Rhizopycnin B

ID: ALA3953782

PubChem CID: 134143819

Max Phase: Preclinical

Molecular Formula: C16H15NO7

Molecular Weight: 333.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=C(N)[C@](C)(O)c2c(oc(=O)c3c(O)cc(OC)cc23)C1=O

Standard InChI:  InChI=1S/C16H15NO7/c1-16(21)10-7-4-6(22-2)5-8(18)9(7)15(20)24-12(10)11(19)13(23-3)14(16)17/h4-5,18,21H,17H2,1-3H3/t16-/m1/s1

Standard InChI Key:  ILXPBVLQPLSZQZ-MRXNPFEDSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.5125  -10.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9233  -11.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3316  -10.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238  -13.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2234  -11.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2234  -12.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6342  -11.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289  -12.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3295  -13.0233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0421  -12.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3400  -11.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0433  -11.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7546  -11.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7680  -10.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0606  -10.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3439  -10.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135  -13.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7476  -13.0332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4599  -11.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0717   -9.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7842   -8.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9227  -13.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133  -11.3919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069  -12.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  5  6  2  0
  5  2  1  0
  6  4  1  0
  4  8  1  0
  7  2  1  0
  7  8  2  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  1  0
 11 16  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  6 17  1  0
 10 18  2  0
 13 19  1  0
 15 20  1  0
 20 21  1  0
  4 22  2  0
  5 23  1  0
 17 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3953782

   ---

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: 333.30

Molecular Weight (Monoisotopic): 333.0849

AlogP: 0.73

#Rotatable Bonds: 2

Polar Surface Area: 132.22

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.36

CX Basic pKa: ┄

CX LogP: 0.23

CX LogD: 0.22

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: 1.28

References

1. Lai D, Wang A, Cao Y, Zhou K, Mao Z, Dong X, Tian J, Xu D, Dai J, Peng Y, Zhou L, Liu Y..  (2016)  Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22.,  79  (8): [PMID:27441892] [10.1021/acs.jnatprod.6b00327]

Source

Source(1):

• Scientific Literature