Physalin U

ID: ALA4873888

PubChem CID: 163039001

Max Phase: Preclinical

Molecular Formula: C29H34O11

Molecular Weight: 558.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@@H]1CC(=O)[C@]2(C)[C@H]3CC[C@@]4(O)C(=O)O[C@@]5(C)[C@H]6C[C@]7(C)[C@@H](CO[C@@]8(O[C@]45[C@H]7C8=O)[C@@H]3C[C@H]3O[C@]32C1)C(=O)O6

Standard InChI:  InChI=1S/C29H34O11/c1-23-10-18-25(3)29-19(23)20(31)28(40-29,36-11-15(23)21(32)37-18)14-8-17-27(38-17)9-12(35-4)7-16(30)24(27,2)13(14)5-6-26(29,34)22(33)39-25/h12-15,17-19,34H,5-11H2,1-4H3/t12-,13+,14-,15+,17-,18-,19+,23-,24+,25+,26-,27-,28-,29+/m1/s1

Standard InChI Key:  CHZSVNLGISWUMU-NFAFBBCCSA-N

Molfile:  

 
     RDKit          2D

 46 54  0  0  0  0  0  0  0  0999 V2000
   18.0607   -5.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0607   -6.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7771   -6.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7771   -4.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4897   -5.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2071   -4.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9146   -5.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9349   -3.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2100   -4.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6413   -4.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6185   -4.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7771   -4.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4813   -4.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1959   -5.7784    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.4485   -5.9715    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.9160   -6.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0613   -4.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0622   -4.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3545   -3.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0657   -4.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7776   -2.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0665   -2.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3541   -2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7768   -2.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4942   -2.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2065   -2.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4993   -3.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7915   -3.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8764   -5.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1770   -4.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0622   -1.6693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2293   -3.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5274   -2.7451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3451   -2.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4043   -3.4716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3331   -4.5494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8393   -5.1603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0223   -5.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0622   -3.3106    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3459   -6.6092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1984   -6.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4818   -6.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4752   -7.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1907   -7.4307    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.3274   -3.3077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3490   -7.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3 42  1  0
  5  4  1  0
  5 42  1  0
  5  6  1  0
 16  7  1  0
  6  7  1  0
  6  9  1  0
  7 11  1  0
 10  8  1  0
  8  9  1  0
  4 12  2  0
  5 13  1  1
  6 14  1  6
  7 15  1  1
 41 16  1  0
 10 17  1  6
 10 19  1  0
 11 18  1  0
 20 18  1  0
 19 20  1  0
 19 23  1  0
 20 28  1  0
 28 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 28 30  1  1
 22 31  1  1
 10 32  1  0
 32 33  1  0
 33 23  1  0
 23 34  1  6
 32 35  2  0
 19 36  1  6
 11 36  1  0
 18 37  2  0
 11 38  1  6
 20 39  1  1
  2 40  1  6
 42 41  1  0
 42 43  1  1
 41 43  1  0
 41 44  1  6
 38 29  1  0
 27 45  1  1
 40 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873888

   ---

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: 558.58

Molecular Weight (Monoisotopic): 558.2101

AlogP: 0.62

#Rotatable Bonds: 1

Polar Surface Area: 147.19

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.22

CX Basic pKa: ┄

CX LogP: 1.26

CX LogD: 1.26

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.36

Np Likeness Score: 3.67

References

1. Xu GB, Xu YM, Wijeratne EMK, Ranjbar F, Liu MX, Gunatilaka AAL..  (2021)  Cytotoxic Physalins from Aeroponically Grown Physalis acutifolia.,  84  (2.0): [PMID:33586438] [10.1021/acs.jnatprod.0c00380]

Source

Source(1):

• Scientific Literature