Ianthellamide A

ID: ALA2022536

PubChem CID: 66561477

Max Phase: Preclinical

Molecular Formula: C13H18Br2N2O6S

Molecular Weight: 490.17

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ianthellamide A | (R)-4-(1-(3-acetamidopropoxy)-2-aminoethyl)-2,6-dibromophenyl hydrogen sulfate|CHEMBL2022536|BDBM50382289

Canonical SMILES:  CC(=O)NCCCO[C@@H](CN)c1cc(Br)c(OS(=O)(=O)O)c(Br)c1

Standard InChI:  InChI=1S/C13H18Br2N2O6S/c1-8(18)17-3-2-4-22-12(7-16)9-5-10(14)13(11(15)6-9)23-24(19,20)21/h5-6,12H,2-4,7,16H2,1H3,(H,17,18)(H,19,20,21)/t12-/m0/s1

Standard InChI Key:  LUKTVGRPGJKVIG-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    1.5986  -14.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5974  -15.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3122  -15.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287  -15.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0258  -14.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3104  -13.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120  -16.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438  -15.4466    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8826  -15.4476    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0264  -16.6862    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262  -17.5112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7410  -16.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375  -17.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080  -12.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212  -12.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923  -12.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8790  -12.9748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369  -12.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4501  -12.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1658  -12.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8791  -12.5474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5948  -12.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5972  -13.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3080  -12.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 12  2  0
  6  1  1  0
 10 13  2  0
  1  2  2  0
  6 14  1  0
  3  7  1  0
 14 15  1  6
  3  4  2  0
 14 16  1  0
  4  8  1  0
 16 17  1  0
 15 18  1  0
  2  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  7 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
  5  6  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2022536

   IANTHELLAMIDE A

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: 490.17

Molecular Weight (Monoisotopic): 487.9252

AlogP: 1.94

#Rotatable Bonds: 9

Polar Surface Area: 127.95

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -2.69

CX Basic pKa: 8.99

CX LogP: -0.06

CX LogD: -0.07

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.36

Np Likeness Score: 0.27

References

1. Feng Y, Bowden BF, Kapoor V..  (2012)  Ianthellamide A, a selective kynurenine-3-hydroxylase inhibitor from the Australian marine sponge Ianthella quadrangulata.,  22  (10): [PMID:22525315] [10.1016/j.bmcl.2012.04.002]

Source

Source(1):

• Scientific Literature