Myriocin (ISP-1)

Alternative_name

(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid
Description

A fungal metabolite with potent immunosuppressant activity that is 10-100 fold more compared to Cyclosporin A (Cat. No. 1522). It inhibits serine palmitoyltransferase (Ki = 0.28 nM) blocking the synthesis of ceramide. It was found to suppress melanoma cell proliferation by cell cycle arrest at the G 2/M phase through decreased sphingolipid levels and increased p53 and p21 (waf1/cip1) expression.
CAS Number

35891-70-4
Structure Available

Y
Salt Form

No
Molecular Formula

C₂₁H₃₉NO₆
Molecular Weight

401.54
Cell Permeable

Yes
Purity

≥98%
Solubilities

DMSO (~20 mg/ml)
Handling

Protect from air and light
Tag Line

A potent immunosuppressant
Storage Condition

-20°C
Shipping Condition

Gel pack
Shelf Life

24 months
MDL Number

MFCD01632772
PubChem CID

6438394
PubChem CID Link
SMILES

CCCCCCC(=O)CCCCCCC=CCC(C(C(CO)(C(=O)O)N)O)O
InChi

InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
InChi Key

ZZIKIHCNFWXKDY-GNTQXERDSA-N
Data Sheet Link
MSDS Available

Yes

Gene target

Myriocin ISP-1
Gene symbol

IGHVII-1-1, MIR1-1, TRUND-NNN8-1, TRUND-NNN7-1, IGKV1OR2-1, MIR101-1, MIR1289-1, MIR16-1, PIRC1
Short name

Myriocin (ISP-1)
Alternative name

Myriocin (ISP-1)

Identity

HGNC:5670
Gene

IGHVII-1-1
Long gene name

immunoglobulin heavy variable (II)-1-1 (pseudogene)
Synonyms gene name
- immunoglobulin heavy variable (II)-1-1
- immunoglobulin heavy variable (II)-1-1 pseudogene
Synonyms
- IGHV(II)-1-1
GenBank acession
- AB019441
Locus

14q32.33
Discovery year

2000-04-17
Entrez gene record

28377
RefSeq identity
- NG_001019
Classification
- Immunoglobulin heavy locus at 14q32.33
VEGA ID

OTTHUMG00000152325

Identity

HGNC:5760
Gene

IGKV1OR2-1
Long gene name

immunoglobulin kappa variable 1/OR2-1 (pseudogene)
Synonyms gene
- IGKVPZ1
- IGKV1OR-1
Synonyms gene name
- immunoglobulin kappa variable 1/OR-1
- immunoglobulin kappa variable 1/OR-1 pseudogene
- immunoglobulin kappa variable 1/OR-1 (pseudogene)
Synonyms
- IGKV1/OR-1
- IGKV1/OR2-1
GenBank acession
- Z12367
Locus

2p11.1
Discovery year

2000-04-18
Entrez gene record

3531
Pubmed identfication
- 2853098
Classification
- Immunoglobulin kappa (IGK) orphons
VEGA ID

OTTHUMG00000155081