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CHEBI:66626 - nigranoic acid

ChEBI IDCHEBI:66626
ChEBI Namenigranoic acid
Stars
DefinitionA 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.
Last Modified16 April 2013
DownloadsMolfile
FormulaC30H46O4
Net Charge0
Average Mass470.694
Monoisotopic Mass470.33961
SMILES[H][C@@]12CC[C@@H](C(=C)C)[C@@]3(CCC(=O)O)C[C@]31CC[C@@]1(C)[C@@]2(C)CC[C@]1([H])[C@H](C)CC/C=C(/C)C(=O)O
InChIInChI=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
InChIKeyNJFOSFIPGRXARF-BRTULJEKSA-N
Species of MetaboliteComponentSourceComments
Schisandra sphaerandra (IPNI:555079-1) stem (BTO:0001300) PubMed (8778243)
Schisandra propinqua (ncbitaxon:124790) stem (BTO:0001300) PubMed (11395273)
Schisandra henryi (ncbitaxon:124789) stem (BTO:0001300) PubMed (14661856)
Kadsura heteroclita (IPNI:554576-1) stem (BTO:0001300) PubMed (16557460)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 acidChEBI
Registry NumbersSources
Reaxys:2314904Reaxys
CAS:39111-07-4ChemIDplus
Citations