Showing Compound Card for Heme (CDB005175)

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Record Information
Version1.0
Created at2020-04-17 19:16:52 UTC
Updated at2020-11-18 16:39:28 UTC
CannabisDB IDCDB005175
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHeme
DescriptionHeme is also known as protoheme or [fe(ppix)]. Heme is a weakly acidic compound (based on its pKa). Heme exists in all living organisms, ranging from bacteria to humans. In humans, heme is involved in ibuprofen action pathway. Outside of the human body, Heme has been detected, but not quantified in, several different foods, such as triticales, chicories, quinces, black mulberries, and japanese walnuts. This could make heme a potential biomarker for the consumption of these foods. Heme in which the iron has oxidation state +2. Heme is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2-)]iron(II)ChEBI
[Fe(ppix)]ChEBI
Fe(ppix)ChEBI
FerroprotohemeChEBI
Ferroprotoporphyrin IXChEBI
Ferrous protohemeChEBI
Ferrous protoheme IXChEBI
HaemChEBI
Iron(II) protoporphyrin IXChEBI
ProtoferrohemeChEBI
ProtohemeChEBI
Heme bKegg
Protoheme IXKegg
HemeChEBI
Chemical FormulaC34H32FeN4O4
Average Molecular Weight616.49
Monoisotopic Molecular Weight616.1773
IUPAC Name4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
Traditional Name4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
CAS Registry Number14875-96-8
SMILES
CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=O
InChI Identifier
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/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
InChI KeyKABFMIBPWCXCRK-RGGAHWMASA-L
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1ALOGPS
logP2.19ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.22 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity169.77 m³·mol⁻¹ChemAxon
Polarizability69.44 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHeme, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHeme, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHeme, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHeme, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHeme, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHeme, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHeme, "Heme,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Cytochrome b-c1 complex subunit 9UQCR1022cen-q12.3Q9UDW1 details
Cytochrome b-c1 complex subunit 6, mitochondrialUQCRH1p34.1P07919 details
Protein AMBPAMBP9q32-q33P02760 details
Calcium-activated potassium channel subunit alpha-1KCNMA110q22.3Q12791 details
Proton-coupled folate transporterSLC46A117q11.2Q96NT5 details
ATP-binding cassette sub-family B member 6, mitochondrialABCB62q36Q9NP58 details
ATP-binding cassette sub-family B member 7, mitochondrialABCB7O75027 details
ATP-binding cassette sub-family B member 10, mitochondrialABCB101q42.13Q9NRK6 details
Heme transporter HRG1SLC48A112q13.11Q6P1K1 details
Metal Bindings
Receptors
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrialCYP27B112q13.1-q13.3O15528 details
Guanylate cyclase soluble subunit beta-1GUCY1B34q31.3-q33Q02153 details
Prostacyclin synthasePTGIS20q13.13Q16647 details
25-hydroxycholesterol 7-alpha-hydroxylaseCYP7B18q21.3O75881 details
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrialCYP24A120q13Q07973 details
Feline leukemia virus subgroup C receptor-related protein 1FLVCR11q32.3Q9Y5Y0 details
Scavenger receptor cysteine-rich type 1 protein M130CD16312p13.3Q86VB7 details
Peroxidasin homologPXDN2p25Q92626 details
Membrane-associated progesterone receptor component 1PGRMC1O00264 details
Membrane-associated progesterone receptor component 2PGRMC24q26O15173 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Heme oxygenase 1HMOX122q13.1P09601 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Prostacyclin synthasePTGIS20q13.13Q16647 details
CatalaseCAT11p13P04040 details
PR domain zinc finger protein 2PRDM21p36.21Q13029 details
Transcription factor NF-E2 45 kDa subunitNFE212q13Q16621 details
Nuclear factor erythroid 2-related factor 1NFE2L117q21.3Q14494 details
Concentrations Data
Not Available
HMDB IDHMDB0003178
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031136
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00032
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeme
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17627
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 227 proteins in total.

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Enzymes

Enzyme Details
1. 5-aminolevulinate synthase, erythroid-specific, mitochondrial
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS2
Uniprot ID:
P22557
Molecular weight:
64632.86
Enzyme Details
2. 5-aminolevulinate synthase, nonspecific, mitochondrial
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS1
Uniprot ID:
P13196
Molecular weight:
70580.325
Enzyme Details
3. Succinate dehydrogenase cytochrome b560 subunit, mitochondrial
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHC
Uniprot ID:
Q99643
Molecular weight:
16650.185
Enzyme Details
4. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Enzyme Details
5. Heme oxygenase 2
General function:
Involved in heme oxygenase (decyclizing) activity
Specific function:
Heme oxygenase cleaves the heme ring at the alpha methene bridge to form biliverdin. Biliverdin is subsequently converted to bilirubin by biliverdin reductase. Under physiological conditions, the activity of heme oxygenase is highest in the spleen, where senescent erythrocytes are sequestrated and destroyed. Heme oxygenase 2 could be implicated in the production of carbon monoxide in brain where it could act as a neurotransmitter.
Gene Name:
HMOX2
Uniprot ID:
P30519
Molecular weight:
36032.615
Enzyme Details
6. Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial
General function:
Involved in iron ion binding
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q) (By similarity).
Gene Name:
SDHD
Uniprot ID:
O14521
Molecular weight:
17042.82
Enzyme Details
7. NADPH--cytochrome P450 reductase
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:
POR
Uniprot ID:
P16435
Molecular weight:
77047.575
Enzyme Details
8. Heme oxygenase 1
General function:
Involved in heme oxygenase (decyclizing) activity
Specific function:
Heme oxygenase cleaves the heme ring at the alpha methene bridge to form biliverdin. Biliverdin is subsequently converted to bilirubin by biliverdin reductase. Under physiological conditions, the activity of heme oxygenase is highest in the spleen, where senescent erythrocytes are sequestrated and destroyed.
Gene Name:
HMOX1
Uniprot ID:
P09601
Molecular weight:
32818.345
Enzyme Details
9. Uroporphyrinogen decarboxylase
General function:
Involved in uroporphyrinogen decarboxylase activity
Specific function:
Catalyzes the decarboxylation of four acetate groups of uroporphyrinogen-III to yield coproporphyrinogen-III.
Gene Name:
UROD
Uniprot ID:
P06132
Molecular weight:
40786.58
Enzyme Details
10. 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

Transporters

Enzyme Details
1. Nitric oxide synthase, inducible
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
Enzyme Details
2. Cytochrome b-c1 complex subunit 9
General function:
Involved in ubiquinol-cytochrome-c reductase activity
Specific function:
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain. This subunit interacts with cytochrome c1
Gene Name:
UQCR10
Uniprot ID:
Q9UDW1
Molecular weight:
7308.4
Enzyme Details
3. Cytochrome b-c1 complex subunit 6, mitochondrial
General function:
Involved in ubiquinol-cytochrome-c reductase activity
Specific function:
This is a component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain. This protein may mediate formation of the complex between cytochromes c and c1
Gene Name:
UQCRH
Uniprot ID:
P07919
Molecular weight:
10738.7
Enzyme Details
4. Protein AMBP
General function:
Involved in transporter activity
Specific function:
Trypstatin is a trypsin inhibitor
Gene Name:
AMBP
Uniprot ID:
P02760
Molecular weight:
38999.2
Enzyme Details
5. Calcium-activated potassium channel subunit alpha-1
General function:
Involved in ion channel activity
Specific function:
Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activation dampens the excitatory events that elevate the cytosolic Ca(2+) concentration and/or depolarize the cell membrane. It therefore contributes to repolarization of the membrane potential. Plays a key role in controlling excitability in a number of systems, such as regulation of the contraction of smooth muscle, the tuning of hair cells in the cochlea, regulation of transmitter release, and innate immunity. In smooth muscles, its activation by high level of Ca(2+), caused by ryanodine receptors in the sarcoplasmic reticulum, regulates the membrane potential. In cochlea cells, its number and kinetic properties partly determine the characteristic frequency of each hair cell and thereby helps to establish a tonotopic map. Kinetics of KCNMA1 channels are determined by alternative splicing, phosphorylation status and its combination with modulating beta subunits. Highly sensitive to both iberiotoxin (IbTx) and charybdotoxin (CTX)
Gene Name:
KCNMA1
Uniprot ID:
Q12791
Molecular weight:
137558.1
Enzyme Details
6. Proton-coupled folate transporter
General function:
Involved in transmembrane transport
Specific function:
Has been shown to act both as an intestinal proton- coupled high-affinity folate transporter and as an intestinal heme transporter which mediates heme uptake from the gut lumen into duodenal epithelial cells. The iron is then released from heme and may be transported into the bloodstream. Dietary heme iron is an important nutritional source of iron. Shows a higher affinity for folate than heme
Gene Name:
SLC46A1
Uniprot ID:
Q96NT5
Molecular weight:
49770.0
Enzyme Details
7. ATP-binding cassette sub-family B member 6, mitochondrial
General function:
Involved in ATP binding
Specific function:
Binds heme and porphyrins and functions in their ATP- dependent uptake into the mitochondria. Plays a crucial role in heme synthesis
Gene Name:
ABCB6
Uniprot ID:
Q9NP58
Molecular weight:
93884.7
Enzyme Details
8. ATP-binding cassette sub-family B member 7, mitochondrial
General function:
Involved in ATP binding
Specific function:
Could be involved in the transport of heme from the mitochondria to the cytosol. Plays a central role in the maturation of cytosolic iron-sulfur (Fe/S) cluster-containing proteins
Gene Name:
ABCB7
Uniprot ID:
O75027
Molecular weight:
82640.6
Enzyme Details
9. ATP-binding cassette sub-family B member 10, mitochondrial
General function:
Involved in ATP binding
Specific function:
May mediate critical mitochondrial transport functions related to heme biosynthesis
Gene Name:
ABCB10
Uniprot ID:
Q9NRK6
Molecular weight:
79146.9
Enzyme Details
10. Heme transporter HRG1
General function:
Involved in transport
Specific function:
Heme transporter that regulates intracellular heme availability through the endosomal or lysosomal compartment.
Gene Name:
SLC48A1
Uniprot ID:
Q6P1K1
Molecular weight:
16419.045

Only showing the first 10 proteins. There are 227 proteins in total.

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