Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information

Version

2.0

Creation Date

2012-05-31 14:20:52 -0600

Update Date

2015-06-03 17:19:02 -0600

Secondary Accession Numbers

ECMDB12184

Identification

Name:

Adenosyl cobinamide phosphate

Description

Adenosyl cobinamide phosphate, a known intermediate of the de novo biosynthetic pathway, is involved in Porphyrin and chlorophyll metabolism.In Salmonella typhimurium LT2, under anaerobic conditions, CobU (EC 2.7.7.62 and EC 2.7.1.156), CobT (EC 2.4.2.21), CobC (EC 3.1.3.73) and CobS (EC 2.7.8.26) catalyse reactions in the nucleotide loop

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Adenosyl cobinamide phosphoric acid
Adenosylcobinamide-P

Chemical Formula:

C₅₈H₈₅CoN₁₆O₁₄P

Weight:

Average: 1320.3013
Monoisotopic: 1319.550078214

InChI Key:

MQCMBMUJJHSGIF-QMUWONGRSA-M

InChI:

InChI=1S/C48H74N11O11P.C10H12N5O3.Co/c1-23(70-71(67,68)69)22-55-38(66)16-17-45(6)29(18-35(52)63)43-48(9)47(8,21-37(54)65)28(12-15-34(51)62)40(59-48)25(3)42-46(7,20-36(53)64)26(10-13-32(49)60)30(56-42)19-31-44(4,5)27(11-14-33(50)61)39(57-31)24(2)41(45)58-43;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h19,23,26-29,43H,10-18,20-22H2,1-9H3,(H16,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,68,69);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;4-,6-,7-,10-;/m11./s1

CAS number:

Not Available

IUPAC Name:

(3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-3,4,7,9,14,14,17,19-octamethyl-19-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide

Traditional IUPAC Name:

(3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-3,4,7,9,14,14,17,19-octamethyl-19-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide

SMILES:

C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=CN=C4N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N)OP(=O)(O)O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Metallotetrapyrroles

Direct Parent

Metallotetrapyrroles

Alternative Parents

Substituents

Metallotetrapyrrole skeleton
5'-deoxyribonucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Phosphoethanolamine
Aminopyrimidine
Monoalkyl phosphate
Phosphoric acid ester
Pyrimidine
Organic phosphoric acid derivative
N-substituted imidazole
Alkyl phosphate
Monosaccharide
Fatty amide
Fatty acyl
Imidolactam
Azole
Heteroaromatic compound
Imidazole
Pyrrolidine
Tetrahydrofuran
Pyrroline
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
1,2-diol
Azacycle
Oxacycle
Organic metal salt
Carboxylic acid derivative
Organic transition metal salt
Metalloheterocycle
Organometallic compound
Organic transition metal moeity
Organonitrogen compound
Transition metal alkyl
Organic salt
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Primary amine
Organic oxide
Alcohol
Amine
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosines (CHEBI:2481 )
O-phosphocorrinoid (CHEBI:2481 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	-0.04	ALOGPS
logP	-14	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	485.98 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	330.2 m³·mol⁻¹	ChemAxon
Polarizability	131.82 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Metabolic pathways eco01100
Porphyrin and chlorophyll metabolism ec00860

EcoCyc Pathways:

adenosylcobalamin salvage from cobinamide I COBALSYN-PWY-1

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-1492000000-cd3da96c47e731cd382e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1951000000-6afc304e19ecce421bfe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-3930000000-a2544aa4be58bc1ea4f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0089000000-e18b5ef096db2972b93e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h99-0981000000-a66bdec455b06e994738	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-1910000000-2c6dbf19ff223f6e331a	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	2481
HMDB ID	HMDB12184
Pubchem Compound ID	23724501
Kegg ID	C06509
ChemSpider ID	21864728
Wikipedia ID	Not Available
BioCyc ID	ADENOSYLCOBINAMIDE-P
EcoCyc ID	ADENOSYLCOBINAMIDE-P

Enzymes

Protein Details

1. Bifunctional adenosylcobalamin biosynthesis protein cobU

General function:: Involved in nucleotide binding
Specific function:: ATP-dependent phosphorylation of adenosylcobinamide and adds GMP to adenosylcobinamide phosphate
Gene Name:: cobU
Uniprot ID:: P0AE76
Molecular weight:: 20164

Reactions

ATP or GTP + adenosylcobinamide = adenosylcobinamide phosphate + ADP or GDP.
GTP + adenosylcobinamide phosphate = diphosphate + adenosylcobinamide-GDP.

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Adenosyl cobinamide phosphate (M2MDB000825)

Structure for #<Compound:0x6aca8f04>

Enzymes

Reactions