NP-MRD: Showing NP-Card for Progoitrin (NP0047841)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:50 UTC

Updated at

2022-03-17 20:46:50 UTC

NP-MRD ID

NP0047841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Progoitrin

Description

Progoitrin, also known as glucorapiferin, belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Progoitrin is found in Alyssum alyssoides, Alyssum dasycarpum, Alyssum granatense, Alyssum minutum, Arabidopsis thaliana, Boreava orientalis, Brassica spp., Brassica sprouts, Capparis flexuosa, Capparis inermis , Capsella bursa-pastoris , Chorispora purpurascens, Coincya longirostra, Coincya monensis , Coincya rupestris, Coincya transtagana, Conringia orientalis, Crambe abyssinica, Crambe cordifolia , Crambe filiformis, Crambe juncea, Crambe koktebelica, Crambe maritima , Crambe orientalis , Crambe tataria, Descurainia pinnata, Diplotaxis virgata, Enarthrocarpus strangulatus, Erucaria hispanica, Fibigia macrocarpa, Hesperis matronalis , Hirschfeldia incana , Isatis cappadocica, Isatis costata, Isatis djurdjura, Isatis tinctoria , Moricandia arvensis , Moricandia baetica, Moricandia foetida, Moricandia moricandioides, Notoceras bicorne, Peltaria alliaceae, Raphanus sativus, Rhynchosinapis hispida, Rhynchosinapis longirostra, Rytidocarpus moricandioides, Schouwia purpurea, Selenia grandis, Sinapis arvensis , Sisymbrium altissimum, Sisymbrium gariepinum, Sisymbrium irio , Sisymbrium orientale, Sisymbrium pinnata, Stanleya pinnata, Thelypodium flexuosum, Thelypodium integrifolium, Thelypodium repandum, Thelypodium wrightii and Zilla spinosa . Progoitrin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307332D          

 24 24  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 21  6  1  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 23  7  1  0  0  0  0
 23 11  1  0  0  0  0
 24 18  1  0  0  0  0
 24 19  2  0  0  0  0
 24 20  2  0  0  0  0
 24 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(S\C(CC(O)C=C)=N\OS(O)(=O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO10S2/c1-2-5(14)3-7(12-22-24(18,19)20)23-11-10(17)9(16)8(15)6(4-13)21-11/h2,5-6,8-11,13-17H,1,3-4H2,(H,18,19,20)/b12-7+

> <INCHI_KEY>
MYHSVHWQEVDFQT-KPKJPENVSA-N

> <FORMULA>
C11H19NO10S2

> <MOLECULAR_WEIGHT>
389.399

> <EXACT_MASS>
389.045037213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
35.79730213050468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(E)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxy}sulfonic acid

> <ALOGPS_LOGP>
-1.91

> <JCHEM_LOGP>
-3.84562464985445

> <ALOGPS_LOGS>
-1.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.445277285282287

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.5906148976778125

> <JCHEM_PKA_STRONGEST_BASIC>
-0.44968379950175363

> <JCHEM_POLAR_SURFACE_AREA>
186.33999999999997

> <JCHEM_REFRACTIVITY>
80.65959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.88e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.231  -0.976   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.771  -3.644   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   24  S   UNK     0      -4.001  -2.310   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    5                                                       
CONECT    3    5    7                                                       
CONECT    4    6   13                                                       
CONECT    5    2    3   14                                                  
CONECT    6    4    8   21                                                  
CONECT    7    3   12   23                                                  
CONECT    8    6    9   15                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   21   23                                                  
CONECT   12    7   22                                                       
CONECT   13    4                                                            
CONECT   14    5                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   24                                                            
CONECT   19   24                                                            
CONECT   20   24                                                            
CONECT   21    6   11                                                       
CONECT   22   12   24                                                       
CONECT   23    7   11                                                       
CONECT   24   18   19   20   22                                             
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
1-Thio-b-D-glucopyranose 1-[3-hydroxy-N-(sulfooxy)-4-pentenimidate], 9ci	HMDB
2(R)-2-Hydroxy-3-butenyl glucosinolate	HMDB
2-Hydroxy-3-butenyl glucosinolate	HMDB
Glucorapiferin	HMDB
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxy}sulfonate	Generator
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pent-4-en-1-ylidene)amino]oxy}sulphonate	Generator
{[(e)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}pent-4-en-1-ylidene)amino]oxy}sulphonic acid	Generator
Progoitrin	MeSH
Epi-progoitrin	MeSH
Epiprogoitrin	MeSH
Progoitrin, (S)-isomer	MeSH
Progoitrin, monopotassium salt	MeSH

Chemical Formula

C₁₁H₁₉NO₁₀S₂

Average Mass

389.3990 Da

Monoisotopic Mass

389.04504 Da

IUPAC Name

{[(E)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxy}sulfonic acid

Traditional Name

[(E)-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxysulfonic acid

CAS Registry Number

585-95-5

SMILES

OCC1OC(S\C(CC(O)C=C)=N\OS(O)(=O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C11H19NO10S2/c1-2-5(14)3-7(12-22-24(18,19)20)23-11-10(17)9(16)8(15)6(4-13)21-11/h2,5-6,8-11,13-17H,1,3-4H2,(H,18,19,20)/b12-7+

InChI Key

MYHSVHWQEVDFQT-KPKJPENVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alyssum alyssoides	Plant	KNApSAcK
Alyssum dasycarpum	Plant	KNApSAcK
Alyssum granatense	Plant	KNApSAcK
Alyssum minutum	Plant	KNApSAcK
Arabidopsis thaliana	Plant	KNApSAcK
Boreava orientalis	Plant	KNApSAcK
Brassica juncea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica napus	FooDB	PHYTOHUB
Brassica napus var. napus	FooDB	KNAPSACK
Brassica oleracea	FooDB	KNAPSACK
Brassica oleracea var. botrytis	FooDB	15963940
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gemmifera	FooDB	15963940
Brassica oleracea var. gongylodes	FooDB	PHYTOHUB
Brassica oleracea var. italica	FooDB	12720387
Brassica oleracea var. sabauda	FooDB	PHYTOHUB
Brassica rapa	FooDB	KNAPSACK
Brassica rapa var. rapa	FooDB	PHYTOHUB
Brassica spp.	Plant	KNApSAcK
Brassica sprouts	Plant	KNApSAcK
Capparis flexuosa	Plant	KNApSAcK
Capparis inermis	Plant	KNApSAcK
Capparis spinosa	FooDB	PHYTOHUB
Capsella bursa-pastoris	Plant	KNApSAcK
Chorispora purpurascens	Plant	KNApSAcK
Coincya longirostra	Plant	KNApSAcK
Coincya monensis	Plant	KNApSAcK
Coincya rupestris	Plant	KNApSAcK
Coincya transtagana	Plant	KNApSAcK
Conringia orientalis	Plant	KNApSAcK
Crambe abyssinica	Plant	KNApSAcK
Crambe cordifolia	Plant	KNApSAcK
Crambe filiformis	Plant	KNApSAcK
Crambe juncea	Plant	KNApSAcK
Crambe koktebelica	Plant	KNApSAcK
Crambe maritima	Plant	KNApSAcK
Crambe orientalis	Plant	KNApSAcK
Crambe tataria	Plant	KNApSAcK
Descurainia pinnata	Plant	KNApSAcK
Diplotaxis virgata	Plant	KNApSAcK
Enarthrocarpus strangulatus	Plant	KNApSAcK
Erucaria hispanica	Plant	KNApSAcK
Fibigia macrocarpa	Plant	KNApSAcK
Hesperis matronalis	Plant	KNApSAcK
Hirschfeldia incana	Plant	KNApSAcK
Isatis cappadocica	Plant	KNApSAcK
Isatis costata	Plant	KNApSAcK
Isatis djurdjura	Plant	KNApSAcK
Isatis tinctoria	Plant	KNApSAcK
Lepidium sativum	FooDB	KNAPSACK
Moricandia arvensis	Plant	KNApSAcK
Moricandia baetica	Plant	KNApSAcK
Moricandia foetida	Plant	KNApSAcK
Moricandia moricandioides	Plant	KNApSAcK
Notoceras bicorne	Plant	KNApSAcK
Peltaria alliaceae	Plant	KNApSAcK
Raphanus sativus	LOTUS Database	35616633
Rhynchosinapis hispida	-	KNApSAcK
Rhynchosinapis longirostra	-	KNApSAcK
Rytidocarpus moricandioides	Plant	KNApSAcK
Schouwia purpurea	Plant	KNApSAcK
Selenia grandis	Plant	KNApSAcK
Sinapis alba	FooDB	KNAPSACK
Sinapis arvensis	Plant	KNApSAcK
Sisymbrium altissimum	Plant	KNApSAcK
Sisymbrium gariepinum	Plant	KNApSAcK
Sisymbrium irio	Plant	KNApSAcK
Sisymbrium orientale	Plant	KNApSAcK
Sisymbrium pinnata	Plant	KNApSAcK
Stanleya pinnata	LOTUS Database	35616633
Thelypodium flexuosum	Plant	KNApSAcK
Thelypodium integrifolium	Plant	KNApSAcK
Thelypodium repandum	Plant	KNApSAcK
Thelypodium wrightii	Plant	KNApSAcK
Zilla spinosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Alkylglucosinolates

Alternative Parents

Substituents

Alkylglucosinolate
Glycosyl compound
S-glycosyl compound
Oxane
Monothioacetal
Organic sulfuric acid or derivatives
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic oxide
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-1.9	ALOGPS
logP	-3.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	186.34 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	80.66 m³·mol⁻¹	ChemAxon
Polarizability	35.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon