Structure Database (LMSD)

Common Name
tuberculosinyl diphosphate
Systematic Name
(2E)-3-methyl-5-[(1R,2S,8aS)-1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]pent-2-en-1-yl trihydrogen diphosphate
Synonyms
  • halima-5(6),13-dien-15-ol
  • tuberculosinol diphosphate
LM ID
LMPR0104030006
Status
Active
Exact Mass
Calculate m/z
450.193631
Formula
C20H36O7P2
Show lipids differing only in stereochemistry/bond geometry
Download as...
MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C20 isoprenoids (diterpenes) [PR0104]
Labdane and halimane diterpenoids [PR010403]

String Representations

InChiKey (Click to copy)
BPSHPRCHMGHBGC-AHKHSGQUSA-N
InChi (Click to copy)
InChI=1S/C20H36O7P2/c1-15(11-14-26-29(24,25)27-28(21,22)23)10-13-20(5)16(2)8-9-17-18(20)7-6-12-19(17,3)4/h9,11,16,18H,6-8,10,12-14H2,1-5H3,(H,24,25)(H2,21,22,23)/b15-11+/t16-,18+,20+/m0/s1
SMILES (Click to copy)
C1[C@]2([H])C(=CC[C@H](C)[C@]2(CC/C(/C)=C/COP(O)(=O)OP(O)(O)=O)C)C(C)(C)CC1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mycobacterium tuberculosis H37Rv (#83332)
Actinomycetia (#1760)
Mycobacterium tuberculosis H37Rv3377c encodes the diterpene cyclase for producing the halimane skeleton.,
Chem Commun (Camb), 2005
Pubmed ID: 15719101

Other Databases

CHEBI ID
50388
PubChem CID
24883451
SwissLipids ID
SLM:000390227

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 2
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 425.75
Topological Polar Surface Area 113.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 6.53
Molar Refractivity 113.07

Admin

Created at
-
Updated at
-