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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:41:49 UTC

Update Date

2021-09-26 22:52:21 UTC

HMDB ID

HMDB0244545

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5,6-Methylenedioxy-2-aminoindane

Description

5,6-Methylenedioxy-2-aminoindane, also known as MDAI, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Based on a literature review a significant number of articles have been published on 5,6-Methylenedioxy-2-aminoindane. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5,6-methylenedioxy-2-aminoindane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5,6-Methylenedioxy-2-aminoindane 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                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       5.329   1.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.329   4.089   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.234   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       7.774   2.843   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1    6    8                                                       
CONECT    2    7    8                                                       
CONECT    3    6    9                                                       
CONECT    4    7   10                                                       
CONECT    5   12   13                                                       
CONECT    6    1    3    7                                                  
CONECT    7    2    4    6                                                  
CONECT    8    1    2   11                                                  
CONECT    9    3   10   12                                                  
CONECT   10    4    9   13                                                  
CONECT   11    8                                                            
CONECT   12    5    9                                                       
CONECT   13    5   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5,6-Methylenedioxy-2-aminoindan	HMDB
MDAI	HMDB
5,6-Methylenedioxy-2-aminoindane	MeSH

Chemical Formula

C₁₀H₁₁NO₂

Average Molecular Weight

177.203

Monoisotopic Molecular Weight

177.078978598

IUPAC Name

2H,5H,6H,7H-indeno[5,6-d][1,3]dioxol-6-amine

Traditional Name

MDAI

CAS Registry Number

Not Available

SMILES

NC1CC2=CC3=C(OCO3)C=C2C1

InChI Identifier

InChI=1S/C10H11NO2/c11-8-1-6-3-9-10(13-5-12-9)4-7(6)2-8/h3-4,8H,1-2,5,11H2

InChI Key

FQDRMHHCWZAXJM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Indane
Aralkylamine
Benzenoid
Acetal
Oxacycle
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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 (PMID: 31557052)

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	0.75	ALOGPS
logP	1.11	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	9.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.03 m³·mol⁻¹	ChemAxon
Polarizability	18.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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+H]+	136.925	30932474
DeepCCS	[M-H]-	134.385	30932474
DeepCCS	[M-2H]-	170.421	30932474
DeepCCS	[M+Na]+	145.794	30932474
AllCCS	[M+H]+	140.2	32859911
AllCCS	[M+H-H2O]+	135.9	32859911
AllCCS	[M+NH4]+	144.3	32859911
AllCCS	[M+Na]+	145.5	32859911
AllCCS	[M-H]-	140.9	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	141.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Methylenedioxy-2-aminoindane	NC1CC2=CC3=C(OCO3)C=C2C1	2638.1	Standard polar	33892256
5,6-Methylenedioxy-2-aminoindane	NC1CC2=CC3=C(OCO3)C=C2C1	1650.2	Standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane	NC1CC2=CC3=C(OCO3)C=C2C1	1621.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,6-Methylenedioxy-2-aminoindane,1TMS,isomer #1	C[Si](C)(C)NC1CC2=CC3=C(C=C2C1)OCO3	1783.8	Semi standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane,1TMS,isomer #1	C[Si](C)(C)NC1CC2=CC3=C(C=C2C1)OCO3	1738.4	Standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane,1TMS,isomer #1	C[Si](C)(C)NC1CC2=CC3=C(C=C2C1)OCO3	2446.0	Standard polar	33892256
5,6-Methylenedioxy-2-aminoindane,2TMS,isomer #1	C[Si](C)(C)N(C1CC2=CC3=C(C=C2C1)OCO3)[Si](C)(C)C	1949.2	Semi standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane,2TMS,isomer #1	C[Si](C)(C)N(C1CC2=CC3=C(C=C2C1)OCO3)[Si](C)(C)C	1914.9	Standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane,2TMS,isomer #1	C[Si](C)(C)N(C1CC2=CC3=C(C=C2C1)OCO3)[Si](C)(C)C	2544.0	Standard polar	33892256
5,6-Methylenedioxy-2-aminoindane,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CC2=CC3=C(C=C2C1)OCO3	2031.5	Semi standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CC2=CC3=C(C=C2C1)OCO3	1960.3	Standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CC2=CC3=C(C=C2C1)OCO3	2617.6	Standard polar	33892256
5,6-Methylenedioxy-2-aminoindane,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CC2=CC3=C(C=C2C1)OCO3)[Si](C)(C)C(C)(C)C	2413.8	Semi standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CC2=CC3=C(C=C2C1)OCO3)[Si](C)(C)C(C)(C)C	2401.1	Standard non polar	33892256
5,6-Methylenedioxy-2-aminoindane,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CC2=CC3=C(C=C2C1)OCO3)[Si](C)(C)C(C)(C)C	2686.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Methylenedioxy-2-aminoindane GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ta-1900000000-c84f76a61eed0f53241a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 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 - 5,6-Methylenedioxy-2-aminoindane 10V, Positive-QTOF	splash10-01t9-0900000000-4359ad0b9f4d49377df5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 20V, Positive-QTOF	splash10-01t9-0900000000-e5f5705f54ea3ac47a28	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 40V, Positive-QTOF	splash10-001i-1900000000-f607e8bd9c506322c127	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 10V, Negative-QTOF	splash10-004i-0900000000-72db01fad781cbd5e1af	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 20V, Negative-QTOF	splash10-004i-0900000000-c215697305e7823ee006	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 40V, Negative-QTOF	splash10-005c-3900000000-6e87d2768e07a39b73b3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 10V, Positive-QTOF	splash10-03fr-0900000000-8a8bf626e91f677406a6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 20V, Positive-QTOF	splash10-01t9-0900000000-1a7194f8c9b6133ee2d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 40V, Positive-QTOF	splash10-0udi-0900000000-3e9971aff188cba3ed21	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 10V, Negative-QTOF	splash10-004i-0900000000-ef6ae59e91e658cf298a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 20V, Negative-QTOF	splash10-004i-0900000000-ef6ae59e91e658cf298a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Methylenedioxy-2-aminoindane 40V, Negative-QTOF	splash10-03dj-0900000000-71b664b6f182c2adde9c	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

111694

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

MDAI

METLIN ID

Not Available

PubChem Compound

125558

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 5,6-Methylenedioxy-2-aminoindane (HMDB0244545)

MOL for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

3D MOL for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

3D SDF for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

3D-SDF for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

PDB for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

3D PDB for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

SMILES for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

INCHI for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

Structure for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

3D Structure for HMDB0244545 (5,6-Methylenedioxy-2-aminoindane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra