NP-MRD: Showing NP-Card for A reduced form of preussomerin G at C-2 (NP0332765)

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Record Information

Version

2.0

Created at

2024-04-19 22:03:20 UTC

Updated at

2024-09-16 20:04:58 UTC

NP-MRD ID

NP0332765

Natural Product DOI

https://doi.org/10.57994/2034

Secondary Accession Numbers

None

Natural Product Identification

Common Name

A reduced form of preussomerin G at C-2

Description

(1R,11S,20R)-16,20-dihydroxy-2,12,21-trioxahexacyclo[9.9.1.1¹,¹³.1³,⁷.0¹¹,²³.0¹⁷,²²]Tricosa-3,5,7(23),9,13(22),14,16-heptaene-8,18-dione belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. It was first documented in 2024 (PMID: 38678385). Based on a literature review a significant number of articles have been published on (1R,11S,20R)-16,20-dihydroxy-2,12,21-trioxahexacyclo[9.9.1.1¹,¹³.1³,⁷.0¹¹,²³.0¹⁷,²²]Tricosa-3,5,7(23),9,13(22),14,16-heptaene-8,18-dione (PMID: 38678384) (PMID: 38678383) (PMID: 38678381) (PMID: 38678380).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01022300402D          

 27 32  0  0  1  0            999 V2000
    4.3692   -0.1664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080    0.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494   -0.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2958    0.4948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5494    0.1433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137    1.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409    1.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    2.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695    3.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784    2.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253    2.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967    1.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2415    0.9603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269    1.3517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5137    1.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0217    2.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209    2.7509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6808    3.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    4.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    3.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045    2.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5503    2.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    1.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517    1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    1.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097    2.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    4.1221    0.0000 O   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
  4  3  1  0  0  0  0
  4  5  1  1  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14  7  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
 17 16  1  1  0  0  0
 17  9  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  1  0  0  0  0
 21 22  2  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
 15 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 26  1  0  0  0  0
 20 27  2  0  0  0  0
M  END


  Mrv2104 01022300402D          

 27 32  0  0  1  0            999 V2000
    4.3692   -0.1664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080    0.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494   -0.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2958    0.4948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5494    0.1433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137    1.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409    1.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    2.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695    3.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784    2.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253    2.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967    1.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2415    0.9603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269    1.3517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5137    1.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0217    2.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209    2.7509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6808    3.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    4.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    3.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045    2.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5503    2.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    1.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517    1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    1.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097    2.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    4.1221    0.0000 O   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
  4  3  1  0  0  0  0
  4  5  1  1  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14  7  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
 17 16  1  1  0  0  0
 17  9  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  1  0  0  0  0
 21 22  2  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
 15 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 26  1  0  0  0  0
 20 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC(=O)C2=C3C(O[C@]45O[C@]13OC1=C4C(=CC=C1)C(=O)C=C5)=CC=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O7/c21-10-6-7-19-17-9(10)2-1-3-13(17)26-20(27-19)15(24)8-12(23)16-11(22)4-5-14(25-19)18(16)20/h1-7,15,22,24H,8H2/t15-,19-,20-/m1/s1

> <INCHI_KEY>
JRJROWUNDPTPLP-CDHQVMDDSA-N

> <FORMULA>
C20H12O7

> <MOLECULAR_WEIGHT>
364.309

> <EXACT_MASS>
364.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.54725151827345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10R,11S)-6,10-dihydroxy-2,12,21-trioxahexacyclo[9.9.1.1^{1,13}.1^{3,7}.0^{11,23}.0^{17,22}]tricosa-3,5,7(23),13(22),14,16,19-heptaene-8,18-dione

> <JCHEM_LOGP>
3.1859437786666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.763681795005429

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.800346402896077

> <JCHEM_PKA_STRONGEST_BASIC>
-3.765494383617504

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
91.6404

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10R,11S)-6,10-dihydroxy-2,12,21-trioxahexacyclo[9.9.1.1^{1,13}.1^{3,7}.0^{11,23}.0^{17,22}]tricosa-3,5,7(23),13(22),14,16,19-heptaene-8,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-JAN-23         0                                  
HETATM    1  O   UNK     0       8.156  -0.311   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.922   0.610   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.506  -0.012   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.285   0.924   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.892   0.267   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.119   2.171   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.863   3.136   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.131   4.725   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.796   5.648   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.613   5.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.821   4.284   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.581   2.753   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.784   1.793   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.344   2.523   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.826   1.952   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.774   3.858   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.212   5.135   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.137   6.727   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.856   7.583   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.493   6.856   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.382   5.291   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.027   4.579   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.171   3.035   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.097   2.162   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.506   2.829   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.698   4.433   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.799   7.694   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4                                                            
CONECT    6    2    7   12                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   17                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14    7    4   15   16                                             
CONECT   15   14   25                                                       
CONECT   16   14   17                                                       
CONECT   17   16    9   18   26                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   15   26                                                  
CONECT   26   25   21   17                                                  
CONECT   27   20                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₂O₇

Average Mass

364.3090 Da

Monoisotopic Mass

364.05830 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC(=O)C2=C3C(O[C@]45O[C@]13OC1=C4C(=CC=C1)C(=O)C=C5)=CC=C2O

InChI Identifier

InChI=1S/C20H12O7/c21-10-6-7-19-17-9(10)2-1-3-13(17)26-20(27-19)15(24)8-12(23)16-11(22)4-5-14(25-19)18(16)20/h1-7,15,22,24H,8H2/t15-,19-,20-/m1/s1

InChI Key

JRJROWUNDPTPLP-CDHQVMDDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-04-05	View Spectrum
HMQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-04-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-04-05	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-04-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-04-05	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500, CDCl₃, simulated)	hmasaru@hirosaki-u.ac.jp	HIrosaki Univ.	Masaru Hashimoto	2024-04-05	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
sp. KT4147		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Naphthalene
Tetralin
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Ketal
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Aldehyde
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

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

8242853

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10067313

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Klevebro F, Ash S, Mueller C, Garbarino GM, Gisbertz SS, van Berge Henegouwen MI, Mandeville Y, Ferri L, Davies A, Maynard N, Low DE: Contemporary outcomes of left thoraco-abdominal esophagectomy due to cancer in the esophagus or gastroesophageal junction, a multicenter cohort study. Dis Esophagus. 2024 Apr 28:doae039. doi: 10.1093/dote/doae039. [PubMed:38678385 ]
Liang F, Li G, Guo J, Zhang W, Chang X: Assessing PET/CT's diagnostic accuracy in idiopathic myopathies. Hell J Nucl Med. 2024 Jan-Apr;27(1):46-54. doi: 10.1967/s002449912711. [PubMed:38678384 ]
Okada Y, Zama T, Itonaga T, Mikami R, Okubo M, Sugahara S, Kurooka M, Nakai M, Abe K, Yoshimura M, Saito K: PET/CT findings and dose distribution during radiotherapy in T1N0M0-T2N0M0 glottic cancer. Hell J Nucl Med. 2024 Jan-Apr;27(1):27-34. doi: 10.1967/s002449912710. [PubMed:38678383 ]
Cogno N, Axenie C, Bauer R, Vavourakis V: Agent-based modeling in cancer biomedicine: applications and tools for calibration and validation. Cancer Biol Ther. 2024 Dec 31;25(1):2344600. doi: 10.1080/15384047.2024.2344600. Epub 2024 Apr 28. [PubMed:38678381 ]
Wang Y, Geng Q, Lyu H, Sun W, Fan X, Ma K, Wu K, Wang J, Wang Y, Mei D, Guo C, Xiu P, Pan D, Tao K: Bioinspired Flexible Hydrogelation with Programmable Properties for Tactile Sensing. Adv Mater. 2024 Apr 28:e2401678. doi: 10.1002/adma.202401678. [PubMed:38678380 ]

Showing NP-Card for A reduced form of preussomerin G at C-2 (NP0332765)

MOL for NP0332765 (A reduced form of preussomerin G at C-2)

3D MOL for NP0332765 (A reduced form of preussomerin G at C-2)

3D SDF for NP0332765 (A reduced form of preussomerin G at C-2)

3D-SDF for NP0332765 (A reduced form of preussomerin G at C-2)

PDB for NP0332765 (A reduced form of preussomerin G at C-2)

3D PDB for NP0332765 (A reduced form of preussomerin G at C-2)

SMILES for NP0332765 (A reduced form of preussomerin G at C-2)

INCHI for NP0332765 (A reduced form of preussomerin G at C-2)

Structure for NP0332765 (A reduced form of preussomerin G at C-2)

3D Structure for NP0332765 (A reduced form of preussomerin G at C-2)