NP-MRD: Showing NP-Card for (1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one (NP0286614)

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Record Information

Version

2.0

Created at

2022-09-09 15:15:37 UTC

Updated at

2022-09-09 15:15:37 UTC

NP-MRD ID

NP0286614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

Description

(1R,8S,9S,10S)-8-hydroxy-3,4-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]Hexadeca-2(7),3,5-trien-15-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one is found in Salvia columbariae. Based on a literature review very few articles have been published on (1R,8S,9S,10S)-8-hydroxy-3,4-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]Hexadeca-2(7),3,5-trien-15-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092217152D          

 27 30  0  0  1  0            999 V2000
    6.2280    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4049    1.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9453    0.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089    0.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1320    0.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916    0.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4956   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8494   -0.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0262   -0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6626    0.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1222    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586    1.6989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182    2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570    0.4507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2595    1.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681    0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741   -0.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8715   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074   -1.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2383   -1.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -0.3512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8710   -1.4030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2221   -0.8935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159   -0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699    0.2837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6739   -1.2134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1932   -1.8545    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 14  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 14 24  1  1  0  0  0
 24 25  2  0  0  0  0
 22 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END


  Mrv1652309092217152D          

 27 30  0  0  1  0            999 V2000
    6.2280    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4049    1.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9453    0.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089    0.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1320    0.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916    0.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4956   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8494   -0.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0262   -0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6626    0.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1222    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586    1.6989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182    2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570    0.4507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2595    1.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681    0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741   -0.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8715   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074   -1.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2383   -1.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -0.3512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8710   -1.4030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2221   -0.8935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159   -0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699    0.2837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6739   -1.2134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1932   -1.8545    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 14  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 14 24  1  1  0  0  0
 24 25  2  0  0  0  0
 22 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0286614

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=C2[C@H](O)[C@H]3OC(=O)[C@@]4(CCCC(C)(C)[C@H]34)C2=C1OC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-11(2)12-10-13-14(17(26-6)16(12)25-5)22-9-7-8-21(3,4)19(22)18(15(13)23)27-20(22)24/h10-11,15,18-19,23H,7-9H2,1-6H3/t15-,18+,19-,22-/m0/s1

> <INCHI_KEY>
WLRZIPVGEMNPES-AKYGZRSFSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.16692136506927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,9S,10S)-8-hydroxy-3,4-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one

> <JCHEM_LOGP>
3.8701323773333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.370357004663202

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5116058461603146

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
101.67819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,9S,10S)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      11.626   2.861   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.089   2.964   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.231   1.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.910   0.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.446   0.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.304   1.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.125  -1.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.052  -0.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.516  -0.872   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.837   0.510   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.695   1.789   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.016   3.171   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.874   4.450   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.333   0.841   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.218   1.903   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.740   1.469   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.378  -0.028   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.493  -1.090   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.254  -2.004   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.178  -2.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.971  -0.656   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.359  -2.619   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.148  -1.668   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.136  -0.128   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.744   0.530   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.858  -2.265   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.827  -3.462   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   10   15   21   24                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   14   22                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   14   25                                                  
CONECT   25   24                                                            
CONECT   26   22    9   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(1R,8S,9S,10S)-8-hydroxy-3,4-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one

Traditional Name

(1R,8S,9S,10S)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one

CAS Registry Number

Not Available

SMILES

COC1=C(C=C2[C@H](O)[C@H]3OC(=O)[C@@]4(CCCC(C)(C)[C@H]34)C2=C1OC)C(C)C

InChI Identifier

InChI=1S/C22H30O5/c1-11(2)12-10-13-14(17(26-6)16(12)25-5)22-9-7-8-21(3,4)19(22)18(15(13)23)27-20(22)24/h10-11,15,18-19,23H,7-9H2,1-6H3/t15-,18+,19-,22-/m0/s1

InChI Key

WLRZIPVGEMNPES-AKYGZRSFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia columbariae	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
Phenanthrene
Benzoxepine
Tetralin
Anisole
Alkyl aryl ether
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	3.87	ChemAxon
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-3.5	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	3	ChemAxon
Refractivity	101.68 m³·mol⁻¹	ChemAxon
Polarizability	41.17 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	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

163015381

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one (NP0286614)

MOL for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D MOL for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D SDF for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D-SDF for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

PDB for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D PDB for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

SMILES for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

INCHI for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

Structure for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D Structure for NP0286614 ((1r,8s,9s,10s)-8-hydroxy-5-isopropyl-3,4-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)