Mailiohydrin

ID: ALA459613

PubChem CID: 10917718

Max Phase: Preclinical

Molecular Formula: C15H21Br3O2

Molecular Weight: 473.04

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Mailiohydrin | Mailiohydrin|CHEMBL459613

Canonical SMILES:  C=C1C[C@@H](O)[C@@H](Br)C(C)(C)[C@@]12C=C[C@@](O)(C(Br)Br)CC2

Standard InChI:  InChI=1S/C15H21Br3O2/c1-9-8-10(19)11(16)13(2,3)14(9)4-6-15(20,7-5-14)12(17)18/h4,6,10-12,19-20H,1,5,7-8H2,2-3H3/t10-,11-,14-,15+/m1/s1

Standard InChI Key:  BDUUDTPDYKKJPZ-FKGLVLAHSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    0.1667   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1625   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8710   -1.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881   -1.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923   -0.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8793   -0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421   -1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1699    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421    0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863    0.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9698    0.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680   -1.1510    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9625   -1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -2.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9712   -1.9288    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5906   -0.5515    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  7 11  1  0
  8  9  1  0
  9  1  1  0
  1 10  1  0
 10 11  1  0
  4  5  1  0
 10 12  2  0
  5  6  2  0
  7 13  1  6
  7  8  1  0
  8 14  1  6
  9 15  1  0
  1  2  1  0
  9 16  1  0
  1  6  1  6
  4 17  1  6
  2  3  1  0
  4 18  1  0
  3  4  1  0
 18 19  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA459613

   MAILIOHYDRIN

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: 473.04

Molecular Weight (Monoisotopic): 469.9092

AlogP: 4.28

#Rotatable Bonds: 1

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.89

CX Basic pKa: ┄

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.44

Np Likeness Score: 3.11

References

1. Francisco ME, Erickson KL..  (2001)  Ma'iliohydrin, a cytotoxic chamigrene dibromohydrin from a Philippine Laurencia species.,  64  (6): [PMID:11421745] [10.1021/np0005053]

2. Chen JY, Huang CY, Lin YS, Hwang TL, Wang WL, Chiou SF, Sheu JH..  (2016)  Halogenated Sesquiterpenoids from the Red Alga Laurencia tristicha Collected in Taiwan.,  79  (9): [PMID:27536968] [10.1021/acs.jnatprod.6b00452]

Source

Source(1):

• Scientific Literature