3-NPA

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 463822

CAS#: 504-88-1

Description: 3-NPA is an inhibitor of mitochondrial complex I (CI) and complex II (CII).


Chemical Structure

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3-NPA
CAS# 504-88-1

Theoretical Analysis

MedKoo Cat#: 463822
Name: 3-NPA
CAS#: 504-88-1
Chemical Formula: C3H5NO4
Exact Mass: 119.02
Molecular Weight: 119.076
Elemental Analysis: C, 30.26; H, 4.23; N, 11.76; O, 53.74

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: 3-NPA; 3NPA; 3 NPA; Hiptagenic acid; Bovinocidin;

IUPAC/Chemical Name: 3-nitropropanoic acid

InChi Key: WBLZUCOIBUDNBV-UHFFFAOYSA-N

InChi Code: InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)

SMILES Code: O=C(O)CC[N+]([O-])=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 119.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Ranganayaki S, Jamshidi N, Aiyaz M, Rashmi SK, Gayathri N, Harsha PK, Padmanabhan B, Srinivas Bharath MM. Inhibition of mitochondrial complex II in neuronal cells triggers unique pathways culminating in autophagy with implications for neurodegeneration. Sci Rep. 2021 Jan 15;11(1):1483. doi: 10.1038/s41598-020-79339-2. PMID: 33452321.

2: Ranganayaki S, Govindaraj P, Gayathri N, Srinivas Bharath MM. Exposure to the neurotoxin 3-nitropropionic acid in neuronal cells induces unique histone acetylation pattern: Implications for neurodegeneration. Neurochem Int. 2020 Nov;140:104846. doi: 10.1016/j.neuint.2020.104846. Epub 2020 Sep 11. PMID: 32927024.

3: De L, Yuan T, Yong Z. ST1926 inhibits glioma progression through regulating mitochondrial complex II. Biomed Pharmacother. 2020 Aug;128:110291. doi: 10.1016/j.biopha.2020.110291. Epub 2020 Jun 8. PMID: 32526455.

4: Wiprich MT, Zanandrea R, Altenhofen S, Bonan CD. Influence of 3-nitropropionic acid on physiological and behavioral responses in zebrafish larvae and adults. Comp Biochem Physiol C Toxicol Pharmacol. 2020 Aug;234:108772. doi: 10.1016/j.cbpc.2020.108772. Epub 2020 Apr 27. PMID: 32353558.

5: Guo X, Zhu N, Lou Y, Ren S, Pang S, He Y, Chen XB, Shi Z, Feng S. A stable nanoscaled Zr-MOF for the detection of toxic mycotoxin through a pH-modulated ratiometric luminescent switch. Chem Commun (Camb). 2020 May 19;56(40):5389-5392. doi: 10.1039/d0cc01006e. PMID: 32285888.

6: Min HY, Jang HJ, Park KH, Hyun SY, Park SJ, Kim JH, Son J, Kang SS, Lee HY. The natural compound gracillin exerts potent antitumor activity by targeting mitochondrial complex II. Cell Death Dis. 2019 Oct 24;10(11):810. doi: 10.1038/s41419-019-2041-z. PMID: 31649278; PMCID: PMC6813327.

7: Zhang XY, Xiong YM, Tan YJ, Wang L, Li R, Zhang Y, Liu XM, Lin XH, Jin L, Hu YT, Tang ZH, Wu ZM, Yin FH, Wang ZQ, Xiao Y, Sheng JZ, Huang HF. Melatonin rescues impaired penetration ability of human spermatozoa induced by mitochondrial dysfunction. Reproduction. 2019 Nov;158(5):465-475. doi: 10.1530/REP-19-0231. PMID: 31505459.

8: Matsuura K, Wang WH, Ching A, Chen Y, Cheng CM. Paper-Based Resazurin Assay of Inhibitor-Treated Porcine Sperm. Micromachines (Basel). 2019 Jul 25;10(8):495. doi: 10.3390/mi10080495. PMID: 31349635; PMCID: PMC6723269.

9: Abdelfattah MS, Badr SEA, Lotfy SA, Attia GH, Aref AM, Abdel Moneim AE, Kassab RB. Rutin and Selenium Co-administration Reverse 3-Nitropropionic Acid- Induced Neurochemical and Molecular Impairments in a Mouse Model of Huntington's Disease. Neurotox Res. 2020 Jan;37(1):77-92. doi: 10.1007/s12640-019-00086-y. Epub 2019 Jul 22. PMID: 31332714.

10: Wu Y, Zhang J. [Determination of 3-nitropropionic acid in moldy sugarcane by gel filtration-high performance liquid chromatography]. Wei Sheng Yan Jiu. 2019 May;48(3):474-481. Chinese. PMID: 31133137.

11: Jang M, Choi JH, Chang Y, Lee SJ, Nah SY, Cho IH. Gintonin, a ginseng- derived ingredient, as a novel therapeutic strategy for Huntington's disease: Activation of the Nrf2 pathway through lysophosphatidic acid receptors. Brain Behav Immun. 2019 Aug;80:146-162. doi: 10.1016/j.bbi.2019.03.001. Epub 2019 Mar 7. PMID: 30853569.

12: Wei Q, Wu G, Xing J, Mao D, Hutz RJ, Shi F. Roles of poly (ADP-ribose) polymerase 1 activation and cleavage in induction of multi-oocyte ovarian follicles in the mouse by 3-nitropropionic acid. Reprod Fertil Dev. 2019 Apr;31(5):1017-1032. doi: 10.1071/RD18406. PMID: 30836053.

13: Peraza AV, Guzmán DC, Brizuela NO, Herrera MO, Olguín HJ, Silva ML, Tapia BJ, Mejía GB. Riboflavin and pyridoxine restore dopamine levels and reduce oxidative stress in brain of rats. BMC Neurosci. 2018 Nov 9;19(1):71. doi: 10.1186/s12868-018-0474-4. PMID: 30413185; PMCID: PMC6230234.

14: Cao W, Wu Z, Liang C, Jing P, Cui S, Yang G, Lin L. [Determination of deltamethrin and its toxicity biomarkers in rabbit urine by high performance liquid chromatography-tandem mass spectrometry]. Se Pu. 2018 Jun 8;36(6):523-530. Chinese. doi: 10.3724/SP.J.1123.2018.03002. PMID: 30136473.

15: Kang B, Wang X, Xu Q, Wu Y, Si X, Jiang D. Effect of 3-nitropropionic acid inducing oxidative stress and apoptosis of granulosa cells in geese. Biosci Rep. 2018 Sep 12;38(5):BSR20180274. doi: 10.1042/BSR20180274. PMID: 30042167; PMCID: PMC6131328.

16: Nadal X, Del Río C, Casano S, Palomares B, Ferreiro-Vera C, Navarrete C, Sánchez-Carnerero C, Cantarero I, Bellido ML, Meyer S, Morello G, Appendino G, Muñoz E. Tetrahydrocannabinolic acid is a potent PPARγ agonist with neuroprotective activity. Br J Pharmacol. 2017 Dec;174(23):4263-4276. doi: 10.1111/bph.14019. Epub 2017 Nov 2. PMID: 28853159; PMCID: PMC5731255.

17: Kim EJ, Jang M, Lee MJ, Choi JH, Lee SJ, Kim SK, Jang DS, Cho IH. Schisandra chinensis Stem Ameliorates 3-Nitropropionic Acid-Induced Striatal Toxicity via Activation of the Nrf2 Pathway and Inhibition of the MAPKs and NF-κB Pathways. Front Pharmacol. 2017 Sep 29;8:673. doi: 10.3389/fphar.2017.00673. PMID: 29033839; PMCID: PMC5627181.

18: Becker T, Pasteels J, Weigel C, Dahse HM, Voigt K, Boland W. A tale of four kingdoms - isoxazolin-5-one- and 3-nitropropanoic acid-derived natural products. Nat Prod Rep. 2017 Apr 5;34(4):343-360. doi: 10.1039/c6np00122j. PMID: 28271107.

19: Polonio JC, Ribeiro MA, Rhoden SA, Sarragiotto MH, Azevedo JL, Pamphile JA. 3-Nitropropionic acid production by the endophytic Diaporthe citri: Molecular taxonomy, chemical characterization, and quantification under pH variation. Fungal Biol. 2016 Dec;120(12):1600-1608. doi: 10.1016/j.funbio.2016.08.006. Epub 2016 Aug 20. PMID: 27890093.