NP-MRD: Showing NP-Card for (3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate (NP0202904)

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Record Information

Version

2.0

Created at

2022-09-04 22:13:38 UTC

Updated at

2022-09-04 22:13:38 UTC

NP-MRD ID

NP0202904

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate

Description

(1S,2S,4S,5R,7R,10R,11S,15R)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-13-en-5-yl acetate belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. (3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate is found in Anodendron affine. Based on a literature review very few articles have been published on (1S,2S,4S,5R,7R,10R,11S,15R)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-13-en-5-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200132D          

 32 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052200132D          

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M  END
> <DATABASE_ID>
NP0202904

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H]2CC[C@@H]3[C@H](C(=O)C[C@]4(C)C(=CC[C@]34O)C3=CC(=O)OC3)[C@@]2(C)C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O7/c1-13(26)32-20-9-15-4-5-17-22(23(15,2)10-18(20)27)19(28)11-24(3)16(6-7-25(17,24)30)14-8-21(29)31-12-14/h6,8,15,17-18,20,22,27,30H,4-5,7,9-12H2,1-3H3/t15-,17-,18+,20-,22-,23+,24-,25+/m1/s1

> <INCHI_KEY>
XURSEJHINUAAFD-IXYLZVJVSA-N

> <FORMULA>
C25H32O7

> <MOLECULAR_WEIGHT>
444.524

> <EXACT_MASS>
444.21480337

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.36839825475526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,5R,7R,10R,11S,15R)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-yl acetate

> <JCHEM_LOGP>
1.1047463656666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.769361351951659

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.360776100445607

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1674359308254454

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
115.67089999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,7R,10R,11S,15R)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.208  -1.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.692  -0.905   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.169   0.544   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.105   1.628   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.453   2.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.727   3.054   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.777   4.593   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.943   2.108   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.420   0.660   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.504  -3.399   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.653   0.815   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   26                                             
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   18                                                       
CONECT   24   17   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   10   15   27                                             
CONECT   27   26                                                            
CONECT   28   11    7   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30    5   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,4S,5R,7R,10R,11S,15R)-4,11-Dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadec-13-en-5-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₂O₇

Average Mass

444.5240 Da

Monoisotopic Mass

444.21480 Da

IUPAC Name

(1S,2S,4S,5R,7R,10R,11S,15R)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-yl acetate

Traditional Name

(1S,2S,4S,5R,7R,10R,11S,15R)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H]2CC[C@@H]3[C@H](C(=O)C[C@]4(C)C(=CC[C@]34O)C3=CC(=O)OC3)[C@@]2(C)C[C@@H]1O

InChI Identifier

InChI=1S/C25H32O7/c1-13(26)32-20-9-15-4-5-17-22(23(15,2)10-18(20)27)19(28)11-24(3)16(6-7-25(17,24)30)14-8-21(29)31-12-14/h6,8,15,17-18,20,22,27,30H,4-5,7,9-12H2,1-3H3/t15-,17-,18+,20-,22-,23+,24-,25+/m1/s1

InChI Key

XURSEJHINUAAFD-IXYLZVJVSA-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
Anodendron affine	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
Steroid ester
Androstane-skeleton
2-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
11-oxosteroid
Oxosteroid
2-furanone
Dicarboxylic acid or derivatives
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Ketone
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
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	1.1	ChemAxon
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.67 m³·mol⁻¹	ChemAxon
Polarizability	47.37 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10270272

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636041

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate (NP0202904)

MOL for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D MOL for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D SDF for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D-SDF for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

PDB for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D PDB for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

SMILES for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

INCHI for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

Structure for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D Structure for NP0202904 ((3as,3br,5ar,7r,8s,9as,9bs,11ar)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-3h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,11h-cyclopenta[a]phenanthren-7-yl acetate)