Metabolite Doxorubicinol

Name

Doxorubicinol

Description

Not Available

Structure

Similar Structures

Synonyms

Not Available

UNII

HUH05KI4CF

CAS number

Not Available

Weight

Average: 545.5351
Monoisotopic: 545.189710839

Chemical Formula

C₂₇H₃₁NO₁₁

InChI Key

NKZRZOVSJNSBFR-FEMMEMONSA-N

InChI

InChI=1S/C27H31NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,16-,17-,22+,27-/m0/s1

IUPAC Name

(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

SMILES

COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3C[C@](O)(C[C@H](O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)C3=C1O)[C@@H](O)CO)C2=O

Reactions

Doxorubicin

Doxorubicinol
- Doxorubicinol
  
  Doxorubicinol deoxaglycone
  - Doxorubicinol deoxaglycone
    
    4-O-demethyl deoxaglycone doxorubicinol
    - 4-O-demethyl deoxaglycone doxorubicinol
      
      Demethyldeoxaglycone doxorubicinol 4-O-sulfate
    - 4-O-demethyl deoxaglycone doxorubicinol
      
      Demethyldeoxaglycone doxorubicinol 4-O-b-glucuronide
- Doxorubicinol
  
  Doxorubicine hydroxyaglycone

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-05cu-9202330000-293431fa9a3beabb905a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-0003090000-05502910997af5953ee1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-0009240000-5c2f13499ad064f02d7a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-0304190000-11c90b88c0c6a00f7215
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000t-0109220000-4c248b06b6ba2b74fc82
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-029t-2930640000-05f6f11d3f5be78c0b54
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0gc3-0329850000-d6a351a5f1d6ea0e6186

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	243.1914641	predicted	DarkChem Lite v0.1.0
[M-H]-	243.7044641	predicted	DarkChem Lite v0.1.0
[M-H]-	222.04445	predicted	DeepCCS 1.0 (2019)
[M+H]+	242.8042641	predicted	DarkChem Lite v0.1.0
[M+H]+	244.5224641	predicted	DarkChem Lite v0.1.0
[M+H]+	223.86934	predicted	DeepCCS 1.0 (2019)
[M+Na]+	243.4851641	predicted	DarkChem Lite v0.1.0
[M+Na]+	244.1444641	predicted	DarkChem Lite v0.1.0
[M+Na]+	229.64075	predicted	DeepCCS 1.0 (2019)

External Links

Human Metabolome Database: HMDB0041884
ChemSpider: 75768
ChEBI: 133817
ChEMBL: CHEMBL3277946
ZINC: ZINC000060183860

Predicted Properties

Property	Value	Source
Water Solubility	1.49 mg/mL	ALOGPS
logP	0.35	ALOGPS
logP	-0.041	Chemaxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.21	Chemaxon
pKa (Strongest Basic)	9.52	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	12	Chemaxon
Hydrogen Donor Count	7	Chemaxon
Polar Surface Area	209.23 Å²	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	135.36 m³·mol^-1	Chemaxon
Polarizability	55.18 Å³	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Metabolite Doxorubicinol

Structure for Doxorubicinol

Collision Cross Sections (CCS)