Secondary metabolism

Perera I, Seneweera S, Hirotsu N. Manipulating the Phytic Acid Content of Rice Grain Toward Improving Micronutrient Bioavailability. Rice (N Y). 2018 Jan 11;11(1):4. PMID: 29327163; PMCID: PMC5764899.; Lam PY, Liu H, Lo C. Completion of Tricin Biosynthesis Pathway in Rice: Cytochrome P450 75B4 Is a Unique Chrysoeriol 5'-Hydroxylase. Plant Physiol. 2015 Aug;168(4):1527–36. PMID: 26082402; PMCID: PMC4528758.; Lam PY, Zhu FY, Chan WL, Liu H, Lo C. Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice. Plant Physiol. 2014 Jul;165(3):1315–27. PMID: 24843076; PMCID: PMC4081339.; Suzuki M, Tanaka K, Kuwano M, Yoshida KT. Expression pattern of inositol phosphate-related enzymes in rice (Oryza sativa L.): implications for the phytic acid biosynthetic pathway. Gene. 2007 Dec 15;405(1-2):55–64. doi: 10.1016/j.gene.2007.09.006. PMID: 17961936.; Shimura K, Okada A, Okada K, Jikumaru Y, Ko K, Toyomasu T, Sassa T, Hasegawa M, Kodama O, Shibuya N, Koga J, Nojiri H, Yamane H. Identification of a Biosynthetic Gene Cluster in Rice for Momilactones. Journal of Biological Chemistry. 2007 Nov;282(47):34013–8. doi: 10.1074/jbc.m703344200.

Metabolites

(-)-alpha-Pinene

Formula: C10H16 (136.1251936)

CAS ID: 7785-26-4

(-)-alpha-Terpineol

Formula: C10H18O (154.1357578)

CAS ID: 10482-56-1

(-)-beta-Phellandrene

Formula: C10H16 (136.1251936)

CAS ID: 6153-17-9

(-)-beta-Pinene

Formula: C10H16 (136.1251936)

CAS ID: 18172-67-3

(-)-Camphene

Formula: C10H16 (136.1251936)

CAS ID: 5794-04-7

(-)-Vestitone

Formula: C16H14O5 (286.0841194)

CAS ID: 158112-50-6

(+)-3-Carene

Formula: C10H16 (136.1251936)

CAS ID: 498-15-7

(+)-Catechin

Formula: C15H14O6 (290.0790344)

CAS ID: 154-23-4

(9Z)-Octadecenoic acid

Formula: C18H34O2 (282.2558664)

CAS ID: 112-80-1

(E)-beta-Ocimene

Formula: C10H16 (136.1251936)

CAS ID: 3779-61-1

(S)-2,3-Epoxysqualene

Formula: C30H50O (426.386145)

CAS ID: 54910-48-4

(S)-Limonene

Formula: C10H16 (136.1251936)

CAS ID: 5989-54-8

1,8-Cineole

Formula: C10H18O (154.1357578)

CAS ID: 470-82-6

13(S)-HPOT

Formula: C18H30O4 (310.214398)

CAS ID: 67597-26-6

1D-myo-Inositol 3-phosphate

Formula: C6H13O9P (260.0297178)

CAS ID: 2831-74-5

2'-Hydroxyformononetin

Formula: C16H12O5 (284.0684702)

CAS ID: 1890-99-9

24-Ethylidenelophenol

Formula: C30H50O (426.386145)

CAS ID: 474-40-8

24-Methylenecholesterol

Formula: C28H46O (398.3548466)

CAS ID: 474-63-5

24-Methylenelophenol

Formula: C29H48O (412.37049579999996)

CAS ID: 1176-52-9

3-alpha(S)-Strictosidine

Formula: C27H34N2O9 (530.2264194)

CAS ID: 20824-29-7

3-Hexenal

Formula: C6H10O (98.07316100000001)

CAS ID: 6789-80-6

3-Hexenol

Formula: C6H12O (100.0888102)

CAS ID: 928-96-1

4-Coumarate

Formula: C9H8O3 (164.0473418)

CAS ID: 7400-08-0

4-Coumaroylshikimate

Formula: C16H16O7 (320.0895986)

CAS ID: 196496-50-1

5-Epiaristolochene

Formula: C15H24 (204.18779039999998)

CAS ID: 115888-31-8

6-O-Methyl-myo-inositol

Formula: C7H14O6 (194.0790344)

CAS ID: 6090-97-7

Acetone

Formula: C3H6O (58.041862599999995)

CAS ID: 67-64-1

all-trans-Neurosporene

Formula: C40H58 (538.4538268)

CAS ID: 502-64-7

all-trans-Phytoene

Formula: C40H64 (544.5007744)

CAS ID: 540-04-5

all-trans-Phytofluene

Formula: C40H62 (542.4851252)

CAS ID: 27664-65-9

all-trans-zeta-Carotene

Formula: C40H60 (540.469476)

CAS ID: 13587-06-9

Ammonia

Formula: NH3 (17.0265478)

CAS ID: 7664-41-7

Antheraxanthin

Formula: C40H56O3 (584.4229226)

CAS ID: 640-03-9

Apigenin

Formula: C15H10O5 (270.052821)

CAS ID: 520-36-5

Aromatic acid

Formula: C7H6O2 (122.0367776)

CAS ID: 65-85-0

Bergapten

Formula: C12H8O4 (216.0422568)

CAS ID: 484-20-8

Bergaptol

Formula: C11H6O4 (202.0266076)

CAS ID: 486-60-2

beta-Carotene

Formula: C40H56 (536.4381776)

CAS ID: 7235-40-7

beta-Caryophyllene

Formula: C15H24 (204.18779039999998)

CAS ID: 87-44-5

beta-Cryptoxanthin

Formula: C40H56O (552.4330926)

CAS ID: 472-70-8

beta-Sitosterol

Formula: C29H50O (414.386145)

CAS ID: 83-46-5

Caffeoyl-CoA

Formula: C30H42N7O19P3S (929.1468972000001)

CAS ID: 53034-79-0

Calycosin

Formula: C16H12O5 (284.0684702)

CAS ID: 20575-57-9

Campesterol

Formula: C28H48O (400.37049579999996)

CAS ID: 474-62-4

Capsidiol

Formula: C15H24O2 (236.1776204)

CAS ID: 37208-05-2

Chorismate

Formula: C10H10O6 (226.04773600000001)

CAS ID: 617-12-9

Chrysoeriol

Formula: C16H12O6 (300.06338519999997)

CAS ID: 491-71-4

cis-3,4-Leucopelargonidin

Formula: C15H14O6 (290.0790344)

CAS ID: 98919-66-5

CO2

Formula: CO2 (43.98983)

CAS ID: 124-38-9

Coniferyl alcohol

Formula: C10H12O3 (180.0786402)

CAS ID: 32811-40-8

Coniferyl aldehyde

Formula: C10H10O3 (178.062991)

CAS ID: 458-36-6

Coumarin

Formula: C9H6O2 (146.0367776)

CAS ID: 91-64-5

Crocetin

Formula: C20H24O4 (328.1674504)

CAS ID: 27876-94-4

Crocetin dialdehyde

Formula: C20H24O2 (296.17762039999997)

CAS ID: 502-70-5

Cyanidin

Formula: C15H11O6 (287.05556060000004)

CAS ID: 528-58-5

Cycloartenol

Formula: C30H50O (426.386145)

CAS ID: 469-38-5

Cycloeucalenol

Formula: C30H50O (426.386145)

CAS ID: 469-39-6

D-Glucose

Formula: C6H12O6 (180.0633852)

CAS ID: 50-99-7

D-Glucose 6-phosphate

Formula: C6H13O9P (260.0297178)

CAS ID: 56-73-5

Daidzein

Formula: C15H10O4 (254.057906)

CAS ID: 486-66-8

Delphinidin

Formula: C15H11O7 (303.0504756)

CAS ID: 528-53-0

Deoxyloganin

Formula: C17H26O9 (374.1576746)

CAS ID: 26660-57-1

Dihydrokaempferol

Formula: C15H12O6 (288.06338519999997)

CAS ID: 480-20-6

Dihydrophaseic acid

Formula: C15H22O5 (282.1467162)

CAS ID: 41756-77-8

Dimethylallyl diphosphate

Formula: C5H12O7P2 (246.0058262)

CAS ID: 358-72-5

ent-Copalyl diphosphate

Formula: C20H36O7P2 (450.1936166)

CAS ID: 21738-30-7

ent-Kaurene

Formula: C20H32 (272.2503872)

CAS ID: 562-28-7

Eriodictyol

Formula: C15H12O6 (288.06338519999997)

CAS ID: 552-58-9

Ferulate

Formula: C10H10O4 (194.057906)

CAS ID: 537-98-4

Feruloyl-CoA

Formula: C31H44N7O19P3S (943.1625464)

CAS ID: 142185-30-6

Formononetin

Formula: C16H12O4 (268.0735552)

CAS ID: 485-72-3

gamma-Carotene

Formula: C40H56 (536.4381776)

CAS ID: 472-93-5

Genistein

Formula: C15H10O5 (270.052821)

CAS ID: 446-72-0

Geraniol

Formula: C10H18O (154.1357578)

CAS ID: 106-24-1

Geranyl diphosphate

Formula: C10H20O7P2 (314.068423)

CAS ID: 763-10-0

Geranylgeranyl diphosphate

Formula: C20H36O7P2 (450.1936166)

CAS ID: 6699-20-3

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Hydrogen

Formula: H2 (2.0156492)

CAS ID: 1333-74-0

Hygrine

Formula: C8H15NO (141.115358)

CAS ID: 496-49-1

Isochorismate

Formula: C10H10O6 (226.04773600000001)

CAS ID: 22642-82-6

Isofucosterol

Formula: C29H48O (412.37049579999996)

CAS ID: 481-14-1

Isoliquiritigenin

Formula: C15H12O4 (256.0735552)

CAS ID: 961-29-5

Kievitone hydrate

Formula: C20H22O7 (374.1365462)

CAS ID: 62682-11-5

Lactucaxanthin

Formula: C40H56O2 (568.4280076)

CAS ID: 78306-12-4

Linoleate

Formula: C18H32O2 (280.2402172)

CAS ID: 60-33-3

Liquiritigenin

Formula: C15H12O4 (256.0735552)

CAS ID: 578-86-9

Loganin

Formula: C17H26O10 (390.1525896)

CAS ID: 18524-94-2

Longifolene

Formula: C15H24 (204.18779039999998)

CAS ID: 475-20-7

Lutein

Formula: C40H56O2 (568.4280076)

CAS ID: 127-40-2

Luteolin

Formula: C15H10O6 (286.047736)

CAS ID: 491-70-3

Luteone

Formula: C20H18O6 (354.1103328)

CAS ID: 41743-56-0

Lycopene

Formula: C40H56 (536.4381776)

CAS ID: 502-65-8

Marmesin

Formula: C14H14O4 (246.0892044)

CAS ID: 13849-08-6

Medicarpin

Formula: C16H14O4 (270.0892044)

CAS ID: 32383-76-9

Momilactone A

Formula: C20H26O3 (314.1881846)

CAS ID: 51415-07-7

myo-Inositol

Formula: C6H12O6 (180.0633852)

CAS ID: 87-89-8

Myrcene

Formula: C10H16 (136.1251936)

CAS ID: 123-35-3

N-Feruloyltyramine

Formula: C18H19NO4 (313.1314014)

CAS ID: 66648-43-9

NADP+

Formula: C21H29N7O17P3 (744.0832754)

CAS ID: 53-59-8

NADPH

Formula: C21H30N7O17P3 (745.0911)

CAS ID: 2646-71-1

Naringenin

Formula: C15H12O5 (272.0684702)

CAS ID: 480-41-1

Neoxanthin

Formula: C40H56O4 (600.4178376)

CAS ID: 30743-41-0

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

p-Coumaroyl-CoA

Formula: C30H42N7O18P3S (913.1519822000001)

CAS ID: 119785-99-8

Phaseic acid

Formula: C15H20O5 (280.13106700000003)

CAS ID: 24394-14-7

Picrocrocin

Formula: C16H26O7 (330.16784459999997)

CAS ID: 138-55-6

Presqualene diphosphate

Formula: C30H52O7P2 (586.3188102)

CAS ID: 29849-75-0

Pseudotropine

Formula: C8H15NO (141.115358)

CAS ID: 135-97-7

Psoralen

Formula: C11H6O3 (186.0316926)

CAS ID: 66-97-7

Quinate

Formula: C7H12O6 (192.0633852)

CAS ID: 77-95-2

Resveratrol

Formula: C14H12O3 (228.0786402)

CAS ID: 501-36-0

Sabinene

Formula: C10H16 (136.1251936)

CAS ID: 3387-41-5

Secologanin

Formula: C17H24O10 (388.13694039999996)

CAS ID: 19351-63-4

Shikimate

Formula: C7H10O5 (174.052821)

CAS ID: 138-59-0

Sinapoyl aldehyde

Formula: C11H12O4 (208.0735552)

CAS ID: 4206-58-0

Squalene

Formula: C30H50 (410.39123)

CAS ID: 111-02-4

Stemar-13-ene

Formula: C20H32 (272.2503872)

CAS ID: 138883-56-4

Stigmasterol

Formula: C29H48O (412.37049579999996)

CAS ID: 83-48-7

Sulcatone

Formula: C8H14O (126.10445940000001)

CAS ID: 110-93-0

Taxifolin

Formula: C15H12O7 (304.05830019999996)

CAS ID: 480-18-2

Terpinolene

Formula: C10H16 (136.1251936)

CAS ID: 586-62-9

trans-2-Hydroxycinnamate

Formula: C9H8O3 (164.0473418)

CAS ID: 614-60-8

trans-Cinnamate

Formula: C9H8O2 (148.0524268)

CAS ID: 140-10-3

Traumatin

Formula: C12H20O3 (212.14123700000002)

CAS ID: 65410-38-0

Tricin

Formula: C17H14O7 (330.0739494)

CAS ID: 520-32-1

Tropinone

Formula: C8H13NO (139.0997088)

CAS ID: 532-24-1

Tryptamine

Formula: C10H12N2 (160.1000432)

CAS ID: 61-54-1

Tyramine

Formula: C8H11NO (137.0840596)

CAS ID: 51-67-2

Umbelliferone

Formula: C9H6O3 (162.03169259999999)

CAS ID: 93-35-6

Violaxanthin

Formula: C40H56O4 (600.4178376)

CAS ID: 126-29-4

Zeaxanthin

Formula: C40H56O2 (568.4280076)

CAS ID: 144-68-3

cis-Ocimene

Formula: C10H16 (136.1251936)

CAS ID: 3338-55-4

Pseudoionone

Formula: C13H20O (192.151407)

CAS ID: 3548-78-5

Dihydrobrassicasterol

Formula: C28H48O (400.37049579999996)

CAS ID: 4651-51-8

Salicylates

Formula: C7H5O3 (137.023868)

CAS ID: 63-36-5

D-Selinene

Formula: C15H24 (204.18779039999998)

CAS ID: 473-14-3

Leucocyanidin

Formula: C15H14O7 (306.0739494)

CAS ID:

formate

Formula: CHO2 (44.997654600000004)

CAS ID: 71-47-6

Bixindial

Formula: C24H28O2 (348.2089188)

CAS ID:

pelargonidin chloride

Formula: C15H11ClO5 (306.0294986)

CAS ID: 134-04-3

2-oxoglutarate(2-)

Formula: C5H4O5 (144.00587339999998)

CAS ID: 64-15-3

succinate(2-)

Formula: C4H4O4 (116.01095839999999)

CAS ID: 56-14-4

pyruvate

Formula: C3H3O3 (87.00821880000001)

CAS ID: 57-60-3

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

ATP(4-)

Formula: C10H12N5O13P3 (502.9644492)

CAS ID:

UDP(3-)

Formula: C9H11N2O12P2 (400.9787246)

CAS ID: 86527-70-0

ADP(3-)

Formula: C10H12N5O10P2 (424.0059412)

CAS ID:

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
1.14.-.-
1.1.1.195 cinnamyl-alcohol dehydrogenase cinnamyl-alcohol:NADP+ oxidoreductase
1.1.1.295 momilactone-A synthase 3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide:NAD(P)+ oxidoreductase
1.14.11.9 flavanone 3-dioxygenase (2S)-flavan-4-one,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
1.14.14.76 ent-isokaurene C2/C3-hydroxylase ent-isokaurene,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (ent-isokaurene-2beta,3beta-diol forming)
1.14.14.82 flavonoid 3'-monooxygenase flavonoid,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
1.14.15.21 zeaxanthin epoxidase zeaxanthin,reduced ferredoxin:oxygen oxidoreductase
1.14.19.76 flavone synthase II flavanone,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (flavone-forming)
1.3.1.83 geranylgeranyl diphosphate reductase geranylgeranyl-diphosphate:NADP+ oxidoreductase
2.1.1.143 24-methylenesterol C-methyltransferase S-adenosyl-L-methionine:24-methylenelophenol C-methyltransferase
2.1.1.4 acetylserotonin O-methyltransferase S-adenosyl-L-methionine:N-acetylserotonin O-methyltransferase
2.1.1.41 sterol 24-C-methyltransferase S-adenosyl-L-methionine:zymosterol 24-C-methyltransferase
2.1.1.42 flavone 3'-O-methyltransferase S-adenosyl-L-methionine:3'-hydroxyflavone 3'-O-methyltransferase
2.1.1.68 caffeate O-methyltransferase S-adenosyl-L-methionine:3,4-dihydroxy-trans-cinnamate 3-O-methyltransferase
2.3.1.74 chalcone synthase malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing)
2.5.1.32 15-cis-phytoene synthase geranylgeranyl-diphosphate:geranylgeranyl-diphosphate geranylgeranyltransferase (15-cis-phytoene forming)
2.7.1.140 inositol-tetrakisphosphate 5-kinase ATP:1D-myo-inositol-1,3,4,6-tetrakisphosphate 5-phosphotransferase
2.7.1.151 inositol-polyphosphate multikinase ATP:1D-myo-inositol-1,4,5-trisphosphate 6-phosphotransferase
3.2.1.21 beta-glucosidase beta-D-glucoside glucohydrolase
4.2.3.103 ent-isokaurene synthase ent-copalyl-diphosphate diphosphate-lyase (cyclizing, ent-isokaurene-forming)
4.2.3.28 ent-cassa-12,15-diene synthase ent-copalyl-diphosphate diphosphate-lyase (ent-cassa-12,15-diene-forming)
4.2.3.29 ent-sandaracopimaradiene synthase ent-copalyl-diphosphate diphosphate-lyase [ent-sandaracopimara-8(14),15-diene-forming]
4.2.3.33 stemar-13-ene synthase 9alpha-copalyl-diphosphate diphosphate-lyase (stemar-13-ene-forming)
4.2.3.35 syn-pimara-7,15-diene synthase 9alpha-copalyl-diphosphate diphosphate-lyase (9beta-pimara-7,15-diene-forming)
4.2.3.99 labdatriene synthase 9alpha-copalyl-diphosphate diphosphate-lyase [(12E)-9alpha-labda-8(17),12,14-triene-forming]
5.3.3.5 cholestenol DELTA-isomerase DELTA7-Cholestenol DELTA7-DELTA8-isomerase
5.4.2.3 phosphoacetylglucosamine mutase N-Acetyl-alpha-D-glucosamine 1,6-phosphomutase
5.5.1.14 syn-copalyl-diphosphate synthase 9alpha-copalyl-diphosphate lyase (decyclizing)
5.5.1.4 inositol-3-phosphate synthase 1D-myo-inositol-3-phosphate lyase (isomerizing)
5.5.1.6 chalcone isomerase flavanone lyase (decyclizing)


Proteins

Protein ID name full name