NP-MRD: Showing NP-Card for (1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one (NP0268748)

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Record Information

Version

2.0

Created at

2022-09-08 13:58:33 UTC

Updated at

2022-09-08 13:58:33 UTC

NP-MRD ID

NP0268748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one

Description

Pachanol D belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one is found in Stenocereus dumortieri. (1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one was first documented in 2012 (PMID: 22704889). Based on a literature review very few articles have been published on Pachanol D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215582D          

 33 38  0  0  1  0            999 V2000
   -0.8025   -0.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3514    0.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2298    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250    1.9569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029    1.2780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 32 14  1  6  0  0  0
  7 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END

     RDKit          2D

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M  END


  Mrv1652309082215582D          

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 12 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  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  1  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  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  1  0  0  0
 32 14  1  6  0  0  0
  7 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268748

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O4/c1-24(2)15-18-17-7-8-20-26(5)11-10-21(30)25(3,4)19(26)9-12-27(20,6)29(17)14-13-28(18,22(31)16-24)23(32)33-29/h7,18-22,30-31H,8-16H2,1-6H3/t18-,19-,20+,21-,22?,26-,27+,28-,29-/m0/s1

> <INCHI_KEY>
RWAXCCHQQDWVCF-JVGBDFKTSA-N

> <FORMULA>
C29H44O4

> <MOLECULAR_WEIGHT>
456.667

> <EXACT_MASS>
456.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
37.316728528511774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,7S,10S,11R,15S,20S)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0^{1,14}.0^{2,11}.0^{5,10}.0^{15,20}]tetracos-13-en-21-one

> <JCHEM_LOGP>
4.725054066000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.4894332874812

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.419280815888083

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351216821234092

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
128.5468

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,7S,10S,11R,15S,20S)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0^{1,14}.0^{2,11}.0^{5,10}.0^{15,20}]tetracos-13-en-21-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.498  -0.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.009  -0.318   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.132  -1.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.656   1.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.429   2.263   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.233   3.653   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.059   2.386   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.093   3.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.348   2.636   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.860   2.179   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.864   3.794   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.279   3.738   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.628   5.134   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.192   0.673   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.032  -0.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.601  -0.644   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.320   0.751   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.856   0.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.182  -0.525   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.718  -0.416   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.254  -0.307   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.928   1.078   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.464   1.187   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.065   2.353   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.472   2.981   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.691   3.847   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.529   2.244   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.667   3.520   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.131   3.411   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.457   2.026   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.703   3.369   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.567   0.803   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.564  -0.436   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   33                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12   32                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14   30                                             
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   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   10   31                                             
CONECT   31   30                                                            
CONECT   32   14    7   33                                                  
CONECT   33   32    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₄O₄

Average Mass

456.6670 Da

Monoisotopic Mass

456.32396 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H44O4/c1-24(2)15-18-17-7-8-20-26(5)11-10-21(30)25(3,4)19(26)9-12-27(20,6)29(17)14-13-28(18,22(31)16-24)23(32)33-29/h7,18-22,30-31H,8-16H2,1-6H3/t18-,19-,20+,21-,22?,26-,27+,28-,29-/m0/s1

InChI Key

RWAXCCHQQDWVCF-JVGBDFKTSA-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
Stenocereus dumortieri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101785448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kakuta K, Baba M, Ito S, Kinoshita K, Koyama K, Takahashi K: New triterpenoid saponins from cacti and anti-type I allergy activity of saponins from cactus. Bioorg Med Chem Lett. 2012 Jul 15;22(14):4793-800. doi: 10.1016/j.bmcl.2012.05.058. Epub 2012 Jun 1. [PubMed:22704889 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one (NP0268748)

MOL for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

3D MOL for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

3D SDF for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

3D-SDF for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

PDB for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

3D PDB for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

SMILES for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

INCHI for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

Structure for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)

3D Structure for NP0268748 ((1r,2r,5r,7s,10s,11r,15s,20s)-7,19-dihydroxy-2,6,6,10,17,17-hexamethyl-22-oxahexacyclo[18.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tetracos-13-en-21-one)