Perulactone H

ID: ALA2408039

PubChem CID: 73350642

Max Phase: Preclinical

Molecular Formula: C28H40O7

Molecular Weight: 488.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1C(=O)OC[C@H]1C[C@@H](O)[C@](C)(O)[C@@]1(O)CC[C@@]2(O)[C@@H]3CC=C4CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C28H40O7/c1-16-17(15-35-23(16)31)14-22(30)26(4,32)28(34)13-12-27(33)20-9-8-18-6-5-7-21(29)25(18,3)19(20)10-11-24(27,28)2/h5,7-8,16-17,19-20,22,30,32-34H,6,9-15H2,1-4H3/t16-,17-,19+,20-,22-,24+,25+,26+,27-,28-/m1/s1

Standard InChI Key:  GRNQXNIWEPWACV-CLIKSGLPSA-N

Molfile:  

     RDKit          2D

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   28.2578  -21.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2567  -20.3715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6406  -23.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6406  -24.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3526  -24.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3526  -23.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0648  -23.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0613  -24.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7701  -24.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4870  -24.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7772  -23.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.5036  -21.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7824  -22.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2131  -22.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2041  -23.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9829  -23.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.9973  -21.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0697  -21.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6150  -21.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4240  -21.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0308  -22.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7498  -21.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5870  -20.8334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7675  -20.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3526  -22.2029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4999  -21.9861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3331  -20.2553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1993  -23.8739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7700  -23.8573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.9374  -22.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8204  -21.9778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2077  -21.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0574  -22.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4784  -22.6280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  2  0
  4  7  1  0
  5  6  1  0
  6  9  1  0
  8  7  1  0
  8  9  1  0
  8 12  1  0
  9 10  2  0
 10 11  1  0
 11 13  1  0
 12 13  1  0
 12 15  1  0
 13 17  1  0
 16 14  1  0
 14 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 20  2  1  0
  2 21  1  0
 21 22  1  0
 23 22  1  6
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
  7 28  2  0
 25 29  2  0
 21 30  1  6
 17 31  1  6
 12 32  1  6
 24 33  1  6
 20 34  1  6
 16 35  1  1
  8 36  1  1
 13 37  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2408039

   (3R,4S)-4-[(2R,3S)-3-[(8R,9S,10R,13S,14R,17R)-14,17-dihydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2,3-dihydroxybutyl]-3-methyloxolan-2-one

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: 488.62

Molecular Weight (Monoisotopic): 488.2774

AlogP: 2.45

#Rotatable Bonds: 4

Polar Surface Area: 124.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.72

CX Basic pKa: ┄

CX LogP: 1.96

CX LogD: 1.96

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.35

Np Likeness Score: 2.76

References

1. Ozawa M, Morita M, Hirai G, Tamura S, Kawai M, Tsuchiya A, Oonuma K, Maruoka K, Sodeoka M..  (2013)  Contribution of Cage-Shaped Structure of Physalins to Their Mode of Action in Inhibition of NF-κB Activation.,  4  (8): [PMID:24900739] [10.1021/ml400144e]

2. Xu YM, Wijeratne EMK, Babyak AL, Marks HR, Brooks AD, Tewary P, Xuan LJ, Wang WQ, Sayers TJ, Gunatilaka AAL..  (2017)  Withanolides from Aeroponically Grown Physalis peruviana and Their Selective Cytotoxicity to Prostate Cancer and Renal Carcinoma Cells.,  80  (7): [PMID:28617598] [10.1021/acs.jnatprod.6b01129]

Source

Source(1):

• Scientific Literature