Divanillin

Details

• Internal ID: f7a35be7-8a04-4bf1-a87a-34b686557f2e
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Biphenyls and derivatives
• IUPAC Name: 3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde
• InChI: InChI=1S/C16H14O6/c1-21-13-5-9(7-17)3-11(15(13)19)12-4-10(8-18)6-14(22-2)16(12)20/h3-8,19-20H,1-2H3
• InChI Key: NSTQUZVZBUTVPY-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.41
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Divanillin
• Dehydrodivanillin
• 5,5'-Bivanillin
• 3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde
• [1,1'-Biphenyl]-3,3'-dicarboxaldehyde, 6,6'-dihydroxy-5,5'-dimethoxy-
• 29PYY1H4BT
• NSC-16723
• FEMA NO. 4107
• 3,3'-Biphenyldicarboxaldehyde, 6,6'-dihydroxy-5,5'-dimethoxy-
• DTXSID30862830
• (1,1'-Biphenyl)-3,3'-dicarboxaldehyde, 6,6'-dihydroxy-5,5'-dimethoxy-
• RefChem:589868
• DTXCID50811547
• 6,6'-Dihydroxy-5,5'-dimethoxybiphenyl-3,3'-dicarbaldehyde
• MFCD00156888
• Dehydrovanillin
• Dehydrodivanillin (~90%, contains up to 10% unknown inorganics)
• 5,5-Bisvanillin
• 5,5'-Bivanillin; 5,5'-Diformyl-3,3'-dimethoxy-1,1'-biphenyl-2,2'-diol; Divanillin; NSC 16723; 6,6'-Dihydroxy-5,5'-dimethoxy[1,1'-biphenyl]-3,3'-dicarboxaldehyde; 6,6'-Dihydroxy-5,5'-dimethoxy[1,1'-biphenyl]-3,3'-dicarboxaldehyde
• DIVANILLIN [FHFI]
• bmse010019
• UNII-29PYY1H4BT
• CHEMBL41304
• SCHEMBL1487492
• SCHEMBL29371792
• ALBB-025820
• EX-A4901
• NSC16723
• NSC 16723
• SBB071517
• AKOS015889366
• FD71561
• WT81732
• 3, 6,6'-dihydroxy-5,5'-dimethoxy-
• s11876
• DS-10405
• SY225363
• DS-013888
• CS-0150461
• NS00123868
• F375165
• 2,2'-dihydroxy-3,3'-dimethoxy-5,5'-diformylbiphenyl
• Q27254436
• [1,3'-dicarboxaldehyde, 6,6'-dihydroxy-5,5'-dimethoxy-
• 6,6'-Dihydroxy-5,5'-dimethoxy-biphenyl-3,3'-dicarbaldehyde
• 3,3-Biphenyldicarboxaldehyde, 6,6-dihydroxy-5,5-dimethoxy-(8ci)
• 5,5'-DIFORMYL-3,3'-DIMETHOXY-1,1'-BIPHENYL-2,2'-DIOL
• 3-(3-formyl-6-hydroxy-5-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde
• 3-(5-formyl-2-hydroxy-3-methoxy-phenyl)-4-hydroxy-5-methoxy-benzaldehyde
• 6,6'-Dihydroxy-5,5'-dimethoxy- [1,1'-biphenyl]-3,3'-dicarboxaldehyde
• 6,6'-Dihydroxy-5,5'-dimethoxy[1,1'-biphenyl]-3,3'-dicarbaldehyde #
• 4-hydroxy-3-(2-hydroxy-5-methanoyl-3-methoxy-phenyl)-5-methoxy-benzaldehyde
• 6,6'-DIHYDROXY-5,5'-DIMETHOXY-[1,1'-BIPHENYL]-3,3'-DICARBALDEHYDE
• 6,6 inverted exclamation mark -Dihydroxy-5,5 inverted exclamation mark -dimethoxybiphenyl-3,3 inverted exclamation mark -dicarbaldehyde

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	+	0.5662	56.62%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.9367	93.67%
OATP2B1 inhibitior	-	0.5759	57.59%
OATP1B1 inhibitior	+	0.7689	76.89%
OATP1B3 inhibitior	+	0.8532	85.32%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5414	54.14%
P-glycoprotein inhibitior	-	0.6117	61.17%
P-glycoprotein substrate	-	0.9344	93.44%
CYP3A4 substrate	-	0.6176	61.76%
CYP2C9 substrate	-	0.6165	61.65%
CYP2D6 substrate	-	0.6929	69.29%
CYP3A4 inhibition	-	0.8634	86.34%
CYP2C9 inhibition	+	0.6647	66.47%
CYP2C19 inhibition	+	0.7685	76.85%
CYP2D6 inhibition	-	0.8021	80.21%
CYP1A2 inhibition	+	0.7116	71.16%
CYP2C8 inhibition	-	0.7152	71.52%
CYP inhibitory promiscuity	-	0.5450	54.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7345	73.45%
Carcinogenicity (trinary)	Non-required	0.5894	58.94%
Eye corrosion	-	0.9714	97.14%
Eye irritation	+	0.8231	82.31%
Skin irritation	-	0.7394	73.94%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5746	57.46%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.7034	70.34%
skin sensitisation	-	0.9375	93.75%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.5750	57.50%
Acute Oral Toxicity (c)	III	0.7451	74.51%
Estrogen receptor binding	+	0.7540	75.40%
Androgen receptor binding	-	0.5181	51.81%
Thyroid receptor binding	+	0.5441	54.41%
Glucocorticoid receptor binding	+	0.7690	76.90%
Aromatase binding	+	0.6039	60.39%
PPAR gamma	+	0.5302	53.02%
Honey bee toxicity	-	0.9019	90.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.9827	98.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	97.18%	98.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.30%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.52%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.13%	86.33%
CHEMBL3194	P02766	Transthyretin	87.89%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.80%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.13%	96.00%
CHEMBL4208	P20618	Proteasome component C5	84.83%	90.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.03%	90.24%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.14%	95.50%
CHEMBL2581	P07339	Cathepsin D	82.77%	98.95%
CHEMBL2535	P11166	Glucose transporter	81.15%	98.75%

Plants that contains it

• Styrax benzoin

Cross-Links

• PubChem: 95086
• NPASS: NPC275278