(4S,5R,6S,7R)-4,5,6,11-tetrahydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.02,7.012,16]heptadeca-1(17),2,10,12(16)-tetraen-9-one

• ChemBase ID: 154623
• Molecular Formular: C14H13NO7
• Molecular Mass: 307.25552
• Monoisotopic Mass: 307.06920176
• SMILES: c1c2c(c(c3c1OCO3)O)C(=O)N[C@@H]1C2=C[C@@H]([C@H]([C@H]1O)O)O
• Canonical SMILES: O[C@H]1C=C2[C@H]([C@@H]([C@@H]1O)O)NC(=O)c1c2cc2OCOc2c1O
• InChI: InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1
• InChIKey: LZAZURSABQIKGB-AEKGRLRDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R,6S,7R)-4,5,6,11-tetrahydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.0^2,^7.0^1^2,^1^6]heptadeca-1(17),2,10,12(16)-tetraen-9-one
• IUPAC Traditional name: (4S,5R,6S,7R)-4,5,6,11-tetrahydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.0^2,^7.0^1^2,^1^6]heptadeca-1(17),2,10,12(16)-tetraen-9-one
• Synonyms: (2S-(2-alpha,3-beta,4-beta,4a-beta))-3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one; 3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one; BRN 1087400; Lycoricidin-A; Lycoricidinol; NSC 266535; Narciclasine

Database IDs

• CAS Number: 29477-83-6
• MDL Number: MFCD01729949
• PubChem SID: 162248761
• PubChem CID: 72376

CALCULATED PROPERTIES

• Acid pKa: 8.437841
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.9161605
• LogD (pH = 7.4): -0.9534009
• Log P: -0.91566396
• Molar Refractivity: 72.0072 cm^3
• Polarizability: 27.742916 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: nwg
• Risk Statements: 46
• Safety Statements: 36
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H340
• GHS Precautionary statements: P201-P308 + P313
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H13NO7

DETAILS

Sigma Aldrich - N9789

Biochem/physiol Actions
Narciclasine is a Rho/Rho kinase/LIM kinase/cofilin signaling pathway activator. Also narciclasine is an actin stress fiber formation inducer; a plant growth modulator.