NP-MRD: Showing NP-Card for Hyptadienic acid (NP0071354)

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Record Information

Version

2.0

Created at

2022-04-28 16:44:27 UTC

Updated at

2022-04-28 16:44:27 UTC

NP-MRD ID

NP0071354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hyptadienic acid

Description

Hyptadienic acid, also known as hyptadienate, belongs to the class of organic compounds known as 3-carboxy steroids. These are steroid compounds that carry a carboxyl group at the C3-atom of the steroid backbone. Hyptadienic acid is found in Mesosphaerum suaveolens, Isodon effusus, Perilla frutescens, Perilla frutescens (L.) Britton var.japonica Hara and Salvia trijuga. Hyptadienic acid was first documented in 2004 (PMID: 14745168). Based on a literature review a small amount of articles have been published on Hyptadienic acid (PMID: 22574636) (PMID: 30520576) (PMID: 28823202).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218442D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282218442D          

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 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  9  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 15 21  1  6  0  0  0
 13 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 10 25  1  6  0  0  0
  5 26  1  1  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  1 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  0  0  0  0
 27 33  1  0  0  0  0
  1 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0071354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@]5(C)[C@@H](CC[C@@]34C)C(C)(C)C=C5CO)[C@@H]2[C@]1(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-18-10-13-30(24(32)33)15-14-26(4)20(23(30)29(18,7)34)8-9-22-27(26,5)12-11-21-25(2,3)16-19(17-31)28(21,22)6/h8,16,18,21-23,31,34H,9-15,17H2,1-7H3,(H,32,33)/t18-,21+,22+,23-,26-,27-,28+,29-,30+/m1/s1

> <INCHI_KEY>
YFLYOZWZPSYMPX-DCLYBNOZSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.13061483902383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,9S,10S,14S,15R,16R,19S)-15-hydroxy-8-(hydroxymethyl)-1,2,6,6,9,15,16-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-7,12-diene-19-carboxylic acid

> <ALOGPS_LOGP>
5.78

> <JCHEM_LOGP>
4.731462775000001

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.48554983624447

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.570990571710839

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6970544084422756

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
136.35989999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,9S,10S,14S,15R,16R,19S)-15-hydroxy-8-(hydroxymethyl)-1,2,6,6,9,15,16-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-7,12-diene-19-carboxylic acid

> <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       9.033   0.653   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.534   3.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.703  -0.645   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.454   3.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.914   3.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.247  -1.874   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.377  -1.411   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.114  -2.115   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.374   3.437   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.166   3.460   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.164   4.759   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.994   3.367   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.928   3.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.324   1.632   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.462   0.098   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.703  -2.008   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.831  -3.056   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.838   3.084   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.832   1.945   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.385  -0.744   0.000  0.00  0.00           C+0
CONECT    1    2    6   29   34                                             
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10   26                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11   25                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18   22                                             
CONECT   14   13    9   15                                                  
CONECT   15   14   16   20   21                                             
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   15                                                            
CONECT   22   13   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   10                                                            
CONECT   26    5                                                            
CONECT   27    2   28   32   33                                             
CONECT   28   27   29                                                       
CONECT   29   28    1   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   27                                                            
CONECT   33   27                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Hyptadienate	Generator

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(1S,2R,5S,9S,10S,14S,15R,16R,19S)-15-hydroxy-8-(hydroxymethyl)-1,2,6,6,9,15,16-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-7,12-diene-19-carboxylic acid

Traditional Name

(1S,2R,5S,9S,10S,14S,15R,16R,19S)-15-hydroxy-8-(hydroxymethyl)-1,2,6,6,9,15,16-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-7,12-diene-19-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@]5(C)[C@@H](CC[C@@]34C)C(C)(C)C=C5CO)[C@@H]2[C@]1(C)O)C(O)=O

InChI Identifier

InChI=1S/C30H46O4/c1-18-10-13-30(24(32)33)15-14-26(4)20(23(30)29(18,7)34)8-9-22-27(26,5)12-11-21-25(2,3)16-19(17-31)28(21,22)6/h8,16,18,21-23,31,34H,9-15,17H2,1-7H3,(H,32,33)/t18-,21+,22+,23-,26-,27-,28+,29-,30+/m1/s1

InChI Key

YFLYOZWZPSYMPX-DCLYBNOZSA-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
Hyptis suaveolens	LOTUS Database	35616633
Isodon effusus	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Perilla frutescens (L.) Britton var.japonica Hara	Plant	KNApSAcK
Salvia trijuga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-carboxy steroids. These are steroid compounds that carry a carboxyl group at the C3-atom of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid acids

Direct Parent

3-carboxy steroids

Alternative Parents

Substituents

3-carboxy steroid
Delta-5-steroid
Tertiary alcohol
Cyclic alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	5.78	ALOGPS
logP	4.73	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.36 m³·mol⁻¹	ChemAxon
Polarizability	55.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00030505

Chemspider ID

10277042

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14605533

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Al-Jaber HI, Abrouni KK, Al-Qudah MA, Abu Zarga MH: New terpenes from Salvia palaestina Benth. and Salvia syriaca L. growing wild in Jordan. J Asian Nat Prod Res. 2012;14(7):618-25. doi: 10.1080/10286020.2012.682151. Epub 2012 May 10. [PubMed:22574636 ]
Ferhat M, Kabouchea Z, Fujimoto Y, Araya H: Two New Triterpenes and Other Compounds from Mentha aquatica (Lamiaceae). Nat Prod Commun. 2017 Apr;12(4):483-486. [PubMed:30520576 ]
Beladjila KA, Cotugno R, Berrehal D, Kabouche Z, De Tommasi N, Braca A, De Leo M: Cytotoxic triterpenes from Salvia buchananii roots. Nat Prod Res. 2018 Sep;32(17):2025-2030. doi: 10.1080/14786419.2017.1365072. Epub 2017 Aug 20. [PubMed:28823202 ]
Banno N, Akihisa T, Tokuda H, Yasukawa K, Higashihara H, Ukiya M, Watanabe K, Kimura Y, Hasegawa J, Nishino H: Triterpene acids from the leaves of Perilla frutescens and their anti-inflammatory and antitumor-promoting effects. Biosci Biotechnol Biochem. 2004 Jan;68(1):85-90. doi: 10.1271/bbb.68.85. [PubMed:14745168 ]

Showing NP-Card for Hyptadienic acid (NP0071354)

MOL for NP0071354 (Hyptadienic acid)

3D MOL for NP0071354 (Hyptadienic acid)

3D SDF for NP0071354 (Hyptadienic acid)

3D-SDF for NP0071354 (Hyptadienic acid)

PDB for NP0071354 (Hyptadienic acid)

3D PDB for NP0071354 (Hyptadienic acid)

SMILES for NP0071354 (Hyptadienic acid)

INCHI for NP0071354 (Hyptadienic acid)

Structure for NP0071354 (Hyptadienic acid)

3D Structure for NP0071354 (Hyptadienic acid)