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  3. (3R,11aR)-7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-3,6,11,11a-tetrahydro-2H-pyrazino[1,2-b]isoquinoline-1,4-dione

SCS-C006591

(3R,11aR)-7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-3,6,11,11a-tetrahydro-2H-pyrazino[1,2-b]isoquinoline-1,4-dione

Pathway: Amino acids and Peptides Superclass: Small peptides Class: Dipeptides
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Chemical Structure

Structure of (3R,11aR)-7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-3,6,11,11a-tetrahydro-2H-pyrazino[1,2-b]isoquinoline-1,4-dione
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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

Aspergillus austwickii SCSIO 41227 (NA)
Original source name: Aspergillus austwickii SCSIO41227 | Aspergillus austwickii
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus austwickii
South China Sea
DOI: 10.3390/md21110567  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
407.4 Da
Threshold ≤ 500
ALogP
1.58
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C22H21N3O5
Molecular Weight:
407.4260 Da
SMILES:
COc1c(O)cc2c(c1O)CN1C(=O)[C@@H](Cc3c[nH]c4ccccc34)NC(=O)[C@H]1C2
InChIKey:
FBGQHXBBNVDHIX-IAGOWNOFSA-N
InChI:
InChI=1S/C22H21N3O5/c1-30-20-18(26)8-11-7-17-21(28)24-16(22(29)25(17)10-14(11)19(20)27)6-12-9-23-15-5-3-2-4-13(12)15/h2-5,8-9,16-17,23,26-27H,6-7,10H2,1H3,(H,24,28)/t16-,17-/m1/s1
Calculated Properties
ALogP:
1.582 lipophilicity
TPSA:
114.89 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
5
Rotatable Bonds:
3
Ring Count:
5 (3 aromatic)
Chiral Centers:
2
Fsp³:
0.2727 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006591
NPClassifier Pathway:
Amino acids and Peptides
NPClassifier Superclass:
Small peptides
NPClassifier Class:
Dipeptides
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged