NP-MRD: Showing NP-Card for Spiramilactone D (NP0067259)

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Record Information

Version

2.0

Created at

2022-04-28 11:47:10 UTC

Updated at

2022-04-28 11:47:11 UTC

NP-MRD ID

NP0067259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spiramilactone D

Description

(1S,2S,4S,5R,6R,7R,8R,10S,11R)-5,6,8-trihydroxy-5,11-dimethyl-13-oxapentacyclo[9.3.3.2⁴,⁷.0¹,¹⁰.0²,⁷]Nonadecan-12-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Spiramilactone D is found in Spiraea japonica and Spiraea japonica var.acuta. Based on a literature review very few articles have been published on (1S,2S,4S,5R,6R,7R,8R,10S,11R)-5,6,8-trihydroxy-5,11-dimethyl-13-oxapentacyclo[9.3.3.2⁴,⁷.0¹,¹⁰.0²,⁷]Nonadecan-12-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282213472D          

 25 29  0  0  1  0            999 V2000
    4.0912   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708    0.6423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9865   -0.2826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9650   -0.8090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2185   -1.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2572   -1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3132   -1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2447   -0.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8936    0.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1174    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5751   -1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184   -0.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744   -0.7378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0071   -0.1477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5027    0.5804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8725    1.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0270    1.1092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4352    0.5179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0414   -0.0569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7003   -0.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7275    0.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    0.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336    0.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -0.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3389   -1.4915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
  4 11  1  6  0  0  0
  3 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 21  1  0  0  0  0
 18 22  1  6  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  1  0  0  0
 13 25  1  1  0  0  0
M  END


  Mrv1652304282213472D          

 25 29  0  0  1  0            999 V2000
    4.0912   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708    0.6423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9865   -0.2826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9650   -0.8090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2185   -1.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2572   -1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3132   -1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2447   -0.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8936    0.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1174    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5751   -1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184   -0.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744   -0.7378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0071   -0.1477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5027    0.5804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8725    1.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0270    1.1092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4352    0.5179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0414   -0.0569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7003   -0.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7275    0.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    0.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336    0.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -0.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3389   -1.4915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
  4 11  1  6  0  0  0
  3 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 21  1  0  0  0  0
 18 22  1  6  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  1  0  0  0
 13 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(O)[C@H]2CC[C@@]3([C@H](O)C[C@@H]4[C@@]5(C)CCC[C@]4(COC5=O)[C@@H]3C2)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-17-5-3-6-19(10-25-16(17)23)12(17)9-14(21)20-7-4-11(8-13(19)20)18(2,24)15(20)22/h11-15,21-22,24H,3-10H2,1-2H3/t11-,12+,13-,14+,15-,17+,18+,19+,20+/m0/s1

> <INCHI_KEY>
XKEGHAKHUOTXSY-KGMWLRMHSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
35.335398501061384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,5R,6R,7R,8R,10S,11R)-5,6,8-trihydroxy-5,11-dimethyl-13-oxapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadecan-12-one

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
1.0741621043333331

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.447524407413507

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.33034863290139

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974511625123835

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
90.27369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,6R,7R,8R,10S,11R)-5,6,8-trihydroxy-5,11-dimethyl-13-oxapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadecan-12-one

> <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       7.637  -0.250   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.159   1.199   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.308  -0.528   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.135  -1.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.741  -2.166   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.813  -3.704   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       8.051  -2.006   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.657  -0.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.001   1.332   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.552   1.854   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.274  -2.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.434  -1.557   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.859  -1.377   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.613  -0.276   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.538   1.083   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.362   2.220   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.784   2.071   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.679   0.967   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.811  -0.106   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.174  -1.508   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.358   1.758   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.379   0.141   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.543   0.678   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.413  -1.047   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.233  -2.784   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3   10   15                                             
CONECT    3    2    4   12                                                  
CONECT    4    3    5    8   11                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    2                                                       
CONECT   11    4                                                            
CONECT   12    3   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   19   24                                             
CONECT   15   14    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   21   22                                             
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22   18                                                            
CONECT   23   17   24                                                       
CONECT   24   23   14                                                       
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4550 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

(1S,2S,4S,5R,6R,7R,8R,10S,11R)-5,6,8-trihydroxy-5,11-dimethyl-13-oxapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadecan-12-one

Traditional Name

(1S,2S,4S,5R,6R,7R,8R,10S,11R)-5,6,8-trihydroxy-5,11-dimethyl-13-oxapentacyclo[9.3.3.2^{4,7}.0^{1,10}.0^{2,7}]nonadecan-12-one

CAS Registry Number

Not Available

SMILES

C[C@@]1(O)[C@H]2CC[C@@]3([C@H](O)C[C@@H]4[C@@]5(C)CCC[C@]4(COC5=O)[C@@H]3C2)[C@H]1O

InChI Identifier

InChI=1S/C20H30O5/c1-17-5-3-6-19(10-25-16(17)23)12(17)9-14(21)20-7-4-11(8-13(19)20)18(2,24)15(20)22/h11-15,21-22,24H,3-10H2,1-2H3/t11-,12+,13-,14+,15-,17+,18+,19+,20+/m0/s1

InChI Key

XKEGHAKHUOTXSY-KGMWLRMHSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Villanovane, atisane, trachylobane or helvifulvane diterpenoid
Diterpenoid
Diterpene lactone
Atisane diterpenoid
Naphthopyran
Naphthalene
Alkaloid or derivatives
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.72	ALOGPS
logP	1.07	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.27 m³·mol⁻¹	ChemAxon
Polarizability	35.34 Å³	ChemAxon
Number of Rings	5	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

163106572

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Spiramilactone D (NP0067259)

MOL for NP0067259 (Spiramilactone D)

3D MOL for NP0067259 (Spiramilactone D)

3D SDF for NP0067259 (Spiramilactone D)

3D-SDF for NP0067259 (Spiramilactone D)

PDB for NP0067259 (Spiramilactone D)

3D PDB for NP0067259 (Spiramilactone D)

SMILES for NP0067259 (Spiramilactone D)

INCHI for NP0067259 (Spiramilactone D)

Structure for NP0067259 (Spiramilactone D)

3D Structure for NP0067259 (Spiramilactone D)