3-(2-((1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decahydronaphthalen-1-yl)vinyl)-5-(propan-2-ylidene)furan-2(5H)-one

ID: ALA205812

PubChem CID: 637300

Max Phase: Preclinical

Molecular Formula: C23H32O4

Molecular Weight: 372.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1/C=C/C1=CC(=C(C)C)OC1=O

Standard InChI:  InChI=1S/C23H32O4/c1-14(2)18-12-16(21(26)27-18)7-8-17-15(3)6-9-19-22(17,4)11-10-20(25)23(19,5)13-24/h7-8,12,17,19-20,24-25H,3,6,9-11,13H2,1-2,4-5H3/b8-7+/t17-,19+,20-,22+,23+/m1/s1

Standard InChI Key:  NOBUCQWGEOIPGK-ZCDHJCLFSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  1  0  0  0  0  0999 V2000
   -4.1417  -19.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1417  -20.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296  -21.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296  -19.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176  -19.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166  -20.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0055  -21.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910  -20.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920  -19.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076  -19.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0098  -18.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2965  -18.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987  -17.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332  -17.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902  -16.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152  -16.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680  -17.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1520  -17.2716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7250  -19.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8555  -21.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375  -22.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1500  -21.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5777  -19.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1559  -22.4473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020  -15.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685  -14.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0222  -15.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177  -21.8083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  2  0
  5 10  1  0
 14 18  2  0
  6  7  1  0
  5 19  1  6
  7  8  1  0
  2 20  1  6
  8  9  1  0
  9 10  1  0
  3 21  1  0
  5  6  1  0
  3 22  1  1
 10 11  1  6
  9 23  2  0
 21 24  1  0
 11 12  2  0
 16 25  2  0
  1  2  1  0
 25 26  1  0
 12 13  1  0
 25 27  1  0
  6 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA205812

   14-Deoxy-15-isopropylidene-11,12-didehydroandrographolide

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: 372.51

Molecular Weight (Monoisotopic): 372.2301

AlogP: 4.06

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 3.26

References

1. Dai GF, Xu HW, Wang JF, Liu FW, Liu HM..  (2006)  Studies on the novel alpha-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues.,  16  (10): [PMID:16504503] [10.1016/j.bmcl.2006.02.011]

2. Xu HW, Dai GF, Liu GZ, Wang JF, Liu HM..  (2007)  Synthesis of andrographolide derivatives: a new family of alpha-glucosidase inhibitors.,  15  (12): [PMID:17428667] [10.1016/j.bmc.2007.03.063]

Source

Source(1):

• Scientific Literature