4-epi-2-Deacetyltinosinenoside D

ID: ALA4072073

PubChem CID: 137639591

Max Phase: Preclinical

Molecular Formula: C34H42O15

Molecular Weight: 690.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)O[C@H]2C[C@H](O)[C@H](O)[C@@H]3[C@@H]2CC[C@@]2(O)C(=O)O[C@H](c4ccoc4)C[C@@]32C)ccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C34H42O15/c1-33-13-23(17-8-10-45-15-17)49-32(42)34(33,43)9-7-18-21(12-19(36)27(38)26(18)33)46-25(37)6-4-16-3-5-20(22(11-16)44-2)47-31-30(41)29(40)28(39)24(14-35)48-31/h3-6,8,10-11,15,18-19,21,23-24,26-31,35-36,38-41,43H,7,9,12-14H2,1-2H3/b6-4+/t18-,19+,21+,23+,24-,26+,27+,28-,29+,30-,31-,33+,34-/m1/s1

Standard InChI Key:  XPACJUIOXALHPS-YVQBTNBBSA-N

Molfile:  

     RDKit          2D

 51 56  0  0  0  0  0  0  0  0999 V2000
   35.9685  -18.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9685  -19.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6698  -19.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6698  -18.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3669  -18.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3658  -19.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0622  -19.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7666  -19.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0686  -18.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7660  -18.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4714  -18.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4805  -17.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7831  -17.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0725  -17.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7916  -16.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4555  -15.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2153  -15.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.4022  -15.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1416  -15.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7578  -17.9288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0620  -19.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3600  -17.9204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.3579  -20.3492    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   40.1684  -18.7591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.6621  -20.7578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.6708  -17.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2595  -18.3271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9506  -21.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9429  -21.9769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2467  -20.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5352  -21.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8314  -20.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8423  -19.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1393  -19.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4268  -19.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4217  -20.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1253  -21.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1474  -18.6808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4438  -18.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7225  -19.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0115  -19.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3125  -19.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6037  -19.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5929  -20.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2971  -21.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0121  -20.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9009  -19.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2877  -21.9210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8804  -21.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7174  -21.1156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9106  -18.6358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 13 15  1  1
 10 20  1  1
  9 21  1  1
  5 22  1  6
  6 23  1  1
 11 24  2  0
  3 25  1  1
  4 26  1  6
  1 27  1  6
 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 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
 34 38  1  0
 38 39  1  0
 35 40  1  0
 41 40  1  1
 41 42  1  0
 41 46  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 43 47  1  1
 45 48  1  1
 44 49  1  6
 46 50  1  6
 47 51  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072073

   ---

Molecule Features

Natural Product: No

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: 690.70

Molecular Weight (Monoisotopic): 690.2524

AlogP: -0.03

#Rotatable Bonds: 8

Polar Surface Area: 235.04

Molecular Species: NEUTRAL

HBA: 15

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.79

CX Basic pKa: ┄

CX LogP: -0.13

CX LogD: -0.13

Aromatic Rings: 2

Heavy Atoms: 49

QED Weighted: 0.14

Np Likeness Score: 2.42

References

1. Jiang H, Zhang GJ, Liu YF, Wang HS, Liang D..  (2017)  Clerodane Diterpenoid Glucosides from the Stems of Tinospora sinensis.,  80  (4): [PMID:28358196] [10.1021/acs.jnatprod.6b00976]

Source

Source(1):

• Scientific Literature