SCS-C003275

brocazine D

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

Chemical Structure

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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

Penicillium brocae (NA)

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

Hainan Island

DOI: 10.1021/np500382k · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

470.5 Da

Threshold ≤ 500

ALogP

-1.73

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C19H22N2O8S2

Molecular Weight:

470.5250 Da

SMILES:

CO[C@H]1CC(=O)[C@@H]2C[C@@]34SS[C@]5(C[C@H]6C(=O)C[C@H](O)[C@H](O)[C@H]6N5C3=O)C(=O)N4[C@@H]2[C@H]1O

InChIKey:

                        OQBICUASXZODNX-NCRURJJJSA-N
                        
                    

InChI:

InChI=1S/C19H22N2O8S2/c1-29-11-3-9(23)7-5-19-16(27)20-12-6(8(22)2-10(24)14(12)25)4-18(20,30-31-19)17(28)21(19)13(7)15(11)26/h6-7,10-15,24-26H,2-5H2,1H3/t6-,7-,10-,11-,12-,13-,14-,15-,18+,19+/m0/s1

Calculated Properties

ALogP:

-1.735 lipophilicity

TPSA:

144.68 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (0 aromatic)

Chiral Centers:

Fsp³:

0.7895 fraction sp³ carbon

Database Information

Compound ID:

SCS-C003275

NPClassifier Pathway:

Alkaloids 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: CMNPD24904

Biological Activity Data

No bioactivity data available for this compound.

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