Structure Database (LMSD)

Common Name
PIM5(17:0/16:2(9Z,12Z))
Systematic Name
2'-O-(α-D-Manp)-6'-O-(α-D-Manp-1->6-α-D-Manp-1->6-α-D-Manp-1->6-α-D-Manp)-(1-heptadecanoyl-2-(9Z,12Z-hexadecadienoyl)-sn-glycero-3-phospho-1'-myo-inositol)
Synonyms
  • PIM5(33:2)
  • PIM5(16:2_17:0)
LM ID
LMGP15010203
Formula
C72H127O38P
Exact Mass
Calculate m/z
1630.774308
Sum Composition
PIM5 33:2
Abbrev Chains
PIM5 16:2_17:0
Status
Active (generated by computational methods)
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Glycerophosphoinositolglycans [GP15]
Diacylglycerophosphoinositolglycans [GP1501]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mycobacterium tuberculosis (#1773)
Actinomycetes (#1760)
Lipidomic analyses of Mycobacterium tuberculosis based on accurate mass measurements and the novel "Mtb LipidDB".,
J Lipid Res, 2011
Pubmed ID: 21285232

String Representations

InChiKey (Click to copy)
LWCFODJANIVJMR-HPBHWHQMSA-N
InChi (Click to copy)
InChI=1S/C72H127O38P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-45(75)97-34-39(102-46(76)31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)35-101-111(95,96)110-67-65(108-71-63(93)53(83)48(78)41(33-74)104-71)58(88)57(87)59(89)66(67)109-72-64(94)56(86)51(81)44(107-72)38-100-70-62(92)55(85)50(80)43(106-70)37-99-69-61(91)54(84)49(79)42(105-69)36-98-68-60(90)52(82)47(77)40(32-73)103-68/h8,10,14,16,39-44,47-74,77-94H,3-7,9,11-13,15,17-38H2,1-2H3,(H,95,96)/b10-8-,16-14-/t39-,40-,41-,42-,43-,44-,47-,48-,49-,50-,51-,52+,53+,54+,55+,56+,57-,58-,59+,60+,61+,62+,63+,64+,65+,66+,67-,68+,69+,70+,71-,72-/m1/s1
SMILES (Click to copy)
[C@](COP(O[C@H]1[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]3[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]4[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]5[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O5)O4)O3)O2)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)(=O)O)([H])(OC(CCCCCCC/C=C\C/C=C\CCC)=O)COC(CCCCCCCCCCCCCCCC)=O

Other Databases

PubChem CID
126457571

Calculated Physicochemical Properties

Heavy Atoms 111
Rings 6
Aromatic Rings 0
Rotatable Bonds 52
Van der Waals Molecular Volume 1523.29
Topological Polar Surface Area 615.61
Hydrogen Bond Donors 21
Hydrogen Bond Acceptors 38
logP 8.12
Molar Refractivity 399.42

Admin

Created at
-
Updated at
25th Apr 2022
LIPID MAPS® abbreviations for glycerophospholipids (GP)

The LIPID MAPS® glycerophospholipid abbreviations (PC, PE, etc.) are used here to refer to species with one or two radyl side-chains where the structures of the side chains are indicated within parentheses in the 'Headgroup(sn1/sn2)' format (e.g. PC(16:0/18:1(9Z)). By default, R stereochemistry at the C-2 carbon of glycerol and attachment of the headgroup at the sn3 position is assumed. Also, acyl chains are assumed by default. The 'O-' prefix is used to indicate the presence of an alkyl ether substituent e.g. PC(O-16:0/18:1(9Z)), whereas the 'P-' prefix is used for the 1Z-alkenyl ether (Plasmalogen) substituent e.g. PC(P-16:0/18:1(9Z)).

For molecules with opposite (S) stereochemistry at C2 of the glycerol group and attachment of the headgroup at the sn1 position, the stereochemistry specification of [S] is appended to the abbreviation. The 'Headgroup(sn3/sn2)' abbreviation format is used.

For molecules with unknown stereochemistry at the C-2 carbon of the glycerol group, the stereochemistry specification of [U] is appended to the abbreviation and the structure is drawn with C-2 stereochemistry unspecified.