NPASS Compound

Structure

NPC142882 OpenBabel07101719522D 38 44 0 0 1 0 0 0 0 0999 V2000 -0.9614 2.2469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0499 0.8996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1068 2.7612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6009 1.6684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9905 3.4560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5313 -0.2637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7339 0.3313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0906 -0.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6583 0.9553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4991 -0.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3194 1.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8739 -0.8593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2558 0.8730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1088 2.7140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1167 1.2590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7844 1.8146 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 0.8689 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1733 2.8797 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1592 1.8797 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0006 0.2439 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2039 1.5841 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2267 3.2020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3309 0.6306 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8744 0.7301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3707 2.4602 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3389 0.6306 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0391 1.7165 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3389 -0.5294 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3724 2.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0756 0.6240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0075 3.1525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0689 4.1573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7507 3.3852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3450 2.1687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8110 1.0807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3389 0.2439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6737 0.0506 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 15 2 0 0 0 0 2 15 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 16 1 0 0 0 0 12 28 1 0 0 0 0 13 17 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 14 31 1 0 0 0 0 15 26 1 0 0 0 0 16 3 1 1 0 0 0 16 19 1 0 0 0 0 17 30 1 1 0 0 0 18 5 1 6 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 20 30 1 0 0 0 0 21 29 1 0 0 0 0 21 30 1 0 0 0 0 22 29 1 0 0 0 0 22 32 2 0 0 0 0 23 26 1 0 0 0 0 23 36 1 0 0 0 0 24 27 1 0 0 0 0 24 35 1 0 0 0 0 25 27 1 0 0 0 0 25 29 1 0 0 0 0 25 33 1 0 0 0 0 26 37 1 0 0 0 0 27 35 1 0 0 0 0 28 36 1 0 0 0 0 28 37 1 0 0 0 0 28 38 1 0 0 0 0 29 34 1 0 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.3
Volume:	532.59
LogP:	4.105
LogD:	3.889
LogS:	-3.805
# Rotatable Bonds:	2
TPSA:	117.98
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	7.918
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.051
MDCK Permeability:	5.536370008485392e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.229
Plasma Protein Binding (PPB):	94.98248291015625%
Volume Distribution (VD):	1.477
Pgp-substrate:	2.5335066318511963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.44

ADMET: Excretion

Clearance (CL):	10.811
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.398
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.332
Carcinogencity:	0.519
Eye Corrosion:	0.018
Eye Irritation:	0.015
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC142882

Natural Product ID:	NPC142882
*Common Name:**	Wikstroelide E
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YTMZOVBDBJZQRD-RSRQXKISSA-N
Standard InCHI:	InChI=1S/C30H44O8/c1-15(2)26-13-17(4)30-20-23(26)36-28(37-26,38-30)12-10-8-6-7-9-11-16(3)19-18(5)22(32)29(34,21(19)30)25(33)27(14-31)24(20)35-27/h16-21,23-25,31,33-34H,1,6-14H2,2-5H3/t16-,17-,18+,19+,20-,21-,23-,24+,25-,26-,27+,28-,29-,30-/m1/s1
SMILES:	OC[C@]12O[C@H]1[C@H]1[C@H]3O[C@@]45O[C@]1([C@H]1[C@@]([C@@H]2O)(O)C(=O)[C@H]([C@@H]1[C@H](C)CCCCCCC5)C)[C@@H](C[C@@]3(O4)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2376812
PubChem CID:	73347308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*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
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	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
IC50	10

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	24040.0	nM	PMID[488858]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	19460.0	nM	PMID[488858]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	22110.0	nM	PMID[488858]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	15140.0	nM	PMID[488858]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	19260.0	nM	PMID[488858]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	29930.0	nM	PMID[488858]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	11370.0	nM	PMID[488858]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[488858]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	17060.0	nM	PMID[488858]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29030.0	nM	PMID[488858]

☑ 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 NPC142882 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	325
0.1-0.2	2203
0.2-0.3	6317
0.3-0.4	10196
0.4-0.5	11803
0.5-0.6	6904
0.6-0.7	4229
0.7-0.8	671
0.8-0.85	32
0.85-0.9	9
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9402	High Similarity	NPC476078
0.9402	High Similarity	NPC476091
0.9244	High Similarity	NPC473838
0.9244	High Similarity	NPC475389
0.9068	High Similarity	NPC217901
0.8992	High Similarity	NPC168849
0.8992	High Similarity	NPC475273
0.8966	High Similarity	NPC317635
0.8966	High Similarity	NPC329008
0.8843	High Similarity	NPC162495
0.877	High Similarity	NPC475314
0.877	High Similarity	NPC251564
0.877	High Similarity	NPC477189
0.877	High Similarity	NPC475606
0.8699	High Similarity	NPC474508
0.8699	High Similarity	NPC475139
0.8699	High Similarity	NPC180902
0.8699	High Similarity	NPC473485
0.856	High Similarity	NPC475154
0.856	High Similarity	NPC182266
0.856	High Similarity	NPC100017
0.856	High Similarity	NPC475500
0.856	High Similarity	NPC471137
0.856	High Similarity	NPC471136
0.856	High Similarity	NPC473548
0.856	High Similarity	NPC223356
0.8425	Intermediate Similarity	NPC68282
0.813	Intermediate Similarity	NPC473802
0.8125	Intermediate Similarity	NPC305085
0.8125	Intermediate Similarity	NPC84042
0.8065	Intermediate Similarity	NPC473709
0.8065	Intermediate Similarity	NPC473919
0.8033	Intermediate Similarity	NPC472004
0.8	Intermediate Similarity	NPC471939
0.7966	Intermediate Similarity	NPC471251
0.7966	Intermediate Similarity	NPC94650
0.7937	Intermediate Similarity	NPC471940
0.7907	Intermediate Similarity	NPC475487
0.7881	Intermediate Similarity	NPC124053
0.7874	Intermediate Similarity	NPC270109
0.7852	Intermediate Similarity	NPC471172
0.7846	Intermediate Similarity	NPC475376
0.7846	Intermediate Similarity	NPC471234
0.784	Intermediate Similarity	NPC471392
0.7833	Intermediate Similarity	NPC471248
0.7833	Intermediate Similarity	NPC471252
0.7823	Intermediate Similarity	NPC102822
0.7823	Intermediate Similarity	NPC477046
0.7815	Intermediate Similarity	NPC470311
0.7815	Intermediate Similarity	NPC157476
0.7812	Intermediate Similarity	NPC475371
0.7805	Intermediate Similarity	NPC9674
0.7805	Intermediate Similarity	NPC19028
0.7797	Intermediate Similarity	NPC471250
0.7797	Intermediate Similarity	NPC118721
0.7797	Intermediate Similarity	NPC252679
0.7797	Intermediate Similarity	NPC473570
0.7795	Intermediate Similarity	NPC470780
0.7794	Intermediate Similarity	NPC194854
0.7794	Intermediate Similarity	NPC48813
0.7787	Intermediate Similarity	NPC473304
0.7786	Intermediate Similarity	NPC256618
0.7786	Intermediate Similarity	NPC219058
0.7769	Intermediate Similarity	NPC88668
0.776	Intermediate Similarity	NPC222688
0.775	Intermediate Similarity	NPC474927
0.775	Intermediate Similarity	NPC471244
0.775	Intermediate Similarity	NPC471245
0.775	Intermediate Similarity	NPC473397
0.775	Intermediate Similarity	NPC473303
0.7742	Intermediate Similarity	NPC108072
0.7742	Intermediate Similarity	NPC143755
0.7737	Intermediate Similarity	NPC16729
0.7737	Intermediate Similarity	NPC475462
0.7734	Intermediate Similarity	NPC311534
0.7731	Intermediate Similarity	NPC130302
0.7717	Intermediate Similarity	NPC273962
0.7717	Intermediate Similarity	NPC222307
0.7712	Intermediate Similarity	NPC89860
0.7712	Intermediate Similarity	NPC55973
0.7712	Intermediate Similarity	NPC189663
0.7712	Intermediate Similarity	NPC208461
0.7712	Intermediate Similarity	NPC289702
0.7705	Intermediate Similarity	NPC88945
0.7704	Intermediate Similarity	NPC5153
0.7704	Intermediate Similarity	NPC48414
0.7699	Intermediate Similarity	NPC111187
0.7699	Intermediate Similarity	NPC190080
0.7698	Intermediate Similarity	NPC43252
0.7698	Intermediate Similarity	NPC135038
0.7698	Intermediate Similarity	NPC472399
0.7692	Intermediate Similarity	NPC28791
0.7692	Intermediate Similarity	NPC295366
0.7692	Intermediate Similarity	NPC471855
0.7692	Intermediate Similarity	NPC42206
0.7686	Intermediate Similarity	NPC102619
0.7686	Intermediate Similarity	NPC477126
0.768	Intermediate Similarity	NPC310511
0.7674	Intermediate Similarity	NPC231529
0.7674	Intermediate Similarity	NPC470851
0.7672	Intermediate Similarity	NPC473148
0.7667	Intermediate Similarity	NPC56025
0.7667	Intermediate Similarity	NPC122339
0.7667	Intermediate Similarity	NPC473062
0.7667	Intermediate Similarity	NPC29505
0.7667	Intermediate Similarity	NPC63244
0.7667	Intermediate Similarity	NPC213320
0.7661	Intermediate Similarity	NPC472667
0.7656	Intermediate Similarity	NPC146456
0.7656	Intermediate Similarity	NPC305496
0.7656	Intermediate Similarity	NPC287423
0.7656	Intermediate Similarity	NPC117702
0.7656	Intermediate Similarity	NPC42399
0.7656	Intermediate Similarity	NPC469757
0.7656	Intermediate Similarity	NPC471357
0.7652	Intermediate Similarity	NPC67296
0.7638	Intermediate Similarity	NPC469790
0.7632	Intermediate Similarity	NPC253995
0.7627	Intermediate Similarity	NPC471461
0.7627	Intermediate Similarity	NPC251824
0.7627	Intermediate Similarity	NPC86852
0.7627	Intermediate Similarity	NPC67745
0.7623	Intermediate Similarity	NPC17165
0.7623	Intermediate Similarity	NPC300051
0.7623	Intermediate Similarity	NPC178289
0.7619	Intermediate Similarity	NPC65858
0.7612	Intermediate Similarity	NPC290746
0.7612	Intermediate Similarity	NPC79250
0.7607	Intermediate Similarity	NPC13149
0.7603	Intermediate Similarity	NPC471933
0.76	Intermediate Similarity	NPC112038
0.76	Intermediate Similarity	NPC251226
0.76	Intermediate Similarity	NPC471406
0.7597	Intermediate Similarity	NPC470850
0.7597	Intermediate Similarity	NPC473620
0.7597	Intermediate Similarity	NPC236999
0.7597	Intermediate Similarity	NPC477490
0.7597	Intermediate Similarity	NPC188291
0.7597	Intermediate Similarity	NPC114306
0.7586	Intermediate Similarity	NPC154675
0.7586	Intermediate Similarity	NPC52585
0.7586	Intermediate Similarity	NPC68630
0.7586	Intermediate Similarity	NPC228049
0.7583	Intermediate Similarity	NPC137104
0.7583	Intermediate Similarity	NPC320383
0.7583	Intermediate Similarity	NPC99760
0.7583	Intermediate Similarity	NPC473324
0.7583	Intermediate Similarity	NPC474786
0.7583	Intermediate Similarity	NPC85391
0.7583	Intermediate Similarity	NPC471476
0.7583	Intermediate Similarity	NPC255655
0.7583	Intermediate Similarity	NPC471093
0.7581	Intermediate Similarity	NPC204552
0.7581	Intermediate Similarity	NPC188667
0.7578	Intermediate Similarity	NPC104427
0.7578	Intermediate Similarity	NPC174367
0.7578	Intermediate Similarity	NPC225049
0.7578	Intermediate Similarity	NPC47113
0.7563	Intermediate Similarity	NPC473517
0.7563	Intermediate Similarity	NPC112895
0.7563	Intermediate Similarity	NPC273155
0.7563	Intermediate Similarity	NPC218123
0.7563	Intermediate Similarity	NPC255082
0.7563	Intermediate Similarity	NPC231278
0.7561	Intermediate Similarity	NPC106228
0.7561	Intermediate Similarity	NPC138372
0.7559	Intermediate Similarity	NPC472078
0.7559	Intermediate Similarity	NPC472077
0.7559	Intermediate Similarity	NPC469352
0.7559	Intermediate Similarity	NPC267822
0.7557	Intermediate Similarity	NPC472769
0.7557	Intermediate Similarity	NPC473519
0.7557	Intermediate Similarity	NPC473805
0.7544	Intermediate Similarity	NPC263674
0.7544	Intermediate Similarity	NPC304445
0.7544	Intermediate Similarity	NPC58267
0.7544	Intermediate Similarity	NPC236580
0.7544	Intermediate Similarity	NPC261372
0.7542	Intermediate Similarity	NPC130511
0.7542	Intermediate Similarity	NPC4115
0.7542	Intermediate Similarity	NPC44004
0.7542	Intermediate Similarity	NPC307660
0.7541	Intermediate Similarity	NPC97002
0.7541	Intermediate Similarity	NPC94141
0.7541	Intermediate Similarity	NPC132668
0.7541	Intermediate Similarity	NPC285086
0.754	Intermediate Similarity	NPC471999
0.754	Intermediate Similarity	NPC472401
0.754	Intermediate Similarity	NPC159456
0.754	Intermediate Similarity	NPC472000
0.754	Intermediate Similarity	NPC4021
0.7538	Intermediate Similarity	NPC6108
0.7538	Intermediate Similarity	NPC469752
0.7538	Intermediate Similarity	NPC471407
0.7538	Intermediate Similarity	NPC175186
0.7538	Intermediate Similarity	NPC219085
0.7538	Intermediate Similarity	NPC104382
0.7538	Intermediate Similarity	NPC470880
0.7538	Intermediate Similarity	NPC17896
0.7538	Intermediate Similarity	NPC89514

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 NPC142882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	2593
0.2-0.3	3946
0.3-0.4	1452
0.4-0.5	445
0.5-0.6	262
0.6-0.7	107
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7712	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6059	Approved
0.76	Intermediate Similarity	NPD6054	Approved
0.7538	Intermediate Similarity	NPD7319	Approved
0.748	Intermediate Similarity	NPD6370	Approved
0.7402	Intermediate Similarity	NPD6016	Approved
0.7402	Intermediate Similarity	NPD6015	Approved
0.7364	Intermediate Similarity	NPD7492	Approved
0.7344	Intermediate Similarity	NPD5988	Approved
0.7308	Intermediate Similarity	NPD7507	Approved
0.7308	Intermediate Similarity	NPD6616	Approved
0.7252	Intermediate Similarity	NPD7078	Approved
0.7252	Intermediate Similarity	NPD8293	Discontinued
0.7203	Intermediate Similarity	NPD1700	Approved
0.7197	Intermediate Similarity	NPD7736	Approved
0.7132	Intermediate Similarity	NPD6921	Approved
0.712	Intermediate Similarity	NPD8133	Approved
0.7109	Intermediate Similarity	NPD7516	Approved
0.7068	Intermediate Similarity	NPD6033	Approved
0.7054	Intermediate Similarity	NPD6319	Approved
0.7049	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7327	Approved
0.7031	Intermediate Similarity	NPD7328	Approved
0.6905	Remote Similarity	NPD6882	Approved
0.6885	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8516	Approved
0.687	Remote Similarity	NPD8515	Approved
0.687	Remote Similarity	NPD8517	Approved
0.687	Remote Similarity	NPD8513	Phase 3
0.6829	Remote Similarity	NPD6008	Approved
0.6822	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7115	Discovery
0.6822	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD6373	Approved
0.68	Remote Similarity	NPD6372	Approved
0.6774	Remote Similarity	NPD6412	Phase 2
0.6772	Remote Similarity	NPD8297	Approved
0.6767	Remote Similarity	NPD8328	Phase 3
0.6746	Remote Similarity	NPD4634	Approved
0.6742	Remote Similarity	NPD8296	Approved
0.6742	Remote Similarity	NPD8380	Approved
0.6742	Remote Similarity	NPD8335	Approved
0.6742	Remote Similarity	NPD8033	Approved
0.6742	Remote Similarity	NPD8379	Approved
0.6742	Remote Similarity	NPD8378	Approved
0.672	Remote Similarity	NPD7320	Approved
0.6719	Remote Similarity	NPD4632	Approved
0.6694	Remote Similarity	NPD6675	Approved
0.6694	Remote Similarity	NPD7128	Approved
0.6694	Remote Similarity	NPD6402	Approved
0.6694	Remote Similarity	NPD5739	Approved
0.6693	Remote Similarity	NPD6649	Approved
0.6693	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6641	Remote Similarity	NPD6053	Discontinued
0.6618	Remote Similarity	NPD8074	Phase 3
0.6614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6371	Approved
0.6587	Remote Similarity	NPD6881	Approved
0.6587	Remote Similarity	NPD6899	Approved
0.6562	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4755	Approved
0.6519	Remote Similarity	NPD7604	Phase 2
0.6508	Remote Similarity	NPD5697	Approved
0.6508	Remote Similarity	NPD5701	Approved
0.6493	Remote Similarity	NPD8268	Approved
0.6493	Remote Similarity	NPD8267	Approved
0.6493	Remote Similarity	NPD8266	Approved
0.6493	Remote Similarity	NPD8269	Approved
0.6484	Remote Similarity	NPD7102	Approved
0.6484	Remote Similarity	NPD7290	Approved
0.6484	Remote Similarity	NPD6883	Approved
0.6457	Remote Similarity	NPD6686	Approved
0.6452	Remote Similarity	NPD5211	Phase 2
0.6434	Remote Similarity	NPD8130	Phase 1
0.6434	Remote Similarity	NPD6617	Approved
0.6434	Remote Similarity	NPD6869	Approved
0.6434	Remote Similarity	NPD6847	Approved
0.6423	Remote Similarity	NPD5286	Approved
0.6423	Remote Similarity	NPD5285	Approved
0.6423	Remote Similarity	NPD4700	Approved
0.6423	Remote Similarity	NPD4696	Approved
0.6406	Remote Similarity	NPD6012	Approved
0.6406	Remote Similarity	NPD6014	Approved
0.6406	Remote Similarity	NPD6013	Approved
0.6378	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5344	Discontinued
0.637	Remote Similarity	NPD7503	Approved
0.637	Remote Similarity	NPD5983	Phase 2
0.6357	Remote Similarity	NPD5956	Approved
0.6349	Remote Similarity	NPD5141	Approved
0.6328	Remote Similarity	NPD6011	Approved
0.632	Remote Similarity	NPD5226	Approved
0.632	Remote Similarity	NPD5224	Approved
0.632	Remote Similarity	NPD4633	Approved
0.632	Remote Similarity	NPD5225	Approved
0.6308	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6336	Discontinued
0.6303	Remote Similarity	NPD6698	Approved
0.6303	Remote Similarity	NPD46	Approved
0.6299	Remote Similarity	NPD4768	Approved
0.6299	Remote Similarity	NPD4767	Approved
0.6277	Remote Similarity	NPD6067	Discontinued
0.627	Remote Similarity	NPD5174	Approved
0.627	Remote Similarity	NPD5175	Approved
0.624	Remote Similarity	NPD5223	Approved
0.622	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1695	Approved
0.621	Remote Similarity	NPD4225	Approved
0.621	Remote Similarity	NPD7638	Approved
0.6202	Remote Similarity	NPD4730	Approved
0.6202	Remote Similarity	NPD4729	Approved
0.616	Remote Similarity	NPD7640	Approved
0.616	Remote Similarity	NPD7639	Approved
0.6148	Remote Similarity	NPD5282	Discontinued
0.6142	Remote Similarity	NPD4754	Approved
0.6131	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6084	Phase 2
0.6129	Remote Similarity	NPD6083	Phase 2
0.6119	Remote Similarity	NPD6274	Approved
0.6116	Remote Similarity	NPD8034	Phase 2
0.6116	Remote Similarity	NPD8035	Phase 2
0.6107	Remote Similarity	NPD5247	Approved
0.6107	Remote Similarity	NPD5248	Approved
0.6107	Remote Similarity	NPD5250	Approved
0.6107	Remote Similarity	NPD5251	Approved
0.6107	Remote Similarity	NPD5249	Phase 3
0.6103	Remote Similarity	NPD7100	Approved
0.6103	Remote Similarity	NPD7101	Approved
0.6098	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD5128	Approved
0.6066	Remote Similarity	NPD8171	Discontinued
0.6066	Remote Similarity	NPD6399	Phase 3
0.6048	Remote Similarity	NPD4697	Phase 3
0.6042	Remote Similarity	NPD8338	Approved
0.6042	Remote Similarity	NPD6845	Suspended
0.6032	Remote Similarity	NPD6648	Approved
0.6029	Remote Similarity	NPD6335	Approved
0.6014	Remote Similarity	NPD6908	Approved
0.6014	Remote Similarity	NPD6909	Approved
0.5988	Remote Similarity	NPD7799	Discontinued
0.5984	Remote Similarity	NPD7983	Approved
0.5972	Remote Similarity	NPD7260	Phase 2
0.5968	Remote Similarity	NPD5695	Phase 3
0.5968	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD6317	Approved
0.5952	Remote Similarity	NPD5696	Approved
0.595	Remote Similarity	NPD5328	Approved
0.595	Remote Similarity	NPD4753	Phase 2
0.594	Remote Similarity	NPD5217	Approved
0.594	Remote Similarity	NPD5215	Approved
0.594	Remote Similarity	NPD5216	Approved
0.5935	Remote Similarity	NPD5779	Approved
0.5935	Remote Similarity	NPD4202	Approved
0.5935	Remote Similarity	NPD5778	Approved
0.5929	Remote Similarity	NPD7642	Approved
0.592	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.592	Remote Similarity	NPD5222	Approved
0.592	Remote Similarity	NPD5221	Approved
0.5918	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7524	Approved
0.5912	Remote Similarity	NPD6314	Approved
0.5912	Remote Similarity	NPD6313	Approved
0.5902	Remote Similarity	NPD3168	Discontinued
0.5899	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD5173	Approved
0.5865	Remote Similarity	NPD5135	Approved
0.5865	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5169	Approved
0.5862	Remote Similarity	NPD6928	Phase 2
0.5859	Remote Similarity	NPD4159	Approved
0.5857	Remote Similarity	NPD8080	Discontinued
0.5854	Remote Similarity	NPD6079	Approved
0.585	Remote Similarity	NPD8415	Approved
0.5847	Remote Similarity	NPD4788	Approved
0.5845	Remote Similarity	NPD8451	Approved
0.584	Remote Similarity	NPD4629	Approved
0.584	Remote Similarity	NPD5210	Approved
0.5833	Remote Similarity	NPD5786	Approved
0.5827	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD5127	Approved
0.582	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6101	Approved
0.5816	Remote Similarity	NPD7829	Approved
0.5816	Remote Similarity	NPD7830	Approved
0.5814	Remote Similarity	NPD7632	Discontinued
0.5812	Remote Similarity	NPD5369	Approved
0.5805	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD8448	Approved
0.5798	Remote Similarity	NPD4786	Approved
0.5766	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD8337	Approved
0.5764	Remote Similarity	NPD8336	Approved
0.5763	Remote Similarity	NPD6435	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