554.71 g/mol

Structure

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

Level: 1

Mol. Weight: 554.71 g/mol

Structure

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

Level: 0

Mol. Weight: 554.71 g/mol

Structure

SMILES: O=C1NCCS1

Level: 0

Mol. Weight: 554.71 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 554.71 g/mol

Antitumor

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.79
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.76
Plasma Protein Binding
100.75
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
3.4
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.06
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.86
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
Toxic
T. Pyriformis
-2940.22
Rat (Acute)
2.72
Rat (Chronic Oral)
1.76
Fathead Minnow
12.95
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
462.61
Hydration Free Energy
-2.94
Log(D) at pH=7.4
4.42
Log(P)
4.23
Log S
-5.43
Log(Vapor Pressure)
-8.66
Melting Point
136.71
pKa Acid
7.52
pKa Basic
6.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.9423
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.9423
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8874
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8874
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8765
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8765
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8703
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8703
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8651
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8651
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8644
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8644
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8430
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8430
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.8412
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.8412
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8346
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8346
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8090
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8090
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7964
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7964
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7786
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7786
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7706
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7706
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7689
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7689
Purine nucleoside phosphorylase P50389 PNPH_SACS2 Saccharolobus solfataricus 3 0.7573
Purine nucleoside phosphorylase P50389 PNPH_SACS2 Saccharolobus solfataricus 3 0.7573
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7507
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7507
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7469
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7469
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7449
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7449
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7381
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7381
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7365
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7365
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7339
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7339
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7335
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7335
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7329
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7329
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7321
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7321
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7296
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7296
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7267
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7267
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7241
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7241
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7241
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7241
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7235
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7235
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7214
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7214
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7196
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7196
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7177
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7177
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7149
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7149
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7140
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7140
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 2 0.7115
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 2 0.7115
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7114
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7114
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7104
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7104
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7091
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7091
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7091
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7091
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7087
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7087
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7077
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 2 0.7077
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 2 0.7077
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7077
Seed lectin subunit I P05045 LEC1_VIGUC Vigna unguiculata subsp. cylindrica 2 0.7072
Seed lectin subunit I P05045 LEC1_VIGUC Vigna unguiculata subsp. cylindrica 2 0.7072
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7071
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7071
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7060
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7060
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7031
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7031
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7023
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7023
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7005
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7005
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7003
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7003
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7000
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7000

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