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Dehydroxypaxilline

AlkaPlorer ID: AK036825

Synonym: None

IUPAC Name: (1S,2S,5S,7R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one

Structure

SMILES: CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@H](CC[C@H]4CC5=C(NC6=CC=CC=C56)[C@@]43C)C2=CC1=O

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InChI: InChI=1S/C27H33NO3/c1-25(2,30)24-21(29)14-18-19-10-9-15-13-17-16-7-5-6-8-20(16)28-23(17)27(15,4)26(19,3)12-11-22(18)31-24/h5-8,14-15,19,22,24,28,30H,9-13H2,1-4H3/t15-,19-,22-,24-,26-,27+/m0/s1

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InChIKey: GYSZYWSJZCKCBD-LXGUAGHKSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Aspergillus striatus Aspergillus Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 419.5650000000001

TPSA？: 62.32

MolLogP？: 4.8418000000000045

Number of H-Donors: 2

Number of H-Acceptors: 3

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens A2780 IC50 17100.0 nM 10.1021/acs.jnatprod.8b00723
Homo sapiens HEK293 IC50 nan None 10.1021/acs.jnatprod.8b00723
Homo sapiens J82 IC50 nan None 10.1021/acs.jnatprod.8b00723
Influenza A virus (A/Puerto Rico/8/1934(H1N1)) Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 150000.0 nM 10.1021/np400304q
Mus musculus L5178Y IC50 nan None 10.1021/acs.jnatprod.8b00723

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004976 CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@H](CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O>>CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O RXN-15501
AKRT004977 CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@H](CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O>>CC1(C)O[C@@]23CC[C@@]4(C)[C@@H](CC[C@H]5Cc6c([nH]c7ccccc67)[C@@]54C)C2=CC(=O)[C@@H]1O3 RXN-15737
AKRT004978 CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@H](CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=C[C@H]1O>>CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@H](CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O RXN-15500