Structure Database (LMSD)

Common Name
Phenylalanocholic Acid
Systematic Name
N-(3α,7α,12α-trihydroxy-5β-cholan-24-oyl)-L-phenylalanine
Synonyms
LM ID
LMST05050056
Formula
C33H49NO6
Exact Mass
Calculate m/z
555.355989
Sum Composition
ST 24:1:O4;Phe
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Bile acids and derivatives [ST04]
C24 bile acids, alcohols, and derivatives [ST0401]
Steroid conjugates [ST05]
Amino acid conjugates [ST0506]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Global chemical effects of the microbiome include new bile-acid conjugations.,
Nature, 2020
Pubmed ID: 32103176

String Representations

InChiKey (Click to copy)
IQKZHEVJCMKOED-RYHSAYMFSA-N
InChi (Click to copy)
InChI=1S/C33H49NO6/c1-19(9-12-29(38)34-26(31(39)40)15-20-7-5-4-6-8-20)23-10-11-24-30-25(18-28(37)33(23,24)3)32(2)14-13-22(35)16-21(32)17-27(30)36/h4-8,19,21-28,30,35-37H,9-18H2,1-3H3,(H,34,38)(H,39,40)/t19-,21+,22-,23-,24+,25+,26+,27-,28+,30+,32+,33-/m1/s1
SMILES (Click to copy)
[C@]12([C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@H](O)[C@]1(C)[C@@]([H])([C@@](C)([H])CCC(N[C@@H](CC3=CC=CC=C3)C(O)=O)=O)CC[C@@]21[H])[H]

Other Databases

PubChem CID
487462

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 5
Aromatic Rings 1
Rotatable Bonds 8
Van der Waals Molecular Volume 557.30
Topological Polar Surface Area 127.09
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 7
logP 5.32
Molar Refractivity 154.16

Admin

Created at
13th Jul 2021
Updated at
19th Feb 2024