halisulfate 1

ID: ALA387584

PubChem CID: 23662099

Max Phase: Preclinical

Molecular Formula: C31H47NaO6S

Molecular Weight: 548.79

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Halisulfate 1 | halisulfate 1, (rel)-|halisulfate 1|CHEBI:69280|CHEMBL387584|SCHEMBL3537034|Q27137619|sodium;[(E,2R,3R)-1-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-9-(2,5-dihydroxyphenyl)-3,7-dimethylnon-7-en-2-yl] sulfate

Canonical SMILES:  CC1=CC[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1C[C@@H](OS(=O)(=O)[O-])[C@H](C)CCC/C(C)=C/Cc1cc(O)ccc1O.[Na+]

Standard InChI:  InChI=1S/C31H48O6S.Na/c1-21(11-13-24-19-25(32)14-15-27(24)33)9-7-10-23(3)28(37-38(34,35)36)20-26-22(2)12-16-29-30(4,5)17-8-18-31(26,29)6;/h11-12,14-15,19,23,26,28-29,32-33H,7-10,13,16-18,20H2,1-6H3,(H,34,35,36);/q;+1/p-1/b21-11+;/t23-,26+,28-,29+,31-;/m1./s1

Standard InChI Key:  MWESFEYZPAHLCJ-NHDYRKAGSA-M

Molfile:  

     RDKit          2D

 40 41  0  0  0  0  0  0  0  0999 V2000
    8.8258    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -1.9871   -1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016   -1.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160   -1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871   -0.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160   -0.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1305   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1305    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6982   -2.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1305   -1.1155    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -0.2905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5852    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2997    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0142    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2997    1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576    0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576   -0.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -0.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5865    0.9470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582   -0.7030    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -1.4175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1457    0.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563   -1.1155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4160    1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
 19 21  1  6
  9 10  2  0
 20 22  1  0
 10 11  1  0
 22 23  1  0
  6  7  1  0
 23 24  1  0
  4 12  1  0
 24 25  2  0
 24 26  1  0
  4 13  1  0
 25 27  1  0
  2  3  1  0
 27 28  1  0
  6 14  1  6
 28 29  2  0
  2  5  1  0
 29 30  1  0
  7 15  1  1
 30 31  2  0
  3  4  1  0
 31 32  1  0
 11 16  1  6
 32 33  2  0
 33 28  1  0
  4  7  1  0
 33 34  1  0
 16 17  1  0
 30 35  1  0
  6  5  1  0
 18 36  1  0
 17 18  1  6
 36 37  1  0
  6 11  1  0
 36 38  2  0
 17 19  1  0
 36 39  2  0
  7  8  1  0
 10 40  1  0
 19 20  1  0
M  CHG  2   1   1  37  -1
M  END

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: 548.79

Molecular Weight (Monoisotopic): 548.3172

AlogP: 7.77

#Rotatable Bonds: 11

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.90

CX Basic pKa: ┄

CX LogP: 8.16

CX LogD: 5.79

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.15

Np Likeness Score: 2.74

References

1. Lee HS, Lee TH, Yang SH, Shin HJ, Shin J, Oh KB..  (2007)  Sesterterpene sulfates as isocitrate lyase inhibitors from tropical sponge Hippospongia sp.,  17  (9): [PMID:17317180] [10.1016/j.bmcl.2007.02.027]

2. Amagata T, Whitman S, Johnson TA, Stessman CC, Loo CP, Lobkovsky E, Clardy J, Crews P, Holman TR..  (2003)  Exploring sponge-derived terpenoids for their potency and selectivity against 12-human, 15-human, and 15-soybean lipoxygenases.,  66  (2): [PMID:12608855] [10.1021/np020462l]

3. Lee D, Shin J, Yoon KM, Kim TI, Lee SH, Lee HS, Oh KB..  (2008)  Inhibition of Candida albicans isocitrate lyase activity by sesterterpene sulfates from the tropical sponge Dysidea sp.,  18  (20): [PMID:18824352] [10.1016/j.bmcl.2008.09.059]

4. Bae J, Jeon JE, Lee YJ, Lee HS, Sim CJ, Oh KB, Shin J..  (2011)  Sesterterpenes from the tropical sponge Coscinoderma sp.,  74  (8): [PMID:21827183] [10.1021/np200492k]

Source

Source(1):

• Scientific Literature