Scapanacin B; 15-ethyoxy-cis-cleroda-1,3,13-trien-18-acid-16,15-olide

ID: ALA4246780

PubChem CID: 145985782

Max Phase: Preclinical

Molecular Formula: C22H30O5

Molecular Weight: 374.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC1C=C(CC[C@]2(C)[C@@H](C)CC[C@@]3(C)C(C(=O)O)=CC=C[C@@H]23)C(=O)O1

Standard InChI:  InChI=1S/C22H30O5/c1-5-26-18-13-15(20(25)27-18)10-12-21(3)14(2)9-11-22(4)16(19(23)24)7-6-8-17(21)22/h6-8,13-14,17-18H,5,9-12H2,1-4H3,(H,23,24)/t14-,17-,18?,21+,22-/m0/s1

Standard InChI Key:  WDAFREQBUZXZAG-KPUPJOIGSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   10.6675   -6.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6663   -7.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3744   -7.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3726   -5.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0812   -6.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0800   -7.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7862   -7.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4981   -7.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4993   -6.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7886   -5.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0763   -5.5181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0721   -7.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3760   -8.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6692   -8.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0846   -8.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7886   -5.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4963   -4.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4963   -3.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4919   -5.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2080   -5.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1588   -3.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9063   -2.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0890   -2.6261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8366   -3.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3866   -1.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1993   -2.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6797   -1.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0596   -3.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  6
  6 12  1  6
  3 13  1  0
 13 14  1  0
 13 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 10 19  1  1
  9 20  1  1
 18 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 18  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 24 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4246780

   ---

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: 374.48

Molecular Weight (Monoisotopic): 374.2093

AlogP: 4.25

#Rotatable Bonds: 6

Polar Surface Area: 72.83

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.34

CX Basic pKa: ┄

CX LogP: 4.66

CX LogD: 1.72

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: 2.82

References

1. Qiao Y, Zheng H, Li L, Zhang J, Li Y, Li S, Zhu R, Zhou J, Zhao S, Jiang Y, Lou H..  (2018)  Terpenoids with vasorelaxant effects from the Chinese liverwort Scapania carinthiaca.,  26  (14): [PMID:30049584] [10.1016/j.bmc.2018.07.035]

Source

Source(1):

• Scientific Literature