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Record Information
Version2.0
Created at2006-02-16 11:10:57 UTC
Updated at2024-09-17 15:43:06 UTC
NP-MRD IDNP0000829
Secondary Accession NumbersNone
Natural Product Identification
Common Nameall-trans-Retinoic acid
DescriptionAll-trans-Retinoic acid is an isomer of retinoic acid, the oxidized form of vitamin A. Retinoic acid functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912 ). It is an important regulator of gene expression during growth and development, and in neoplasms. As a drug, all-trans-retinoic acid is known as tretinoin. Tretinoin is derived from maternal vitamin A and is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. Tretinoin is used in the treatment of psoriasis, acne vulgaris, and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).
Structure
Thumb
Synonyms
ValueSource
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acidChEBI
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acidChEBI
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acidChEBI
3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic acidChEBI
3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoic acidChEBI
AGN 100335ChEBI
all-(e)-Retinoic acidChEBI
all-trans Retinoic acidChEBI
all-trans-beta-Retinoic acidChEBI
all-trans-TretinoinChEBI
all-trans-Vitamin a acidChEBI
all-trans-Vitamin a1 acidChEBI
AltrenoChEBI
AtralinChEBI
AvitaChEBI
beta-Retinoic acidChEBI
BetarretinChEBI
BiacnaChEBI
Cordes vasChEBI
DermairolChEBI
RefissaChEBI
RenovaChEBI
Retin-aChEBI
Retinoic acidChEBI
Retisol-aChEBI
Ro 1-5488ChEBI
Stieva-aChEBI
trans-Retinoic acidChEBI
Tretin mChEBI
TretinoinChEBI
TretinoinaChEBI
TretinoineChEBI
TretinoinumChEBI
Tri-lumaChEBI
VeltinChEBI
VesanoidChEBI
Vitamin a acidChEBI
VitinoinChEBI
all-trans-RetinoateKegg
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)Kegg
Retin aKegg
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoateGenerator
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoateGenerator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoateGenerator
3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoateGenerator
3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoateGenerator
all-(e)-RetinoateGenerator
all-trans RetinoateGenerator
all-trans-b-RetinoateGenerator
all-trans-b-Retinoic acidGenerator
all-trans-beta-RetinoateGenerator
all-trans-Β-retinoateGenerator
all-trans-Β-retinoic acidGenerator
b-RetinoateGenerator
b-Retinoic acidGenerator
beta-RetinoateGenerator
Β-retinoateGenerator
Β-retinoic acidGenerator
RetinoateGenerator
trans-RetinoateGenerator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)Generator
EudynaHMDB
SolageHMDB
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoateHMDB
Tretinoin zinc saltHMDB
trans Retinoic acidHMDB
Acid, all-trans-retinoicHMDB
Salt, tretinoin sodiumHMDB
beta all trans Retinoic acidHMDB
beta-all-trans-Retinoic acidHMDB
Acid, vitamin aHMDB
Potassium salt, tretinoinHMDB
Sodium salt, tretinoinHMDB
Acid, beta-all-trans-retinoicHMDB
Tretinoin potassium saltHMDB
Zinc salt, tretinoinHMDB
Acid, retinoicHMDB
Acid, trans-retinoicHMDB
Salt, tretinoin potassiumHMDB
Salt, tretinoin zincHMDB
Tretinoin sodium saltHMDB
all trans Retinoic acidHMDB
Retin-a microHMDB
Tretin-XHMDB
all-trans-Retinoic acidMeSH
Chemical FormulaC20H28O2
Average Mass300.4420 Da
Monoisotopic Mass300.20893 Da
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Traditional Nametretinoin
CAS Registry Number302-79-4
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI Identifier
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
InChI KeySHGAZHPCJJPHSC-YCNIQYBTSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
  • Animalia
  • Chemical Taxonomy
    Description Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
    KingdomOrganic compounds
    Super ClassLipids and lipid-like molecules
    ClassPrenol lipids
    Sub ClassRetinoids
    Direct ParentRetinoids
    Alternative Parents
    Substituents
    • Retinoic acid
    • Diterpenoid
    • Retinoid skeleton
    • Medium-chain fatty acid
    • Branched fatty acid
    • Methyl-branched fatty acid
    • Fatty acyl
    • Unsaturated fatty acid
    • Fatty acid
    • Monocarboxylic acid or derivatives
    • Carboxylic acid
    • Carboxylic acid derivative
    • Hydrocarbon derivative
    • Organooxygen compound
    • Organic oxide
    • Organic oxygen compound
    • Carbonyl group
    • Aliphatic homomonocyclic compound
    Molecular FrameworkAliphatic homomonocyclic compounds
    External Descriptors
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point181 °CNot Available
    Boiling Point462.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
    Water Solubility0.13 mg/L @ 25 °C (est)The Good Scents Company Information System
    LogP6.30Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
    Predicted Properties
    PropertyValueSource
    Water Solubility0.0048 g/LALOGPS
    logP5.66ALOGPS
    logP5.01ChemAxon
    logS-4.8ALOGPS
    pKa (Strongest Acidic)5ChemAxon
    Physiological Charge-1ChemAxon
    Hydrogen Acceptor Count2ChemAxon
    Hydrogen Donor Count1ChemAxon
    Polar Surface Area37.3 ŲChemAxon
    Rotatable Bond Count5ChemAxon
    Refractivity97.79 m³·mol⁻¹ChemAxon
    Polarizability36.85 ųChemAxon
    Number of Rings1ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveNoChemAxon
    Ghose FilterYesChemAxon
    Veber's RuleYesChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0001852
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB112204
    KNApSAcK IDNot Available
    Chemspider ID392618
    KEGG Compound IDC00777
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkTretinoin
    METLIN IDNot Available
    PubChem Compound444795
    PDB IDNot Available
    ChEBI ID15367
    Good Scents IDrw1216601
    References
    General References
    1. Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [PubMed:10997942 ]
    2. Barua AB, Olson JA: Retinoyl beta-glucuronide: an endogenous compound of human blood. Am J Clin Nutr. 1986 Apr;43(4):481-5. [PubMed:3962900 ]
    3. Napoli JL, Posch KP, Fiorella PD, Boerman MH: Physiological occurrence, biosynthesis and metabolism of retinoic acid: evidence for roles of cellular retinol-binding protein (CRBP) and cellular retinoic acid-binding protein (CRABP) in the pathway of retinoic acid homeostasis. Biomed Pharmacother. 1991;45(4-5):131-43. [PubMed:1932598 ]
    4. Giannini G, Di Marcotullio L, Ristori E, Zani M, Crescenzi M, Scarpa S, Piaggio G, Vacca A, Peverali FA, Diana F, Screpanti I, Frati L, Gulino A: HMGI(Y) and HMGI-C genes are expressed in neuroblastoma cell lines and tumors and affect retinoic acid responsiveness. Cancer Res. 1999 May 15;59(10):2484-92. [PubMed:10344762 ]
    5. Lee YF, Bao BY, Chang C: Modulation of the retinoic acid-induced cell apoptosis and differentiation by the human TR4 orphan nuclear receptor. Biochem Biophys Res Commun. 2004 Oct 22;323(3):876-83. [PubMed:15381082 ]
    6. Mercader J, Ribot J, Murano I, Felipe F, Cinti S, Bonet ML, Palou A: Remodeling of white adipose tissue after retinoic acid administration in mice. Endocrinology. 2006 Nov;147(11):5325-32. Epub 2006 Jul 13. [PubMed:16840543 ]
    7. Natsume N, Kondo S, Matsuyama Y, Sumida K, Inou H, Kawakami N, Sandell LJ, Iwata H: Analysis of cartilage-derived retinoic acid-sensitive protein in cerebrospinal fluid From patients With spinal diseases. Spine (Phila Pa 1976). 2001 Jan 15;26(2):157-60. [PubMed:11154535 ]
    8. Baron JM, Heise R, Blaner WS, Neis M, Joussen S, Dreuw A, Marquardt Y, Saurat JH, Merk HF, Bickers DR, Jugert FK: Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro. J Invest Dermatol. 2005 Jul;125(1):143-53. [PubMed:15982314 ]
    9. Paez-Pereda M, Kovalovsky D, Hopfner U, Theodoropoulou M, Pagotto U, Uhl E, Losa M, Stalla J, Grubler Y, Missale C, Arzt E, Stalla GK: Retinoic acid prevents experimental Cushing syndrome. J Clin Invest. 2001 Oct;108(8):1123-31. [PubMed:11602619 ]
    10. Meyer E, Lambert WE, De Leenheer AP: Simultaneous determination of endogenous retinoic acid isomers and retinol in human plasma by isocratic normal-phase HPLC with ultraviolet detection. Clin Chem. 1994 Jan;40(1):48-57. [PubMed:8287543 ]
    11. Masgrau-Peya E, Salomon D, Saurat JH, Meda P: In vivo modulation of connexins 43 and 26 of human epidermis by topical retinoic acid treatment. J Histochem Cytochem. 1997 Sep;45(9):1207-15. [PubMed:9283608 ]
    12. Lopez-Boado YS, Klaus M, Dawson MI, Lopez-Otin C: Retinoic acid-induced expression of apolipoprotein D and concomitant growth arrest in human breast cancer cells are mediated through a retinoic acid receptor RARalpha-dependent signaling pathway. J Biol Chem. 1996 Dec 13;271(50):32105-11. [PubMed:8943263 ]
    13. Stewart ME, Benoit AM, Downing DT, Strauss JS: Suppression of sebum secretion with 13-cis-retinoic acid: effect on individual skin surface lipids and implications for their anatomic origin. J Invest Dermatol. 1984 Jan;82(1):74-8. [PubMed:6228612 ]
    14. Tse HK, Leung MB, Woolf AS, Menke AL, Hastie ND, Gosling JA, Pang CP, Shum AS: Implication of Wt1 in the pathogenesis of nephrogenic failure in a mouse model of retinoic acid-induced caudal regression syndrome. Am J Pathol. 2005 May;166(5):1295-307. [PubMed:15855632 ]
    15. Patel JB, Huynh CK, Handratta VD, Gediya LK, Brodie AM, Goloubeva OG, Clement OO, Nanne IP, Soprano DR, Njar VC: Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice. J Med Chem. 2004 Dec 30;47(27):6716-29. [PubMed:15615521 ]
    16. Thiboutot D, Martin P, Volikos L, Gilliland K: Oxidative activity of the type 2 isozyme of 17beta-hydroxysteroid dehydrogenase (17beta-HSD) predominates in human sebaceous glands. J Invest Dermatol. 1998 Sep;111(3):390-5. [PubMed:9740229 ]