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protoheme IX

PubChem CID
444097
Structure
protoheme IX_small.png
protoheme IX_3D_Structure.png
Molecular Formula
Synonyms
  • heme
  • protoheme
  • protoheme IX
  • Haem
  • heme b
Molecular Weight
616.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-25
Description
Heme is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Heme is a metabolite found in or produced by Saccharomyces cerevisiae.
Protoheme IX is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
protoheme IX.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[18-(2-carboxyethyl)-7,12-bis(ethenyl)-3,8,13,17-tetramethylporphyrin-21,23-diid-2-yl]propanoic acid;iron(2+)
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

KABFMIBPWCXCRK-UHFFFAOYSA-L
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=C(C2=CC3=NC(=CC4=C(C(=C([N-]4)C=C5C(=C(C(=N5)C=C1[N-]2)C=C)C)C=C)C)C(=C3CCC(=O)O)C)CCC(=O)O.[Fe+2]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C34H32FeN4O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

14875-96-8

2.3.2 Deprecated CAS

2234266-27-2, 69344-57-6, 75197-11-4, 86-11-3

2.3.3 European Community (EC) Number

2.3.4 DSSTox Substance ID

2.3.5 KEGG ID

2.3.6 Metabolomics Workbench ID

2.3.7 NCI Thesaurus Code

2.3.8 Pharos Ligand ID

2.3.9 Wikidata

2.3.10 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Ferroprotoporphyrin
  • Haem
  • Heme
  • Heme b
  • Protoheme
  • Protoheme IX

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
616.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
616.177291 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
616.177291 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
101 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
43
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1580
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

5 Chemical Vendors

6 Pharmacology and Biochemistry

6.1 Biochemical Reactions

7 Use and Manufacturing

7.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
Ferrate(2-), [7,12-diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoato(4-)-.kappa.N21,.kappa.N22,.kappa.N23,.kappa.N24]-, hydrogen (1:2), (SP-4-2)-: INACTIVE

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Thieme References

8.4 Chemical Co-Occurrences in Literature

8.5 Chemical-Gene Co-Occurrences in Literature

8.6 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Chemical Co-Occurrences in Patents

9.2 Chemical-Disease Co-Occurrences in Patents

9.3 Chemical-Gene Co-Occurrences in Patents

10 Interactions and Pathways

10.1 Protein Bound 3D Structures

10.2 Pathways

11 Classification

11.1 MeSH Tree

11.2 KEGG: Metabolite

11.3 EPA DSSTox Classification

11.4 EPA TSCA and CDR Classification

12 Information Sources

  1. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  2. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  3. EPA Chemicals under the TSCA
    Ferrate(2-), [7,12-diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoato(4-)-.kappa.N21,.kappa.N22,.kappa.N23,.kappa.N24]-, hydrogen (1:2), (SP-4-2)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    Ferrate(2-), [7,12-diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoato(4-)-κN21,κN22,κN23,κN24]-, hydrogen (1:2), (SP-4-2)-
    https://echa.europa.eu/substance-information/-/substanceinfo/100.114.904
  6. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  7. Metabolomics Workbench
  8. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  9. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  10. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  11. Wikidata
  12. Wikipedia
  13. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  14. PubChem
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