NP-MRD: Showing NP-Card for (1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione (NP0219672)

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Record Information

Version

2.0

Created at

2022-09-05 20:44:45 UTC

Updated at

2022-09-05 20:44:45 UTC

NP-MRD ID

NP0219672

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione

Description

CHEMBL3581360 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione is found in Teucrium viscidum. Based on a literature review very few articles have been published on CHEMBL3581360.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222442D          

 24 27  0  0  1  0            999 V2000
    6.6019   -0.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3541    0.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009    1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4955    1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    1.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281   -0.3724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911    0.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389   -0.7301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.8569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6440    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5104    1.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8639    2.1793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0148    2.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.5486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5584    1.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7006    2.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7821    1.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426    0.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5143    0.0666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1450   -0.6711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495    0.2217    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12  7  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 12 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 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 12 24  1  0  0  0  0
M  END


  Mrv1652309052222442D          

 24 27  0  0  1  0            999 V2000
    6.6019   -0.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3541    0.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009    1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4955    1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    1.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281   -0.3724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911    0.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389   -0.7301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.8569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6440    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5104    1.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8639    2.1793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0148    2.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.5486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5584    1.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7006    2.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7821    1.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426    0.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5143    0.0666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1450   -0.6711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495    0.2217    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12  7  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 12 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 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 12 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219672

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C(=O)C1=O)[C@]13CO[C@H]2C[C@H]1C(C)(C)C[C@H](O)C3

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-10(2)12-5-13-14-6-15-19(3,4)7-11(21)8-20(15,9-24-14)16(13)18(23)17(12)22/h5,10-11,14-15,21H,6-9H2,1-4H3/t11-,14-,15-,20+/m0/s1

> <INCHI_KEY>
FYYHBXSBPSRDEA-MRQYSOIQSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.52877092602128

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,10S,13S)-13-hydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),5-diene-3,4-dione

> <JCHEM_LOGP>
2.669919463666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.209915645084902

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7069828968398637

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
92.17

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,10S,13S)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),5-diene-3,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      12.323  -0.562   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.861   0.907   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.902   2.042   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.358   1.241   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.895   2.710   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.392   3.044   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.351   1.909   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.813   0.440   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.773  -0.695   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.317   0.106   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.779  -1.363   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.551   1.600   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.802   0.914   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.553   2.626   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.213   4.068   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.628   4.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.534   2.891   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.909   2.893   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.174   4.410   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.460   3.414   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.133   1.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.827   0.124   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.137  -1.253   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.386   0.414   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13   17   24                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   12                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

(1R,8S,10S,13S)-13-hydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),5-diene-3,4-dione

Traditional Name

(1R,8S,10S,13S)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),5-diene-3,4-dione

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=C(C(=O)C1=O)[C@]13CO[C@H]2C[C@H]1C(C)(C)C[C@H](O)C3

InChI Identifier

InChI=1S/C20H26O4/c1-10(2)12-5-13-14-6-15-19(3,4)7-11(21)8-20(15,9-24-14)16(13)18(23)17(12)22/h5,10-11,14-15,21H,6-9H2,1-4H3/t11-,14-,15-,20+/m0/s1

InChI Key

FYYHBXSBPSRDEA-MRQYSOIQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Teucrium viscidum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Oxane
Pyran
Cyclic alcohol
Ketone
Cyclic ketone
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxygen 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
logP	2.67	ChemAxon
pKa (Strongest Acidic)	15.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.17 m³·mol⁻¹	ChemAxon
Polarizability	36.53 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

58838851

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122178791

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,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione (NP0219672)

MOL for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

3D MOL for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

3D SDF for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

3D-SDF for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

PDB for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

3D PDB for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

SMILES for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

INCHI for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

Structure for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)

3D Structure for NP0219672 ((1r,8s,10s,13s)-13-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),5-diene-3,4-dione)