Dehydroaustinol

ID: ALA4534615

PubChem CID: 24871106

Max Phase: Preclinical

Molecular Formula: C25H28O8

Molecular Weight: 456.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1[C@@]23C(=O)O[C@H](C)[C@]24O[C@@]2(C(=C)[C@]5(C=CC(=O)OC5(C)C)CC[C@]32C)[C@H](O)[C@@]1(C)OC4=O

Standard InChI:  InChI=1S/C25H28O8/c1-12-21(7)16(27)24-13(2)22(9-8-15(26)31-19(22,4)5)11-10-20(24,6)23(12)17(28)30-14(3)25(23,33-24)18(29)32-21/h8-9,14,16,27H,1-2,10-11H2,3-7H3/t14-,16-,20-,21+,22+,23+,24+,25-/m1/s1

Standard InChI Key:  IQBUQLYYAHHCGX-VRTAWDDNSA-N

Molfile:  

 
     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
   34.3043  -11.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5070  -11.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7212  -12.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5070  -10.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2207  -10.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9315  -10.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5040   -9.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0835  -10.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0835  -11.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7969  -11.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7969  -10.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2210   -9.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9327   -9.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6416   -9.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6453   -8.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9337   -7.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2184   -8.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3684  -11.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7881   -9.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5027   -7.9853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8654   -7.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1221   -8.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6502   -7.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6794   -8.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3584   -7.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0199   -9.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1135   -9.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8463   -9.9515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5908  -10.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9390   -9.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8051   -8.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2124  -10.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9262   -7.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  7  1  0
  5  6  1  0
  6 13  1  0
 12  7  1  0
  8  9  1  0
  8 11  2  0
  9 10  1  0
 10  2  1  0
  2  4  1  0
  4 11  1  1
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  9 18  2  0
  7 19  2  0
 17 20  1  6
 16 21  1  0
 14 24  1  0
 15 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 14 26  1  6
 24 27  1  0
 26 28  1  0
 28 27  1  0
 26 29  2  0
 27 30  1  1
 12 31  1  1
 24 31  1  1
 13 32  1  6
 16 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4534615

   NCGC00179938-02_C25H28O8_(1'S,2'R,3R,7'R,8'R,9'S,13'R)-8'-Hydroxy-2,2,2',9',13'-pentamethyl-6',16'-bis(methylene)-6H-spiro[pyran-3,5'-[10,14,17]trioxapentacyclo[7.6.1.1~7,12~.0~1,12~.0~2,7~]heptadecane]-6,11',15'-trione

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.49

Molecular Weight (Monoisotopic): 456.1784

AlogP: 1.91

#Rotatable Bonds: ┄

Polar Surface Area: 108.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.74

CX Basic pKa: ┄

CX LogP: 2.08

CX LogD: 2.08

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 2.14

References

1. Bai M, Zheng CJ, Huang GL, Mei RQ, Wang B, Luo YP, Zheng C, Niu ZG, Chen GY..  (2019)  Bioactive Meroterpenoids and Isocoumarins from the Mangrove-Derived Fungus Penicillium sp. TGM112.,  82  (5): [PMID:30990038] [10.1021/acs.jnatprod.8b00866]

Source

Source(1):

• Scientific Literature