NP-MRD: Showing NP-Card for methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate (NP0190147)

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Record Information

Version

2.0

Created at

2022-09-04 06:45:52 UTC

Updated at

2022-09-04 06:45:52 UTC

NP-MRD ID

NP0190147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate

Description

1H-indole-3-carboxylic acid, 1-(2,3-dihydroxy-1,1-dimethylpropyl) methyl ester belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate is found in Elmerina caryae. methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate was first documented in 2000 (PMID: 11014294). Based on a literature review very few articles have been published on 1H-indole-3-carboxylic acid, 1-(2,3-dihydroxy-1,1-dimethylpropyl) methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    5.0453   -2.0802    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414   -1.6525    0.4144 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425   -0.3948    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9890    0.4179    1.2939 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954   -0.0187    0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9545   -0.7830   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044   -0.0631   -0.4519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3927   -0.5814   -1.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8522   -1.6133   -2.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1509    0.3935   -1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386   -1.4008   -0.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3613   -1.8650   -0.8457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892   -0.7431    1.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4431    0.3207    0.8831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    1.1708    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8571    2.2827    0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638    3.4105    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9184    3.4542    1.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7283    2.3510    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2573    1.2076    0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5444   -1.3155    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836   -3.0370    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830   -2.2390   -0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871   -1.8009   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6587   -1.8226   -2.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5952   -2.5055   -1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463   -1.1640   -2.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432   -0.1142   -2.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764    1.2376   -2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1036    0.6563   -1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6940   -2.3579    0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089   -1.5380   -0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316   -1.4186    1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829   -0.4221    1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6011    0.7983    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578    2.2287   -0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9926    4.2847    0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890    4.3698    1.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7353    2.3462    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 20  5  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
M  END


  Mrv1652309042208452D          

 20 21  0  0  1  0            999 V2000
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684    1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288    1.5387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259    2.9365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  5 20  1  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CN(C2=CC=CC=C12)C(C)(C)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C15H19NO4/c1-15(2,13(18)9-17)16-8-11(14(19)20-3)10-6-4-5-7-12(10)16/h4-8,13,17-18H,9H2,1-3H3/t13-/m1/s1

> <INCHI_KEY>
BLYSKLWIPQGBES-CYBMUJFWSA-N

> <FORMULA>
C15H19NO4

> <MOLECULAR_WEIGHT>
277.32

> <EXACT_MASS>
277.131408096

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.55983611460421

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 1-[(3S)-3,4-dihydroxy-2-methylbutan-2-yl]-1H-indole-3-carboxylate

> <JCHEM_LOGP>
1.6758755776666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.557831260610016

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.517343693445145

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9656152819280264

> <JCHEM_POLAR_SURFACE_AREA>
71.69

> <JCHEM_REFRACTIVITY>
75.3783

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1-[(3S)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.114   1.884   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.185   0.932   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.174   2.872   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.333   3.192   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.204   4.017   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.728   5.481   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    7   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    5   15                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
1H-Indole-3-carboxylate, 1-(2,3-dihydroxy-1,1-dimethylpropyl) methyl ester	Generator

Chemical Formula

C₁₅H₁₉NO₄

Average Mass

277.3200 Da

Monoisotopic Mass

277.13141 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CN(C2=CC=CC=C12)C(C)(C)[C@H](O)CO

InChI Identifier

InChI=1S/C15H19NO4/c1-15(2,13(18)9-17)16-8-11(14(19)20-3)10-6-4-5-7-12(10)16/h4-8,13,17-18H,9H2,1-3H3/t13-/m1/s1

InChI Key

BLYSKLWIPQGBES-CYBMUJFWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Elmerina caryae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
N-alkylindole
Indole
Pyrrole-3-carboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Methyl ester
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
1,2-diol
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.68	ChemAxon
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8644147

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10468736

PDB ID

Not Available

ChEBI ID

189369

Good Scents ID

Not Available

References

General References

Levy LM, Cabrera GM, Wright JE, Seldes AM: Indole alkaloids from a culture of the fungus Aporpium caryae. Phytochemistry. 2000 Aug;54(8):941-3. doi: 10.1016/s0031-9422(00)00127-8. [PubMed:11014294 ]
LOTUS database [Link]

Showing NP-Card for methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate (NP0190147)

MOL for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

3D MOL for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

3D SDF for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

3D-SDF for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

PDB for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

3D PDB for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

SMILES for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

INCHI for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

Structure for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)

3D Structure for NP0190147 (methyl 1-[(3s)-3,4-dihydroxy-2-methylbutan-2-yl]indole-3-carboxylate)