NP-MRD: Showing NP-Card for crisamicin a (NP0321038)

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Record Information

Version

2.0

Created at

2022-09-11 23:02:01 UTC

Updated at

2022-09-11 23:02:01 UTC

NP-MRD ID

NP0321038

Secondary Accession Numbers

None

Natural Product Identification

Common Name

crisamicin a

Description

Crisamicin A, also known as CRS-a, belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. crisamicin a is found in Micromonospora purpureochromogenes. crisamicin a was first documented in 2003 (PMID: 14685324). Based on a literature review a significant number of articles have been published on Crisamicin A (PMID: 25677470) (PMID: 32298125) (PMID: 25029027) (PMID: 18553973) (PMID: 12945899).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122201022D          

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M  END

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   -5.3567   -2.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4649   -3.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154   -2.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0913   -4.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -4.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466   -3.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  2  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 35 34  1  6  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  1  0  0  0
 16 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 14 42  1  0  0  0  0
 42 43  1  0  0  0  0
 10 43  1  0  0  0  0
 43 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0321038

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@H]2CC(=O)O[C@H]2C2=C1C(=O)C1=CC(=CC(O)=C1C2=O)C1=CC(O)=C2C(=O)C3=C([C@H](C)O[C@H]4CC(=O)O[C@@H]34)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H22O12/c1-9-21-25(31-17(41-9)7-19(35)43-31)29(39)23-13(27(21)37)3-11(5-15(23)33)12-4-14-24(16(34)6-12)30(40)26-22(28(14)38)10(2)42-18-8-20(36)44-32(18)26/h3-6,9-10,17-18,31-34H,7-8H2,1-2H3/t9-,10-,17-,18-,31+,32+/m0/s1

> <INCHI_KEY>
IPAXVRZEFNMCLP-GJPLRXPFSA-N

> <FORMULA>
C32H22O12

> <MOLECULAR_WEIGHT>
598.516

> <EXACT_MASS>
598.111126148

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
59.37807602884079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11S,15S,17S)-7-hydroxy-5-[(11S,15S,17S)-7-hydroxy-17-methyl-2,9,13-trioxo-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3,5,7-tetraen-5-yl]-17-methyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3,5,7-tetraene-2,9,13-trione

> <JCHEM_LOGP>
2.588957923333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.922347479728981

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3110006692805465

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9198366518147227

> <JCHEM_POLAR_SURFACE_AREA>
179.79999999999998

> <JCHEM_REFRACTIVITY>
147.6

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(11S,15S,17S)-7-hydroxy-5-[(11S,15S,17S)-7-hydroxy-17-methyl-2,9,13-trioxo-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3,5,7-tetraen-5-yl]-17-methyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3,5,7-tetraene-2,9,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.819 -13.019   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.285 -11.552   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.789 -11.221   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.255  -9.753   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.658  -9.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.486  -7.587   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.624  -6.549   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.978  -7.277   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.217  -8.616   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.713  -8.946   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.247 -10.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.743 -10.745   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.277 -12.213   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.295  -9.607   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.800  -9.938   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.838  -8.800   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.342  -9.131   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.808 -10.599   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.312 -10.929   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.778 -12.397   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -7.350  -9.792   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.884  -8.324   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.380  -7.994   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.923  -7.187   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -7.457  -5.719   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -9.427  -7.517   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.893  -8.985   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.854 -10.122   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.320 -11.590   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -11.397  -9.316   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -12.158 -10.655   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -13.666 -10.345   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -14.803 -11.383   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -13.837  -8.814   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -12.435  -8.178   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -11.969  -6.710   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -10.465  -6.380   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.999  -4.912   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.372  -7.333   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.868  -7.002   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -0.402  -5.534   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.170  -8.140   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.675  -7.809   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.140  -6.341   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   43                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   42                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   39                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   17                                                       
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   37                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   21   29                                                  
CONECT   29   28                                                            
CONECT   30   27   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   30   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   26   38                                                  
CONECT   38   37                                                            
CONECT   39   16   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   14   43                                                  
CONECT   43   42   10   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  102    0
END

View in JSmol

Synonyms

Value	Source
CRS-a	MeSH

Chemical Formula

C₃₂H₂₂O₁₂

Average Mass

598.5160 Da

Monoisotopic Mass

598.11113 Da

IUPAC Name

(11S,15S,17S)-7-hydroxy-5-[(11S,15S,17S)-7-hydroxy-17-methyl-2,9,13-trioxo-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3,5,7-tetraen-5-yl]-17-methyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3,5,7-tetraene-2,9,13-trione

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H]2CC(=O)O[C@H]2C2=C1C(=O)C1=CC(=CC(O)=C1C2=O)C1=CC(O)=C2C(=O)C3=C([C@H](C)O[C@H]4CC(=O)O[C@@H]34)C(=O)C2=C1

InChI Identifier

InChI=1S/C32H22O12/c1-9-21-25(31-17(41-9)7-19(35)43-31)29(39)23-13(27(21)37)3-11(5-15(23)33)12-4-14-24(16(34)6-12)30(40)26-22(28(14)38)10(2)42-18-8-20(36)44-32(18)26/h3-6,9-10,17-18,31-34H,7-8H2,1-2H3/t9-,10-,17-,18-,31+,32+/m0/s1

InChI Key

IPAXVRZEFNMCLP-GJPLRXPFSA-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 purpureochromogenes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Not Available

Direct Parent

Lignan lactones

Alternative Parents

Substituents

Lignan lactone
Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Furopyran
Quinone
Aryl ketone
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Vinylogous acid
Oxolane
Furan
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxygen 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	2.59	ChemAxon
pKa (Strongest Acidic)	7.31	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	179.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	147.6 m³·mol⁻¹	ChemAxon
Polarizability	59.38 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	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

C00016000

Chemspider ID

21374345

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25023403

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mulay SV, Fernandes RA: Synthetic studies on actinorhodin and gamma-actinorhodin: synthesis of deoxyactinorhodin and deoxy-gamma-actinorhodin/crisamicin A isomer. Chemistry. 2015 Mar 16;21(12):4842-52. doi: 10.1002/chem.201406431. Epub 2015 Feb 11. [PubMed:25677470 ]
Kopp J, Bruckner R: Stereoselective Total Synthesis of the Dimeric Naphthoquinonopyrano-gamma-lactone (-)-Crisamicin A: Introducing the Dimerization Site by a Late-Stage Hartwig Borylation. Org Lett. 2020 May 1;22(9):3607-3612. doi: 10.1021/acs.orglett.0c01078. Epub 2020 Apr 16. [PubMed:32298125 ]
Brimble MA, Hassan NP, Naysmith BJ, Sperry J: Toward an asymmetric synthesis of the dimeric pyranonaphthoquinone antibiotic crisamicin A. J Org Chem. 2014 Aug 1;79(15):7169-78. doi: 10.1021/jo501344c. Epub 2014 Jul 23. [PubMed:25029027 ]
Li Z, Gao Y, Tang Y, Dai M, Wang G, Wang Z, Yang Z: Total synthesis of crisamicin A. Org Lett. 2008 Jul 17;10(14):3017-20. doi: 10.1021/ol800977n. Epub 2008 Jun 14. [PubMed:18553973 ]
Brimble MA, Lai MY: Synthesis of regioisomeric analogues of crisamicin A. Org Biomol Chem. 2003 Dec 7;1(23):4227-34. doi: 10.1039/b309722f. Epub 2003 Oct 29. [PubMed:14685324 ]
Brimble MA, Lai MY: Suzuki-Miyaura homocoupling of naphthyl triflates using bis(pinacolato)diboron: approaches to the biaryl skeleton of crisamicin A. Org Biomol Chem. 2003 Jun 21;1(12):2084-95. doi: 10.1039/b303070a. [PubMed:12945899 ]
LOTUS database [Link]

Showing NP-Card for crisamicin a (NP0321038)

MOL for NP0321038 (crisamicin a)

3D MOL for NP0321038 (crisamicin a)

3D SDF for NP0321038 (crisamicin a)

3D-SDF for NP0321038 (crisamicin a)

PDB for NP0321038 (crisamicin a)

3D PDB for NP0321038 (crisamicin a)

SMILES for NP0321038 (crisamicin a)

INCHI for NP0321038 (crisamicin a)

Structure for NP0321038 (crisamicin a)

3D Structure for NP0321038 (crisamicin a)