NP-MRD: Showing NP-Card for (1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol (NP0249307)

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Record Information

Version

2.0

Created at

2022-09-07 11:49:56 UTC

Updated at

2022-09-07 11:49:56 UTC

NP-MRD ID

NP0249307

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol

Description

10,23-Dihydro-24,25-dehydroaflavinine, also known as aflavinine-dihip, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol is found in Aspergillus leporis. (1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol was first documented in 2014 (PMID: 24736731). Based on a literature review a small amount of articles have been published on 10,23-Dihydro-24,25-dehydroaflavinine (PMID: 33348541).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213492D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072213492D          

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M  END
> <DATABASE_ID>
NP0249307

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]2(C)[C@H](C)CC[C@H](O)[C@]22CC[C@H]([C@@H]([C@H]12)C1=CNC2=CC=CC=C12)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO/c1-17(2)20-13-15-28-24(30)11-10-19(4)27(28,5)14-12-18(3)26(28)25(20)22-16-29-23-9-7-6-8-21(22)23/h6-9,16,18-20,24-26,29-30H,1,10-15H2,2-5H3/t18-,19-,20+,24+,25-,26+,27+,28+/m1/s1

> <INCHI_KEY>
PCTLYBSZNQCIJC-KEQHSKTGSA-N

> <FORMULA>
C28H39NO

> <MOLECULAR_WEIGHT>
405.626

> <EXACT_MASS>
405.30316488

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.46721484243528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,7R,7aS,8S,9R,11aS,11bS)-8-(1H-indol-3-yl)-4,7,11b-trimethyl-9-(prop-1-en-2-yl)-dodecahydro-1H-cyclohexa[e]naphthalen-1-ol

> <JCHEM_LOGP>
6.513159607999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.038978802789263

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.674329755094902

> <JCHEM_PKA_STRONGEST_BASIC>
-2.940419438017189

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
124.82009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,7R,7aS,8S,9R,11aS,11bS)-8-(1H-indol-3-yl)-4,7,11b-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.272   1.298   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.099  -0.197   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.011  -1.265   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.578  -0.623   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.877   0.255   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.806  -0.970   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.002  -2.077   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.081  -0.539   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.789   0.299   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.453   0.162   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.745  -0.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.666  -2.214   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.959  -3.051   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.295  -2.914   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.587  -3.752   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.216  -4.452   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.844  -5.153   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.552  -4.315   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.313  -5.837   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.631  -2.777   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.214  -2.066   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.098  -3.127   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.417  -2.848   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -1.150  -4.202   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -0.089  -5.318   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.209  -6.853   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.061  -7.724   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.451  -7.060   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.570  -5.525   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.300  -4.654   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14   20                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    7   21                                                  
CONECT   21   20    4   22                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   22   25                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
Aflavinine-dihip	MeSH

Chemical Formula

C₂₈H₃₉NO

Average Mass

405.6260 Da

Monoisotopic Mass

405.30316 Da

IUPAC Name

(1S,4R,7R,7aS,8S,9R,11aS,11bS)-8-(1H-indol-3-yl)-4,7,11b-trimethyl-9-(prop-1-en-2-yl)-dodecahydro-1H-cyclohexa[e]naphthalen-1-ol

Traditional Name

(1S,4R,7R,7aS,8S,9R,11aS,11bS)-8-(1H-indol-3-yl)-4,7,11b-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]2(C)[C@H](C)CC[C@H](O)[C@]22CC[C@H]([C@@H]([C@H]12)C1=CNC2=CC=CC=C12)C(C)=C

InChI Identifier

InChI=1S/C28H39NO/c1-17(2)20-13-15-28-24(30)11-10-19(4)27(28,5)14-12-18(3)26(28)25(20)22-16-29-23-9-7-6-8-21(22)23/h6-9,16,18-20,24-26,29-30H,1,10-15H2,2-5H3/t18-,19-,20+,24+,25-,26+,27+,28+/m1/s1

InChI Key

PCTLYBSZNQCIJC-KEQHSKTGSA-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
Aspergillus leporis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
3-alkylindole
Indole
Indole or derivatives
Substituted pyrrole
Benzenoid
Cyclic alcohol
Pyrrole
Heteroaromatic compound
Secondary alcohol
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	6.51	ChemAxon
pKa (Strongest Acidic)	14.67	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	124.82 m³·mol⁻¹	ChemAxon
Polarizability	48.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

10313763

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21725956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Silva JJD, Iamanaka BT, Ferranti LS, Massi FP, Taniwaki MH, Puel O, Lorber S, Frisvad JC, Fungaro MHP: Diversity within Aspergillus niger Clade and Description of a New Species: Aspergillus vinaceus sp. nov. J Fungi (Basel). 2020 Dec 17;6(4):371. doi: 10.3390/jof6040371. [PubMed:33348541 ]
Frisvad JC, Petersen LM, Lyhne EK, Larsen TO: Formation of sclerotia and production of indoloterpenes by Aspergillus niger and other species in section Nigri. PLoS One. 2014 Apr 15;9(4):e94857. doi: 10.1371/journal.pone.0094857. eCollection 2014. [PubMed:24736731 ]
LOTUS database [Link]

Showing NP-Card for (1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol (NP0249307)

MOL for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

3D MOL for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

3D SDF for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

3D-SDF for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

PDB for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

3D PDB for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

SMILES for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

INCHI for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

Structure for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)

3D Structure for NP0249307 ((1s,4r,4as,7r,7as,8s,9r,11as)-8-(1h-indol-3-yl)-4,4a,7-trimethyl-9-(prop-1-en-2-yl)-dodecahydrocyclohexa[e]naphthalen-1-ol)