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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-24 13:49:09 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004821

Secondary Accession Numbers

HMDB04821

Metabolite Identification

Common Name

Bisnorbiotin

Description

Bisnorbiotin belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom. Bisnorbiotin has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make bisnorbiotin a potential biomarker for the consumption of these foods. Bisnorbiotin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Bisnorbiotin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231219592D          

 16 17  0  0  1  0            999 V2000
   22.4323  -19.7753    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.0780  -17.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7196  -16.7587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0754  -19.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3854  -19.1079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3854  -20.4428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2070  -18.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0143  -18.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9508  -19.1114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.1700  -19.3628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.1700  -20.1879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.9508  -20.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2707  -17.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9004  -19.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1709  -18.7028    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.1709  -20.8479    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3 13  2  0  0  0  0
  4 14  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  6 11  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  9  7  1  6  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  1  0  0  0
 11 12  1  0  0  0  0
 11 16  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0004821

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CS[C@@H](CCC(O)=O)[C@@]1([H])NC(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O3S/c11-6(12)2-1-5-7-4(3-14-5)9-8(13)10-7/h4-5,7H,1-3H2,(H,11,12)(H2,9,10,13)/t4-,5-,7-/m0/s1

> <INCHI_KEY>
QDFGCLSCEPNVQP-VPLCAKHXSA-N

> <FORMULA>
C8H12N2O3S

> <MOLECULAR_WEIGHT>
216.257

> <EXACT_MASS>
216.05686295

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.683997060338108

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]propanoic acid

> <ALOGPS_LOGP>
-0.76

> <JCHEM_LOGP>
-0.5697136819999999

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.384795303408737

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2392109223524885

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8636487382586329

> <JCHEM_POLAR_SURFACE_AREA>
78.42999999999999

> <JCHEM_REFRACTIVITY>
50.8489

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      41.874 -36.914   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      44.946 -32.112   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      42.410 -31.283   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      35.607 -36.914   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      38.053 -35.668   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      38.053 -38.160   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      41.453 -34.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.960 -33.893   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      40.975 -35.675   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      39.517 -36.144   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      39.517 -37.684   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      40.975 -38.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.439 -32.429   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.147 -36.914   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      39.519 -34.912   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0      39.519 -38.916   0.000  0.00  0.00           H+0
CONECT    1    9   12                                                       
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5   10   14                                                       
CONECT    6   11   14                                                       
CONECT    7    8    9                                                       
CONECT    8    7   13                                                       
CONECT    9    1    7   10                                                  
CONECT   10    5    9   11   15                                             
CONECT   11    6   10   12   16                                             
CONECT   12    1   11                                                       
CONECT   13    2    3    8                                                  
CONECT   14    4    5    6                                                  
CONECT   15   10                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
hexahydro-2-oxo-1H-thieno[3,4-D]Imidazole-4-propionic acid	HMDB
[3AS-(3aa,4b,6aa)]-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-propanoate	HMDB
[3AS-(3aa,4b,6aa)]-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-propanoic acid	HMDB
D-Allobisnorbiotin	MeSH, HMDB

Chemical Formula

C₈H₁₂N₂O₃S

Average Molecular Weight

216.257

Monoisotopic Molecular Weight

216.05686295

IUPAC Name

3-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]propanoic acid

Traditional Name

3-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]propanoic acid

CAS Registry Number

16968-98-2

SMILES

[H][C@]12CS[C@@H](CCC(O)=O)[C@@]1([H])NC(=O)N2

InChI Identifier

InChI=1S/C8H12N2O3S/c11-6(12)2-1-5-7-4(3-14-5)9-8(13)10-7/h4-5,7H,1-3H2,(H,11,12)(H2,9,10,13)/t4-,5-,7-/m0/s1

InChI Key

QDFGCLSCEPNVQP-VPLCAKHXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Delta amino acids and derivatives

Alternative Parents

Substituents

Delta amino acid or derivatives
Imidazolyl carboxylic acid derivative
Thia fatty acid
Fatty acyl
2-imidazoline
Thiolane
Isourea
Azacycle
Organoheterocyclic compound
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid
Thioether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9042824)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 9022537)

Source

Endogenous

Endogenous (HMDB: HMDB0004821)

Exogenous

Food

Food (HMDB: HMDB0004821)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0004821)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0004821)

Role

Biological role

Energy source (HMDB: HMDB0004821)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004821)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.19 g/L	ALOGPS
logP	-0.76	ALOGPS
logP	-0.57	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.85 m³·mol⁻¹	ChemAxon
Polarizability	20.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	147.123	31661259
DarkChem	[M-H]-	144.245	31661259
DeepCCS	[M-2H]-	179.515	30932474
DeepCCS	[M+Na]+	154.175	30932474
AllCCS	[M+H]+	146.9	32859911
AllCCS	[M+H-H2O]+	143.1	32859911
AllCCS	[M+NH4]+	150.5	32859911
AllCCS	[M+Na]+	151.6	32859911
AllCCS	[M-H]-	148.1	32859911
AllCCS	[M+Na-2H]-	148.5	32859911
AllCCS	[M+HCOO]-	149.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.75 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5372 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.45 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	198.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	741.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	263.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	58.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	261.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	276.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	755.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	592.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	128.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	902.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	566.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	227.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	356.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisnorbiotin	[H][C@]12CS[C@@H](CCC(O)=O)[C@@]1([H])NC(=O)N2	3660.4	Standard polar	33892256
Bisnorbiotin	[H][C@]12CS[C@@H](CCC(O)=O)[C@@]1([H])NC(=O)N2	1997.4	Standard non polar	33892256
Bisnorbiotin	[H][C@]12CS[C@@H](CCC(O)=O)[C@@]1([H])NC(=O)N2	2396.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bisnorbiotin,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12	2309.7	Semi standard non polar	33892256
Bisnorbiotin,1TMS,isomer #2	C[Si](C)(C)N1C(=O)N[C@H]2CS[C@@H](CCC(=O)O)[C@H]21	2322.3	Semi standard non polar	33892256
Bisnorbiotin,1TMS,isomer #3	C[Si](C)(C)N1C(=O)N[C@@H]2[C@H](CCC(=O)O)SC[C@@H]21	2312.7	Semi standard non polar	33892256
Bisnorbiotin,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C	2358.1	Semi standard non polar	33892256
Bisnorbiotin,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C	2104.9	Standard non polar	33892256
Bisnorbiotin,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C	3962.3	Standard polar	33892256
Bisnorbiotin,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]12	2353.9	Semi standard non polar	33892256
Bisnorbiotin,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]12	2098.1	Standard non polar	33892256
Bisnorbiotin,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]12	4018.7	Standard polar	33892256
Bisnorbiotin,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCC(=O)O)[C@H]21	2258.0	Semi standard non polar	33892256
Bisnorbiotin,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCC(=O)O)[C@H]21	2125.1	Standard non polar	33892256
Bisnorbiotin,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCC(=O)O)[C@H]21	3135.9	Standard polar	33892256
Bisnorbiotin,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2242.3	Semi standard non polar	33892256
Bisnorbiotin,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2191.9	Standard non polar	33892256
Bisnorbiotin,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2809.6	Standard polar	33892256
Bisnorbiotin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12	2539.1	Semi standard non polar	33892256
Bisnorbiotin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)N[C@H]2CS[C@@H](CCC(=O)O)[C@H]21	2548.4	Semi standard non polar	33892256
Bisnorbiotin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N[C@@H]2[C@H](CCC(=O)O)SC[C@@H]21	2537.9	Semi standard non polar	33892256
Bisnorbiotin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C(C)(C)C	2830.9	Semi standard non polar	33892256
Bisnorbiotin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C(C)(C)C	2590.1	Standard non polar	33892256
Bisnorbiotin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C(C)(C)C	3791.4	Standard polar	33892256
Bisnorbiotin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C(C)(C)C)[C@H]12	2836.2	Semi standard non polar	33892256
Bisnorbiotin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C(C)(C)C)[C@H]12	2584.4	Standard non polar	33892256
Bisnorbiotin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C(C)(C)C)[C@H]12	3811.8	Standard polar	33892256
Bisnorbiotin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@H]2CS[C@@H](CCC(=O)O)[C@H]21	2691.1	Semi standard non polar	33892256
Bisnorbiotin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@H]2CS[C@@H](CCC(=O)O)[C@H]21	2635.9	Standard non polar	33892256
Bisnorbiotin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@H]2CS[C@@H](CCC(=O)O)[C@H]21	3038.1	Standard polar	33892256
Bisnorbiotin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2884.0	Semi standard non polar	33892256
Bisnorbiotin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2887.2	Standard non polar	33892256
Bisnorbiotin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2928.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bisnorbiotin GC-MS (Non-derivatized) - 70eV, Positive	splash10-007t-9700000000-2bd417112d9ba4d19b9b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisnorbiotin GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9450000000-114ee328e6abf6e012f1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisnorbiotin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 10V, Positive-QTOF	splash10-014j-0960000000-66d62b7766d3fab9f996	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 20V, Positive-QTOF	splash10-05fs-0910000000-b72e45c69b1cb4c51abd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 40V, Positive-QTOF	splash10-056u-5900000000-30adaeec05ed79809ea6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 10V, Negative-QTOF	splash10-014i-1690000000-2d36ccdf145fa91a20c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 20V, Negative-QTOF	splash10-00xr-5920000000-ba1907a7ca63c233b4dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 40V, Negative-QTOF	splash10-0006-9200000000-a4048ab776be4355c055	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 10V, Negative-QTOF	splash10-014j-0590000000-0e907f5fdae522022b1a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 20V, Negative-QTOF	splash10-014i-2950000000-634041f9273a212af7c7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 40V, Negative-QTOF	splash10-0006-9500000000-93c1247405af3a3caefa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 10V, Positive-QTOF	splash10-014i-0090000000-61427edb75536863523e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 20V, Positive-QTOF	splash10-014i-0590000000-98906be815c33aa34c43	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisnorbiotin 40V, Positive-QTOF	splash10-0002-9700000000-f002a8b7a6c0a5838f53	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00018 (0.00002-0.00059) uM	Adult (>18 years old)	Both	Normal	9042824	details
Blood	Detected and Quantified	0.003 (0.0003-0.0057) uM	Adult (>18 years old)	Both	Normal	9042824	details
Blood	Detected and Quantified	0.0063 (0.0004-0.017) uM	Adult (>18 years old)	Both	Normal	9042824	details
Urine	Detected and Quantified	0.0044 (0.0013-0.0076) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9022537	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023429

KNApSAcK ID

Not Available

Chemspider ID

78006

KEGG Compound ID

C20384

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7083

PubChem Compound

86492

PDB ID

Not Available

ChEBI ID

89481

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zempleni J, McCormick DB, Mock DM: Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-l-sulfoxide in human urine. Am J Clin Nutr. 1997 Feb;65(2):508-11. [PubMed:9022537 ]
Mock DM, Wang KS, Kearns GL: The pig is an appropriate model for human biotin catabolism as judged by the urinary metabolite profile of radioisotope-labeled biotin. J Nutr. 1997 Feb;127(2):365-9. [PubMed:9039841 ]

Showing metabocard for Bisnorbiotin (HMDB0004821)

MOL for HMDB0004821 (Bisnorbiotin)

3D MOL for HMDB0004821 (Bisnorbiotin)

3D SDF for HMDB0004821 (Bisnorbiotin)

3D-SDF for HMDB0004821 (Bisnorbiotin)

PDB for HMDB0004821 (Bisnorbiotin)

3D PDB for HMDB0004821 (Bisnorbiotin)

SMILES for HMDB0004821 (Bisnorbiotin)

INCHI for HMDB0004821 (Bisnorbiotin)

Structure for HMDB0004821 (Bisnorbiotin)

3D Structure for HMDB0004821 (Bisnorbiotin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra