NP-MRD: Showing NP-Card for dehydrocannabispiran (NP0045009)

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Record Information

Version

2.0

Created at

2022-03-10 18:52:40 UTC

Updated at

2022-03-10 22:20:04 UTC

NP-MRD ID

NP0045009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dehydrocannabispiran

Description

Dehydrocannabispiran or (R)-2‚Äö√Ñ‚â§,3‚Äö√Ñ‚â§-Dihydro-7‚Äö√Ñ‚â§-hydroxy-5‚Äö√Ñ‚â§-methoxyspiro[2-cyclohexene-1,1‚Äö√Ñ‚â§-[1H]inden]-4-one belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Dehydrocannabispiran is also classified as a spiroindane compound. Spiroindanes were first isolated and identified as cannabis constituents in 1976. Spiroindane compounds are indane compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]Pentane. Dehydrocannabispiran is neutral, hydrophobic molecule that is insoluble in water. Dehydrocannabispiran is one of several spiroindane, non-cannabinoid phenols that are known in cannabis plants. It was first identified from the dried leaves of a South African C. Savita variant grown in France in 1976 (DOI: 10.1016/0040-4020(76)80149-4). A year later it was isolated from the South African cannabis variant grown in Mississippi and was named as dehydrocannabispiran (DOI: 10.1016/0040-4020(77)80249-4). Dehydrocannabispiran was also identified in the Japanese Kumamoto strain (DOI:10.1248/Cpb.26.3641). Its structure resembles a synthetic compound which was found to potentiate the estrogenic activity of Stilbestrol (DOI: 10.1016/0040-4020(77)80249-4, PMID: 1255671 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    5.0310    0.5945    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3020   -0.4130   -0.6349 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9272   -0.4526   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -1.4325   -1.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004   -1.4380   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0732   -2.4293   -1.5605 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -0.4885   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.4795    0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759    0.4748    0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0009    1.3786    1.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1285    0.3763    1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2382   -0.2678    0.2304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0982   -1.4322    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -1.2684    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968    0.0842    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2159    0.2298    0.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408    1.2620   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206    0.7455   -0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8786    0.4312    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0938    0.5836   -0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6188    1.6167   -0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754   -2.1619   -1.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5295   -3.1165   -2.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8433    1.2673    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3748    2.2286    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4871    1.7099    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -0.3692    2.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0354    0.8504    1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147   -2.4306    0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0950   -2.0981    0.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0538    1.9611    0.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151    1.8561   -1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306    0.1482   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1126    1.5203   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  7 12  1  0
 12 11  1  0
 11 10  1  0
 12 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  2  0
  4  3  1  0
 12 13  1  1
 10  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  9 24  1  0
  6 23  1  0
  4 22  1  0
 11 27  1  0
 11 28  1  0
 10 25  1  0
 10 26  1  0
 18 33  1  0
 18 34  1  0
 17 31  1  0
 17 32  1  0
 14 30  1  0
 13 29  1  0
M  END


  Mrv1652303192001303D          

 18 20  0  0  0  0            999 V2000
    5.1949    0.4298    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3952   -1.0770   -2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9383    1.5825   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018   -0.4261    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778   -1.4274   -1.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.0011   -0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0004   -0.5452    1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -0.5736   -1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738    0.4301    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077   -0.5663   -1.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7203    1.0157    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086   -0.0629   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125    0.4200    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404   -0.0772   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.2020   -0.1058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5326    1.7224    1.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062    0.9215    2.0860 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789   -0.0791   -0.6777 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2  5  1  0  0  0  0
  2 10  1  0  0  0  0
  3  6  2  0  0  0  0
  3 11  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  5 15  1  0  0  0  0
  6 15  1  0  0  0  0
  7 15  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  2  0  0  0  0
  9 12  1  0  0  0  0
  9 13  2  0  0  0  0
 10 14  2  0  0  0  0
 11 16  2  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1)[C@@]1(CC2)CCC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h3,6,8-9,17H,2,4-5,7H2,1H3/t15-/m1/s1

> <INCHI_KEY>
MVYJADZNMQXLJB-OAHLLOKOSA-N

> <FORMULA>
C15H16O3

> <MOLECULAR_WEIGHT>
244.29

> <EXACT_MASS>
244.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.21923365066192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
2.795346842666667

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.508191266631396

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.33216128296867

> <JCHEM_PKA_STRONGEST_BASIC>
-4.651574482153948

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
70.1425

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0       5.195   0.430   0.281  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.395  -1.077  -2.060  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.938   1.583  -0.460  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.502  -0.426   0.917  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.478  -1.427  -1.022  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.818   1.001  -0.785  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.000  -0.545   1.169  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.067  -0.574  -1.401  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.374   0.430   0.727  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.708  -0.566  -1.170  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.720   1.016   0.630  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.909  -0.063  -0.426  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.012   0.420   0.919  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.140  -0.077  -0.022  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.302  -0.202  -0.106  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.533   1.722   1.282  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.506   0.922   2.086  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.279  -0.079  -0.678  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    5   10                                                       
CONECT    3    6   11                                                       
CONECT    4    7   11                                                       
CONECT    5    2   15                                                       
CONECT    6    3   15                                                       
CONECT    7    4   15                                                       
CONECT    8   10   12                                                       
CONECT    9   12   13                                                       
CONECT   10    2    8   14                                                  
CONECT   11    3    4   16                                                  
CONECT   12    8    9   18                                                  
CONECT   13    9   14   17                                                  
CONECT   14   10   13   15                                                  
CONECT   15    5    6    7   14                                             
CONECT   16   11                                                            
CONECT   17   13                                                            
CONECT   18    1   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₃

Average Mass

244.2900 Da

Monoisotopic Mass

244.10994 Da

IUPAC Name

(1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one

Traditional Name

(1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1)[C@@]1(CC2)CCC(=O)C=C1

InChI Identifier

InChI=1S/C15H16O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h3,6,8-9,17H,2,4-5,7H2,1H3/t15-/m1/s1

InChI Key

MVYJADZNMQXLJB-OAHLLOKOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cannabis sativa	NULL	Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Indanes

Sub Class

Not Available

Direct Parent

Indanes

Alternative Parents

Substituents

Indane
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Alkyl aryl ether
Cyclic ketone
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.85	ALOGPS
logP	2.8	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.14 m³·mol⁻¹	ChemAxon
Polarizability	26.22 Å³	ChemAxon
Number of Rings	3	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

134714927

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for dehydrocannabispiran (NP0045009)

MOL for NP0045009 (dehydrocannabispiran)

3D MOL for NP0045009 (dehydrocannabispiran)

3D SDF for NP0045009 (dehydrocannabispiran)

3D-SDF for NP0045009 (dehydrocannabispiran)

PDB for NP0045009 (dehydrocannabispiran)

3D PDB for NP0045009 (dehydrocannabispiran)

SMILES for NP0045009 (dehydrocannabispiran)

INCHI for NP0045009 (dehydrocannabispiran)

Structure for NP0045009 (dehydrocannabispiran)

3D Structure for NP0045009 (dehydrocannabispiran)