Sparticolin D; 4-((2S*,4S*)-2,4-dihydroxyspiro[cyclopentane-1,2'-naphtho-[1,8-de][1,3]dioxin]-5-ylidene)but-2-enoic acid

ID: ALA4551931

PubChem CID: 155555809

Max Phase: Preclinical

Molecular Formula: C19H16O6

Molecular Weight: 340.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)/C=C/C=C1\[C@@H](O)C[C@H](O)C12Oc1cccc3cccc(c13)O2

Standard InChI:  InChI=1S/C19H16O6/c20-13-10-16(21)19(12(13)6-3-9-17(22)23)24-14-7-1-4-11-5-2-8-15(25-19)18(11)14/h1-9,13,16,20-21H,10H2,(H,22,23)/b9-3+,12-6+/t13-,16-/m0/s1

Standard InChI Key:  GYUMSFUODMAKEE-SDBOVWJISA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   30.9709   -3.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7605   -4.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4531   -4.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0945   -4.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7934   -3.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0270   -6.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0259   -7.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7406   -7.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4549   -7.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1702   -7.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8852   -7.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8805   -6.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7388   -6.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4573   -6.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1692   -6.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1690   -5.2284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7323   -5.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2398   -2.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8925   -4.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4727   -3.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2707   -4.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8509   -3.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6488   -3.7459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6330   -2.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9911   -4.6637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
 13  6  1  0
 14  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 15  2  0
 13 14  2  0
 13 17  1  0
 14 15  1  0
 15 16  1  0
 16  3  1  0
  3 17  1  1
  5 18  1  6
  4 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
  2 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4551931

   ---

Molecule Features

Natural Product: No

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: 340.33

Molecular Weight (Monoisotopic): 340.0947

AlogP: 2.00

#Rotatable Bonds: 2

Polar Surface Area: 96.22

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 2.00

CX LogD: -1.25

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: 1.66

References

1. Phukhamsakda C, Macabeo APG, Huch V, Cheng T, Hyde KD, Stadler M..  (2019)  Sparticolins A-G, Biologically Active Oxidized Spirodioxynaphthalene Derivatives from the Ascomycete Sparticola junci.,  82  (10): [PMID:31599583] [10.1021/acs.jnatprod.9b00604]

Source

Source(1):

• Scientific Literature