(+)-Eremantholide C

ID: ALA4476344

PubChem CID: 22525107

Max Phase: Preclinical

Molecular Formula: C19H22O6

Molecular Weight: 346.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@]1(O)O[C@H]2C[C@@]3(C)OC(=CC3=O)/C(C)=C\[C@H]3OC(=O)[C@@]1(C)[C@@H]23

Standard InChI:  InChI=1S/C19H22O6/c1-9(2)19(22)18(5)15-12(23-16(18)21)6-10(3)11-7-14(20)17(4,24-11)8-13(15)25-19/h6-7,12-13,15,22H,1,8H2,2-5H3/b10-6-/t12-,13+,15-,17-,18-,19-/m1/s1

Standard InChI Key:  YEIAHHGCPUIGOQ-VMAJNZJNSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   18.1557  -22.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9053  -21.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7512  -21.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5010  -21.8504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1350  -19.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1805  -20.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1805  -19.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2011  -19.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8599  -18.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6055  -18.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7966  -18.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5464  -18.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4718  -19.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5548  -18.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0815  -17.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1557  -23.1331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9423  -21.0778    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.1368  -20.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5601  -21.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7362  -21.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8604  -20.8739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1516  -21.7794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8986  -22.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5412  -21.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7282  -22.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9464  -22.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9450  -20.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8313  -20.0955    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  2 19  1  0
  1  2  1  0
 19  3  1  0
  4  1  1  0
  5 18  1  0
  3  6  1  0
  6  7  2  0
 11 12  2  0
  9 10  1  0
  8  9  1  0
 10 11  1  0
 12  8  1  0
  7 12  1  0
  5  9  1  0
  7 13  1  0
  9 14  1  6
 10 15  2  0
  1 16  2  0
  3 17  1  1
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 18  1  0
 19 22  1  1
  2 23  1  6
 20 24  1  0
 20 25  1  1
 24 26  2  0
 24 27  1  0
 18 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4476344

   (1S,3R,7Z,9R,12S,13R,15S)-13-hydroxy-3,7,12-trimethyl-13-prop-1-en-2-yl-10,14,16-trioxatetracyclo[7.5.1.13,6.012,15]hexadeca-5,7-diene-4,11-dione

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 346.38

Molecular Weight (Monoisotopic): 346.1416

AlogP: 1.79

#Rotatable Bonds: 1

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.91

CX Basic pKa: ┄

CX LogP: 2.00

CX LogD: 2.00

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: 2.82

References

1. Ren Y, de Blanco EJC, Fuchs JR, Soejarto DD, Burdette JE, Swanson SM, Kinghorn AD..  (2019)  Potential Anticancer Agents Characterized from Selected Tropical Plants.,  82  (3): [PMID:30830783] [10.1021/acs.jnatprod.9b00018]

Source

Source(1):

• Scientific Literature