NP-MRD: Showing NP-Card for (1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione (NP0157075)

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Record Information

Version

2.0

Created at

2022-09-02 14:22:47 UTC

Updated at

2022-09-02 14:22:47 UTC

NP-MRD ID

NP0157075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione

Description

3-Oxo-16alpha-hydroxy-D:A-friedoolean-27-oic acid 27,16-lactone belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione is found in Mallotus repandus. Based on a literature review very few articles have been published on 3-Oxo-16alpha-hydroxy-D:A-friedoolean-27-oic acid 27,16-lactone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022216222D          

 33 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022216222D          

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  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 33 32  1  6  0  0  0
 25 33  1  0  0  0  0
 12 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]23[C@@H]4CC(C)(C)CC[C@]4(C)[C@@H](C[C@]12C)OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-18-19(31)8-9-20-26(18,4)11-10-21-27(20,5)14-15-30-22-16-25(2,3)12-13-28(22,6)23(33-24(30)32)17-29(21,30)7/h18,20-23H,8-17H2,1-7H3/t18-,20+,21-,22+,23+,26+,27-,28-,29+,30-/m0/s1

> <INCHI_KEY>
IUBMQGHIJKYGTC-YSNNSWNFSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.695

> <EXACT_MASS>
454.344695341

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
53.88926177756362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,5S,9R,10S,13S,14R,16R,17S,22R)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0^{1,14}.0^{4,13}.0^{5,10}.0^{17,22}]tetracosane-8,23-dione

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
6.741633495999998

> <ALOGPS_LOGS>
-6.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.949085788453276

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
129.9496

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5S,9R,10S,13S,14R,16R,17S,22R)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0^{1,14}.0^{4,13}.0^{5,10}.0^{17,22}]tetracosane-8,23-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      16.988   5.856   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.835   4.701   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.755   3.465   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      18.359   3.567   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      16.145   2.051   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.615   1.873   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.695   3.108   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.166   2.929   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.867   1.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.431   1.526   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.883   1.538   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.773   2.703   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.737   3.668   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.080   3.401   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.030   4.988   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.194   6.017   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.932   5.787   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.626   4.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.432   4.096   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.246   4.165   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.856   5.579   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.386   5.757   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.305   4.522   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.920   6.072   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.387   4.478   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.486   4.452   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.867   4.727   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.892   3.535   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.436   2.095   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.294   0.448   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.847   1.633   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.956   1.846   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.931   3.038   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9   10   20                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18   33                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    8   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    7    2   24                                             
CONECT   24   23                                                            
CONECT   25   16   26   27   33                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   33                                                       
CONECT   33   32   25   12                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-oxo-16a-Hydroxy-d:a-friedoolean-27-Oate 27,16-lactone	Generator
3-oxo-16a-Hydroxy-d:a-friedoolean-27-Oic acid 27,16-lactone	Generator
3-oxo-16alpha-Hydroxy-d:a-friedoolean-27-Oate 27,16-lactone	Generator
3-oxo-16Α-hydroxy-d:a-friedoolean-27-Oate 27,16-lactone	Generator
3-oxo-16Α-hydroxy-d:a-friedoolean-27-Oic acid 27,16-lactone	Generator

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6950 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

(1R,4S,5S,9R,10S,13S,14R,16R,17S,22R)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0^{1,14}.0^{4,13}.0^{5,10}.0^{17,22}]tetracosane-8,23-dione

Traditional Name

(1R,4S,5S,9R,10S,13S,14R,16R,17S,22R)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0^{1,14}.0^{4,13}.0^{5,10}.0^{17,22}]tetracosane-8,23-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]23[C@@H]4CC(C)(C)CC[C@]4(C)[C@@H](C[C@]12C)OC3=O

InChI Identifier

InChI=1S/C30H46O3/c1-18-19(31)8-9-20-26(18,4)11-10-21-27(20,5)14-15-30-22-16-25(2,3)12-13-28(22,6)23(33-24(30)32)17-29(21,30)7/h18,20-23H,8-17H2,1-7H3/t18-,20+,21-,22+,23+,26+,27-,28-,29+,30-/m0/s1

InChI Key

IUBMQGHIJKYGTC-YSNNSWNFSA-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
Mallotus repandus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Oxane
Pyran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	5.33	ALOGPS
logP	6.74	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	129.95 m³·mol⁻¹	ChemAxon
Polarizability	53.89 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

9103787

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10928543

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione (NP0157075)

MOL for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

3D MOL for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

3D SDF for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

3D-SDF for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

PDB for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

3D PDB for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

SMILES for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

INCHI for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

Structure for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)

3D Structure for NP0157075 ((1r,4s,5s,9r,10s,13s,14r,16r,17s,22r)-4,9,10,14,17,20,20-heptamethyl-24-oxahexacyclo[14.6.2.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁷,²²]tetracosane-8,23-dione)