Biotin

Details

• Internal ID: 59aa7112-e826-411f-b4bb-768db441d5bd
• Taxonomy: Organoheterocyclic compounds > Biotin and derivatives
• IUPAC Name: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
• SMILES (Canonical): C1C2C(C(S1)CCCCC(=O)O)NC(=O)N2
• SMILES (Isomeric): C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)O)NC(=O)N2
• InChI: InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
• InChI Key: YBJHBAHKTGYVGT-ZKWXMUAHSA-N
• Popularity: 53,576 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆N₂O₃S
• Molecular Weight: 244.31 g/mol
• Exact Mass: 244.08816355 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• d-biotin
• 58-85-5
• vitamin H
• Vitamin B7
• coenzyme R
• Bioepiderm
• Bios II
• Factor S
• D(+)-Biotin
• D-(+)-Biotin
• Biodermatin
• (+)-Biotin
• Medebiotin
• Biotine
• Biotinum
• Factor S (vitamin)
• Injacom H
• Biotina
• Meribin
• beta-Biotin
• Vitamin Bw
• Lutavit H2
• Ritatin
• NSC 63865
• CCRIS 3932
• HSDB 346
• 3H-Biotin
• cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid
• cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid
• MFCD00005541
• Biotine [INN-French]
• Biotinum [INN-Latin]
• Biotina [INN-Spanish]
• 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid
• AI3-51198
• 1swk
• 1swn
• 1swr
• EINECS 200-399-3
• Rovimix H 2
• D-Biotin Factor S
• UNII-6SO6U10H04
• 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
• 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
• CHEBI:15956
• 6SO6U10H04
• 1H-Thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, (3aS-(3aalpha,4beta,6aalpha))-
• 2'-Keto-3,4-imidazolido-2-tetrahydrothiophene-N-valeric acid
• NSC-63865
• Biotin [USP:INN:JAN]
• cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid
• (+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid
• Biotin [USAN:INN:JAN]
• MD-1003
• (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-valeric acid
• Hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanoic acid, (3aS-(3aalpha,4beta,6aalpha))-
• DTXCID102679
• DTXSID7022679
• L-Biotin
• (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid
• 1H-thieno[3,4-d]imidazole-4-pentanoic acid, hexahydro-2-oxo-, (3aS,4S,6aR)-
• 5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
• D-Biotin 10 microg/mL in Acetonitrile
• Hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanoic acid
• BIOTIN (MART.)
• BIOTIN [MART.]
• (3aS-(3aalpha,4b,6aalpha))-Hexahydro-2-oxo-1H-thieno(3,4-d)imidaz- ole-4-pentanoic acid
• 1H-Thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, (3aS-(3aalpha,4b,6aalpha))-
• BIOTIN (EP IMPURITY)
• BIOTIN [EP IMPURITY]
• BIOTIN (EP MONOGRAPH)
• BIOTIN [EP MONOGRAPH]
• BIOTIN (USP MONOGRAPH)
• BIOTIN [USP MONOGRAPH]
• medobiotin
• Deacura
• Gabunat
• Rombellin
• Biokur
• Biotin Gelfert
• Biotin Hermes
• Biotine Roche
• Biotin Forte
• Gelfert, Biotin
• Biotin ratiopharm
• Biotin-ratiopharm
• Hermes, Biotin
• Roche, Biotine
• 22377-59-9
• 1H-Thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, (3aS,4S,6aR)-
• 5-((3AS,4S,6aR)-rel-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid
• Rovimix H2
• Biotin (Vitamin B7)
• 56846-45-8
• SMR000112255
• D(+)Biotin
• 5-(2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid
• cis-(+)-Tetrahydro-2-oxothieno(3,4)imidazoline-4-valeric acid
• cis-tetrahydro-2-oxothieno[3,4-d]imidazoline-4-valeric acid
• hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid
• NSC63865
• delta-Biotin
• (+)-cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid
• Vitamin-h
• 1avd
• 1ndj
• 1stp
• 1swg
• 1swp
• 2avi
• 4bcs
• 4ggz
• 4jnj
• 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno(3,4-d)imidazol-4-yl)pentanoic acid
• Bioepiderm (TN)
• CAS-58-85-5
• Bios H
• NCGC00094984-04
• 1H-Thieno[3,4-d]imidazole-4-pentanoic acid, hexahydro-2-oxo-, [3as-(3aalpha,4beta,6aalpha)]-
• Biotin111In
• delta-(+)-Biotin
• Biotin (8CI)
• delta-biotin factor s
• 1df8
• 1n9m
• 2gh7
• 3t2w
• 4bj8
• BIOTIN [VANDF]
• BIOTIN [HSDB]
• BIOTIN [INCI]
• BIOTIN [FCC]
• BIOTIN [INN]
• BIOTIN [JAN]
• BIOTIN [USP-RS]
• BIOTIN [WHO-DD]
• Prestwick0_000418
• Prestwick1_000418
• Prestwick2_000418
• Prestwick3_000418
• BIOTIN [MI]
• cid_253
• D-BIOTIN [VANDF]
• BDBM12
• bmse000227
• CHEMBL857
• D0P8TJ
• Probes2_000006
• SCHEMBL8763
• BIOTIN [ORANGE BOOK]
• Biotin for system suitability
• BSPBio_000376
• Biotin (JP17/USP/INN)
• MLS001066402
• MLS001074888
• MLS001331736
• MLS001333089
• D-Biotin, analytical standard
• SPBio_002315
• 5-(2-oxohexahydro-1H-thieno(3,4-d)imidazol-4-yl)pentanoic acid
• BPBio1_000414
• cid_171548
• GTPL4787
• A11HA05
• AMF0005
• 1n43
• 2f01
• Biotin, >=99.0% (T)
• YBJHBAHKTGYVGT-ZKWXMUAHSA-N
• CIS-TETRAHYDRO-2-OXOTHIENO
• HMS1569C18
• HMS2096C18
• HMS2271O06
• HMS3713C18
• HY-B0511
• Tox21_113050
• Tox21_302161
• AC8089
• BBL028095
• Biotin, tested according to Ph.Eur.
• s3130
• STK801941
• AKOS001287669
• Tox21_113050_1
• CCG-220418
• CIS-HEXAHYDRO-2-OXO-1H-THIENO
• CS-P-00358
• DB00121
• LS-3171
• Biotin, meets USP testing specifications
• Biotin, SAJ special grade, >=98.0%
• NCGC00179580-01
• NCGC00179580-02
• NCGC00179580-04
• NCGC00255377-01
• AC-19998
• BP-20441
• Biotin, >=99% (TLC), lyophilized powder
• Biotin, Vetec(TM) reagent grade, >=99%
• AB00374191
• B0463
• EN300-54173
• C00120
• D00029
• M02926
• AB00374191-08
• AB00374191_11
• A929752
• Biotin, plant cell culture tested, >=99% (TLC)
• Q181354
• SR-01000765521
• Biotin, certified reference material, TraceCERT(R)
• Q-200929
• SR-01000765521-2
• BRD-K89210380-001-03-8
• BRD-K89210380-001-13-7
• 6AE43AA3-BC3D-4C49-9DB9-5913A2401EB6
• Biotin, European Pharmacopoeia (EP) Reference Standard
• F2173-0855
• Hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanoate
• Z210803762
• Biotin, United States Pharmacopeia (USP) Reference Standard
• cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valerate
• (+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valerate
• 5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate
• 2-KETO-3,4-IMIDAZOLIDO-2-TETRAHYDROTHIOPHENE-N-VALERIC ACID
• 5-(3-oxo-7-thia-2,4-diazabicyclo(3.3.0)oct-8-yl)pentanoic acid
• CIS-HEXAHYDRO-2-OXOTHIENO(3,4-D)IMIDAZOLE-4-VALERIC ACID
• Daunorubicin hydrochloride, Antibiotic for Culture Media Use Only
• (+)-CIS-HEXAHYDRO-2-KETO-1H-THIENO-(3,4)-IMIDAZOLE-4-VALERIC ACID
• (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid
• (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-valerate
• 2'-KETO-3,4-IMIDAZOLIDO-2-TETRAHYDROTHIOPHENE-DELTA-N-VALERIC ACID
• Biotin, Pharmaceutical Secondary Standard; Certified Reference Material
• (3aS-(3aalpha,4b,6aalpha))-Hexahydro-2-oxo-1H-thieno(3,4-d)imidaz-ole-4-pentanoic acid
• 1H-Thieno[3,4-d]imidazole-4-pentanoic acid, hexahydro-2-oxo-, (3aS,4S,6aR)- (9CI)
• 5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid
• 5-[(3aR,6S,6aS)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanoic acid
• Biotin for system suitability, European Pharmacopoeia (EP) Reference Standard
• hexahydro-2-oxo-[3aS-(3aa,4b,6aa)]-1H-Thieno[3,4-d]imidazole-4-pentanoate
• hexahydro-2-oxo-[3aS-(3aa,4b,6aa)]-1H-Thieno[3,4-d]imidazole-4-pentanoic acid
• hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-Thieno[3,4-d]imidazole-4-pentanoate
• hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-Thieno[3,4-d]imidazole-4-pentanoic acid
• (3AS-(3A(ALPHA),4B,6A(ALPHA)))-HEXAHYDRO-2-OXO-1H-THIENO(3,4-D)IMIDAZOLE-4-PENTANOIC ACID
• 1H-THIENO(3,4-D)IMIDAZOLE-4-PENTANOIC ACID, HEXAHYDRO-2-OXO-,(3AS-(3A(ALPHA),4B,6A(ALPHA)))-
• 1H-THIENO(3,4-D)IMIDAZOLE-4-PENTANOIC ACID, HEXAHYDRO-2-OXO-,(3AS-(3A(ALPHA),4BETA,6A(ALPHA)))-
• Biotin, powder, BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture, >=99%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9610	96.10%
Caco-2	-	0.8744	87.44%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7672	76.72%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.9441	94.41%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8932	89.32%
P-glycoprotein inhibitior	-	0.9428	94.28%
P-glycoprotein substrate	-	0.8411	84.11%
CYP3A4 substrate	-	0.5864	58.64%
CYP2C9 substrate	+	0.6124	61.24%
CYP2D6 substrate	-	0.8281	82.81%
CYP3A4 inhibition	-	0.8959	89.59%
CYP2C9 inhibition	-	0.9252	92.52%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9324	93.24%
CYP inhibitory promiscuity	-	0.9762	97.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6441	64.41%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.9708	97.08%
Skin irritation	-	0.8030	80.30%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6237	62.37%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.5531	55.31%
skin sensitisation	-	0.8810	88.10%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7077	70.77%
Acute Oral Toxicity (c)	III	0.6733	67.33%
Estrogen receptor binding	+	0.5473	54.73%
Androgen receptor binding	-	0.7884	78.84%
Thyroid receptor binding	-	0.6791	67.91%
Glucocorticoid receptor binding	-	0.6133	61.33%
Aromatase binding	-	0.5716	57.16%
PPAR gamma	-	0.5422	54.22%
Honey bee toxicity	-	0.9538	95.38%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.4610	46.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293287	P14735	Insulin-degrading enzyme	2373 nM; 2526 nM	EC50; EC50	via CMAUP; via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	354.8 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	10 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	5 nM; 12.6 nM; 4.5 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.31%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.74%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.14%	91.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.70%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.49%	99.17%
CHEMBL4374	Q9Y5X4	Photoreceptor-specific nuclear receptor	85.01%	85.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.84%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.59%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.93%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.36%	97.09%

Plants that contains it

• Alstonia muelleriana
• Coreopsis nodosa
• Dacrydium cupressinum
• Glycine tomentella
• Nicotiana undulata
• Passiflora incarnata
• Senecio paludaffinis
• Seriphidium cinum
• Trigonella grandiflora
• Tripolium pannonicum
• Uvaria calamistrata

Cross-Links

• PubChem: 171548
• NPASS: NPC199072
• ChEMBL: CHEMBL857
• LOTUS: LTS0119062
• wikiData: Q181354