Cobinamide (ECMDB06902) (M2MDB000705)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:10:12 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-17 15:41:21 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Cobinamide | |||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Cobinamide is an intermediate in porphyrin and chlorophyll metabolism. It is converted to adenosyl cobinamide via the enzyme cob(I)alamin adenosyltransferase [EC:2.5.1.17]. Adenosyl cobinamide is the third to last step in the synthesis of vitamin B12 coenzyme. | |||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C48H72CoN11O8 | |||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 990.0874 Monoisotopic: 989.489733529 | |||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | FEESAGIUMZGLMF-JFYQDRLCSA-M | |||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C48H73N11O8.Co/c1-23(60)22-55-38(67)16-17-45(6)29(18-35(52)64)43-48(9)47(8,21-37(54)66)28(12-15-34(51)63)40(59-48)25(3)42-46(7,20-36(53)65)26(10-13-32(49)61)30(56-42)19-31-44(4,5)27(11-14-33(50)62)39(57-31)24(2)41(45)58-43;/h19,23,26-29,43,60H,10-18,20-22H2,1-9H3,(H14,49,50,51,52,53,54,55,56,57,58,59,61,62,63,64,65,66,67);/q;+3/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;/m1./s1 | |||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 13497-85-3 | |||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | C[C@@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co++])\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 | |||||||||||||||||||||||||||||||||||||||||||||||||||
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 |
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Substituents |
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Molecular Framework | Aliphatic heteropolycyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 2 | |||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Water + Cobinamide > ADP + Cobinamide + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Cobinamide > ADP + Cobinamide + Hydrogen ion + Phosphate Adenosine triphosphate + Cobinamide + Hydrogen ion <> Adenosyl cobinamide + Triphosphate Adenosine triphosphate + Cobinamide <> Triphosphate + Adenosyl cobinamide Adenosine triphosphate + Cobinamide > Triphosphate + Adenosyl cobinamide Adenosine triphosphate + Cob(I)yrinate a,c diamide + Cobinamide <> Triphosphate + Adenosyl cobyrinate a,c diamide + Adenosyl cobinamide Cobinamide + Adenosine triphosphate + Cobinamide > Adenosyl cobinamide + Triphosphate + Adenosyl cobinamide + Triphosphate Cobinamide + Adenosine triphosphate + Water + Cobinamide > Adenosine diphosphate + Phosphate + Hydrogen ion + Cobinamide + ADP | |||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Responsible for energy coupling to the transport system
- Gene Name:
- btuD
- Uniprot ID:
- P06611
- Molecular weight:
- 27081
Reactions
ATP + H(2)O + vitamin B12(Out) = ADP + phosphate + vitamin B12(In). |
- General function:
- Involved in ATP binding
- Specific function:
- Required for both de novo synthesis of the corrin ring for the assimilation of exogenous corrinoids. Participates in the adenosylation of a variety of incomplete and complete corrinoids
- Gene Name:
- btuR
- Uniprot ID:
- P0A9H5
- Molecular weight:
- 21999
Reactions
ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide. |
ATP + cobinamide = triphosphate + adenosylcobinamide. |
- General function:
- Involved in ATP binding
- Specific function:
- Converts CNB12 to ADOB12
- Gene Name:
- eutT
- Uniprot ID:
- P65643
- Molecular weight:
- 30171
Reactions
ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide. |
ATP + cobinamide = triphosphate + adenosylcobinamide. |
- General function:
- Involved in cobalamin transport
- Specific function:
- Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Involved in the translocation of the substrate across the membrane
- Gene Name:
- btuC
- Uniprot ID:
- P06609
- Molecular weight:
- 34949
- General function:
- Involved in binding
- Specific function:
- Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Binds vitamin B12 and delivers it to the periplasmic surface of BtuC
- Gene Name:
- btuF
- Uniprot ID:
- P37028
- Molecular weight:
- 29367
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Responsible for energy coupling to the transport system
- Gene Name:
- btuD
- Uniprot ID:
- P06611
- Molecular weight:
- 27081
Reactions
ATP + H(2)O + vitamin B12(Out) = ADP + phosphate + vitamin B12(In). |
- General function:
- Involved in cobalamin transport
- Specific function:
- Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Involved in the translocation of the substrate across the membrane
- Gene Name:
- btuC
- Uniprot ID:
- B1XG18
- Molecular weight:
- 34949
- General function:
- Involved in receptor activity
- Specific function:
- Involved in the active translocation of vitamin B12 (cyanocobalamin) across the outer membrane to the periplasmic space. It derives its energy for transport by interacting with the trans-periplasmic membrane protein tonB. Is also a receptor for bacteriophages BF23 and C1, and for A and E colicins
- Gene Name:
- btuB
- Uniprot ID:
- P06129
- Molecular weight:
- 68407
- General function:
- Involved in cobalamin transport
- Specific function:
- Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Involved in the translocation of the substrate across the membrane
- Gene Name:
- btuC
- Uniprot ID:
- P06609
- Molecular weight:
- 34949
- General function:
- Involved in binding
- Specific function:
- Part of the ABC transporter complex BtuCDF involved in vitamin B12 import. Binds vitamin B12 and delivers it to the periplasmic surface of BtuC
- Gene Name:
- btuF
- Uniprot ID:
- P37028
- Molecular weight:
- 29367
- General function:
- Involved in protein transporter activity
- Specific function:
- Involved in the tonB-dependent energy-dependent transport of various receptor-bound substrates. Protects exbD from proteolytic degradation and functionally stabilizes tonB
- Gene Name:
- exbB
- Uniprot ID:
- P0ABU7
- Molecular weight:
- 26287
- General function:
- Involved in transporter activity
- Specific function:
- Involved in the tonB-dependent energy-dependent transport of various receptor-bound substrates
- Gene Name:
- exbD
- Uniprot ID:
- P0ABV2
- Molecular weight:
- 15527
- General function:
- Involved in iron ion transmembrane transporter activity
- Specific function:
- Interacts with outer membrane receptor proteins that carry out high-affinity binding and energy dependent uptake into the periplasmic space of specific substrates such as cobalamin, and various iron compounds (such as iron dicitrate, enterochelin, aerobactin, etc.). In the absence of tonB these receptors bind their substrates but do not carry out active transport. TonB also interacts with some colicins and is involved in the energy- dependent, irreversible steps of bacteriophages phi 80 and T1 infection. It could act to transduce energy from the cytoplasmic membrane to specific energy-requiring processes in the outer membrane, resulting in the release into the periplasm of ligands bound by these outer membrane proteins
- Gene Name:
- tonB
- Uniprot ID:
- P02929
- Molecular weight:
- 26094