1.0
2011-09-21 00:30:24 UTC
2017-03-11 23:00:23 UTC
FDB023471
Trihexosylceramide (d18:1/9Z-18:1)
Trihexosylceramide is a glycosphingolipid which contains a trisaccharide (galactose-galactose-glucose) moiety bound in glycosidic linkage to the hydroxyl group of ceramide as the polar head group. It accumulates in tissue due to a defect in ceramide trihexosidase and is the cause of angiokeratoma corporis diffusum (Fabry disease).
Although normal human colonic epithelial cells lack the glycosphingolipid globotriaosylceramide (Gb(3)), this molecule is highly expressed in metastatic colon cancer (PubMed ID 16365318 ) [HMDB]
C54H99NO18
1050.3598
1049.686215369
(9E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]octadec-9-enamide
(9E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]octadec-9-enamide
71965-57-6
CCCCCCCCCCCCC\C=C\C(O)C(COC1OC(CO)C(OC2OC(CO)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C1O)NC(=O)CCCCCCC\C=C\CCCCCCCC
InChI=1S/C54H99NO18/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-42(60)55-37(38(59)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)36-68-52-48(66)45(63)50(40(34-57)70-52)73-54-49(67)46(64)51(41(35-58)71-54)72-53-47(65)44(62)43(61)39(33-56)69-53/h17-18,29,31,37-41,43-54,56-59,61-67H,3-16,19-28,30,32-36H2,1-2H3,(H,55,60)/b18-17+,31-29+
XRPQSEBNLXORQZ-LSUSWXEESA-N
Solid
logp
4.93
logs
-4.73
solubility
1.94e-02 g/l
logp
6.08
pka_strongest_acidic
11.76
pka_strongest_basic
-3.6
iupac
(9E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]octadec-9-enamide
average_mass
1050.3598
mono_mass
1049.686215369
smiles
CCCCCCCCCCCCC\C=C\C(O)C(COC1OC(CO)C(OC2OC(CO)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C1O)NC(=O)CCCCCCC\C=C\CCCCCCCC
formula
C54H99NO18
inchi
InChI=1S/C54H99NO18/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-42(60)55-37(38(59)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)36-68-52-48(66)45(63)50(40(34-57)70-52)73-54-49(67)46(64)51(41(35-58)71-54)72-53-47(65)44(62)43(61)39(33-56)69-53/h17-18,29,31,37-41,43-54,56-59,61-67H,3-16,19-28,30,32-36H2,1-2H3,(H,55,60)/b18-17+,31-29+
inchikey
XRPQSEBNLXORQZ-LSUSWXEESA-N
polar_surface_area
307.01
refractivity
273.33
polarizability
122.21
rotatable_bond_count
40
acceptor_count
18
donor_count
12
physiological_charge
0
formal_charge
0
Specdb::MsMs
3036503
Specdb::MsMs
3036504
Specdb::MsMs
3036505
Specdb::MsMs
3104336
Specdb::MsMs
3104337
Specdb::MsMs
3104338
HMDB04878
#<Reference:0x000055567497ddb0>
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#<Reference:0x000055567497d810>
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#<Reference:0x000055567497d248>
#<Reference:0x000055567497d068>
#<Reference:0x000055567497ce60>
#<Reference:0x000055567497cca8>
#<Reference:0x000055567497cac8>
#<Reference:0x000055567497c8c0>
#<Reference:0x000055567497c5f0>
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Anatidae
Type 1
specific
Anatidae
8830
Beefalo
Type 1
specific
Bos taurus X Bison bison
297284
Bison
Type 1
specific
Bison bison
9901
Buffalo
Type 1
specific
Bubalus bubalis
89462
Cattle (Beef, Veal)
Type 1
specific
Bos taurus
9913
Chicken
Type 1
specific
Gallus gallus
9031
Columbidae (Dove, Pigeon)
Type 1
specific
Columbidae
8930
Deer
Type 1
specific
Cervidae
9850
Domestic goat
Type 1
specific
Capra aegagrus hircus
9925
Domestic pig
Type 1
specific
Sus scrofa domestica
9825
Elk
Type 1
specific
Cervus canadensis
1574408
Emu
Type 1
specific
Dromaius novaehollandiae
8790
European rabbit
Type 1
specific
Oryctolagus
9984
Greylag goose
Type 1
specific
Anser anser
8843
Guinea hen
Type 1
specific
Numida meleagris
8996
Horse
Type 1
specific
Equus caballus
9796
Mallard duck
Type 1
specific
Anas platyrhynchos
8839
Mountain hare
Type 1
specific
Lepus timidus
62621
Mule deer
Type 1
specific
Odocoileus
9871
Ostrich
Type 1
specific
Struthio camelus
8801
Pheasant
Type 1
specific
Phasianus colchicus
9054
Quail
Type 1
specific
Phasianidae
9005
Rabbit
Type 1
specific
Leporidae
9979
Rock ptarmigan
Type 1
specific
Lagopus muta
64668
Sheep (Mutton, Lamb)
Type 1
specific
Ovis aries
9940
Squab
Type 1
specific
Columba
8931
Turkey
Type 1
specific
Meleagris gallopavo
9103
Velvet duck
Type 1
specific
Melanitta fusca
371864
Wild boar
Type 1
specific
Sus scrofa
9823
Acid ceramidase
Q13510
ASAH1
Alkaline ceramidase 1
Q8TDN7
ACER1
Alkaline ceramidase 2
Q5QJU3
ACER2
Alpha-galactosidase A
P06280
GLA
Antigen-presenting glycoprotein CD1d
P15813
CD1D
Beta-1,3-galactosyltransferase 5
Q9Y2C3
B3GALT5
Beta-hexosaminidase subunit alpha
P06865
HEXA
Beta-hexosaminidase subunit beta
P07686
HEXB
Ceramide glucosyltransferase
Q16739
UGCG
Ceramide synthase 1
P27544
CERS1
Collagen type IV alpha-3-binding protein
Q9Y5P4
COL4A3BP
Epididymal secretory protein E1
P61916
NPC2
Galactocerebrosidase
P54803
GALC
Ganglioside GM2 activator
P17900
GM2A
Glucosylceramidase
P04062
GBA
GPI ethanolamine phosphate transferase 1
O95427
PIGN
GPI ethanolamine phosphate transferase 2
Q5H8A4
PIGG
GPI ethanolamine phosphate transferase 3
Q8TEQ8
PIGO
GPI mannosyltransferase 1
Q9H3S5
PIGM
GPI mannosyltransferase 2
Q9NUD9
PIGV
GPI mannosyltransferase 3
Q92521
PIGB
GPI mannosyltransferase 4
Q86VD9
PIGZ
GPI transamidase component PIG-S
Q96S52
PIGS
GPI transamidase component PIG-T
Q969N2
PIGT
GPI-anchor transamidase
Q92643
PIGK
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase
Q9BYG0
B3GNT5
Lactosylceramide 4-alpha-galactosyltransferase
Q9NPC4
A4GALT
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase
Q9Y2B2
PIGL
Neutral ceramidase
Q9NR71
ASAH2
Non-lysosomal glucosylceramidase
Q9HCG7
GBA2
Phosphatidylinositol glycan anchor biosynthesis class U protein
Q9H490
PIGU
Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
P37287
PIGA
Phosphatidylinositol N-acetylglucosaminyltransferase subunit C
Q92535
PIGC
Phosphatidylinositol N-acetylglucosaminyltransferase subunit H
Q14442
PIGH
Phosphatidylinositol N-acetylglucosaminyltransferase subunit P
P57054
PIGP
Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
Q9BRB3
PIGQ
Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y
Q3MUY2
PIGY
Phosphatidylinositol-glycan biosynthesis class F protein
Q07326
PIGF
Phosphatidylinositol-glycan biosynthesis class W protein
Q7Z7B1
PIGW
Phosphatidylinositol-glycan biosynthesis class X protein
Q8TBF5
PIGX
Putative neutral ceramidase C
P0C7U2
ASAH2C
Sphingomyelin phosphodiesterase
P17405
SMPD1
T-cell surface glycoprotein CD1e, membrane-associated
P15812
CD1E