NP-MRD: Showing NP-Card for (1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione (NP0213873)

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Record Information

Version

2.0

Created at

2022-09-05 12:59:19 UTC

Updated at

2022-09-05 12:59:19 UTC

NP-MRD ID

NP0213873

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione

Description

CHEMBL501175 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione is found in Styrax tonkinensis. Based on a literature review very few articles have been published on CHEMBL501175.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052214592D          

 35 41  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309052214592D          

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    5.9720    1.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7335    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201    0.3169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4079    1.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085   -0.0150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4774   -0.8394    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  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  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  6 13  1  1  0  0  0
 13 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 28 25  1  1  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 18 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  1  0  0  0
 11 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  1  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213873

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]23CC[C@]4(C)[C@](OC2=O)([C@H]2O[C@H]2[C@@H]2[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5[C@H](O)C[C@@]42C)[C@@H]3C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-24(2)10-12-29-13-11-28(7)27(6)14-16(31)20-25(3,4)18(32)8-9-26(20,5)21(27)19-22(34-19)30(28,17(29)15-24)35-23(29)33/h16-17,19-22,31H,8-15H2,1-7H3/t16-,17-,19+,20+,21-,22+,26+,27-,28+,29+,30-/m1/s1

> <INCHI_KEY>
BJHPXVYFOSPVSF-PQYJJHRASA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.677

> <EXACT_MASS>
484.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.94220396173859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5R,6S,11R,12R,14R,15S,18S,23R)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,11}.0^{18,23}]pentacosane-9,25-dione

> <JCHEM_LOGP>
4.928151001333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.43652233507634

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.88109569114177

> <JCHEM_PKA_STRONGEST_BASIC>
-2.85080239158869

> <JCHEM_POLAR_SURFACE_AREA>
76.13

> <JCHEM_REFRACTIVITY>
130.6395

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,6S,11R,12R,14R,15S,18S,23R)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,11}.0^{18,23}]pentacosane-9,25-dione

> <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       2.229  -3.428   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.263  -2.286   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.208  -3.502   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.959  -1.466   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.017   0.072   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.379   0.792   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.260   2.149   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.856   2.082   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.503   0.596   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.349   1.883   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.610  -0.788   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.040  -1.849   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.883  -0.747   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.419  -1.225   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.513  -2.099   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.290  -3.428   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.053  -2.091   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.832  -0.743   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.372  -0.745   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.601  -2.078   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.141  -2.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.681  -2.082   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.452  -0.749   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.992  -0.751   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.684   0.585   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.132   1.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.419   2.102   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.144   0.588   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.376   1.922   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.148   3.255   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.836   1.924   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.064   0.592   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.228   2.123   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.683  -0.028   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.625  -1.567   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   35                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13   34                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   32                                             
CONECT   10    9                                                            
CONECT   11    9   12   15   34                                             
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13                                                            
CONECT   15   11   16   17                                                  
CONECT   16   15   17                                                       
CONECT   17   16   15   18                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   19   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   18    9   33                                             
CONECT   33   32                                                            
CONECT   34   11    6   35                                                  
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₅

Average Mass

484.6770 Da

Monoisotopic Mass

484.31887 Da

IUPAC Name

(1S,2S,4S,5R,6S,11R,12R,14R,15S,18S,23R)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,11}.0^{18,23}]pentacosane-9,25-dione

Traditional Name

(1S,2S,4S,5R,6S,11R,12R,14R,15S,18S,23R)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,11}.0^{18,23}]pentacosane-9,25-dione

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]23CC[C@]4(C)[C@](OC2=O)([C@H]2O[C@H]2[C@@H]2[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5[C@H](O)C[C@@]42C)[C@@H]3C1

InChI Identifier

InChI=1S/C30H44O5/c1-24(2)10-12-29-13-11-28(7)27(6)14-16(31)20-25(3,4)18(32)8-9-26(20,5)21(27)19-22(34-19)30(28,17(29)15-24)35-23(29)33/h16-17,19-22,31H,8-15H2,1-7H3/t16-,17-,19+,20+,21-,22+,26+,27-,28+,29+,30-/m1/s1

InChI Key

BJHPXVYFOSPVSF-PQYJJHRASA-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
Styrax tonkinensis	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
Caprolactone
Oxepane
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Cyclic ketone
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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
logP	4.93	ChemAxon
pKa (Strongest Acidic)	14.88	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	130.64 m³·mol⁻¹	ChemAxon
Polarizability	54.94 Å³	ChemAxon
Number of Rings	7	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

9765942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11591179

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione (NP0213873)

MOL for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

3D MOL for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

3D SDF for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

3D-SDF for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

PDB for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

3D PDB for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

SMILES for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

INCHI for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

Structure for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)

3D Structure for NP0213873 ((1s,2s,4s,5r,6s,11r,12r,14r,15s,18s,23r)-12-hydroxy-6,10,10,14,15,21,21-heptamethyl-3,24-dioxaheptacyclo[16.5.2.0¹,¹⁵.0²,⁴.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]pentacosane-9,25-dione)