grayanotoxin-XVIII

ID: ALA453541

Cas Number: 70474-76-9

PubChem CID: 44559345

Max Phase: Preclinical

Molecular Formula: C20H32O4

Molecular Weight: 336.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Grayanotoxin-XVIII | Grayanotoxin XVIII|70474-76-9|grayanotoxin-XVIII|CHEMBL453541|AKOS040734486|NS00093897|(1R,3S,4R,6S,8S,10R,13R,14R)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.01,10.04,8]hexadecane-3,4,6,14-tetrol

Canonical SMILES:  C=C1[C@@H]2CC[C@@H]3C[C@@]2(C[C@@H](O)[C@@]2(O)[C@H]1C[C@H](O)C2(C)C)C[C@@]3(C)O

Standard InChI:  InChI=1S/C20H32O4/c1-11-13-6-5-12-8-19(13,10-18(12,4)23)9-16(22)20(24)14(11)7-15(21)17(20,2)3/h12-16,21-24H,1,5-10H2,2-4H3/t12-,13+,14+,15+,16-,18-,19-,20+/m1/s1

Standard InChI Key:  AHMSDGIIEDDLQI-IQDQMAIWSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -2.2275  -11.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561  -13.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298  -13.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666  -12.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9716  -11.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6761  -11.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3119  -11.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936  -12.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4831  -11.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070  -12.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5301  -12.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793  -12.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967  -11.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8778  -11.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978  -13.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886  -13.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855  -12.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7928  -12.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002  -13.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744  -10.9226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4831  -10.9476    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929  -11.8582    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150  -10.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822  -13.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1139  -11.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835  -13.2636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0196  -13.9473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  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
 10 15  1  1
 12 16  1  0
 15 16  1  0
 16 17  1  1
  8 18  1  0
  8 19  1  0
  5 20  1  6
  9 21  1  1
 12 22  1  6
  1 23  2  0
  5  1  1  0
  1  9  1  0
  4  2  1  0
 10  3  1  0
  7 25  1  1
 16 24  1  0
  4 26  1  1
  2 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA453541

   Grayanotoxin XVIII

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: 336.47

Molecular Weight (Monoisotopic): 336.2301

AlogP: 2.00

#Rotatable Bonds: ┄

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: ┄

CX LogP: 0.90

CX LogD: 0.90

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: 2.97

References

1. El-Naggar SF, Doskotch RW, ODell TM, Girard L.  (1980)  Antifeedant Diterpenes For the Gypsy Moth Larvae From Kalmia latifolia: Isolation and Characterization of Ten Grayanoids,  43  (5): [10.1021/np50011a016]

2. Zhou J, Liu T, Zhang H, Zheng G, Qiu Y, Deng M, Zhang C, Yao G..  (2018)  Anti-inflammatory Grayanane Diterpenoids from the Leaves of Rhododendron molle.,  81  (1): [PMID:29272126] [10.1021/acs.jnatprod.7b00799]

3. Sun N, Zheng G, He M, Feng Y, Liu J, Wang M, Zhang H, Zhou J, Yao G..  (2019)  Grayanane Diterpenoids from the Leaves of Rhododendron auriculatum and Their Analgesic Activities.,  82  (7): [PMID:31246460] [10.1021/acs.jnatprod.9b00095]

4. Zheng G, Zhou J, Huang L, Zhang H, Sun N, Zhang H, Jin P, Yue M, Meng L, Yao G..  (2019)  Antinociceptive Grayanane Diterpenoids from the Leaves of Pieris japonica.,  82  (12): [PMID:31809052] [10.1021/acs.jnatprod.9b00569]

Source

Source(1):

• Scientific Literature