delta-1',3'-1'-Dehydroxypenicillide

ID: ALA2164945

PubChem CID: 71451577

Max Phase: Preclinical

Molecular Formula: C21H20O5

Molecular Weight: 352.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)/C=C/c1ccc2c(c1OC)C(=O)OCc1cc(C)cc(O)c1O2

Standard InChI:  InChI=1S/C21H20O5/c1-12(2)5-6-14-7-8-17-18(20(14)24-4)21(23)25-11-15-9-13(3)10-16(22)19(15)26-17/h5-10,22H,1,11H2,2-4H3/b6-5+

Standard InChI Key:  XBAIUNZIMJALOJ-AATRIKPKSA-N

Molfile:  

     RDKit          2D

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    4.0515   -3.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504   -4.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584   -4.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7566   -3.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4766   -4.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4694   -3.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0450   -2.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0626   -4.8586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4546   -3.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8688   -2.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4620   -4.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8885   -4.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055   -5.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8957   -5.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4686   -5.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2486   -4.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7255   -2.1211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -2.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0453   -1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2648   -5.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5331   -6.2204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3396   -3.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278   -3.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159   -3.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -3.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9157   -2.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  5  2  0
  6  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8 12  1  0
 11  9  1  0
  9 10  1  0
 10  7  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  7 17  2  0
  4 18  1  0
 18 19  1  0
 15 20  1  0
 13 21  1  0
  1 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2164945

   Neosarphenol B

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: 352.39

Molecular Weight (Monoisotopic): 352.1311

AlogP: 4.76

#Rotatable Bonds: 3

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.40

CX Basic pKa: ┄

CX LogP: 4.59

CX LogD: 4.55

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.64

Np Likeness Score: 1.41

References

1. Zhang Y, Li XM, Shang Z, Li CS, Ji NY, Wang BG..  (2012)  Meroterpenoid and diphenyl ether derivatives from Penicillium sp. MA-37, a fungus isolated from marine mangrove rhizospheric soil.,  75  (11): [PMID:23148724] [10.1021/np300377b]

Source

Source(1):

• Scientific Literature