1-[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15(25),16,18-heptaen-8-yl]guanidine bis(trifluoroacetic acid) dihydrate

• ChemBase ID: 153148
• Molecular Formular: C31H35F6N5O9
• Molecular Mass: 735.6281192
• Monoisotopic Mass: 735.23389705
• SMILES: c1cc2c(cc1NC(=N)N)[nH]c1c2C[C@]2([C@H]3Cc4ccc(c5c4[C@]2([C@H]1O5)CCN3CC1CC1)O)O.C(=O)(C(F)(F)F)O.C(=O)(C(F)(F)F)O.O.O
• Canonical SMILES: OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NC(=N)Nc1ccc2c(c1)[nH]c1c2C[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O.O.O
• InChI: InChI=1S/C27H29N5O3.2C2HF3O2.2H2O/c28-25(29)30-15-4-5-16-17-11-27(34)20-9-14-3-6-19(33)23-21(14)26(27,7-8-32(20)12-13-1-2-13)24(35-23)22(17)31-18(16)10-15;2*3-2(4,5)1(6)7;;/h3-6,10,13,20,24,31,33-34H,1-2,7-9,11-12H2,(H4,28,29,30);2*(H,6,7);2*1H2/t20-,24+,26+,27-;;;;/m1..../s1
• InChIKey: LCYBCOVQKUVCID-NGBJBDQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.0^1,^1^3.0^2,^2^1.0^4,^1^2.0^5,^1^0.0^1^9,^2^5]pentacosa-4(12),5,7,9,15(25),16,18-heptaen-8-yl]guanidine bis(trifluoroacetic acid) dihydrate
• IUPAC Traditional name: 1-[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.0^1,^1^3.0^2,^2^1.0^4,^1^2.0^5,^1^0.0^1^9,^2^5]pentacosa-4(12),5,7,9,15(25),16,18-heptaen-8-yl]guanidine bis(trifluoroacetic acid) dihydrate
• Synonyms: 6′-GNTI; : [(4bS,8R,8aS,14bR)-7-(cyclopropylmethyl)-5,6,7,8,8a,9,14,14b-octahydro-1,8a-dihydroxy-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazol-12-yl]-guanidine ditrifluoroacetate dihydrate; [(4bS,8R,8aS,14bR)-7-(Cyclopropylmethyl)-5,6,7,8,8a,9,14,14b-octahydro-1,8a-dihydroxy-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazol-12-yl]-guanidine ditrifluoroacetate dihydrate; 6′-Guanidinonaltrindole ditrifluoroacetate dihydrate; 6′-GNTI 二(三氟乙酸) 盐

Database IDs

• CAS Number: 35080-00-3(anhydrous)
• MDL Number: MFCD09752601
• PubChem SID: 162247288
• PubChem CID: 71311596

CALCULATED PROPERTIES

• Acid pKa: 10.203344
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -3.149548
• LogD (pH = 7.4): -0.8548294
• Log P: 1.9124707
• Molar Refractivity: 143.9154 cm^3
• Polarizability: 51.595036 Å^3
• Polar Surface Area: 130.62 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: pink to tan solid

Safety Information

• Storage Condition: desiccated; under inert gas
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.5% (HPLC)
• Empirical Formula (Hill Notation): C27H29N5O3 · 2CF3CO2H · 2H2O

DETAILS

Sigma Aldrich - G0921

Caution
Air-sensitive
Biochem/physiol Actions
6′-GNTI is a selective agonist of κ/δ opioid receptor heterodimers in the spinal cord and has the unique property of selectively activating only opioid receptor heterodimers and not homomers. 6′-GNT functions as an analgesic demonstrating that opioid receptor heterodimers are functionally relevant in vivo.