SCS-C000688

Spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2-(3H),2'-[2H]indole]-3',5,10(1'H)-trione

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids Class: Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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Chemical Structure

Structure of Spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2-(3H),2'-[2H]indole]-3',5,10(1'H)-trione

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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

Download: SDF SMILES

Source Information

Talaromyces helicus (NA)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Trichocomaceae Genus Talaromyces Species Talaromyces helicus

South China Sea · -1138

DOI: 10.1007/s13205-022-03237-9 · 3 Biotech

Drug-likeness (Lipinski Ro5)

Molecular Weight

427.5 Da

Threshold ≤ 500

ALogP

0.27

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H25N3O6

Molecular Weight:

427.4570 Da

SMILES:

COc1ccc2c(c1)N[C@@]1(C2=O)[C@H](C=C(C)C)N2C(=O)[C@@H]3CCCN3C(=O)[C@]2(O)[C@H]1O

InChIKey:

                        XPLQKNTVQRYSHU-CTSLQZMRSA-N
                        
                    

InChI:

InChI=1S/C22H25N3O6/c1-11(2)9-16-21(17(26)13-7-6-12(31-3)10-14(13)23-21)19(28)22(30)20(29)24-8-4-5-15(24)18(27)25(16)22/h6-7,9-10,15-16,19,23,28,30H,4-5,8H2,1-3H3/t15-,16-,19-,21+,22+/m0/s1

Calculated Properties

ALogP:

0.273 lipophilicity

TPSA:

119.41 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.5000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000688

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

Indole diketopiperazine alkaloids (L-Trp, L-Pro)

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

Biological Activity Data

No bioactivity data available for this compound.

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