SCS-C003246

spirobrocazine A

Pathway: Amino acids and Peptides Superclass: Peptide alkaloids Class: Thiodiketopiperazine alkaloids

Chemical Structure

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Source Information

Penicillium brocae (NA)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species Penicillium brocae

Hainan Island

DOI: 10.1021/acs.orglett.6b02620 · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

370.4 Da

Threshold ≤ 500

ALogP

0.96

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C19H18N2O4S

Molecular Weight:

370.4300 Da

SMILES:

CS[C@@]12CC3=CC=C[C@H](O)[C@H]3N1C(=O)[C@@]1(Cc3ccccc3O1)NC2=O

InChIKey:

                        QFWGYIKIPBTLBM-KNEBKQPDSA-N
                        
                    

InChI:

InChI=1S/C19H18N2O4S/c1-26-19-10-12-6-4-7-13(22)15(12)21(19)17(24)18(20-16(19)23)9-11-5-2-3-8-14(11)25-18/h2-8,13,15,22H,9-10H2,1H3,(H,20,23)/t13-,15-,18-,19+/m0/s1

Calculated Properties

ALogP:

0.965 lipophilicity

TPSA:

78.87 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.3684 fraction sp³ carbon

Database Information

Compound ID:

SCS-C003246

NPClassifier Pathway:

Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

Thiodiketopiperazine alkaloids

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD27683

Biological Activity Data

No bioactivity data available for this compound.

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