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Anchinopeptolide D

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

Canonical Smiles	O=C(CNC(=O)[C@]1(O)N(CC(=O)N/C=C/c2ccc(cc2)O)C(=O)[C@]([C@H]1CCN=C(N)N)(O)CCCN=C(N)N)N/C=C/c1ccc(cc1)O
InChI	InChI=1S/C32H42N10O8/c33-29(34)39-14-1-13-31(49)24(12-17-40-30(35)36)32(50,27(47)41-18-25(45)37-15-10-20-2-6-22(43)7-3-20)42(28(31)48)19-26(46)38-16-11-21-4-8-23(44)9-5-21/h2-11,15-16,24,43-44,49-50H,1,12-14,17-19H2,(H,37,45)(H,38,46)(H,41,47)(H4,33,34,39)(H4,35,36,40)/b15-10+,16-11+/t24-,31+,32+/m1/s1
InChIKey	BBMGZUODZUGTGP-YKYMCWODSA-N
Formula	C₃₂H₄₂N₁₀O₈
HBA	10
HBD	11
MW	694.75
Rotatable Bonds	16
TPSA	317.33
LogP	-2.32
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	50
Formal Charge	0
Fraction CSP3	0.31
Exact Mass	694.32
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: 10484815

Cas: 160072-38-8

Zinc: ZINC000049823249

Nmrshiftdb2: 60045916

Chembl: CHEMBL445234

No compound-protein relationship available.

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

Level: 4

Mol. Weight: 694.75 g/mol

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

Level: 1

Mol. Weight: 694.75 g/mol

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

Level: 1

Mol. Weight: 694.75 g/mol

SMILES: O=C1CCCN1

Level: 0

Mol. Weight: 694.75 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 694.75 g/mol

Binding assays against the following receptors

Human b2 bradykinin and neuropeptide gamma receptors

Somatostatin

Absorption

Caco-2 (logPapp): -6.53
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.58
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 126.74

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.59
Plasma Protein Binding: 57.28
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: 2.85
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.91
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.43
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.62
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: -224490.03
Rat (Acute): 2.67
Rat (Chronic Oral): 1.34
Fathead Minnow: 294.68
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: 15301.89
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.55
Log(P): -1.66
Log S: -1.53
Log(Vapor Pressure): -579.92
Melting Point: 232.2
pKa Acid: 4.5
pKa Basic: 11.2

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.9398
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.9398
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8770
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8770
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8650
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8650
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8512
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8512
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8463
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8463
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8463
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8463
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8434
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8434
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8045
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8045
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7920
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7920
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7854
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7854
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7804
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7804
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7768
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7768
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7596
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7596
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7534
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7534
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7511
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7511
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7462
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7462
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7427
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7427
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
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7399
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7399
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7378
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7378
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7358
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7358
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7355
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7355
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
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7318
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7318
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
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7289
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7289
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7286
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7286
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7285
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7285
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7270
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	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
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7257
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7257
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7242
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7242
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7217
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7217
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7216
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7216
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7214
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7214
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7212
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7212
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
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7206
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7206
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7198
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7198
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7185
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7185
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7175
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7175
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
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7160
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7160
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7155
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7155
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7129
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7129
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7117
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7117
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7099
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7099
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7094
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7094
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7091
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7091
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7090
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7090
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7089
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7089
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7077
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7077
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7067
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7067
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7064
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7064
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7061
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7061
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7059
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7059
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7057
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7057
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7052
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7052
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7046
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7046
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7045
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7045
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7040
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7040
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7032
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7032
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7019
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7019
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7017
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7017
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
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
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7002
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7002

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