Showing Compound Protoporphyrin (FDB004277)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:10 UTC

Update date

2020-09-17 15:38:30 UTC

Primary ID

FDB004277

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Protoporphyrin

Description

Protoporphyrin IX, also known as porphyrinogen IX or H2PPIX, 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. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, and hereditary coproporphyria (HCP). Protoporphyrin IX is a strong basic compound (based on its pKa). Protoporphyrin IX exists in all living species, ranging from bacteria to humans. Outside of the human body, Protoporphyrin IX has been detected, but not quantified in, red beetroots. This could make protoporphyrin IX a potential biomarker for the consumption of these foods. Protoporphyrin IX is a potentially toxic compound. There are several types of porphyrias (most are inherited). The enzyme ferrochelatase converts it into heme. Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth).

CAS Number

553-12-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid	ChEBI
3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid	ChEBI
H2PpIX	ChEBI
Kammerer's prophyrin	ChEBI
Ooporphyrin	ChEBI
Porphyrinogen IX	ChEBI
3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionate	Generator
3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoate	Generator
3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di	HMDB
PpIX	HMDB
Protoporphyrin	HMDB
Protoporphyrin-"ix"	HMDB
Protoporphyrin-IX	HMDB
Lebersdan	manual
Protoporphyrin IX	ChEBI
Protoporphyrin IX (6CI)	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	4.4	ALOGPS
logP	6.78	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	4.96	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	131.96 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	163.81 m³·mol⁻¹	ChemAxon
Polarizability	66.03 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

C34H34N4O4

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(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid

InChI Identifier

InChI=1S/C34H34N4O4/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/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

InChI Key

KSFOVUSSGSKXFI-UJJXFSCMSA-N

Isomeric SMILES

CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O

Average Molecular Weight

562.6582

Monoisotopic Molecular Weight

562.258005596

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

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Ontology

Ingestion

Source:

Biological:

Plant

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Acute intermittent porphyria

Role

Indirect biological role:

Biological role:

Metabolite

Industrial application:

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Reddish-purple cryst.	CCD
Mass Composition	C 72.58%; H 6.09%; N 9.96%; O 11.37%	CCD
Melting Point	Mp 300°	CCD
Boiling Point	Not Available
Experimental Water Solubility	0.169 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[neutral]?max557;582;602 ( dication, aq. HCl)	CCD
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Protoporphyrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uxu-1000290000-e22236fe3cca8eed1ecf	Spectrum
Predicted GC-MS	Protoporphyrin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6000094000-b9c12952e100c5144cab	Spectrum
Predicted GC-MS	Protoporphyrin, "Protoporphyrin IX,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin, TBDMS_2_6, 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	splash10-0002-0000090000-5d5be53410134c5719ab	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-1000590000-2d4157b9f73534d95a9c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-1000910000-07524a9291a1921dfafc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000090000-5df26c1cfb9a0b16a91a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0296-1000190000-2d4bcb49201fc10adc09	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000230000-064fb944a966d08c06bf	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000090000-87c1740ecd1a28f4a2d9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xu-0000590000-99160b987bb7e62ab362	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0000900000-f2d9118441a9c8c47d79	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-0000090000-d428ac6dc2fc4794cc41	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0j4j-0000090000-2b065966ec57bb97d511	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-1000970000-b435817e4dc349e65ab3	2021-09-23	View Spectrum