SCS-C002853

(4R,8R,10S,18R,19R)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,11,14-tetraene-6,16-dione

Pathway: Alkaloids Superclass: Nicotinic acid alkaloids Class: Pyridine alkaloids

Chemical Structure

Structure of (4R,8R,10S,18R,19R)-18-(furan-3-yl)-10-hydroxy-4,9,9,19-tetramethyl-5,17-dioxa-2-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,11,14-tetraene-6,16-dione

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Source Information

Xylocarpus granatum (Mangrove)

Kingdom Viridiplantae Phylum Streptophyta Class Magnoliopsida Order Sapindales Family Meliaceae Genus Xylocarpus Species Xylocarpus granatum

Hainan Island

DOI: 10.1002/mrc.2273 · Magnetic Resonance in Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

449.5 Da

Threshold ≤ 500

ALogP

4.16

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H27NO6

Molecular Weight:

449.5030 Da

SMILES:

CC1(C)[C@H](O)c2cc3c(nc2[C@]2(C)OC(=O)C[C@H]12)CC[C@]1(C)C3=CC(=O)O[C@H]1c1ccoc1

InChIKey:

                        XKLARMZOADMPPA-BXFPRZKISA-N
                        
                    

InChI:

InChI=1S/C26H27NO6/c1-24(2)18-11-20(29)33-26(18,4)21-15(22(24)30)9-14-16-10-19(28)32-23(13-6-8-31-12-13)25(16,3)7-5-17(14)27-21/h6,8-10,12,18,22-23,30H,5,7,11H2,1-4H3/t18-,22-,23+,25-,26-/m1/s1

Calculated Properties

ALogP:

4.160 lipophilicity

TPSA:

98.86 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.5000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C002853

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Nicotinic acid alkaloids

NPClassifier Class:

Pyridine alkaloids

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD18546

Biological Activity Data

No bioactivity data available for this compound.

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