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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:29:40 UTC

Update Date

2022-09-22 17:44:21 UTC

HMDB ID

HMDB0249700

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Castanospermine

Description

octahydroindolizine-1,6,7,8-tetrol belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. octahydroindolizine-1,6,7,8-tetrol is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Castanospermine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Castanospermine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.590  -0.533   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0249700
HETATM    1  O1  UNL     1       2.589  -1.488  -0.742  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.077  -0.571   0.174  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.874  -1.180   0.813  1.00  0.00           C  
HETATM    4  N1  UNL     1      -0.302  -1.128  -0.023  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.412  -1.631   0.761  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.607  -0.790   0.282  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.888   0.566   0.245  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.619   1.537  -0.366  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.635   0.166  -0.497  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.391   1.213  -0.336  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.184   2.202  -1.325  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.808   0.752  -0.480  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.622   1.731   0.123  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.510  -1.201  -1.004  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.859  -0.463   0.974  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.651  -0.679   1.767  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.091  -2.257   1.001  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.588  -2.696   0.663  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.265  -1.296   1.830  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.835  -1.155  -0.730  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.433  -0.805   0.987  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.625   0.819   1.268  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.663   1.499  -1.334  1.00  0.00           H  
HETATM   24  H11 UNL     1      -0.876   0.080  -1.595  1.00  0.00           H  
HETATM   25  H12 UNL     1       0.244   1.717   0.641  1.00  0.00           H  
HETATM   26  H13 UNL     1       0.635   1.955  -2.177  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.117   0.712  -1.547  1.00  0.00           H  
HETATM   28  H15 UNL     1       2.097   2.390   0.629  1.00  0.00           H  
CONECT    1    2   14
CONECT    2    3   12   15
CONECT    3    4   16   17
CONECT    4    5    9
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23
CONECT    9   10   24
CONECT   10   11   12   25
CONECT   11   26
CONECT   12   13   27
CONECT   13   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₈H₁₅NO₄

Average Molecular Weight

189.211

Monoisotopic Molecular Weight

189.100107967

IUPAC Name

octahydroindolizine-1,6,7,8-tetrol

Traditional Name

octahydroindolizine-1,6,7,8-tetrol

CAS Registry Number

Not Available

SMILES

OC1CCN2CC(O)C(O)C(O)C12

InChI Identifier

InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2

InChI Key

JDVVGAQPNNXQDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indolizidine
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Azacycle
Polyol
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxygen compound
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: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0249700)

Food

Vegetable

Castanospermum australe (FooDB: FOOD00893)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	-2.1	ALOGPS
logP	-2.6	ChemAxon
logS	0.77	ALOGPS
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	84.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.44 m³·mol⁻¹	ChemAxon
Polarizability	18.76 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
DeepCCS	[M-2H]-	175.261	30932474
DeepCCS	[M+Na]+	150.705	30932474
AllCCS	[M+H]+	144.1	32859911
AllCCS	[M+H-H2O]+	139.8	32859911
AllCCS	[M+NH4]+	148.0	32859911
AllCCS	[M+Na]+	149.2	32859911
AllCCS	[M-H]-	139.8	32859911
AllCCS	[M+Na-2H]-	140.2	32859911
AllCCS	[M+HCOO]-	140.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Castanospermine	OC1CCN2CC(O)C(O)C(O)C12	3401.1	Standard polar	33892256
Castanospermine	OC1CCN2CC(O)C(O)C(O)C12	1828.2	Standard non polar	33892256
Castanospermine	OC1CCN2CC(O)C(O)C(O)C12	1876.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i0-3900000000-97562f86dd3c439569b6	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Castanospermine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	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 - Castanospermine 10V, Negative-QTOF	splash10-000i-0900000000-8cea129c547fc7be9b08	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Castanospermine 20V, Negative-QTOF	splash10-000i-0900000000-bd569d28f24bc0e3fe04	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Castanospermine 40V, Negative-QTOF	splash10-052o-9300000000-ff90227c9e83a5e77b4f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Castanospermine 10V, Positive-QTOF	splash10-0006-0900000000-59fdcb6f9006a2fc90c6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Castanospermine 20V, Positive-QTOF	splash10-0f6x-0900000000-1b025ae08e2bcb84221a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Castanospermine 40V, Positive-QTOF	splash10-01qa-9600000000-29d672ade51bf8f0d242	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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 but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2592

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Castanospermine (HMDB0249700)

MOL for HMDB0249700 (Castanospermine)

3D MOL for HMDB0249700 (Castanospermine)

3D SDF for HMDB0249700 (Castanospermine)

3D-SDF for HMDB0249700 (Castanospermine)

PDB for HMDB0249700 (Castanospermine)

3D PDB for HMDB0249700 (Castanospermine)

SMILES for HMDB0249700 (Castanospermine)

INCHI for HMDB0249700 (Castanospermine)

Structure for HMDB0249700 (Castanospermine)

3D Structure for HMDB0249700 (Castanospermine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra