Anchinopeptolide A - Compound Card

Anchinopeptolide A

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Anchinopeptolide A

Structure
Zoomed Structure
  • Family: Animalia - Hymedesmiidae
  • Kingdom: Animalia
  • Class: Alkaloid
    • Subclass: Peptide Alkaloid
Canonical Smiles NC(=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)CCCN=C(N)N)[C@H](C(=O)N/C=C\c1ccc(cc1)O)C)N
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-CTIRTUGVSA-N
Formula C34H46N10O8
HBA 10
HBD 11
MW 722.8
Rotatable Bonds 16
TPSA 317.33
LogP -1.54
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 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]
Pubchem: 101017457
Nmrshiftdb2: 60045915

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

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
-4.680
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
285.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.660
Plasma Protein Binding
61.33
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
3.010
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-4.260
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
8.330
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
-511268.290
Rat (Acute)
2.710
Rat (Chronic Oral)
1.670
Fathead Minnow
653.650
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
47912.550
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-0.120
Log(P)
-0.97
Log S
-1.33
Log(Vapor Pressure)
-1617.72
Melting Point
191.13
pKa Acid
4.35
pKa Basic
11.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9660
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9660
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9508
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9508
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9188
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9188
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9172
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9172
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.9136
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.9136
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9030
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9030
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8940
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8940
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8551
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8551
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8236
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8236
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8177
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8177
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8040
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8040
Probable nicotinate-nucleotide adenylyltransferase C3L5T6 NADD_BACAC Bacillus anthracis 3 0.7861
Probable nicotinate-nucleotide adenylyltransferase C3L5T6 NADD_BACAC Bacillus anthracis 3 0.7861
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7790
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7790
Purine nucleoside phosphorylase Q9BMI9 Q9BMI9_SCHMA Schistosoma mansoni 3 0.7715
Purine nucleoside phosphorylase Q9BMI9 Q9BMI9_SCHMA Schistosoma mansoni 3 0.7715
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7693
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7693
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7629
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7629
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7568
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7568
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7566
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7566
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7558
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7558
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7539
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7539
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7524
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7524
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7510
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7510
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7465
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7465
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7443
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7443
Copper-transporting ATPase Q97UU7 Q97UU7_SACS2 Saccharolobus solfataricus 4 0.7391
Copper-transporting ATPase Q97UU7 Q97UU7_SACS2 Saccharolobus solfataricus 4 0.7391
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7344
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7344
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7333
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7333
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7311
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7311
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7310
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7310
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7285
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7285
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7272
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7272
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7247
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7247
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7247
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7247
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7245
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7245
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
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 4 0.7232
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 4 0.7232
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7222
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7222
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7212
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7212
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7210
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7210
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7204
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7204
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7200
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7200
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7191
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7191
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7167
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7167
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7166
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7166
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7166
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7166
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7163
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7163
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7162
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7162
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7158
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7158
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7149
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7149
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7147
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7147
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7135
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7135
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7134
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7134
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7129
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7129
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7116
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7116
Chaperone protein ClpB Q9RA63 CLPB_THET8 Thermus thermophilus 3 0.7108
Chaperone protein ClpB Q9RA63 CLPB_THET8 Thermus thermophilus 3 0.7108
adenine phosphoribosyltransferase Q967M2 Q967M2_GIAIN Giardia intestinalis 2 0.7105
adenine phosphoribosyltransferase Q967M2 Q967M2_GIAIN Giardia intestinalis 2 0.7105
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7095
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7095
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7083
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7083
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7078
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7078
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 2 0.7067
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 2 0.7067
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7059
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7059
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7052
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7052
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7043
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7043
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7042
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7042
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7030
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7030
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7026
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7026
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7025
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7025
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7025
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7025
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7011
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7011
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7008
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7008
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7003
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7003
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7002
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7002

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