beta-amyrenone

ID: ALA461060

Cas Number: 638-97-1

PubChem CID: 12306160

Max Phase: Preclinical

Molecular Formula: C30H48O

Molecular Weight: 424.71

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Beta-Amyrenone | Beta-Amyrinone | beta-Amyrone|beta-amyrenone|638-97-1|Beta-Amyrinone|beta-Amyron|CHEMBL461060|(4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-one|EX-A6671|HY-N2925|BDBM50242248|AKOS040761409|AC-37065|CS-0023532

Canonical SMILES:  CC1(C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C30H48O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h9,21-23H,10-19H2,1-8H3/t21-,22-,23+,27+,28-,29+,30+/m0/s1

Standard InChI Key:  LIIFBMGUDSHTOU-CFYIDONUSA-N

Molfile:  

     RDKit          2D

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    3.1713  -26.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4698  -22.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4554  -26.6414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0946  -27.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7269  -25.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0166  -24.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919  -24.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
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  5 34  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA461060

   beta-Amyrone

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: 424.71

Molecular Weight (Monoisotopic): 424.3705

AlogP: 8.38

#Rotatable Bonds: ┄

Polar Surface Area: 17.07

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.97

CX LogD: 7.97

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: 3.29

References

1. Morikawa T, Kishi A, Pongpiriyadacha Y, Matsuda H, Yoshikawa M..  (2003)  Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis.,  66  (9): [PMID:14510595] [10.1021/np0301543]

2. Hata K, Hori K, Takahashi S..  (2002)  Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.,  65  (5): [PMID:12027734] [10.1021/np0104673]

3. 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]

4. Rashad AA, Mahalingam S, Keller PA..  (2014)  Chikungunya virus: emerging targets and new opportunities for medicinal chemistry.,  57  (4): [PMID:24079775] [10.1021/jm400460d]

5. Vo NNQ, Nomura Y, Muranaka T, Fukushima EO..  (2019)  Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.,  82  (12): [PMID:31774676] [10.1021/acs.jnatprod.9b00538]

6. Zhang JF,Zhong WC,Li YC,Song YQ,Xia GY,Tian GH,Ge GB,Lin S.  (2020)  Bioactivity-Guided Discovery of Human Carboxylesterase Inhibitors from the Roots of Paeonia lactiflora.,  83  (10): [PMID:32951423] [10.1021/acs.jnatprod.0c00464]

Source

Source(1):

• Scientific Literature