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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:06 UTC

HMDB ID

HMDB0000849

Secondary Accession Numbers

HMDB00849

Metabolite Identification

Common Name

Rhamnose

Description

Rhamnose (Rham) is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Rhamnose is commonly bound to other sugars in nature. It is a common glycone component of glycosides from many plants. Rhamnose is also a component of the outer cell membrane of certain bacteria. L-rhamnose is metabolized to L-Lactaldehyde, which is a branching point in the metabolic pathway of L-fucose and L-rhamnose utilization. It exists in two anomeric forms, alpha-L-rhamnose and beta-L-rhamnose. Rhamnose has been found in Klebsiella, Pseudomonas (https://link.springer.com/article/10.1007/BF00369505) (https://onlinelibrary.wiley.com/doi/abs/10.1002/ejlt.200300816).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Deoxy-L-mannose	ChEBI
L-(+)-Rhamnose	ChEBI
L-Mannomethylose	ChEBI
L-Rha	ChEBI
L-Rhamnose	ChEBI
L-Rhamnopyranose	Kegg
6-Deoxy-L(+)-mannose	HMDB
6-Deoxy-L-mannopyranose	HMDB
6-Deoxy-mannose	HMDB
6-Deoxyhexopyranose	HMDB
6-Deoxyhexose	HMDB
6-Deoxymannose	HMDB
Isodulcit	HMDB
Isodulcitol	HMDB
L(+)-Rhamnose	HMDB
L(+)-Rhamnose monohydrate	HMDB
L-(+)-Rhamnose 1-hydrate	HMDB
L-(+)-Rhamnose hydrate = 6-deoxy-L-mannose monohydrate	HMDB
L-(+)-Rhamnose monohydrate	HMDB
L-Rhamnose for biochemistry	HMDB
L-Rhamnose monohydrate	HMDB
Locaose	HMDB
mono(6-Deoxy-b-L-mannopyranosyl) ester	HMDB
mono(6-Deoxy-beta-L-mannopyranosyl) ester	HMDB
p-(6-Deoxy-b-L-mannopyranosyl) ester	HMDB
p-(6-Deoxy-beta-L-mannopyranosyl) ester	HMDB
Rhamnopyranose	HMDB
Rhamnosemonohydrate	HMDB
UDP-Rhamnose	HMDB
Uridine 5-pyrophosphate	HMDB
Uridine diphosphate rhamnose	HMDB
Deoxymannose	HMDB
Rhamnose, L isomer	HMDB
Rhamnose, L-isomer	HMDB
Rhamnose	MeSH, HMDB

Chemical Formula

C₆H₁₂O₅

Average Molecular Weight

164.1565

Monoisotopic Molecular Weight

164.068473494

IUPAC Name

(3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol

Traditional Name

L-(+)-rhamnose

CAS Registry Number

3615-41-6

SMILES

C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6?/m0/s1

InChI Key

SHZGCJCMOBCMKK-JFNONXLTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-rhamnose (CHEBI:62346 )
Deoxy sugars (C00507 )

Ontology

Not Available

Platelet (HMDB: HMDB0000849)

Excreta

Biofluid or Excreta

Feces (PMID: 22411374)

Cellular substructure

Cytoplasm (HMDB: HMDB0000849)

Source

Exogenous

Exogenous (HMDB: HMDB0000849)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000849)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	122 °C	Not Available
Boiling Point	398.00 to 399.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-2.459 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	827 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-1.9	ChemAxon
logS	0.7	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.38 m³·mol⁻¹	ChemAxon
Polarizability	15.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.38	31661259
DarkChem	[M-H]-	131.528	31661259
AllCCS	[M+H]+	138.008	32859911
AllCCS	[M-H]-	129.47	32859911
DeepCCS	[M+H]+	135.513	30932474
DeepCCS	[M-H]-	133.171	30932474
DeepCCS	[M-2H]-	167.69	30932474
DeepCCS	[M+Na]+	141.952	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	133.8	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	129.5	32859911
AllCCS	[M+Na-2H]-	130.8	32859911
AllCCS	[M+HCOO]-	132.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rhamnose	C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O	3151.2	Standard polar	33892256
Rhamnose	C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O	1520.7	Standard non polar	33892256
Rhamnose	C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O	1410.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rhamnose,1TMS,isomer #1	C[C@@H]1OC(O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	1482.0	Semi standard non polar	33892256
Rhamnose,1TMS,isomer #2	C[C@@H]1OC(O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1489.9	Semi standard non polar	33892256
Rhamnose,1TMS,isomer #3	C[C@@H]1OC(O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	1491.5	Semi standard non polar	33892256
Rhamnose,1TMS,isomer #4	C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1509.8	Semi standard non polar	33892256
Rhamnose,2TMS,isomer #1	C[C@@H]1OC(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1525.5	Semi standard non polar	33892256
Rhamnose,2TMS,isomer #2	C[C@@H]1OC(O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	1533.3	Semi standard non polar	33892256
Rhamnose,2TMS,isomer #3	C[C@@H]1OC(O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1550.1	Semi standard non polar	33892256
Rhamnose,2TMS,isomer #4	C[C@@H]1OC(O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	1528.7	Semi standard non polar	33892256
Rhamnose,2TMS,isomer #5	C[C@@H]1OC(O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	1549.6	Semi standard non polar	33892256
Rhamnose,2TMS,isomer #6	C[C@@H]1OC(O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1513.9	Semi standard non polar	33892256
Rhamnose,3TMS,isomer #1	C[C@@H]1OC(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	1603.9	Semi standard non polar	33892256
Rhamnose,3TMS,isomer #2	C[C@@H]1OC(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	1626.4	Semi standard non polar	33892256
Rhamnose,3TMS,isomer #3	C[C@@H]1OC(O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1608.2	Semi standard non polar	33892256
Rhamnose,3TMS,isomer #4	C[C@@H]1OC(O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1593.3	Semi standard non polar	33892256
Rhamnose,4TMS,isomer #1	C[C@@H]1OC(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1703.3	Semi standard non polar	33892256
Rhamnose,1TBDMS,isomer #1	C[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O	1732.7	Semi standard non polar	33892256
Rhamnose,1TBDMS,isomer #2	C[C@@H]1OC(O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	1758.8	Semi standard non polar	33892256
Rhamnose,1TBDMS,isomer #3	C[C@@H]1OC(O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	1746.9	Semi standard non polar	33892256
Rhamnose,1TBDMS,isomer #4	C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	1763.1	Semi standard non polar	33892256
Rhamnose,2TBDMS,isomer #1	C[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	1999.8	Semi standard non polar	33892256
Rhamnose,2TBDMS,isomer #2	C[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2006.9	Semi standard non polar	33892256
Rhamnose,2TBDMS,isomer #3	C[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2015.0	Semi standard non polar	33892256
Rhamnose,2TBDMS,isomer #4	C[C@@H]1OC(O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2011.3	Semi standard non polar	33892256
Rhamnose,2TBDMS,isomer #5	C[C@@H]1OC(O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2032.4	Semi standard non polar	33892256
Rhamnose,2TBDMS,isomer #6	C[C@@H]1OC(O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2002.0	Semi standard non polar	33892256
Rhamnose,3TBDMS,isomer #1	C[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2253.2	Semi standard non polar	33892256
Rhamnose,3TBDMS,isomer #2	C[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2271.5	Semi standard non polar	33892256
Rhamnose,3TBDMS,isomer #3	C[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2253.5	Semi standard non polar	33892256
Rhamnose,3TBDMS,isomer #4	C[C@@H]1OC(O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2276.6	Semi standard non polar	33892256
Rhamnose,4TBDMS,isomer #1	C[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2480.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Rhamnose GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-ff79aee2e9ac3a4f53c8	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Rhamnose GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-23d1bd654495aefbf615	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Rhamnose GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-ff79aee2e9ac3a4f53c8	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Rhamnose GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-23d1bd654495aefbf615	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9500000000-cfa9e0d8f1f20b29e5d8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (4 TMS) - 70eV, Positive	splash10-002r-9346400000-7524daf3b04caf0c441a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnose GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhamnose Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0019-9600000000-8cb337afbc2d297157bf	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhamnose Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0uy0-9600000000-cb7dbb4d86a5bc544704	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhamnose Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014i-9200000000-89022407246ea7a22497	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhamnose LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-03di-0900000000-2196b54a850c456b7ee8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhamnose LC-ESI-QTOF , negative-QTOF	splash10-03di-0900000000-2196b54a850c456b7ee8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhamnose 40V, Negative-QTOF	splash10-0002-3900000000-fa9bb45e13786471d8fc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhamnose 10V, Negative-QTOF	splash10-0900-4900000000-b5658046687bc01ef47f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhamnose 20V, Negative-QTOF	splash10-0a6r-9300000000-e3c74a1e2b1ad285c324	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 10V, Positive-QTOF	splash10-014i-0900000000-5daf054ff3eb9127d3ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 20V, Positive-QTOF	splash10-014j-0900000000-f7729c93b964e01cb774	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 40V, Positive-QTOF	splash10-0a70-9000000000-2c46a67befe14c31d7a9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 10V, Negative-QTOF	splash10-03di-2900000000-86321b083a11f93bb55b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 20V, Negative-QTOF	splash10-03dj-5900000000-2accd457fe7b58b9b032	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 40V, Negative-QTOF	splash10-0a4i-9000000000-9e349c8fad042f6a3e99	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 10V, Positive-QTOF	splash10-016s-0900000000-1b35b25727b809781557	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 20V, Positive-QTOF	splash10-0002-9400000000-d296c72cacbcd6d61db1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 40V, Positive-QTOF	splash10-0a4j-9000000000-daa4eb13673f38090d73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 10V, Negative-QTOF	splash10-03di-2900000000-39b12ef61b5dc955b65a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 20V, Negative-QTOF	splash10-052f-9200000000-b035b501120515e5ba70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnose 40V, Negative-QTOF	splash10-0a4i-9000000000-b4e3f8e66eccd71547b0	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Platelet

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rhamnose

METLIN ID

5812

PubChem Compound

25310

PDB ID

Not Available

ChEBI ID

62346

Food Biomarker Ontology

Not Available

VMH ID

RMN

MarkerDB ID

Not Available

Good Scents ID

rw1037731

References

Synthesis Reference

Sanchez Miguel Cambronero, Ruiz Pedro Antonio Garcia. Process for obtaining L-rhamnose of high purity from rhamnoglucosides. 1997, Patent ES2103205A1 (https://patents.google.com/patent/ES2103205A1/en)

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. [PubMed:2229345 ]
Ohri SK, Somasundaram S, Koak Y, Macpherson A, Keogh BE, Taylor KM, Menzies IS, Bjarnason I: The effect of intestinal hypoperfusion on intestinal absorption and permeability during cardiopulmonary bypass. Gastroenterology. 1994 Feb;106(2):318-23. [PubMed:8299899 ]
Miki K, Butler R, Moore D, Davidson G: Rapid and simultaneous quantification of rhamnose, mannitol, and lactulose in urine by HPLC for estimating intestinal permeability in pediatric practice. Clin Chem. 1996 Jan;42(1):71-5. [PubMed:8565237 ]
Nomura R, Nakano K, Ooshima T: Molecular analysis of the genes involved in the biosynthesis of serotype specific polysaccharide in the novel serotype k strains of Streptococcus mutans. Oral Microbiol Immunol. 2005 Oct;20(5):303-9. [PubMed:16101966 ]
Frirdich E, Whitfield C: Lipopolysaccharide inner core oligosaccharide structure and outer membrane stability in human pathogens belonging to the Enterobacteriaceae. J Endotoxin Res. 2005;11(3):133-44. [PubMed:15949142 ]
Ohse M, Matsuo M, Ishida A, Kuhara T: Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine. J Mass Spectrom. 2002 Sep;37(9):954-62. [PubMed:12271438 ]
Albers MJ, Steyerberg EW, Hazebroek FW, Mourik M, Borsboom GJ, Rietveld T, Huijmans JG, Tibboel D: Glutamine supplementation of parenteral nutrition does not improve intestinal permeability, nitrogen balance, or outcome in newborns and infants undergoing digestive-tract surgery: results from a double-blind, randomized, controlled trial. Ann Surg. 2005 Apr;241(4):599-606. [PubMed:15798461 ]
Van Kuilenburg AB, Van Lenthe H, Assmann B, Gohlich-Ratmann G, Hoffmann GF, Brautigam C, Wevers RA, Van Gennip AH: Detection of beta-ureidopropionase deficiency with HPLC-electrospray tandem mass spectrometry and confirmation of the defect at the enzyme level. J Inherit Metab Dis. 2001 Dec;24(7):725-32. [PubMed:11804209 ]
Anderson AD, Poon P, Greenway GM, MacFie J: A simple method for the analysis of urinary sucralose for use in tests of intestinal permeability. Ann Clin Biochem. 2005 May;42(Pt 3):224-6. [PubMed:15949159 ]
Whaley DN, Wiggs LS, Miller PH, Srivastava PU, Miller JM: Use of Presumpto Plates to identify anaerobic bacteria. J Clin Microbiol. 1995 May;33(5):1196-202. [PubMed:7615728 ]
Chia JS, Lin YL, Lien HT, Chen JY: Platelet aggregation induced by serotype polysaccharides from Streptococcus mutans. Infect Immun. 2004 May;72(5):2605-17. [PubMed:15102769 ]
Hosono M, Sugawara S, Ogawa Y, Kohno T, Takayanagi M, Nitta K: Purification, characterization, cDNA cloning, and expression of asialofetuin-binding C-type lectin from eggs of shishamo smelt (Osmerus [Spirinchus] lanceolatus). Biochim Biophys Acta. 2005 Sep 15;1725(2):160-73. [PubMed:16112459 ]
Bjarnason I, Smethurst P, Macpherson A, Walker F, McElnay JC, Passmore AP, Menzies IS: Glucose and citrate reduce the permeability changes caused by indomethacin in humans. Gastroenterology. 1992 May;102(5):1546-50. [PubMed:1568563 ]

Showing metabocard for Rhamnose (HMDB0000849)

MOL for HMDB0000849 (Rhamnose)

3D MOL for HMDB0000849 (Rhamnose)

3D SDF for HMDB0000849 (Rhamnose)

3D-SDF for HMDB0000849 (Rhamnose)

PDB for HMDB0000849 (Rhamnose)

3D PDB for HMDB0000849 (Rhamnose)

SMILES for HMDB0000849 (Rhamnose)

INCHI for HMDB0000849 (Rhamnose)

Structure for HMDB0000849 (Rhamnose)

3D Structure for HMDB0000849 (Rhamnose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra