NP-MRD: Showing NP-Card for 25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione (NP0297564)

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Record Information

Version

2.0

Created at

2022-09-10 08:01:16 UTC

Updated at

2022-09-10 08:01:16 UTC

NP-MRD ID

NP0297564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione

Description

25-(1,2-Dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]Pentacosa-2,4,7(12),8,10,14,18,20,22-nonaene-6,13-dione belongs to the class of organic compounds known as 6-hydroxysteroids. These are steroids carrying a hydroxyl group at the 6-position of the steroid backbone. 25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione is found in Micromonospora yangpuensis. Based on a literature review very few articles have been published on 25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]Pentacosa-2,4,7(12),8,10,14,18,20,22-nonaene-6,13-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102210012D          

 35 40  0  0  0  0            999 V2000
    7.4983    3.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2749    2.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0988    2.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4738    1.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0249    0.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2010    0.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0746    0.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8260    1.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309102210012D          

 35 40  0  0  0  0            999 V2000
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    7.2749    2.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0249    0.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0297564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(O)C1(O)C2NC3=C4C(=O)C5=C(O)C=CC=C5C(=O)C4=C(O)C=C3C1C(O)C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C26H21NO8/c28-9-16(31)26(35)20-13-8-15(30)18-19(24(34)17-12(22(18)32)6-3-7-14(17)29)21(13)27-25(26)11-5-2-1-4-10(11)23(20)33/h1-8,16,20,23,25,27-31,33,35H,9H2

> <INCHI_KEY>
WRDWJGFTPSNCEK-UHFFFAOYSA-N

> <FORMULA>
C26H21NO8

> <MOLECULAR_WEIGHT>
475.453

> <EXACT_MASS>
475.12671664

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
47.279851353100355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0^{2,15}.0^{5,14}.0^{7,12}.0^{18,23}]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione

> <JCHEM_LOGP>
2.312324378

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.085792139967008

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.13614013139219

> <JCHEM_PKA_STRONGEST_BASIC>
1.1929953958639996

> <JCHEM_POLAR_SURFACE_AREA>
167.54999999999998

> <JCHEM_REFRACTIVITY>
125.53219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0^{2,15}.0^{5,14}.0^{7,12}.0^{18,23}]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0      13.997   6.937   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.880   5.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.580   4.399   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.118   4.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.818   2.948   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.980   1.656   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.442   1.735   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.206   0.128   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.742   3.107   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.204   3.187   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.395   1.584   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.504   4.558   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.966   4.638   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.266   6.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.104   7.302   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.642   7.222   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.258   8.722   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.342   5.851   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.801   6.485   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.429   5.785   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.410   7.025   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.954   4.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.416   4.399   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.579   3.107   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.279   1.735   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.817   1.656   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.654   2.948   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.119   2.473   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       8.491   3.173   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       7.462   4.519   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.683   5.411   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.178   3.698   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.988   5.232   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.502   1.938   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.472   0.742   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12    2                                                  
CONECT   19   14   20   30                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   13                                                       
CONECT   30   28   19   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₁NO₈

Average Mass

475.4530 Da

Monoisotopic Mass

475.12672 Da

IUPAC Name

25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0^{2,15}.0^{5,14}.0^{7,12}.0^{18,23}]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione

Traditional Name

25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0^{2,15}.0^{5,14}.0^{7,12}.0^{18,23}]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione

CAS Registry Number

Not Available

SMILES

OCC(O)C1(O)C2NC3=C4C(=O)C5=C(O)C=CC=C5C(=O)C4=C(O)C=C3C1C(O)C1=CC=CC=C21

InChI Identifier

InChI=1S/C26H21NO8/c28-9-16(31)26(35)20-13-8-15(30)18-19(24(34)17-12(22(18)32)6-3-7-14(17)29)21(13)27-25(26)11-5-2-1-4-10(11)23(20)33/h1-8,16,20,23,25,27-31,33,35H,9H2

InChI Key

WRDWJGFTPSNCEK-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
Micromonospora yangpuensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-hydroxysteroids. These are steroids carrying a hydroxyl group at the 6-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

6-hydroxysteroids

Alternative Parents

Substituents

6-hydroxysteroid
Anthraquinone
9,10-anthraquinone
Anthracene
Tetralin
Tetrahydroquinoline
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Secondary aliphatic/aromatic amine
Benzenoid
Vinylogous amide
Vinylogous acid
Tertiary alcohol
1,3-aminoalcohol
Secondary alcohol
Ketone
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Secondary amine
Polyol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	2.31	ChemAxon
pKa (Strongest Acidic)	8.14	ChemAxon
pKa (Strongest Basic)	1.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	167.55 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	125.53 m³·mol⁻¹	ChemAxon
Polarizability	47.28 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163085422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione (NP0297564)

MOL for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

3D MOL for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

3D SDF for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

3D-SDF for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

PDB for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

3D PDB for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

SMILES for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

INCHI for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

Structure for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)

3D Structure for NP0297564 (25-(1,2-dihydroxyethyl)-4,11,24,25-tetrahydroxy-16-azahexacyclo[15.7.1.0²,¹⁵.0⁵,¹⁴.0⁷,¹².0¹⁸,²³]pentacosa-2,4,7,9,11,14,18,20,22-nonaene-6,13-dione)