(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(pyrrolidin-1-ylmethyl)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

• ChemBase ID: 1152
• Molecular Formular: C27H33N3O8
• Molecular Mass: 527.56622
• Monoisotopic Mass: 527.22676503
• SMILES: c1cc(c2c(c1)[C@@]([C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)NCN1CCCC1)O)N(C)C)O)O)C2=O)(C)O)O
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)NCN2CCCC2)C(=O)[C@@]2([C@H]1C[C@H]1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)O)C
• InChI: InChI=1S/C27H33N3O8/c1-26(37)13-7-6-8-16(31)17(13)21(32)18-14(26)11-15-20(29(2)3)22(33)19(24(35)27(15,38)23(18)34)25(36)28-12-30-9-4-5-10-30/h6-8,14-15,20,31,33-34,37-38H,4-5,9-12H2,1-3H3,(H,28,36)/t14-,15-,20-,26+,27-/m0/s1
• InChIKey: HMEYVGGHISAPJR-IAHYZSEUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(pyrrolidin-1-ylmethyl)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: rolitetracycline; (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(pyrrolidin-1-ylmethyl)-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
• Synonyms: Rolitetracycline; Rolitetracycline; 罗利环素

Database IDs

• CAS Number: 751-97-3
• EC Number: 212-031-9
• MDL Number: MFCD00056562
• PubChem SID: 24899354; 160964615; 46507805
• PubChem CID: 5282179; 54682938

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.31439412
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.889621
• LogD (pH = 7.4): -5.4319563
• Log P: -3.8152645
• Molar Refractivity: 139.4546 cm^3
• Polarizability: 53.166935 Å^3
• Polar Surface Area: 170.87 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.08
• LOG S: -2.47
• Solubility (Water): 1.81e+00 g/l

PROPERTIES

Physical Property

• Solubility: 555 mg/mL [MERCK INDEX (1996)]

Safety Information

• RTECS: QI9150000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Grade: analytical standard

DETAILS

DrugBank - DB01301

• Drug Groups: approved
• Description: A pyrrolidinylmethyl tetracycline. [PubChem]
• Indication: Rolitetracycline is a broad-spectrum antibiotic used in cases needing high concentrations or when oral administration is impractical.
• Toxicity: Symptoms of overdose include anorexia, nausea, diarrhoea, glossitis, dysphagia, enterocolitis and inflammatory lesions (with monilial overgrowth) in the anogenital region, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia. LD₅₀=262 mg/kg (I.P. in rat).
• External Links: Wikipedia