Salvianolic acid L

ID: ALA3113339

PubChem CID: 76324956

Max Phase: Preclinical

Molecular Formula: C36H30O16

Molecular Weight: 718.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@H](Cc1ccc(O)c(O)c1)C(=O)O)C1=Cc2ccc(O)c(O)c2C(C(=O)O[C@H](Cc2ccc(O)c(O)c2)C(=O)O)C1c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C36H30O16/c37-20-5-1-15(9-24(20)41)11-27(33(45)46)51-35(49)19-13-17-4-8-23(40)32(44)30(17)31(29(19)18-3-7-22(39)26(43)14-18)36(50)52-28(34(47)48)12-16-2-6-21(38)25(42)10-16/h1-10,13-14,27-29,31,37-44H,11-12H2,(H,45,46)(H,47,48)/t27-,28-,29?,31?/m1/s1

Standard InChI Key:  CLZDRNKNWXDFQT-UNTSIKIQSA-N

Molfile:  

     RDKit          2D

 52 56  0  0  0  0  0  0  0  0999 V2000
    4.6901   -3.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6890   -4.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038   -4.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4021   -3.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1174   -3.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1181   -4.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8335   -4.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5484   -4.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5437   -3.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8278   -3.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743   -4.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4057   -5.4943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8352   -5.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1216   -5.9022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5505   -5.8993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1233   -6.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4096   -7.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4113   -7.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6992   -8.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7005   -9.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164   -9.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1324   -9.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1275   -8.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8390   -7.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8408   -7.9636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5527   -6.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4192  -10.4384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -9.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2556   -3.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9726   -3.4098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2506   -2.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2645   -4.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2628   -5.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9781   -5.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6919   -5.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6860   -4.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9702   -4.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3974   -4.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4085   -5.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6845   -2.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4015   -3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1134   -2.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6795   -2.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3894   -1.7488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9605   -1.7575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8286   -3.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5400   -2.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5354   -2.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8135   -1.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1050   -2.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8055   -0.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2468   -1.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  0
  3 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 24 25  1  0
 24 26  2  0
 16 24  1  1
 21 27  1  0
 20 28  1  0
  9 29  1  0
 29 30  1  0
 29 31  2  0
  8 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  1  0
 36 38  1  0
 35 39  1  0
 30 40  1  0
 40 41  1  0
 41 42  1  0
 40 43  1  1
 43 44  1  0
 43 45  2  0
 42 46  2  0
 46 47  1  0
 47 48  2  0
 48 49  1  0
 49 50  2  0
 50 42  1  0
 49 51  1  0
 48 52  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113339

   (2R)-2-[3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-1,2-dihydronaphthalene-1-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 718.62

Molecular Weight (Monoisotopic): 718.1534

AlogP: 3.07

#Rotatable Bonds: 11

Polar Surface Area: 289.04

Molecular Species: ACID

HBA: 14

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.69

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: -2.25

Aromatic Rings: 4

Heavy Atoms: 52

QED Weighted: 0.08

Np Likeness Score: 0.73

References

1. Chen YS, Yu HM, Shie JJ, Cheng TJ, Wu CY, Fang JM, Wong CH..  (2014)  Chemical constituents of Plectranthus amboinicus and the synthetic analogs possessing anti-inflammatory activity.,  22  (5): [PMID:24491635] [10.1016/j.bmc.2014.01.009]

Source

Source(1):

• Scientific Literature