Siomycin A

CAT: 0804-HY-P1687-01Size: 500 µgDry Ice: NoHazardous: No

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CAT#:0804-HY-P1687-01Size:500 µg

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Description

Siomycin A is a thiopeptide antibiotic and is a Forkhead box M1 (FOXM1) selective inhibitor without affecting other members of the Forkhead box family. Siomycin A has anti-tumor and promotes apoptosis[1][2].

CAS Number

12656-09-6

UNSPSC

12352005

Target

Antibiotic; Apoptosis; Bacterial

Type

Reference compound

Related Pathways

Anti-infection; Apoptosis

Applications

Cancer-programmed cell death

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/siomycin-a.html

Solubility

10 mM in DMSO

Smiles

O=C1N[C@]23[C@@](N=C(C4=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS4)CC3)([H])C5=CSC([C@@]([C@H](OC(C6=CC([C@@H](O)C)=C7C([C@](O)([H])[C@@H](C=C7)N[C@](C(C)C)([H])C(NC(C(NC(C(N[C@H]1C)=O)=C)=O)=C)=O)=N6)=O)C)([H])NC(C8=CSC([C@](NC([C@]9([H])N=C(SC9)/C(NC(C([C@H](O)C)NC(C%10=CSC2=N%10)=O)=O)=C/C)=O)([H])[C@](C)(O)[C@H](O)C)=N8)=O)=N5

Molecular Formula

C71H81N19O18S5

Molecular Weight

1648.84

References & Citations

[1]Wang B, et al. Effects and mechanism of siomycin A on the growth and apoptosis of MiaPaCa-2 cancer cells. Oncol Lett. 2019 Sep;18 (3) :2869-2876.|[2]Kim H, et al. Forkhead box M1 (FOXM1) transcription factor is a key oncogenic driver of aggressive human meningioma progression. Neuropathol Appl Neurobiol. 2019 Jun 9.

Shipping Conditions

Room temperature

Scientific Category

Reference compound1

Clinical Information

No Development Reported

Chemical Information

Siomycin A

siomycin a has been reported in Planomonospora parontospora and Planomonospora sphaerica with data available.

CAS Number	12656-09-6
PubChem CID	121225689
IUPAC Name	N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[(1R,8S,11Z,15S,18S,25S,26R,35R,37S,46S,53S,59S)-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-31-[(1S)-1-hydroxyethyl]-26,46-dimethyl-40,43-dimethylidene-6,9,16,23,28,38,41,44,47-nonaoxo-37-propan-2-yl-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide
Molecular Formula	C71H81N19O18S5
Molecular Weight	1648.9
XLogP	0.5
Topological Polar Surface Area	701
Hydrogen Bond Donor Count	17
Hydrogen Bond Acceptor Count	31
Rotatable Bond Count	11
Heavy Atom Count	113
Formal Charge	0
Complexity	3970

SMILES

C/C=C\1/C2=N[C@H](CS2)C(=O)N[C@H](C3=NC(=CS3)C(=O)N[C@H]4[C@H](OC(=O)C5=NC6=C(C=C[C@H]([C@@H]6O)N[C@H](C(=O)NC(=C)C(=O)NC(=C)C(=O)N[C@H](C(=O)N[C@@]7(CCC(=N[C@@H]7C8=CSC4=N8)C9=NC(=CS9)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C2=NC(=CS2)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)C)C(C)C)C(=C5)[C@H](C)O)C)[C@@](C)([C@@H](C)O)O

InChI

InChI=1S/C71H81N19O18S5/c1-14-37-64-83-44(22-109-64)61(103)89-52(70(13,107)34(12)93)67-85-43(23-112-67)59(101)88-48-33(11)108-68(106)40-19-36(31(9)91)35-15-16-38(50(94)49(35)79-40)78-46(25(2)3)62(104)77-29(7)56(98)74-27(5)55(97)75-30(8)57(99)90-71(69-86-45(24-113-69)60(102)87-47(32(10)92)63(105)81-37)18-17-39(80-51(71)41-20-111-66(48)82-41)65-84-42(21-110-65)58(100)76-28(6)54(96)73-26(4)53(72)95/h14-16,19-21,23-25,30-34,38,44,46-48,50-52,78,91-94,107H,4-7,17-18,22H2,1-3,8-13H3,(H2,72,95)(H,73,96)(H,74,98)(H,75,97)(H,76,100)(H,77,104)(H,81,105)(H,87,102)(H,88,101)(H,89,103)(H,90,99)/b37-14-/t30-,31-,32+,33+,34+,38+,44+,46-,47-,48-,50-,51+,52+,70+,71+/m0/s1

InChIKey

AKFVOKPQHFBYCA-KJULAZMPSA-N

Chemical Structure

2D Structure

CAS: 12656-09-6

CID: 121225689

Formula: C71H81N19O18S5

MW: 1648.9

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	1648.9
XLogP3	0.5
Hydrogen Bond Donor Count	17
Hydrogen Bond Acceptor Count	31
Rotatable Bond Count	11
Exact Mass	1647.4610527
Monoisotopic Mass	1647.4610527
Topological Polar Surface Area	701 Å²
Heavy Atom Count	113
Formal Charge	0
Complexity	3970
Isotope Atom Count	0
Defined Atom Stereocenter Count	15
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
GTR19227602	Siomycin A
S1013-86W	Siomycin A (Mutabilycin, Sporangiomycin, Antibiotic 6741-21, Mutabillicin)

Siomycin A

Chemical Information

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