Usaramine - Moligand™,≥98% , CAS No.15503-87-4

CAS: 15503-87-4 Cat. No.: U359348 Formula:  C₁₈H₂₅NO₆  Molecular Weight: 351.39 EC Number: 112-280-2 PubChem CID: 5281756

GRADE & PURITY Moligand™, ≥98%

Synonyms

(5R,6S,9a1R,14aR,E)-3-Ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione|trans-Retrorsine|(15E)-Retrorsine|USARAMINE;MUCRONATINE|Usaramine|(+)-Ursamine|[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3E,5R,6S,14aR,14bR)-|Usaramin|(1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione|Mucronatine|Senecionan-11,16-dione, 12,18-dihydroxy-, (15E)-

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Specifications

Synonyms

(5R,6S,9a1R,14aR,E)-3-Ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione | trans-Retrorsine | (15E)-Retrorsine | USARAMINE;MUCRONATINE | Usaramine | (+)-Ursamine | [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14 Show more

Specifications & Purity

Moligand™,≥98%

Biochemical and Physiological Mechanisms

Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50% of biofilm formation without killing the bacteria.

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

Canonical Smiles

CC=C1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(CO)O)C

IUPAC Name

(1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

InChIKey

BCJMNZRQJAVDLD-FXGRWVCYSA-N

INCHI

1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1

Isomeric SMILES

C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)C

PubChem CID

5281756

Molecular Weight

351.39

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Macrolides and analogues

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Macrolides and analogues
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolides and analogues
• Alternative Parents: Alkaloids and derivatives Pyrrolizines N-alkylpyrrolidines Dicarboxylic acids and derivatives Tertiary alcohols Pyrrolines Enoate esters Trialkylamines 1,2-diols Amino acids and derivatives Lactones Oxacyclic compounds Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary alcohols
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Senecionan-skeleton - Macrolide - Alkaloid or derivatives - Pyrrolizine - Dicarboxylic acid or derivatives - N-alkylpyrrolidine - Pyrrolidine - Pyrroline - Tertiary alcohol - Alpha,beta-unsaturated carboxylic ester - Enoate ester - 1,2-diol - Amino acid or derivatives - Carboxylic acid ester - Lactone - Tertiary amine - Tertiary aliphatic amine - Carboxylic acid derivative - Oxacycle - Azacycle - Organoheterocyclic compound - Organic oxide - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Amine - Alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
• External Descriptors: Pyrrolizidine alkaloids

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)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

A204 (242 Activities)

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

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Spodoptera littoralis (798 Activities)

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Myzus persicae (1112 Activities)

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CHO (4503 Activities)

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Lactuca sativa (1092 Activities)

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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

Leptinotarsa decemlineata (1161 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Moisture sensitive, Light sensitive
• Melt Point(°C): 212.0 °C
• Molecular Weight: 351.400 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 351.168 Da
• Monoisotopic Mass: 351.168 Da
• Topological Polar Surface Area: 96.300 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 627.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How should this product be stored?

Store at 2–8 °C, protected from light, under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 15503-87-4, the molecular formula is C18H25NO6, and the molecular weight is 351.39 g/mol. InChIKey BCJMNZRQJAVDLD-FXGRWVCYSA-N.