NP-MRD: Showing NP-Card for Spiramacetal (NP0067253)

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Record Information

Version

2.0

Created at

2022-04-28 11:46:39 UTC

Updated at

2022-04-28 11:46:39 UTC

NP-MRD ID

NP0067253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spiramacetal

Description

(1R,5S,6R,8S,10S,11S,14S,16R,17R,18S)-6-hydroxy-5,13-dimethyl-7,9-dioxahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]Icos-12-en-18-yl acetate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. Spiramacetal is found in Spiraea japonica and Spiraea japonica var.acuta. Based on a literature review very few articles have been published on (1R,5S,6R,8S,10S,11S,14S,16R,17R,18S)-6-hydroxy-5,13-dimethyl-7,9-dioxahexacyclo[8.6.2.2¹¹,¹⁴.0¹,⁸.0⁵,¹⁷.0¹¹,¹⁶]Icos-12-en-18-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282213462D          

 27 32  0  0  1  0            999 V2000
    7.8011    1.4851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7666    0.6420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0495   -0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4728   -0.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6433   -0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2029    0.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4055    1.1046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9928    1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    1.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2015    1.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9747    0.6764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9000    0.5160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8242   -0.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7835   -1.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4786   -1.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511   -1.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6158    0.3902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9426    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0338   -0.9429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8775   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291   -0.1622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2550   -0.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6672    0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6573    0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4483    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  7  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
  2 12  1  0  0  0  0
  6 12  1  0  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
  6 22  1  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 24  1  0  0  0  0
 23 25  1  0  0  0  0
  2 26  1  6  0  0  0
  1 27  1  1  0  0  0
M  END


  Mrv1652304282213462D          

 27 32  0  0  1  0            999 V2000
    7.8011    1.4851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7666    0.6420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0495   -0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4728   -0.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6433   -0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2029    0.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4055    1.1046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9928    1.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    1.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2015    1.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9747    0.6764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9000    0.5160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8242   -0.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7835   -1.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4786   -1.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511   -1.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6158    0.3902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9426    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0338   -0.9429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8775   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291   -0.1622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2550   -0.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6672    0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6573    0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4483    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  7  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
  2 12  1  0  0  0  0
  6 12  1  0  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
  6 22  1  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 24  1  0  0  0  0
 23 25  1  0  0  0  0
  2 26  1  6  0  0  0
  1 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@H]2O[C@H]3O[C@@H](O)[C@@]4(C)CCC[C@@]3([C@@H]3C[C@@H]5CC[C@@]23C=C5C)[C@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-11-10-21-8-5-13(11)9-14(21)22-7-4-6-20(3)16(22)15(25-12(2)23)17(21)26-19(22)27-18(20)24/h10,13-19,24H,4-9H2,1-3H3/t13-,14+,15-,16+,17+,18+,19-,20-,21-,22+/m0/s1

> <INCHI_KEY>
BCVUSHCDLNESII-CDPATKTDSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.220178682968296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,6R,8S,10S,11S,14S,16R,17R,18S)-6-hydroxy-5,13-dimethyl-7,9-dioxahexacyclo[8.6.2.2^{11,14}.0^{1,8}.0^{5,17}.0^{11,16}]icos-12-en-18-yl acetate

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
2.8049859093333334

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.890925019638228

> <JCHEM_PKA_STRONGEST_BASIC>
-4.135133361150223

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
97.25939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,6R,8S,10S,11S,14S,16R,17R,18S)-6-hydroxy-5,13-dimethyl-7,9-dioxahexacyclo[8.6.2.2^{11,14}.0^{1,8}.0^{5,17}.0^{11,16}]icos-12-en-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      14.562   2.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.498   1.198   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.026  -0.268   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.949  -1.411   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.401  -1.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.579   0.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.957   2.062   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.053   3.250   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      10.721   3.112   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.709   1.946   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.153   1.263   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.880   0.963   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.872  -0.595   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.796  -2.271   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.093  -3.100   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.429  -2.980   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.616   0.728   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.360   1.485   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.796  -0.214   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.530  -1.760   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.105  -1.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.948  -0.303   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.076  -1.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.846   0.342   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.553  -1.679   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.160   1.439   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.770   3.910   0.000  0.00  0.00           O+0
CONECT    1    2    8   27                                                  
CONECT    2    1    3   12   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12   22                                             
CONECT    7    6    8    9                                                  
CONECT    8    7    1                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    2    6                                                  
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10   18   22   24                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21    6   17                                                  
CONECT   23   20   24   25                                                  
CONECT   24   23   17                                                       
CONECT   25   23                                                            
CONECT   26    2                                                            
CONECT   27    1                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1R,5S,6R,8S,10S,11S,14S,16R,17R,18S)-6-Hydroxy-5,13-dimethyl-7,9-dioxahexacyclo[8.6.2.2,.0,.0,.0,]icos-12-en-18-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(1R,5S,6R,8S,10S,11S,14S,16R,17R,18S)-6-hydroxy-5,13-dimethyl-7,9-dioxahexacyclo[8.6.2.2^{11,14}.0^{1,8}.0^{5,17}.0^{11,16}]icos-12-en-18-yl acetate

Traditional Name

(1R,5S,6R,8S,10S,11S,14S,16R,17R,18S)-6-hydroxy-5,13-dimethyl-7,9-dioxahexacyclo[8.6.2.2^{11,14}.0^{1,8}.0^{5,17}.0^{11,16}]icos-12-en-18-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@H]2O[C@H]3O[C@@H](O)[C@@]4(C)CCC[C@@]3([C@@H]3C[C@@H]5CC[C@@]23C=C5C)[C@H]14

InChI Identifier

InChI=1S/C22H30O5/c1-11-10-21-8-5-13(11)9-14(21)22-7-4-6-20(3)16(22)15(25-12(2)23)17(21)26-19(22)27-18(20)24/h10,13-19,24H,4-9H2,1-3H3/t13-,14+,15-,16+,17+,18+,19-,20-,21-,22+/m0/s1

InChI Key

BCVUSHCDLNESII-CDPATKTDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Spiraea japonica	LOTUS Database	35616633
Spiraea japonica var.acuta	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Naphthopyran
Naphthalene
Alkaloid or derivatives
Pyran
Oxane
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
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
logP	1.74	ALOGPS
logP	2.8	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.89	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.26 m³·mol⁻¹	ChemAxon
Polarizability	39.22 Å³	ChemAxon
Number of Rings	6	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

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

163103478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Spiramacetal (NP0067253)

MOL for NP0067253 (Spiramacetal)

3D MOL for NP0067253 (Spiramacetal)

3D SDF for NP0067253 (Spiramacetal)

3D-SDF for NP0067253 (Spiramacetal)

PDB for NP0067253 (Spiramacetal)

3D PDB for NP0067253 (Spiramacetal)

SMILES for NP0067253 (Spiramacetal)

INCHI for NP0067253 (Spiramacetal)

Structure for NP0067253 (Spiramacetal)

3D Structure for NP0067253 (Spiramacetal)