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[ CAS No. 495-02-3 ] {[proInfo.proName]}

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Chemical Structure| 495-02-3
Chemical Structure| 495-02-3
Structure of 495-02-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 495-02-3 ]

CAS No. :495-02-3 MDL No. :MFCD00075948
Formula : C19H22O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RSDDHGSKLOSQFK-RVDMUPIBSA-N
M.W : 298.38 Pubchem ID :1550607
Synonyms :
7-Geranyloxycoumarin

Calculated chemistry of [ 495-02-3 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.32
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 91.29
TPSA : 39.44 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.96
Log Po/w (XLOGP3) : 5.1
Log Po/w (WLOGP) : 4.86
Log Po/w (MLOGP) : 3.51
Log Po/w (SILICOS-IT) : 5.13
Consensus Log Po/w : 4.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.84
Solubility : 0.00428 mg/ml ; 0.0000143 mol/l
Class : Moderately soluble
Log S (Ali) : -5.67
Solubility : 0.000635 mg/ml ; 0.00000213 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.9
Solubility : 0.000378 mg/ml ; 0.00000127 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.43

Safety of [ 495-02-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 495-02-3 ]

* 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.

  • Upstream synthesis route of [ 495-02-3 ]
  • Downstream synthetic route of [ 495-02-3 ]

[ 495-02-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 93-35-6 ]
  • [ 6138-90-5 ]
  • [ 495-02-3 ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate In N,N-dimethyl-formamide for 3 h; Inert atmosphere; Reflux Aurapten (5). Geranyl bromide (159 l, 0.80 mmol) was added to a stirred mixture of umbelliferone (2) (100 mg, 0.62 mmol) and K2CO3 (171 mg, 1.24 mmol) in dry DMF (5 ml) under argon. The reaction mixture was stirred under reflux for 3 h. The reaction mixture was neutralised by addition of aq. HCl (1M). The resulting brown residue was added in DCM (20 ml), washed with water (2 .x. 20 ml), brine (30 ml) and dried Na2SO4). Removal of solvent yielded a brown oil, which was purified by flash column chromatography, eluting with diethylether-hexane (1:1) to give a white powder 5 (181 mg, 76percent): 1H NMR (CDCl3, 700 MHz) 7.64 (1H, d, J = 9.5 Hz, H-4), 7.36 (1H, d, J = 8.6 Hz, H-5), 6.86 (1H, dd, J = 8.4, 2.4 Hz, H-6), 6.82 (1H, d, J = 2.4 Hz, H-8), 6.25 (1H, d, J = 9.5 Hz, H-3), 5.47 (1H, tq, J = 6.6, 1.4 Hz, H-2'), 5.08 (2H, m, H-1'), 4.61 (2H, d, J = 6.6 Hz, H-1'), 2.13 (2H, m, H-5'), 2.09 (2H, m, H-4'), 1.76 (3H, brs, H-9'), 1.67 (3H, brs, H-8'), 1.60 (3H, brs, H-10'); 13C NMR (CDCl3, 175 MHz) 162.2 (C, C-7), 161.3 (C, C-2), 155.9 (C, C-8a), 143.4 (CH, C-4), 142.4 (C-3'), 131.9 (C, C-7'), 128.7 (CH, C-5), 123.6 (CH, C-6'), 118.4 (CH, C-2'), 113.2 (CH, C-6), 112.9 (CH, C-3), 112.4 (C, C-4a), 101.6 (CH, C-8), 65.5 (CH2, C-1'), 39.5 (CH2, C-4'), 26.2 (CH2, C-5'), 25.6 (CH3, C-8'), 17.7 (CH3, C-10'), 16.7 (CH3, C-9'); HR-FABMS (pos) m/z 299.3877 [M + H]+ (calcd. for C19H23O3, 299.3860).
Reference: [1] Phytochemistry, 1998, vol. 47, # 8, p. 1521 - 1525
[2] Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 10, p. 1171 - 1174
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 784 - 788
[4] Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 7-8, p. 405 - 424
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 8, p. 1604 - 1610
[6] Journal of Medicinal Chemistry, 1992, vol. 35, # 10, p. 1877 - 1882
[7] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5770 - 5773
[8] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 134 - 142
[9] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 19, p. 4654 - 4658
[10] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 13, p. 2920 - 2925
[11] Journal of Natural Products, 2017, vol. 80, # 6, p. 1939 - 1943
[12] Phytotherapy Research, 2017, vol. 31, # 9, p. 1369 - 1375
  • 2
  • [ 93-35-6 ]
  • [ 5389-87-7 ]
  • [ 495-02-3 ]
Reference: [1] Phytochemistry, 2004, vol. 65, # 22, p. 3021 - 3027
  • 3
  • [ 106-24-1 ]
  • [ 495-02-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 13, p. 2920 - 2925
  • 4
  • [ 142628-36-2 ]
  • [ 495-02-3 ]
  • [ 5980-09-6 ]
Reference: [1] Phytochemistry (Elsevier), 1992, vol. 31, # 4, p. 1363 - 1366
[2] Phytochemistry (Elsevier), 1992, vol. 31, # 4, p. 1363 - 1366
  • 5
  • [ 1181223-78-8 ]
  • [ 495-02-3 ]
Reference: [1] Journal of Natural Products, 2009, vol. 72, # 9, p. 1702 - 1704
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