(S)-4-hydroxymandelonitrile β-D-glucoside

CHEBI:27826 EXACT SEEDED enzyme inhibitor

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

A β-D-glucoside consisting of (S)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring.

Structure

Standard InChIKey	NVLTYOJHPBMILU-YOVYLDAJSA-N
SMILES	C1=CC(=CC=C1[C@@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
Stereochemistry	fully defined
Cross-references	pubchem:161355

Filing pathway

Amino acids and peptides — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is saccharide, from MIBiG.

Producer organisms 1

A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.

Taxon	Basis	Cluster	Evidence
Sorghum bicolor NCBITaxon:4558	SOURCE_ASSERTION	mibig:BGC0000798	PMID:21707799

Occurrences 25

Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.

Taxon	Source	Reference
Hakea bucculenta NCBITaxon:1136183	LOTUS	DOI:10.1016/0031-9422(89)80122-0
Hakea multilineata NCBITaxon:1136201	LOTUS	DOI:10.1016/0031-9422(89)80122-0
Hakea petiolaris NCBITaxon:1136206	LOTUS	DOI:10.1016/0031-9422(89)80122-0
Campylospermum flavum NCBITaxon:1321791	LOTUS	DOI:10.1016/J.PHYTOCHEM.2010.08.006
Ostrya virginiana NCBITaxon:13622	LOTUS	DOI:10.1016/J.PHYTOCHEM.2005.02.021
Chamaebatia foliolosa NCBITaxon:140996	LOTUS	DOI:10.1016/S0031-9422(00)81860-9
Tiquilia plicata NCBITaxon:203761	LOTUS	DOI:10.1016/J.PHYTOCHEM.2005.02.021
Hydrangea macrophylla NCBITaxon:23110	LOTUS	DOI:10.1016/J.TETLET.2009.05.111
Hydrangea macrophylla NCBITaxon:23110	LOTUS	DOI:10.3987/COM-09-11886
Caroxylon tetrandrum NCBITaxon:264975	LOTUS	DOI:10.1021/NP060222W
Cercocarpus ledifolius NCBITaxon:32221	LOTUS	DOI:10.1016/0031-9422(82)83111-7
Guadua angustifolia NCBITaxon:323898	LOTUS	DOI:10.1002/CBER.19761091016
Hakea bakeriana NCBITaxon:3815949	LOTUS	DOI:10.1016/0031-9422(89)80122-0
Macadamia ternifolia NCBITaxon:4330	LOTUS	DOI:10.1016/0031-9422(89)80122-0
Sorghum halepense NCBITaxon:4560	LOTUS	DOI:10.1021/JF00118A016
Suckleya suckleyana NCBITaxon:525239	LOTUS	DOI:10.1016/0031-9422(93)85288-3
Bambusa vulgaris NCBITaxon:58168	LOTUS	DOI:10.1002/CBER.19761091016
Henriettea fascicularis NCBITaxon:883786	LOTUS	DOI:10.1002/CHIN.200330215
Sorghum arundinaceum NCBITaxon:91525	LOTUS	DOI:10.1016/S0031-9422(00)80775-X
Guazuma ulmifolia NCBITaxon:93772	LOTUS	DOI:10.1016/J.PHYTOCHEM.2005.02.021
Sorghum bicolor NCBITaxon:4558	LOTUS	DOI:10.1006/ABBI.1995.0024
Sorghum bicolor NCBITaxon:4558	LOTUS	DOI:10.1016/0031-9422(96)00297-X
Sorghum bicolor NCBITaxon:4558	LOTUS	DOI:10.1016/S0021-9258(17)45334-8
Sorghum bicolor NCBITaxon:4558	LOTUS	DOI:10.1073/PNAS.88.2.487
Sorghum bicolor NCBITaxon:4558	LOTUS	DOI:10.1074/JBC.270.8.3506

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000798	Sorghum bicolor NCBITaxon:4558	CLUSTER_UNSTATED	genbank:CM000760.1

A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 2 nodes, 1 edge

Dhurrin binds the inactive E191D maize ZmGlu1 beta-glucosidase construct captured in PDB 1E55.

Subject	Predicate	Object	Notes	Evidence
(S)-4-hydroxymandelonitrile β-D-glucoside	binds	maize beta-glucosidase ZmGlu1	PubChem BioAssay AID 977610 maps the exact Standard InChIKey NVLTYOJHPBMILU-YOVYLDAJSA-N to an active 76 uM Ki row for PDB 1E55 chain A. RCSB maps both 1E55 protein chains to the Zea mays UniProtKB:P49235 sequence, with deposited residues 1-512 corresponding to UniProt residues 55-566 and an engineered E191D substitution corresponding to Glu245 in the canonical sequence. PDB 1E55 models dhurrin as covalently connected BGC beta-D-glucopyranose and DHR (2S)-hydroxy(4-hydroxyphenyl)ethanenitrile components in each active site.	DOI:10.1073/pnas.97.25.13555 DOI:10.2210/pdb1e55/pdb reference DOI:10.1073/pnas.97.25.13555 evidence type PRIMARY_EXPERIMENT snippet mutant maize beta-glucosidase-DIMBOA, -DIMBOAGlc, and -dhurrin complexes notes Czjzek et al. reported the dhurrin-bound inactive maize ZmGlu1 beta-glucosidase structure deposited as PDB 1E55. reference DOI:10.2210/pdb1e55/pdb evidence type DATABASE_ASSERTION snippet Crystal structure of the inactive mutant Monocot (Maize ZMGlu1) beta-glucosidase ZMGluE191D in complex with the competitive inhibitor dhurrin notes RCSB PDB identifies chains A and B as maize ZmGlu1 beta-glucosidase and maps them to UniProtKB:P49235; BGC and DHR nonpolymer components are covalently linked as dhurrin in each 1E55 active site.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Bioactivities 2

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

Assay	Result	Target enzyme	Source detail
Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB	KI 76 uM; ACTIVE	Not recorded	PMID:11106394 assay Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB evidence reference PMID:11106394 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 977610, deposited by Shanghai Institute of Organic Chemistry; assay type Other. Target accession 1E55_A was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type KI value 76.0 units uM activity class ENZYME_INHIBITOR
Experimentally measured binding affinity data derived from PDB	ACTIVE	Not recorded	PMID:11106394 assay Experimentally measured binding affinity data derived from PDB evidence reference PMID:11106394 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1811, deposited by Shanghai Institute of Organic Chemistry; assay type Other. Target accession 1E55_A was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE activity class ENZYME_INHIBITOR

Explore across X-Mech

AntibioticMech ((S)-4-hydroxymandelonitrile β-D-glucoside) ↗ MediaIngredientMech (CHEBI:27826) ↗ TaxonMech: Sorghum bicolor (NCBITaxon:4558) ↗ PathwayMech (mibig:BGC0000798) ↗

Open questions 1

name-disagreement — ChEBI calls this structure '(S)-4-hydroxymandelonitrile β-D-glucoside' and MIBiG calls it 'dhurrin'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.

Provenance

Source concept	Source	Version
BGC0000798	MIBIG	3
CHEBI:27826	CHEBI	3-star

This page is generated from data/natural_products/amino_acids_and_peptides/s-4-hydroxymandelonitrile-d-glucoside.yaml, which is generated from the committed inventories. Neither is edited by hand.