NPASS Compound

Structure

NPC474120 OpenBabel07101718182D 23 22 0 0 0 0 0 0 0 0999 V2000 14.5000 -10.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0000 -9.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5000 -8.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 -8.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0000 -7.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 -7.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5000 -6.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -6.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0000 -5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5000 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -1.5000 0.0000 S 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 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 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 1 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 17 18 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 23 2 0 0 0 0 21 23 2 0 0 0 0 22 23 1 0 0 0 0 M CHG 1 19 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	349.24
Volume:	372.236
LogP:	6.219
LogD:	3.455
LogS:	-6.778
# Rotatable Bonds:	18
TPSA:	66.43
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.18
Synthetic Accessibility Score:	2.337
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.013
MDCK Permeability:	1.3497262443706859e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	99.23432159423828%
Volume Distribution (VD):	1.431
Pgp-substrate:	0.9336325526237488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.14
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.239
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	2.555
Half-life (T1/2):	0.015

ADMET: Toxicity

hERG Blockers:	0.442
Human Hepatotoxicity (H-HT):	0.628
Drug-inuced Liver Injury (DILI):	0.254
AMES Toxicity:	0.412
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.341
Skin Sensitization:	0.972
Carcinogencity:	0.531
Eye Corrosion:	0.995
Eye Irritation:	0.958
Respiratory Toxicity:	0.978

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474120

Natural Product ID:	NPC474120
*Common Name:**	Sodium Octadecyl Sulfate
IUPAC Name:	sodium;octadecyl sulfate
Synonyms:	Sodium Octadecyl Sulfate
Standard InCHIKey:	NWZBFJYXRGSRGD-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C18H38O4S.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22-23(19,20)21;/h2-18H2,1H3,(H,19,20,21);/q;+1/p-1
SMILES:	CCCCCCCCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462322
PubChem CID:	23673604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000403] Organic sulfuric acids and derivatives [CHEMONTID:0003455] Sulfuric acid esters [CHEMONTID:0001185] Sulfuric acid monoesters

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23405	Sidnyum turbinatum	n.a.	n.a.	n.a.	n.a.	Mediterranean	n.a.	PMID[11430005]
NPO23405	Sidnyum turbinatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Ki	1
Others	1
Potency	36

Activity Type	# Activity
Cell Line	1
Individual Protein	5
Others	33

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	410.0	ug.mL-1	PMID[573673]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	54941	nM	PMID[1800632]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	54941	nM	DrugMatrix in vitro pharmacology data
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	61130.6	nM	PMID[9644070]
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	54941	nM	PMID[22624550]
NPT2	Others	Unspecified		Ki	=	330.0	nM	PMID[573674]
NPT35	Others	n.a.		CMC	<	100.0	uM	PMID[573674]
NPT2	Others	Unspecified		Potency	n.a.	30895.6	nM	PMID[10924160]
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PMID[26636180]
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	DrugMatrix in vivo data: Pathology
NPT2	Others	Unspecified		Potency	n.a.	43641.2	nM	PMID[23819826]
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PMID[23303337]
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PMID[24893224]
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	DOI[10.1039/C4MD00211C]
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PMID[26465675]
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PMID[17618015]
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PMID[20598551]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	43641.2	nM	PMID[9655875]
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PMID[21871694]
NPT2	Others	Unspecified		Potency	n.a.	30895.6	nM	PMID[25464882]
NPT2	Others	Unspecified		Potency	n.a.	38895.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PMID[18183025]
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PMID[12182864]
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PMID[22360613]
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PMID[10869203]
NPT2	Others	Unspecified		Potency	n.a.	34665.4	nM	PMID[20041704]
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PMID[22037378]
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PMID[16506833]
NPT2	Others	Unspecified		Potency	n.a.	43641.2	nM	PMID[22500574]
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PMID[17315955]
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PMID[20146433]
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	DOI[10.6019/CHEMBL3301361]
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PMID[19835393]
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PMID[10924160]
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PMID[20368407]
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	Open TG-GATES in vivo data: Organ Weight
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474120 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1753
0.1-0.2	24111
0.2-0.3	13722
0.3-0.4	2636
0.4-0.5	338
0.5-0.6	90
0.6-0.7	37
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474089
0.9355	High Similarity	NPC272426
0.7949	Intermediate Similarity	NPC474125
0.7949	Intermediate Similarity	NPC474126
0.7742	Intermediate Similarity	NPC474048
0.7429	Intermediate Similarity	NPC139131
0.7429	Intermediate Similarity	NPC12231
0.7429	Intermediate Similarity	NPC152759
0.7429	Intermediate Similarity	NPC272998
0.7429	Intermediate Similarity	NPC185538
0.7429	Intermediate Similarity	NPC291158
0.7429	Intermediate Similarity	NPC181516
0.7429	Intermediate Similarity	NPC205141
0.7368	Intermediate Similarity	NPC469714
0.7368	Intermediate Similarity	NPC473568
0.7368	Intermediate Similarity	NPC469712
0.7297	Intermediate Similarity	NPC474914
0.7297	Intermediate Similarity	NPC474392
0.7222	Intermediate Similarity	NPC139569
0.7143	Intermediate Similarity	NPC126915
0.7105	Intermediate Similarity	NPC128996
0.7105	Intermediate Similarity	NPC74352
0.7027	Intermediate Similarity	NPC97967
0.7	Intermediate Similarity	NPC152008
0.6923	Remote Similarity	NPC197039
0.6857	Remote Similarity	NPC112242
0.6857	Remote Similarity	NPC24506
0.6857	Remote Similarity	NPC163556
0.6857	Remote Similarity	NPC185041
0.6857	Remote Similarity	NPC147096
0.6857	Remote Similarity	NPC236797
0.6857	Remote Similarity	NPC225783
0.6579	Remote Similarity	NPC223374
0.6579	Remote Similarity	NPC196442
0.6579	Remote Similarity	NPC301398
0.6579	Remote Similarity	NPC86545
0.6486	Remote Similarity	NPC193062
0.6486	Remote Similarity	NPC319034
0.6486	Remote Similarity	NPC66124
0.6486	Remote Similarity	NPC72324
0.6486	Remote Similarity	NPC147054
0.6486	Remote Similarity	NPC1748
0.6341	Remote Similarity	NPC471282
0.6341	Remote Similarity	NPC221022
0.6316	Remote Similarity	NPC286498
0.6286	Remote Similarity	NPC279895
0.6279	Remote Similarity	NPC203531
0.6279	Remote Similarity	NPC236579
0.6216	Remote Similarity	NPC122962
0.6216	Remote Similarity	NPC267243
0.619	Remote Similarity	NPC28598
0.619	Remote Similarity	NPC161097
0.6047	Remote Similarity	NPC53541
0.6	Remote Similarity	NPC47363
0.6	Remote Similarity	NPC287231
0.6	Remote Similarity	NPC469781
0.6	Remote Similarity	NPC62014
0.6	Remote Similarity	NPC80641
0.5952	Remote Similarity	NPC31551
0.5952	Remote Similarity	NPC219536
0.587	Remote Similarity	NPC30195
0.587	Remote Similarity	NPC12438
0.5854	Remote Similarity	NPC177022
0.5814	Remote Similarity	NPC149299
0.5814	Remote Similarity	NPC40597
0.5814	Remote Similarity	NPC12156
0.5814	Remote Similarity	NPC160261
0.5814	Remote Similarity	NPC165533
0.5814	Remote Similarity	NPC250028
0.5814	Remote Similarity	NPC256163
0.5814	Remote Similarity	NPC469759
0.5806	Remote Similarity	NPC171090
0.5789	Remote Similarity	NPC40965
0.5745	Remote Similarity	NPC324004
0.5745	Remote Similarity	NPC289484
0.5745	Remote Similarity	NPC249754
0.5745	Remote Similarity	NPC328497
0.5745	Remote Similarity	NPC319709
0.5714	Remote Similarity	NPC55678
0.5714	Remote Similarity	NPC305660
0.5714	Remote Similarity	NPC201622
0.5714	Remote Similarity	NPC54980
0.5714	Remote Similarity	NPC22903
0.5682	Remote Similarity	NPC209970
0.5682	Remote Similarity	NPC171736
0.5682	Remote Similarity	NPC149184
0.5682	Remote Similarity	NPC196924
0.5682	Remote Similarity	NPC307783
0.5682	Remote Similarity	NPC216630
0.5676	Remote Similarity	NPC110884
0.5652	Remote Similarity	NPC215358
0.5641	Remote Similarity	NPC322892
0.5625	Remote Similarity	NPC106872
0.56	Remote Similarity	NPC287811

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	2133
0.1-0.2	5561
0.2-0.3	1103
0.3-0.4	287
0.4-0.5	49
0.5-0.6	8
0.6-0.7	5
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD1461	Approved
0.9355	High Similarity	NPD908	Approved
0.9355	High Similarity	NPD907	Approved
0.7436	Intermediate Similarity	NPD1460	Approved
0.7429	Intermediate Similarity	NPD5383	Approved
0.7429	Intermediate Similarity	NPD2272	Approved
0.7179	Intermediate Similarity	NPD5799	Discontinued
0.7073	Intermediate Similarity	NPD1462	Approved
0.7	Intermediate Similarity	NPD7536	Approved
0.6098	Remote Similarity	NPD3206	Approved
0.6	Remote Similarity	NPD2699	Approved
0.5957	Remote Similarity	NPD4840	Approved
0.5745	Remote Similarity	NPD3211	Approved
0.5682	Remote Similarity	NPD2270	Approved
0.5625	Remote Similarity	NPD6125	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data