NP-MRD: Showing NP-Card for 16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione (NP0232568)

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Record Information

Version

2.0

Created at

2022-09-06 13:50:47 UTC

Updated at

2022-09-06 13:50:48 UTC

NP-MRD ID

NP0232568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione

Description

Shiraiachrome A belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. 16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione is found in Shiraia bambusicola. 16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione was first documented in 2004 (PMID: 15212963). Based on a literature review a small amount of articles have been published on Shiraiachrome A (PMID: 34207313) (PMID: 32786877).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062215502D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062215502D          

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    2.8891    0.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3308   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7138   -0.0065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  2  0  0  0  0
 16 30  1  0  0  0  0
 28 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  2  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 34 38  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3C(C1=O)C1=C4C(C(OC)=CC1=O)=C(OC)C=C1C4=C3C(C(C(C)=O)C2(C)O)=C(OC)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O10/c1-10(31)25-24-21-17-11(26(33)28(35)29(24)40-6)7-14(37-3)20-15(38-4)9-13(32)19(22(17)20)23-18(21)12(30(25,2)36)8-16(39-5)27(23)34/h7-9,23,25,33,35-36H,1-6H3

> <INCHI_KEY>
LJZXESCNYAMPIB-UHFFFAOYSA-N

> <FORMULA>
C30H26O10

> <MOLECULAR_WEIGHT>
546.528

> <EXACT_MASS>
546.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
55.50947003818676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione

> <JCHEM_LOGP>
-1.726844370666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.620067660021224

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1377086318451988

> <JCHEM_PKA_STRONGEST_BASIC>
-3.308177877155833

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
151.47629999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       9.369   3.908   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.030   4.669   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.702   3.890   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.712   2.350   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.383   1.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.044   2.333   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.716   1.555   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.955   0.033   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.915  -1.102   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.487  -2.532   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.534  -3.743   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.379  -0.997   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.383  -2.336   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.497   0.270   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.018   0.030   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.053   1.744   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.290   2.299   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.300   3.839   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.639   4.600   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.967   3.821   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.029   4.617   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.019   6.157   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.320   6.919   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.330   8.459   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.347   6.936   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.686   6.174   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.015   6.953   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.696   4.634   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.367   3.856   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.377   2.316   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.034   3.873   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.363   4.652   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.353   6.192   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.064  -0.747   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -2.286   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.301  -3.110   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.924  -3.386   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.393   0.032   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.217  -1.269   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.932  -0.012   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7   31                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9   34                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   29                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   31                                                  
CONECT   29   28   21   30                                                  
CONECT   30   29    7   16                                                  
CONECT   31   28    6   32                                                  
CONECT   32   31    3   33                                                  
CONECT   33   32                                                            
CONECT   34    8   35   38                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   34    5   39   40                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Shiraiachrome b	MeSH
Shiraiachrome-a	MeSH
Shiraiachrome-b	MeSH

Chemical Formula

C₃₀H₂₆O₁₀

Average Mass

546.5280 Da

Monoisotopic Mass

546.15260 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3C(C1=O)C1=C4C(C(OC)=CC1=O)=C(OC)C=C1C4=C3C(C(C(C)=O)C2(C)O)=C(OC)C(O)=C1O

InChI Identifier

InChI=1S/C30H26O10/c1-10(31)25-24-21-17-11(26(33)28(35)29(24)40-6)7-14(37-3)20-15(38-4)9-13(32)19(22(17)20)23-18(21)12(30(25,2)36)8-16(39-5)27(23)34/h7-9,23,25,33,35-36H,1-6H3

InChI Key

LJZXESCNYAMPIB-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
Shiraia bambusicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthalene
Anisole
Alkyl aryl ether
Vinylogous ester
Tertiary alcohol
Ketone
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023734

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

3081233

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang L, Wang Z: Natural Products, Alone or in Combination with FDA-Approved Drugs, to Treat COVID-19 and Lung Cancer. Biomedicines. 2021 Jun 18;9(6):689. doi: 10.3390/biomedicines9060689. [PubMed:34207313 ]
Al Subeh ZY, Raja HA, Monro S, Flores-Bocanegra L, El-Elimat T, Pearce CJ, McFarland SA, Oberlies NH: Enhanced Production and Anticancer Properties of Photoactivated Perylenequinones. J Nat Prod. 2020 Aug 28;83(8):2490-2500. doi: 10.1021/acs.jnatprod.0c00492. Epub 2020 Aug 10. [PubMed:32786877 ]
Tong Y, Zhang X, Zhao W, Zhang Y, Lang J, Shi Y, Tan W, Li M, Zhang Y, Tong L, Lu H, Lin L, Ding J: Anti-angiogenic effects of Shiraiachrome A, a compound isolated from a Chinese folk medicine used to treat rheumatoid arthritis. Eur J Pharmacol. 2004 Jun 28;494(2-3):101-9. doi: 10.1016/j.ejphar.2004.04.053. [PubMed:15212963 ]
LOTUS database [Link]

Showing NP-Card for 16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione (NP0232568)

MOL for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

3D MOL for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

3D SDF for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

3D-SDF for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

PDB for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

3D PDB for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

SMILES for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

INCHI for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

Structure for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)

3D Structure for NP0232568 (16-acetyl-12,13,17-trihydroxy-7,9,14,20-tetramethoxy-17-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1,3,6,8,10,12,14,18(23),19-nonaene-5,21-dione)