NP-MRD: Showing NP-Card for (3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one (NP0257933)

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Record Information

Version

2.0

Created at

2022-09-07 23:12:12 UTC

Updated at

2022-09-07 23:12:13 UTC

NP-MRD ID

NP0257933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one

Description

Dicitrinone B belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one is found in Penicillium citrinum. (3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one was first documented in 2014 (PMID: 24699111). Based on a literature review very few articles have been published on Dicitrinone B (PMID: 36052845).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082201122D          

 32 35  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082201122D          

 32 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0257933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OC=C2C1=O)C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O6/c1-10-15(6)31-8-17-19(10)13(4)23(27)21(25(17)29)12(3)22-24(28)14(5)20-11(2)16(7)32-9-18(20)26(22)30/h8-12,15-16,27-28H,1-7H3/t10-,11-,15-,16-/m1/s1

> <INCHI_KEY>
WUZQRRXRWONUET-HOJOPBEUSA-N

> <FORMULA>
C26H30O6

> <MOLECULAR_WEIGHT>
438.52

> <EXACT_MASS>
438.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.743936391133005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S)-6-hydroxy-7-{1-[(3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-4,8-dihydro-3H-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-4,8-dihydro-3H-2-benzopyran-8-one

> <JCHEM_LOGP>
2.613244062666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.174704608130148

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.476503789196586

> <JCHEM_PKA_STRONGEST_BASIC>
-4.494031926597896

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
125.21799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S)-6-hydroxy-7-{1-[(3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.198   2.471   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9                                                            
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   31                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   29                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21   28                                                  
CONECT   28   27                                                            
CONECT   29   22   16   30                                                  
CONECT   30   29                                                            
CONECT   31   13    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₆

Average Mass

438.5200 Da

Monoisotopic Mass

438.20424 Da

IUPAC Name

(3R,4S)-6-hydroxy-7-{1-[(3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-4,8-dihydro-3H-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-4,8-dihydro-3H-2-benzopyran-8-one

Traditional Name

(3R,4S)-6-hydroxy-7-{1-[(3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one

CAS Registry Number

Not Available

SMILES

CC(C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OC=C2C1=O)C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OC=C2C1=O

InChI Identifier

InChI=1S/C26H30O6/c1-10-15(6)31-8-17-19(10)13(4)23(27)21(25(17)29)12(3)22-24(28)14(5)20-11(2)16(7)32-9-18(20)26(22)30/h8-12,15-16,27-28H,1-7H3/t10-,11-,15-,16-/m1/s1

InChI Key

WUZQRRXRWONUET-HOJOPBEUSA-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
Penicillium citrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Vinylogous ester
Vinylogous acid
Ketone
Oxacycle
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.61	ChemAxon
pKa (Strongest Acidic)	5.48	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	125.22 m³·mol⁻¹	ChemAxon
Polarizability	47.74 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052933

Chemspider ID

78438110

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50924225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Q, Yang Y, Cheng M, Cheng F, Chen S, Zheng Q, Sun Y, Chen L: The marine natural product, dicitrinone B, induces apoptosis through autophagy blockade in breast cancer. Int J Mol Med. 2022 Oct;50(4):130. doi: 10.3892/ijmm.2022.5186. Epub 2022 Sep 2. [PubMed:36052845 ]
Chen L, Gong MW, Peng ZF, Zhou T, Ying MG, Zheng QH, Liu QY, Zhang QQ: The marine fungal metabolite, dicitrinone B, induces A375 cell apoptosis through the ROS-related caspase pathway. Mar Drugs. 2014 Apr 2;12(4):1939-58. doi: 10.3390/md12041939. [PubMed:24699111 ]
LOTUS database [Link]

Showing NP-Card for (3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one (NP0257933)

MOL for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

3D MOL for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

3D SDF for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

3D-SDF for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

PDB for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

3D PDB for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

SMILES for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

INCHI for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

Structure for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)

3D Structure for NP0257933 ((3r,4s)-6-hydroxy-7-{1-[(3r,4s)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-yl]ethyl}-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-8-one)