NP-MRD: Showing NP-Card for (1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate (NP0234588)

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Record Information

Version

2.0

Created at

2022-09-06 16:42:10 UTC

Updated at

2022-09-06 16:42:10 UTC

NP-MRD ID

NP0234588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate

Description

(1S,3R,4R,6S,7R,8S)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]Decan-4-yl acetate belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. (1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate is found in Valeriana jatamansi. Based on a literature review very few articles have been published on (1S,3R,4R,6S,7R,8S)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]Decan-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.7795    1.1028    1.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1230    0.5379    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883    0.9753   -0.5554 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8564   -0.1482   -1.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9619   -1.1857   -1.2343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5678   -2.4271   -1.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577   -0.9944   -0.3361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1734   -0.5694    1.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6366   -1.5931    1.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183    0.0520    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523    0.6785    0.3526 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0506    0.1418    0.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051    0.8883    0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599    0.2707   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953    2.1332    0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0799    0.2823   -0.8192 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8022   -0.0758   -1.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427   -1.4349   -1.5142 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395    1.2333   -1.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4857    1.9281    1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6965    0.8203    2.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9009    1.8676   -0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5464   -1.2346   -2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2275   -2.5243   -1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253   -1.8727   -0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0564   -1.6474    2.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7677   -0.6780    2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1128    0.8611    2.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277    1.7813    0.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5824   -0.7757    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305    0.8710    0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952    0.2157   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    0.8044   -2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2165   -0.2843   -2.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  1
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3 19  1  0
 19 16  1  0
 16 17  1  6
 17 18  1  0
  3  2  1  0
  2  1  2  3
 16 11  1  0
  2  8  1  0
 16  7  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 11 29  1  1
 10 27  1  0
 10 28  1  0
  9 26  1  0
  7 25  1  1
  5 23  1  6
  6 24  1  0
  3 22  1  1
 17 33  1  0
 17 34  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652309062218422D          

 19 21  0  0  1  0            999 V2000
    2.1938   -1.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7317   -0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584   -0.0271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8861    0.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    1.0687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9419    2.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409    0.5303    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9404   -0.4166    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8192   -1.2796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1577   -0.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    0.3393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6694    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828    0.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853   -0.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741    1.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    0.6010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3767    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0033    2.2560    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1693    0.5955    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
  3 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0234588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@]2(O)[C@H]3[C@@H](O)O[C@H](O[C@@]13CCl)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C12H15ClO6/c1-5-10-18-9(15)8-11(5,16)3-7(17-6(2)14)12(8,4-13)19-10/h7-10,15-16H,1,3-4H2,2H3/t7-,8-,9+,10-,11-,12+/m1/s1

> <INCHI_KEY>
ZTKRNEHDDSFTES-RFHDDPBLSA-N

> <FORMULA>
C12H15ClO6

> <MOLECULAR_WEIGHT>
290.7

> <EXACT_MASS>
290.0557159

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.628969765250794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4R,6S,7R,8S)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0^{3,7}]decan-4-yl acetate

> <JCHEM_LOGP>
-0.7192046963333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.650018746100404

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.905151322336451

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4394848173145167

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
62.135600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,6S,7R,8S)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0^{3,7}]decan-4-yl acetate

> <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       4.095  -2.534   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.233  -1.189   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.216  -0.051   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.521   1.749   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.039   1.995   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.758   3.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.196   0.990   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.755  -0.778   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.529  -2.389   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.294  -0.962   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.250   0.633   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.250   1.334   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.768   0.904   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.146  -0.589   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.872   1.978   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.221   1.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.570   2.929   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       3.740   4.211   0.000  0.00  0.00          Cl+0
HETATM   19  O   UNK     0       4.049   1.112   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11    7   17   19                                             
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16    3                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
(1S,3R,4R,6S,7R,8S)-3-(Chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0,]decan-4-yl acetic acid	Generator

Chemical Formula

C₁₂H₁₅ClO₆

Average Mass

290.7000 Da

Monoisotopic Mass

290.05572 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@]2(O)[C@H]3[C@@H](O)O[C@H](O[C@@]13CCl)C2=C

InChI Identifier

InChI=1S/C12H15ClO6/c1-5-10-18-9(15)8-11(5,16)3-7(17-6(2)14)12(8,4-13)19-10/h7-10,15-16H,1,3-4H2,2H3/t7-,8-,9+,10-,11-,12+/m1/s1

InChI Key

ZTKRNEHDDSFTES-RFHDDPBLSA-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
Valeriana jatamansi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Meta-dioxane
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Hemiacetal
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Organohalogen compound
Organochloride
Organooxygen compound
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

163017199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate (NP0234588)

MOL for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

3D MOL for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

3D SDF for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

3D-SDF for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

PDB for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

3D PDB for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

SMILES for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

INCHI for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

Structure for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)

3D Structure for NP0234588 ((1s,3r,4r,6s,7r,8s)-3-(chloromethyl)-6,8-dihydroxy-10-methylidene-2,9-dioxatricyclo[4.3.1.0³,⁷]decan-4-yl acetate)