NP-MRD: Showing NP-Card for Heteronemin (NP0079082)

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Record Information

Version

2.0

Created at

2022-04-29 00:08:59 UTC

Updated at

2025-11-24 01:02:15 UTC

NP-MRD ID

NP0079082

Natural Product DOI

https://doi.org/10.57994/4987

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Heteronemin

Description

Heteronemin belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. Heteronemin is found in Brachiaster sp., Collospongia auris, Doriprismatica atromarginata, Hyrtios erectus and Tubastraea micranthus. Heteronemin was first documented in 2021 (PMID: 34572295). Based on a literature review a significant number of articles have been published on Heteronemin (PMID: 35200753) (PMID: 35151786) (PMID: 34381775) (PMID: 34066940) (PMID: 41237174).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202092D          

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  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  3  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  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
 15 23  1  0  0  0  0
 23 19  1  6  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 18 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 15 32  1  6  0  0  0
 14 33  1  6  0  0  0
 11 34  1  6  0  0  0
  2 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0079082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1OC=C2[C@H]1[C@@]1(C)[C@H](O)C[C@@H]3[C@@]4(C)CCCC(C)(C)[C@@H]4CC[C@@]3(C)[C@@H]1C[C@@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O6/c1-16(30)34-19-13-22-28(6)12-9-20-26(3,4)10-8-11-27(20,5)21(28)14-23(32)29(22,7)24-18(19)15-33-25(24)35-17(2)31/h15,19-25,32H,8-14H2,1-7H3/t19-,20-,21+,22-,23+,24+,25-,27-,28+,29+/m0/s1

> <INCHI_KEY>
VYIQDOVNWPEWRJ-JVQIYTTCSA-N

> <FORMULA>
C29H44O6

> <MOLECULAR_WEIGHT>
488.665

> <EXACT_MASS>
488.313789137

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.8019899881999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4S,8S,9R,10S,11R,13R,14S,19S)-4-(acetyloxy)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5-en-8-yl acetate

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
4.0036819203333325

> <ALOGPS_LOGS>
-5.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.663679375884552

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9459066409880963

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
131.1591

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,8S,9R,10S,11R,13R,14S,19S)-4-(acetyloxy)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5-en-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      11.981   2.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.191   0.793   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.941  -0.552   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.481  -0.575   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.271   0.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.521   2.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.511  -2.115   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.774  -1.411   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.151  -1.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.611  -1.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.861  -0.505   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.651   0.817   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.902   2.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.362   2.185   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.572   0.864   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.321  -0.482   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.531  -1.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.991  -1.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.242  -0.435   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.740  -0.092   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.603   1.442   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.019   2.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.032   0.887   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.362   3.548   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.233   4.596   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.762   4.143   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.576   6.097   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.201  -3.102   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.661  -3.078   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.871  -4.400   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.912  -1.733   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.822   2.209   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.612   3.531   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.071  -1.827   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.442   2.139   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12   35                                             
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7    8                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16   34                                             
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16   23   32                                             
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   15   19                                                  
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   18   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   15                                                            
CONECT   33   14                                                            
CONECT   34   11                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₄O₆

Average Mass

488.6650 Da

Monoisotopic Mass

488.31379 Da

IUPAC Name

(1R,2S,4S,8S,9R,10S,11R,13R,14S,19S)-4-(acetyloxy)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5-en-8-yl acetate

Traditional Name

(1R,2S,4S,8S,9R,10S,11R,13R,14S,19S)-4-(acetyloxy)-11-hydroxy-1,10,14,18,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5-en-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1OC=C2[C@H]1[C@@]1(C)[C@H](O)C[C@@H]3[C@@]4(C)CCCC(C)(C)[C@@H]4CC[C@@]3(C)[C@@H]1C[C@@H]2OC(C)=O

InChI Identifier

InChI=1S/C29H44O6/c1-16(30)34-19-13-22-28(6)12-9-20-26(3,4)10-8-11-27(20,5)21(28)14-23(32)29(22,7)24-18(19)15-33-25(24)35-17(2)31/h15,19-25,32H,8-14H2,1-7H3/t19-,20-,21+,22-,23+,24+,25-,27-,28+,29+/m0/s1

InChI Key

VYIQDOVNWPEWRJ-JVQIYTTCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2025-11-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2025-11-23	View Spectrum

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
Brachiaster sp.	-	KNApSAcK
Collospongia auris	LOTUS Database	35616633
Doriprismatica atromarginata	LOTUS Database	35616633
Glossodoris hikuerensis		Not Available
Hyrtios erectus	LOTUS Database	35616633
Tubastraea micranthus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Hydroxysteroid
7-hydroxysteroid
16-oxasteroid
Steroid
Dicarboxylic acid or derivatives
Cyclic alcohol
Dihydrofuran
Carboxylic acid ester
Secondary alcohol
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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	4.98	ALOGPS
logP	4	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	14.66	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	131.16 m³·mol⁻¹	ChemAxon
Polarizability	55.8 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

C00043573

Chemspider ID

10208706

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21589810

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Acquah KS, Beukes DR, Seldon R, Jordaan A, Sunassee SN, Warner DF, Gammon DW: Identification of Antimycobacterial Natural Products from a Library of Marine Invertebrate Extracts. Medicines (Basel). 2022 Jan 28;9(2). pii: medicines9020009. doi: 10.3390/medicines9020009. [PubMed:35200753 ]
Chung CC, Huang TY, Chu HR, De Luca R, Candelotti E, Huang CH, Yang YSH, Incerpi S, Pedersen JZ, Lin CY, Huang HM, Lee SY, Li ZL, ChangOu CA, Li WS, Davis PJ, Lin HY, Whang-Peng J, Wang K: Heteronemin and tetrac derivatives suppress non-small cell lung cancer growth via ERK1/2 inhibition. Food Chem Toxicol. 2022 Mar;161:112850. doi: 10.1016/j.fct.2022.112850. Epub 2022 Feb 10. [PubMed:35151786 ]
Chen HL, Su YC, Chen HC, Su JH, Wu CY, Wang SW, Lin IP, Chen CY, Lee CH: Heteronemin Suppresses Lymphangiogenesis through ARF-1 and MMP-9/VE-Cadherin/Vimentin. Biomedicines. 2021 Aug 29;9(9):1109. doi: 10.3390/biomedicines9091109. [PubMed:34572295 ]
Yang YSH, Li ZL, Huang TY, Su KW, Lin CY, Huang CH, Chen HY, Lu MC, Huang HM, Lee SY, Whang-Peng J, Lin HY, Davis PJ, Wang K: Effect of Estrogen on Heteronemin-Induced Anti-proliferative Effect in Breast Cancer Cells With Different Estrogen Receptor Status. Front Cell Dev Biol. 2021 Jul 26;9:688607. doi: 10.3389/fcell.2021.688607. eCollection 2021. [PubMed:34381775 ]
Fajardo-Orduna GR, Ledesma-Martinez E, Aguiniga-Sanchez I, Mora-Garcia ML, Weiss-Steider B, Santiago-Osorio E: Inhibitors of Chemoresistance Pathways in Combination with Ara-C to Overcome Multidrug Resistance in AML. A Mini Review. Int J Mol Sci. 2021 May 7;22(9):4955. doi: 10.3390/ijms22094955. [PubMed:34066940 ]
Xiao X, Zhang LT, Du CL, Zhang C, Lu YM, Su MZ, Li SW, Guo YW: Discovery of Scalarane Sesterterpenoids From the Mollusk Glossodoris hikuerensis Exhibiting Anticancer Effects Against Drug-resistant Lung Cancer Cells. Chem Biodivers. 2025 Nov 14:e03257. doi: 10.1002/cbdv.202503257. [PubMed:41237174 ]
DOI: 10.1002/cbdv.202503257
PMID: 41237174

Showing NP-Card for Heteronemin (NP0079082)

MOL for NP0079082 (Heteronemin)

3D MOL for NP0079082 (Heteronemin)

3D SDF for NP0079082 (Heteronemin)

3D-SDF for NP0079082 (Heteronemin)

PDB for NP0079082 (Heteronemin)

3D PDB for NP0079082 (Heteronemin)

SMILES for NP0079082 (Heteronemin)

INCHI for NP0079082 (Heteronemin)

Structure for NP0079082 (Heteronemin)

3D Structure for NP0079082 (Heteronemin)