SCS-C004969

penicilindole C

Pathway: Alkaloids | Terpenoids Superclass: Tryptophan alkaloids Class: Indole-Diterpenoid alkaloids (Penitrems)

Chemical Structure

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Download: SDF SMILES

Source Information

Eupenicillium sp. (Eupenicillium)

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

South China Sea

DOI: 10.1021/acs.jnatprod.7b00673 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

421.6 Da

Threshold ≤ 500

ALogP

6.42

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C28H39NO2

Molecular Weight:

421.6250 Da

SMILES:

CC(C)=C[C@@H]1C[C@@]23[C@H](CC[C@@H](C)[C@]2(C)CC[C@@](C)(O)[C@H]3Cc2c[nH]c3ccccc23)O1

InChIKey:

                        XHGDWOIUBXSXIP-JTACFZARSA-N
                        
                    

InChI:

InChI=1S/C28H39NO2/c1-18(2)14-21-16-28-24(15-20-17-29-23-9-7-6-8-22(20)23)27(5,30)13-12-26(28,4)19(3)10-11-25(28)31-21/h6-9,14,17,19,21,24-25,29-30H,10-13,15-16H2,1-5H3/t19-,21-,24-,25+,26+,27-,28-/m1/s1

Calculated Properties

ALogP:

6.418 lipophilicity

TPSA:

45.25 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.6429 fraction sp³ carbon

Database Information

Compound ID:

SCS-C004969

NPClassifier Pathway:

Alkaloids Terpenoids

NPClassifier Superclass:

Tryptophan alkaloids

NPClassifier Class:

Indole-Diterpenoid alkaloids (Penitrems)

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD30897

Biological Activity Data

No bioactivity data available for this compound.

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