NP-MRD: Showing NP-Card for (3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate (NP0234585)

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Record Information

Version

2.0

Created at

2022-09-06 16:41:56 UTC

Updated at

2022-09-06 16:41:57 UTC

NP-MRD ID

NP0234585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate

Description

CHEMBL480698 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate is found in Stemodia foliosa. Based on a literature review very few articles have been published on CHEMBL480698.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062218412D          

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M  END

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  Mrv1652309062218412D          

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M  END
> <DATABASE_ID>
NP0234585

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC(=O)CC(=O)O[C@H]1C[C@@]2(C)O[C@](C)(CC[C@@H]2[C@@]2(C)CCCC(C)(C)[C@H]12)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O5/c1-8-10-16-30-21(28)17-22(29)31-19-18-27(7)20(12-15-25(5,9-2)32-27)26(6)14-11-13-24(3,4)23(19)26/h9,19-20,23H,2,8,10-18H2,1,3-7H3/t19-,20+,23-,25-,26+,27+/m0/s1

> <INCHI_KEY>
FLQJTWRILTVLCE-ZSTIODBZSA-N

> <FORMULA>
C27H44O5

> <MOLECULAR_WEIGHT>
448.644

> <EXACT_MASS>
448.318874517

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.67230347716285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate

> <JCHEM_LOGP>
5.9201498853333305

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.142597669364722

> <JCHEM_PKA_STRONGEST_BASIC>
-4.235030011023678

> <JCHEM_POLAR_SURFACE_AREA>
61.83000000000001

> <JCHEM_REFRACTIVITY>
125.15999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.870  -8.017   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.344  -6.570   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324  -6.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.194   2.987   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.184   1.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   32                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13    8   17                                                  
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   17   30                                                       
CONECT   30   29    7   31   32                                             
CONECT   31   30                                                            
CONECT   32   30    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₅

Average Mass

448.6440 Da

Monoisotopic Mass

448.31887 Da

IUPAC Name

(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate

Traditional Name

(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)CC(=O)O[C@H]1C[C@@]2(C)O[C@](C)(CC[C@@H]2[C@@]2(C)CCCC(C)(C)[C@H]12)C=C

InChI Identifier

InChI=1S/C27H44O5/c1-8-10-16-30-21(28)17-22(29)31-19-18-27(7)20(12-15-25(5,9-2)32-27)26(6)14-11-13-24(3,4)23(19)26/h9,19-20,23H,2,8,10-18H2,1,3-7H3/t19-,20+,23-,25-,26+,27+/m0/s1

InChI Key

FLQJTWRILTVLCE-ZSTIODBZSA-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
Stemodia foliosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Naphthopyran
Naphthalene
Dicarboxylic acid or derivatives
Oxane
1,3-dicarbonyl compound
Pyran
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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
logP	5.92	ChemAxon
pKa (Strongest Acidic)	12.14	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.16 m³·mol⁻¹	ChemAxon
Polarizability	52.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

23341192

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24970706

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate (NP0234585)

MOL for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

3D MOL for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

3D SDF for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

3D-SDF for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

PDB for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

3D PDB for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

SMILES for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

INCHI for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

Structure for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)

3D Structure for NP0234585 ((3r,4ar,6s,6as,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-6-yl 1-butyl propanedioate)