NP-MRD: Showing NP-Card for (1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate (NP0221127)

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Record Information

Version

1.0

Created at

2022-09-05 22:37:05 UTC

Updated at

2022-09-05 22:37:05 UTC

NP-MRD ID

NP0221127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate

Description

(1S,2R,4S,5R,6R,7S,9R)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-7-yl (2E)-3-phenylprop-2-enoate belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). (1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate is found in Celastrus orbiculatus. It was first documented in 2022 (PMID: 36075691). Based on a literature review a significant number of articles have been published on (1S,2R,4S,5R,6R,7S,9R)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-7-yl (2E)-3-phenylprop-2-enoate (PMID: 36075690) (PMID: 36075689) (PMID: 36075688) (PMID: 36075687).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062200372D          

 32 35  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309062200372D          

 32 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0221127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](O)[C@H](OC(C)=O)[C@@]2(C)[C@H](C[C@@H]3C[C@]12OC3(C)C)OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O6/c1-16-13-20(28)23(30-17(2)27)25(5)21(14-19-15-26(16,25)32-24(19,3)4)31-22(29)12-11-18-9-7-6-8-10-18/h6-12,16,19-21,23,28H,13-15H2,1-5H3/b12-11+/t16-,19-,20+,21+,23+,25-,26+/m1/s1

> <INCHI_KEY>
TWJNBXBSOPSJCB-VTJPJHEDSA-N

> <FORMULA>
C26H34O6

> <MOLECULAR_WEIGHT>
442.552

> <EXACT_MASS>
442.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.12229430182168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4S,5R,6R,7S,9R)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
3.8982216536666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.135878306123221

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1767668289017017

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
119.63670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,6R,7S,9R)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       6.600   3.820   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.882   2.457   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.703   1.154   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.343   2.398   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.625   1.035   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.464  -0.271   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.002  -0.190   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.767  -1.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.228  -1.751   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.575  -3.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.294  -0.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.177   0.245   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.089   0.802   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.401   2.263   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.200   2.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.900   3.761   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.063   5.054   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.475   4.975   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.764   6.425   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.926   7.718   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.627   9.089   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.790  10.381   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.490  11.753   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.028  11.832   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.866  10.539   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.165   9.168   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.054   0.988   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.788   2.341   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.397  -0.779   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.869  -0.328   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.001  -2.196   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.021  -1.568   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   27   32                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   15    5   11   28                                             
CONECT   28   27                                                            
CONECT   29   13   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   11                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4S,5R,6R,7S,9R)-5-(Acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0,]dodecan-7-yl (2E)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₆H₃₄O₆

Average Mass

442.5520 Da

Monoisotopic Mass

442.23554 Da

IUPAC Name

(1S,2R,4S,5R,6R,7S,9R)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1S,2R,4S,5R,6R,7S,9R)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](O)[C@H](OC(C)=O)[C@@]2(C)[C@H](C[C@@H]3C[C@]12OC3(C)C)OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C26H34O6/c1-16-13-20(28)23(30-17(2)27)25(5)21(14-19-15-26(16,25)32-24(19,3)4)31-22(29)12-11-18-9-7-6-8-10-18/h6-12,16,19-21,23,28H,13-15H2,1-5H3/b12-11+/t16-,19-,20+,21+,23+,25-,26+/m1/s1

InChI Key

TWJNBXBSOPSJCB-VTJPJHEDSA-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
Celastrus orbiculatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Cinnamic acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
Oxepane
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Ether
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	3.9	ChemAxon
pKa (Strongest Acidic)	14.14	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.64 m³·mol⁻¹	ChemAxon
Polarizability	48.12 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	Yes	ChemAxon

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

163189445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
DaVault L: Field Amputations Facilitated by a Surgical Extraction Team. Am Surg. 2022 Sep 8:31348221114521. doi: 10.1177/00031348221114521. [PubMed:36075688 ]
Szanyi J, Walles JK, Tesfaye F, Gudeta AN, Bjorkman P: Intrauterine HIV exposure is associated with linear growth restriction among Ethiopian children in the first 18 months of life. Trop Med Int Health. 2022 Sep;27(9):823-830. doi: 10.1111/tmi.13805. Epub 2022 Aug 17. [PubMed:36075687 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate (NP0221127)

MOL for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0221127 ((1s,2r,4s,5r,6r,7s,9r)-5-(acetyloxy)-4-hydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl (2e)-3-phenylprop-2-enoate)