NP-MRD: Showing NP-Card for Guar gum (NP0339569)

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Record Information

Version

2.0

Created at

2024-09-11 22:29:42 UTC

Updated at

2024-09-11 22:29:42 UTC

NP-MRD ID

NP0339569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Guar gum

Description

Tacrolimus, also known as prograf, belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group. Tacrolimus is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, tacrolimus is involved in t cell receptor signaling pathway. Guar gum was first documented in 2005 (PMID: 16021174). Tacrolimus is a potentially toxic compound (PMID: 16702731).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307191923542D          

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M  END


  Mrv1652307191923542D          

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 57 40  1  0  0  0  0
 57 44  1  0  0  0  0
 58 19  1  0  0  0  0
 59 21  1  0  0  0  0
 26 60  1  1  0  0  0
 28 61  1  6  0  0  0
 29 62  1  6  0  0  0
 30 63  1  6  0  0  0
 31 64  1  1  0  0  0
 32 65  1  6  0  0  0
 33 66  1  1  0  0  0
 34 67  1  6  0  0  0
 36 68  1  6  0  0  0
 37 69  1  1  0  0  0
 38 70  1  6  0  0  0
 39 71  1  1  0  0  0
 40 72  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0339569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])/[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)OC

> <INCHI_IDENTIFIER>
InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19-,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1

> <INCHI_KEY>
QJJXYPPXXYFBGM-LJIGMGMYSA-N

> <FORMULA>
C44H69NO12

> <MOLECULAR_WEIGHT>
804.0182

> <EXACT_MASS>
803.481976677

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
88.1362752348501

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
5.594120193333334

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.071408376193439

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.955600393207165

> <JCHEM_PKA_STRONGEST_BASIC>
-2.937095707399786

> <JCHEM_POLAR_SURFACE_AREA>
178.35999999999993

> <JCHEM_REFRACTIVITY>
215.62030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0       3.714  -4.756   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.231  -4.466   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.110  -1.591   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.327  -2.865   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.383   5.380   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.343   0.682   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.263  -8.713   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.923   2.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.835   5.166   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.222  -5.068   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.899   2.671   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.415   4.133   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.246  -3.918   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.169   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.255  -6.315   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.739  -7.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.907   4.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.632  -1.719   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.738  -3.606   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.606   0.552   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.795  -3.703   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.851   4.542   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.787  -5.477   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.295  -1.618   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.230  -3.294   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.294  -0.956   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.819  -2.553   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.359   4.230   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.827  -0.780   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.279  -5.165   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.763  -2.456   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.367   1.833   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.247  -8.089   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.803  -1.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.271  -2.768   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.271  -6.939   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.136   0.721   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.827   3.392   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.335  -1.091   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.311   1.930   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.351   2.456   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.375   3.606   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.875   1.521   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.843   2.768   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      10.883   3.294   0.000  0.00  0.00           N+0
HETATM   46  O   UNK     0      13.731  -9.551   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      10.287  -3.392   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       7.755  -4.230   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       8.835   0.994   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       8.891   5.068   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      14.380   1.849   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       7.867   3.918   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      15.779  -7.251   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       2.460   2.104   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       2.319   3.704   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      13.359   0.059   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       5.819   1.618   0.000  0.00  0.00           O+0
HETATM   58  H   UNK     0       5.693  -4.815   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      10.271  -3.926   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.222  -2.495   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.875   5.692   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0       9.319  -0.468   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      10.771  -4.854   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       5.451  -3.964   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      12.573   2.790   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      12.223  -9.239   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0       8.779  -3.080   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      15.295  -5.789   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.787   1.463   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.343   4.854   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0      11.311  -2.241   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0       3.018   2.767   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   53                                                            
CONECT    8   54                                                            
CONECT    9   55                                                            
CONECT   10    1   13                                                       
CONECT   11   12   14                                                       
CONECT   12   11   17                                                       
CONECT   13   10   31                                                       
CONECT   14   11   32                                                       
CONECT   15   16   30                                                       
CONECT   16   15   33                                                       
CONECT   17   12   45                                                       
CONECT   18   25   26                                                       
CONECT   19   25   31   58                                                  
CONECT   20   26   37                                                       
CONECT   21   27   30   59                                                  
CONECT   22   28   38                                                       
CONECT   23   30   36                                                       
CONECT   24   34   35                                                       
CONECT   25    2   18   19                                                  
CONECT   26    3   18   20   60                                             
CONECT   27    4   21   39                                                  
CONECT   28    5   22   44   61                                             
CONECT   29    6   34   39   62                                             
CONECT   30   15   21   23   63                                             
CONECT   31   13   19   35   64                                             
CONECT   32   14   43   45   65                                             
CONECT   33   16   36   46   66                                             
CONECT   34   24   29   47   67                                             
CONECT   35   24   31   48                                                  
CONECT   36   23   33   53   68                                             
CONECT   37   20   40   54   69                                             
CONECT   38   22   40   55   70                                             
CONECT   39   27   29   56   71                                             
CONECT   40   37   38   57   72                                             
CONECT   41   42   44   49                                                  
CONECT   42   41   45   50                                                  
CONECT   43   32   51   56                                                  
CONECT   44   28   41   52   57                                             
CONECT   45   17   32   42                                                  
CONECT   46   33                                                            
CONECT   47   34                                                            
CONECT   48   35                                                            
CONECT   49   41                                                            
CONECT   50   42                                                            
CONECT   51   43                                                            
CONECT   52   44                                                            
CONECT   53    7   36                                                       
CONECT   54    8   37                                                       
CONECT   55    9   38                                                       
CONECT   56   39   43                                                       
CONECT   57   40   44                                                       
CONECT   58   19                                                            
CONECT   59   21                                                            
CONECT   60   26                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   33                                                            
CONECT   67   34                                                            
CONECT   68   36                                                            
CONECT   69   37                                                            
CONECT   70   38                                                            
CONECT   71   39                                                            
CONECT   72   40                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  150    0
END

View in JSmol

Synonyms

Value	Source
Anhydrous, tacrolimus	HMDB
Anhydrous tacrolimus	HMDB
Prograf	HMDB
Tacrolimus anhydrous	HMDB
Tacrolimus, anhydrous	HMDB
Fujisawa brand OF tacrolimus	HMDB
Prograft	HMDB
Cilag brand OF tacrolimus	HMDB
Janssen brand OF tacrolimus	HMDB

Chemical Formula

C₄₄H₆₉NO₁₂

Average Mass

804.0182 Da

Monoisotopic Mass

803.48198 Da

IUPAC Name

(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])/[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)OC

InChI Identifier

InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19-,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1

InChI Key

QJJXYPPXXYFBGM-LJIGMGMYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolide lactams

Sub Class

Not Available

Direct Parent

Macrolide lactams

Alternative Parents

Substituents

Macrolide lactam
Alpha-amino acid ester
Macrolide
Alpha-amino acid or derivatives
Cyclohexanol
Oxane
Piperidine
Cyclic alcohol
Tertiary carboxylic acid amide
Cyclic ketone
Secondary alcohol
Carboxamide group
Carboxylic acid ester
Hemiacetal
Ketone
Lactam
Lactone
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.19	ALOGPS
logP	5.59	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	178.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	215.62 m³·mol⁻¹	ChemAxon
Polarizability	88.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015002

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011098

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tacrolimus

METLIN ID

Not Available

PubChem Compound

6473866

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hanifin JM, Paller AS, Eichenfield L, Clark RA, Korman N, Weinstein G, Caro I, Jaracz E, Rico MJ: Efficacy and safety of tacrolimus ointment treatment for up to 4 years in patients with atopic dermatitis. J Am Acad Dermatol. 2005 Aug;53(2 Suppl 2):S186-94. doi: 10.1016/j.jaad.2005.04.062. [PubMed:16021174 ]
Fukatsu S, Fukudo M, Masuda S, Yano I, Katsura T, Ogura Y, Oike F, Takada Y, Inui K: Delayed effect of grapefruit juice on pharmacokinetics and pharmacodynamics of tacrolimus in a living-donor liver transplant recipient. Drug Metab Pharmacokinet. 2006 Apr;21(2):122-5. doi: 10.2133/dmpk.21.122. [PubMed:16702731 ]

Showing NP-Card for Guar gum (NP0339569)

MOL for NP0339569 (Guar gum)

3D MOL for NP0339569 (Guar gum)

3D SDF for NP0339569 (Guar gum)

3D-SDF for NP0339569 (Guar gum)

PDB for NP0339569 (Guar gum)

3D PDB for NP0339569 (Guar gum)

SMILES for NP0339569 (Guar gum)

INCHI for NP0339569 (Guar gum)

Structure for NP0339569 (Guar gum)

3D Structure for NP0339569 (Guar gum)