NP-MRD: Showing NP-Card for Asperustin I (NP0332894)

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Record Information

Version

2.0

Created at

2024-05-01 21:48:28 UTC

Updated at

2024-09-03 04:20:36 UTC

NP-MRD ID

NP0332894

Natural Product DOI

https://doi.org/10.57994/2174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperustin I

Description

Asperustin I was first documented in 2024 (PMID: 38441877).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142300252D          

 32 36  0  0  1  0            999 V2000
    3.7759   -3.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -2.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -2.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -1.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276   -0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -0.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0574    0.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9495    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395    0.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -1.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4890   -2.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -2.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3592   -3.6983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1215   -4.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -1.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145   -1.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688   -0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311   -1.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7390   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5503   -2.1543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1183   -2.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8629   -2.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7549   -1.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1568   -2.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9437   -1.4292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3372   -0.7040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -0.8309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -2.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -3.3245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3224   -2.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  5 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  6  0  0  0
 22 27  1  0  0  0  0
 27 25  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 18 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END


  Mrv2104 01142300252D          

 32 36  0  0  1  0            999 V2000
    3.7759   -3.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -2.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -2.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -1.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276   -0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -0.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0574    0.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9495    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395    0.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753    0.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -1.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4890   -2.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -2.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3592   -3.6983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1215   -4.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -1.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145   -1.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688   -0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311   -1.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7390   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5503   -2.1543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1183   -2.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8629   -2.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7549   -1.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1568   -2.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9437   -1.4292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3372   -0.7040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -0.8309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -2.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -3.3245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3224   -2.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  5 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  6  0  0  0
 22 27  1  0  0  0  0
 27 25  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 18 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C2OC3=C(C(=O)C2=C1O)C(OC)=CC=C3CCC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O8/c1-22(2,26)7-6-11-4-5-12(28-3)16-18(24)15-13(30-20(11)16)10-14-17(19(15)25)23(27)8-9-29-21(23)31-14/h4-5,8-10,21,25-27H,6-7H2,1-3H3/t21-,23-/m1/s1

> <INCHI_KEY>
ZICKMRKORQPECB-FYYLOGMGSA-N

> <FORMULA>
C23H22O8

> <MOLECULAR_WEIGHT>
426.421

> <EXACT_MASS>
426.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.49960507552203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,8R)-2,4-dihydroxy-15-(3-hydroxy-3-methylbutyl)-18-methoxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),5,11,14(19),15,17-heptaen-20-one

> <JCHEM_LOGP>
3.106443104666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.63952097070207

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.527519024748804

> <JCHEM_PKA_STRONGEST_BASIC>
-2.630405104740433

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
110.01939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R,8R)-2,4-dihydroxy-15-(3-hydroxy-3-methylbutyl)-18-methoxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),5,11,14(19),15,17-heptaen-20-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  O   UNK     0       7.048  -6.555   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.847  -5.028   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.424  -4.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.223  -2.912   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.800  -2.323   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.598  -0.796   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.175  -0.208   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.974   1.319   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.772   2.846   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.447   1.118   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.501   1.521   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.578  -3.261   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.780  -4.788   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.202  -5.377   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.404  -6.904   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.827  -7.492   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.444  -1.974   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.867  -2.563   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.088  -1.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.511  -2.214   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.713  -3.741   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.227  -4.021   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.288  -5.138   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.677  -4.475   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.476  -2.948   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      11.493  -5.375   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.962  -2.668   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      13.696  -1.314   0.000  0.00  0.00           H+0
HETATM   29  O   UNK     0      11.901  -1.551   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.491  -4.679   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.693  -6.206   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.068  -4.090   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   30                                                  
CONECT   22   21   23   26   27                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   27                                                       
CONECT   26   22                                                            
CONECT   27   22   25   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   20                                                       
CONECT   30   21   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   18    2                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₈

Average Mass

426.4210 Da

Monoisotopic Mass

426.13147 Da

IUPAC Name

(4R,8R)-2,4-dihydroxy-15-(3-hydroxy-3-methylbutyl)-18-methoxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),5,11,14(19),15,17-heptaen-20-one

Traditional Name

(4R,8R)-2,4-dihydroxy-15-(3-hydroxy-3-methylbutyl)-18-methoxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),5,11,14(19),15,17-heptaen-20-one

CAS Registry Number

Not Available

SMILES

[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C2OC3=C(C(=O)C2=C1O)C(OC)=CC=C3CCC(C)(C)O

InChI Identifier

InChI=1S/C23H22O8/c1-22(2,26)7-6-11-4-5-12(28-3)16-18(24)15-13(30-20(11)16)10-14-17(19(15)25)23(27)8-9-29-21(23)31-14/h4-5,8-10,21,25-27H,6-7H2,1-3H3/t21-,23-/m1/s1

InChI Key

ZICKMRKORQPECB-FYYLOGMGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
ustus NRRL 5856		Not Available

Chemical Taxonomy

Classification

Not classified

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	3.11	ChemAxon
pKa (Strongest Acidic)	8.53	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.02 m³·mol⁻¹	ChemAxon
Polarizability	43.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Asperustin I (NP0332894)

MOL for NP0332894 (Asperustin I)

3D MOL for NP0332894 (Asperustin I)

3D SDF for NP0332894 (Asperustin I)

3D-SDF for NP0332894 (Asperustin I)

PDB for NP0332894 (Asperustin I)

3D PDB for NP0332894 (Asperustin I)

SMILES for NP0332894 (Asperustin I)

INCHI for NP0332894 (Asperustin I)

Structure for NP0332894 (Asperustin I)

3D Structure for NP0332894 (Asperustin I)