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Paspaline

AlkaPlorer ID: AK048359

Synonym: None

IUPAC Name: 2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

Structure

SMILES: CC(C)(O)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C(NC5=CC=CC=C45)[C@@]23C)O1

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InChI: InChI=1S/C28H39NO2/c1-25(2,30)22-12-14-26(3)21-11-10-17-16-19-18-8-6-7-9-20(18)29-24(19)28(17,5)27(21,4)15-13-23(26)31-22/h6-9,17,21-23,29-30H,10-16H2,1-5H3/t17-,21-,22-,23-,26-,27-,28+/m0/s1

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InChIKey: WLAIEIMDXUAGPY-HSECPPETSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Penicillium paxilli Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 421.62500000000017

TPSA？: 45.25

MolLogP？: 6.132800000000007

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Caenorhabditis elegans Caenorhabditis elegans Activity nan None 10.1039/c3md00198a
Caenorhabditis elegans Calcium-activated potassium channel slo-1 Inhibition nan % 10.1016/j.ejmech.2013.09.045
Homo sapiens A2780 IC50 5300.0 nM 10.1021/acs.jnatprod.8b00723
Homo sapiens HEK293 IC50 43000.0 nM 10.1021/acs.jnatprod.8b00723
Homo sapiens J82 IC50 nan None 10.1021/acs.jnatprod.8b00723
Homo sapiens MCF7 IC50 12800.0 nM 10.1039/c3md00198a
Homo sapiens MDA-MB-231 IC50 7600.0 nM 10.1039/c3md00198a
Homo sapiens MDA-MB-231 IC50 12400.0 nM 10.1039/c3md00198a
Homo sapiens MDA-MB-231 Inhibition nan % 10.1016/j.ejmech.2013.09.045
Influenza A virus (A/Puerto Rico/8/1934(H1N1)) Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 77900.0 nM 10.1021/np400304q
Mus musculus L5178Y IC50 nan None 10.1021/acs.jnatprod.8b00723
None Unchecked Ratio IC50 8.1 None 10.1021/acs.jnatprod.8b00723

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004960 CC(C)(O)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2Cc4c([nH]c5ccccc45)[C@@]23C)O1>>CC(C)(O)[C@@H]1CC[C@]2(C=O)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2Cc4c([nH]c5ccccc45)[C@@]23C)O1 R10371
AKRT004961 CC(C)(O)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2Cc4c([nH]c5ccccc45)[C@@]23C)O1>>CC(C)(O)[C@@H]1C[C@@H](O)[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2Cc4c([nH]c5ccccc45)[C@@]23C)O1 RXN-15735
AKRT004962 CC(C)(O)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2Cc4c([nH]c5ccccc45)[C@@]23C)O1>>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 RXN-15499
AKRT004963 CC(C)(O)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2Cc4c([nH]c5ccccc45)[C@@]23C)O1>>O=CO RXN-15499
AKRT006850 CC1(C)O[C@@H]1CC[C@]1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@H]1Cc3c([nH]c4ccccc34)[C@@]12C>>CC(C)(O)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2Cc4c([nH]c5ccccc45)[C@@]23C)O1 RXN-15498