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Cellocidin

HCID 10971
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
543-21-5
Standard SMILES
NC(=O)C#CC(N)=O
InChIKey
JBTGHKUTYAMZEZ-UHFFFAOYSA-N
Molecular formula
C4H4N2O2
Average molar mass
112.09 g/mol
Monoisotopic mass
112.02727738

Overview

Cellocidin is a dicarboxylic acid diamide resulting from the formal condensation of both of the carboxy groups of butynedioic acid with ammonia. An antibacterial agent produced by Streptomyces chibaensis. It has a role as a metabolite, a pesticide, an antimicrobial agent and an antibacterial agent. It is a primary carboxamide, a dicarboxylic acid diamide and a ynamide. It is functionally related to a butynedioic acid.

Names & identifiers

Preferred name
Cellocidin
IUPAC
but-2-ynediamide
English name
Acetylenedicarboxamide
Molecular formula
C4H4N2O2
Molecular weight
112.09

Names & synonyms

CellocidinACETYLENEDICARBOXAMIDE543-21-52-ButynediamideLenamycinAquamycinRenamycinAcetylene dicarboxamideAcetylenedicarboxylic acid diamideAcetylendicarbonsaeureamidNSC-653811K327HA41T
Show more names
4-Dioxane-21,2-Ethynedicarboxamideacetylenedicarboxylicaciddiamide
NSC-38643DTXSID1060261CHEBI:51763RefChem:124302DTXCID2041672but-2-ynediamideNSC65381MFCD00017146

Database identifiers

CAS
543-21-5
PubChem CID
10971
DTXSID
DTXSID1060261
ChEMBL
CHEMBL1978380
ChEBI
CHEBI:51763
UNII
1K327HA41T
EC Number
684-490-7
Nikkaji
J3.644G

Properties

Computed structural properties

XLogP
-1.2
Topological polar surface area
86.2 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
8
Formal charge
0
Complexity
165

Physicochemical properties

Melting point
179 °C · 179 °C
Boiling point
209.98 °C · 209.98°C (rough estimate)
Density
1.4421 · 1.4421 (rough estimate)
refractive index
1.461 · 1.4610 (estimate)
storage temp.
-20 °C · Store at -20°C
solubility
10 mg/ml; · DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml
form
Fine Crystalline Powder
pka
13.01 · 13.01±0.50(Predicted)
color
Cream to beige
EWG's Food Scores
1 · 1
FDA UNII
1 K327HA41T · 1K327HA41T
EPA Substance Registry System
2 · 2-Butynediamide (543-21-5)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H302 (92.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Hazard information

Hazard Classes and Categories · 2 items

Acute Tox. 4 (92.7%)

Acute toxicity (Oral) - Category 3

Safety data

tsca
TSCA listed
hs_code
29241900
Toxicity
LD50 i.v. in mice: 11 mg/kg (Suzuki)
risk_code
25-21
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
T
safety_code
45-36/37-28A
Hazard statements
H302
Precautionary statements
P264-P270-P301+P312-P330-P501

Chemistry & industry

Uses & manufacturing

General Manufacturing Information2-Butynediamide: INACTIVE
Applications · 2 items

DescriptionCellocidin is an antibiotic originally isolated from S. chibaensis. It is active against various bacterial strains including M. tuberculosis and against the trypanosomes T. brucei and T. rhodesiense (IC50s = 150 and 30 ng/ml, respectively). It inhibits proliferation of LCL1 and LCL2 cells transformed by Epstein-Barr virus (EBV), activates the c-Myc and NF-κB pathways in BC3 and LCL1 cells, and induces necrotic cell death in B cells infected with gammaherpes virus. Cellocidin (100-200 ppm) is protective against bacterial leaf blight in rice plants and inhibits α-ketoglutarate oxidation in X. oryzae, the bacterium that causes leaf blight, when used at a concentration of 1 ppm, suggesting that it inhibits the citric acid cycle. Formulations containing cellocidin have been used as agricultural pesticides.

UsesCellocidin is a small neutral alkyne produced by a number of Streptomyces species, first discovered by Suzuki and colleagues in 1958. Cellocidin has a broad antibacterial, antifungal and antitumor profile due to its ability to react with endogenous thiols like cysteine and glutathione. Cellocidin occurs as a weak active in many bioassays using actinomycete crude extracts and is thus a useful standard for chemical and bioassay dereplication.

Upstream & downstream products

Downstream products

Cyanoacetylene

Suppliers34 total

上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Precautionary statements
264 · P264-P270-P301+P312-P330-P501
Hazard Codes
T
Risk Statements
25 · 25-21
Safety Statements
45 · 45-36/37-28A
TSCA
TSCA listed
HS Code
29241900 · 29241900
Toxicity
50 i.v · LD50 i.v. in mice: 11 mg/kg (Suzuki)
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
Aladdin Scientific[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
Hangzhou Sage Chemical Co., Ltd.+86057186818502 13588463833 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
孟成科技(上海)有限公司400-820-6829 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
Shanghai Scibiotron Pharmaceutical Co., Ltd+86-16621589600 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
上海裕兰生物科技有限公司021-57171705 13817537615 · [email protected]
上海鑫凯化学科技有限公司021-58930698 15921516558 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
上海超岚化工科技中心(原宁波市超明生物科技有限公司)13301662590 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
西安莱茵生物科技有限公司86-(0)29-85992781 17792393971 · [email protected]
Novachemistry44-20819178-90 02081917890 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
江苏艾康生物医药研发有限公司025-58851090 13913916777 · [email protected]
上海琼燕医药科技有限公司086-021-15821262312 15821262312 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
SHANGHAI YOUNG-CHEM CHEMICAL CO., LTD.13817489192 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]

Additional notes

DefinitionChEBI: A dicarboxylic acid diamide resulting from the formal condensation of both of the carboxy groups of butynedioic acid with ammonia. An antibacterial agent produced by Streptomyces chibaensis.