Cannabis Compound Database: Showing Compound Card for FADH (CDB005093)

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Record Information

Version

1.0

Created at

2020-04-17 19:08:37 UTC

Updated at

2020-11-18 16:39:20 UTC

CannabisDB ID

CDB005093

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

FADH

Description

FADH, also known as 1,5-dihydro-fad or FADH2, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FADH is a strong basic compound (based on its pKa). FADH exists in all living species, ranging from bacteria to humans. In humans, FADH is involved in lps and citrate signaling and inflammation. Outside of the human body, FADH has been detected, but not quantified in, several different foods, such as thistles, white lupines, grass pea, deerberries, and passion fruits. This could make FADH a potential biomarker for the consumption of these foods. FADH 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
1,5-Dihydro-fad	ChEBI
DIHYDROFLAVINE-adenine dinucleotide	ChEBI
Flavin adenine dinucleotide (reduced)	ChEBI
1,5-Dihydro-p-5-ester with adenosine	HMDB
1,5-Dihydro-riboflavin 5'-(trihydrogen diphosphate) p'->5'-ester with adenosine	HMDB
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine	HMDB
Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine	HMDB
Adenosine 5'-{3-[D-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate}	HMDB
Adenosine 5-(trihydrogen pyrophosphate)	HMDB
Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine	HMDB
Adenosine pyrophosphate, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine	HMDB
Adenosine pyrophosphate, 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine	HMDB
Benzo[GR]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv	HMDB
Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv	HMDB
Dihydro-fad	HMDB
FADH2	HMDB
FDA	HMDB
Flavin adenine dinucleotide reduced	HMDB
Reduced flavine adenine dinucleotide	HMDB

Chemical Formula

C₂₇H₃₅N₉O₁₅P₂

Average Molecular Weight

787.57

Monoisotopic Molecular Weight

787.1728

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Traditional Name

fadh(.)

CAS Registry Number

1910-41-4

SMILES

CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=C(N2)C(=O)NC(=O)N1

InChI Identifier

InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1

InChI Key

YPZRHBJKEMOYQH-UYBVJOGSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Flavin nucleotides

Sub Class

Not Available

Direct Parent

Flavin nucleotides

Alternative Parents

Substituents

Flavin nucleotide
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Flavin
Pentose phosphate
Pentose-5-phosphate
Alkyldiarylamine
Glycosyl compound
N-glycosyl compound
6-aminopurine
Organic pyrophosphate
Pentose monosaccharide
Pteridine
Monosaccharide phosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Pyrimidone
Imidolactam
Benzenoid
Phosphoric acid ester
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Pyrimidine
Alkyl phosphate
Azole
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Vinylogous amide
Urea
Lactam
Secondary alcohol
Secondary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Polyol
Primary amine
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin adenine dinucleotide (CHEBI:17877 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	-1.336	Wikipedia

Predicted Properties

Property	Value	Source
logP	-0.23	ALOGPS
logP	-4.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	355.76 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	188.8 m³·mol⁻¹	ChemAxon
Polarizability	69.69 Å³	ChemAxon
Number of Rings	6	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	FADH, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g70-0024960400-5de09e4bdf0187b78529	Spectrum
Predicted GC-MS	FADH, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	FADH, TMS_1_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0001200900-b0740b3d33d50996ccde	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000m-0105900000-3abff26d5bb35f8527b8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-0931700000-73f360589a13230eea7a	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0932110400-58a2ec43460cf9df1c4d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0930000000-15d7e9b22a8286323cc5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0960000000-64746c5025e9c53c89b3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0159-1675510900-39158f1ef2e33daa689e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-4940100000-64cc07487da7b6c45ba2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7i-4900000000-4da9166c58a097f7d7ef	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0104000900-487b1a93da5295026592	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0964110400-9a24ca36f159cc16d182	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052u-0693100000-d2fe9957910ae7607fd3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-5c202a395443de89e132	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-005i-9611010700-e3e8cae89c8f03508db4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05r0-9735640500-89a663c6bc64f3d8f9f1	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Citric Acid Cycle
Glycerol Phosphate Shuttle		Not Available
Congenital lactic acidosis		Not Available
Fumarase deficiency		Not Available
Mitochondrial complex II deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Long-chain specific acyl-CoA dehydrogenase, mitochondrial	ACADL	2q34	P28330	details
Short-chain specific acyl-CoA dehydrogenase, mitochondrial	ACADS	12q24.31	P16219	details
Medium-chain specific acyl-CoA dehydrogenase, mitochondrial	ACADM	1p31	P11310	details
Peroxisomal acyl-coenzyme A oxidase 1	ACOX1	17q25.1	Q15067	details
Heme oxygenase 2	HMOX2	16p13.3	P30519	details
Isovaleryl-CoA dehydrogenase, mitochondrial	IVD	15q14-q15	P26440	details
Peroxisomal acyl-coenzyme A oxidase 3	ACOX3	4p15.3	O15254	details
Glycerol-3-phosphate dehydrogenase, mitochondrial	GPD2	2q24.1	P43304	details
Heme oxygenase 1	HMOX1	22q13.1	P09601	details
Glutaryl-CoA dehydrogenase, mitochondrial	GCDH	19p13.2	Q92947	details
Flavin reductase (NADPH)	BLVRB	19q13.1-q13.2	P30043	details
Short/branched chain specific acyl-CoA dehydrogenase, mitochondrial	ACADSB	10q26.13	P45954	details
L-2-hydroxyglutarate dehydrogenase, mitochondrial	L2HGDH	14q21.3	Q9H9P8	details
Very long-chain specific acyl-CoA dehydrogenase, mitochondrial	ACADVL	17p13.1	P49748	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Heme oxygenase 2	HMOX2	16p13.3	P30519	details
Glycerol-3-phosphate dehydrogenase, mitochondrial	GPD2	2q24.1	P43304	details
Heme oxygenase 1	HMOX1	22q13.1	P09601	details

Receptors

Not Available

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Heme oxygenase 1	HMOX1	22q13.1	P09601	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001197

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030853

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Flavin adenine dinucleotide

METLIN ID

6073

PubChem Compound

446013

PDB ID

Not Available

ChEBI ID

17877

References

General References

Not Available

Only showing the first 10 proteins. There are 18 proteins in total.

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Enzymes

Enzyme Details

1. Long-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADL
Uniprot ID:: P28330
Molecular weight:: 47655.275

Enzyme Details

2. Short-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADS
Uniprot ID:: P16219
Molecular weight:: 44296.705

Enzyme Details

3. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:: ACADM
Uniprot ID:: P11310
Molecular weight:: 46587.98

Enzyme Details

4. Peroxisomal acyl-coenzyme A oxidase 1

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:: ACOX1
Uniprot ID:: Q15067
Molecular weight:: 70135.205

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. Isovaleryl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: IVD
Uniprot ID:: P26440
Molecular weight:: 43055.325

Enzyme Details

7. Peroxisomal acyl-coenzyme A oxidase 3

General function:: Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:: Oxidizes the CoA-esters of 2-methyl-branched fatty acids (By similarity).
Gene Name:: ACOX3
Uniprot ID:: O15254
Molecular weight:: 69574.075

Enzyme Details

8. Glycerol-3-phosphate dehydrogenase, mitochondrial

General function:: Involved in calcium ion binding
Specific function:: Not Available
Gene Name:: GPD2
Uniprot ID:: P43304
Molecular weight:: 80851.99

Enzyme Details

9. 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

10. Glutaryl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the oxidative decarboxylation of glutaryl-CoA to crotonyl-CoA and CO(2) in the degradative pathway of L-lysine, L-hydroxylysine, and L-tryptophan metabolism. It uses electron transfer flavoprotein as its electron acceptor. Isoform Short is inactive.
Gene Name:: GCDH
Uniprot ID:: Q92947
Molecular weight:: 48126.715

Only showing the first 10 proteins. There are 18 proteins in total.

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Showing Compound Card for FADH (CDB005093)

Structure for CDB005093 (FADH)

Enzymes