NP-MRD: Showing NP-Card for (7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol (NP0328279)

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Record Information

Version

2.0

Created at

2022-09-12 11:36:33 UTC

Updated at

2022-09-12 11:36:33 UTC

NP-MRD ID

NP0328279

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol

Description

(7AS,11aS,11bS)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6H,7H,7aH,8H,9H,10H,11H,11aH,11bH-naphtho[1,2-d]azepin-11b-ol belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. (7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol is found in Tripterygium wilfordii. Based on a literature review very few articles have been published on (7aS,11aS,11bS)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6H,7H,7aH,8H,9H,10H,11H,11aH,11bH-naphtho[1,2-d]azepin-11b-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122213362D          

 23 25  0  0  1  0            999 V2000
    7.3719    3.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6124    3.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2902    3.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9347    2.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8530    2.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8139    2.0664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1452    1.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3505    1.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0282    2.5642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5823    1.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4210    3.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2331    3.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891    3.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1644    3.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7716    3.2446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9469    3.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    4.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643    3.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    2.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860    1.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8107    1.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035    2.5416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1397    1.7191    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
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0328279

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1=NC=C[C@]2(O)C(CC[C@H]3C(C)(C)CCC[C@]23C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H31NO2/c1-17(2)9-6-10-19(5)15(17)8-7-14-13-16(18(3,4)22)21-12-11-20(14,19)23/h11-13,15,22-23H,6-10H2,1-5H3/t15-,19-,20-/m0/s1

> <INCHI_KEY>
ZMXUXINJBFGKKP-YSSFQJQWSA-N

> <FORMULA>
C20H31NO2

> <MOLECULAR_WEIGHT>
317.473

> <EXACT_MASS>
317.235479242

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.08273828738881

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7aS,11aS,11bS)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6H,7H,7aH,8H,9H,10H,11H,11aH,11bH-naphtho[1,2-d]azepin-11b-ol

> <JCHEM_LOGP>
3.6477122049999986

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.20643293040364

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.270604305431576

> <JCHEM_PKA_STRONGEST_BASIC>
6.726535323536187

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
94.788

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(7aS,11aS,11bS)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6H,7H,7aH,9H,10H,11H-naphtho[1,2-d]azepin-11b-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      13.761   6.599   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.343   5.997   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.742   7.415   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.945   4.580   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.926   5.396   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      10.853   3.857   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.604   2.955   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.121   3.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.519   4.787   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.687   3.491   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.253   6.141   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.768   6.412   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.446   7.453   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.907   7.411   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.174   6.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.634   6.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.860   7.538   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.173   6.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.901   4.660   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.707   3.348   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.247   3.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.980   4.744   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.861   3.209   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   22                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11    5                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   15    9   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₁NO₂

Average Mass

317.4730 Da

Monoisotopic Mass

317.23548 Da

IUPAC Name

(7aS,11aS,11bS)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6H,7H,7aH,8H,9H,10H,11H,11aH,11bH-naphtho[1,2-d]azepin-11b-ol

Traditional Name

(7aS,11aS,11bS)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6H,7H,7aH,9H,10H,11H-naphtho[1,2-d]azepin-11b-ol

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1=NC=C[C@]2(O)C(CC[C@H]3C(C)(C)CCC[C@]23C)=C1

InChI Identifier

InChI=1S/C20H31NO2/c1-17(2)9-6-10-19(5)15(17)8-7-14-13-16(18(3,4)22)21-12-11-20(14,19)23/h11-13,15,22-23H,6-10H2,1-5H3/t15-,19-,20-/m0/s1

InChI Key

ZMXUXINJBFGKKP-YSSFQJQWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tripterygium wilfordii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepines

Sub Class

Not Available

Direct Parent

Azepines

Alternative Parents

Substituents

Azepine
Cyclic alcohol
Tertiary alcohol
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Imine
Organic oxygen compound
Organic nitrogen compound
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	3.65	ChemAxon
pKa (Strongest Acidic)	13.27	ChemAxon
pKa (Strongest Basic)	6.73	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.79 m³·mol⁻¹	ChemAxon
Polarizability	37.08 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

101172348

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol (NP0328279)

MOL for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

3D MOL for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

3D SDF for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

3D-SDF for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

PDB for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

3D PDB for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

SMILES for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

INCHI for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

Structure for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)

3D Structure for NP0328279 ((7as,11as,11bs)-4-(2-hydroxypropan-2-yl)-8,8,11a-trimethyl-6h,7h,7ah,9h,10h,11h-naphtho[1,2-d]azepin-11b-ol)