[(1R,2S,8R,9S,10S,12R,13S,14S,17S,19R,20S,21R)-5-[(acetyloxy)methyl]-9,21-dihydroxy-23-(1-methoxy-1-oxopropan-2-ylidene)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0^{2,6}.0^{2,14}.0^{8,13}.0^{10,12}.0^{17,19}.0^{20,24}]tetracosa-5,16(24)-dien-9-yl]methyl (2E)-2-methylbut-2-enoate

ID: ALA2229596

Cas Number: 943136-39-8

PubChem CID: 44207635

Max Phase: Preclinical

Molecular Formula: C38H44O11

Molecular Weight: 676.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(\C)C(=O)OC[C@]1(O)[C@H]2C[C@H]2[C@]2(C)[C@@H]3CC4=C5[C@H](/C(=C(/C)C(=O)OC)C(=O)[C@H](O)[C@@]5(C)[C@@H]5C[C@H]45)[C@@]34OC(=O)C(COC(C)=O)=C4C[C@@H]12

Standard InChI:  InChI=1S/C38H44O11/c1-8-15(2)32(42)48-14-37(45)24-11-23(24)35(5)25(37)12-22-20(13-47-17(4)39)34(44)49-38(22)26(35)10-19-18-9-21(18)36(6)28(19)29(38)27(30(40)31(36)41)16(3)33(43)46-7/h8,18,21,23-26,29,31,41,45H,9-14H2,1-7H3/b15-8+,27-16-/t18-,21-,23-,24+,25-,26+,29+,31+,35+,36+,37+,38+/m1/s1

Standard InChI Key:  WZKZSZYDBUUHLB-IBBKUXAASA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2229596

   Chlorahololide D

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: 676.76

Molecular Weight (Monoisotopic): 676.2884

AlogP: 3.08

#Rotatable Bonds: 6

Polar Surface Area: 162.73

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.79

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: ┄

Heavy Atoms: 49

QED Weighted: 0.18

Np Likeness Score: 3.00

References

1. Lee YM, Moon JS, Yun BS, Park KD, Choi GJ, Kim JC, Lee SH, Kim SU..  (2009)  Antifungal activity of CHE-23C, a dimeric sesquiterpene from Chloranthus henryi.,  57  (13): [PMID:19566082] [10.1021/jf900674y]

2. Zhou B, Wu Y, Dalal S, Merino EF, Liu QF, Xu CH, Yuan T, Ding J, Kingston DG, Cassera MB, Yue JM..  (2017)  Nanomolar Antimalarial Agents against Chloroquine-Resistant Plasmodium falciparum from Medicinal Plants and Their Structure-Activity Relationships.,  80  (1): [PMID:27997206] [10.1021/acs.jnatprod.6b00744]

3. Bai B, Ye SX, Yang DP, Zhu LP, Tang GH, Chen YY, Li GQ, Zhao ZM..  (2019)  Chloraserrtone A, a Sesquiterpenoid Dimer from Chloranthus serratus.,  82  (2): [PMID:30724564] [10.1021/acs.jnatprod.8b00418]

Source

Source(1):

• Scientific Literature