6beta,16beta-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752)

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CHEBI:65752 - 6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid

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ChEBI ID	CHEBI:65752
ChEBI Name	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid
Stars
ASCII Name	6beta,16beta-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid
Definition	A tetracyclic triterpenoid that is 29-nordammara-1,17(20)-diene substituted by acetoxy groups at positions 6 and 16, a carboxy group at position 21, a hydroxy group at position 25 and oxo groups at positions 3 and 7 respectively. It is isolated from the marine-derived fungal strain Aspergillus sydowii PFW1-13 and exhibits antibacterial activity.
Last Modified	27 June 2014
Downloads	Molfile

Formula	C33H46O9
Net Charge	0
Average Mass	586.722
Monoisotopic Mass	586.31418
SMILES	[H][C@]12[C@H](C)C(=O)C=C[C@]1(C)[C@]1([H])CC[C@@]3([H])/C(=C(\CCCC(C)(C)O)C(=O)O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]1(C)C(=O)[C@H]2OC(C)=O
InChI	InChI=1S/C33H46O9/c1-17-22(36)13-15-31(6)24-12-11-21-25(20(29(38)39)10-9-14-30(4,5)40)23(41-18(2)34)16-32(21,7)33(24,8)28(37)27(26(17)31)42-19(3)35/h13,15,17,21,23-24,26-27,40H,9-12,14,16H2,1-8H3,(H,38,39)/b25-20-/t17-,21+,23+,24+,26-,27+,31-,32+,33-/m1/s1
InChIKey	WLRJWQXWJBEULT-GAZAAFLYSA-N

Species of Metabolite	Component	Source	Comments
Aspergillus sydowii (ncbitaxon:75750)	-	PubMed (18505285)	Strain: PFW1 13

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .

ChEBI Ontology

Outgoing Relation(s)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) has role Aspergillus metabolite (CHEBI:76956)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) has role antibacterial agent (CHEBI:33282)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) is a 3-oxo-Δ¹ steroid (CHEBI:20156)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) is a acetate ester (CHEBI:47622)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) is a cyclic ketone (CHEBI:3992)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) is a oxo monocarboxylic acid (CHEBI:35871)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) is a tertiary alcohol (CHEBI:26878)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) is a tetracyclic triterpenoid (CHEBI:26893)
	6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (CHEBI:65752) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)

IUPAC Name
(2Z)-2-[(4α,5α,6β,8α,9β,13α,14β,16β,17Z)-6,16-bis(acetyloxy)-4,8,10,14-tetramethyl-3,7-dioxogon-1-en-17-ylidene]-6-hydroxy-6-methylheptanoic acid

Synonym	Source
(4S,5S,6S,8S,9S,10R,13R,14S,16S,17Z)-6,16-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid	ChEBI

Registry Numbers	Sources
Reaxys:18842465	Reaxys

Citations