staurosporine (CHEBI:15738)

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CHEBI:15738 - staurosporine

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ChEBI Name	staurosporine

ChEBI ID	CHEBI:15738

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:15106, CHEBI:45788, CHEBI:9252

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

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The Resolver thinks Mol

STU - Ideal conformer

Mrv1927 10282112593D

starting HoverWatcher_5

Time for openFile(STU - Ideal conformer

Mrv1927 10282112593D

61 68 0 0 0 0 999 V2000

-2.0850 -1.6490 -0.8990 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.5220 -0.9220 0.2110 C 0 0 2 0 0 0 0 0 0 0 0 0

-3.3090 0.3310 -0.1370 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.5060 1.1770 -1.1330 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.2200 0.3040 -2.3620 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.4470 -0.9270 -1.9130 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.4390 -1.8470 -3.1360 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0450 -0.6230 -1.6410 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4760 -0.4130 -0.3730 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1620 -0.4100 0.8690 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5660 -0.1640 2.0330 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9580 0.0700 1.9460 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5820 0.0650 0.7020 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8540 -0.1700 -0.4590 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1780 -0.2380 -1.8850 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9680 -0.5120 -2.5640 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9460 -0.6310 -3.9520 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1490 -0.4700 -4.6190 C 0 0 0 0 0 0 0 0 0 0 0 0

3.3310 -0.2030 -3.9520 C 0 0 0 0 0 0 0 0 0 0 0 0

3.3800 -0.0800 -2.5730 C 0 0 0 0 0 0 0 0 0 0 0 0

4.0430 0.3500 0.9560 C 0 0 1 0 0 0 0 0 0 0 0 0

4.1810 0.5080 2.4080 N 0 0 0 0 0 0 0 0 0 0 0 0

2.9740 0.3440 2.9740 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7520 0.4130 4.1680 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.4000 -0.2180 3.1260 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.6600 -0.4920 2.5430 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8000 -0.6050 3.3380 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.6360 -0.4390 4.7030 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4030 -0.1730 5.2710 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2560 -0.0550 4.5050 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4610 -0.6310 1.1710 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.4230 1.0600 -3.2760 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.3270 1.7190 -4.1640 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2420 1.6040 -0.5190 N 0 0 2 0 0 0 0 0 0 0 0 0

-1.5000 2.9000 0.1220 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.2220 -1.5720 0.7350 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4900 0.9100 0.7680 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.2620 0.0480 -0.5850 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0870 2.0510 -1.4280 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1430 -0.0030 -2.8530 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5890 -2.5260 -3.0740 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3640 -2.4230 -3.1630 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3580 -1.2460 -4.0420 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0300 -0.8390 -4.4850 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1650 -0.5550 -5.6960 H 0 0 0 0 0 0 0 0 0 0 0 0

4.2410 -0.0890 -4.5220 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3040 0.1280 -2.0560 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6530 -0.4830 0.6100 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3390 1.2680 0.4490 H 0 0 0 0 0 0 0 0 0 0 0 0

5.0070 0.6990 2.8800 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7690 -0.8120 2.9080 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5000 -0.5210 5.3460 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3330 -0.0540 6.3420 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7040 0.1530 4.9530 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7620 2.3120 -4.8840 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9230 0.9760 -4.6940 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9860 2.3730 -3.5930 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5970 1.7780 -1.2750 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5870 3.2600 0.5940 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8280 3.6180 -0.6290 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2780 2.7830 0.8760 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 6 1 0 0 0 0

2 3 1 0 0 0 0

2 31 1 0 0 0 0

2 36 1 1 0 0 0

3 4 1 0 0 0 0

3 37 1 0 0 0 0

3 38 1 0 0 0 0

4 5 1 0 0 0 0

4 34 1 0 0 0 0

4 39 1 6 0 0 0

5 6 1 0 0 0 0

5 32 1 0 0 0 0

5 40 1 6 0 0 0

6 7 1 6 0 0 0

6 8 1 0 0 0 0

7 41 1 0 0 0 0

7 42 1 0 0 0 0

7 43 1 0 0 0 0

8 9 1 0 0 0 0

8 16 1 0 0 0 0

9 10 2 0 0 0 0

9 14 1 0 0 0 0

10 11 1 0 0 0 0

10 31 1 0 0 0 0

11 12 2 0 0 0 0

11 25 1 0 0 0 0

12 13 1 0 0 0 0

12 23 1 0 0 0 0

13 14 2 0 0 0 0

13 21 1 0 0 0 0

14 15 1 0 0 0 0

15 16 2 0 0 0 0

15 20 1 0 0 0 0

16 17 1 0 0 0 0

17 18 2 0 0 0 0

17 44 1 0 0 0 0

18 19 1 0 0 0 0

18 45 1 0 0 0 0

19 20 2 0 0 0 0

19 46 1 0 0 0 0

20 47 1 0 0 0 0

21 22 1 0 0 0 0

21 48 1 0 0 0 0

21 49 1 0 0 0 0

22 23 1 0 0 0 0

22 50 1 0 0 0 0

23 24 2 0 0 0 0

25 26 2 0 0 0 0

25 30 1 0 0 0 0

26 27 1 0 0 0 0

26 31 1 0 0 0 0

27 28 2 0 0 0 0

27 51 1 0 0 0 0

28 29 1 0 0 0 0

28 52 1 0 0 0 0

29 30 2 0 0 0 0

29 53 1 0 0 0 0

30 54 1 0 0 0 0

32 33 1 0 0 0 0

33 55 1 0 0 0 0

33 56 1 0 0 0 0

33 57 1 0 0 0 0

34 35 1 0 0 0 0

34 58 1 0 0 0 0

35 59 1 0 0 0 0

35 60 1 0 0 0 0

35 61 1 0 0 0 0

M END): 23 ms

reading 61 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

61 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
S-Adenosyl methionine (SAM), also known under the commercial names of SAMe, SAM-e, or AdoMet, is a common cosubstrate involved in methyl group transfers, transsulfuration, and aminopropylation. Although these anabolic reactions occur throughout the body, most SAM is produced and consumed in the liver. More than 40 methyl transfers from SAM are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase. SAM was first discovered by Giulio Cantoni in 1952. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. In eukaryotic cells, SAM serves as a regulator of a variety of processes including DNA, tRNA, and rRNA methylation; immune response; amino acid metabolism; transsulfuration; and more. In plants, SAM is crucial to the biosynthesis of ethylene, an important plant hormone and signaling molecule.
Read full article at Wikipedia

Formula

C28H26N4O3

Net Charge

Average Mass

466.541

Monoisotopic Mass

466.20049

InChI

InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20-,26-,28+/m1/s1

InChIKey

HKSZLNNOFSGOKW-FYTWVXJKSA-N

SMILES

CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)N1C3=C(C=CC=C3)C3=C1C1=C(C4=C(C=CC=C4)N21)C1=C3CNC1=O

Metabolite of Species	Details
Lentzea albida (NCBI:txid65499)	Species also known as Streptomyces staurosporeus. See: DOI

Roles Classification
Biological Role(s):	EC 2.7.11.13 (protein kinase C) inhibitor An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13). bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	staurosporine (CHEBI:15738) has role apoptosis inducer (CHEBI:68495) staurosporine (CHEBI:15738) has role bacterial metabolite (CHEBI:76969) staurosporine (CHEBI:15738) has role EC 2.7.11.13 (protein kinase C) inhibitor (CHEBI:37700) staurosporine (CHEBI:15738) has role geroprotector (CHEBI:176497) staurosporine (CHEBI:15738) is a indolocarbazole alkaloid (CHEBI:37697) staurosporine (CHEBI:15738) is a organic heterooctacyclic compound (CHEBI:38165) staurosporine (CHEBI:15738) is conjugate base of staurosporinium (CHEBI:57491)

Incoming	3'-demethylstaurosporine (CHEBI:15692) has functional parent staurosporine (CHEBI:15738) 7-oxo-3,8,9-trihydroxy staurosporine (CHEBI:66839) has functional parent staurosporine (CHEBI:15738) 7-oxo-8,9-dihydroxy-4'-N-demethyl staurosporine (CHEBI:66840) has functional parent staurosporine (CHEBI:15738) linkable staurosporine analogue (CHEBI:39082) has functional parent staurosporine (CHEBI:15738) midostaurin (CHEBI:63452) has functional parent staurosporine (CHEBI:15738) staurosporinium (CHEBI:57491) is conjugate acid of staurosporine (CHEBI:15738)

IUPAC Name

(5S,6R,7R,9R)-6-methoxy-5-methyl-7-methylamino-6,7,8,9,15,16-hexahydro-5H,14H-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacen-14-one

Synonyms	Sources
(+)-Staurosporine	ChemIDplus
AM-2282	ChemIDplus
antibiotic AM 2282	ChemIDplus
Staurosporin	ChemIDplus
Staurosporine	KEGG COMPOUND
STS	KEGG COMPOUND

Manual Xrefs	Databases
C00018127	KNApSAcK
C02079	KEGG COMPOUND
DB02010	DrugBank
LSM-1103	LINCS
Staurosporine	Wikipedia
STU	PDBeChem
View more database links

Registry Numbers	Types	Sources
62996-74-1	CAS Registry Number	KEGG COMPOUND
62996-74-1	CAS Registry Number	ChemIDplus

Citations	Types	Sources
15613975	PubMed citation	Europe PMC
15682296	PubMed citation	Europe PMC
18478334	PubMed citation	Europe PMC
22363408	PubMed citation	Europe PMC
32800439	PubMed citation	Europe PMC
34428735	PubMed citation	Europe PMC

Last Modified

28 October 2021

CHEBI:15738 - staurosporine

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