ChemFOnt: Showing chemical card for UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine (CFc000338019)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:32:12 UTC

Chemfont ID

CFc000338019

Molecule Identification

Common Name

UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine

Definition

Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine can be found in a number of food items such as chickpea, pineapple, sea-buckthornberry, and savoy cabbage, which makes udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine a potential biomarker for the consumption of these food products. Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine may be a unique E.coli metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-alpha-D-glucosamine	ChEBI
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-a-D-glucosamine	Generator
UDP-3-O-[(3R)-3-Hydroxytetradecanoyl]-α-D-glucosamine	Generator

Chemical Formula

C₂₉H₅₀N₃O₁₈P₂

Average Molecular Weight

790.6641

Monoisotopic Molecular Weight

790.256459835

IUPAC Name

1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-olate

Traditional Name

1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-oxopyrimidin-4-olate

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@]1([H])[C@@]([H])(N)[C@@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)O[C@]([H])(CO)[C@@]1([H])O

InChI Identifier

InChI=1S/C29H51N3O18P2/c1-2-3-4-5-6-7-8-9-10-11-17(34)14-21(36)48-26-22(30)28(47-18(15-33)24(26)38)49-52(43,44)50-51(41,42)45-16-19-23(37)25(39)27(46-19)32-13-12-20(35)31-29(32)40/h12-13,17-19,22-28,33-34,37-39H,2-11,14-16,30H2,1H3,(H,41,42)(H,43,44)(H,31,35,40)/p-1/t17-,18-,19-,22-,23-,24-,25-,26-,27-,28-/m1/s1

InChI Key

ZFPNNOXCEDQJQS-SSVOXRMNSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Saccharolipid
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Beta-hydroxy acid
Fatty acid ester
Pyrimidone
Amino saccharide
Hydropyrimidine
Hydroxy acid
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Fatty acyl
Pyrimidine
Alkyl phosphate
Tetrahydrofuran
Vinylogous amide
Heteroaromatic compound
Urea
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Lactam
Azacycle
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Amine
Alcohol
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Primary alcohol
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-3-O-[(3R)-3-hydroxytetradecanoyl]-D-glucosamine(1-) (CHEBI:71573 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Lipopolysaccharide Biosynthesis (PathBank: SMP0121299)
Lipopolysaccharide Biosynthesis II (PathBank: SMP0122112)
Lipopolysaccharide Biosynthesis III (PathBank: SMP0122237)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.66 g/L	ALOGPS
logP	0.5	ALOGPS
logP	-1.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.72	ChemAxon
pKa (Strongest Basic)	8.47	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	329.95 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	184.89 m³·mol⁻¹	ChemAxon
Polarizability	75.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0304525

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031238

KNApSAcK ID

Not Available

Chemspider ID

28533665

KEGG Compound ID

Not Available

BioCyc ID

UDP-OHMYR-GLUCOSAMINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

71573

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine (CFc000338019)

MOL for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

3D MOL for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

3D SDF for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

3D-SDF for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

PDB for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

3D PDB for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

SMILES for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

INCHI for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

Structure for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)

3D Structure for CFc000338019 (UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine)