Angelicin - Moligand™,10mM in DMSO , CAS No.523-50-2

CAS: 523-50-2 Cat. No.: A424489 Molecular Weight: 186.16 EC Number: 637-055-0

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

4-Hydroxy-5-benzofuranacrylic acid gamma-lactone | A829042 | 2-Propenoic acid, 3-(4-hydroxy-5-benzofuranyl)-, delta-lactone | Furo[5',8]coumarin | Angelicin, analytical standard | 2H-Furo(2,3-H)-1-benzopyran-2-one | Angelicin plus ultraviolet A radiation

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

An angular furocoumarin, may be used as a photoactivatable molecule that reacts with DNA and unsaturated fatty acids to form monoadducts. Angelicin may be studied as a potential phototherapeutic and to understand its mechanisms of action and effects on RNA and DNA synthesis.

Specifications

Synonyms

4-Hydroxy-5-benzofuranacrylic acid gamma-lactone | A829042 | 2-Propenoic acid, 3-(4-hydroxy-5-benzofuranyl)-, delta-lactone | Furo[5', 8]coumarin | Angelicin, analytical standard | 2H-Furo(2, 3-H)-1-benzopyran-2-one | Angelicin plus ultraviolet A radiation

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Angular furocoumarin with diverse photobiological effects. Upon long-wavelength UV irradiation, forms monoadduct with double-stranded DNA and reacts with unsaturated fatty acids. Inhibits DNA and RNA synthesis and cell replication in Ehrlich ascites tumor

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Grade

Moligand™

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: C1=CC2=C(C=CO2)C3=C1C=CC(=O)O3
• IUPAC Name: furo[2,3-h]chromen-2-one
• InChIKey: XDROKJSWHURZGO-UHFFFAOYSA-N
• INCHI: 1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H
• Isomeric SMILES: C1=CC2=C(C=CO2)C3=C1C=CC(=O)O3
• RTECS: LV0940000
• Molecular Weight: 186.16
• Reaxy-Rn: 153970
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=153970&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Furanocoumarins
• Intermediate Tree Nodes: Not available
• Direct Parent: Angular furanocoumarins
• Alternative Parents: 1-benzopyrans Benzofurans Pyranones and derivatives Benzenoids Heteroaromatic compounds Furans Lactones Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Angular furanocoumarin - Benzopyran - 1-benzopyran - Benzofuran - Pyranone - Pyran - Benzenoid - Furan - 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 angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.
• 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)

MAOA Tclin Amine oxidase [flavin-containing] A (2 Activities)

Discover Target: MAOA

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ALDH2 Tclin Aldehyde dehydrogenase (509 Activities)

Discover Target: ALDH2

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

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

MAOB Tclin Monoamine oxidase B (8835 Activities)

Discover Target: MAOB

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

CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

Discover Target: CYP1A1

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

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

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

ALDH3A1 Tchem Aldehyde dehydrogenase dimeric NADP-preferring (307 Activities)

Discover Target: ALDH3A1

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

NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

Discover Target: NFKB1

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

BACE1 Tchem Beta-secretase 1 (15641 Activities)

Discover Target: BACE1

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

HL-60 (67320 Activities)

Explore this target

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

HT-1080 (3966 Activities)

Explore this target

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

K562 (73714 Activities)

Explore this target

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

LoVo (4724 Activities)

Explore this target

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

MCF7 (126967 Activities)

Explore this target

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

A549 (127892 Activities)

Explore this target

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

Jurkat (10389 Activities)

Explore this target

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

SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)

Discover Target: SIRT1

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

Associated Targets(non-human)

Mus musculus (284745 Activities)

Explore this target

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

Ehrlich (1318 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat sensitive
• Boil Point(°C): 104 °C/4 mmHg
• Melt Point(°C): 140 °C
• Molecular Weight: 186.160 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 186.032 Da
• Monoisotopic Mass: 186.032 Da
• Topological Polar Surface Area: 39.400 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 284.000
• 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. Liangliang Han, Libo Zhang, Yuedong He, Lijing Liao, Junde Li, Sheng Xu, Yucheng Zhao, Xiaohong Bian, Yuanzheng Xia.  (2023)  Three carbon-/oxygen-prenyltransferases responsible for furanocoumarin synthesis in Angelica dahurica.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2023.116814]

2. Yuling Chen, Rong Wang, Zilin Chen.  (2018)  Sensitive determination of psoralen and isopsoralen in Fructus Psoraleae by online solid phase microextraction with a porphyrin-based porous organic polymer modified capillary.  Analytical Methods,  11  (1): (29-35).  [PMID:] [10.1039/C8AY01885E]

3. Li Xiaotian, Yu Chunbo, Hu Yi, Xia Xinyi, Liao Yue, Zhang Jing, Chen Huiwen, Lu Weili, Zhou Wei, Song Zhongchen.  (2018)  New Application of Psoralen and Angelicin on Periodontitis With Anti-bacterial, Anti-inflammatory, and Osteogenesis Effects.  Frontiers in Cellular and Infection Microbiology,      [PMID:29922598] [10.3389/fcimb.2018.00178]

4. Sun Yujing, Wang Yihua, Zhang Le, Ye Xingqian, Guo Jingtong.  (2024)  Furanocoumarin profiles and inhibitory effects on cytochrome P450 activity of whole citrus fruit.  Food Quality and Safety,      [PMID:] [10.1093/fqsafe/fyae038]

5. Kai Tian, Jiang Zhu, Xinghui Qiu.  (2024)  Metabolism of Furanocoumarins by Three Recombinant CYP9A Proteins From the Polyphagous Cotton Bollworm Helicoverpa armigera.  ARCHIVES OF INSECT BIOCHEMISTRY AND PHYSIOLOGY,  117  (3): (e70004).  [PMID:39494619] [10.1002/arch.70004]