5-Hydroxymethylfurfural

Details

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Internal ID 20a3d0a3-1246-48e5-9034-7e5dc30f670c
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Aldehydes > Aryl-aldehydes
IUPAC Name 5-(hydroxymethyl)furan-2-carbaldehyde
SMILES (Canonical) C1=C(OC(=C1)C=O)CO
SMILES (Isomeric) C1=C(OC(=C1)C=O)CO
InChI InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
InChI Key NOEGNKMFWQHSLB-UHFFFAOYSA-N
Popularity 4,595 references in papers

Physical and Chemical Properties

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Molecular Formula C6H6O3
Molecular Weight 126.11 g/mol
Exact Mass 126.031694049 g/mol
Topological Polar Surface Area (TPSA) 50.40 Ų
XlogP -0.60
Atomic LogP (AlogP) 0.58
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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67-47-0
5-Hydroxymethyl-2-furaldehyde
5-(hydroxymethyl)furan-2-carbaldehyde
5-(Hydroxymethyl)furfural
5-(Hydroxymethyl)-2-furaldehyde
Hydroxymethylfurfural
5-(Hydroxymethyl)-2-furfural
5-Oxymethylfurfurole
5-Hydroxymethylfuraldehyde
Hydroxymethylfurfurole
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of 5-Hydroxymethylfurfural

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9871 98.71%
Caco-2 + 0.6983 69.83%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability + 0.6000 60.00%
Subcellular localzation Mitochondria 0.7748 77.48%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8764 87.64%
OATP1B3 inhibitior + 0.9509 95.09%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.9598 95.98%
P-glycoprotein inhibitior - 0.9839 98.39%
P-glycoprotein substrate - 0.9797 97.97%
CYP3A4 substrate - 0.7593 75.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7912 79.12%
CYP3A4 inhibition - 0.9846 98.46%
CYP2C9 inhibition - 0.8827 88.27%
CYP2C19 inhibition - 0.7928 79.28%
CYP2D6 inhibition - 0.9693 96.93%
CYP1A2 inhibition - 0.5499 54.99%
CYP2C8 inhibition - 0.9550 95.50%
CYP inhibitory promiscuity - 0.8325 83.25%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.8217 82.17%
Carcinogenicity (trinary) Danger 0.4707 47.07%
Eye corrosion + 0.7124 71.24%
Eye irritation + 0.9899 98.99%
Skin irritation + 0.7445 74.45%
Skin corrosion + 0.7125 71.25%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8360 83.60%
Micronuclear - 0.7341 73.41%
Hepatotoxicity + 0.6826 68.26%
skin sensitisation + 0.5893 58.93%
Respiratory toxicity - 0.5667 56.67%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity + 0.5348 53.48%
Acute Oral Toxicity (c) III 0.7997 79.97%
Estrogen receptor binding - 0.8682 86.82%
Androgen receptor binding - 0.8656 86.56%
Thyroid receptor binding - 0.8717 87.17%
Glucocorticoid receptor binding - 0.7919 79.19%
Aromatase binding - 0.7830 78.30%
PPAR gamma - 0.7166 71.66%
Honey bee toxicity - 0.9631 96.31%
Biodegradation + 0.6250 62.50%
Crustacea aquatic toxicity - 0.7400 74.00%
Fish aquatic toxicity - 0.9188 91.88%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL3577 P00352 Aldehyde dehydrogenase 1A1 39810.7 nM
Potency
via CMAUP
CHEMBL1963 P16473 Thyroid stimulating hormone receptor 7943.3 nM
7943.3 nM
Potency
Potency
via CMAUP
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.07% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 86.80% 91.11%
CHEMBL3401 O75469 Pregnane X receptor 82.19% 94.73%
CHEMBL3492 P49721 Proteasome Macropain subunit 81.70% 90.24%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 80.61% 89.67%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Achyranthes bidentata
Acorus calamus
Acorus calamus var. angustatus
Acorus gramineus
Albizia julibrissin
Allium cepa
Anemarrhena asphodeloides
Aralia bipinnata
Aristolochia gehrtii
Aristolochia kaempferi
Asparagus cochinchinensis
Atractylodes lancea
Aucklandia costus
Carthamus tinctorius
Cassia fistula
Chaenomeles sinensis
Chamaecyparis pisifera
Citrus × aurantium
Cleistopholis glauca
Clematis chinensis
Clerodendrum trichotomum
Clivia miniata
Codonopsis pilosula
Cornus officinalis
Crocus sativus
Curculigo orchioides
Dendrobium chrysanthum
Dendrobium chrysotoxum
Dendrobium fimbriatum
Dendrobium loddigesii
Dendrobium moniliforme
Dendrobium nobile
Dioscorea japonica
Dioscorea oppositifolia
Dioscorea polystachya
Dorstenia excentrica
Duhaldea cappa
Eleutherococcus senticosus
Equisetum ramosissimum subsp. debile
Eucommia ulmoides
Euphorbia hirta
Garcinia subelliptica
Gastrodia elata
Gonocaryum calleryanum
Gymnadenia conopsea
Heptapleurum divaricatum
Hippophae rhamnoides
Homalomena occulta
Hydrastis canadensis
Hymenoxys ambigens var. floribunda
Hyoscyamus niger
Imperata cylindrica
Isatis tinctoria
Jatropha curcas
Liquidambar orientalis
Liriope muscari
Lobelia chinensis
Lycium barbarum
Lycium chinense
Ophiopogon japonicus
Peperomia blanda
Pinellia ternata
Pogostemon cablin
Polygonatum cyrtonema
Polygonatum falcatum
Polygonatum kingianum
Polygonatum sibiricum
Polygonum perfoliatum
Prunus mume
Ranunculus ternatus
Rehmannia glutinosa
Rhododendron dauricum
Saussurea cordifolia
Schisandra chinensis
Scrophularia buergeriana
Scrophularia ningpoensis
Scrophularia nodosa
Siphoneugena densiflora
Stellaria dichotoma
Tabebuia angustata
Tithonia rotundifolia
Trichosanthes bracteata
Trichosanthes kirilowii
Trichosanthes rosthornii
Vitis vinifera
Wurfbainia neoaurantiaca
Xanthium strumarium

Cross-Links

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PubChem 237332
NPASS NPC107482
ChEMBL CHEMBL185885
LOTUS LTS0233269
wikiData Q414606