NP-MRD: Showing NP-Card for (1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione (NP0196092)

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Record Information

Version

2.0

Created at

2022-09-04 14:05:58 UTC

Updated at

2022-09-04 14:05:58 UTC

NP-MRD ID

NP0196092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione

Description

CHEMBL500648 belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. (1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione is found in Jaborosa rotacea. Based on a literature review very few articles have been published on CHEMBL500648.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216052D          

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M  END

     RDKit          3D

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  Mrv1652309042216052D          

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 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  2  0  0  0  0
 30 34  1  0  0  0  0
 14 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0196092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)[C@@H]2C(C)=C(C)C(=O)O[C@@]22C[C@H]3[C@@H](C[C@@H](O)[C@@]4(O)CC=CC(=O)[C@]34C)[C@@H]3CC[C@]1(O)[C@@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O7/c1-13-14(2)23(32)35-28-12-18-16(11-20(30)27(34)9-6-7-19(29)24(18,27)4)17-8-10-26(33,25(17,28)5)15(3)22(31)21(13)28/h6-7,15-18,20-21,30,33-34H,8-12H2,1-5H3/t15-,16+,17+,18+,20-,21+,24+,25+,26-,27+,28+/m1/s1

> <INCHI_KEY>
YMNXFTUYIKXAPW-UGAJVUOVSA-N

> <FORMULA>
C28H36O7

> <MOLECULAR_WEIGHT>
484.589

> <EXACT_MASS>
484.246103499

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.25558965325249

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4R,9R,10R,12S,13S,16R,17S,19R,24S)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0^{1,19}.0^{3,12}.0^{4,9}.0^{16,24}]tetracosa-6,20-diene-5,18,22-trione

> <JCHEM_LOGP>
2.4759096313333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.085870316916584

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.200900228111871

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2581324894836436

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000002

> <JCHEM_REFRACTIVITY>
127.66449999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4R,9R,10R,12S,13S,16R,17S,19R,24S)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0^{1,19}.0^{3,12}.0^{4,9}.0^{16,24}]tetracosa-6,20-diene-5,18,22-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.410  -3.905   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.873  -2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.330  -2.178   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.318  -3.339   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.683  -1.558   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.691   1.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.644   2.673   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.639   3.753   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.034   4.407   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.870   3.971   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.383   3.680   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.391   4.844   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.895   3.389   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.375  -1.558   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.870  -0.103   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.263  -0.008   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.557   0.537   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.897  -1.186   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.891  -2.363   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   34                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   34                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   15   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    5   31   34                                             
CONECT   31   30   32                                                       
CONECT   32   31    2   33                                                  
CONECT   33   32                                                            
CONECT   34   30   14   10   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₇

Average Mass

484.5890 Da

Monoisotopic Mass

484.24610 Da

IUPAC Name

(1S,3S,4R,9R,10R,12S,13S,16R,17S,19R,24S)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0^{1,19}.0^{3,12}.0^{4,9}.0^{16,24}]tetracosa-6,20-diene-5,18,22-trione

Traditional Name

(1S,3S,4R,9R,10R,12S,13S,16R,17S,19R,24S)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0^{1,19}.0^{3,12}.0^{4,9}.0^{16,24}]tetracosa-6,20-diene-5,18,22-trione

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)[C@@H]2C(C)=C(C)C(=O)O[C@@]22C[C@H]3[C@@H](C[C@@H](O)[C@@]4(O)CC=CC(=O)[C@]34C)[C@@H]3CC[C@]1(O)[C@@]23C

InChI Identifier

InChI=1S/C28H36O7/c1-13-14(2)23(32)35-28-12-18-16(11-20(30)27(34)9-6-7-19(29)24(18,27)4)17-8-10-26(33,25(17,28)5)15(3)22(31)21(13)28/h6-7,15-18,20-21,30,33-34H,8-12H2,1-5H3/t15-,16+,17+,18+,20-,21+,24+,25+,26-,27+,28+/m1/s1

InChI Key

YMNXFTUYIKXAPW-UGAJVUOVSA-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
Jaborosa rotacea	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
6-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
1-oxosteroid
Oxosteroid
17-hydroxysteroid
Cyclohexenone
Dihydropyranone
Pyran
Enoate ester
Cyclic alcohol
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Ketone
Lactone
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
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	2.48	ChemAxon
pKa (Strongest Acidic)	11.2	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	127.66 m³·mol⁻¹	ChemAxon
Polarizability	51.26 Å³	ChemAxon
Number of Rings	6	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

24710924

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44583789

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione (NP0196092)

MOL for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

3D MOL for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

3D SDF for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

3D-SDF for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

PDB for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

3D PDB for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

SMILES for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

INCHI for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

Structure for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)

3D Structure for NP0196092 ((1s,3s,4r,9r,10r,12s,13s,16r,17s,19r,24s)-9,10,16-trihydroxy-4,17,20,21,24-pentamethyl-23-oxahexacyclo[11.10.1.0¹,¹⁹.0³,¹².0⁴,⁹.0¹⁶,²⁴]tetracosa-6,20-diene-5,18,22-trione)