SCS-C003209

brocazine C

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

440.5 Da

Threshold ≤ 500

ALogP

-1.79

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C18H20N2O7S2

Molecular Weight:

440.4990 Da

SMILES:

O=C1C[C@H](O)[C@H](O)[C@@H]2[C@H]1C[C@@]13SS[C@]4(C[C@H]5[C@@H]([C@@H](O)C=C[C@@H]5O)N4C1=O)C(=O)N23

InChIKey:

                        LPUHZOUWCQALDK-LENHPZMJSA-N
                        
                    

InChI:

InChI=1S/C18H20N2O7S2/c21-8-1-2-9(22)12-6(8)4-17-16(27)20-13-7(10(23)3-11(24)14(13)25)5-18(20,29-28-17)15(26)19(12)17/h1-2,6-9,11-14,21-22,24-25H,3-5H2/t6-,7+,8+,9+,11+,12+,13+,14+,17-,18-/m1/s1

Calculated Properties

ALogP:

-1.792 lipophilicity

TPSA:

138.61 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (0 aromatic)

Chiral Centers:

Fsp³:

0.7222 fraction sp³ carbon

Database Information

Compound ID:

SCS-C003209

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: CMNPD24903

Biological Activity Data

No bioactivity data available for this compound.

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