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
Formula
C20H36O7P2
Exact Mass
Calculate m/z
450.193631
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

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

References

Taxonomy Information

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

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

Other Databases

CHEBI ID
50388
PubChem CID
24883451
SwissLipids ID
SLM:000390227
PDB ID
9AX

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

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Updated at
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