Taraxerol

ID: ALA511822

Cas Number: 127-22-0

PubChem CID: 92097

Product Number: T651169, Order Now?

Max Phase: Preclinical

Molecular Formula: C30H50O

Molecular Weight: 426.73

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Taraxerol | Taraxerol|127-22-0|alnulin|skimmiol|tiliadin|D-Friedoolean-14-en-3beta-ol|CHEBI:9402|UNII-A32778O852|(3beta)-D-friedoolean-14-en-3-ol|CHEMBL511822|(3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol|A32778O852|D-Friedoolean-14-en-3-ol, (3beta)-|27-Norolean-14-en-3-ol, 13-methyl-, (3beta,13alpha)-|(3S,4aR,6aR,6aS,8aR,12aR,14aR,14bR)-4,4,6a,6a,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,Show More⌵

Canonical SMILES:  CC1(C)CC[C@]2(C)CC=C3[C@]4(C)CC[C@H]5C(C)(C)[C@@H](O)CC[C@]5(C)[C@H]4CC[C@@]3(C)[C@@H]2C1

Standard InChI:  InChI=1S/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3/t20-,22+,23+,24-,27-,28-,29-,30+/m0/s1

Standard InChI Key:  GGGUGZHBAOMSFJ-GADYQYKKSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   -4.2941   -1.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941   -2.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819   -2.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8654   -1.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689   -2.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585   -2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401   -2.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514   -1.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -1.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256    0.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1478   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -0.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7263   -1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214   -1.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011   -1.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049    0.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -0.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522    0.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442    1.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174    0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0062   -2.8003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0017   -3.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3759   -3.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734   -0.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734   -3.2069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562   -1.9689    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4481   -0.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7217    0.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466    2.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254    2.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 15 16  1  0
 16 18  1  0
 17 18  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  3  6  1  0
  5  4  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  5  6  1  0
  2 23  1  1
  3 24  1  0
  9 12  1  0
  3 25  1  0
 10 14  1  0
  5 26  1  1
 13 11  1  0
  6 27  1  6
 11 12  1  0
  9 28  1  6
 13 14  1  0
 10 29  1  1
  1  2  1  0
 13 30  1  6
  1  4  1  0
 17 31  1  1
  2  3  1  0
 18 32  1  1
  5  9  1  0
 21 33  1  0
 13 17  1  0
 21 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA511822

   Taraxerol

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: 426.73

Molecular Weight (Monoisotopic): 426.3862

AlogP: 8.17

#Rotatable Bonds: ┄

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.40

CX LogD: 7.40

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: 2.98

References

1. Chaturvedula VS, Schilling JK, Miller JS, Andriantsiferana R, Rasamison VE, Kingston DG..  (2004)  New cytotoxic terpenoids from the wood of Vepris punctata from the Madagascar Rainforest.,  67  (5): [PMID:15165160] [10.1021/np0303512]

2. Min BS, Na MK, Oh SR, Ahn KS, Jeong GS, Li G, Lee SK, Joung H, Lee HK..  (2004)  New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica.,  67  (12): [PMID:15620237] [10.1021/np040113m]

3. Lin LC, Chou CJ, Kuo YC..  (2001)  Cytotoxic principles from Ventilago leiocarpa.,  64  (5): [PMID:11374975] [10.1021/np000569d]

4. Tsao CC, Shen YC, Su CR, Li CY, Liou MJ, Dung NX, Wu TS..  (2008)  New diterpenoids and the bioactivity of Erythrophleum fordii.,  16  (22): [PMID:18926710] [10.1016/j.bmc.2008.09.021]

5. Gachet MS, Kunert O, Kaiser M, Brun R, Zehl M, Keller W, Muñoz RA, Bauer R, Schuehly W..  (2011)  Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense.,  74  (4): [PMID:21438586] [10.1021/np100415m]

6. Yu MS, Lee J, Lee JM, Kim Y, Chin YW, Jee JG, Keum YS, Jeong YJ..  (2012)  Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.,  22  (12): [PMID:22578462] [10.1016/j.bmcl.2012.04.081]

7. Kim HJ, Fei X, Cho SC, Choi BY, Ahn HC, Lee K, Seo SY, Keum YS..  (2015)  Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1.,  25  (23): [PMID:26508549] [10.1016/j.bmcl.2015.10.034]

Source

Source(1):

• Scientific Literature