(7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-methanol

ID: ALA12799

Chembl Id: CHEMBL12799

Cas Number: 3772-55-2

PubChem CID: 15586718

Max Phase: Preclinical

Molecular Formula: C20H30O

Molecular Weight: 286.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc2c(c1)CC[C@H]1[C@](C)(CO)CCC[C@]21C

Standard InChI:  InChI=1S/C20H30O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18,21H,5,7,9-11,13H2,1-4H3/t18-,19-,20+/m0/s1

Standard InChI Key:  WSKGRAGZAQRSED-SLFFLAALSA-N

Alternative Forms

1. Parent:

   

   ALA12799

   POMIFERIN A

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: 286.46

Molecular Weight (Monoisotopic): 286.2297

AlogP: 4.81

#Rotatable Bonds: 2

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.28

CX LogD: 5.28

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: 2.01

References

1. Tagat JR, Nazareno DV, Puar MS, McCombie SW, Ganguly AK.  (1994)  Synthesis and anti-herpes activity of some a-ring functionalized dehydroabietane derivatives,  4  (9): [10.1016/S0960-894X(01)80236-5]

2. Woldemichael GM, Wächter G, Singh MP, Maiese WM, Timmermann BN..  (2003)  Antibacterial diterpenes from Calceolaria pinifolia.,  66  (2): [PMID:12608857] [10.1021/np020380x]

3. Yang XW, Feng L, Li SM, Liu XH, Li YL, Wu L, Shen YH, Tian JM, Zhang X, Liu XR, Wang N, Liu Y, Zhang WD..  (2010)  Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr.,  18  (2): [PMID:20022253] [10.1016/j.bmc.2009.11.055]

4. González MA, Pérez-Guaita D, Correa-Royero J, Zapata B, Agudelo L, Mesa-Arango A, Betancur-Galvis L..  (2010)  Synthesis and biological evaluation of dehydroabietic acid derivatives.,  45  (2): [PMID:19892441] [10.1016/j.ejmech.2009.10.010]

5. Kaur K, Jain M, Kaur T, Jain R..  (2009)  Antimalarials from nature.,  17  (9): [PMID:19299148] [10.1016/j.bmc.2009.02.050]

6. Muñoz E, Escalona D, Salazar JR, Alarcón J, Céspedes CL..  (2013)  Insect growth regulatory effects by diterpenes from Calceolaria talcana Grau & Ehrhart (Calceolariaceae: Scrophulariaceae) against Spodoptera frugiperda and Drosophila melanogaster,  45  [10.1016/j.indcrop.2012.12.038]

7. Gao JB, Yang SJ, Yan ZR, Zhang XJ, Pu DB, Wang LX, Li XL, Zhang RH, Xiao WL..  (2018)  Isolation, Characterization, and Structure-Activity Relationship Analysis of Abietane Diterpenoids from Callicarpa bodinieri as Spleen Tyrosine Kinase Inhibitors.,  81  (4): [PMID:29578342] [10.1021/acs.jnatprod.7b01082]

8. Klein-Júnior LC, Corrêa R, Vander Heyden Y, Cechinel Filho V..  (2019)  All that glitters is not gold: Panning cytotoxic natural products and derivatives with a fused tricyclic backbone by the estimation of their leadlikeness for cancer treatment.,  166  [PMID:30684866] [10.1016/j.ejmech.2019.01.028]

9. Phan ND, Omar AM, Sun S, Maneenet J, Dibwe DF, Sato M, Kalauni SK, Toyooka N, Fujii T, Awale S..  (2022)  Abietane diterpenes from Abies spectabilis and their anti-pancreatic cancer activity against the MIA PaCa-2 cell line.,  66  [PMID:35395369] [10.1016/j.bmcl.2022.128723]

10. Zhu M, Sun J, Wu Y, Ma X, Lei F, Li Q, Jiang C, Li F..  (2023)  Synthesis and anti-proliferative activity of dehydroabietinol derivatives bearing a triazole moiety.,  14  (4): [PMID:37122546] [10.1039/d2md00427e]

Source

Source(1):

• Scientific Literature