NP-MRD: Showing NP-Card for (1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate (NP0164176)

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Record Information

Version

2.0

Created at

2022-09-02 23:00:16 UTC

Updated at

2022-09-02 23:00:17 UTC

NP-MRD ID

NP0164176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate

Description

(2R,8S,9R,10S,13R,14R,19S,20S)-20-(acetyloxy)-10,14,18,18-tetramethyl-7-oxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosa-1(21),4-dien-8-yl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate is found in Hyattella intestinalis. Based on a literature review very few articles have been published on (2R,8S,9R,10S,13R,14R,19S,20S)-20-(acetyloxy)-10,14,18,18-tetramethyl-7-oxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosa-1(21),4-dien-8-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201002D          

 33 37  0  0  1  0            999 V2000
    4.7738   -4.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5901   -4.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1947   -3.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3260   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0579    0.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33  8  1  1  0  0  0
  5 33  1  0  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309032201002D          

 33 37  0  0  1  0            999 V2000
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 16 18  2  0  0  0  0
 19 14  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 12  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33  8  1  1  0  0  0
  5 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1OCC2=CC[C@H]3C4=C[C@H](OC(C)=O)[C@H]5C(C)(C)CCC[C@]5(C)[C@H]4CC[C@]3(C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O5/c1-16(29)32-22-14-19-20-9-8-18-15-31-25(33-17(2)30)23(18)27(20,5)13-10-21(19)28(6)12-7-11-26(3,4)24(22)28/h8,14,20-25H,7,9-13,15H2,1-6H3/t20-,21-,22-,23+,24-,25-,27-,28+/m0/s1

> <INCHI_KEY>
JCJGAZKXOUBQBW-BLAWCALFSA-N

> <FORMULA>
C28H40O5

> <MOLECULAR_WEIGHT>
456.623

> <EXACT_MASS>
456.287574388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.49260099765472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,8S,9R,10S,13R,14R,19S,20S)-20-(acetyloxy)-10,14,18,18-tetramethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-1(21),4-dien-8-yl acetate

> <ALOGPS_LOGP>
5.65

> <JCHEM_LOGP>
4.388826874333331

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.352863469289699

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
126.81099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,8S,9R,10S,13R,14R,19S,20S)-20-(acetyloxy)-10,14,18,18-tetramethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-1(21),4-dien-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.911  -9.177   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.568  -7.676   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.096  -7.223   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.697  -6.628   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.354  -5.127   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.937  -4.522   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.075  -2.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.576  -2.645   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.326  -1.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.866  -1.277   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.656  -2.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.196  -2.575   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.946  -1.230   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.485  -1.206   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.235   0.139   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      18.775   0.162   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.524   1.508   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.565  -1.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      17.276  -2.528   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.815  -2.505   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.525  -0.992   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.254  -1.956   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.606  -3.827   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.856  -5.172   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.316  -5.195   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.526  -3.873   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.776  -5.219   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.986  -3.897   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.236  -5.242   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.697  -5.265   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.906  -3.944   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.157  -5.289   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.367  -3.967   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   26                                                  
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   19   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   12   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   11   32   33                                             
CONECT   32   31                                                            
CONECT   33   31    8    5                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2R,8S,9R,10S,13R,14R,19S,20S)-20-(Acetyloxy)-10,14,18,18-tetramethyl-7-oxapentacyclo[11.8.0.0,.0,.0,]henicosa-1(21),4-dien-8-yl acetic acid	Generator

Chemical Formula

C₂₈H₄₀O₅

Average Mass

456.6230 Da

Monoisotopic Mass

456.28757 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1OCC2=CC[C@H]3C4=C[C@H](OC(C)=O)[C@H]5C(C)(C)CCC[C@]5(C)[C@H]4CC[C@]3(C)[C@@H]12

InChI Identifier

InChI=1S/C28H40O5/c1-16(29)32-22-14-19-20-9-8-18-15-31-25(33-17(2)30)23(18)27(20,5)13-10-21(19)28(6)12-7-11-26(3,4)24(22)28/h8,14,20-25H,7,9-13,15H2,1-6H3/t20-,21-,22-,23+,24-,25-,27-,28+/m0/s1

InChI Key

JCJGAZKXOUBQBW-BLAWCALFSA-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
Hyattella intestinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Steroid
16-oxasteroid
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
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

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

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

163015174

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate (NP0164176)

MOL for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

3D MOL for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

3D SDF for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

3D-SDF for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

PDB for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

3D PDB for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

SMILES for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

INCHI for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

Structure for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)

3D Structure for NP0164176 ((1s,5ar,7s,7as,11ar,11br,13as,13br)-7-(acetyloxy)-8,8,11a,13a-tetramethyl-1h,3h,5h,5ah,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-1-yl acetate)