Anchinopeptolide A - Compound Card

Anchinopeptolide A

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Anchinopeptolide A

Structure
Zoomed Structure
  • Family: Animalia - Anchinoidae
  • Kingdom: Animalia
  • Class: Alkaloid
    • Subclass: Dimeric Peptide Alkaloid
Canonical Smiles NC(=N)NCC[C@H]1[C@](O)(C(=O)N[C@H](C(=O)N/C=C/c2ccc(cc2)O)C)N(C(=O)[C@]1(O)CCCNC(=N)N)[C@H](C(=O)N/C=C/c1ccc(cc1)O)C
InChI InChI=1S/C34H46N10O8/c1-20(27(47)39-17-12-22-4-8-24(45)9-5-22)43-29(49)34(52)26(14-19-42-32(37)38)33(51,15-3-16-41-31(35)36)30(50)44(34)21(2)28(48)40-18-13-23-6-10-25(46)11-7-23/h4-13,17-18,20-21,26,45-46,51-52H,3,14-16,19H2,1-2H3,(H,39,47)(H,40,48)(H,43,49)(H4,35,36,41)(H4,37,38,42)/b17-12+,18-13+/t20-,21-,26+,33-,34-/m0/s1
InChIKey HCBLDZZFUFWBIT-NCVYMDLJSA-N
Formula C34H46N10O8
HBA 10
HBD 13
MW 722.8
Rotatable Bonds 16
TPSA 312.33
LogP -1.12
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 52
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 722.35
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Anchinoe tenacior Anchinoidae Animalia 252958

Showing of synonyms

  • Casapullo A, Finamore E, et al. (1993). A dimeric peptide alkaloid of a completely new type, anchinopeptolide A, from the marine sponge Anchinoe tenacior. Tetrahedron Letters,1993,34(39),6297-6300. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CNC(=O)CNC(=O)C(CCC2=O)N2CC(=O)NC=Cc3ccccc3

Level: 4

Mol. Weight: 722.8 g/mol

Structure

SMILES: O=C1CCC(N1)C(=O)NCC(=O)NC=Cc2ccccc2

Level: 1

Mol. Weight: 722.8 g/mol

Structure

SMILES: O=C1CCCN1CC(=O)NC=Cc2ccccc2

Level: 1

Mol. Weight: 722.8 g/mol

Structure

SMILES: O=C1CCCN1

Level: 0

Mol. Weight: 722.8 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 722.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.24
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.130
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
290.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.600
Plasma Protein Binding
63.39
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
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
2.460
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-4.830
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.780
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.100
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
-511269.800
Rat (Acute)
2.460
Rat (Chronic Oral)
1.270
Fathead Minnow
654.310
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
46672.130
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-0.570
Log(P)
1.3
Log S
-0.26
Log(Vapor Pressure)
-1573.46
Melting Point
159.92
pKa Acid
4.02
pKa Basic
10.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9168
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9168
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8987
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8987
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8798
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8798
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7965
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7965
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7954
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7954
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7922
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7922
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7781
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7781
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7710
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7710
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7611
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7611
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7512
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7512
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7485
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7485
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7442
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7442
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7439
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7439
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7435
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7435
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7401
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7401
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7327
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7327
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7315
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7315
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7313
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7313
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7305
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7305
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7291
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7291
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7276
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7276
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7274
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7274
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7273
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7273
Chaperone protein ClpB Q9RA63 CLPB_THET8 Thermus thermophilus 3 0.7271
Chaperone protein ClpB Q9RA63 CLPB_THET8 Thermus thermophilus 3 0.7271
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7270
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7270
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7270
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7270
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7258
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7258
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7236
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7236
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7234
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7234
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7226
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7226
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7219
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7219
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7215
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7215
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7207
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7207
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7202
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7202
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7173
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7173
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7159
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7159
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7154
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7154
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7142
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7142
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7141
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7141
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7140
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7140
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7140
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7140
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7129
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7129
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7118
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7118
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7109
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7109
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7102
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7102
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7101
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7101
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7097
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7097
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7096
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7096
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7093
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7093
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7074
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7074
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7065
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7065
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7062
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7062
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7061
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7061
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7054
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7047
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7047
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7033
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7033
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7032
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7032
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7032
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7032
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7031
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7031
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7030
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7030
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7021
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7021
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7016
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7016
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7015
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7015
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7014
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7014
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007

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