Cannabis Compound Database: Showing Compound Card for Apigenin (CDB000370)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 27 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:33:25 UTC

Updated at

2022-12-13 19:31:28 UTC

CannabisDB ID

CDB000370

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Apigenin

Description

Apigenin, also known as chamomile or versulin, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Apigenin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It exists as a yellow crystalline solid that has been used to dye wool. Apigenin is abundantly found in fruits and vegetables including parsley, celery and chamomile tea. Apigenin is also one of 23 flavonoids that are found in cannabis plants (PMID: 6991645 ). It exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. Apigenin has shown significant promise as a skin cancer chemopreventive agent. In particular, apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311 (PMID: 16982614 ). Apigenin provides selective activity to promote caspase-dependent-apoptosis of leukemia cells (PMID: 16844095 ). Apigenin induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells (PMID: 16648565 ). Apigenin is biosynthetically derived from the general phenylpropanoid pathway. The phenylpropanoid pathway starts from the aromatic amino acids L-phenylalanine or L-tyrosine, both products of the Shikimate pathway. L-phenylalanine is deaminated by phenylalanine ammonia lyase (PAL) to make cinnamate, followed by oxidation at the para position by cinnamate 4-hydroxylase (C4H) to produce p-coumarate. 4-coumarate CoA ligase (4CL) then substitutes coenzyme A (CoA) at the carboxy group of p-coumarate. Later chalcone synthase (CHS) uses consecutive condensations of three equivalents of malonyl CoA followed by aromatization to convert p-coumaroyl-CoA to chalcone. Chalcone isomerase (CHI) then isomerizes the product to close the pyrone ring to make naringenin. Finally, a flavanone synthase (FNS) enzyme oxidizes naringenin to apigenin (PMID: 12636085 , 11524111 )

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-(p-Hydroxyphenyl)-5,7-dihydroxychromone	ChEBI
4',5,7-Trihydroxyflavone	ChEBI
5,7,4'-Trihydroxyflavone	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
C.I. natural yellow 1	ChEBI
Chamomile	ChEBI
Spigenin	ChEBI
Versulin	ChEBI
4',5,7-Trihydroxy-flavone	HMDB
4,5, 7-Trihydroxyflavone	HMDB
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one	HMDB
Apigenol	HMDB
4’,5,7-Trihydroxyflavone	PhytoBank
5,7,4’-Trihydroxyflavone	PhytoBank
5,7-Dihydroxy-2-(4-Hydroxyphenyl)chromen-4-one	PhytoBank
5,7-Dihydroxy-2-p-hydroxyphenyl-4-chromenone	PhytoBank
Apegenin	PhytoBank
Apigenin	PhytoBank
Apigenine	PhytoBank

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.24

Monoisotopic Molecular Weight

270.0528

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

chamomile

CAS Registry Number

461015-54-3

SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H

InChI Key

KZNIFHPLKGYRTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:18388 )
flavones (C01477 )
Flavones and Flavonols (C01477 )
Flavones and Flavonols (LMPK12110005 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Antineoplastic agent:

Antineoplastic

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	347.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	3.02	PERRISSOUD,D & TESTA,B (1986)

Predicted Properties

Property	Value	Source
logP	3.07	ALOGPS
logP	2.71	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.91 m³·mol⁻¹	ChemAxon
Polarizability	26.78 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Apigenin, 3 TMS, GC-MS Spectrum	splash10-00di-0000900000-b6d7fc88c039e719d164	Spectrum
GC-MS	Apigenin, non-derivatized, GC-MS Spectrum	splash10-00di-0433900000-b411d851fccc9f228d84	Spectrum
GC-MS	Apigenin, non-derivatized, GC-MS Spectrum	splash10-03xv-1913500000-be46740b1210f9e106ee	Spectrum
GC-MS	Apigenin, non-derivatized, GC-MS Spectrum	splash10-00di-0000900000-b6d7fc88c039e719d164	Spectrum
Predicted GC-MS	Apigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fu-0390000000-746c7fa7b11e53e27235	Spectrum
Predicted GC-MS	Apigenin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0229-4222900000-fe657c625506c272a036	Spectrum
Predicted GC-MS	Apigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0940000000-eb8b08c7beca627dc728	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-3fea3046af52ea21ae28	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0940000000-eb8b08c7beca627dc728	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-3fea3046af52ea21ae28	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-014i-0890000000-c8366acac0c0d42ae2e8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-0f608530bf761944dbf3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-0c659ac43b543480168b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0690000000-e19eed49b8311d9cd339	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0910000000-57a56bfe2cce55357a11	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-b8799a618cff0ac84ddb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0490000000-f9a416c79166c84ca773	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-1499c7f2bceeb3e13f52	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0490000000-413a7da79773bc92a112	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-8f4d30104539ae85cd50	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0290000000-32e8793c17b364eee127	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0uea-0900000000-52147353f7af35162dab	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0090000000-7a9b77ceb393c9239412	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00vi-0290000000-c9cb9331a28763da83a8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0940000000-eb8b08c7beca627dc728	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-014i-0900000000-072fb056044b71de2967	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0900000000-35e54babc71b9d557d7b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-d0d7979a02697bd4d8fd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0290000000-832bf870255aa3b01617	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0uea-0900000000-52147353f7af35162dab	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00am-0960000000-155c48a2761e351e02e3	2021-09-20	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 2 member 10	TAS2R10	12p13	Q9NYW0	details
Taste receptor type 2 member 16	TAS2R16	7q31.1-q31.3\|7q31	Q9NYV7	details
Taste receptor type 2 member 40	TAS2R40	7q34	P59535	details
Taste receptor type 2 member 3	TAS2R3	7q31.3-q32	Q9NYW6	details
Taste receptor type 2 member 4	TAS2R4	7q31.3-q32	Q9NYW5	details
Taste receptor type 2 member 7	TAS2R7	12p13	Q9NYW3	details
Taste receptor type 2 member 9	TAS2R9	12p13	Q9NYW1	details
Tumor necrosis factor receptor superfamily member 10B	TNFRSF10B	8p21.3	O14763	details
Taste receptor type 2 member 50	TAS2R50	12p13.2	P59544	details
Taste receptor type 2 member 38	TAS2R38	7q34	P59533	details
Taste receptor type 2 member 31	TAS2R31	12p13.2	P59538	details
Taste receptor type 2 member 1	TAS2R1	5p15.31	Q9NYW7	details
Taste receptor type 2 member 20	TAS2R20	12p13.2	P59543	details
Taste receptor type 2 member 39	TAS2R39	7q34	P59534	details
Taste receptor type 2 member 19	TAS2R19	12p13.2	P59542	details
Taste receptor type 2 member 45	TAS2R45		P59539	details
Taste receptor type 2 member 30	TAS2R30	12p13.2	P59541	details
Taste receptor type 2 member 42	TAS2R42		Q7RTR8	details
Taste receptor type 2 member 41	TAS2R41	7q35	P59536	details
Taste receptor type 2 member 43	TAS2R43	12p13.2	P59537	details
Taste receptor type 2 member 5	TAS2R5	7q34	Q9NYW4	details
Taste receptor type 2 member 46	TAS2R46	12p13.2	P59540	details
Taste receptor type 2 member 13	TAS2R13	12p13.2	Q9NYV9	details
Taste receptor type 2 member 60	TAS2R60	7q35	P59551	details
Taste receptor type 2 member 8	TAS2R8	12p13.2	Q9NYW2	details
Taste receptor type 2 member 14	TAS2R14	12p13.2	Q9NYV8	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.000677 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.000823 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.000422 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.00061 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0027 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.000418 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0002124

DrugBank ID

DB07352

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Apigenin

METLIN ID

3397

PubChem Compound

5280443

PDB ID

Not Available

ChEBI ID

18388

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Balasubramanian S, Zhu L, Eckert RL: Apigenin inhibition of involucrin gene expression is associated with a specific reduction in phosphorylation of protein kinase Cdelta Tyr311. J Biol Chem. 2006 Nov 24;281(47):36162-72. doi: 10.1074/jbc.M605368200. Epub 2006 Sep 18. [PubMed:16982614 ]
Vargo MA, Voss OH, Poustka F, Cardounel AJ, Grotewold E, Doseff AI: Apigenin-induced-apoptosis is mediated by the activation of PKCdelta and caspases in leukemia cells. Biochem Pharmacol. 2006 Sep 14;72(6):681-92. doi: 10.1016/j.bcp.2006.06.010. Epub 2006 Jul 17. [PubMed:16844095 ]
Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Sakai T: The dietary flavonoid apigenin sensitizes malignant tumor cells to tumor necrosis factor-related apoptosis-inducing ligand. Mol Cancer Ther. 2006 Apr;5(4):945-51. doi: 10.1158/1535-7163.MCT-05-0431. [PubMed:16648565 ]
Austin MB, Noel JP: The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep. 2003 Feb;20(1):79-110. doi: 10.1039/b100917f. [PubMed:12636085 ]
Martens S, Forkmann G, Matern U, Lukacin R: Cloning of parsley flavone synthase I. Phytochemistry. 2001 Sep;58(1):43-6. doi: 10.1016/s0031-9422(01)00191-1. [PubMed:11524111 ]

Only showing the first 10 proteins. There are 27 proteins in total.

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Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Only showing the first 10 proteins. There are 27 proteins in total.

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Showing Compound Card for Apigenin (CDB000370)

Structure for CDB000370 (Apigenin)

Enzymes