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Information on EC 1.14.11.9 - flavanone 3-dioxygenase
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EC Tree
1.14.11.9 flavanone 3-dioxygenaseIUBMB Comments
Requires Fe2+ and ascorbate. This plant enzyme catalyses an early step in the flavonoid biosynthesis pathway, leading to the production of flavanols and anthocyanins. Substrates include (2S)-naringenin, (2S)-eriodictyol, (2S)-dihydrotricetin and (2S)-pinocembrin. Some enzymes are bifuctional and also catalyse EC 1.14.20.6, flavonol synthase.
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Word Map
- 1.14.11.9
- chalcone
- anthocyanins
- dihydroflavonols
- flavonols
- anthocyanidin
-
4-reductase
-
ammonia-lyase
-
3\'-hydroxylase
- petunia
- proanthocyanidins
- dihydrokaempferol
-
leucoanthocyanidin
- 3-o-glucosyltransferase
-
2-oxoglutarate-dependent
-
3',5'-hydroxylase
-
r2r3-myb
- eriodictyol
- analysis
-
testa
-
udp-glucose:flavonoid
-
2s-flavanones
-
4-coumarate-coa
- dihydroflavonol-4-reductase
- dihydroquercetin
- 2s-naringenin
- pelargonidin
- synthesis
- agriculture
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
Synonyms
flavanone 3-hydroxylase, flavanone-3-hydroxylase, flavanone 3beta-hydroxylase, csf3h, lcf3h, aaf3h, ctf3h, naringenin 3-dioxygenase, acf3h, (2s)-flavanone 3-hydroxylase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(2S)-flavanone 3-hydroxylase
-
-
-
-
AcF3H
CsF3H
F3H
FHT
FHTPH
-
-
-
-
flavanone 3-dioxygenase
flavanone 3-hydroxylase
flavanone 3beta-hydroxylase
flavanone synthase I
-
-
-
-
flavanone-3-hydroxylase
FS I
-
-
-
-
naringenin 3-dioxygenase
-
-
-
-
naringenin,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
-
-
-
-
oxygenase, flavanone 3-di-
-
-
-
-
F3H
-
-
-
-
flavanone 3-hydroxylase
-
-
-
-
flavanone 3beta-hydroxylase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a (2S)-flavan-4-one + 2-oxoglutarate + O2 = a (2R,3R)-dihydroflavonol + succinate + CO2
enzyme catalyzes double-bond formation by direct abstraction of vicinal hydrogen atoms at C-2 and C-3 of the substrate
-
a (2S)-flavan-4-one + 2-oxoglutarate + O2 = a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(2S)-flavan-4-one,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
Requires Fe2+ and ascorbate. This plant enzyme catalyses an early step in the flavonoid biosynthesis pathway, leading to the production of flavanols and anthocyanins. Substrates include (2S)-naringenin, (2S)-eriodictyol, (2S)-dihydrotricetin and (2S)-pinocembrin. Some enzymes are bifuctional and also catalyse EC 1.14.20.6, flavonol synthase.
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CAS REGISTRY NUMBER
COMMENTARY
75991-43-4
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2S)-flavanone + 2-oxoglutarate + O2
(2R/3R)-dihydroflavonol + succinate + CO2
-
key step towards biosynthesis of flavonols, anthocyanins and catechins
-
-
?
(S)-eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
-
-
?
(S)-eriodictyol + 2-oxoglutarate + O2
dihydroquercetin + succinate + CO2
-
-
-
?
(S)-homoeriodictyol + 2-oxoglutarate + O2
3'-O-methyltaxifolin + succinate + CO2
-
-
-
?
(S)-pinocembrin + 2-oxoglutarate + O2
pinobanksin + succinate + CO2
-
-
-
?
eriodyctiol + 2-oxoglutarate + O2
dihydroquercetin + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoadipate + O2
dihydrokaempferol + pentanedioate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + O2 + 2 H2O
-
-
-
-
?
pinocembrin + 2-oxoglutarate + O2
?
-
38% of the activity with naringenin
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
enzyme is stereospecific for (S)-naringenin
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
reaction is stereospecific
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
90% of the activity with eriodictyol
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
F3H
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
F3H
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
ir
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
His220, His278 and Asp222 are part of the 2-oxoglutarate binding site
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
3'-methoxy eriodictyol + 2-oxoglutarate + O2
? + succinate + CO2
-
16% of the activity with eriodictyol
-
-
?
3'-methoxy eriodictyol + 2-oxoglutarate + O2
? + succinate + CO2
-
-
-
?
3'-methoxy eriodictyol + 2-oxoglutarate + O2
? + succinate + CO2
68% of the activity with eriodictyol
-
-
?
4'-methoxy eriodictyol + 2-oxoglutarate + O2
? + succinate + CO2
-
56% of the activity with eriodictyol
-
-
?
4'-methoxy eriodictyol + 2-oxoglutarate + O2
? + succinate + CO2
-
-
-
?
4'-methoxy eriodictyol + 2-oxoglutarate + O2
? + succinate + CO2
105% of the activity with eriodictyol
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
Camellia sinensis UPASI-10
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
the 2-oxoglutarate binding site RxS is formed by Arg289 and Ser291
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
-
-
-
?
a (2S)-flavan-4-one + 2-oxoglutarate + O2
a (2R,3R)-dihydroflavonol + succinate + CO2
x Ascocenda NK-2012
-
-
-
?
a flavanone + 2-oxoglutarate + O2
a dihydroflavonol + succinate + CO2
-
-
-
-
?
a flavanone + 2-oxoglutarate + O2
a dihydroflavonol + succinate + CO2
-
-
-
?
a flavanone + 2-oxoglutarate + O2
a dihydroflavonol + succinate + CO2
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
-
-
-
ir
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
(2S)-eriodictyol
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
95% of the activity with naringenin
-
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
(2R,3R)-dihydroquercetin + succinate + CO2
-
50% of the activity with naringenin
-
-
?
eriodictyol + 2-oxoglutarate + O2
dihydroquercetin + succinate + CO2
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
dihydroquercetin + succinate + CO2
Camellia sinensis UPASI-10
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
dihydroquercetin + succinate + CO2
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
dihydroquercetin + succinate + CO2
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
dihydroquercetin + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
the F3H gene is coordinately expressed with chalcone synthase and chalcone isomerase in seedlings. The F3H gene may represent a pivotal point in the regulation of flavonoid biosynthesis
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
enzyme is involved in anthocyanin pathway
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
ir
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
enzyme is involved in anthocyanin pathway
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
enzyme is involved in anthocyanin biosynthesis
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
enzyme is involved in anthocyanin pathway
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
enzyme is involved in the biosynthesis of flavonoids, catechins, and anthocyanidins
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
induction of the enzyme by light
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
enzyme is involved in anthocyanin pathway
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
Streptocarpus hybrida
-
enzyme is involved in anthocyanin pathway
-
-
?
naringenin + 2-oxoglutarate + O2
(2R,3R)-dihydrokaempferol + succinate + CO2
-
enzyme is involved in anthocyanin pathway
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
Camellia sinensis UPASI-10
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + 2-oxoglutarate + O2
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris-HCl, pH 7.5, containing 0.4% sodium ascorbate)
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris/HCl, pH 7.5, containing 0.4% sodium ascorbate)
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris/HCl, pH 7.5, containing 0.4% sodium ascorbate)
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris/HCl, pH 7.5, containing 0.4% sodium ascorbate)
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris/HCl, pH 7.5, containing 0.4% sodium ascorbate)
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
-
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris/HCl, pH 7.5, containing 0.4% sodium ascorbate)
-
-
?
naringenin + O2 + 2-oxoglutarate
dihydrokaempferol + succinate + CO2
-
0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris/HCl, pH 7.5, containing 0.4% sodium ascorbate)
-
-
?
additional information
?
-
involved in catechin biosynthesis
-
-
?
additional information
?
-
no activity with kaempferol, dihydrokaempferol, quercetin, and dihydroquercetin
-
-
?
additional information
?
-
-
no activity with kaempferol, dihydrokaempferol, quercetin, and dihydroquercetin
-
-
?
additional information
?
-
development of a reverse phase (C18) HPLC method (with elutant ethylacetate) for the determination of flavanone 3beta-hydroxylase and other enzyme activities based on the determination of the compounds produced and consumed on the enzymatic reaction in just one chromatographic analysis, method optimisation considering kinetic studies to establish the optimal assay incubation time
-
-
?
additional information
?
-
-
no activity with (+)-dihydrokaempferol and (2R)-naringenin
-
-
?
additional information
?
-
-
no activity with (2R)-naringenin and 5,7,3',4',5'-pentahydroxyflavanone
-
-
?
additional information
?
-
-
two different protocols for enzyme preparation from eight fruit species
-
-
?
additional information
?
-
-
two different protocols for enzyme preparation from eight fruit species
-
-
?
additional information
?
-
-
two different protocols for enzyme preparation from eight fruit species
-
-
?
additional information
?
-
-
development of a reverse phase (C18) HPLC method (with elutant ethylacetate) for the determination of flavanone 3beta-hydroxylase and other enzyme activities based on the determination of the compounds produced and consumed on the enzymatic reaction in just one chromatographic analysis, method optimisation considering kinetic studies to establish the optimal assay incubation time
-
-
?
additional information
?
-
development of a reverse phase (C18) HPLC method (with elutant ethylacetate) for the determination of flavanone 3beta-hydroxylase and other enzyme activities based on the determination of the compounds produced and consumed on the enzymatic reaction in just one chromatographic analysis, method optimisation considering kinetic studies to establish the optimal assay incubation time
-
-
?
additional information
?
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development of a reverse phase (C18) HPLC method (with elutant ethylacetate) for the determination of flavanone 3beta-hydroxylase and other enzyme activities based on the determination of the compounds produced and consumed on the enzymatic reaction in just one chromatographic analysis, method optimisation considering kinetic studies to establish the optimal assay incubation time
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additional information
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development of a reverse phase (C18) HPLC method (with elutant ethylacetate) for the determination of flavanone 3beta-hydroxylase and other enzyme activities based on the determination of the compounds produced and consumed on the enzymatic reaction in just one chromatographic analysis, method optimisation considering kinetic studies to establish the optimal assay incubation time
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?
additional information
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two different protocols for enzyme preparation from eight fruit species