Cannabis Compound Database: Showing Compound Card for Protoporphyrin IX (CDB004828)

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Record Information

Version

1.0

Created at

2020-04-17 18:40:57 UTC

Updated at

2020-12-07 19:11:03 UTC

CannabisDB ID

CDB004828

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Protoporphyrin IX

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). Protoporphyrin IX is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₃₄H₃₄N₄O₄

Average Molecular Weight

562.66

Monoisotopic Molecular Weight

562.258

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

Traditional 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

CAS Registry Number

553-12-8

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

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

Chemical Taxonomy

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:

Role

Indirect biological role:

Biological role:

Metabolite

Industrial application:

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.17 mg/mL at 25 °C	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Protoporphyrin IX, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uxu-1000290000-e22236fe3cca8eed1ecf	Spectrum
Predicted GC-MS	Protoporphyrin IX, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6000094000-b9c12952e100c5144cab	Spectrum
Predicted GC-MS	Protoporphyrin IX, "Protoporphyrin IX,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Protoporphyrin IX, 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

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Porphyrin Metabolism
Acute Intermittent Porphyria		Not Available
Porphyria Variegata (PV)		Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease		Not Available
Hereditary Coproporphyria (HCP)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Coproporphyrinogen-III oxidase, mitochondrial	CPOX	3q12	P36551	details
Protoporphyrinogen oxidase	PPOX	1q22	P50336	details
Ferrochelatase, mitochondrial	FECH	18q21.3	P22830	details
Ferrochelatase			Q53FU1	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Ferritin light chain	FTL	19q13.33	P02792	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000241

DrugBank ID

DB02285

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Protoporphyrin_IX

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15430

References

General References

Not Available

Enzymes

Enzyme Details

1. Coproporphyrinogen-III oxidase, mitochondrial

General function:: Involved in coproporphyrinogen oxidase activity
Specific function:: Key enzyme in heme biosynthesis. Catalyzes the oxidative decarboxylation of propionic acid side chains of rings A and B of coproporphyrinogen III.
Gene Name:: CPOX
Uniprot ID:: P36551
Molecular weight:: 50151.605

Enzyme Details

2. Protoporphyrinogen oxidase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX.
Gene Name:: PPOX
Uniprot ID:: P50336
Molecular weight:: 50764.8

Enzyme Details

3. Ferrochelatase, mitochondrial

General function:: Involved in ferrochelatase activity
Specific function:: Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name:: FECH
Uniprot ID:: P22830
Molecular weight:: 47861.77

Enzyme Details

4. Ferrochelatase

General function:: Involved in ferrochelatase activity
Specific function:: Catalyzes the ferrous insertion into protoporphyrin IX
Gene Name:: Not Available
Uniprot ID:: Q53FU1
Molecular weight:: 47488.3

Showing Compound Card for Protoporphyrin IX (CDB004828)

Structure for CDB004828 (Protoporphyrin IX)

Enzymes