NP-MRD: Showing NP-Card for (4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione (NP0251968)

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Record Information

Version

2.0

Created at

2022-09-07 15:19:48 UTC

Updated at

2022-09-07 15:19:48 UTC

NP-MRD ID

NP0251968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione

Description

Dankasterone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione was first documented in 2007 (PMID: 17988094). Based on a literature review a significant number of articles have been published on Dankasterone (PMID: 29194412) (PMID: 31624337) (PMID: 34242870) (PMID: 35717801) (PMID: 35630824) (PMID: 33206427).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217192D          

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M  END

     RDKit          3D

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  Mrv1652309072217192D          

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M  END
> <DATABASE_ID>
NP0251968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](C)\C=C\[C@@H](C)[C@H]1CCC(=O)[C@]23CC(=O)C4=CC(=O)CC[C@]4(C)[C@H]2CC[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O3/c1-17(2)18(3)7-8-19(4)21-9-10-25(31)28-16-23(30)22-15-20(29)11-13-26(22,5)24(28)12-14-27(21,28)6/h7-8,15,17-19,21,24H,9-14,16H2,1-6H3/b8-7+/t18-,19-,21-,24-,26+,27-,28+/m1/s1

> <INCHI_KEY>
MHVQURVXZWOWCF-CGIATIRKSA-N

> <FORMULA>
C28H40O3

> <MOLECULAR_WEIGHT>
424.625

> <EXACT_MASS>
424.297745148

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.05041531472763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9R,10R,13R,14R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-9,13-dimethyltetracyclo[8.7.0.0^{1,13}.0^{4,9}]heptadec-4-ene-3,6,17-trione

> <JCHEM_LOGP>
6.283693719333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.611200641895532

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.48892582485483

> <JCHEM_PKA_STRONGEST_BASIC>
-6.570292119799671

> <JCHEM_POLAR_SURFACE_AREA>
51.21

> <JCHEM_REFRACTIVITY>
126.54319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10R,13R,14R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-9,13-dimethyltetracyclo[8.7.0.0^{1,13}.0^{4,9}]heptadec-4-ene-3,6,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.122   2.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.687   1.641   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.486   2.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.453   0.119   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.655  -0.844   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.018  -0.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.784  -1.962   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.651  -2.520   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.884  -4.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.852  -1.557   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.618  -0.035   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.820   0.929   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.066   0.262   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.456   1.334   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.488  -1.152   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.576   0.386   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.952   1.078   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.040   2.616   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.239   0.234   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.615   0.926   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.902   0.082   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.278   0.774   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.815  -1.456   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.439  -2.149   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.152  -1.304   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.064  -2.841   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.776  -1.997   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.371  -3.482   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.832  -3.556   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.287  -2.115   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.193  -3.199   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   27   30                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   15   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   10   15   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₃

Average Mass

424.6250 Da

Monoisotopic Mass

424.29775 Da

IUPAC Name

(1R,9R,10R,13R,14R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-9,13-dimethyltetracyclo[8.7.0.0^{1,13}.0^{4,9}]heptadec-4-ene-3,6,17-trione

Traditional Name

(1R,9R,10R,13R,14R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-9,13-dimethyltetracyclo[8.7.0.0^{1,13}.0^{4,9}]heptadec-4-ene-3,6,17-trione

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](C)\C=C\[C@@H](C)[C@H]1CCC(=O)[C@]23CC(=O)C4=CC(=O)CC[C@]4(C)[C@H]2CC[C@]13C

InChI Identifier

InChI=1S/C28H40O3/c1-17(2)18(3)7-8-19(4)21-9-10-25(31)28-16-23(30)22-15-20(29)11-13-26(22,5)24(28)12-14-27(21,28)6/h7-8,15,17-19,21,24H,9-14,16H2,1-6H3/b8-7+/t18-,19-,21-,24-,26+,27-,28+/m1/s1

InChI Key

MHVQURVXZWOWCF-CGIATIRKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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
logP	6.28	ChemAxon
pKa (Strongest Acidic)	17.49	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.54 m³·mol⁻¹	ChemAxon
Polarizability	50.05 Å³	ChemAxon
Number of Rings	4	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

C00038923

Chemspider ID

8797627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10622263

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Amagata T, Tanaka M, Yamada T, Doi M, Minoura K, Ohishi H, Yamori T, Numata A: Variation in cytostatic constituents of a sponge-derived Gymnascella dankaliensis by manipulating the carbon source. J Nat Prod. 2007 Nov;70(11):1731-40. doi: 10.1021/np070165m. Epub 2007 Nov 8. [PubMed:17988094 ]
Kumla D, Shine Aung T, Buttachon S, Dethoup T, Gales L, Pereira JA, Inacio A, Costa PM, Lee M, Sekeroglu N, Silva AMS, Pinto MMM, Kijjoa A: A New Dihydrochromone Dimer and Other Secondary Metabolites from Cultures of the Marine Sponge-Associated Fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213. Mar Drugs. 2017 Dec 1;15(12). pii: md15120375. doi: 10.3390/md15120375. [PubMed:29194412 ]
Li HL, Li XM, Yang SQ, Cao J, Li YH, Wang BG: Induced terreins production from marine red algal-derived endophytic fungus Aspergillus terreus EN-539 co-cultured with symbiotic fungus Paecilomyces lilacinus EN-531. J Antibiot (Tokyo). 2020 Feb;73(2):108-111. doi: 10.1038/s41429-019-0242-4. Epub 2019 Oct 17. [PubMed:31624337 ]
Ebrahimi KS, Ansari M, Hosseyni Moghaddam MS, Ebrahimi Z, Salehi Z, Shahlaei M, Moradi S: In silico investigation on the inhibitory effect of fungal secondary metabolites on RNA dependent RNA polymerase of SARS-CoV-II: A docking and molecular dynamic simulation study. Comput Biol Med. 2021 Aug;135:104613. doi: 10.1016/j.compbiomed.2021.104613. Epub 2021 Jul 5. [PubMed:34242870 ]
Zhang M, Li Q, Li S, Deng Y, Yu M, Liu J, Qi C, Yang X, Zhu H, Zhang Y: An unprecedented ergostane with a 6/6/5 tricyclic 13(14 --> 8)abeo-8,14-seco skeleton from Talaromyces adpressus. Bioorg Chem. 2022 Oct;127:105943. doi: 10.1016/j.bioorg.2022.105943. Epub 2022 Jun 13. [PubMed:35717801 ]
Guo M, Liang YZ, Cui XM, Shao LJ, Li YF, Yang XY: Four New Sesquiterpenoids from the Rice Fermentation of Antrodiella albocinnamomea. Molecules. 2022 May 23;27(10):3344. doi: 10.3390/molecules27103344. [PubMed:35630824 ]
Chen P, Wang C, Yang R, Xu H, Wu J, Jiang H, Chen K, Ma Z: Asymmetric Total Synthesis of Dankasterones A and B and Periconiastone A Through Radical Cyclization. Angew Chem Int Ed Engl. 2021 Mar 1;60(10):5512-5518. doi: 10.1002/anie.202013881. Epub 2021 Jan 7. [PubMed:33206427 ]
Duecker FL, Heinze RC, Heretsch P: Synthesis of Swinhoeisterol A, Dankasterone A and B, and Periconiastone A by Radical Framework Reconstruction. J Am Chem Soc. 2020 Jan 8;142(1):104-108. doi: 10.1021/jacs.9b12899. Epub 2019 Dec 27. [PubMed:31870147 ]
Ma KX, Shen XT, Huang R, Wang T, Xie XS, Liu SW, Wu SH, Heb J: Bioactive metabolites produced by the endophytic fungus Phomopsis sp. YM355364. Nat Prod Commun. 2014 May;9(5):669-70. [PubMed:25026717 ]
Zhou J, Li G, Deng Q, Zheng D, Yang X, Xu J: Cytotoxic constituents from the mangrove endophytic Pestalotiopsis sp. induce G(0)/G(1) cell cycle arrest and apoptosis in human cancer cells. Nat Prod Res. 2018 Dec;32(24):2968-2972. doi: 10.1080/14786419.2017.1395431. Epub 2017 Oct 31. [PubMed:29086604 ]
LOTUS database [Link]

Showing NP-Card for (4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione (NP0251968)

MOL for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

3D MOL for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

3D SDF for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

3D-SDF for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

PDB for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

3D PDB for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

SMILES for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

INCHI for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

Structure for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)

3D Structure for NP0251968 ((4ar,4br,6ar,7r,10ar)-7-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-4a,6a-dimethyl-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione)