Basic information
- Standard SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O- InChIKey
IVOMOUWHDPKRLL-KQYNXXCUSA-N- Molecular formula
- C10H12N5O6P
- Average molar mass
- 329.21 g/mol
- Monoisotopic mass
- 329.05251973
Overview
3',5'-cyclic AMP is a 3',5'-cyclic purine nucleotide having having adenine as the nucleobase. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a 3',5'-cyclic purine nucleotide and an adenyl ribonucleotide. It is a conjugate acid of a 3',5'-cyclic AMP(1-).
Names & identifiers
- Preferred name
- Camp
- IUPAC
- (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
- English name
- Cyclic AMP
- Molecular formula
- C10H12N5O6P
- Molecular weight
- 329.21
Names & synonyms
Cyclic AMPcAMP60-92-4Adenosine 3',5'-cyclic monophosphate3',5'-cyclic AMPAdenosine 3',5'-cyclophosphatecyclic 3',5'-AMPAdenosine 3',5'-phosphateCyclic Adenosine MonophosphateAdenosine cyclic monophosphatecyclic 3',5'-Adenylic acidAdenosine 3',5'-monophosphate
Show more names
ADENOSINE CYCLOPHOSPHATEAcrasinADENOSINE CYCLPHOSPHATE(4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)-2,7-dihydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine 2-oxideMRD40C13orf83:5-CAMPKIAA1802
cyclic Adenosine 3',5'-phosphateAdenosine cyclic 3',5'-monophosphateAdenosine, cyclic 3',5'-(hydrogen phosphate)Adenosine 3',5'-cyclic phosphate3',5'-AMPAdenosine cyclic 3',5'-phosphateAdenosine cyclic phosphateCyclic adenylic acid
Database identifiers
- CAS
60-92-4- PubChem CID
- 6076
- DTXSID
DTXSID8040436- ChEMBL
CHEMBL316966- ChEBI
CHEBI:17489- UNII
- E0399OZS9N
- EC Number
- 200-492-9
- Nikkaji
- J4.811I
Properties
Computed structural properties
- XLogP
- -2.6
- Topological polar surface area
- 155 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 498
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning
LogP-2.96
Solubility4 mg/mL
Melting Point
219-220 °C
219 - 220 °C
Physical DescriptionSolid
Collision Cross Section
176.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
172 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
175.07 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
188.8 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
181.3 Ų [M+Na]+
Physicochemical properties
- Melting point
- 260 °C · 260 °C (dec.)(lit.)
- Boiling point
- 56.12 °C · 56.12°C
- alpha
- -53.7 · -53.7 º (c=0.7,water)
- Density
- 2.47 · 2.47±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 2 O: · H2O: 10 mg/mL pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20×
- pka
- 1 · 1.00±0.60(Predicted)
- form
- powder
- color
- white
- biological source
- mouse
- Water Solubility
- 50 mg/mL · 50 mg/mL
- Merck
- 14 · 14,2708
- BRN
- 52645 · 52645
- Stability
- Hygroscopic
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
- InChIKey
- IVOMOUWHDPKRLL-KQYNXXCUSA-N
- SMILES
- Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O
- FDA UNII
- 399 OZS9N · E0399OZS9N
- NIST Chemistry Reference
- 3 · Adenosine 3',5'-cyclic monophosphate(60-92-4)
- EPA Substance Registry System
- 3 · Adenosine, cyclic 3',5'-(hydrogen phosphate) (60-92-4)
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 264 b-P280-P301+P330+P331-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501c · P264b-P280-P301+P330+P331-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501c
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- C,Xi
- Risk Statements
- 34 · 34-36/37/38
- Safety Statements
- 22 · 22-24/25-45-36/37/39-26-36
- WGK Germany
- 3 · 3
- RTECS
- 7357600 · AU7357600
- F
- 10 · 10-21
- TSCA
- TSCA listed
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 100 mmol/L · oms-hmn:oth 100 mmol/L JIDEAE 65,52,75
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (2 of 6) of reports.
Danger
H314 (16.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Adenosine, cyclic 3',5'-(hydrogen phosphate)
Adenosine, cyclic 3',5'-(hydrogen phosphate): Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Adenosine, cyclic 3',5'-(hydrogen phosphate): Environment tier I assessment
Hazard Classes and CategoriesSkin Corr. 1B (16.7%)
Safety data
- F
- 10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AU7357600
- hs_code
- 29349990
- Toxicity
- oms-hmn:oth 100 mmol/L JIDEAE 65,52,75
- risk_code
- 34-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C,Xi
- safety_code
- 22-24/25-45-36/37/39-26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H314
- Precautionary statements
- P264b-P280-P301+P330+P331-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501c
Chemistry & industry
Pharmacology
Tissue LocationsAll Tissues
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
Uses & manufacturing
Household ProductsInformation on 1 consumer products that contain cyclic AMP (adenosine cyclic phosphate) in the following categories is provided:
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationAdenosine, cyclic 3',5'-(hydrogen phosphate): ACTIVE
Applications
UsescAMP is used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway. Restoration of several morphological characteristics of normal fibroblasts in sarcoma cells when treated with adenosine-3': 5'-cyclic monophosphate. In the presence of adenosine 3':5'-cyclic monophosphate, protein kinase I dissociated into two subunits: a subunit binding adenosine 3':5'-cyclic monophosphate, and a catalytic subunit. Stimulation of calcium uptake in platelet membrane vesicles by adenosine 3',5'-cyclic monophosphate.
General DescriptionCyclic AMP is a second messenger molecule comprised of an adenine ribonucleotide bearing a phosphate group bound to the oxygen molecules at the 3' and 5' positions of the sugar moiety. Cyclic AMP, which is synthesized from ATP by the intracellular enzyme adenylate cyclase, modulates the activity of several hormone-dependent signal transduction pathways.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
河北立业化学制品有限公司0310-6697998 13930001710 · [email protected]
江苏艾赛科生物技术有限公司0512-58587898 13812862084
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
杭州美亚药业股份有限公司021-33686691 18001850931 · [email protected]
南京奥生化学技术有限公司+86 (25) 82263158
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
Advent Bio, Inc.(630) 889-9003 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
上海创赛科技有限公司400-6087598 15021221957 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
成都润泽本土化工有限公司13096311329 028-88469284 616445927 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技（武汉）有限公司027-59207879 1972026995 18140587686 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
Additional notes
DefinitionChEBI: Cyclic AMP is a 3',5'-cyclic purine nucleotide having having adenine as the nucleobase. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an adenyl ribonucleotide and a 3',5'-cyclic purine nucleotide. It is a conjugate acid of a 3',5'-cyclic AMP(1-).
Related reactions
19 records
Linked notes
Loading…