NP-MRD: Showing NP-Card for (1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol (NP0222694)

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Record Information

Version

2.0

Created at

2022-09-06 00:35:42 UTC

Updated at

2022-09-06 00:35:42 UTC

NP-MRD ID

NP0222694

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol

Description

Przewalskin belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol is found in Salvia miltiorrhiza. (1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol was first documented in 2015 (PMID: 25611748). Based on a literature review a small amount of articles have been published on Przewalskin (PMID: 29191008) (PMID: 29939034) (PMID: 27754686).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202352D          

 20 23  0  0  1  0            999 V2000
    6.3541    0.4861    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
    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  1  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
    1.5143    0.0666    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
    1.5584    1.5497    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
    1.7006    2.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.5486    0.0000 C   0  0  2  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
    3.8639    2.1793    0.0000 C   0  0  2  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
    3.6440    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  5  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222694

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=C(C=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O2/c1-11-7-12-13(8-14(11)19)18-6-4-5-17(2,3)16(18)9-15(12)20-10-18/h7-8,15-16,19H,4-6,9-10H2,1-3H3/t15-,16-,18-/m0/s1

> <INCHI_KEY>
RHXIVZRYHFCBDN-BQFCYCMXSA-N

> <FORMULA>
C18H24O2

> <MOLECULAR_WEIGHT>
272.388

> <EXACT_MASS>
272.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.628514680082493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,10S)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-4-ol

> <JCHEM_LOGP>
4.172040394666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.800468393710345

> <JCHEM_PKA_STRONGEST_BASIC>
-4.182544198472142

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
80.3382

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,10S)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      11.861   0.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.358   1.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.895   2.710   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.392   3.044   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.351   1.909   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.813   0.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.317   0.106   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.779  -1.363   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.551   1.600   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.386   0.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.827   0.124   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.133   1.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.909   2.893   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.460   3.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.174   4.410   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.534   2.891   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.628   4.107   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.213   4.068   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.553   2.626   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.802   0.914   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   16   20                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    4   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    9                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₄O₂

Average Mass

272.3880 Da

Monoisotopic Mass

272.17763 Da

IUPAC Name

(1R,8S,10S)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-4-ol

Traditional Name

(1R,8S,10S)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-4-ol

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3

InChI Identifier

InChI=1S/C18H24O2/c1-11-7-12-13(8-14(11)19)18-6-4-5-17(2,3)16(18)9-15(12)20-10-18/h7-8,15-16,19H,4-6,9-10H2,1-3H3/t15-,16-,18-/m0/s1

InChI Key

RHXIVZRYHFCBDN-BQFCYCMXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia miltiorrhiza	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Benzopyran
Isochromane
2-benzopyran
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	4.17	ChemAxon
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.34 m³·mol⁻¹	ChemAxon
Polarizability	31.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00031093

Chemspider ID

21179044

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14139389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang ZY, Yu YJ, Huang CG, Huang XZ, Hu QF, Yang GY, Wang HB, Zhang XY, Li GP: Icetexane diterpenoids from Perovskia atriplicifolia. Planta Med. 2015 Feb;81(3):241-6. doi: 10.1055/s-0034-1396151. Epub 2015 Jan 22. [PubMed:25611748 ]
Li Z, Zhang X, Yang Z, Zhang Y, Xie Z: Biomimetic Synthesis of Isorosmanol and Przewalskin A. J Org Chem. 2018 Jan 5;83(1):437-442. doi: 10.1021/acs.joc.7b02369. Epub 2017 Dec 14. [PubMed:29191008 ]
Fischer M, Harms K, Koert U: Correction to Total Syntheses of 7,20-Oxa-Bridged Dinorditerpenes: Antihepatitis C Virus Active (+)-Elevenol from Flueggea virosa and (+)-Przewalskin. Org Lett. 2018 Jul 6;20(13):4158. doi: 10.1021/acs.orglett.8b01853. Epub 2018 Jun 25. [PubMed:29939034 ]
Fischer M, Harms K, Koert U: Total Syntheses of 7,20-Oxa-Bridged Dinorditerpenes: Antihepatitis C Virus Active (+)-Elevenol from Flueggea virosa and (+)-Przewalskin. Org Lett. 2016 Nov 4;18(21):5692-5695. doi: 10.1021/acs.orglett.6b02922. Epub 2016 Oct 18. [PubMed:27754686 ]
LOTUS database [Link]

Showing NP-Card for (1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol (NP0222694)

MOL for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

3D MOL for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

3D SDF for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

3D-SDF for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

PDB for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

3D PDB for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

SMILES for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

INCHI for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

Structure for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)

3D Structure for NP0222694 ((1r,8s,10s)-5,11,11-trimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-4-ol)