Showing Compound Protoporphyrinogen IX (FDB022425)

Record Information

Version

1.0

Creation date

2011-09-21 00:13:48 UTC

Update date

2019-11-26 03:21:03 UTC

Primary ID

FDB022425

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Protoporphyrinogen IX

Description

Protoporphyrinogen IX is an intermediate in heme biosynthesis. It is a porphyrinogen in which 2 pyrrole rings each have one methyl and one propionate side chain and the other two pyrrole rings each have one methyl and one vinyl side chain. 15 isomers are possible but only one, type IX, occurs naturally. Protoporphyrinogen is produced by oxidative decarboxylation of coproporphyrinogen. [HMDB]. Protoporphyrinogen IX is found in many foods, some of which are elderberry, grapefruit, green vegetables, and pepper (c. annuum).

CAS Number

7412-77-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
5,10,15,20,22,24-Hexahydro protoporphyrin IX deriv.	HMDB
5,10,15,20,22,24-hexahydro protoporphyrin IX deriv.	hmdb
7,12-Diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoate	Generator
7,12-diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoate	hmdb
7,12-Diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoic acid	ChEBI
7,12-diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoic acid	hmdb
7,12-Diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoate	HMDB
7,12-diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21h,23h-porphine-2,18-dipropanoate	hmdb
7,12-Diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid	HMDB
7,12-diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21h,23h-porphine-2,18-dipropanoic acid	hmdb

Showing 1 to 10 of 14 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0055 g/L	ALOGPS
logP	3.44	ALOGPS
logP	6.2	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	137.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	169.42 m³·mol⁻¹	ChemAxon
Polarizability	64.52 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C34H40N4O4

IUPAC name

3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

InChI Identifier

InChI=1S/C34H40N4O4/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/h7-8,35-38H,1-2,9-16H2,3-6H3,(H,39,40)(H,41,42)

InChI Key

UHSGPDMIQQYNAX-UHFFFAOYSA-N

Isomeric SMILES

CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3

Average Molecular Weight

568.7058

Monoisotopic Molecular Weight

568.304955788

Classification

Description

Belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Porphyrins

Direct Parent

Porphyrins

Alternative Parents

Substituents

Porphyrin
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Azacycle
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

porphyrinogens (CHEBI:15435 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Organ and components:

Liver

Tissue and substructures:

Placenta

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Acute intermittent porphyria

Role

Indirect biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Protoporphyrinogen IX, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0pi3-1000190000-2785151d048ffcfdafc1	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00bc-9000053000-45009d4bbcc7a57d2e8b	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, "Protoporphyrinogen IX,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrinogen IX, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000190000-7c4ce83e3be73bfccdf6	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pi0-0000490000-affa2d20d85ce7a5a2a1	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dj-0020900000-a1714c4d96457c66da57	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-4148fa37b5b91e3b5a92	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05tb-1000090000-27a9f5ba745bc29e2b22	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000260000-392765703d0911aa98fc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0000090000-9a1be7ce809937d54938	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ldi-0000190000-1a53eff6b6eaea2bd1a8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0000790000-030a68500ee48fd68e34	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-0000090000-4f79e644c71d1a64565b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0000090000-8599f24133cbc58316eb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1000950000-a5525829d1d51b8650b0	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

108741

ChEMBL ID

Not Available

KEGG Compound ID

C01079

Pubchem Compound ID

121893

Pubchem Substance ID

Not Available

ChEBI ID

15435

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01097

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

36764

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Protoporphyrinogen IX

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Protoporphyrinogen IX (FDB022425)

Structure for FDB022425 (Protoporphyrinogen IX)