NPASS Compound

Structure

CID140543 OpenBabel06191715502D 24 27 0 0 1 0 0 0 0 0999 V2000 -3.4149 -3.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3174 -2.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6401 -0.7774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7165 -3.7650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7671 -1.7230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6334 -0.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1170 -2.9850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4005 -2.3399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2004 -3.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7671 -2.6871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6334 -3.4671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2001 -1.7230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2004 -0.9430 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2001 -2.6871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6837 -2.2050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2580 -2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7165 -0.6451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2001 -1.3969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6477 -2.2050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2240 -1.8381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6840 -2.9850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1749 -2.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1170 -1.4251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 8 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 15 1 0 0 0 0 8 18 2 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 21 1 1 0 0 0 11 4 1 6 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 6 1 1 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 6 0 0 0 13 24 1 0 0 0 0 14 7 1 6 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 3 1 1 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.11
Volume:	316.712
LogP:	1.716
LogD:	1.662
LogS:	-3.231
# Rotatable Bonds:	2
TPSA:	98.5
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	6.026
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.314
MDCK Permeability:	4.6823875891277567e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.71
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	83.35687255859375%
Volume Distribution (VD):	0.761
Pgp-substrate:	20.445171356201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	5.114
Half-life (T1/2):	0.639

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.76
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.343
Rat Oral Acute Toxicity:	0.892
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.578
Carcinogencity:	0.574
Eye Corrosion:	0.01
Eye Irritation:	0.028
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC140543

Natural Product ID:	NPC140543
*Common Name:**	Scandenolide
IUPAC Name:	n.a.
Synonyms:	Scandenolide
Standard InCHIKey:	SLIMCFUYVZKJTC-WFTXNEMLSA-N
Standard InCHI:	InChI=1S/C17H18O7/c1-7-14-11-4-9(16(20)22-11)10(21-8(2)18)5-13-17(3,24-13)6-12(14)23-15(7)19/h4,10-14H,1,5-6H2,2-3H3/t10-,11-,12+,13-,14+,17+/m1/s1
SMILES:	C=C1[C@H]2[C@H]3C=C([C@@H](C[C@@H]4[C@](C)(C[C@@H]2OC1=O)O4)OC(=O)C)C(=O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL424997
PubChem CID:	44398226
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	barks	n.a.	n.a.	PMID[15620248]
NPO24708	Mikania micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19267453]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20430633]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499851]
NPO23998	Auxarthron reticulatum	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24900275]
NPO6403	Phlegmariurus squarrosus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32941036]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22408	Aconitum polyschistum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22408	Aconitum polyschistum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24950	Eupatorium aschenbornianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25399	Patrinia intermedia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25241	Cordyla africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23866	Anisocycla cymosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25313	Satureja douglasii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24242	Haminoea cymbalum	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25683	Columba livia	Species	Columbidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6403	Phlegmariurus squarrosus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25115	Psychotria calocarpa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24142	Cereus ocamponis	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22408	Aconitum polyschistum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24895	Parmelia springtonensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24662	Ulmus laevis	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23134	Artemisia kaschgarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20331	Aerva tomentosa	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23998	Auxarthron reticulatum	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1827	Morinda elliptica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25341	Sanango racemosum	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24708	Mikania micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24854	Beltrania rhombica	Species	Beltraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25602	Crotalaria barbata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24950	Eupatorium aschenbornianum	Species	Asteraceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	10.0	uM	PMID[519106]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-1.0	n.a.	PMID[519106]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	10.0	uM	PMID[519107]

☑ 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 NPC140543 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	253
0.1-0.2	1603
0.2-0.3	5785
0.3-0.4	11494
0.4-0.5	13389
0.5-0.6	6255
0.6-0.7	2872
0.7-0.8	887
0.8-0.85	91
0.85-0.9	50
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC476267
0.9551	High Similarity	NPC473316
0.9551	High Similarity	NPC473330
0.954	High Similarity	NPC166919
0.9432	High Similarity	NPC312042
0.9348	High Similarity	NPC208233
0.9341	High Similarity	NPC35498
0.931	High Similarity	NPC475703
0.9195	High Similarity	NPC50637
0.9121	High Similarity	NPC471147
0.9101	High Similarity	NPC151770
0.9043	High Similarity	NPC288876
0.9022	High Similarity	NPC475659
0.8947	High Similarity	NPC264477
0.8947	High Similarity	NPC477511
0.8936	High Similarity	NPC473326
0.8936	High Similarity	NPC279561
0.8925	High Similarity	NPC473859
0.8925	High Similarity	NPC17585
0.8925	High Similarity	NPC230800
0.8901	High Similarity	NPC20713
0.8876	High Similarity	NPC231889
0.8851	High Similarity	NPC272814
0.8804	High Similarity	NPC475838
0.8804	High Similarity	NPC125674
0.8804	High Similarity	NPC228451
0.8791	High Similarity	NPC475748
0.8764	High Similarity	NPC284902
0.871	High Similarity	NPC474247
0.8673	High Similarity	NPC477510
0.8673	High Similarity	NPC471143
0.8652	High Similarity	NPC319795
0.8652	High Similarity	NPC38468
0.8652	High Similarity	NPC50362
0.8646	High Similarity	NPC477512
0.8632	High Similarity	NPC471140
0.8621	High Similarity	NPC141810
0.8587	High Similarity	NPC251385
0.8587	High Similarity	NPC49342
0.8587	High Similarity	NPC62815
0.8571	High Similarity	NPC475902
0.8557	High Similarity	NPC474339
0.8557	High Similarity	NPC164598
0.8526	High Similarity	NPC476275
0.8526	High Similarity	NPC279621
0.8511	High Similarity	NPC303942
0.8511	High Similarity	NPC57405
0.85	High Similarity	NPC477513
0.8478	Intermediate Similarity	NPC295312
0.8469	Intermediate Similarity	NPC149371
0.8444	Intermediate Similarity	NPC474547
0.8444	Intermediate Similarity	NPC215364
0.8421	Intermediate Similarity	NPC471142
0.8421	Intermediate Similarity	NPC471141
0.8421	Intermediate Similarity	NPC14961
0.8421	Intermediate Similarity	NPC270013
0.8404	Intermediate Similarity	NPC212486
0.8391	Intermediate Similarity	NPC617
0.8387	Intermediate Similarity	NPC144133
0.8387	Intermediate Similarity	NPC469718
0.8387	Intermediate Similarity	NPC179394
0.8387	Intermediate Similarity	NPC329857
0.8387	Intermediate Similarity	NPC475855
0.837	Intermediate Similarity	NPC475906
0.837	Intermediate Similarity	NPC469653
0.837	Intermediate Similarity	NPC471047
0.837	Intermediate Similarity	NPC469631
0.837	Intermediate Similarity	NPC469628
0.8367	Intermediate Similarity	NPC201718
0.8367	Intermediate Similarity	NPC47880
0.8352	Intermediate Similarity	NPC204048
0.8351	Intermediate Similarity	NPC471144
0.8333	Intermediate Similarity	NPC470238
0.8333	Intermediate Similarity	NPC138647
0.8333	Intermediate Similarity	NPC476315
0.8316	Intermediate Similarity	NPC474035
0.8316	Intermediate Similarity	NPC81386
0.83	Intermediate Similarity	NPC474741
0.8283	Intermediate Similarity	NPC471148
0.828	Intermediate Similarity	NPC475971
0.8265	Intermediate Similarity	NPC475949
0.8261	Intermediate Similarity	NPC266957
0.8261	Intermediate Similarity	NPC160138
0.8261	Intermediate Similarity	NPC5130
0.8247	Intermediate Similarity	NPC471462
0.8229	Intermediate Similarity	NPC477922
0.8229	Intermediate Similarity	NPC474947
0.8222	Intermediate Similarity	NPC475947
0.8222	Intermediate Similarity	NPC170377
0.8222	Intermediate Similarity	NPC318468
0.8211	Intermediate Similarity	NPC165383
0.8211	Intermediate Similarity	NPC475912
0.8211	Intermediate Similarity	NPC476300
0.8211	Intermediate Similarity	NPC81419
0.8211	Intermediate Similarity	NPC179746
0.8191	Intermediate Similarity	NPC51004
0.8191	Intermediate Similarity	NPC473619
0.8191	Intermediate Similarity	NPC80875
0.8182	Intermediate Similarity	NPC270126
0.8172	Intermediate Similarity	NPC202672
0.8163	Intermediate Similarity	NPC474213
0.8161	Intermediate Similarity	NPC171204
0.8161	Intermediate Similarity	NPC476028
0.8161	Intermediate Similarity	NPC141789
0.8152	Intermediate Similarity	NPC475461
0.8152	Intermediate Similarity	NPC305475
0.8144	Intermediate Similarity	NPC299396
0.8144	Intermediate Similarity	NPC172998
0.8144	Intermediate Similarity	NPC301596
0.8144	Intermediate Similarity	NPC477921
0.8125	Intermediate Similarity	NPC477131
0.8125	Intermediate Similarity	NPC474338
0.8119	Intermediate Similarity	NPC100487
0.8111	Intermediate Similarity	NPC173609
0.8105	Intermediate Similarity	NPC300312
0.8105	Intermediate Similarity	NPC208886
0.8105	Intermediate Similarity	NPC12172
0.8105	Intermediate Similarity	NPC284185
0.8105	Intermediate Similarity	NPC111114
0.8105	Intermediate Similarity	NPC473321
0.8105	Intermediate Similarity	NPC261607
0.8105	Intermediate Similarity	NPC74103
0.8105	Intermediate Similarity	NPC70595
0.8105	Intermediate Similarity	NPC123177
0.8105	Intermediate Similarity	NPC184463
0.8105	Intermediate Similarity	NPC30515
0.8105	Intermediate Similarity	NPC150978
0.809	Intermediate Similarity	NPC281132
0.809	Intermediate Similarity	NPC474510
0.809	Intermediate Similarity	NPC223904
0.8085	Intermediate Similarity	NPC4986
0.8085	Intermediate Similarity	NPC307411
0.8085	Intermediate Similarity	NPC474032
0.8085	Intermediate Similarity	NPC78008
0.8081	Intermediate Similarity	NPC469551
0.8046	Intermediate Similarity	NPC123360
0.8046	Intermediate Similarity	NPC235906
0.8043	Intermediate Similarity	NPC255307
0.8043	Intermediate Similarity	NPC470755
0.8041	Intermediate Similarity	NPC234339
0.8041	Intermediate Similarity	NPC304886
0.8041	Intermediate Similarity	NPC36954
0.8041	Intermediate Similarity	NPC273197
0.8039	Intermediate Similarity	NPC243998
0.8039	Intermediate Similarity	NPC223450
0.8021	Intermediate Similarity	NPC135776
0.8021	Intermediate Similarity	NPC288240
0.8021	Intermediate Similarity	NPC162205
0.8021	Intermediate Similarity	NPC295204
0.8021	Intermediate Similarity	NPC273579
0.8021	Intermediate Similarity	NPC475302
0.802	Intermediate Similarity	NPC475945
0.802	Intermediate Similarity	NPC475871
0.8	Intermediate Similarity	NPC25684
0.8	Intermediate Similarity	NPC71533
0.8	Intermediate Similarity	NPC106510
0.8	Intermediate Similarity	NPC301477
0.8	Intermediate Similarity	NPC474742
0.8	Intermediate Similarity	NPC207188
0.8	Intermediate Similarity	NPC476270
0.8	Intermediate Similarity	NPC281949
0.8	Intermediate Similarity	NPC253144
0.7981	Intermediate Similarity	NPC38154
0.7979	Intermediate Similarity	NPC476805
0.7979	Intermediate Similarity	NPC475819
0.7979	Intermediate Similarity	NPC473715
0.7979	Intermediate Similarity	NPC224652
0.7957	Intermediate Similarity	NPC150755
0.7957	Intermediate Similarity	NPC107787
0.7957	Intermediate Similarity	NPC64153
0.7957	Intermediate Similarity	NPC122502
0.7955	Intermediate Similarity	NPC474760
0.7941	Intermediate Similarity	NPC203659
0.7938	Intermediate Similarity	NPC469632
0.7935	Intermediate Similarity	NPC114979
0.7935	Intermediate Similarity	NPC115786
0.7935	Intermediate Similarity	NPC191476
0.7935	Intermediate Similarity	NPC158756
0.7921	Intermediate Similarity	NPC474747
0.7917	Intermediate Similarity	NPC158061
0.7917	Intermediate Similarity	NPC133698
0.7879	Intermediate Similarity	NPC213947
0.7879	Intermediate Similarity	NPC170143
0.7879	Intermediate Similarity	NPC108475
0.7872	Intermediate Similarity	NPC471739
0.7872	Intermediate Similarity	NPC72513
0.7857	Intermediate Similarity	NPC67584
0.7849	Intermediate Similarity	NPC78089
0.7849	Intermediate Similarity	NPC235792
0.7843	Intermediate Similarity	NPC19239
0.7843	Intermediate Similarity	NPC474166
0.7843	Intermediate Similarity	NPC110989
0.7835	Intermediate Similarity	NPC475657
0.7826	Intermediate Similarity	NPC475989
0.7826	Intermediate Similarity	NPC474472
0.7826	Intermediate Similarity	NPC169575
0.7826	Intermediate Similarity	NPC474703
0.7826	Intermediate Similarity	NPC250315
0.7826	Intermediate Similarity	NPC40746
0.7826	Intermediate Similarity	NPC131669

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 NPC140543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	2181
0.2-0.3	3947
0.3-0.4	1901
0.4-0.5	584
0.5-0.6	255
0.6-0.7	42
0.7-0.8	5
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8652	High Similarity	NPD1733	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1695	Approved
0.7677	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6698	Approved
0.7449	Intermediate Similarity	NPD46	Approved
0.7248	Intermediate Similarity	NPD6371	Approved
0.71	Intermediate Similarity	NPD7838	Discovery
0.7059	Intermediate Similarity	NPD5282	Discontinued
0.7037	Intermediate Similarity	NPD6008	Approved
0.703	Intermediate Similarity	NPD7983	Approved
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6053	Discontinued
0.6804	Remote Similarity	NPD5209	Approved
0.6796	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD5778	Approved
0.6768	Remote Similarity	NPD1694	Approved
0.6765	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4225	Approved
0.6607	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD5363	Approved
0.6574	Remote Similarity	NPD6648	Approved
0.6535	Remote Similarity	NPD4249	Approved
0.6535	Remote Similarity	NPD5786	Approved
0.6514	Remote Similarity	NPD5344	Discontinued
0.6491	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD4251	Approved
0.6449	Remote Similarity	NPD7839	Suspended
0.6441	Remote Similarity	NPD7115	Discovery
0.6435	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7154	Phase 3
0.6393	Remote Similarity	NPD7642	Approved
0.6364	Remote Similarity	NPD8513	Phase 3
0.6364	Remote Similarity	NPD8516	Approved
0.6364	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD8515	Approved
0.6346	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6101	Approved
0.63	Remote Similarity	NPD4269	Approved
0.63	Remote Similarity	NPD6435	Approved
0.63	Remote Similarity	NPD4270	Approved
0.6275	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7319	Approved
0.626	Remote Similarity	NPD7829	Approved
0.626	Remote Similarity	NPD7830	Approved
0.6238	Remote Similarity	NPD5362	Discontinued
0.6226	Remote Similarity	NPD6411	Approved
0.6182	Remote Similarity	NPD7638	Approved
0.616	Remote Similarity	NPD7507	Approved
0.6126	Remote Similarity	NPD7640	Approved
0.6126	Remote Similarity	NPD7639	Approved
0.6111	Remote Similarity	NPD8074	Phase 3
0.61	Remote Similarity	NPD4819	Approved
0.61	Remote Similarity	NPD4252	Approved
0.61	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5368	Approved
0.61	Remote Similarity	NPD4822	Approved
0.61	Remote Similarity	NPD4820	Approved
0.61	Remote Similarity	NPD4821	Approved
0.6082	Remote Similarity	NPD8039	Approved
0.608	Remote Similarity	NPD7492	Approved
0.6061	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6616	Approved
0.6017	Remote Similarity	NPD2204	Approved
0.6016	Remote Similarity	NPD6319	Approved
0.6016	Remote Similarity	NPD6054	Approved
0.5984	Remote Similarity	NPD7078	Approved
0.5968	Remote Similarity	NPD6015	Approved
0.5968	Remote Similarity	NPD6016	Approved
0.5948	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD6903	Approved
0.5938	Remote Similarity	NPD7736	Approved
0.5926	Remote Similarity	NPD7637	Suspended
0.5926	Remote Similarity	NPD5693	Phase 1
0.592	Remote Similarity	NPD5988	Approved
0.592	Remote Similarity	NPD6370	Approved
0.5906	Remote Similarity	NPD8273	Phase 1
0.5906	Remote Similarity	NPD8451	Approved
0.5905	Remote Similarity	NPD5330	Approved
0.5905	Remote Similarity	NPD7521	Approved
0.5905	Remote Similarity	NPD6684	Approved
0.5905	Remote Similarity	NPD6409	Approved
0.5905	Remote Similarity	NPD7146	Approved
0.5905	Remote Similarity	NPD7334	Approved
0.59	Remote Similarity	NPD4271	Approved
0.59	Remote Similarity	NPD4268	Approved
0.5897	Remote Similarity	NPD7320	Approved
0.5897	Remote Similarity	NPD6899	Approved
0.5897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6881	Approved
0.5887	Remote Similarity	NPD6059	Approved
0.5882	Remote Similarity	NPD6649	Approved
0.5882	Remote Similarity	NPD6650	Approved
0.5872	Remote Similarity	NPD6399	Phase 3
0.5865	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7128	Approved
0.5862	Remote Similarity	NPD6402	Approved
0.5862	Remote Similarity	NPD6675	Approved
0.5862	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD8293	Discontinued
0.5859	Remote Similarity	NPD8448	Approved
0.5849	Remote Similarity	NPD3573	Approved
0.5847	Remote Similarity	NPD6372	Approved
0.5847	Remote Similarity	NPD6014	Approved
0.5847	Remote Similarity	NPD6013	Approved
0.5847	Remote Similarity	NPD6012	Approved
0.5847	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD5207	Approved
0.5825	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7900	Approved
0.5818	Remote Similarity	NPD6001	Approved
0.5818	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5701	Approved
0.5802	Remote Similarity	NPD7260	Phase 2
0.5798	Remote Similarity	NPD7290	Approved
0.5798	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD7102	Approved
0.5798	Remote Similarity	NPD2067	Discontinued
0.5794	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5737	Approved
0.5794	Remote Similarity	NPD6672	Approved
0.5785	Remote Similarity	NPD4632	Approved
0.5769	Remote Similarity	NPD5332	Approved
0.5769	Remote Similarity	NPD5331	Approved
0.5766	Remote Similarity	NPD5695	Phase 3
0.5763	Remote Similarity	NPD6011	Approved
0.5758	Remote Similarity	NPD6845	Suspended
0.5755	Remote Similarity	NPD6422	Discontinued
0.5752	Remote Similarity	NPD5696	Approved
0.575	Remote Similarity	NPD6869	Approved
0.575	Remote Similarity	NPD8130	Phase 1
0.575	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD6617	Approved
0.5745	Remote Similarity	NPD7331	Phase 2
0.5743	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5370	Suspended
0.5728	Remote Similarity	NPD4790	Discontinued
0.5726	Remote Similarity	NPD7641	Discontinued
0.5725	Remote Similarity	NPD8392	Approved
0.5725	Remote Similarity	NPD8390	Approved
0.5725	Remote Similarity	NPD8391	Approved
0.5714	Remote Similarity	NPD8444	Approved
0.5703	Remote Similarity	NPD8341	Approved
0.5703	Remote Similarity	NPD8340	Approved
0.5703	Remote Similarity	NPD8299	Approved
0.5703	Remote Similarity	NPD8342	Approved
0.5702	Remote Similarity	NPD6882	Approved
0.5702	Remote Similarity	NPD8297	Approved
0.5669	Remote Similarity	NPD8080	Discontinued
0.5667	Remote Similarity	NPD4634	Approved
0.5664	Remote Similarity	NPD6083	Phase 2
0.5664	Remote Similarity	NPD6084	Phase 2
0.5664	Remote Similarity	NPD7902	Approved
0.5645	Remote Similarity	NPD6009	Approved
0.5645	Remote Similarity	NPD7500	Approved
0.5645	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4756	Discovery
0.5638	Remote Similarity	NPD7341	Phase 2
0.5636	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7604	Phase 2
0.5625	Remote Similarity	NPD8328	Phase 3
0.562	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD5211	Phase 2
0.5603	Remote Similarity	NPD7632	Discontinued
0.56	Remote Similarity	NPD7327	Approved
0.56	Remote Similarity	NPD7328	Approved

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