NP-MRD: Showing NP-Card for (4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate (NP0251632)

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Record Information

Version

2.0

Created at

2022-09-07 14:53:01 UTC

Updated at

2022-09-07 14:53:01 UTC

NP-MRD ID

NP0251632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

16-Epi-Scalarolbutenolide belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. (4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate is found in Hyrtios erectus and Spongia agaricina. (4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate was first documented in 2005 (PMID: 16378375). Based on a literature review very few articles have been published on 16-Epi-Scalarolbutenolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216532D          

 32 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072216532D          

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 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
  5 32  1  0  0  0  0
 27 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3C[C@@H](O)[C@]2(C)[C@H]2OC(=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O5/c1-15(28)31-17-13-20-26(5)11-8-18-24(2,3)9-7-10-25(18,4)19(26)14-21(29)27(20,6)23-16(17)12-22(30)32-23/h12,17-21,23,29H,7-11,13-14H2,1-6H3/t17-,18-,19+,20-,21+,23-,25-,26+,27+/m0/s1

> <INCHI_KEY>
NUXDYAGOJZSDBF-ZWRXBZFVSA-N

> <FORMULA>
C27H40O5

> <MOLECULAR_WEIGHT>
444.612

> <EXACT_MASS>
444.287574388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.85058748077189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
4.320884215

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.894789526530818

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.01962529429782

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9736051419910536

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
121.23949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,9S,10R,11R,13R,14S,19S)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxo-8-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5-en-4-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       7.206   1.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.996  -0.002   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.246  -1.347   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.536   0.022   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.326  -1.300   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.866  -1.277   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.656  -2.598   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.196  -2.575   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.406  -1.253   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.946  -1.230   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.485  -1.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.276  -2.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.815  -2.505   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.525  -0.992   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.254  -1.956   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.606  -3.827   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.856  -5.172   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.316  -5.195   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.526  -3.873   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.776  -5.219   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.986  -3.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.236  -5.242   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.697  -5.265   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.947  -6.611   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.906  -3.944   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.157  -5.289   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.367  -3.967   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.354  -5.127   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.937  -4.522   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.616  -5.312   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.075  -2.988   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.576  -2.645   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9   10   21                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    8   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    7   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    5   27                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₅

Average Mass

444.6120 Da

Monoisotopic Mass

444.28757 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3C[C@@H](O)[C@]2(C)[C@H]2OC(=O)C=C12

InChI Identifier

InChI=1S/C27H40O5/c1-15(28)31-17-13-20-26(5)11-8-18-24(2,3)9-7-10-25(18,4)19(26)14-21(29)27(20,6)23-16(17)12-22(30)32-23/h12,17-21,23,29H,7-11,13-14H2,1-6H3/t17-,18-,19+,20-,21+,23-,25-,26+,27+/m0/s1

InChI Key

NUXDYAGOJZSDBF-ZWRXBZFVSA-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
Hyrtios erectus	LOTUS Database	35616633
Spongia agaricina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00049771

Chemspider ID

10229333

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21600071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Youssef DT, Shaala LA, Emara S: Antimycobacterial scalarane-based sesterterpenes from the Red Sea sponge Hyrtios erecta. J Nat Prod. 2005 Dec;68(12):1782-4. doi: 10.1021/np0502645. [PubMed:16378375 ]
LOTUS database [Link]

Showing NP-Card for (4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate (NP0251632)

MOL for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

3D MOL for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

3D SDF for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

3D-SDF for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

PDB for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

3D PDB for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

SMILES for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

INCHI for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

Structure for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)

3D Structure for NP0251632 ((4s,5as,5br,7as,11as,11br,13r,13ar,13bs)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-b]furan-4-yl acetate)