NP-MRD: Showing NP-Card for (4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid (NP0322230)

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Record Information

Version

2.0

Created at

2022-09-12 00:53:22 UTC

Updated at

2022-09-12 00:53:22 UTC

NP-MRD ID

NP0322230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid

Description

(4AR,6bR,10S,12aR)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. (4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid is found in Lavandula multifida. It was first documented in 2002 (PMID: 31593387). Based on a literature review a significant number of articles have been published on (4aR,6bR,10S,12aR)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid (PMID: 27253005) (PMID: 27583328) (PMID: 36127157) (PMID: 36127156).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202532D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122202532D          

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  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 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
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  1  0  0  0
 13 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322230

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2(CCC3C(=CCC4[C@@]3(C)CCC3C(C)(C)[C@@H](O)CC[C@]43C)C2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O3/c1-25(2)15-16-29(24(31)32)14-9-19-18(20(29)17-25)7-8-22-27(19,5)12-10-21-26(3,4)23(30)11-13-28(21,22)6/h7,19-23,30H,8-17H2,1-6H3,(H,31,32)/t19?,20?,21?,22?,23-,27-,28-,29+/m0/s1

> <INCHI_KEY>
CMHDHRBVZJATBG-HATSMHDASA-N

> <FORMULA>
C29H46O3

> <MOLECULAR_WEIGHT>
442.684

> <EXACT_MASS>
442.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.27874867460415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,6bR,10S,12aR)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <JCHEM_LOGP>
6.294786313333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.48943329204533

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.718131403970828

> <JCHEM_PKA_STRONGEST_BASIC>
-0.835123092934488

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
129.14939999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,6bR,10S,12aR)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

> <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       7.119  -5.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.833  -6.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -1.183   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.106   0.151   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       7.796  -1.183   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.876  -1.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.956  -1.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.078  -1.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.793  -1.990   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.656  -3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.266  -5.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   32                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10   31                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   12   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   21   16   30                                             
CONECT   30   29                                                            
CONECT   31   13    6   32                                                  
CONECT   32   31    2                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(4AR,6BR,10S,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate	Generator

Chemical Formula

C₂₉H₄₆O₃

Average Mass

442.6840 Da

Monoisotopic Mass

442.34470 Da

IUPAC Name

(4aR,6bR,10S,12aR)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aR,6bR,10S,12aR)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2(CCC3C(=CCC4[C@@]3(C)CCC3C(C)(C)[C@@H](O)CC[C@]43C)C2C1)C(O)=O

InChI Identifier

InChI=1S/C29H46O3/c1-25(2)15-16-29(24(31)32)14-9-19-18(20(29)17-25)7-8-22-27(19,5)12-10-21-26(3,4)23(30)11-13-28(21,22)6/h7,19-23,30H,8-17H2,1-6H3,(H,31,32)/t19?,20?,21?,22?,23-,27-,28-,29+/m0/s1

InChI Key

CMHDHRBVZJATBG-HATSMHDASA-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
Lavandula multifida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	6.29	ChemAxon
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	129.15 m³·mol⁻¹	ChemAxon
Polarizability	53.28 Å³	ChemAxon
Number of Rings	5	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

163188842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Childhood Esophageal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593387 ]
Authors unspecified: Financial Toxicity and Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:27583328 ]
Gadot R, Najera R, Hirani S, Anand A, Storch E, Goodman WK, Shofty B, Sheth SA: Efficacy of deep brain stimulation for treatment-resistant obsessive-compulsive disorder: systematic review and meta-analysis. J Neurol Neurosurg Psychiatry. 2022 Sep 20. pii: jnnp-2021-328738. doi: 10.1136/jnnp-2021-328738. [PubMed:36127157 ]
Koggel LM, Lantinga MA, Buchner FL, Drenth JPH, Frankema JS, Heeregrave EJ, Heringa M, Numans ME, Siersema PD: Predictors for inappropriate proton pump inhibitor use: observational study in primary care. Br J Gen Pract. 2022 Jun 24. pii: BJGP.2022.0178. doi: 10.3399/BJGP.2022.0178. [PubMed:36127156 ]
LOTUS database [Link]

Showing NP-Card for (4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid (NP0322230)

MOL for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D MOL for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D SDF for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D-SDF for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

PDB for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D PDB for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

SMILES for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

INCHI for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

Structure for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D Structure for NP0322230 ((4ar,6br,10s,12ar)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid)