SCS-C000236

16β,17α-dihydroxy-deoxydihydroisoaustamide

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 16β,17α-dihydroxy-deoxydihydroisoaustamide

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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 dimorphosporum (NA)

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

South China Sea

DOI: 10.3390/md19010032 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

381.4 Da

Threshold ≤ 500

ALogP

1.01

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C21H23N3O4

Molecular Weight:

381.4320 Da

SMILES:

CC1(C)/C=C\N2C(=O)[C@]3(O)[C@H](O)CCN3C(=O)[C@@H]2Cc2c1[nH]c1ccccc21

InChIKey:

                        UCLDBIJVWLLIRK-AUUSZHTLSA-N
                        
                    

InChI:

InChI=1S/C21H23N3O4/c1-20(2)8-10-23-15(11-13-12-5-3-4-6-14(12)22-17(13)20)18(26)24-9-7-16(25)21(24,28)19(23)27/h3-6,8,10,15-16,22,25,28H,7,9,11H2,1-2H3/b10-8-/t15-,16+,21+/m0/s1

Calculated Properties

ALogP:

1.008 lipophilicity

TPSA:

96.87 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.4286 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000236

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

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
Neuroprotective / Neuromodulatory	inhibition_percent	PQ-treated Neuro-2a cells	36.5 %	10.3390/md19010032 Marine Drugs
Neuroprotective / Neuromodulatory	—	PQ-treated Neuro-2a cells	39.4 %	10.3390/md19010032 Marine Drugs

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