Basic information
- CAS
72877-50-0- Standard SMILES
Nc1ncnc2c1ncn2C1C=C(CO)C(O)C1O- InChIKey
XUGWUUDOWNZAGW-UHFFFAOYSA-N- Molecular formula
- C11H13N5O3
- Average molar mass
- 263.25 g/mol
- Monoisotopic mass
- 263.10183929
Overview
(-)-neplanocin a is a member of purines and a nucleoside analogue.
Names & identifiers
- Preferred name
- 5-(6-Aminopurin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
- IUPAC
- 5-(6-aminopurin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
- English name
- neplanocin A
- Molecular formula
- C11H13N5O3
- Molecular weight
- 263.25
Names & synonyms
MLS002701806NSC316458NSC-316458CHEMBL9568SCHEMBL863873SCHEMBL30543748CHEBI:1909335-(6-aminopurin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diolNCI60_002719SMR0015654003-Cyclopentene-1, 5-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)-, (1S,2R,5R)-3-Cyclopentene-1, 5-(6-amino-9H-purin-9-yl)- 3-(hydroxymethyl)-, [1S-(1.ALPHA.,2.ALPHA.,5.BETA.)]-
Show more names
A-11079B16NephanocinAneplanocin ANeoplanocin A3-Neplanocin A(?)-Neplanocin AAntibiotic A-11079B16()-Neplanocin A Exclusive(?)-Neplanocin A Exclusive3-Cyclopentene-1,2-diol, 5-(6-amino-9H-purin-9-yl)-3-(hydroxymethyl)-, (1S,2R,5R)-
Database identifiers
- CAS
72877-50-0- PubChem CID
- 330164
- ChEMBL
CHEMBL9568- ChEBI
CHEBI:190933
Properties
Computed structural properties
- XLogP
- -2
- Topological polar surface area
- 130 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 379
Experimental & physicochemical properties
LogP-1.3
Physicochemical properties
- Melting point
- 214 · 214-216 °C (decomp)
- Boiling point
- 632.6 · 632.6±65.0 °C(Predicted)
- Density
- 1.91 · 1.91±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 0.2 mg/ml; · DMF: 0.2 mg/ml; DMSO: 3 mg/ml; PBS (pH 7.2): 0.3 mg/ml
- form
- A crystalline solid
- pka
- 13.43 · 13.43±0.70(Predicted)
- color
- White to off-white
- InChI
- InChI=1S/C11H13N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h1,3-4,6,8-9,17-19H,2H2,(H2,12,13,14)/t6-,8-,9+/m1/s1
- InChIKey
- XUGWUUDOWNZAGW-VDAHYXPESA-N
- SMILES
- [C@H]1(O)[C@H](N2C3C(N=C2)=C(N)N=CN=3)C=C(CO)[C@H]1O
Chemistry & industry
Applications
DescriptionS-Adenosylhomocysteine (SAH) hydrolase catalyzes the reversible hydrolysis of SAH to adenosine and homocysteine. The inhibition of SAH hydrolase causes the intracellular accumulation of SAH, elevating the ratio of SAH to S-adenosylmethionine (SAM) and inhibiting SAM-dependent methyltransferase. (−)-Neplanocin A potently and irreversibly inactivates SAH hydrolase (Ki = 8.39 nM). It has antitumor activity against mouse leukemia L1210 cells and broad-spectrum antiviral activity. Neplanocin A is more potent against vesicular stomatitis than the reversible SAH hydrolase inhibitor 3-deazaneplanocin (ID50 = 0.07 and 0.3 μg/ml, respectively).
UsesNeplanocin A ((-)-Neplanocin A) is an antitumor antibiotic with significant antitumor activity against murine L1210 leukemia. Neplanocin A is also an irreversible inhibitor of AdoHcy hydrolase (Ki=8.39 nM). Neplanocin A also has antiviral activity and is effective against vaccinia virus. Neplanocin A is obtained from Ampulariella regularis[1].
Upstream & downstream products
Upstream raw materials
Suppliers13 total
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
常州宣叶科技有限公司15195022192 · [email protected]
杭州六可生物科技有限公司+86-571-86912261 19975279805 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海宏叶生物科技有限公司400-9205774 400-920-5774 · [email protected]
常州优瑞医药科技有限公司18168818882 · [email protected]
上海扶芃生物科技有限公司13611719524 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…