SCS-C005367

methyl (10R,12S,13S,15R,18R,19R,20S,21S)-12-hydroxy-2,7,7,13,18,21-hexamethyl-5,17-dioxo-6,11,14,16-tetraoxahexacyclo[16.3.1.03,8.010,21.012,20.015,19]docosa-1,3(8)-diene-20-carboxylate

Pathway: Terpenoids Superclass: Meroterpenoids Class: Tetraketide meroterpenoids Glycoside

Chemical Structure

Structure of methyl (10R,12S,13S,15R,18R,19R,20S,21S)-12-hydroxy-2,7,7,13,18,21-hexamethyl-5,17-dioxo-6,11,14,16-tetraoxahexacyclo[16.3.1.03,8.010,21.012,20.015,19]docosa-1,3(8)-diene-20-carboxylate

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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

Zhanjiang

DOI: 10.1016/j.fitote.2014.06.011 · Fitoterapia

Talaromyces purpureogenus SCSIO 41517 (NA)

Original source name: Talaromyces purpureogenus SCSIO 41517 | Talaromyces purpureogenus

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Trichocomaceae Genus Talaromyces Species Talaromyces purpureogenus

South China Sea

DOI: 10.1021/acs.jnatprod.1c00681 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

488.5 Da

Threshold ≤ 500

ALogP

2.31

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H32O9

Molecular Weight:

488.5300 Da

SMILES:

COC(=O)[C@]12[C@@H]3[C@H]4OC(=O)[C@]3(C)CC3=C(C)C5=C(C[C@@H](O[C@]1(O)[C@H](C)O4)[C@@]32C)C(C)(C)OC(=O)C5

InChIKey:

                        VKBVOVVIAJLSTD-DUOPOEFESA-N
                        
                    

InChI:

InChI=1S/C26H32O9/c1-11-13-8-17(27)35-22(3,4)14(13)9-16-24(6)15(11)10-23(5)18-19(33-20(23)28)32-12(2)26(30,34-16)25(18,24)21(29)31-7/h12,16,18-19,30H,8-10H2,1-7H3/t12-,16+,18+,19+,23+,24+,25-,26+/m0/s1

Calculated Properties

ALogP:

2.310 lipophilicity

TPSA:

117.59 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (0 aromatic)

Chiral Centers:

Fsp³:

0.7308 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005367

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Meroterpenoids

NPClassifier Class:

Tetraketide meroterpenoids

Glycoside:

Yes

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD24914

Biological Activity Data

No bioactivity data available for this compound.

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