Aeroplysinin
Basic information
- CAS
28656-91-9- Standard SMILES
COC1=C(Br)[C@H](O)[C@](O)(CC#N)C=C1Br- InChIKey
BGYNLOSBKBOJJD-IUCAKERBSA-N- Molecular formula
- C9H9Br2NO3
- Average molar mass
- 338.98 g/mol
- Monoisotopic mass
- 336.89492
Overview
Aeroplysinin 1 is a tertiary alcohol.
Names & identifiers
- Preferred name
- Aeroplysinin
- IUPAC
- 2-[(1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile
- English name
- (+)-AEROPLYSININ-1
- Molecular formula
- C9H9Br2NO3
- Molecular weight
- 338.98
Names & synonyms
28656-91-9aeroplysininRefChem:9152073,5-Dibromo-1,5-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonitrileAeroplysinin 1Aeroplysinin I(+)-Aeroplysinin-12-[(1S,6R)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile55057-73-32-((1S,6R)-3,5-Dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile(+)-Aeroplysinin IAEROPLYSININ-I (RACEMIC)
Show more names
aeroplysinini(+)-aeroplysinini(+)--Aeroplysinin-1(+)shy-Aeroplysinin-1Aeroplysinin (Aeroplysinin-1)AEROPLYSININ, APLYSINA AEROPHOBA(+)-AEROPLYSININ-1, APLYSINA AEROPHOBA
DTXSID609513222,6-XylyllithiumNSC-170364Aeroplysinin I, (+)-(.+-.)-Aeroplysinin ICHEMBL462153orb1741526SCHEMBL14267425
Database identifiers
- CAS
28656-91-9、55057-73-3- PubChem CID
- 100308
- DTXSID
DTXSID60951322- ChEMBL
CHEMBL462153- ChEBI
CHEBI:80925- Nikkaji
- J17.043G
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 73.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 382
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Boiling point
- 479.6 · 479.6±45.0 °C(Predicted)
- Density
- 2.01 · 2.01±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Methanol: Soluble
- form
- A solid
- pka
- 10.54 · 10.54±0.70(Predicted)
- color
- Colorless to off-white
- HS Code
- 2941900000 · 2941900000
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- hs_code
- 2941900000
Chemistry & industry
Applications
Description(+)-Aeroplysinin-1 is a metabolite originally isolated from the marine sponge V. aerophoba with diverse biological activities. (+)-Aeroplysinin-1 (0.25-0.5 μM) induces cell death in MCF-7 and ZR-75-1 human breast cancer cells in a time- and concentration-dependent manner but has no effect on normal human fibroblasts at concentrations up to 5 μM. It also blocks EGF-induced endocytosis of the EGF receptor (EGFR) and EGF-dependent cell proliferation in MCF-7 cells. (+)-Aeroplysinin-1 inhibits bovine aortic endothelial (BAE) cell proliferation and cord formation in a Matrigel™ assay. It inhibits angiogenesis in a dose-dependent manner in a chick chorioallantoic membrane (CAM) assay when administered from 1.5 to 3 nmol per egg. (+)-Aeroplysinin-1 also has antibacterial activity against Gram-positive bacteria, including S. aureus, S. albus, and B. subtilis, but not Gram-negative bacteria and inhibits HIV-1 replication (IC50 = 14.6 μM) via inhibition of HIV-1 reverse transcriptase.
Uses(+)shy-Aeroplysinin-1 is a compound that is an inhibitor of EGFR kinase.
Additional notes
DefinitionChEBI: Aeroplysinin 1 is a tertiary alcohol.
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