Globo H information

Globo H
Names
	IUPAC name N-((2S,3R,E)-1-(((2R,3R,4R,5S,6R)-5-(((2S,3R,4R,5R,6R)-5-(((2R,3R,4S,5S,6R)-4-(((2S,3R,4R,5R,6R)-3-acetamido-4-(((2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-hydroxyoctadec-4-en-2-yl)palmitamide
	Other names globohexaosylceramide; α-L-Fuc-(1→2)-β-D-Gal-(1→3)-β-D-GalNAc-(1→3)-α-D-Gal-(1→4)-β-D-Gal-(1→4)-α-D-GlcOCeramide;
Identifiers
CAS Number	77538-31-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:62361;
	InChI InChI=1S/C72H130N2O32/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-42(81)41(74-48(82)32-30-28-26-24-22-20-18-16-14-12-10-8-6-2)38-95-68-59(92)56(89)62(46(36-78)100-68)102-70-60(93)57(90)63(47(37-79)101-70)103-71-61(94)65(53(86)45(35-77)98-71)105-67-49(73-40(4)80)64(52(85)44(34-76)97-67)104-72-66(55(88)51(84)43(33-75)99-72)106-69-58(91)54(87)50(83)39(3)96-69/h29,31,39,41-47,49-72,75-79,81,83-94H,5-28,30,32-38H2,1-4H3,(H,73,80)(H,74,82)/b31-29+/t39-,41-,42+,43+,44+,45+,46+,47+,49+,50+,51-,52+,53-,54+,55-,56+,57+,58-,59+,60+,61+,62+,63-,64+,65-,66+,67-,68+,69-,70-,71+,72-/m0/s1 Key: NQUSQNBGWFMOFP-PBNVMRQJSA-N;
	SMILES CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O[C@@H]5O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]5O)[C@H]4NC(C)=O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(CCCCCCCCCCCCCCC)=O;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Globo H (globohexaosylceramide) is a globo-series glycosphingolipid antigen that is present on the outer membrane of some cancer cells.^[1]^[2] Globo H is not expressed in normal tissue cells, but is expressed in a number of types of cancers, including cancers of the breast, prostate, and pancreas.^[1]^[3] Globo H's exclusivity for cancer cells makes it a target of interest for cancer therapies.^[1]^[2]

^ ^a ^b ^c Chuang, Po-Kai; Hsiao, Michael; Hsu, Tsui-Ling; Chang, Chuan-Fa; Wu, Chung-Yi; Chen, Bo-Rui; Huang, Han-Wen; Liao, Kuo-Shiang; Chen, Chen-Chun; Chen, Chi-Long; Yang, Shun-Min (2019-02-26). "Signaling pathway of globo-series glycosphingolipids and β1,3-galactosyltransferase V (β3GalT5) in breast cancer". Proceedings of the National Academy of Sciences. 116 (9): 3518–3523. doi:10.1073/pnas.1816946116. ISSN 0027-8424. PMC 6397564. PMID 30808745.
^ ^a ^b Hung, Jung-Tung; Cheng, Jing-Yan; Wu, Chia-Cheng; Yu, Alice L. (2012-04-15). "Abstract 2529: A monoclonal anti-Globo H antibody, VK9 can mediate CDC/ADCC and inhibit adhesion of Globo H+cancer cells to extracellular matrix". Abstract 2529: A monoclonal anti-Globo H antibody, VK9 can mediate CDC/ADCC and inhibit adhesion of Globo H+ cancer cells to extracellular matrix. Vol. 72. p. 2529. doi:10.1158/1538-7445.AM2012-2529. ISSN 0008-5472. {{cite book}}: |journal= ignored (help)
^ Yang, Ching-Yao; Lin, Mong-Wei; Chang, Yih-Leong; Wu, Chen-Tu (2017-12-12). "Globo H expression is associated with driver mutations and PD-L1 expressions in stage I non-small cell lung cancer". Cancer Biomarkers. 21 (1): 211–220. doi:10.3233/CBM-170660. ISSN 1875-8592. PMID 29036791.

[:0-1] Chuang, Po-Kai; Hsiao, Michael; Hsu, Tsui-Ling; Chang, Chuan-Fa; Wu, Chung-Yi; Chen, Bo-Rui; Huang, Han-Wen; Liao, Kuo-Shiang; Chen, Chen-Chun; Chen, Chi-Long; Yang, Shun-Min (2019-02-26). "Signaling pathway of globo-series glycosphingolipids and β1,3-galactosyltransferase V (β3GalT5) in breast cancer". Proceedings of the National Academy of Sciences. 116 (9): 3518–3523. doi:10.1073/pnas.1816946116. ISSN 0027-8424. PMC 6397564. PMID 30808745.

[:1-2] Hung, Jung-Tung; Cheng, Jing-Yan; Wu, Chia-Cheng; Yu, Alice L. (2012-04-15). "Abstract 2529: A monoclonal anti-Globo H antibody, VK9 can mediate CDC/ADCC and inhibit adhesion of Globo H+cancer cells to extracellular matrix". Abstract 2529: A monoclonal anti-Globo H antibody, VK9 can mediate CDC/ADCC and inhibit adhesion of Globo H+ cancer cells to extracellular matrix. Vol. 72. p. 2529. doi:10.1158/1538-7445.AM2012-2529. ISSN 0008-5472. {{cite book}}: |journal= ignored (help)

[3] Yang, Ching-Yao; Lin, Mong-Wei; Chang, Yih-Leong; Wu, Chen-Tu (2017-12-12). "Globo H expression is associated with driver mutations and PD-L1 expressions in stage I non-small cell lung cancer". Cancer Biomarkers. 21 (1): 211–220. doi:10.3233/CBM-170660. ISSN 1875-8592. PMID 29036791.

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Names

IUPAC name N-((2S,3R,E)-1-(((2R,3R,4R,5S,6R)-5-(((2S,3R,4R,5R,6R)-5-(((2R,3R,4S,5S,6R)-4-(((2S,3R,4R,5R,6R)-3-acetamido-4-(((2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-hydroxyoctadec-4-en-2-yl)palmitamide
Other names globohexaosylceramide α-L-Fuc-(1→2)-β-D-Gal-(1→3)-β-D-GalNAc-(1→3)-α-D-Gal-(1→4)-β-D-Gal-(1→4)-α-D-GlcOCeramide
Identifiers
CAS Number	77538-31-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:62361
InChI InChI=1S/C72H130N2O32/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-42(81)41(74-48(82)32-30-28-26-24-22-20-18-16-14-12-10-8-6-2)38-95-68-59(92)56(89)62(46(36-78)100-68)102-70-60(93)57(90)63(47(37-79)101-70)103-71-61(94)65(53(86)45(35-77)98-71)105-67-49(73-40(4)80)64(52(85)44(34-76)97-67)104-72-66(55(88)51(84)43(33-75)99-72)106-69-58(91)54(87)50(83)39(3)96-69/h29,31,39,41-47,49-72,75-79,81,83-94H,5-28,30,32-38H2,1-4H3,(H,73,80)(H,74,82)/b31-29+/t39-,41-,42+,43+,44+,45+,46+,47+,49+,50+,51-,52+,53-,54+,55-,56+,57+,58-,59+,60+,61+,62+,63-,64+,65-,66+,67-,68+,69-,70-,71+,72-/m0/s1 Key: NQUSQNBGWFMOFP-PBNVMRQJSA-N
SMILES CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O[C@@H]5O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]5O)[C@H]4NC(C)=O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(CCCCCCCCCCCCCCC)=O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references