NP-MRD: Showing NP-Card for (1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol (NP0262028)

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Record Information

Version

2.0

Created at

2022-09-08 04:38:13 UTC

Updated at

2022-09-08 04:38:13 UTC

NP-MRD ID

NP0262028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol

Description

Mahuannin D belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. (1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol was first documented in 2008 (PMID: 18975262). Based on a literature review very few articles have been published on Mahuannin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082206382D          

 39 45  0  0  1  0            999 V2000
    6.3724    4.5374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3660    3.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0773    3.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0709    2.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3533    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3469    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6292    0.8305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229    0.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3341   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3277   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  2 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309082206382D          

 39 45  0  0  1  0            999 V2000
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 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 26 33  1  0  0  0  0
 15 33  1  0  0  0  0
 17 34  1  0  0  0  0
 13 34  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  1  6  0  0  0
  5 38  1  0  0  0  0
 38 39  2  0  0  0  0
  2 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262028

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C1=C(O[C@@]3(C[C@H]1C1=C(O)C=C(O)C=C1O3)C1=CC=C(O)C=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O9/c31-16-5-1-14(2-6-16)28-23(36)11-19-21(34)12-25-27(29(19)37-28)20-13-30(39-25,15-3-7-17(32)8-4-15)38-24-10-18(33)9-22(35)26(20)24/h1-10,12,20,23,28,31-36H,11,13H2/t20-,23+,28+,30-/m0/s1

> <INCHI_KEY>
BHGCRZWUKWPRDM-JAPFCTHZSA-N

> <FORMULA>
C30H24O9

> <MOLECULAR_WEIGHT>
528.513

> <EXACT_MASS>
528.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
54.012028815890986

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5R,6R,13S)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol

> <JCHEM_LOGP>
4.965911150999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.303785759736149

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.870834032648668

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2870979672653213

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
139.0604

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6R,13S)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0      11.895   8.470   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.883   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.211   6.150   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.199   4.610   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.859   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.848   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.508   1.550   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.496   0.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.824  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.812  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.139  -3.090   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.472  -3.070   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.144  -2.289   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.156  -0.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.076   0.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.755  -1.701   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.507  -3.358   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.907  -4.776   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.835  -6.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.235  -7.423   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.706  -7.612   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.106  -9.031   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.778  -6.383   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.379  -4.965   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.427  -2.261   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.439  -0.721   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.954  -0.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.567   1.180   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.083   1.590   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.665   2.261   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.149   1.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.246   2.931   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.536   0.360   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.047  -3.370   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.163  -0.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.175   1.530   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.515   2.289   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.532   4.630   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.544   6.170   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   35                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   25   34                                             
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   17   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26   15                                                  
CONECT   34   17   13                                                       
CONECT   35    9   36                                                       
CONECT   36   35    6   37                                                  
CONECT   37   36                                                            
CONECT   38    5   39                                                       
CONECT   39   38    2                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Value	Source
ent-Apigeniflavan-(2alpha->7,4alpha->8)-epiafzelechin	Kegg
ent-Apigeniflavan-(2a->7,4a->8)-epiafzelechin	Generator
ent-Apigeniflavan-(2α->7,4α->8)-epiafzelechin	Generator

Chemical Formula

C₃₀H₂₄O₉

Average Mass

528.5130 Da

Monoisotopic Mass

528.14203 Da

IUPAC Name

(1S,5R,6R,13S)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol

Traditional Name

(1S,5R,6R,13S)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C1=C(O[C@@]3(C[C@H]1C1=C(O)C=C(O)C=C1O3)C1=CC=C(O)C=C1)C=C2O

InChI Identifier

InChI=1S/C30H24O9/c31-16-5-1-14(2-6-16)28-23(36)11-19-21(34)12-25-27(29(19)37-28)20-13-30(39-25,15-3-7-17(32)8-4-15)38-24-10-18(33)9-22(35)26(20)24/h1-10,12,20,23,28,31-36H,11,13H2/t20-,23+,28+,30-/m0/s1

InChI Key

BHGCRZWUKWPRDM-JAPFCTHZSA-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 biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
Pyranoflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Pyranochromene
1-benzopyran
Chromane
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketal
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Ether
Alcohol
Organooxygen compound
Organic oxygen compound
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	4.97	ChemAxon
pKa (Strongest Acidic)	8.87	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	139.06 m³·mol⁻¹	ChemAxon
Polarizability	54.01 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00002930

Chemspider ID

391044

KEGG Compound ID

C10234

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tao H, Wang L, Cui Z, Zhao D, Liu Y: Dimeric proanthocyanidins from the roots of Ephedra sinica. Planta Med. 2008 Dec;74(15):1823-5. doi: 10.1055/s-0028-1088321. Epub 2008 Oct 30. [PubMed:18975262 ]
LOTUS database [Link]

Showing NP-Card for (1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol (NP0262028)

MOL for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

3D MOL for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

3D SDF for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

3D-SDF for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

PDB for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

3D PDB for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

SMILES for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

INCHI for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

Structure for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)

3D Structure for NP0262028 ((1s,5r,6r,13s)-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol)