An indole diterpene fungal metabolite with diverse biological activities
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Shearinine A

Item No. 45475

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3R,5bS,6,7,7aS,8,10,10aS,11,13,16,16bS,16cR,17,18-hexadecahydro-5b-hydroxy-2,2,11,11,13,13,16b,16c-octamethyl-4H-3,18aS-epoxy-1-benzoxepino[6′,7′:6,7]indeno[1,2-b]pyrano[4′,3′:3,4]cyclopent[1,2-f]indol-4-one
CAS Number
163136-24-1
Synonyms
  • (+)-Shearinine A
Molecular Formula
C37H45NO5
Formula Weight
583.8
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
[H][C@@]12C(C)(OC(C)(C=C1C3=C(C=C4C(NC5=C4C[C@@]6(CC[C@]7(O)[C@](C)(CC[C@]89OC(C)([C@](C(C=C87)=O)(O9)[H])C)[C@]65C)[H])=C3)C2)C)C
InChi Code
InChI=1S/C37H45NO5/c1-31(2)18-24-21-16-26-22(13-19(21)14-25(24)32(3,4)42-31)23-15-20-9-10-36(40)28-17-27(39)30-33(5,6)43-37(28,41-30)12-11-34(36,7)35(20,8)29(23)38-26/h13,16-18,20,25,30,38,40H,9-12,14-15H2,1-8H3/t20-,25-,30-,34+,35+,36+,37-/m0/s1
InChi Key
YAGQIZPAJNEIKG-JHMFTDMYSA-N
Origin
Bacterium/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    250 µg

    $169

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    1 mg

    $608

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    Product Description

    Shearinine A is an indole diterpene that has been found in P. janthinellum and has diverse biological activities.1,2,3 It inhibits protein tyrosine phosphatase 1B (PTP1B), T cell protein tyrosine phosphatase (TCPTP), Src homology region 2 domain-containing phosphatase 1 (SHP-1), and SHP-2 (IC50s = 1.3, 3.8, 2.9, and 4 µM, respectively, in cell-free assays) and induces apoptosis in HL-60 leukemia cells at a concentration of 100 µM.1,2 It is also active against methicillin-resistant S. aureus (MRSA; MIC = 25 µg/ml).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cao, F., Liu, X.-M., Wang, X., et al. Structural diversity and biological activities of indole-diterpenoids from Penicillium janthinellum by co-culture with Paecilomyces formosus. Bioorg. Chem. 141:106863, (2023).

    2. Smetanina, O.F., Kalinovsky, A.I., Khudyakova, Y.V., et al. Indole alkaloids produced by a marine fungus isolate of Penicillium janthinellum Biourge. J. Nat. Prod. 70(6), 906-909 (2007).

    3. Bo, H., Li, L.-H., Zhang, L.-J., et al. Indole-diterpenoids with anti-MRSA activity from the endophytic fungus Aspergillus fumigatus. Chem. Nat. Compd. 61(4), 827-830 (2025).