(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 methyl ester

ID: ALA370543

PubChem CID: 5478977

Max Phase: Preclinical

Molecular Formula: C28H36N2O6

Molecular Weight: 496.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=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/C28H36N2O6/c1-17(2)20-9-7-18(3)21-14-24(35-25(31)10-8-19-15-30(5)16-29-19)27(4)11-12-28(33,36-27)23(13-22(20)21)26(32)34-6/h7-8,10-13,15-17,20-22,24,33H,9,14H2,1-6H3/b10-8+,23-13-/t20-,21+,22-,24+,27+,28-/m1/s1

Standard InChI Key:  VHZOZCRALQEBDG-BEMXCNERSA-N

Molfile:  

     RDKit          2D

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   11.6622   -1.5527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4314    0.5228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   16.5111   -1.0229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA370543

   SARCODICTYIN A

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: 496.60

Molecular Weight (Monoisotopic): 496.2573

AlogP: 3.74

#Rotatable Bonds: 5

Polar Surface Area: 99.88

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.80

CX Basic pKa: 5.70

CX LogP: 4.68

CX LogD: 4.67

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.38

Np Likeness Score: 2.41

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