Structure of Fmoc-Phe(4-NH2)-OH
CAS No.: 95753-56-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: Fmoc-Phe(4-NH2)-OH
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CAS No. : | 95753-56-3 |
Formula : | C24H22N2O4 |
M.W : | 402.44 |
SMILES Code : | O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CC4=CC=C(N)C=C4 |
Synonyms : |
Fmoc-Phe(4-NH2)-OH
|
MDL No. : | MFCD00237664 |
InChI Key : | VALNSJHHRPSUDO-QFIPXVFZSA-N |
Pubchem ID : | 7019927 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 30 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 8 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 114.06 |
TPSA ? Topological Polar Surface Area: Calculated from |
101.65 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.25 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.96 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.81 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.32 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.24 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.75 |
Solubility | 0.00722 mg/ml ; 0.0000179 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.8 |
Solubility | 0.000645 mg/ml ; 0.0000016 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.01 |
Solubility | 0.0000397 mg/ml ; 0.0000000986 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.94 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
1.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<3.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.95 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; zinc; In water; isopropyl alcohol; | Small portions of hydrochloric acid and zinc metal powder were added in succession to a suspension of 51.3 g (0.119 mol) 3a and 3b acids in a mixture of 800 mL of 2-propanol and 600 mL of water. The reaction mass was heated, the initial compound dissolved. Monitoring consumption of the starting compounds was performed by TLC. After completion of the reaction, 2-propanol was distilled off the mixture (pH 1) at a reduced pressure. The precipitate was boiled in 20% hydrochloric acid for 6 h. After cooling the resulting suspension was neutralized with aqueous sodium acetate to pH 4-5. The precipitate was filtered off and dried. Yield 89% (4a), 87% (4b), mp 214-215C (mp 218-219C [10]). IR spectrum nu, cm-1: 3310, 2889, 2361, 1686, 1597, 1516, 1450, 1404, 1254, 1038, 737. 1 NMR spectrum (DMSO-d6), delta, ppm: 2.70-2.78 m (1H, CH2), 2.92 d.d (1H, CH2, 2J 13.7, 3J 4.1 Hz), 4.02-4.26 m (4H, 2CH2, 2CH), 6.48 d (2Harom, 3J 8.0 Hz), 6.91 d (2Harom, 3J8.0 Hz ), 7.28-7.68 m (7H, 6CHarom, NH), 7.82 d (2Harom, 3J 7.5 Hz ). 13 NMR spectrum (DMSO-d6), delta, ppm: 36.55 (CH2), 47.10 (CH), 56.83 (CH), 65.97 (CH2), 114.20, 120.53, 125.72, 127.54, 128.07, 130.06, 141.13, 144.29, 147.28 (arom), 156.13 (CONH), 173.95 (COOH). Mass spectrum (ESI), m/z: 425.1472 [M + Na]+. C24H22N2O4. Calculated M 402.1580. |
A367212 [196808-79-4]
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