ANPDB

Select a section from the left sidebar

Anchinopeptolide B

Family: Animalia - Hymedesmiidae
Kingdom: Animalia
Class: Alkaloid
- Subclass: Peptide Alkaloid

Canonical Smiles	O=C(CNC(=O)[C@]1(O)N([C@H](C(=O)N/C=C/c2ccc(cc2)O)C)C(=O)[C@]([C@H]1CCN=C(N)N)(O)CCCN=C(N)N)N/C=C/c1ccc(cc1)O
InChI	InChI=1S/C33H44N10O8/c1-20(27(47)39-17-12-22-5-9-24(45)10-6-22)43-29(49)32(50,14-2-15-40-30(34)35)25(13-18-41-31(36)37)33(43,51)28(48)42-19-26(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	UWVIWDAQDJDWOC-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]

Pubchem: 10032723

Cas: 160041-36-1

Zinc: ZINC000049898891

Nmrshiftdb2: 60045923

Chembl: CHEMBL508317

No compound-protein relationship available.

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

Level: 4

Mol. Weight: 708.78 g/mol

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

Level: 1

Mol. Weight: 708.78 g/mol

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

Level: 1

Mol. Weight: 708.78 g/mol

SMILES: O=C1CCCN1

Level: 0

Mol. Weight: 708.78 g/mol

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): -6.55
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.21
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 192.92

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.57
Plasma Protein Binding: 55.25
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: 2.97
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.47
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.03
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.21
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: -344187.69
Rat (Acute): 2.74
Rat (Chronic Oral): 1.68
Fathead Minnow: 444.16
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: 28643.17
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.51
Log(P): -1.33
Log S: -1.34
Log(Vapor Pressure): -1010.49
Melting Point: 228.98
pKa Acid: 4.45
pKa Basic: 11.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8926
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8926
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.8866
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.8866
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8456
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8456
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8209
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8209
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8161
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8161
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8134
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8134
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8126
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8126
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8081
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8081
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8032
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8032
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7822
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7822
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7652
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7652
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7641
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7641
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7533
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7533
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	0.7482
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7482
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7445
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7445
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7400
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7400
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7392
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7392
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7367
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7367
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7348
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7348
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7317
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7317
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7310
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7310
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7308
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7308
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7308
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7308
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7307
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7307
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7285
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7285
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7285
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7285
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7260
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7260
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7247
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7247
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7224
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7224
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7222
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7222
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7213
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7213
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7208
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7208
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7208
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7208
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7204
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7204
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7184
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7184
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7179
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7179
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7175
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7175
Cobalt-precorrin-4 C(11)-methyltransferase	O87696	CBIF_BACME	Priestia megaterium	3	0.7172
Cobalt-precorrin-4 C(11)-methyltransferase	O87696	CBIF_BACME	Priestia megaterium	3	0.7172
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7166
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7166
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7158
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7158
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	2	0.7149
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7149
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7149
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	2	0.7149
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7132
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7132
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7129
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7129
adenine phosphoribosyltransferase	Q967M2	Q967M2_GIAIN	Giardia intestinalis	2	0.7128
adenine phosphoribosyltransferase	Q967M2	Q967M2_GIAIN	Giardia intestinalis	2	0.7128
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7126
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7126
Chaperone protein ClpB	Q9RA63	CLPB_THET8	Thermus thermophilus	3	0.7124
Chaperone protein ClpB	Q9RA63	CLPB_THET8	Thermus thermophilus	3	0.7124
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7121
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7121
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7121
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7121
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7120
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7120
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7093
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7093
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7092
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7092
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7088
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7088
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7073
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7073
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7063
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7063
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7060
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7060
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7060
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7060
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7055
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7055
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7054
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7054
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7049
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7049
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
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7025
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7025
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
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7015
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7015
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7014
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7014
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7014
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7014
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7014
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7014
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7008
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7008
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7006
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7006

Download SDF