NP-MRD: Showing NP-Card for (3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate (NP0238314)

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Record Information

Version

2.0

Created at

2022-09-06 21:41:17 UTC

Updated at

2022-09-06 21:41:17 UTC

NP-MRD ID

NP0238314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Phyllolactone B 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. (3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate is found in Phyllospongia lamellosa. Based on a literature review very few articles have been published on Phyllolactone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062223412D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062223412D          

 35 39  0  0  1  0            999 V2000
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    3.1545   -3.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4779   -3.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7436   -2.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9245   -2.5241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5459   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982   -1.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0557   -0.5741    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
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 29 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0238314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@@H]1CC[C@@]2(C)C(CC[C@@]3(C)C4CCC5=C(C(=O)O[C@H]5C)[C@@]4(C)[C@@H](O)CC23)[C@@]1(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O5/c1-8-24(32)35-23-13-15-28(5)19(27(23,4)9-2)12-14-29(6)20-11-10-18-17(3)34-26(33)25(18)30(20,7)22(31)16-21(28)29/h17,19-23,31H,8-16H2,1-7H3/t17-,19?,20?,21?,22-,23+,27+,28-,29-,30+/m0/s1

> <INCHI_KEY>
KGWYOVQTMLIBDJ-VXGGKDEKSA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.693

> <EXACT_MASS>
486.334524581

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.40805342451868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6S,10S,11S,14R,17R,18R)-18-ethyl-11-hydroxy-1,6,10,14,18-pentamethyl-8-oxo-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-17-yl propanoate

> <JCHEM_LOGP>
5.627678026333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.636117930080761

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.350702550193471

> <JCHEM_PKA_STRONGEST_BASIC>
-2.970455431364738

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
135.0555

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S,10S,11S,14R,17R,18R)-18-ethyl-11-hydroxy-1,6,10,14,18-pentamethyl-8-oxo-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-17-yl propanoate

> <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       2.758   0.092   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.548  -1.230   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.799  -2.575   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.259  -2.598   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.589  -3.897   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.129  -3.873   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.878  -2.528   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.418  -2.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.208  -3.827   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.958  -2.481   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748  -3.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.498  -2.458   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.037  -2.435   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.787  -1.089   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.828  -3.756   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.577  -2.411   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.368  -3.733   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.158  -5.055   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.408  -6.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.868  -6.423   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.078  -5.102   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.538  -5.125   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.328  -6.447   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.789  -6.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.249  -6.494   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.459  -5.172   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.919  -5.195   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.888  -6.735   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.625  -6.031   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.255  -5.329   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.659  -4.712   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.819  -5.725   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.797  -3.178   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      15.380  -2.573   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.037  -1.072   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   26                                             
CONECT   10    9                                                            
CONECT   11    9   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   34                                                  
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   11   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    9   27                                                  
CONECT   27   26    6   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   18   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   17   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₅

Average Mass

486.6930 Da

Monoisotopic Mass

486.33452 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@@H]1CC[C@@]2(C)C(CC[C@@]3(C)C4CCC5=C(C(=O)O[C@H]5C)[C@@]4(C)[C@@H](O)CC23)[C@@]1(C)CC

InChI Identifier

InChI=1S/C30H46O5/c1-8-24(32)35-23-13-15-28(5)19(27(23,4)9-2)12-14-29(6)20-11-10-18-17(3)34-26(33)25(18)30(20,7)22(31)16-21(28)29/h17,19-23,31H,8-16H2,1-7H3/t17-,19?,20?,21?,22-,23+,27+,28-,29-,30+/m0/s1

InChI Key

KGWYOVQTMLIBDJ-VXGGKDEKSA-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
Phyllospongia lamellosa	LOTUS Database	35616633

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
Steroid lactone
2-hydroxysteroid
Hydroxysteroid
7-alpha-hydroxysteroid
7-hydroxysteroid
16-oxasteroid
Steroid
2-furanone
Dicarboxylic acid or derivatives
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Dihydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Alcohol
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

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

426520

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

486509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate (NP0238314)

MOL for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

3D MOL for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

3D SDF for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

3D-SDF for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

PDB for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

3D PDB for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

SMILES for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

INCHI for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

Structure for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)

3D Structure for NP0238314 ((3s,5br,8r,9r,11ar,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl propanoate)