NP-MRD: Showing NP-Card for (1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate (NP0191840)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 08:55:10 UTC

Updated at

2022-09-04 08:55:10 UTC

NP-MRD ID

NP0191840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate

Description

(1S,4S,8R,9R,12S,13S,14S,16S,18R)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]Nonadecan-18-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate is found in Isodon henryi. Based on a literature review very few articles have been published on (1S,4S,8R,9R,12S,13S,14S,16S,18R)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]Nonadecan-18-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042210552D          

 29 33  0  0  1  0            999 V2000
    5.2280   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4429    0.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706    1.0431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6320    1.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889    1.6307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3053    2.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4105    0.8290    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9748    0.1720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5780    0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809   -0.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722   -1.2362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7701   -0.7302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727   -0.0772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5275   -0.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    1.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122    0.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6805    1.1635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6770    2.0005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0154    2.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630    2.2318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8806    1.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600    0.7619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7392   -0.2813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7760   -1.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5081   -1.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2035   -1.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5448   -2.3099    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  6  0  0  0
  8  9  1  6  0  0  0
  3  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 13 24  1  0  0  0  0
  7 24  1  0  0  0  0
 19 24  1  0  0  0  0
  8 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END


  Mrv1652309042210552D          

 29 33  0  0  1  0            999 V2000
    5.2280   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4429    0.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706    1.0431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6320    1.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889    1.6307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3053    2.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4105    0.8290    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9748    0.1720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5780    0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809   -0.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722   -1.2362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7701   -0.7302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727   -0.0772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5275   -0.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    1.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122    0.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6805    1.1635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6770    2.0005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0154    2.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630    2.2318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8806    1.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600    0.7619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7392   -0.2813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7760   -1.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5081   -1.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2035   -1.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5448   -2.3099    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  6  0  0  0
  8  9  1  6  0  0  0
  3  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 13 24  1  0  0  0  0
  7 24  1  0  0  0  0
 19 24  1  0  0  0  0
  8 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0191840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C(=C)[C@H]2C[C@]11[C@@H]([C@@H](O)C2)[C@@]23CO[C@@H](O)[C@@H]2C(C)(C)CC[C@@H]3OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O7/c1-10-12-7-13(24)15-21(8-12,17(10)28-11(2)23)19(26)29-14-5-6-20(3,4)16-18(25)27-9-22(14,15)16/h12-18,24-25H,1,5-9H2,2-4H3/t12-,13+,14+,15-,16-,17-,18-,21+,22+/m1/s1

> <INCHI_KEY>
JUJKSMRAYVDOKO-JFRMTHNBSA-N

> <FORMULA>
C22H30O7

> <MOLECULAR_WEIGHT>
406.475

> <EXACT_MASS>
406.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.92968998828917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,8R,9R,12S,13S,14S,16S,18R)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{8,12}]nonadecan-18-yl acetate

> <JCHEM_LOGP>
0.8063065853333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.861147613061721

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.14535905757664

> <JCHEM_PKA_STRONGEST_BASIC>
-2.859990298176437

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
100.496

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,8R,9R,12S,13S,14S,16S,18R)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{8,12}]nonadecan-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       9.759  -0.052   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.293   0.421   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.785   1.947   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.780   3.238   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.206   3.044   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.303   4.292   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.500   1.547   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.553   0.321   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.679   1.251   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.818  -1.070   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.735  -2.308   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.304  -1.363   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.376  -0.144   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.985  -0.882   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.271  -0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.170   1.532   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.561   3.022   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.703   1.386   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.270   2.172   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.264   3.734   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.029   4.654   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.731   4.166   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.510   2.851   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.725   1.422   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.980  -0.525   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.048  -2.064   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.415  -2.773   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.713  -1.945   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.484  -4.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9   10   25                                             
CONECT    9    8    3                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   13    7   19                                             
CONECT   25    8    2   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
(1S,4S,8R,9R,12S,13S,14S,16S,18R)-9,14-Dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0,.0,.0,]nonadecan-18-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₇

Average Mass

406.4750 Da

Monoisotopic Mass

406.19915 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C(=C)[C@H]2C[C@]11[C@@H]([C@@H](O)C2)[C@@]23CO[C@@H](O)[C@@H]2C(C)(C)CC[C@@H]3OC1=O

InChI Identifier

InChI=1S/C22H30O7/c1-10-12-7-13(24)15-21(8-12,17(10)28-11(2)23)19(26)29-14-5-6-20(3,4)16-18(25)27-9-22(14,15)16/h12-18,24-25H,1,5-9H2,2-4H3/t12-,13+,14+,15-,16-,17-,18-,21+,22+/m1/s1

InChI Key

JUJKSMRAYVDOKO-JFRMTHNBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon henryi	LOTUS Database	35616633

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

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Tetrahydrofuran
Lactone
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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

162955934

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate (NP0191840)

MOL for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

3D MOL for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

3D SDF for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

3D-SDF for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

PDB for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

3D PDB for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

SMILES for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

INCHI for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

Structure for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)

3D Structure for NP0191840 ((1s,4s,8r,9r,12s,13s,14s,16s,18r)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-2-oxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-18-yl acetate)