NP-MRD: Showing NP-Card for 5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol (NP0170937)

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Record Information

Version

2.0

Created at

2022-09-03 07:14:52 UTC

Updated at

2022-09-03 07:14:53 UTC

NP-MRD ID

NP0170937

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol

Description

Halofuginone, also known as stenorol or C16H17BRCLN3O3, belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. Halofuginone is a very strong basic compound (based on its pKa). Poultry feed additive for prevention of coccidiosis. 5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol is found in Agave sisalana. 5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol was first documented in 1997 (PMID: 9407501). ; Halofuginone, a fully synthetic small molecule, is a potent and selective regulator of stromal cell activation, cell migration and Collagen type I synthesis, a process that has been identified as a 'master switch' in the body's tissue repair process (PMID: 19390970) (PMID: 20000346) (PMID: 11099465).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307212D          

 31 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061307212D          

 31 36  0  0  0  0            999 V2000
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 29 23  1  0  0  0  0
 30 14  1  0  0  0  0
 30 27  1  0  0  0  0
 31 22  1  0  0  0  0
 31 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170937

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CC(O)C23C)OC11CCC(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-24,28-29H,5-14H2,1-4H3

> <INCHI_KEY>
BQNMOLSYHYSCMS-UHFFFAOYSA-N

> <FORMULA>
C27H44O4

> <MOLECULAR_WEIGHT>
432.6359

> <EXACT_MASS>
432.323959896

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
51.72582022763372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
4.102073868333334

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.296396318178996

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.678837261728795

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3560752262354572

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
120.9314

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol

> <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      -1.028   7.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.394   5.430   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.437   6.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.685   6.131   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.974  10.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.436  10.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.467   6.344   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.512   6.499   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.975   6.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.987   6.594   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.357   9.161   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.112   9.886   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.900   6.230   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.035   8.976   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.491   7.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.626   6.952   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.820   9.072   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.203   7.875   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.745   8.893   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.591   7.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.208   8.803   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.744   9.179   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.362   6.141   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.994   7.659   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.128   7.696   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.516   7.427   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.531   8.035   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.741   7.964   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.671   4.764   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.555   9.226   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.222   9.411   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5    6   17                                                       
CONECT    6    5   19                                                       
CONECT    7   10   15                                                       
CONECT    8    9   18                                                       
CONECT    9    8   25                                                       
CONECT   10    7   27                                                       
CONECT   11   17   18                                                       
CONECT   12   21   22                                                       
CONECT   13   20   23                                                       
CONECT   14   15   30                                                       
CONECT   15    1    7   14                                                  
CONECT   16    2   24   27                                                  
CONECT   17    5   11   25                                                  
CONECT   18    8   11   28                                                  
CONECT   19    6   20   21                                                  
CONECT   20   13   19   25                                                  
CONECT   21   12   19   26                                                  
CONECT   22   12   24   31                                                  
CONECT   23   13   26   29                                                  
CONECT   24   16   22   26                                                  
CONECT   25    3    9   17   20                                             
CONECT   26    4   21   23   24                                             
CONECT   27   10   16   30   31                                             
CONECT   28   18                                                            
CONECT   29   23                                                            
CONECT   30   14   27                                                       
CONECT   31   22   27                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone, 9ci	HMDB
C16H17BRCLN3O3	HMDB
Halofuginona	HMDB
Halofuginonum	HMDB
7-Bromo-6-chlorofebrifugine	HMDB
Stenorol	HMDB
Halofunginone	HMDB
(3beta,5alpha,12beta,25R)-Spirostan-3,12-diol	HMDB
5alpha,25alpha-Spirostan-3beta,12-diol	HMDB
Rocogenin	HMDB

Chemical Formula

C₂₇H₄₄O₄

Average Mass

432.6359 Da

Monoisotopic Mass

432.32396 Da

IUPAC Name

5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol

Traditional Name

5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CC(O)C23C)OC11CCC(C)CO1

InChI Identifier

InChI=1S/C27H44O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-24,28-29H,5-14H2,1-4H3

InChI Key

BQNMOLSYHYSCMS-UHFFFAOYSA-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
Agave sisalana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolines

Alternative Parents

Substituents

Quinazoline
Pyrimidone
Aryl bromide
Aryl chloride
Aryl halide
Beta-aminoketone
Benzenoid
Pyrimidine
Piperidine
Heteroaromatic compound
1,2-aminoalcohol
Ketone
Lactam
Secondary alcohol
Secondary aliphatic amine
Azacycle
Secondary amine
Organobromide
Organohalogen compound
Amine
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Organooxygen compound
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	3.49	ALOGPS
logP	4.1	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	120.93 m³·mol⁻¹	ChemAxon
Polarizability	51.73 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031784

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008457

KNApSAcK ID

Not Available

Chemspider ID

56619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Halofuginone

METLIN ID

Not Available

PubChem Compound

62894

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Karakoyun B, Yuksel M, Ercan F, Salva E, Isik I, Yegen BC: Halofuginone, a specific inhibitor of collagen type 1 synthesis, ameliorates oxidant colonic damage in rats with experimental colitis. Dig Dis Sci. 2010 Mar;55(3):607-16. doi: 10.1007/s10620-009-0798-0. Epub 2009 Apr 24. [PubMed:19390970 ]
McLaughlin NP, Evans P: Dihydroxylation of vinyl sulfones: stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone. J Org Chem. 2010 Jan 15;75(2):518-21. doi: 10.1021/jo902396m. [PubMed:20000346 ]
Nagler A, Katz A, Aingorn H, Miao HQ, Condiotti R, Genina O, Pines M, Vlodavsky I: Inhibition of glomerular mesangial cell proliferation and extracellular matrix deposition by halofuginone. Kidney Int. 1997 Dec;52(6):1561-9. doi: 10.1038/ki.1997.486. [PubMed:9407501 ]
Elkin M, Miao HQ, Nagler A, Aingorn E, Reich R, Hemo I, Dou HL, Pines M, Vlodavsky I: Halofuginone: a potent inhibitor of critical steps in angiogenesis progression. FASEB J. 2000 Dec;14(15):2477-85. doi: 10.1096/fj.00-0292com. [PubMed:11099465 ]
LOTUS database [Link]

Showing NP-Card for 5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol (NP0170937)

MOL for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

3D MOL for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

3D SDF for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

3D-SDF for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

PDB for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

3D PDB for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

SMILES for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

INCHI for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

Structure for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)

3D Structure for NP0170937 (5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol)