Nanaomycin

Base Information

• Chemical Name: Nanaomycin
• CAS No.: 52934-83-5
• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.284
• NSC Number: 267461
• DSSTox Substance ID: DTXSID70866291
• Wikidata: Q104202286
• Pharos Ligand ID: Z3MUKZ9RX4K5
• ChEMBL ID: CHEMBL1212972
• Mol file: 52934-83-5.mol

Synonyms:NANAOMYCIN;2-(9-Hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl)acetic acid;MLS002702116;Nanomycin A;NSC267461;SMR001565684;C16H14O6;NSC-267461;Neuro_000132;cid_40586;CHEMBL1212972;SCHEMBL18567076;BDBM80078;DTXSID70866291;CHEBI:193279;ZCJHPTKRISJQTN-UHFFFAOYSA-N;1H-Naphtho(2,3-c)pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, (1S-E)-;SMP2_000265;LS-95498;NCI60_002162;BRD-A86160188-001-01-8;2-(9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g][2]benzopyran-3-yl)acetic acid;2-(9-hydroxy-5,10-diketo-1-methyl-3,4-dihydro-1H-benz[g]isochromen-3-yl)acetic acid;(9-Hydroxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-benzo[g]isochromen-3-yl)acetic acid;(9-Hydroxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho[2,3-c]pyran-3-yl)acetic acid;1H-Naphtho(2,3-c)pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-,(1S-E)-;2-[1-methyl-9-oxidanyl-5,10-bis(oxidanylidene)-3,4-dihydro-1H-benzo[g]isochromen-3-yl]ethanoic acid

Chemical Property of Nanaomycin

Chemical Property:

• Vapor Pressure: 2.56E-15mmHg at 25°C
• Melting Point: 179°C
• Refractive Index: 1.4600 (estimate)
• Boiling Point: 601.5°Cat760mmHg
• Flash Point: 229°C
• PSA: 100.90000
• Density: 1.49g/cm³
• LogP: 1.71990
• Storage Temp.: −20°C
• Solubility.: insoluble in H2O; ≥15.1 mg/mL in DMSO; ≥31.07 mg/mL in EtOH with ultrasonic
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 302.07903816
• Heavy Atom Count: 22
• Complexity: 563

Purity/Quality:

99%, ^*data from raw suppliers

NanaomycinA ≥98.0% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 22-24
• Safety Statements: 36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=C(CC(O1)CC(=O)O)C(=O)C3=C(C2=O)C(=CC=C3)O

Technology Process of Nanaomycin

There total 5 articles about Nanaomycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

Kalafungin (29394-61-4,60325-08-8,77448-27-2,11048-15-0) → 4-deoxykalafunginic acid (52934-83-5,73804-47-4,90761-55-0,142292-63-5,98392-26-8)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; for 1h; under 2280 Torr; Ambient temperature;

DOI:10.1246/bcsj.58.1699

Reference yield:

C16H16O5 → 4-deoxykalafunginic acid (52934-83-5,73804-47-4,90761-55-0,142292-63-5,98392-26-8)

Guidance literature:

With ActVA-5 hydroxylase; In methanol; pH=6.5; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/cbic.201900490

Reference yield:

4-dihydro-9-hydroxy-1-methyl-10-oxo-3H-naphtho<2,3-c>pyran-3(S)-acetic acid → 4-deoxykalafunginic acid (52934-83-5,73804-47-4,90761-55-0,142292-63-5,98392-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate

2: ActVA-5 hydroxylase / methanol / pH 6.5 / Enzymatic reaction

With sodium tetrahydroborate; ActVA-5 hydroxylase; In methanol;

DOI:10.1002/cbic.201900490

upstream raw materials:

Kalafungin

6-deoxykalafungin

Refernces

• 1、 Taguchi, Takaaki,Okamoto, Susumu,Hasegawa, Kimiko,Ichinose, Koji. "Epoxyquinone formation catalyzed by a two-component flavin-dependent monooxygenase involved in biosynthesis of the antibiotic actinorhodin". experimental part. p. 2767 - 2773. Retrieved 2012/04/10.
• 2、 Li,Ellison. "Stereoselective total synthesis of racemic kalafungin and nanaomycin A". . p. 6263 - 6265. Retrieved 2007/10/11.