NP-MRD: Showing NP-Card for 1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one (NP0156921)

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Record Information

Version

2.0

Created at

2022-09-02 14:12:08 UTC

Updated at

2022-09-02 14:12:08 UTC

NP-MRD ID

NP0156921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one

Description

NSC144946 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one is found in Clerodendrum cyrtophyllum and Clerodendrum splendens. Based on a literature review very few articles have been published on NSC144946.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022216122D          

 32 36  0  0  0  0            999 V2000
   -0.2823   -2.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5426   -3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9659   -2.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6189   -3.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855   -4.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592   -4.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -5.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -5.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -5.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133   -5.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149   -5.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117   -4.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -3.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334   -2.9315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9615   -4.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864   -4.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -3.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2097   -3.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0346   -3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4362   -4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2611   -4.4355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0129   -5.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573   -5.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1880   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7647   -5.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -5.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382   -5.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6119   -5.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868   -4.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4  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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 18 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
 17 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  0  0  0  0
 13 32  1  0  0  0  0
  8 32  1  0  0  0  0
  4 32  1  0  0  0  0
M  END


  Mrv1652309022216122D          

 32 36  0  0  0  0            999 V2000
   -0.2823   -2.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5426   -3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9659   -2.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6189   -3.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855   -4.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592   -4.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -5.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -5.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -5.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133   -5.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149   -5.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117   -4.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -3.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334   -2.9315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9615   -4.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864   -4.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -3.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2097   -3.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0346   -3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4362   -4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2611   -4.4355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0129   -5.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573   -5.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1880   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7647   -5.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -5.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382   -5.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6119   -5.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868   -4.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4  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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 18 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
 17 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  0  0  0  0
 13 32  1  0  0  0  0
  8 32  1  0  0  0  0
  4 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1(O)CCC2CCC3(C)C(C12)C(=O)CC1C2(C)CCC(O)C(C)(C)C2CCC31C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O3/c1-17(2)29(32)15-9-18-8-13-28(7)24(23(18)29)19(30)16-21-26(5)12-11-22(31)25(3,4)20(26)10-14-27(21,28)6/h18,20-24,31-32H,1,8-16H2,2-7H3

> <INCHI_KEY>
RHSSXHIZNDJURV-UHFFFAOYSA-N

> <FORMULA>
C29H46O3

> <MOLECULAR_WEIGHT>
442.684

> <EXACT_MASS>
442.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
52.49807775709809

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8,17-dihydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-11-one

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
5.1434027826666675

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.32038999440067

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.997100370838957

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351217705594384

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
128.55159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,17-dihydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-11-one

> <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      -0.527  -5.587   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.013  -5.611   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.803  -4.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.762  -6.956   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.022  -6.070   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.346  -7.561   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.484  -9.094   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.985  -9.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.735 -10.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.275 -10.806   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.065  -9.484   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.814 -10.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.315  -8.139   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.105  -6.817   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.356  -5.472   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.645  -6.841   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.395  -8.186   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.935  -8.209   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.185  -6.864   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.725  -6.888   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.265  -6.911   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.014  -8.256   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.554  -8.280   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.224  -9.578   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.663 -10.127   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.934 -11.090   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.684  -9.555   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.894 -10.876   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.354 -10.853   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.605  -9.508   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.742 -11.042   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.775  -8.116   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   32                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   30                                             
CONECT   12   11                                                            
CONECT   13   11   14   32                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   17   11   31                                             
CONECT   31   30                                                            
CONECT   32   13    8    4                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆O₃

Average Mass

442.6840 Da

Monoisotopic Mass

442.34470 Da

IUPAC Name

8,17-dihydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-11-one

Traditional Name

8,17-dihydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-11-one

CAS Registry Number

Not Available

SMILES

CC(=C)C1(O)CCC2CCC3(C)C(C12)C(=O)CC1C2(C)CCC(O)C(C)(C)C2CCC31C

InChI Identifier

InChI=1S/C29H46O3/c1-17(2)29(32)15-9-18-8-13-28(7)24(23(18)29)19(30)16-21-26(5)12-11-22(31)25(3,4)20(26)10-14-27(21,28)6/h18,20-24,31-32H,1,8-16H2,2-7H3

InChI Key

RHSSXHIZNDJURV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Clerodendrum cyrtophyllum	LOTUS Database	35616633
Clerodendrum splendens	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
7-oxosteroid
Oxosteroid
Hydroxysteroid
15-hydroxysteroid
Steroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.63	ALOGPS
logP	5.14	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	128.55 m³·mol⁻¹	ChemAxon
Polarizability	52.5 Å³	ChemAxon
Number of Rings	5	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

252581

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

286500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one (NP0156921)

MOL for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

3D MOL for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

3D SDF for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

3D-SDF for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

PDB for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

3D PDB for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

SMILES for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

INCHI for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

Structure for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)

3D Structure for NP0156921 (1,9-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-tetradecahydro-2h-cyclopenta[a]chrysen-13-one)