(E)-(1R,4S,5R,9R,11S,12S)-1-Hydroxy-5-isopropyl-8,12-dimethyl-11-[(E)-3-(1-methyl-1H-imidazol-4-yl)-acryloyloxy]-15-oxa-tricyclo[10.2.1.0*4,9*]pentadeca-2,7,13-triene-2-carboxylic acid ethyl ester

ID: ALA363206

PubChem CID: 9849226

Max Phase: Preclinical

Molecular Formula: C29H38N2O6

Molecular Weight: 510.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C1=C/[C@@H]2[C@@H](C(C)C)CC=C(C)[C@@H]2C[C@H](OC(=O)/C=C/c2cn(C)cn2)[C@]2(C)C=C[C@@]1(O)O2

Standard InChI:  InChI=1S/C29H38N2O6/c1-7-35-27(33)24-14-23-21(18(2)3)10-8-19(4)22(23)15-25(28(5)12-13-29(24,34)37-28)36-26(32)11-9-20-16-31(6)17-30-20/h8-9,11-14,16-18,21-23,25,34H,7,10,15H2,1-6H3/b11-9+,24-14-/t21-,22+,23-,25+,28+,29-/m1/s1

Standard InChI Key:  XFSBPGXNEHXNEG-RZQXXOGCSA-N

Molfile:  

     RDKit          2D

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  8  9  2  0
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  6 20  1  1
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 16 18  1  0
 38 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA363206

   SARCODICTYIN B

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: 510.63

Molecular Weight (Monoisotopic): 510.2730

AlogP: 4.13

#Rotatable Bonds: 6

Polar Surface Area: 99.88

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.80

CX Basic pKa: 5.70

CX LogP: 5.04

CX LogD: 5.03

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.35

Np Likeness Score: 2.26

References

1. Nicolaou KC..  (2005)  Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry.,  48  (18): [PMID:16134928] [10.1021/jm050524f]

2. Nicolaou KC..  (2005)  Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry.,  48  (18): [PMID:16134928] [10.1021/jm050524f]

3. Nakao Y, Yoshida S, Matsunaga S, Fusetani N..  (2003)  (Z)-sarcodictyin A, a new highly cytotoxic diterpenoid from the soft coral Bellonella albiflora.,  66  (4): [PMID:12713406] [10.1021/np0205452]

Source

Source(1):

• Scientific Literature