2-(3-{3-Benzyl-12-sec-butyl-9-[2-(4-hydroxy-phenyl)-ethyl]-6,7-dimethyl-2,5,8,11,14-pentaoxo-1,4,7,10,13pentaaza-cyclononadec-15-yl}-ureido)-5-guanidino-pentanoic acid

ID: ALA175436

PubChem CID: 44387258

Max Phase: Preclinical

Molecular Formula: C42H62N10O9

Molecular Weight: 851.02

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Synonyms: Anabaenopeptin F | anabaenopeptin F|Aeruginosin DA850|Anabaenopeptin DA850|CHEMBL175436|CHEBI:204805|BDBM50089687|(2S)-2-[[(3S,6S,9S,12S,15R)-3-benzyl-12-[(2S)-butan-2-yl]-9-[2-(4-hydroxyphenyl)ethyl]-6,7-dimethyl-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentazacyclononadec-15-yl]carbamoylamino]-5-(diaminomethylideneamino)pentanoic acid

Canonical SMILES: CC[C@H](C)[C@@H]1NC(=O)[C@H](NC(=O)N[C@@H](CCCNC(=N)N)C(=O)O)CCCCNC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](C)N(C)C(=O)[C@H](CCc2ccc(O)cc2)NC1=O

Standard InChI: InChI=1S/C42H62N10O9/c1-5-25(2)34-38(57)47-31(21-18-27-16-19-29(53)20-17-27)39(58)52(4)26(3)35(54)48-33(24-28-12-7-6-8-13-28)36(55)45-22-10-9-14-30(37(56)51-34)49-42(61)50-32(40(59)60)15-11-23-46-41(43)44/h6-8,12-13,16-17,19-20,25-26,30-34,53H,5,9-11,14-15,18,21-24H2,1-4H3,(H,45,55)(H,47,57)(H,48,54)(H,51,56)(H,59,60)(H4,43,44,46)(H2,49,50,61)/t25-,26-,30+,31-,32-,33-,34-/m0/s1

Standard InChI Key: RAUPUVQHUFXDQT-IYLLGVDMSA-N

Molfile:

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M  END

Associated Targets(Human)

CPA1 Tchem Carboxypeptidase A1 (146 Activities)

Discover Target: CPA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DUSP3 Tchem Dual specificity protein phosphatase 3 (1161 Activities)

Discover Target: DUSP3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CDC25B Tchem Dual specificity phosphatase Cdc25B (1099 Activities)

Discover Target: CDC25B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F2 Tclin Thrombin (11687 Activities)

Discover Target: F2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRSS1 Tclin Trypsin (2137 Activities)

Discover Target: PRSS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F11 Tchem Coagulation factor XI (1733 Activities)

Discover Target: F11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F7 Tchem Coagulation factor VII (948 Activities)

Discover Target: F7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F10 Tclin Coagulation factor X (9693 Activities)

Discover Target: F10

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CPN1 Tchem Carboxypeptidase N, catalytic subunit (37 Activities)

Discover Target: CPN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CPB2 Tchem Carboxypeptidase B2 isoform A (351 Activities)

Discover Target: CPB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Natural Product: Yes	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Small molecule	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 851.02	Molecular Weight (Monoisotopic): 850.4701	AlogP: 0.60	#Rotatable Bonds: 14
Polar Surface Area: 297.27	Molecular Species: ZWITTERION	HBA: 9	HBD: 11
#RO5 Violations: 2	HBA (Lipinski): 19	HBD (Lipinski): 12	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 3.89	CX Basic pKa: 11.74	CX LogP: -0.61	CX LogD: -0.61
Aromatic Rings: 2	Heavy Atoms: 61	QED Weighted: 0.07	Np Likeness Score: 0.74

References

1. Itou Y, Suzuki S, Ishida K, Murakami M.. (1999) Anabaenopeptins G and H, potent carboxypeptidase A inhibitors from the cyanobacterium Oscillatoria agardhii (NIES-595)., 9 (9): [PMID:10340607] [10.1016/s0960-894x(99)00191-2]
2. Murakami M, Suzuki S, Itou Y, Kodani S, Ishida K.. (2000) New anabaenopeptins, potent carboxypeptidase-A inhibitors from the cyanobacterium Aphanizomenon flos-aquae., 63 (9): [PMID:11000037] [10.1021/np000120k]
3. Sano T, Usui T, Ueda K, Osada H, Kaya K.. (2001) Isolation of new protein phosphatase inhibitors from two cyanobacteria species, Planktothrix spp., 64 (8): [PMID:11520225] [10.1021/np0005356]
4. Adiv S, Carmeli S.. (2013) Protease inhibitors from Microcystis aeruginosa bloom material collected from the Dalton Reservoir, Israel., 76 (12): [PMID:24261937] [10.1021/np4006844]
5. Halland N, Brönstrup M, Czech J, Czechtizky W, Evers A, Follmann M, Kohlmann M, Schiell M, Kurz M, Schreuder HA, Kallus C.. (2015) Novel Small Molecule Inhibitors of Activated Thrombin Activatable Fibrinolysis Inhibitor (TAFIa) from Natural Product Anabaenopeptin., 58 (11): [PMID:25990761] [10.1021/jm501840b]
6. Harms H,Kurita KL,Pan L,Wahome PG,He H,Kinghorn AD,Carter GT,Linington RG. (2016) Discovery of anabaenopeptin 679 from freshwater algal bloom material: Insights into the structure-activity relationship of anabaenopeptin protease inhibitors., 26 (20.0): [PMID:27641470] [10.1016/j.bmcl.2016.09.008]

2-(3-{3-Benzyl-12-sec-butyl-9-[2-(4-hydroxy-phenyl)-ethyl]-6,7-dimethyl-2,5,8,11,14-pentaoxo-1,4,7,10,13pentaaza-cyclononadec-15-yl}-ureido)-5-guanidino-pentanoic acid

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source