NP-MRD: Showing NP-Card for Spirasine I (NP0050816)

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Record Information

Version

2.0

Created at

2022-04-27 22:09:33 UTC

Updated at

2022-04-27 22:09:33 UTC

NP-MRD ID

NP0050816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spirasine I

Description

(1R,5R,6S,11R,12S,14S,17R,20S,21S)-21-hydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]Docos-15-en-19-one belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. Spirasine I is found in Spiraea japonica, Spiraea japonica var. fortunei and Thalictrum javanicum. Based on a literature review very few articles have been published on (1R,5R,6S,11R,12S,14S,17R,20S,21S)-21-hydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0¹,¹¹.0⁵,²⁰.0⁶,¹⁰.0¹²,¹⁷.0¹⁷,²¹]Docos-15-en-19-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200092D          

 26 32  0  0  1  0            999 V2000
    3.0110    1.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2459    2.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5487    3.2243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7163    3.1454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4277    2.3807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1028    1.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    1.7202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1223    2.5172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2852    3.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641    3.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869    4.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7217    2.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0233    1.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    1.0031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3791    0.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400    2.1676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4580    1.6701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3936    1.5338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7052    2.2977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5280    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249    1.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0238    1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8295    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    1.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958    3.9139    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
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
  7 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  1  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  6  0  0  0
  3 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
 19 23  1  0  0  0  0
 13 24  1  0  0  0  0
  7 25  1  1  0  0  0
  3 26  1  6  0  0  0
M  END


  Mrv1652304282200092D          

 26 32  0  0  1  0            999 V2000
    3.0110    1.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2459    2.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5487    3.2243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7163    3.1454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4277    2.3807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1028    1.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    1.7202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1223    2.5172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2852    3.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641    3.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869    4.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7217    2.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0233    1.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    1.0031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3791    0.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400    2.1676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4580    1.6701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3936    1.5338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7052    2.2977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5280    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249    1.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0238    1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8295    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    1.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958    3.9139    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
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
  7 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  1  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  6  0  0  0
  3 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
 19 23  1  0  0  0  0
 13 24  1  0  0  0  0
  7 25  1  1  0  0  0
  3 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@]23CC(=O)[C@H]4[C@]56CCC[C@@]4(C)[C@@H]4OCCN4[C@@H]5[C@H]2C[C@H]1C[C@]36O

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO3/c1-12-9-20-11-15(24)16-19(2)4-3-5-21(16)17(23-6-7-26-18(19)23)14(20)8-13(12)10-22(20,21)25/h9,13-14,16-18,25H,3-8,10-11H2,1-2H3/t13-,14+,16+,17+,18-,19+,20-,21+,22-/m0/s1

> <INCHI_KEY>
BDYVYNKEWLPLCY-ZPNNCZIXSA-N

> <FORMULA>
C22H29NO3

> <MOLECULAR_WEIGHT>
355.478

> <EXACT_MASS>
355.214743798

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.87521685767389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,6S,11R,12S,14S,17R,20S,21S)-21-hydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0^{1,11}.0^{5,20}.0^{6,10}.0^{12,17}.0^{17,21}]docos-15-en-19-one

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.9113589033333338

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.01673293758879

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.84609263019523

> <JCHEM_PKA_STRONGEST_BASIC>
7.490996270817422

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
97.39649999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6S,11R,12S,14S,17R,20S,21S)-21-hydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0^{1,11}.0^{5,20}.0^{6,10}.0^{12,17}.0^{17,21}]docos-15-en-19-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.620   3.609   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.059   5.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.758   6.019   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.204   5.871   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.665   4.444   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.925   3.592   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.460   3.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.228   4.699   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.532   6.263   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.986   6.787   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.216   8.309   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.347   4.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.910   2.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.803   1.872   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.708   1.807   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.748   3.467   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.008   4.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.722   3.117   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.468   2.863   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.050   4.289   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.586   4.176   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.953   2.681   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.644   1.869   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.415   2.653   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.702   2.300   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.912   7.306   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20   26                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   18                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15   25                                             
CONECT    8    7    9   12   17                                             
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    7                                                       
CONECT   16   14   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
CONECT   24   13                                                            
CONECT   25    7                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₉NO₃

Average Mass

355.4780 Da

Monoisotopic Mass

355.21474 Da

IUPAC Name

(1R,5R,6S,11R,12S,14S,17R,20S,21S)-21-hydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0^{1,11}.0^{5,20}.0^{6,10}.0^{12,17}.0^{17,21}]docos-15-en-19-one

Traditional Name

(1R,5R,6S,11R,12S,14S,17R,20S,21S)-21-hydroxy-5,15-dimethyl-7-oxa-10-azaheptacyclo[12.6.2.0^{1,11}.0^{5,20}.0^{6,10}.0^{12,17}.0^{17,21}]docos-15-en-19-one

CAS Registry Number

Not Available

SMILES

CC1=C[C@]23CC(=O)[C@H]4[C@]56CCC[C@@]4(C)[C@@H]4OCCN4[C@@H]5[C@H]2C[C@H]1C[C@]36O

InChI Identifier

InChI=1S/C22H29NO3/c1-12-9-20-11-15(24)16-19(2)4-3-5-21(16)17(23-6-7-26-18(19)23)14(20)8-13(12)10-22(20,21)25/h9,13-14,16-18,25H,3-8,10-11H2,1-2H3/t13-,14+,16+,17+,18-,19+,20-,21+,22-/m0/s1

InChI Key

BDYVYNKEWLPLCY-ZPNNCZIXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Spiraea japonica	LOTUS Database	35616633
Spiraea japonica var. fortunei	Plant	KNApSAcK
Thalictrum javanicum Blume	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Piperidine
Tertiary alcohol
Oxazolidine
Cyclic alcohol
Ketone
Hemiaminal
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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
logP	1.43	ALOGPS
logP	1.91	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	7.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	97.4 m³·mol⁻¹	ChemAxon
Polarizability	38.88 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162929145

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Spirasine I (NP0050816)

MOL for NP0050816 (Spirasine I)

3D MOL for NP0050816 (Spirasine I)

3D SDF for NP0050816 (Spirasine I)

3D-SDF for NP0050816 (Spirasine I)

PDB for NP0050816 (Spirasine I)

3D PDB for NP0050816 (Spirasine I)

SMILES for NP0050816 (Spirasine I)

INCHI for NP0050816 (Spirasine I)

Structure for NP0050816 (Spirasine I)

3D Structure for NP0050816 (Spirasine I)