SCS-C001826

Amantamide A

Pathway: Amino acids and Peptides Superclass: Oligopeptides Class: Depsipeptides | Linear peptides

Chemical Structure

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Download: SDF SMILES

Source Information

Oscillatoria sp. (NA)

Kingdom Bacillati Phylum Cyanobacteriota Class Cyanophyceae Order Oscillatoriales Family Oscillatoriaceae Genus Oscillatoria Species NA

Xisha Islands · -10-15 m · 16°51'05.52"N, 112°20'56.13"E

DOI: 10.1021/acs.jnatprod.1c00983 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

1080.4 Da

Threshold ≤ 500

ALogP

3.69

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C57H93N9O11

Molecular Weight:

1080.4000 Da

SMILES:

CCCC(=O)N[C@H](C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N(C)[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N(C)[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OC)[C@@H](C)CC)C(C)C)C(C)C

InChIKey:

                        ZPZNPEATKLIUKY-SFHKMCQHSA-N
                        
                    

InChI:

InChI=1S/C57H93N9O11/c1-16-23-45(67)60-47(36(7)8)56(75)63(13)43(31-35(5)6)50(69)59-40(30-34(3)4)53(72)65-28-21-26-41(65)54(73)64(14)49(37(9)10)52(71)61-48(38(11)17-2)51(70)58-33-46(68)62(12)44(32-39-24-19-18-20-25-39)55(74)66-29-22-27-42(66)57(76)77-15/h18-20,24-25,34-38,40-44,47-49H,16-17,21-23,26-33H2,1-15H3,(H,58,70)(H,59,69)(H,60,67)(H,61,71)/t38-,40-,41-,42-,43-,44+,47-,48-,49+/m0/s1

Calculated Properties

ALogP:

3.686 lipophilicity

TPSA:

244.25 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.7193 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001826

NPClassifier Pathway:

Amino acids and Peptides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

Depsipeptides Linear peptides

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.

Activity	Assay	Target / model	Result	Reference
Antitumor	—	U937	8.3 ± 1.6 μM	10.1021/acs.jnatprod.1c00983 Journal of Natural Products

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