superpathway of bitter acids biosynthesis

Goese M, Kammhuber K, Bacher A, Zenk MH, Eisenreich W. Biosynthesis of bitter acids in hops. A (13)C-NMR and (2)H-NMR study on the building blocks of humulone. Eur J Biochem. 1999 Jul;263(2):447–54. doi: 10.1046/j.1432-1327.1999.00518.x. PMID: 10406953.; Paniego NB, Zuurbier KWM, Fung S, van der Heijden R, Scheffer JJC, Verpoorte R. Phlorisovalerophenone synthase, a novel polyketide synthase from hop (Humulus lupulus L.) cones. European Journal of Biochemistry. 1999 Jun;262(2):612–6. doi: 10.1046/j.1432-1327.1999.00444.x.

Metabolites

CO2

Formula: CO2 (43.98983)

CAS ID: 124-38-9

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Humulone

Formula: C21H30O5 (362.209313)

CAS ID: 23510-81-8

Lupulone

Formula: C26H38O4 (414.2769948)

CAS ID: 468-28-0

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

Multifidol

Formula: C11H14O4 (210.0892044)

CAS ID: 125074-06-8

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Phlorisobutyrophenone

Formula: C10H12O4 (196.0735552)

CAS ID: 35458-21-0

Phlorisovalerophenone

Formula: C11H14O4 (210.0892044)

CAS ID: 26103-97-9

Colupulone

Formula: C25H36O4 (400.2613456)

CAS ID: 468-27-9

Adhumulone

Formula: C21H30O5 (362.209313)

CAS ID: 28374-89-2

Cohumulone

Formula: C20H28O5 (348.1936638)

CAS ID: 511-25-1

4-Deoxycohumulone

Formula: C20H28O4 (332.19874880000003)

CAS ID: 5880-42-2

4-Deoxyhumulone

Formula: C21H30O4 (346.214398)

CAS ID: 4374-93-0

isovalerate

Formula: C5H9O2 (101.0602514)

CAS ID:

isobutyrate

Formula: C4H7O2 (87.0446022)

CAS ID: 5711-69-3

ATP(4-)

Formula: C10H12N5O13P3 (502.9644492)

CAS ID:



Enzyme

EC Number name full name note
6.2.1.-
2.3.1.156 phloroisovalerophenone synthase isovaleryl-CoA:malonyl-CoA acyltransferase
2.3.1.74 chalcone synthase malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing)
2.5.1.136 2-acylphloroglucinol 4-prenyltransferase prenyl-diphosphate:2-acylphloroglucinol 4-prenyltransferase
2.5.1.137 2-acyl-4-prenylphloroglucinol 6-prenyltransferase dimethylallyl-diphosphate:2-acyl-4-prenylphloroglucinol 6-dimethylallyltransferase
6.2.1.17 propionate-CoA ligase propanoate:CoA ligase (AMP-forming)


Proteins

Protein ID name full name