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118399-22-7 molecular structure
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(5R,6S,9S,12S,13S,16R)-9-(3-carbamimidamidopropyl)-2-ethylidene-12-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid

ChemBase ID: 155573
Molecular Formular: C41H60N8O10
Molecular Mass: 824.9627
Monoisotopic Mass: 824.44324016
SMILES and InChIs

SMILES:
C/C=C\1/C(=O)N[C@@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H]([C@@H](C(=O)N[C@@H](CCC(=O)N1C)C(=O)O)C)/C=C/C(=C/[C@H](C)[C@H](Cc1ccccc1)OC)/C)CCCNC(=N)N)C)C(=O)O
Canonical SMILES:
CO[C@H]([C@H](/C=C(/C=C/[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@H](NC(=O)/C(=C/C)/N(C(=O)CC[C@H](NC(=O)[C@H]1C)C(=O)O)C)C(=O)O)\C)C)Cc1ccccc1
InChI:
InChI=1S/C41H60N8O10/c1-8-31-38(54)48-34(40(57)58)26(5)36(52)46-29(15-12-20-44-41(42)43)37(53)45-28(25(4)35(51)47-30(39(55)56)18-19-33(50)49(31)6)17-16-23(2)21-24(3)32(59-7)22-27-13-10-9-11-14-27/h8-11,13-14,16-17,21,24-26,28-30,32,34H,12,15,18-20,22H2,1-7H3,(H,45,53)(H,46,52)(H,47,51)(H,48,54)(H,55,56)(H,57,58)(H4,42,43,44)/t24-,25-,26-,28-,29-,30+,32-,34+/m0/s1
InChIKey:
IXBQSRWSVIBXNC-YBOPQVMDSA-N

Cite this record

CBID:155573 http://www.chembase.cn/molecule-155573.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(5R,6S,9S,12S,13S,16R)-9-(3-carbamimidamidopropyl)-2-ethylidene-12-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid
IUPAC Traditional name
(5R,6S,9S,12S,13S,16R)-9-(3-carbamimidamidopropyl)-2-ethylidene-12-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid
Synonyms
1,4,8,11,15-Pentaazacyclononadecane, cyclic peptide
Nodularin
Cyclo[(2S,3S,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoyl-D-γ-glutamyl-(2Z)-2-(methylamino)-2-butenoyl-(3S)-3-methyl-Dβ-aspartyl-L-arginyl)
Nodularin solution
节球毒素
环[(2S,3S,4E,6E,8S,9S)-3-氨基-9-甲氧基-2,6,8-三甲基-10-苯基-4,6-癸二烯酰基-D-γ-谷氨酰基-(2Z)-2-(甲氨基)-2-丁烯酰基-(3S)-3-甲基-Dβ-天冬氨酰-L-精氨酰)
节球毒素 溶液
CAS Number
118399-22-7
EC Number
200-659-6
MDL Number
MFCD16659855
PubChem SID
162249711
PubChem CID
14217092

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 14217092 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.1089077  H Acceptors 13 
H Donor LogD (pH = 5.5) -2.6592486 
LogD (pH = 7.4) -4.174611  Log P -1.183689 
Molar Refractivity 230.9796 cm3 Polarizability 84.15833 Å3
Polar Surface Area 282.44 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
methanol: soluble2 mg/mL (Further dilute to 10% (v/v) methanol. Store solutions at -20°C for up to six months.) expand Show data source
Flash Point
11 °C expand Show data source
51.8 °F expand Show data source
RTECS
GU2294250 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11-23/24/25-39/23/24/25 expand Show data source
26/27/28-36/37/38-43 expand Show data source
Safety Statements
26-36/37/39-45 expand Show data source
7-16-36/37-45 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225-H301 + H311 + H331-H370 expand Show data source
H300 +H310 + H330-H315-H317-H319-H335 expand Show data source
GHS Precautionary statements
P210-P260-P280-P301 + P310-P311 expand Show data source
P260-P264-P280-P284-P301 + P310-P302 + P350 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US) expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Concentration
10 μg/mL in methanol expand Show data source
Grade
analytical standard, for environmental analysis expand Show data source
Empirical Formula (Hill Notation)
C41H60N8O10 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - N5148 external link
Biochem/physiol Actions
Potent inhibitor of protein phosphatases types 1 and 2A. Tumor promoter in experimental animal model.1; at higher doses, causes massive liver hemorrhage. Tumor-promoting effect is due to increasing oxidative stress, as evidenced by reduced levels of glutathione and appearance of oxidative damage in DNA bases.2

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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