Metabolite all-trans-retinoic acid

Name

all-trans-retinoic acid

Description

Not Available

Structure

Similar Structures

Synonyms

Not Available

UNII

Not Available

CAS number

Not Available

Weight

Average: 300.442
Monoisotopic: 300.208930142

Chemical Formula

C₂₀H₂₈O₂

InChI Key

SHGAZHPCJJPHSC-YCNIQYBTSA-N

InChI

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+

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

SMILES

C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O

Reactions

Isotretinoin

all-trans-retinoic acid
- all-trans-retinoic acid
  
  4-hydroxy-all-trans-retinoic acid
  - 4-hydroxy-all-trans-retinoic acid
    
    4-oxo-all-trans-retinoic acid
    - 4-oxo-all-trans-retinoic acid
      
      4-oxo-13-cis-retinoic acid

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0390000000-af1a6974c2a7872f36c7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0090000000-82a486e1feafa5cf4f1b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00lu-2970000000-05e8c3f4df3fed93b093
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0190000000-08192331c8e265ce508b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-2890000000-2b136364b4a3a972b85b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052f-4910000000-f6c3b4ffdf3dc3f695a2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0390000000-af1a6974c2a7872f36c7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0090000000-82a486e1feafa5cf4f1b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00lu-2970000000-05e8c3f4df3fed93b093
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0190000000-08192331c8e265ce508b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-2890000000-2b136364b4a3a972b85b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052f-4910000000-f6c3b4ffdf3dc3f695a2
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	202.3292981	predicted	DarkChem Lite v0.1.0
[M-H]-	204.5572981	predicted	DarkChem Lite v0.1.0
[M-H]-	192.63275	predicted	DeepCCS 1.0 (2019)
[M-H]-	202.3292981	predicted	DarkChem Lite v0.1.0
[M-H]-	204.5572981	predicted	DarkChem Lite v0.1.0
[M-H]-	202.3292981	predicted	DarkChem Lite v0.1.0
[M-H]-	204.5572981	predicted	DarkChem Lite v0.1.0
[M-H]-	192.63275	predicted	DeepCCS 1.0 (2019)
[M-H]-	192.63275	predicted	DeepCCS 1.0 (2019)
[M+H]+	194.99077	predicted	DeepCCS 1.0 (2019)
[M+H]+	194.99077	predicted	DeepCCS 1.0 (2019)
[M+H]+	194.99077	predicted	DeepCCS 1.0 (2019)
[M+Na]+	202.33412	predicted	DeepCCS 1.0 (2019)
[M+Na]+	202.33412	predicted	DeepCCS 1.0 (2019)
[M+Na]+	202.33412	predicted	DeepCCS 1.0 (2019)

External Links

BindingDB: 323588
PharmGKB: PA164746900
Wikipedia: Tretinoin

Predicted Properties

Property	Value	Source
Water Solubility	0.00477 mg/mL	ALOGPS
logP	5.66	ALOGPS
logP	5.01	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.76	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	37.3 Å²	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	97.79 m³·mol^-1	Chemaxon
Polarizability	36.85 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Metabolite all-trans-retinoic acid

Structure for all-trans-retinoic acid

Collision Cross Sections (CCS)