NP-MRD: Showing NP-Card for (4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol (NP0318635)

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Record Information

Version

2.0

Created at

2022-09-11 19:14:39 UTC

Updated at

2022-09-11 19:14:39 UTC

NP-MRD ID

NP0318635

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol

Description

Disidein belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. (4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol was first documented in 1988 (PMID: 2907790). Based on a literature review very few articles have been published on Disidein.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221142D          

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M  END

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M  END


  Mrv1652309112221142D          

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    0.7728    1.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311    2.0584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4563    0.7735    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
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
  6 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 26 34  1  0  0  0  0
  2 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC[C@@H]3[C@](C)(CC[C@@H]4[C@@]5(C)CCCC(C)(C)[C@@H]5CC[C@@]34C)C1CC1=C(O)C=C(O)C(O)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O3/c1-27(2)11-7-12-28(3)21(27)8-13-29(4)22(28)9-14-30(5)23(29)10-15-31(6)24(30)16-18-19(32)17-20(33)26(34)25(18)31/h17,21-24,32-34H,7-16H2,1-6H3/t21-,22+,23-,24?,28-,29+,30-,31?/m0/s1

> <INCHI_KEY>
JTOOVKGBFSOTNF-NHUMASMOSA-N

> <FORMULA>
C31H46O3

> <MOLECULAR_WEIGHT>
466.706

> <EXACT_MASS>
466.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.66696942976252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11R,14S)-2,6,6,10,14,23-hexamethylhexacyclo[12.11.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]pentacosa-17,19,21-triene-18,20,21-triol

> <JCHEM_LOGP>
7.855288568333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.242813604233413

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.81617093189718

> <JCHEM_PKA_STRONGEST_BASIC>
-5.596748721588104

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
137.79399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11R,14S)-2,6,6,10,14,23-hexamethylhexacyclo[12.11.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]pentacosa-17,19,21-triene-18,20,21-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.266   3.029   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.213   1.815   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.937   3.174   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.476   3.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.291   1.920   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.567   0.561   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.843  -0.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.382  -0.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.921  -0.694   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.645   0.665   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.184   0.718   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.460  -0.641   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.999  -0.589   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.538  -0.537   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.263   0.822   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.448   2.129   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.876   2.705   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.129   3.636   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.909   2.077   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.094   3.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.555   3.331   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.830   1.972   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.015   3.279   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.028   0.508   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.037  -0.671   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.610  -0.092   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.225  -0.766   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.116  -2.302   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.051   0.096   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.058   1.632   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.218   2.495   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.443   2.306   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.551   3.842   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.718   1.444   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24   34                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7    8   24                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13   19                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   11   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    5   10   23                                             
CONECT   23   22                                                            
CONECT   24    6    2   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   26    2                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₆O₃

Average Mass

466.7060 Da

Monoisotopic Mass

466.34470 Da

IUPAC Name

(1S,2R,5S,10S,11R,14S)-2,6,6,10,14,23-hexamethylhexacyclo[12.11.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]pentacosa-17,19,21-triene-18,20,21-triol

Traditional Name

(1S,2R,5S,10S,11R,14S)-2,6,6,10,14,23-hexamethylhexacyclo[12.11.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]pentacosa-17,19,21-triene-18,20,21-triol

CAS Registry Number

Not Available

SMILES

CC12CC[C@@H]3[C@](C)(CC[C@@H]4[C@@]5(C)CCCC(C)(C)[C@@H]5CC[C@@]34C)C1CC1=C(O)C=C(O)C(O)=C21

InChI Identifier

InChI=1S/C31H46O3/c1-27(2)11-7-12-28(3)21(27)8-13-29(4)22(28)9-14-30(5)23(29)10-15-31(6)24(30)16-18-19(32)17-20(33)26(34)25(18)31/h17,21-24,32-34H,7-16H2,1-6H3/t21-,22+,23-,24?,28-,29+,30-,31?/m0/s1

InChI Key

JTOOVKGBFSOTNF-NHUMASMOSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Fluorene
Indane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	7.86	ChemAxon
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	137.79 m³·mol⁻¹	ChemAxon
Polarizability	56.67 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

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

101967075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

De Pasquale R, Circosta C, Occhiuto F, De Stefano S, De Rosa S: Central nervous system activity of terpenoids from marine sponge. Pharmacol Res Commun. 1988 Dec;20 Suppl 5:23-6. doi: 10.1016/s0031-6989(88)80833-6. [PubMed:2907790 ]
LOTUS database [Link]

Showing NP-Card for (4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol (NP0318635)

MOL for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

3D MOL for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

3D SDF for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

3D-SDF for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

PDB for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

3D PDB for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

SMILES for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

INCHI for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

Structure for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)

3D Structure for NP0318635 ((4as,6ar,6bs,13bs,15ar,15bs)-4,4,6a,8a,13b,15b-hexamethyl-1h,2h,3h,4ah,5h,6h,6bh,7h,8h,13h,13ah,14h,15h,15ah-indeno[2,1-a]chrysene-9,10,12-triol)