Pyridoxine

Details

• Internal ID: c1fd5822-6f16-4bba-a911-ae69bd7c7e5a
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyridoxines
• IUPAC Name: 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
• SMILES (Canonical): CC1=NC=C(C(=C1O)CO)CO
• SMILES (Isomeric): CC1=NC=C(C(=C1O)CO)CO
• InChI: InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
• InChI Key: LXNHXLLTXMVWPM-UHFFFAOYSA-N
• Popularity: 25,947 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₁NO₃
• Molecular Weight: 169.18 g/mol
• Exact Mass: 169.07389321 g/mol
• Topological Polar Surface Area (TPSA): 73.60 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 65-23-6
• vitamin B6
• Pyridoxol
• Pyridoxin
• Gravidox
• 3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine
• Adermine
• Hydoxin
• Pyridoxolum
• 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-
• 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
• 5-Hydroxy-6-methyl-3,4-pyridinedimethanol
• Pyridoxinum
• Piridossina
• Piridoxina
• Piridossina [DCIT]
• 3-Hydroxy-4,5-dimethylol-alpha-picoline
• Pyridoxinum [INN-Latin]
• Piridoxina [INN-Spanish]
• Hexabione
• 12001-77-3
• 2-Picoline-4,5-dimethanol, 3-hydroxy-
• Pyridoxine [INN:BAN]
• (5-Hydroxy-6-methylpyridine-3,4-diyl)dimethanol
• 2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine
• Vitamin V6
• 2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine
• 2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine
• CHEBI:16709
• Vitaped
• EINECS 200-603-0
• Adermin
• Bezatin
• Pirivitol
• 4,5-bis(hydroxymethyl)-2-methyl-pyridin-3-ol
• UNII-KV2JZ1BI6Z
• KV2JZ1BI6Z
• VitaminB6
• Infuvite Pediatric
• Pyridoxin hydrochloride
• vitamin B-6
• 2-methyl-3-hydroxy-4,5-dihydroxymethylpyridine
• NSC-759148
• DTXSID4023541
• Pyridoxine free base
• Pyridoxine (Vit B6)
• 2-Methyl-3-hydroxy-4,5-dihydroxymethyl-pyridin [German]
• 4,5-Bis(hydroxymethyl)-2-methyl-3-pyridinol
• Cernevit-12
• Prestwick0_000623
• Prestwick1_000623
• Prestwick2_000623
• Prestwick3_000623
• 2-Methyl-3-hydroxy-4,5-dihydroxymethyl-pyridin
• M.V.I.-12 Lyophilized
• TimTec1_000657
• Oprea1_061614
• BSPBio_000586
• CBDivE_015627
• SPBio_002805
• DTXCID903541
• BPBio1_000646
• Pyridoxine (INN)
• M.V.I.-12
• STK177324
• 65-23-6 (FREE BASE)
• 2-methyl-3-hydroxy-4,5-bis(hydroxy-methyl) pyridine
• 3-hydroxy-2-Picoline-4,5-dimethanol
• NSC 759148
• DB00165
• CAS-58-56-0
• SMP2_000230
• NCGC00016261-01
• NCGC00016261-03
• LS-134393
• PYRIDOXINE [INN]
• C00314
• AC-907/25014218
• PN
• Vitamin B6, hydrochloride
• CAS-65-23-6
• AIDS006784
• AIDS-006784
• NSC36225
• 2-methyl-4,5-dimethylol-pyridin-3-ol
• SR-05000001644
• NCGC00164317-01
• 58-56-0 (HCL)
• pyridoxina
• 4,5-bis(hydroxymethyl)-2-methylpyridine-3-ol
• Pridoxine
• vitaminum b6
• 5-[Dideuterio(hydroxy)methyl]-4-(hydroxymethyl)-2-methylpyridin-3-ol
• Beesix (Salt/Mix)
• nchembio.93-comp1
• TRIDMAC
• Becilan (Salt/Mix)
• Benadon (Salt/Mix)
• Hexobion (Salt/Mix)
• Vitamin B6 (TN)
• Pyridoxol; Vitamin B6
• Pyridoxine, >=98%
• Hexabetalin (Salt/Mix)
• PYRIDOXINE [MI]
• Vitamin b6,hydrochloride
• PYRIDOXINE [INCI]
• PYRIDOXINE [VANDF]
• bmse000288
• D0X8HP
• SCHEMBL3506
• CHEMBL1364
• PYRIDOXINE [WHO-DD]
• BIDD:PXR0180
• VITAMIN B6 [VANDF]
• P5669_SIGMA
• PYRIDOXINE [ORANGE BOOK]
• A11HA02
• NSC36225 (HCL)
• Pyridoxol, Vitamin B6, Gravidox
• HMS2093L07
• KUC106691N
• Pharmakon1600-01505453
• BCP27975
• HY-B1328
• Tox21_113644
• Tox21_300365
• BBL005552
• BDBM50103505
• c1302
• MFCD00006335
• NSC759148
• s3980
• ZINC00049154
• AKOS005410791
• Tox21_113644_1
• CCG-213453
• CS-O-02556
• CS-W019950
• Vitamin B6 100 microg/mL in Methanol
• NCGC00016261-02
• NCGC00016261-04
• NCGC00016261-05
• NCGC00016261-08
• NCGC00164317-02
• NCGC00254340-01
• AC-14512
• DS-11013
• KSC-11-207-23
• SBI-0206844.P001
• 3,4-piridindimetanol, 5-hidroxi-6-metil-
• 3-Hydroxy-4,5-dimethylol-.alpha.-picoline
• AM20070169
• FT-0631288
• FT-0674200
• EN300-39851
• D08454
• O10129
• 4,5-Bis(hydroxymethyl)-2-methyl-3-pyridinol #
• A835033
• Q423746
• Q-201646
• SR-05000001644-1
• SR-05000001644-3
• 2-Methyl-3-oxylato-4,5-bis(hydroxymethyl)pyridinium
• 2B3E07D2-E4CC-4CC5-B085-6070BA01F9F0
• Z382721012
• 2-methyl-3-hydroxy-4-hydroxymethyl-5-hydroxymethyl pyridine
• InChI=1/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9156	91.56%
Caco-2	-	0.7490	74.90%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7589	75.89%
OATP2B1 inhibitior	-	0.8505	85.05%
OATP1B1 inhibitior	+	0.8323	83.23%
OATP1B3 inhibitior	+	0.9501	95.01%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9078	90.78%
P-glycoprotein inhibitior	-	0.9710	97.10%
P-glycoprotein substrate	-	0.9503	95.03%
CYP3A4 substrate	-	0.6196	61.96%
CYP2C9 substrate	-	0.8191	81.91%
CYP2D6 substrate	-	0.8363	83.63%
CYP3A4 inhibition	-	0.8648	86.48%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8410	84.10%
CYP inhibitory promiscuity	-	0.6950	69.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6568	65.68%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8406	84.06%
Skin irritation	-	0.7668	76.68%
Skin corrosion	-	0.9005	90.05%
Ames mutagenesis	+	0.5078	50.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.8342	83.42%
skin sensitisation	-	0.7041	70.41%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.8153	81.53%
Estrogen receptor binding	-	0.8023	80.23%
Androgen receptor binding	-	0.8265	82.65%
Thyroid receptor binding	-	0.8474	84.74%
Glucocorticoid receptor binding	-	0.8034	80.34%
Aromatase binding	-	0.7640	76.40%
PPAR gamma	-	0.6714	67.14%
Honey bee toxicity	-	0.9707	97.07%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.8787	87.87%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14321.7 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	15848.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	89.45%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.80%	91.11%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.34%	93.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.45%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.06%	97.36%
CHEMBL1937	Q92769	Histone deacetylase 2	80.86%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.48%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.15%	90.08%

Plants that contains it

• Albizia julibrissin
• Allium sativum
• Anacardium occidentale
• Anchusa officinalis
• Arabidopsis thaliana
• Caryopteris mongholica
• Dalbergia rubiginosa
• Euphorbia kansui
• Hippophae rhamnoides
• Illicium verum
• Mappia nimmoniana
• Mesembryanthemum tortuosum
• Rubia cordifolia
• Satureja atropatana
• Theobroma cacao
• Zea mays

Cross-Links

• PubChem: 1054
• NPASS: NPC269919
• ChEMBL: CHEMBL1364
• LOTUS: LTS0130302
• wikiData: Q423746