(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(acetyloxy)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-6-yl 3-(dimethylamino)propanoate hydrochloride

• ChemBase ID: 154957
• Molecular Formular: C27H44ClNO8
• Molecular Mass: 546.09316
• Monoisotopic Mass: 545.27554505
• SMILES: CC(=O)O[C@H]1[C@H]([C@@H]2[C@]([C@H](CCC2(C)C)O)([C@@]2([C@@]1(O[C@@](CC2=O)(C)C=C)C)O)C)OC(=O)CCN(C)C.Cl
• Canonical SMILES: C=C[C@@]1(C)CC(=O)[C@]2([C@@](O1)(C)[C@@H](OC(=O)C)[C@H]([C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C)OC(=O)CCN(C)C)O.Cl
• InChI: InChI=1S/C27H43NO8.ClH/c1-10-24(5)15-18(31)27(33)25(6)17(30)11-13-23(3,4)21(25)20(35-19(32)12-14-28(8)9)22(34-16(2)29)26(27,7)36-24;/h10,17,20-22,30,33H,1,11-15H2,2-9H3;1H/t17-,20-,21-,22-,24-,25-,26+,27-;/m0./s1
• InChIKey: VIRRLEDAYYYTOD-YHEOSNBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(acetyloxy)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-6-yl 3-(dimethylamino)propanoate hydrochloride
• IUPAC Traditional name: colforsin hydrochloride
• Synonyms: Colforsin dapropate hydrochloride; N,N-dimethyl-, (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(acetyloxy)-3-ethenyldodecahydro-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-1H-naphtho[2,1-b]pyran-6-yl ester b-Alanine hydrochloride; NKH 477

Database IDs

• MDL Number: MFCD00236421
• PubChem SID: 162249095
• PubChem CID: 444028

CALCULATED PROPERTIES

• Acid pKa: 11.568257
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.7326104
• LogD (pH = 7.4): 1.0413418
• Log P: 1.9257523
• Molar Refractivity: 131.748 cm^3
• Polarizability: 53.15764 Å^3
• Polar Surface Area: 122.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥25 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Condition: desiccated
• RTECS: AY5992600
• European Hazard Symbols: Highly toxic (T+)
• German water hazard class: 3
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C27H43NO8·HCl

DETAILS

Sigma Aldrich - N3290

Biochem/physiol Actions
NKH 477 is a potent, orally active adenylyl cyclase activator. It is a water soluble derivative of forskolin, and dose dependentyl increases cAMP and blocks potassium-induced contraction concetrations in smooth muscle strips (IC50 = 80 nM). NKH 477 causes relaxation of histamine treated guinea pig smooth muscle (IC50 = 32 nM).