NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	143.11
Volume:	160.55
LogP:	0.918
LogD:	0.525
LogS:	-0.788
# Rotatable Bonds:	6
TPSA:	40.13
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	2.568
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.452
MDCK Permeability:	2.8297861717874184e-05
Pgp-inhibitor:	0.105
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.336
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	85.14691925048828%
Volume Distribution (VD):	0.279
Pgp-substrate:	21.1591739654541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.472
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	3.011
Half-life (T1/2):	0.548

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.8
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.792
Carcinogencity:	0.446
Eye Corrosion:	0.984
Eye Irritation:	0.986
Respiratory Toxicity:	0.269

Download Data

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

Natural Product: NPC156630

Natural Product ID:	NPC156630
*Common Name:**	Sodium Caprylate
IUPAC Name:	sodium;octanoate
Synonyms:	Sodium Caprylate
Standard InCHIKey:	BYKRNSHANADUFY-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C8H16O2.Na/c1-2-3-4-5-6-7-8(9)10;/h2-7H2,1H3,(H,9,10);/q;+1/p-1
SMILES:	CCCCCCCC(=O)[O-].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557076
PubChem CID:	23664772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0003086] Medium-chain fatty acids

*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
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	n.a.	Mysore, India	n.a.	DOI[10.1007/s11746-009-1435-y]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	roots	n.a.	n.a.	PMID[14738392]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[15387651]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15453426]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots and rhizomes	Shaoguan, Guangdong Province, China	2007-Dec	PMID[20540535]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	Endosperm	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	Hull Husk	n.a.	n.a.	Database[FooDB]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	Juice	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29812	Panax quinquefolium	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29812	Panax quinquefolium	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6108	Cocos nucifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	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
Ki	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ki	=	2380000.0	nM	PMID[568466]
NPT35	Others	n.a.		CMC	=	200000.0	uM	PMID[568466]

☑ 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 NPC156630 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	1252
0.1-0.2	18694
0.2-0.3	14775
0.3-0.4	6468
0.4-0.5	1089
0.5-0.6	198
0.6-0.7	125
0.7-0.8	49
0.8-0.85	16
0.85-0.9	25
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9143	High Similarity	NPC305660
0.9143	High Similarity	NPC201622
0.9143	High Similarity	NPC22903
0.9143	High Similarity	NPC54980
0.8889	High Similarity	NPC301585
0.8889	High Similarity	NPC113928
0.8889	High Similarity	NPC301696
0.8889	High Similarity	NPC31551
0.8889	High Similarity	NPC219536
0.8889	High Similarity	NPC201844
0.8889	High Similarity	NPC154186
0.8889	High Similarity	NPC279026
0.8889	High Similarity	NPC14227
0.8889	High Similarity	NPC261080
0.8649	High Similarity	NPC12156
0.8649	High Similarity	NPC250028
0.8649	High Similarity	NPC149299
0.8649	High Similarity	NPC40597
0.8649	High Similarity	NPC28598
0.8649	High Similarity	NPC256163
0.8649	High Similarity	NPC161097
0.8611	High Similarity	NPC268826
0.8571	High Similarity	NPC155263
0.8421	Intermediate Similarity	NPC53541
0.8421	Intermediate Similarity	NPC307783
0.8421	Intermediate Similarity	NPC196924
0.8421	Intermediate Similarity	NPC209970
0.8421	Intermediate Similarity	NPC216630
0.8421	Intermediate Similarity	NPC149184
0.8421	Intermediate Similarity	NPC171736
0.8378	Intermediate Similarity	NPC223249
0.8378	Intermediate Similarity	NPC183424
0.8378	Intermediate Similarity	NPC294085
0.8378	Intermediate Similarity	NPC80234
0.8378	Intermediate Similarity	NPC118968
0.8378	Intermediate Similarity	NPC214610
0.8205	Intermediate Similarity	NPC67462
0.8205	Intermediate Similarity	NPC203531
0.8205	Intermediate Similarity	NPC236579
0.8158	Intermediate Similarity	NPC165533
0.8056	Intermediate Similarity	NPC134782
0.8	Intermediate Similarity	NPC19305
0.8	Intermediate Similarity	NPC57499
0.8	Intermediate Similarity	NPC74845
0.8	Intermediate Similarity	NPC317128
0.8	Intermediate Similarity	NPC255837
0.7805	Intermediate Similarity	NPC55023
0.7805	Intermediate Similarity	NPC287231
0.7805	Intermediate Similarity	NPC8219
0.7805	Intermediate Similarity	NPC47363
0.7805	Intermediate Similarity	NPC273545
0.7714	Intermediate Similarity	NPC175342
0.7619	Intermediate Similarity	NPC145045
0.7619	Intermediate Similarity	NPC30195
0.7619	Intermediate Similarity	NPC63182
0.7619	Intermediate Similarity	NPC314679
0.7619	Intermediate Similarity	NPC52700
0.7619	Intermediate Similarity	NPC12438
0.7619	Intermediate Similarity	NPC105329
0.7568	Intermediate Similarity	NPC154642
0.7568	Intermediate Similarity	NPC80641
0.7568	Intermediate Similarity	NPC80396
0.75	Intermediate Similarity	NPC103286
0.75	Intermediate Similarity	NPC163746
0.7442	Intermediate Similarity	NPC324004
0.7442	Intermediate Similarity	NPC21844
0.7442	Intermediate Similarity	NPC328497
0.7442	Intermediate Similarity	NPC326957
0.7317	Intermediate Similarity	NPC71317
0.7317	Intermediate Similarity	NPC301528
0.7317	Intermediate Similarity	NPC176500
0.7317	Intermediate Similarity	NPC289686
0.7317	Intermediate Similarity	NPC129972
0.7297	Intermediate Similarity	NPC196442
0.7297	Intermediate Similarity	NPC223374
0.7297	Intermediate Similarity	NPC301398
0.7297	Intermediate Similarity	NPC86545
0.7273	Intermediate Similarity	NPC216130
0.7273	Intermediate Similarity	NPC477878
0.7273	Intermediate Similarity	NPC324793
0.7273	Intermediate Similarity	NPC131770
0.7273	Intermediate Similarity	NPC200618
0.7273	Intermediate Similarity	NPC106872
0.7222	Intermediate Similarity	NPC328710
0.7222	Intermediate Similarity	NPC18224
0.7209	Intermediate Similarity	NPC166287
0.7179	Intermediate Similarity	NPC73245
0.7143	Intermediate Similarity	NPC168982
0.7111	Intermediate Similarity	NPC304162
0.7111	Intermediate Similarity	NPC26253
0.7073	Intermediate Similarity	NPC325452
0.7073	Intermediate Similarity	NPC248763
0.7027	Intermediate Similarity	NPC286498
0.7027	Intermediate Similarity	NPC154396
0.7	Intermediate Similarity	NPC81263
0.6957	Remote Similarity	NPC55678
0.6957	Remote Similarity	NPC90904
0.6957	Remote Similarity	NPC224227
0.6957	Remote Similarity	NPC305182
0.6923	Remote Similarity	NPC252843
0.6923	Remote Similarity	NPC109026
0.6923	Remote Similarity	NPC128996
0.6889	Remote Similarity	NPC180534
0.6857	Remote Similarity	NPC79887
0.6857	Remote Similarity	NPC174368
0.6857	Remote Similarity	NPC42403
0.6857	Remote Similarity	NPC29561
0.6857	Remote Similarity	NPC196434
0.6857	Remote Similarity	NPC221192
0.6857	Remote Similarity	NPC222997
0.6857	Remote Similarity	NPC4962
0.6857	Remote Similarity	NPC153439
0.6842	Remote Similarity	NPC289344
0.6842	Remote Similarity	NPC317203
0.6818	Remote Similarity	NPC282440
0.6809	Remote Similarity	NPC287811
0.6809	Remote Similarity	NPC470410
0.6809	Remote Similarity	NPC470412
0.6809	Remote Similarity	NPC314084
0.6809	Remote Similarity	NPC262968
0.6757	Remote Similarity	NPC322892
0.6757	Remote Similarity	NPC286695
0.675	Remote Similarity	NPC326532
0.6744	Remote Similarity	NPC76051
0.6739	Remote Similarity	NPC250919
0.6667	Remote Similarity	NPC310746
0.6667	Remote Similarity	NPC249754
0.6667	Remote Similarity	NPC161366
0.6667	Remote Similarity	NPC281245
0.6596	Remote Similarity	NPC50457
0.6591	Remote Similarity	NPC469781
0.6585	Remote Similarity	NPC94368
0.6585	Remote Similarity	NPC3531
0.6571	Remote Similarity	NPC198118
0.6571	Remote Similarity	NPC295442
0.6571	Remote Similarity	NPC38859
0.6531	Remote Similarity	NPC72722
0.6531	Remote Similarity	NPC1813
0.6531	Remote Similarity	NPC39633
0.6531	Remote Similarity	NPC294548
0.6531	Remote Similarity	NPC36061
0.6531	Remote Similarity	NPC139545
0.6531	Remote Similarity	NPC139029
0.6531	Remote Similarity	NPC309606
0.65	Remote Similarity	NPC14608
0.65	Remote Similarity	NPC158179
0.6486	Remote Similarity	NPC268596
0.6486	Remote Similarity	NPC12904
0.6486	Remote Similarity	NPC49151
0.6486	Remote Similarity	NPC179831
0.6486	Remote Similarity	NPC225318
0.6486	Remote Similarity	NPC261991
0.6486	Remote Similarity	NPC149101
0.6486	Remote Similarity	NPC262505
0.6486	Remote Similarity	NPC16578
0.6486	Remote Similarity	NPC40965
0.6486	Remote Similarity	NPC76608
0.6486	Remote Similarity	NPC254713
0.6471	Remote Similarity	NPC79591
0.6458	Remote Similarity	NPC100096
0.6444	Remote Similarity	NPC308301
0.641	Remote Similarity	NPC155872
0.64	Remote Similarity	NPC290563
0.64	Remote Similarity	NPC281972
0.64	Remote Similarity	NPC88966
0.64	Remote Similarity	NPC424
0.64	Remote Similarity	NPC320588
0.64	Remote Similarity	NPC32467
0.64	Remote Similarity	NPC469937
0.64	Remote Similarity	NPC25417
0.64	Remote Similarity	NPC6095
0.64	Remote Similarity	NPC154245
0.64	Remote Similarity	NPC85813
0.64	Remote Similarity	NPC87394
0.64	Remote Similarity	NPC261831
0.64	Remote Similarity	NPC319589
0.64	Remote Similarity	NPC23155
0.64	Remote Similarity	NPC53463
0.64	Remote Similarity	NPC87564
0.6389	Remote Similarity	NPC248139
0.6389	Remote Similarity	NPC158107
0.6383	Remote Similarity	NPC476469
0.6327	Remote Similarity	NPC18357
0.6316	Remote Similarity	NPC147054
0.6275	Remote Similarity	NPC223677
0.6275	Remote Similarity	NPC200845
0.6275	Remote Similarity	NPC10316
0.6275	Remote Similarity	NPC228473
0.6275	Remote Similarity	NPC128061
0.6275	Remote Similarity	NPC28779
0.625	Remote Similarity	NPC301919
0.62	Remote Similarity	NPC70387
0.62	Remote Similarity	NPC71761
0.62	Remote Similarity	NPC321062
0.6176	Remote Similarity	NPC66624
0.6176	Remote Similarity	NPC28246
0.617	Remote Similarity	NPC13105
0.6154	Remote Similarity	NPC18951
0.6154	Remote Similarity	NPC477201
0.6154	Remote Similarity	NPC7814

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 NPC156630 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1784
0.1-0.2	5151
0.2-0.3	1552
0.3-0.4	466
0.4-0.5	134
0.5-0.6	30
0.6-0.7	22
0.7-0.8	5
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9143	High Similarity	NPD3206	Approved
0.8889	High Similarity	NPD9448	Phase 2
0.8889	High Similarity	NPD633	Phase 3
0.8421	Intermediate Similarity	NPD2270	Approved
0.8378	Intermediate Similarity	NPD9655	Approved
0.8205	Intermediate Similarity	NPD387	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD9449	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3199	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD2699	Approved
0.7619	Intermediate Similarity	NPD634	Phase 3
0.7297	Intermediate Similarity	NPD9447	Approved
0.7209	Intermediate Similarity	NPD9430	Approved
0.7209	Intermediate Similarity	NPD9431	Approved
0.6889	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD622	Approved
0.6809	Remote Similarity	NPD29	Approved
0.6809	Remote Similarity	NPD28	Approved
0.675	Remote Similarity	NPD9513	Phase 1
0.6667	Remote Similarity	NPD3186	Phase 1
0.6585	Remote Similarity	NPD77	Approved
0.6585	Remote Similarity	NPD9450	Approved
0.6531	Remote Similarity	NPD3172	Approved
0.6458	Remote Similarity	NPD9638	Phase 2
0.64	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3195	Phase 2
0.64	Remote Similarity	NPD615	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3728	Approved
0.64	Remote Similarity	NPD3730	Approved
0.64	Remote Similarity	NPD3194	Approved
0.64	Remote Similarity	NPD3196	Approved
0.64	Remote Similarity	NPD4266	Approved
0.6389	Remote Similarity	NPD62	Approved
0.625	Remote Similarity	NPD8616	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8615	Phase 2
0.6154	Remote Similarity	NPD8857	Approved
0.6087	Remote Similarity	NPD3174	Discontinued
0.6047	Remote Similarity	NPD9635	Discontinued
0.5833	Remote Similarity	NPD2266	Phase 2
0.5833	Remote Similarity	NPD8990	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD3198	Approved
0.5714	Remote Similarity	NPD3173	Approved
0.5652	Remote Similarity	NPD9019	Approved
0.5641	Remote Similarity	NPD1461	Approved
0.5641	Remote Similarity	NPD907	Approved
0.5641	Remote Similarity	NPD908	Approved
0.5614	Remote Similarity	NPD9676	Phase 3

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