SCS-C008268

FD7177CD6

Pathway: Alkaloids | Amino acids and Peptides Superclass: Tetramate alkaloids Class: Pyrrocidine tetramate alkaloids

Chemical Structure

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Source Information

Penicillium sp. (soft coral-derived fungus)

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

South China Sea

DOI: 10.1021/acs.jnatprod.2c00473 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

503.7 Da

Threshold ≤ 500

ALogP

5.71

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

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

Chemical Properties

Molecular Formula:

C32H41NO4

Molecular Weight:

503.6830 Da

SMILES:

C=C[C@@]1(C)C=C(C)[C@H]2[C@@H]3[C@@H](Oc4ccc(cc4)C[C@@]4(O)C/C(=C(\O)[C@H]31)C(=O)N4)[C@@H]1[C@@H](C)C[C@@H](C)C[C@@]12C

InChIKey:

                        RHWUVEFQIICMCY-QGLHFLNHSA-N
                        
                    

InChI:

InChI=1S/C32H41NO4/c1-7-30(5)14-19(4)24-23-26(30)27(34)22-16-32(36,33-29(22)35)15-20-8-10-21(11-9-20)37-28(23)25-18(3)12-17(2)13-31(24,25)6/h7-11,14,17-18,23-26,28,34,36H,1,12-13,15-16H2,2-6H3,(H,33,35)/b27-22+/t17-,18+,23+,24+,25+,26+,28-,30+,31-,32-/m1/s1

Calculated Properties

ALogP:

5.714 lipophilicity

TPSA:

78.79 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (1 aromatic)

Chiral Centers:

Fsp³:

0.5938 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008268

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Tetramate alkaloids

NPClassifier Class:

Pyrrocidine tetramate alkaloids

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
Other specified activity	IC50	several PTPs	39.4–100.0 μM	10.1021/acs.jnatprod.2c00473 Journal of Natural Products
Antibacterial	IC50	six tested pathogens: Bacillus amyloliquefaciens, B. subtilis, Escherichia coli, Staphylococcus aureus, S. aureus MRSA, Streptococcus agalactiae	5.0–20.0 μg/mL	10.1021/acs.jnatprod.2c00473 Journal of Natural Products

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