Microdiplodiasol

ID: ALA1765409

PubChem CID: 52937070

Max Phase: Preclinical

Molecular Formula: C15H18O7

Molecular Weight: 310.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Microdiplodiasol | Microdiplodiasol|CHEBI:68283|CHEMBL1765409|Q27136776|(1S*,4S*,4aS*,9aR*)-1,4,8,9a-tetrahydroxy-6-(hydroxymethyl)-4a-methyl-1,2,3,4,4a,9a-hexahydro-9H-xanthen-9-one

Canonical SMILES:  C[C@@]12Oc3cc(CO)cc(O)c3C(=O)[C@@]1(O)[C@@H](O)CC[C@@H]2O

Standard InChI:  InChI=1S/C15H18O7/c1-14-10(18)2-3-11(19)15(14,21)13(20)12-8(17)4-7(6-16)5-9(12)22-14/h4-5,10-11,16-19,21H,2-3,6H2,1H3/t10-,11-,14-,15-/m0/s1

Standard InChI Key:  SCOQIJBVVKZZHE-GVARAGBVSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    2.2838   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2827   -0.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -1.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920    0.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7034   -0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7066   -0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220   -1.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156    0.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1351   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5699   -0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5703   -0.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8508    0.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5713   -1.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9897    1.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4112    1.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280    0.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500    1.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8485   -2.1021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280   -1.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8606   -0.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  2  3  1  0
  3  6  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1  2  2  0
  2 15  1  0
  5  8  1  0
  4 16  1  0
  6  7  1  0
  8 17  2  0
  7 10  1  0
  9 18  1  6
  9  8  1  0
 14 19  1  1
  9 10  1  0
 11 20  1  6
  5  4  2  0
 10 21  1  1
  4  1  1  0
 15 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765409

   MICRODIPLODIASOL

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: 310.30

Molecular Weight (Monoisotopic): 310.1053

AlogP: -0.54

#Rotatable Bonds: 1

Polar Surface Area: 127.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.46

CX Basic pKa: ┄

CX LogP: -0.26

CX LogD: -0.30

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.47

Np Likeness Score: 2.39

References

1. Siddiqui IN, Zahoor A, Hussain H, Ahmed I, Ahmad VU, Padula D, Draeger S, Schulz B, Meier K, Steinert M, Kurtán T, Flörke U, Pescitelli G, Krohn K..  (2011)  Diversonol and blennolide derivatives from the endophytic fungus Microdiplodia sp.: absolute configuration of diversonol.,  74  (3): [PMID:21244021] [10.1021/np100730b]

Source

Source(1):

• Scientific Literature