7-oxocallitrisic acid

ID: ALA597919

Chembl Id: CHEMBL597919

Cas Number: 18684-55-4

PubChem CID: 29212

Max Phase: Preclinical

Molecular Formula: C20H26O3

Molecular Weight: 314.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 7-Oxocallitrisic Acid | 7-OXODEHYDROABIETIC ACID|18684-55-4|I8PNL8FLID|(1R,4aS,10aR)-1,4a-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid|Podocarpa-8,11,13-trien-15-oic acid, 13-isopropyl-7-oxo-|7-Ketodehydroabietic acid|1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-9-oxo-, (1R,4aS,10aR)-|UNII-I8PNL8FLID|BRN 3216723|7-oxocallitrisic acid|13-Isopropyl-7-oxopodocarpa-8,11,13-trien-15-oic acid|7-ketodehydro-abietic Show More⌵

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

Standard InChI:  InChI=1S/C20H26O3/c1-12(2)13-6-7-15-14(10-13)16(21)11-17-19(15,3)8-5-9-20(17,4)18(22)23/h6-7,10,12,17H,5,8-9,11H2,1-4H3,(H,22,23)/t17-,19-,20-/m1/s1

Standard InChI Key:  MSWJSDLNPCSSNW-MISYRCLQSA-N

Alternative Forms

1. Parent:

   

   ALA597919

   7-Oxodehydroabietic 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: 314.43

Molecular Weight (Monoisotopic): 314.1882

AlogP: 4.55

#Rotatable Bonds: 2

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.14

CX Basic pKa: ┄

CX LogP: 4.60

CX LogD: 1.53

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.87

Np Likeness Score: 1.96

References

1. 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]

2. Cui YM, Yasutomi E, Otani Y, Ido K, Yoshinaga T, Sawada K, Ohwada T..  (2010)  Design, synthesis, and characterization of BK channel openers based on oximation of abietane diterpene derivatives.,  18  (24): [PMID:21067932] [10.1016/j.bmc.2010.09.072]

3. Xu J, Sun Y, Wang M, Ren Q, Li S, Wang H, Sun X, Jin DQ, Sun H, Ohizumi Y, Guo Y..  (2015)  Bioactive Diterpenoids from the Leaves of Callicarpa macrophylla.,  78  (7): [PMID:26110519] [10.1021/acs.jnatprod.5b00018]

4. Kim CS, Subedi L, Kim SY, Choi SU, Kim KH, Lee KR..  (2016)  Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities.,  79  (2): [PMID:26812172] [10.1021/acs.jnatprod.5b01053]

5. Jiang J, Liu Y, Yang S, Peng H, Liu J, Cheng YX, Li N..  (2021)  Photoaffinity-Based Chemical Proteomics Reveals 7-Oxocallitrisic Acid Targets CPT1A to Trigger Lipogenesis Inhibition.,  12  (12.0): [PMID:34917253] [10.1021/acsmedchemlett.1c00316]

Source

Source(1):

• Scientific Literature