methyl 2,6,13-trimethyl-12-oxo-8-phenylcarbonyloxy-(1S,2S,6R,8R,13S)-tetracyclo[11.2.1.01,10.02,7]hexadecane-6-carboxylate

ID: ALA520840

PubChem CID: 44576077

Max Phase: Preclinical

Molecular Formula: C28H36O5

Molecular Weight: 452.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]1(C)CCC[C@@]2(C)[C@H]1[C@H](OC(=O)c1ccccc1)C[C@H]1CC(=O)[C@@]3(C)CC[C@]12C3

Standard InChI:  InChI=1S/C28H36O5/c1-25-13-14-28(17-25)19(16-21(25)29)15-20(33-23(30)18-9-6-5-7-10-18)22-26(2,24(31)32-4)11-8-12-27(22,28)3/h5-7,9-10,19-20,22H,8,11-17H2,1-4H3/t19-,20+,22-,25-,26+,27-,28-/m0/s1

Standard InChI Key:  HIOORIZOEGBBAV-KOYDBKGUSA-N

Molfile:  

     RDKit          2D

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   -0.6684  -23.2446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6678  -25.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708  -24.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960  -21.5892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819  -21.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674  -21.5964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 15  1  6
  6  7  1  0
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  5  6  1  0
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  1  2  1  0
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  9 13  1  0
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  2  3  1  0
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  5 14  1  1
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  5  9  1  0
  6 33  1  6
 34 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA520840

   methyl (1S,2S,6R,7R,8R,10S,13S)-8-benzoyloxy-2,6,13-trimethyl-12-oxotetracyclo[11.2.1.01,10.02,7]hexadecane-6-carboxylate

Molecule Features

Natural Product: No

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: 452.59

Molecular Weight (Monoisotopic): 452.2563

AlogP: 5.37

#Rotatable Bonds: 3

Polar Surface Area: 69.67

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.83

CX LogD: 5.83

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.58

Np Likeness Score: 2.34

References

1. Miyahara T, Hayashi T, Matsuda S, Yamada R, Ikeda K, Tonoyama H, Komiyama H, Matsumoto M, Nemoto N, Sankawa U.  (1996)  Inhibitory effects of scopadulcic acid B and its derivatives on bone resorption and osteoclast formation in vitro,  6  (9): [10.1016/0960-894X(96)00173-4]

2. Hayashi T, Sugimoto T, Takewaki N, Takeguchi N, Tran VD, O'Connor SJ, Rucker PV, Overman LE.  (1995)  Silyl ethers of cycloheptene, novel proton pump inhibitors obtained during the total synthesis of the scopadulcic acids,  5  (24): [10.1016/0960-894X(95)00493-8]

3. Hayashi T, Asano S, Mizutani M, Takeguchi N, Kojima T, Okamura K, Morita N..  (1991)  Scopadulciol, an inhibitor of gastric H+, K(+)-ATPase from Scoparia dulcis, and its structure-activity relationships.,  54  (3): [PMID:1659612] [10.1021/np50075a008]

Source

Source(1):

• Scientific Literature