NP-MRD: Showing NP-Card for (3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate (NP0248860)

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Record Information

Version

2.0

Created at

2022-09-07 11:15:56 UTC

Updated at

2022-09-07 11:15:56 UTC

NP-MRD ID

NP0248860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate

Description

CHEBI:68045 Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. Based on a literature review very few articles have been published on CHEBI:68045.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213152D          

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 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  5 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0248860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3C[C@@H](OC(C)=O)[C@]2(C)C2=C1[C@H](O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O6/c1-15(29)33-20-14-18-26(4)11-8-10-25(2,3)17(26)9-12-27(18,5)19-13-16(32-7)21-22(28(19,20)6)24(31)34-23(21)30/h16-20,23,30H,8-14H2,1-7H3/t16-,17+,18-,19+,20-,23-,26+,27-,28-/m1/s1

> <INCHI_KEY>
PWNLVHXPDDFBAP-YJFPDCRJSA-N

> <FORMULA>
C28H42O6

> <MOLECULAR_WEIGHT>
474.638

> <EXACT_MASS>
474.298139072

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.73871272203897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4R,6R,10S,11R,13R,14S,19S)-6-hydroxy-4-methoxy-1,10,14,18,18-pentamethyl-8-oxo-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-11-yl acetate

> <JCHEM_LOGP>
4.344901051666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.683472122881653

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.295175458857747

> <JCHEM_PKA_STRONGEST_BASIC>
-4.152274022409824

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
127.18990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,6R,10S,11R,13R,14S,19S)-6-hydroxy-4-methoxy-1,10,14,18,18-pentamethyl-8-oxo-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-11-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      11.403   4.618   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.864   4.642   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.534   3.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.243  -0.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.033   0.653   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.324   1.632   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.484   2.645   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.462   0.098   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.703  -2.008   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.703  -0.645   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.452  -1.991   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.662  -3.313   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.412  -4.658   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.122  -3.289   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.623  -0.599   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.855   2.664   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.875   3.628   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.914   3.414   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.454   3.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.994   3.367   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    6   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23   24   30                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   22   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    5   21   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₆

Average Mass

474.6380 Da

Monoisotopic Mass

474.29814 Da

IUPAC Name

(1R,2S,4R,6R,10S,11R,13R,14S,19S)-6-hydroxy-4-methoxy-1,10,14,18,18-pentamethyl-8-oxo-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-11-yl acetate

Traditional Name

(1R,2S,4R,6R,10S,11R,13R,14S,19S)-6-hydroxy-4-methoxy-1,10,14,18,18-pentamethyl-8-oxo-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-11-yl acetate

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3C[C@@H](OC(C)=O)[C@]2(C)C2=C1[C@H](O)OC2=O

InChI Identifier

InChI=1S/C28H42O6/c1-15(29)33-20-14-18-26(4)11-8-10-25(2,3)17(26)9-12-27(18,5)19-13-16(32-7)21-22(28(19,20)6)24(31)34-23(21)30/h16-20,23,30H,8-14H2,1-7H3/t16-,17+,18-,19+,20-,23-,26+,27-,28-/m1/s1

InChI Key

PWNLVHXPDDFBAP-YJFPDCRJSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Hydroxysteroid
17-hydroxysteroid
16-oxasteroid
Steroid
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

scalarane sesterterpenoid (CHEBI:68045 )

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	4.34	ChemAxon
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	127.19 m³·mol⁻¹	ChemAxon
Polarizability	53.74 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

26348379

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54582289

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate (NP0248860)

MOL for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

3D MOL for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

3D SDF for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

3D-SDF for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

PDB for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

3D PDB for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

SMILES for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

INCHI for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

Structure for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)

3D Structure for NP0248860 ((3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate)