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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-03-08 14:40:32 UTC

Update Date

2023-02-21 17:15:56 UTC

HMDB ID

HMDB0001896

Secondary Accession Numbers

HMDB01896

Metabolite Identification

Common Name

5-Methoxytryptophol

Description

5-Methoxytryptophol is synthesized by the pineal gland. Daily rhythms in pineal methoxyindole metabolism have been described in rodents and humans (5-Methoxytryptophol levels are coincident with serotonin levels in rodents pineal) and 5-Methoxytryptophol at its highest during the daylight hours and fall markedly soon after the onset of darkness, coincident with increases in the levels of pineal melatonin and the activities of pineal serotonin-N-acetyltransferase (EC 2.3.1.87, SNAT) and hydroxyindole-O-methyltransferase (EC 2.1.1.4, HIOMT). The fact that the levels of 5-methoxytryptophol and melatonin vary in parallel suggests that the major factor generating the methoxyindole rhythms is not SNAT activity, but perhaps a change in the availability (for metabolism) of "stored" serotonin. When the onset of darkness is delayed by 12 hours, human 5-methoxytryptophol (and melatonin) rhythms usually require 3 or 4 days to adjust to the new lighting regimen. Environmental factors, other than light, that activate the sympathetic nervous system or cause epinephrine to be secreted from the adrenal medulla (e.g., the stress of immobilization; insulin-induced hypoglycemia) can override the inhibitory effects of light and accelerate melatonin synthesis. Rhythms in 5-methoxytryptophol (and melatonin) synthesis apparently persist among animals placed in environments of continuous darkness; the source of the cyclic signal (mediated by the pineal sympathetic nerves) has not yet been identified. Preliminary evidence suggests that levels of a peptide hormone, arginine vasotocin, in rat pineal and sera also exhibit daily rhythms and are increased by norepinephrine. The circadian rhythm of melatonin secretion is generated in the suprachiasmatic nucleus. Sleep disruption, nightly restlessness, sundowning, and other circadian disturbances are frequently seen in Alzheimer's disease patients. Changes in the suprachiasmatic nucleus and pineal gland are thought to be the biological basis for these behavioral disturbances. (PMID 288858 , 2245336 ).

Structure

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


  Mrv1652305271900002D          

 14 15  0  0  0  0            999 V2000
   13.1808  -10.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1808  -11.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8952  -11.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6097  -11.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6097  -10.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8952   -9.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3943  -11.4141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8793  -10.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3943  -10.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6493   -9.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4562   -9.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7112   -8.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4664   -9.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4664   -9.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  5  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001896

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2NC=C(CCO)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3

> <INCHI_KEY>
QLWKTGDEPLRFAT-UHFFFAOYSA-N

> <FORMULA>
C11H13NO2

> <MOLECULAR_WEIGHT>
191.2264

> <EXACT_MASS>
191.094628665

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.8621175575064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-methoxy-1H-indol-3-yl)ethan-1-ol

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
1.4356479810000002

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.65783223206696

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.83195417589852

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4284988407908514

> <JCHEM_POLAR_SURFACE_AREA>
45.25

> <JCHEM_REFRACTIVITY>
55.17860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methoxytryptophol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      24.604 -19.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.604 -20.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.938 -21.600   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.271 -20.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.271 -19.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.938 -18.520   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      28.736 -21.306   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      29.641 -20.060   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.736 -18.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.212 -17.350   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.718 -17.030   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      31.194 -15.565   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      23.271 -18.520   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      23.271 -16.980   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    1   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0001896
HETATM    1  C1  UNL     1       4.465   1.132   0.594  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.098   1.484   0.548  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.156   0.470   0.340  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.565  -0.857   0.182  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.658  -1.868  -0.024  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.321  -1.550  -0.072  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.788  -2.317  -0.257  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.889  -1.551  -0.227  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.526  -0.247  -0.018  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.325   0.976   0.098  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.806   0.715  -0.042  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.535   1.892   0.073  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.142  -0.254   0.078  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.807   0.727   0.282  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.107   1.984   0.882  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.629   0.305   1.338  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.848   0.758  -0.375  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.632  -1.082   0.224  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.028  -2.870  -0.139  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.754  -3.347  -0.400  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.911  -1.869  -0.342  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.133   1.412   1.101  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.061   1.743  -0.674  1.00  0.00           H  
HETATM   24  H10 UNL     1      -4.054   0.280  -1.031  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.192   0.016   0.716  1.00  0.00           H  
HETATM   26  H12 UNL     1      -4.685   2.147   1.024  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.485   1.772   0.406  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   13
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   13
CONECT   10   11   22   23
CONECT   11   12   24   25
CONECT   12   26
CONECT   13   14   14
CONECT   14   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methoxytryptophol	MeSH
5-Methoxy-1H-indole-3-ethanol	HMDB
5-Methoxyindole-3-ethanol	HMDB
5-Methoxytryptophol	MeSH

Chemical Formula

C₁₁H₁₃NO₂

Average Molecular Weight

191.2264

Monoisotopic Molecular Weight

191.094628665

IUPAC Name

2-(5-methoxy-1H-indol-3-yl)ethan-1-ol

Traditional Name

methoxytryptophol

CAS Registry Number

712-09-4

SMILES

COC1=CC=C2NC=C(CCO)C2=C1

InChI Identifier

InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3

InChI Key

QLWKTGDEPLRFAT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Anisole
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Ether
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-12021 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Blood and lymphatic system disorder

Leukocytic disorder

Leukemia (HMDB: HMDB0001896)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8912232)
Cerebrospinal Fluid (CSF) (PMID: 1184685)
Cerebrospinal fluid (HMDB: HMDB0001896)

Source

Endogenous

Endogenous (HMDB: HMDB0001896)

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)

Process

Not Available

Role

Not Available

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	0.64 g/L	ALOGPS
logP	1.84	ALOGPS
logP	1.44	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.83	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	45.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.18 m³·mol⁻¹	ChemAxon
Polarizability	20.86 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	141.706	31661259
DarkChem	[M-H]-	142.997	31661259
AllCCS	[M+H]+	142.079	32859911
AllCCS	[M-H]-	144.597	32859911
DeepCCS	[M+H]+	140.427	30932474
DeepCCS	[M-H]-	137.51	30932474
DeepCCS	[M-2H]-	173.91	30932474
DeepCCS	[M+Na]+	149.449	30932474
AllCCS	[M+H]+	142.1	32859911
AllCCS	[M+H-H2O]+	137.8	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	144.6	32859911
AllCCS	[M+Na-2H]-	144.9	32859911
AllCCS	[M+HCOO]-	145.4	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.	4.0 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6792 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.45 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1497.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	331.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	131.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	339.7 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	328.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	819.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	360.8 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	1071.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	313.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	425.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	256.2 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	76.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxytryptophol	COC1=CC=C2NC=C(CCO)C2=C1	3136.8	Standard polar	33892256
5-Methoxytryptophol	COC1=CC=C2NC=C(CCO)C2=C1	1965.8	Standard non polar	33892256
5-Methoxytryptophol	COC1=CC=C2NC=C(CCO)C2=C1	2024.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxytryptophol,1TMS,isomer #1	COC1=CC=C2[NH]C=C(CCO[Si](C)(C)C)C2=C1	2022.2	Semi standard non polar	33892256
5-Methoxytryptophol,1TMS,isomer #2	COC1=CC=C2C(=C1)C(CCO)=CN2[Si](C)(C)C	2040.8	Semi standard non polar	33892256
5-Methoxytryptophol,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCO[Si](C)(C)C)=CN2[Si](C)(C)C	2052.8	Semi standard non polar	33892256
5-Methoxytryptophol,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCO[Si](C)(C)C)=CN2[Si](C)(C)C	2119.7	Standard non polar	33892256
5-Methoxytryptophol,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCO[Si](C)(C)C)=CN2[Si](C)(C)C	2299.8	Standard polar	33892256
5-Methoxytryptophol,1TBDMS,isomer #1	COC1=CC=C2[NH]C=C(CCO[Si](C)(C)C(C)(C)C)C2=C1	2287.4	Semi standard non polar	33892256
5-Methoxytryptophol,1TBDMS,isomer #2	COC1=CC=C2C(=C1)C(CCO)=CN2[Si](C)(C)C(C)(C)C	2299.4	Semi standard non polar	33892256
5-Methoxytryptophol,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCO[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2529.5	Semi standard non polar	33892256
5-Methoxytryptophol,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCO[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2530.4	Standard non polar	33892256
5-Methoxytryptophol,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCO[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2505.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxytryptophol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dj-0900000000-56fc4171bff27cc8b08f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxytryptophol GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-4290000000-b6f1d2b77bcf63cdb2f6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxytryptophol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxytryptophol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-006x-0900000000-8a87d83f5ab6d4e9e2cc	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxytryptophol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-053r-0900000000-c2439fe463c8095a7d48	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Methoxytryptophol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-0900000000-8eaf28224968f5678d87	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 10V, Positive-QTOF	splash10-00dl-0900000000-1daafd240067b254f72c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 20V, Positive-QTOF	splash10-00di-0900000000-f1948c2696d6933b1288	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 40V, Positive-QTOF	splash10-00l7-0900000000-e7c232e2fb6c1faceb85	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 10V, Negative-QTOF	splash10-0006-0900000000-f761824cdb02ac2006c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 20V, Negative-QTOF	splash10-01ox-0900000000-10aea01d485547bbcdba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 40V, Negative-QTOF	splash10-001i-0900000000-f47925a67fbbcd379d7c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 10V, Positive-QTOF	splash10-006x-0900000000-7be83e05ff8f3addc080	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 20V, Positive-QTOF	splash10-03kc-0900000000-8ea363f0b61f5e752cb0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 40V, Positive-QTOF	splash10-001i-0900000000-d3b88ac758801b950a73	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 10V, Negative-QTOF	splash10-0006-0900000000-6c413ff2e4d57d5c760e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 20V, Negative-QTOF	splash10-0006-0900000000-f0a15e47d2011150926a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxytryptophol 40V, Negative-QTOF	splash10-052f-0900000000-bbc986579ed4331f0d9a	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

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	0.000058 +/- 0.00001 uM	Children (1-13 years old)	Male	Normal	8912232	details
Blood	Detected and Quantified	0.00009 +/- 0.000016 uM	Adolescent (13-18 years old)	Male	Normal	8912232	details
Blood	Detected and Quantified	0.00009 +/- 0.000016 uM	Children (1-13 years old)	Female	Normal	8912232	details
Blood	Detected and Quantified	0.00015 +/- 0.00002 uM	Adult (>18 years old)	Both	Normal	2758645	details
Blood	Detected and Quantified	0.00016 +/- 0.00003 uM	Adult (>18 years old)	Both	Normal	2758645	details
Blood	Detected and Quantified	0.00014 +/- 0.00001 uM	Adult (>18 years old)	Both	Normal	2758645	details
Blood	Detected and Quantified	0.00017 +/- 0.00003 uM	Adult (>18 years old)	Male	Normal	2758645	details
Blood	Detected and Quantified	0.00014 +/- 0.000016 uM	Adult (>18 years old)	Female	Normal	2758645	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.03 +/- 0.22 (0.004 - 0.04) uM	Children (1-13 years old)	Both	Leukemia	1184685	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.02 +/- 0.022 (0 - 0.07) uM	Adult (>18 years old)	Both	Neurological disorders (2 - 18 years old)	1184685	details

Associated Disorders and Diseases

Disease References

Leukemia
Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022726

KNApSAcK ID

Not Available

Chemspider ID

12305

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tryptophol

METLIN ID

Not Available

PubChem Compound

12835

PDB ID

Not Available

ChEBI ID

114833

Food Biomarker Ontology

Not Available

VMH ID

CE6205

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Taborsky, Robert G.; Delvigs, Peter. Synthesis of some substituted tryptophols of possible physiological importance and a study with 3-(2-acetoxyethyl)-5-methoxyindole (5-methoxytryptophol O-acetate) on sexual maturation. J. Med. Chem., 1966, 9 (2), pp 251–254 DOI: 10.1021/jm00320a028

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wurtman RJ, Ozaki Y: Physiological control of melatonin synthesis and secretion: mechanisms, generating rhythms in melatonin, methoxytryptophol, and arginine vasotocin levels and effects on the pineal of endogenous catecholamines, the estrous cycle, and environmental lighting. J Neural Transm Suppl. 1978;(13):59-70. [PubMed:288858 ]
Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
Skene DJ, Vivien-Roels B, Sparks DL, Hunsaker JC, Pevet P, Ravid D, Swaab DF: Daily variation in the concentration of melatonin and 5-methoxytryptophol in the human pineal gland: effect of age and Alzheimer's disease. Brain Res. 1990 Sep 24;528(1):170-4. [PubMed:2245336 ]

Showing metabocard for 5-Methoxytryptophol (HMDB0001896)

MOL for HMDB0001896 (5-Methoxytryptophol)

3D MOL for HMDB0001896 (5-Methoxytryptophol)

3D SDF for HMDB0001896 (5-Methoxytryptophol)

3D-SDF for HMDB0001896 (5-Methoxytryptophol)

PDB for HMDB0001896 (5-Methoxytryptophol)

3D PDB for HMDB0001896 (5-Methoxytryptophol)

SMILES for HMDB0001896 (5-Methoxytryptophol)

INCHI for HMDB0001896 (5-Methoxytryptophol)

Structure for HMDB0001896 (5-Methoxytryptophol)

3D Structure for HMDB0001896 (5-Methoxytryptophol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra