Daphnetin - ≥90%(HPLC) , CAS No.486-35-1

CAS: 486-35-1 Cat. No.: D155111 Molecular Weight: 178.14 Beilstein Registry Number: 18(5)3,211 EC Number: 207-632-8

GRADE & PURITY ≥90%(HPLC)

Synonyms

Spectrum4_001254 | 7,8-Dihydroxy-2H-1-benzopyran-2-one | XC84571RD2 | KBio1_001904 | ATEFPOUAMCWAQS-UHFFFAOYSA-N | BDBM50206006 | BRD-K61269089-001-02-2 | COUMARIN, 7,8-DIHYDROXY- | 7,8-Dihydroxycoumarin, 90% | AE-641/02519040 | NCGC00093770-02 | NCGC0026

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

Spectrum4_001254 | 7, 8-Dihydroxy-2H-1-benzopyran-2-one | XC84571RD2 | KBio1_001904 | ATEFPOUAMCWAQS-UHFFFAOYSA-N | BDBM50206006 | BRD-K61269089-001-02-2 | COUMARIN, 7, 8-DIHYDROXY- | 7, 8-Dihydroxycoumarin, 90% | AE-641/02519040 | NCGC00093770-02 | NCGC0026

Specifications & Purity

≥90%(HPLC)

Biochemical and Physiological Mechanisms

Daphnetin is an inhibitor of protein kinases. It is an active lactone present in plants such as Daphne Korean Nakai, and Thymelaeaceae Daphne. It serves as as analgesic, antiviral and antibacterial agent. 7, 8-Dihydroxycoumarinan is found to induce tumor a

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥90%(HPLC)

Names and Identifiers

• Pubchem Sid: 504763307
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763307
• Canonical Smiles: C1=CC(=C(C2=C1C=CC(=O)O2)O)O
• IUPAC Name: 7,8-dihydroxychromen-2-one
• InChIKey: ATEFPOUAMCWAQS-UHFFFAOYSA-N
• INCHI: 1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H
• Isomeric SMILES: C1=CC(=C(C2=C1C=CC(=O)O2)O)O
• RTECS: GN6382600
• Molecular Weight: 178.14
• Beilstein: 18(5)3,211
• Reaxy-Rn: 9372
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9372&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Hydroxycoumarins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Hydroxycoumarins
• Intermediate Tree Nodes: Not available
• Direct Parent: 7,8-dihydroxycoumarins
• Alternative Parents: 7-hydroxycoumarins 1-benzopyrans Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Heteroaromatic compounds Lactones Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 7,8-dihydroxycoumarin - 7-hydroxycoumarin - Benzopyran - 1-benzopyran - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Lactone - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 7,8-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively.
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

XDH Tclin Xanthine dehydrogenase (1038 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DAPK3 Tchem Death-associated protein kinase 3 (2108 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPK11 Tchem MAP kinase p38 beta (2785 Activities)

Discover Target: MAPK11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

POLB Tchem DNA polymerase beta (23632 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAP2K6 Tchem Dual specificity mitogen-activated protein kinase kinase 6 (1284 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CSNK1G1 Tchem Casein kinase I gamma 1 (2496 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAMK2B Tchem CaM kinase II beta (1626 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CDK6 Tclin Cyclin-dependent kinase 6 (1724 Activities)

Discover Target: CDK6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHEK2 Tchem Serine/threonine-protein kinase Chk2 (4015 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDPK1 Tchem 3-phosphoinositide dependent protein kinase-1 (3758 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRKAA2 Tchem AMP-activated protein kinase, alpha-2 subunit (1328 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PIM1 Tchem Serine/threonine-protein kinase PIM1 (9629 Activities)

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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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JAK1 Tclin Tyrosine-protein kinase JAK1 (8569 Activities)

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ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAMK4 Tbio CaM kinase IV (2116 Activities)

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MAP2K2 Tclin Dual specificity mitogen-activated protein kinase kinase 2 (1262 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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SLC2A1 Tchem Glucose transporter (14755 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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CAMK2D Tchem CaM kinase II delta (2813 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CSNK1G2 Tchem Casein kinase I gamma 2 (2539 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPK3 Tchem MAP kinase ERK1 (4725 Activities)

Discover Target: MAPK3

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CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

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PRKACA Tchem cAMP-dependent protein kinase alpha-catalytic subunit (3475 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAMK2A Tchem CaM kinase II alpha (1938 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RPS6KA3 Tchem Ribosomal protein S6 kinase alpha 3 (4284 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PLK4 Tchem Serine/threonine-protein kinase PLK4 (1882 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

STK16 Tchem Serine/threonine-protein kinase 16 (910 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

STK10 Tchem Serine/threonine-protein kinase 10 (2119 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CLK1 Tchem Dual specificty protein kinase CLK1 (2189 Activities)

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CLK2 Tchem Dual specificity protein kinase CLK2 (3942 Activities)

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CLK3 Tchem Dual specificity protein kinase CLK3 (2711 Activities)

Discover Target: CLK3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NEK2 Tchem Serine/threonine-protein kinase NEK2 (3514 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CDK16 Tchem Serine/threonine-protein kinase PCTAIRE-1 (829 Activities)

Discover Target: CDK16

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

STK4 Tchem Serine/threonine-protein kinase MST1 (2643 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAMK1D Tchem CaM kinase I delta (2141 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAMK1G Tchem CaM kinase I gamma (570 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Camk2g CaM kinase II gamma (1 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Enterococcus faecalis (29875 Activities)

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Plasmodium falciparum (966862 Activities)

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Influenza A virus (11224 Activities)

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ht1 Hexose transporter 1 (14071 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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PYK Pyruvate kinase (6726 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Vibrio harveyi (399 Activities)

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luxP Autoinducer 2-binding periplasmic protein luxP (60 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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nfo Endonuclease 4 (425 Activities)

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Phosphoglycerate kinase, glycosomal (2184 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 150 mg/mL (842.03 mM; Need ultrasonic and warming)
• Melt Point(°C): 256°C
• Molecular Weight: 178.140 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 178.027 Da
• Monoisotopic Mass: 178.027 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 248.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yongkui Wang, Jian Chen, Jing Chen, Chao Dong, Xu Yan, Zhongpei Zhu, Pan Lu, Zongmian Song, Hongjian Liu, Songfeng Chen.  (2020)  Daphnetin ameliorates glucocorticoid-induced osteoporosis via activation of Wnt/GSK-3β/β-catenin signaling.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:33171191] [10.1016/j.taap.2020.115333]