Anchinopeptolide C - Compound Card

Anchinopeptolide C

Select a section from the left sidebar

Anchinopeptolide C

Structure
Zoomed Structure
  • Family: Animalia - Hymedesmiidae
  • Kingdom: Animalia
  • Class: Alkaloid
    • Subclass: Peptide Alkaloid
Canonical Smiles Oc1ccc(cc1)/C=C/NC(=O)CN1C(=O)[C@]([C@H]([C@]1(O)C(=O)N[C@H](C(=O)N/C=C/c1ccc(cc1)O)C)CCN=C(N)N)(O)CCCN=C(N)N
InChI InChI=1S/C33H44N10O8/c1-20(27(47)39-17-12-22-5-9-24(45)10-6-22)42-28(48)33(51)25(13-18-41-31(36)37)32(50,14-2-15-40-30(34)35)29(49)43(33)19-26(46)38-16-11-21-3-7-23(44)8-4-21/h3-12,16-17,20,25,44-45,50-51H,2,13-15,18-19H2,1H3,(H,38,46)(H,39,47)(H,42,48)(H4,34,35,40)(H4,36,37,41)/b16-11+,17-12+/t20-,25+,32-,33-/m0/s1
InChIKey HTEZSPDIMAAWRF-FWUIFEAPSA-N
Formula C33H44N10O8
HBA 10
HBD 11
MW 708.78
Rotatable Bonds 16
TPSA 317.33
LogP -1.93
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 51
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 708.33
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Anchinoe tenacior Hymedesmiidae Animalia 252958

Showing of synonyms

  • Casapullo A, Minale L, et al. (1994). Four new dimeric peptide alkaloids, anchinopeptolides B-D, and cycloanchinopeptolide C, congeners of anchinopeptolide A, from the mediterranean marine sponge Anchinoe tenacior. Journal of Natural Products,1994,57(9),1227-1233. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 4

Mol. Weight: 708.78 g/mol

Structure

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

Level: 1

Mol. Weight: 708.78 g/mol

Structure

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

Level: 1

Mol. Weight: 708.78 g/mol

Structure

SMILES: O=C1CCCN1

Level: 0

Mol. Weight: 708.78 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 708.78 g/mol

Binding assays against the following receptors
Human b2 bradykinin and neuropeptide gamma receptors
Somatostatin

Absorption

Caco-2 (logPapp)
-6.52
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.330
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
187.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.640
Plasma Protein Binding
57.41
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.140
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.780
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.200
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
-333431.150
Rat (Acute)
2.660
Rat (Chronic Oral)
1.670
Fathead Minnow
430.510
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
27538.900
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-0.450
Log(P)
-1.29
Log S
-1.32
Log(Vapor Pressure)
-969.97
Melting Point
208.67
pKa Acid
4.7
pKa Basic
11.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.9073
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.9073
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8959
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8959
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8922
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8922
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8736
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8736
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8576
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8576
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8415
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8415
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8227
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8227
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8137
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8137
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8049
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8049
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8027
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8027
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7998
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7998
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7995
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7995
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7985
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7985
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7884
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7884
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7692
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7692
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7664
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7664
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7604
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7604
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7543
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7543
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7535
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7535
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7440
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7440
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.7411
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.7411
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7402
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7402
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7400
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7400
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7398
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7398
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7365
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7365
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7327
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7327
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7316
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7316
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7301
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7301
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
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7277
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7277
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7270
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7270
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7261
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7261
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7261
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7261
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7256
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7256
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7232
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7232
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7220
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7220
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7220
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7220
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7217
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7217
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7210
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7210
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7209
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7209
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7207
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7207
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7190
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7190
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7167
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7167
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7165
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7165
Chaperone protein ClpB Q9RA63 CLPB_THET8 Thermus thermophilus 3 0.7161
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7161
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7161
Chaperone protein ClpB Q9RA63 CLPB_THET8 Thermus thermophilus 3 0.7161
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7153
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7153
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7141
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7141
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7134
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7134
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7131
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7131
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7113
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7113
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7110
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7110
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7109
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7109
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7104
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7104
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7096
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7096
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7096
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7096
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7093
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 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 0.7060
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7060
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7057
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7057
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7056
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7056
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7053
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7053
adenine phosphoribosyltransferase Q967M2 Q967M2_GIAIN Giardia intestinalis 2 0.7051
adenine phosphoribosyltransferase Q967M2 Q967M2_GIAIN Giardia intestinalis 2 0.7051
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7050
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7050
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7048
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7048
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7046
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7046
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7039
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7039
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7030
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7030
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7021
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7021
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7019
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7019
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7017
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7017
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7015
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7015
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7012
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7012
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7010
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7010
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7009
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7009
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7008
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7008
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007

Download SDF