Bipolaricin D

ID: ALA4472781

PubChem CID: 155535887

Max Phase: Preclinical

Molecular Formula: C25H34O4

Molecular Weight: 398.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=C[C@H]1C[C@H](C)[C@]2(CC[C@]3(C)C[C@@H]4C(C)=CC(=O)[C@H]4/C(C(=O)O)=C\C[C@H]32)O1

Standard InChI:  InChI=1S/C25H34O4/c1-14(2)10-17-12-16(4)25(29-17)9-8-24(5)13-19-15(3)11-20(26)22(19)18(23(27)28)6-7-21(24)25/h6,10-11,16-17,19,21-22H,7-9,12-13H2,1-5H3,(H,27,28)/b18-6+/t16-,17-,19+,21+,22-,24+,25-/m0/s1

Standard InChI Key:  CTSVZRAXIDMCJX-MDVOPQILSA-N

Molfile:  

 
     RDKit          2D

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    4.8280  -15.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8280  -13.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4031  -13.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5854  -15.9476    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6942  -12.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9804  -14.5526    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4238  -12.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1074  -12.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4698  -13.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437  -14.2100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5675  -12.8527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259  -14.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6
  2  3  1  0
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  5  1  1  0
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  6  7  2  0
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  9  7  1  0
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 12 13  1  0
 13  1  1  0
  1 10  1  0
 14 15  1  0
 15 16  1  0
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 17 18  2  0
 18 14  1  0
 18 19  1  0
 16 20  2  0
 11 21  1  1
 14 22  1  1
  5 23  1  1
  3 24  1  6
 10 25  1  6
 24 26  2  0
 26 27  1  0
 26 28  1  0
 15 29  1  6
  6 30  1  0
 30 31  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4472781

   ---

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: 398.54

Molecular Weight (Monoisotopic): 398.2457

AlogP: 5.10

#Rotatable Bonds: 2

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.39

CX Basic pKa: ┄

CX LogP: 4.81

CX LogD: 1.91

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: 3.13

References

1. Liu M, Sun W, Shen L, Hao X, Al Anbari WH, Lin S, Li H, Gao W, Wang J, Hu Z, Zhang Y..  (2019)  Bipolaricins A-I, Ophiobolin-Type Tetracyclic Sesterterpenes from a Phytopathogenic Bipolaris sp. Fungus.,  82  (10): [PMID:31573805] [10.1021/acs.jnatprod.9b00744]

Source

Source(1):

• Scientific Literature