SCS-C007484

(+)-12-hydroxyhomoaerothionin

Pathway: Alkaloids

Chemical Structure

Structure of (+)-12-hydroxyhomoaerothionin

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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

Himerometra magnipinna (NA)

Kingdom Metazoa Phylum Echinodermata Class Crinoidea Order Comatulida Family Himerometridae Genus Himerometra Species Himerometra magnipinna

South China Sea · 8 m

DOI: 10.1021/np060601p · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

848.1 Da

Threshold ≤ 500

ALogP

2.20

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C25H28Br4N4O9

Molecular Weight:

848.1340 Da

SMILES:

COC1=C(Br)[C@H](O)[C@@]2(C=C1Br)CC(C(=O)NCCC(O)CCNC(=O)C1=NO[C@]3(C=C(Br)C(OC)=C(Br)[C@@H]3O)C1)=NO2

InChIKey:

                        QFEIAPMHJHHUFB-KXTAGPOFSA-N
                        
                    

InChI:

InChI=1S/C25H28Br4N4O9/c1-39-18-12(26)7-24(20(35)16(18)28)9-14(32-41-24)22(37)30-5-3-11(34)4-6-31-23(38)15-10-25(42-33-15)8-13(27)19(40-2)17(29)21(25)36/h7-8,11,20-21,34-36H,3-6,9-10H2,1-2H3,(H,30,37)(H,31,38)/t20-,21-,24+,25+/m0/s1

Calculated Properties

ALogP:

2.203 lipophilicity

TPSA:

180.53 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.5200 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007484

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

N/A

NPClassifier Class:

N/A

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
Antibacterial	inhibition zone	Streptomyces 85E HFI assay	11.0 mm	10.1021/np060601p Journal of Natural Products

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