ID: ALA572366

Max Phase: Preclinical

Molecular Formula: C15H18O4

Molecular Weight: 262.31

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc2oc(=O)ccc2cc1[C@@H](O)CC(C)C

Standard InChI:  InChI=1S/C15H18O4/c1-9(2)6-12(16)11-7-10-4-5-15(17)19-13(10)8-14(11)18-3/h4-5,7-9,12,16H,6H2,1-3H3/t12-/m0/s1

Standard InChI Key:  ZRXJDVGAMZQYJX-LBPRGKRZSA-N

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

Properties

Molecular Weight: 262.31

Molecular Weight (Monoisotopic): 262.1205

AlogP: 2.88

#Rotatable Bonds: 4

Polar Surface Area: 59.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.86

Np Likeness Score: 0.68

References

1. Temperini C, Innocenti A, Scozzafava A, Parkkila S, Supuran CT..  (2010)  The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors.,  53  (2): [PMID:20028100] [10.1021/jm901524f]

2. Maresca A, Temperini C, Pochet L, Masereel B, Scozzafava A, Supuran CT..  (2010)  Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins.,  53  (1): [PMID:19911821] [10.1021/jm901287j]

3. Maresca A, Supuran CT..  (2010)  Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II.,  20  (15): [PMID:20580555] [10.1016/j.bmcl.2010.06.040]

4. Maresca A, Scozzafava A, Supuran CT..  (2010)  7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range.,  20  (24): [PMID:21067924] [10.1016/j.bmcl.2010.10.094]

5. Tars K, Vullo D, Kazaks A, Leitans J, Lends A, Grandane A, Zalubovskis R, Scozzafava A, Supuran CT..  (2013)  Sulfocoumarins (1,2-benzoxathiine-2,2-dioxides): a class of potent and isoform-selective inhibitors of tumor-associated carbonic anhydrases.,  56  (1): [PMID:23241068] [10.1021/jm301625s]

Source

Source(1):

• Scientific Literature