SCS-C007391

pyrrospirone Y

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.5c01203 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

515.7 Da

Threshold ≤ 500

ALogP

5.54

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:

C33H41NO4

Molecular Weight:

515.6940 Da

SMILES:

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

InChIKey:

                        JQBLUAYVAZEBCQ-ZQHYBPRPSA-N
                        
                    

InChI:

InChI=1S/C33H41NO4/c1-7-12-32(5)16-19(4)25-24-27(32)28(35)23-22(30(36)34-31(23)37)14-20-8-10-21(11-9-20)38-29(24)26-18(3)13-17(2)15-33(25,26)6/h7-12,16-18,22-27,29H,13-15H2,1-6H3,(H,34,36,37)/b12-7+/t17-,18+,22+,23+,24+,25-,26+,27+,29+,32+,33+/m1/s1

Calculated Properties

ALogP:

5.541 lipophilicity

TPSA:

72.47 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (1 aromatic)

Chiral Centers:

Fsp³:

0.6061 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007391

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
Antitumor	IC50	human cancer cell lines A549 and HCT116	— Structured numeric value is not available in this record; see the primary reference.	10.1021/acs.jnatprod.5c01203 Journal of Natural Products

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