retinoic acid

Term ID

CHEBI:26536

Synonyms

3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

Definition

A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).

References

LINCS:LSM-2135
PMID:24506204

Ontology

ChEBI ( EBI )

Relationships

is a type of: alpha,beta-unsaturated monocarboxylic acid retinoid

alpha,beta-unsaturated monocarboxylic acid retinoid Show first 5 Terms
has subtype: 9-cis-retinoic acid 11-cis-retinoic acid all-trans-retinoic acid isotretinoin

9-cis-retinoic acid 11-cis-retinoic acid all-trans-retinoic acid isotretinoin Show first 5 Terms
has_role: human metabolite

human metabolite Show first 5 Terms
inverse is_conjugate_base_of: retinoate

retinoate Show first 5 Terms
is_conjugate_acid_of: retinoate

retinoate Show first 5 Terms

Phenotype

Phenotype resulting from retinoic acid

Fish	Conditions	Phenotype	Term	Figures
AB	chemical treatment by environment: retinoic acid	hindbrain neural plate hnf1ba expression increased amount, abnormal	retinoic acid	Fig. 6 from Selland et al., 2018
AB/TU	chemical treatment by environment: retinoic acid	pectoral fin morphology, abnormal pectoral fin development disrupted, abnormal	retinoic acid	Fig. S6 from He et al., 2011
TU	chemical treatment by environment: retinoic acid	pronephros posterior region tbx2b expression decreased distribution, abnormal pronephros posterior region tbx2a expression decreased distribution, abnormal	retinoic acid	Fig. 8 from Drummond et al., 2017
TU	chemical treatment by environment: retinoic acid	whole organism fgg expression increased amount, abnormal whole organism fga expression increased amount, abnormal whole organism fgb expression increased amount, abnormal	retinoic acid	2 figures from Vilar et al., 2020
WT	chemical treatment by environment: retinoic acid	diencephalon prune2 expression increased amount, abnormal whole organism prune2 expression increased amount, abnormal hindbrain prune2 expression increased amount, abnormal cerebellum prune2 expression increased amount, abnormal	retinoic acid	Fig. 7 from Anuppalle et al., 2017
WT	chemical treatment by environment: retinoic acid	osteoclast increased amount, abnormal	retinoic acid	Fig. 6 from Liu et al., 2020
WT	chemical treatment: retinoic acid	heart contraction increased process quality, abnormal heart contraction process quality, abnormal	retinoic acid	Fig. 7 from Dash et al., 2017
WT	chemical treatment by environment: retinoic acid	epibranchial field sox3 expression decreased amount, abnormal central nervous system fgf8a expression increased distribution, abnormal ectoderm sox3 expression increased amount, abnormal central nervous system sox3 expression increased amount, abnormal ectoderm sox3 expression increased distribution, abnormal central nervous system sox3 expression increased distribution, abnormal central nervous system fgf8a expression increased amount, abnormal central nervous system fgf3 expression increased distribution, abnormal central nervous system fgf3 expression increased amount, abnormal presumptive rhombomere 3 displaced, abnormal hindbrain morphology, abnormal	retinoic acid	2 figures from Sun et al., 2007
WT	chemical treatment by environment: retinoic acid	pronephric distal late tubule slc12a3 expression decreased distribution, abnormal corpuscles of Stannius stc1 expression decreased distribution, abnormal pronephric distal early tubule slc12a1 expression mislocalised, abnormal corpuscles of Stannius stc1 expression decreased amount, abnormal pronephros multi-ciliated epithelial cell cimap1b expression mislocalised, abnormal corpuscles of Stannius stc1 expression mislocalised, abnormal pronephric distal late tubule slc12a3 expression mislocalised, abnormal pronephros multi-ciliated epithelial cell cimap1b expression increased distribution, abnormal	retinoic acid	2 figures from Barrodia et al., 2018
WT	chemical treatment by environment: retinoic acid	optomotor response process efficacy, normal eye normal size, normal	retinoic acid	FIGURE 10 from Hsiao et al., 2021

1 - 10 of 13

Show

Phenotype where environments contain retinoic acid

Phenotype modified by environments containing retinoic acid

Fish	Modification	Conditions	Phenotype	Term	Figures
AB	ameliorated	chemical treatment: ethanol, chemical treatment: retinoic acid	retina pax6a expression amount, ameliorated	ethanol retinoic acid	Fig. 4 from Zhang et al., 2015
AB + MO1-aldh1a3	ameliorated	chemical treatment by environment: ethanol, chemical treatment by environment: retinoic acid	swimming behavior process quality, abnormal eye size, ameliorated	ethanol retinoic acid	2 figures from Burton et al., 2017
AB + MO1-aldh1a3	ameliorated	chemical treatment by environment: retinoic acid	midbrain hindbrain boundary malformed, ameliorated	retinoic acid	Fig. 2 from Burton et al., 2017
AB + MO1-aldh1a3	ameliorated	chemical treatment: ethanol, chemical treatment: retinoic acid	eye size, ameliorated midbrain hindbrain boundary present, ameliorated	ethanol retinoic acid	2 figures from Zhang et al., 2015
AB + MO1-aldh1a3 + MO1-shha	ameliorated	chemical treatment: retinoic acid	midbrain hindbrain boundary present, ameliorated	retinoic acid	Fig. 1 from Zhang et al., 2015
AB + MO1-shha	ameliorated	chemical treatment: ethanol, chemical treatment: retinoic acid	midbrain hindbrain boundary present, ameliorated eye decreased size, abnormal	ethanol retinoic acid	2 figures from Zhang et al., 2015
b1212Tg (AB/TL)	exacerbated	chemical ablation: osteoblast, chemical treatment by environment: nifurpirinol, chemical treatment by environment: retinoic acid	opercle decreased length, exacerbated osteoblast EGFP expression absent, abnormal osteoblast regeneration arrested, abnormal opercle regeneration arrested, abnormal	nifurpirinol retinoic acid	Fig. 4 from McDonald et al., 2021
cdx4^{tv205c/tv205c} + MO2-cdx1a (TU)	ameliorated	chemical treatment by environment: 3-allyl-2-[2-(diethylamino)ethoxy]benzaldehyde, chemical treatment by environment: retinoic acid	lateral mesoderm myl7 expression amount, ameliorated	3-allyl-2-[2-(diethylamino)ethoxy]benzaldehyde retinoic acid	Fig. 7 from Lengerke et al., 2011
cdx4^{tv205c/tv205c} (TU)	ameliorated	chemical treatment by environment: 3-allyl-2-[2-(diethylamino)ethoxy]benzaldehyde, chemical treatment by environment: retinoic acid	lateral mesoderm myl7 expression amount, ameliorated	3-allyl-2-[2-(diethylamino)ethoxy]benzaldehyde retinoic acid	Fig. 7 from Lengerke et al., 2011
cku1Tg	ameliorated	heat shock, chemical treatment by environment: retinoic acid	optomotor response process efficacy, ameliorated eye normal size, ameliorated retinal rod cell rho expression amount, ameliorated	retinoic acid	FIGURE 10 from Hsiao et al., 2021

1 - 10 of 20

Show

Human Disease Model