6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalenecarboxylic Acid
PubChem CID
135411
Structure
Chemical Safety
Molecular Formula
Synonyms
- 125316-60-1
- CD437
- AHPN
- Cd 437
- O-Desmethyl Adapalene
Molecular Weight
398.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-08-08
- Modify:2025-01-18
Description
CD437 is a naphthoic acid that is 6-phenylnaphthylene-2-carboxyic acid in which the phenyl substituent has been substituted at positions 3 and 4 by adamant-1-yl and hydroxy groups, respectively. It acts as a selective agonist of retinoic acid receptor (RAR)gamma and induces cell cycle arrest and apoptosis in various cancer cells. It has a role as an apoptosis inducer and a retinoic acid receptor gamma agonist. It is a member of adamantanes, a monocarboxylic acid, a naphthoic acid and a member of phenols.
Chemical Structure Depiction
6-[3-(1-adamantyl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C27H26O3/c28-25-6-5-22(20-1-2-21-11-23(26(29)30)4-3-19(21)10-20)12-24(25)27-13-16-7-17(14-27)9-18(8-16)15-27/h1-6,10-12,16-18,28H,7-9,13-15H2,(H,29,30)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
LDGIHZJOIQSHPB-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C1C2CC3CC1CC(C2)(C3)C4=C(C=CC(=C4)C5=CC6=C(C=C5)C=C(C=C6)C(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C27H26O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 6-(3-(1-adamantyl)-4-hydroxyphenyl)-2-naphthalenecarboxylic acid
- AHPN
- CD 437
- CD-437
- CD437 cpd
- Ro 47-2077
- Ro-47-2077
- 125316-60-1
- CD437
- AHPN
- Cd 437
- O-Desmethyl Adapalene
- CD-437
- 6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalenecarboxylic Acid
- 6-[3-(1-adamantyl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid
- MFCD03106506
- 6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid
- CHEMBL1180
- CHEBI:88334
- 2-Naphthalenecarboxylic acid, 6-(4-hydroxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-
- 6-(3-(adamantan-1-yl)-4-hydroxyphenyl)-2-naphthoic acid
- 6-[3-(1-adamantyl)-4-oxidanyl-phenyl]naphthalene-2-carboxylic acid
- Apoptosis Activator VI
- Ro 47-2077
- 6-(4-Hydroxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic Acid
- 6-(4-Hydroxy-3-tricyclo(3.3.1.1(3,7))dec-1-ylphenyl)-2-naphthalenecarboxylic acid
- MLS006010698
- SCHEMBL174205
- GTPL3431
- 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthoic acid
- DTXSID80154737
- BCPP000296
- HMS3268E03
- HMS3412J15
- HMS3676J15
- HMS3867G03
- BCP23360
- EX-A1814
- BDBM50048291
- CD437?
- AKOS024456659
- BCP9000499
- 2-Naphthalenecarboxylic acid, 6-(4-hydroxy-3-tricyclo(3.3.1.1(3,7))dec-1-ylphenyl)-
- CD437, >=98% (HPLC), solid
- NCGC00092284-01
- NCGC00092284-02
- NCGC00092284-03
- AC-35510
- AS-73811
- DA-72028
- PD119178
- SMR004701675
- SY274312
- BCP0726000216
- HY-100532
- CS-0019677
- D83837
- J-005212
- BRD-K28907958-001-01-9
- BRD-K28907958-001-04-3
- Q27074360
- Z2216887943
- 6-[3''-(1-adamantyl)-4''-hydroxyphenyl]-2-naphthoic acid
- 6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid
- 6-[3-(1-adamantyl)-4-hydroxy-phenyl]naphthalene-2-carboxylic acid
- 6-(3-((3r,5r,7r)-Adamantan-1-yl)-4-hydroxyphenyl)-2-naphthoic acid
- 6-(3-Adamantan-1-yl-4-hydroxy-phenyl)-naphthalene-2-carboxylic acid
- 6-[3''-(1-adamantyl)-4''-hydroxyphenyl]-2-naphthalenecarboxylic acid
- 6-[3-(ADAMANTAN-1-YL)-4-HYDROXYPHENYL]NAPHTHALENE-2-CARBOXYLIC ACID
- 6-[4-hydroxy-3-(tricyclo[3.3.1.1(3,7)]dec-1-yl)phenyl]-2-naphthalenecarboxylic acid
- 6-[4-hydroxy-3-(tricyclo[3.3.1.1(3,7)]dec-1-yl)phenyl]naphthalene-2-carboxylic acid
- E9T
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
398.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
7.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
398.18819469 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
398.18819469 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
57.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
630
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Antineoplastic Agents
Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)
Pictogram(s)
Signal
Warning
GHS Hazard Statements
H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
Precautionary Statement Codes
P203, P280, P318, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)
ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Repr. 2 (100%)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=LDGIHZJOIQSHPB-UHFFFAOYSA-N
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- European Chemicals Agency (ECHA)LICENSEUse of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.https://echa.europa.eu/web/guest/legal-notice6-(4-Hydroxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acidhttps://echa.europa.eu/substance-information/-/substanceinfo/100.220.4706-(4-Hydroxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid (EC: 692-455-2)https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/226217
- ChEBI
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- Comparative Toxicogenomics Database (CTD)LICENSEIt is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.http://ctdbase.org/about/legal.jsp
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)https://www.guidetopharmacology.org/about.jsp#licenseGuide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Therapeutic Target Database (TTD)PMID27336223-Compound-12https://idrblab.net/ttd/data/drug/details/D09YFJ
- Human Metabolome Database (HMDB)LICENSEHMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.http://www.hmdb.ca/citing6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalenecarboxylic Acidhttp://www.hmdb.ca/metabolites/HMDB0244485
- Japan Chemical Substance Dictionary (Nikkaji)
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/about
- Protein Data Bank in Europe (PDBe)
- Springer Nature
- Wikidata
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlAntineoplastic Agentshttps://www.ncbi.nlm.nih.gov/mesh/68000970
- GHS Classification (UNECE)GHS Classification Treehttp://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 388642134https://pubchem.ncbi.nlm.nih.gov/substance/388642134
- NCBI
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