SCS-C006419

asperindole A

Pathway: Alkaloids | Terpenoids Superclass: Tryptophan alkaloids Class: Indole-Diterpenoid alkaloids (Penitrems)

Chemical Structure

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Source Information

Aspergillus candidus (Aspergillus)

Original source name: Aspergillus candidus | A. candidus

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus candidus

South China Sea

DOI: 10.3390/md19050281 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

526.0 Da

Threshold ≤ 500

ALogP

4.52

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C29H32ClNO6

Molecular Weight:

526.0290 Da

SMILES:

CC(=O)O[C@@]1(C)CO[C@@]23CC[C@@]4(C)[C@@](O)(CC[C@H]5Cc6c([nH]c7cc(Cl)ccc67)[C@@]54C)C2=CC(=O)[C@@H]1O3

InChIKey:

                        TXNJCXRRMWHWPI-VZTTULSBSA-N
                        
                    

InChI:

InChI=1S/C29H32ClNO6/c1-15(32)36-25(2)14-35-29-10-9-26(3)27(4)16(7-8-28(26,34)22(29)13-21(33)24(25)37-29)11-19-18-6-5-17(30)12-20(18)31-23(19)27/h5-6,12-13,16,24,31,34H,7-11,14H2,1-4H3/t16-,24-,25-,26+,27+,28+,29+/m0/s1

Calculated Properties

ALogP:

4.519 lipophilicity

TPSA:

97.85 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (2 aromatic)

Chiral Centers:

Fsp³:

0.5862 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006419

NPClassifier Pathway:

Alkaloids Terpenoids

NPClassifier Superclass:

Tryptophan alkaloids

NPClassifier Class:

Indole-Diterpenoid alkaloids (Penitrems)

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	effect on spontaneous Ca2+ oscillations (SCOs)	primary cultured neocortical neurons	For the cluster of indole-diterpene alkaloids, ring cleavage on the ether bridge of ring G seems critical for the activity since all those compounds that have ring G are not active	10.3390/md19050281 Marine Drugs

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