NP-MRD: Showing NP-Card for (4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate (NP0252843)

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Record Information

Version

2.0

Created at

2022-09-07 16:30:04 UTC

Updated at

2022-09-07 16:30:04 UTC

NP-MRD ID

NP0252843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate

Description

Acetic acid 3-formyl-4alpha-hydroxy 4,5,6,7-tetrahydro-1H-indole-5beta-yl ester belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review very few articles have been published on Acetic acid 3-formyl-4alpha-hydroxy 4,5,6,7-tetrahydro-1H-indole-5beta-yl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    4.3770   -0.1938    0.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0431    0.2836    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891    1.4782    0.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1272   -0.6558    0.0411 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -0.2962   -0.3973 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5608   -0.6317   -1.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083   -0.6144   -2.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7484    0.1059   -1.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8369    0.8983   -1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2328    1.2991   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3642    0.7415    0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    0.9049    2.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2890    1.6050    2.8847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329   -0.0070    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -0.8455    0.5000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0950   -0.7456    1.8478 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9278    0.5771    1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9968   -0.3579    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -1.1686    1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654    0.8264   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336   -1.5984   -2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    0.1212   -2.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100   -0.2158   -3.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.6785   -2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3174    1.1730   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0652    1.9358    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6907    0.4268    2.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5098   -1.8914    0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -1.4762    2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 14  2  0
 14 15  1  0
 15 16  1  0
 14 11  1  0
 11 12  1  0
 12 13  2  0
 11 10  2  0
 10  9  1  0
 15  5  1  0
  9  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  6
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 15 28  1  6
 16 29  1  0
 12 27  1  0
 10 26  1  0
  9 25  1  0
M  END


  Mrv1652309072218302D          

 16 17  0  0  1  0            999 V2000
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  1  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    0.6979    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
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0252843

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CCC2=C([C@@H]1O)C(C=O)=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO4/c1-6(14)16-9-3-2-8-10(11(9)15)7(5-13)4-12-8/h4-5,9,11-12,15H,2-3H2,1H3/t9-,11+/m0/s1

> <INCHI_KEY>
VCLOZMYOWPWXOV-GXSJLCMTSA-N

> <FORMULA>
C11H13NO4

> <MOLECULAR_WEIGHT>
223.228

> <EXACT_MASS>
223.084457903

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.216620257796976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5S)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1H-indol-5-yl acetate

> <JCHEM_LOGP>
0.11739087933333361

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.351482885074056

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.187523994800767

> <JCHEM_PKA_STRONGEST_BASIC>
-3.547907096057269

> <JCHEM_POLAR_SURFACE_AREA>
79.39

> <JCHEM_REFRACTIVITY>
56.943

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1H-indol-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.925   2.073   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.143   5.874   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    8   15                                                  
CONECT   15   14    5   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Acetate 3-formyl-4a-hydroxy 4,5,6,7-tetrahydro-1H-indole-5b-yl ester	Generator
Acetate 3-formyl-4alpha-hydroxy 4,5,6,7-tetrahydro-1H-indole-5beta-yl ester	Generator
Acetate 3-formyl-4α-hydroxy 4,5,6,7-tetrahydro-1H-indole-5β-yl ester	Generator
Acetic acid 3-formyl-4a-hydroxy 4,5,6,7-tetrahydro-1H-indole-5b-yl ester	Generator
Acetic acid 3-formyl-4α-hydroxy 4,5,6,7-tetrahydro-1H-indole-5β-yl ester	Generator

Chemical Formula

C₁₁H₁₃NO₄

Average Mass

223.2280 Da

Monoisotopic Mass

223.08446 Da

IUPAC Name

(4S,5S)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1H-indol-5-yl acetate

Traditional Name

(4S,5S)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1H-indol-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CCC2=C([C@@H]1O)C(C=O)=CN2

InChI Identifier

InChI=1S/C11H13NO4/c1-6(14)16-9-3-2-8-10(11(9)15)7(5-13)4-12-8/h4-5,9,11-12,15H,2-3H2,1H3/t9-,11+/m0/s1

InChI Key

VCLOZMYOWPWXOV-GXSJLCMTSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Aryl-aldehyde
Substituted pyrrole
Pyrrole
Vinylogous amide
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Aldehyde
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	0.12	ChemAxon
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.94 m³·mol⁻¹	ChemAxon
Polarizability	22.22 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

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

9920940

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11746236

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate (NP0252843)

MOL for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

3D MOL for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

3D SDF for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

3D-SDF for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

PDB for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

3D PDB for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

SMILES for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

INCHI for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

Structure for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)

3D Structure for NP0252843 ((4s,5s)-3-formyl-4-hydroxy-4,5,6,7-tetrahydro-1h-indol-5-yl acetate)