CHEBI:66626 - nigranoic acid

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ChEBI Name nigranoic acid
ChEBI ID CHEBI:66626
Definition A tetracyclic triterpenoid that is 3,4-secocycloarta-4(28),24-(Z)-diene substituted by carboxy groups at positions 3 and 26. Isolated from Schisandra henryi and Schisandra propinqua, it exhibits cytotoxic and anti-HIV activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H46O4
Net Charge 0
Average Mass 470.68380
Monoisotopic Mass 470.33961
InChI InChI=1S/C30H46O4/c1-19(2)22-10-11-24-28(6)14-12-23(20(3)8-7-9-21(4)26(33)34)27(28,5)16-17-30(24)18-29(22,30)15-13-25(31)32/h9,20,22-24H,1,7-8,10-18H2,2-6H3,(H,31,32)(H,33,34)/b21-9-/t20-,22+,23-,24+,27-,28+,29-,30+/m1/s1
InChIKey NJFOSFIPGRXARF-BRTULJEKSA-N
SMILES [H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@@H](C(C)=C)[C@@]4(CCC(O)=O)C[C@@]34CC[C@]12C)[C@H](C)CC\C=C(\C)C(O)=O
Metabolite of Species Details
Kadsura heteroclita (IPNI:554576-1) Found in stem (BTO:0001300). See: PubMed
Schisandra sp.aerandra (IPNI:555079-1) Found in stem (BTO:0001300). See: PubMed
Schisandra henryi (NCBI:txid124789) Found in stem (BTO:0001300). See: PubMed
Schisandra propinqua (NCBI:txid124790) Found in stem (BTO:0001300). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nigranoic acid (CHEBI:66626) has role antineoplastic agent (CHEBI:35610)
nigranoic acid (CHEBI:66626) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
nigranoic acid (CHEBI:66626) has role metabolite (CHEBI:25212)
nigranoic acid (CHEBI:66626) is a dicarboxylic acid (CHEBI:35692)
nigranoic acid (CHEBI:66626) is a tetracyclic triterpenoid (CHEBI:26893)
IUPAC Name
(2Z,6R)-6-[(1R,3aS,3bS,6S,6aR,7aS,9aR)-6a-(2-carboxyethyl)-3a,9a-dimethyl-6-(prop-1-en-2-yl)dodecahydro-1H-cyclopenta[a]cyclopropa[e]naphthalen-1-yl]-2-methylhept-2-enoic acid
Synonym Source
3,4-secocycloarta-4(28),24-(Z)-diene-3,26-dioic acid ChEBI
Registry Numbers Types Sources
2314904 Reaxys Registry Number Reaxys
39111-07-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11395273 PubMed citation Europe PMC
14661856 PubMed citation Europe PMC
16499331 PubMed citation Europe PMC
16557460 PubMed citation Europe PMC
20860030 PubMed citation Europe PMC
21232955 PubMed citation Europe PMC
8778243 PubMed citation Europe PMC
Last Modified
16 April 2013