SCS-C006774

12,13-dihydroxyfumitremorgin C

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids Class: Indole diketopiperazine alkaloids (L-Trp, L-Pro)

Back to List

Chemical Structure

Structure of 12,13-dihydroxyfumitremorgin C

Loading 3D structure...

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

Aspergillus sydowii (coral-derived fungus)

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

South China Sea

DOI: 10.1177/1934578x1300800313 · Natural Product Communications

Drug-likeness (Lipinski Ro5)

Molecular Weight

381.4 Da

Threshold ≤ 500

ALogP

1.74

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:

CC(C)=C[C@H]1c2[nH]c3ccccc3c2[C@H](O)[C@]2(O)C(=O)N3CCC[C@H]3C(=O)N12

InChIKey:

                        CSRLIYIWILNEDP-YYJDGNJWSA-N
                        
                    

InChI:

InChI=1S/C21H23N3O4/c1-11(2)10-15-17-16(12-6-3-4-7-13(12)22-17)18(25)21(28)20(27)23-9-5-8-14(23)19(26)24(15)21/h3-4,6-7,10,14-15,18,22,25,28H,5,8-9H2,1-2H3/t14-,15-,18-,21-/m0/s1

Calculated Properties

ALogP:

1.744 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-C006774

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
Antifouling	settlement inhibition	Bugula neritina larvae	9–16 were tested only towards B. neritina larvae because of the sample amount limitation... 6, 9, 13, and 16 towards B. neritina larvae	10.1177/1934578x1300800313 Natural Product Communications

Back to Compounds