NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	2.911
LogD:	2.689
LogS:	-2.77
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	4.094
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.513
MDCK Permeability:	3.277653377153911e-05
Pgp-inhibitor:	0.316
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.624

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.64
Plasma Protein Binding (PPB):	69.28083038330078%
Volume Distribution (VD):	1.006
Pgp-substrate:	34.832664489746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.129
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.795
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.315
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	11.141
Half-life (T1/2):	0.595

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.605
Drug-inuced Liver Injury (DILI):	0.752
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.101
Carcinogencity:	0.913
Eye Corrosion:	0.354
Eye Irritation:	0.375
Respiratory Toxicity:	0.861

Download Data

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

Natural Product: NPC296522

Natural Product ID:	NPC296522
*Common Name:**	KVWUOMNJFDNWQM-FRJFDASCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KVWUOMNJFDNWQM-FRJFDASCSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h6,9,11,13-14H,4-5,7-8H2,1-3H3/t9-,11+,13+,14-/m0/s1
SMILES:	CC(=O)CCC1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)[C@@H]2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594243
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0000502] Xanthanolides

*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
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17612	Xanthium sibiricum	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
IC50	3
Others	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	TC50	=	77.6	uM	PMID[508827]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[508827]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	=	6400.0	nM	PMID[508827]
NPT2	Others	Unspecified		Selectivity Index	=	12.1	n.a.	PMID[508827]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	35000.0	nM	PMID[508827]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	<	20.0	%	PMID[508827]

☑ 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 NPC296522 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	179
0.1-0.2	1348
0.2-0.3	8236
0.3-0.4	15910
0.4-0.5	8044
0.5-0.6	6332
0.6-0.7	2266
0.7-0.8	316
0.8-0.85	44
0.85-0.9	11
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC144511
0.9545	High Similarity	NPC472955
0.9143	High Similarity	NPC266159
0.9143	High Similarity	NPC472967
0.913	High Similarity	NPC472966
0.9014	High Similarity	NPC195785
0.9014	High Similarity	NPC15975
0.9	High Similarity	NPC226669
0.9	High Similarity	NPC193351
0.9	High Similarity	NPC138408
0.8986	High Similarity	NPC472956
0.8873	High Similarity	NPC472959
0.8824	High Similarity	NPC199557
0.875	High Similarity	NPC65603
0.8592	High Similarity	NPC469643
0.8592	High Similarity	NPC469641
0.8571	High Similarity	NPC129665
0.8533	High Similarity	NPC39411
0.8533	High Similarity	NPC470241
0.8533	High Similarity	NPC255580
0.8514	High Similarity	NPC182550
0.8514	High Similarity	NPC264227
0.8514	High Similarity	NPC63649
0.8514	High Similarity	NPC472965
0.8493	Intermediate Similarity	NPC476794
0.8493	Intermediate Similarity	NPC470240
0.8472	Intermediate Similarity	NPC155587
0.8472	Intermediate Similarity	NPC324762
0.84	Intermediate Similarity	NPC302426
0.8289	Intermediate Similarity	NPC281949
0.8289	Intermediate Similarity	NPC301477
0.8289	Intermediate Similarity	NPC25684
0.8286	Intermediate Similarity	NPC5714
0.8267	Intermediate Similarity	NPC470239
0.8267	Intermediate Similarity	NPC470244
0.8205	Intermediate Similarity	NPC165287
0.8182	Intermediate Similarity	NPC89555
0.8158	Intermediate Similarity	NPC74673
0.8158	Intermediate Similarity	NPC276356
0.8158	Intermediate Similarity	NPC69271
0.8133	Intermediate Similarity	NPC128276
0.8133	Intermediate Similarity	NPC35574
0.8133	Intermediate Similarity	NPC472960
0.8133	Intermediate Similarity	NPC299235
0.8108	Intermediate Similarity	NPC474527
0.8108	Intermediate Similarity	NPC471726
0.8108	Intermediate Similarity	NPC235906
0.8101	Intermediate Similarity	NPC78089
0.8077	Intermediate Similarity	NPC39588
0.8077	Intermediate Similarity	NPC318468
0.8056	Intermediate Similarity	NPC163003
0.8052	Intermediate Similarity	NPC475665
0.8052	Intermediate Similarity	NPC35089
0.8052	Intermediate Similarity	NPC10276
0.8026	Intermediate Similarity	NPC89128
0.8	Intermediate Similarity	NPC474760
0.8	Intermediate Similarity	NPC41780
0.8	Intermediate Similarity	NPC57744
0.8	Intermediate Similarity	NPC107787
0.8	Intermediate Similarity	NPC187568
0.7975	Intermediate Similarity	NPC472957
0.7975	Intermediate Similarity	NPC472958
0.7975	Intermediate Similarity	NPC115786
0.7945	Intermediate Similarity	NPC470237
0.7945	Intermediate Similarity	NPC58956
0.7945	Intermediate Similarity	NPC269206
0.7945	Intermediate Similarity	NPC295633
0.7917	Intermediate Similarity	NPC475310
0.7901	Intermediate Similarity	NPC237540
0.7875	Intermediate Similarity	NPC33570
0.7875	Intermediate Similarity	NPC161957
0.7875	Intermediate Similarity	NPC165162
0.7875	Intermediate Similarity	NPC21471
0.7857	Intermediate Similarity	NPC304665
0.7857	Intermediate Similarity	NPC154728
0.7857	Intermediate Similarity	NPC126899
0.7848	Intermediate Similarity	NPC215294
0.7838	Intermediate Similarity	NPC476355
0.7838	Intermediate Similarity	NPC140287
0.7821	Intermediate Similarity	NPC471325
0.7821	Intermediate Similarity	NPC207188
0.7792	Intermediate Similarity	NPC178277
0.7792	Intermediate Similarity	NPC617
0.7792	Intermediate Similarity	NPC469690
0.7778	Intermediate Similarity	NPC477448
0.7778	Intermediate Similarity	NPC477449
0.775	Intermediate Similarity	NPC156485
0.7733	Intermediate Similarity	NPC471491
0.7733	Intermediate Similarity	NPC475861
0.7722	Intermediate Similarity	NPC173609
0.7703	Intermediate Similarity	NPC107783
0.7703	Intermediate Similarity	NPC92909
0.7692	Intermediate Similarity	NPC223904
0.7662	Intermediate Similarity	NPC11796
0.7662	Intermediate Similarity	NPC218817
0.7654	Intermediate Similarity	NPC235792
0.7632	Intermediate Similarity	NPC123360
0.7632	Intermediate Similarity	NPC226242
0.7632	Intermediate Similarity	NPC41017
0.7625	Intermediate Similarity	NPC470948
0.76	Intermediate Similarity	NPC259599
0.76	Intermediate Similarity	NPC167049
0.76	Intermediate Similarity	NPC294434
0.76	Intermediate Similarity	NPC117746
0.76	Intermediate Similarity	NPC320537
0.76	Intermediate Similarity	NPC143979
0.76	Intermediate Similarity	NPC15499
0.76	Intermediate Similarity	NPC469691
0.7595	Intermediate Similarity	NPC141810
0.7595	Intermediate Similarity	NPC52861
0.7595	Intermediate Similarity	NPC42470
0.759	Intermediate Similarity	NPC190718
0.7564	Intermediate Similarity	NPC270126
0.7564	Intermediate Similarity	NPC469620
0.7561	Intermediate Similarity	NPC70422
0.7561	Intermediate Similarity	NPC104961
0.7561	Intermediate Similarity	NPC67493
0.7561	Intermediate Similarity	NPC70555
0.7532	Intermediate Similarity	NPC122264
0.7532	Intermediate Similarity	NPC97516
0.7532	Intermediate Similarity	NPC476028
0.7532	Intermediate Similarity	NPC208223
0.7532	Intermediate Similarity	NPC7563
0.7532	Intermediate Similarity	NPC171204
0.7532	Intermediate Similarity	NPC116177
0.7532	Intermediate Similarity	NPC320630
0.7532	Intermediate Similarity	NPC141789
0.7531	Intermediate Similarity	NPC139566
0.7531	Intermediate Similarity	NPC96259
0.7531	Intermediate Similarity	NPC100391
0.7531	Intermediate Similarity	NPC141193
0.7531	Intermediate Similarity	NPC295799
0.75	Intermediate Similarity	NPC170167
0.75	Intermediate Similarity	NPC216407
0.75	Intermediate Similarity	NPC268298
0.75	Intermediate Similarity	NPC244166
0.75	Intermediate Similarity	NPC469868
0.75	Intermediate Similarity	NPC469678
0.75	Intermediate Similarity	NPC475771
0.75	Intermediate Similarity	NPC178676
0.75	Intermediate Similarity	NPC469669
0.7468	Intermediate Similarity	NPC293418
0.7468	Intermediate Similarity	NPC304795
0.7468	Intermediate Similarity	NPC51507
0.7468	Intermediate Similarity	NPC73052
0.7468	Intermediate Similarity	NPC290508
0.7468	Intermediate Similarity	NPC6823
0.7468	Intermediate Similarity	NPC200446
0.7468	Intermediate Similarity	NPC195424
0.7467	Intermediate Similarity	NPC135703
0.7465	Intermediate Similarity	NPC474329
0.7465	Intermediate Similarity	NPC474304
0.7439	Intermediate Similarity	NPC52628
0.7439	Intermediate Similarity	NPC470223
0.7439	Intermediate Similarity	NPC110405
0.7439	Intermediate Similarity	NPC177932
0.7439	Intermediate Similarity	NPC125290
0.7436	Intermediate Similarity	NPC108816
0.7436	Intermediate Similarity	NPC471220
0.7436	Intermediate Similarity	NPC471465
0.7436	Intermediate Similarity	NPC196653
0.7436	Intermediate Similarity	NPC267231
0.7436	Intermediate Similarity	NPC474341
0.7436	Intermediate Similarity	NPC93763
0.7436	Intermediate Similarity	NPC469495
0.7412	Intermediate Similarity	NPC62815
0.7412	Intermediate Similarity	NPC129419
0.7412	Intermediate Similarity	NPC37607
0.7412	Intermediate Similarity	NPC301969
0.7412	Intermediate Similarity	NPC253144
0.7407	Intermediate Similarity	NPC474703
0.7407	Intermediate Similarity	NPC108045
0.7407	Intermediate Similarity	NPC475622
0.7407	Intermediate Similarity	NPC475947
0.7407	Intermediate Similarity	NPC272814
0.7407	Intermediate Similarity	NPC475989
0.7407	Intermediate Similarity	NPC193198
0.7403	Intermediate Similarity	NPC473223
0.7403	Intermediate Similarity	NPC279537
0.7403	Intermediate Similarity	NPC92489
0.7397	Intermediate Similarity	NPC470256
0.7397	Intermediate Similarity	NPC476614
0.7381	Intermediate Similarity	NPC215831
0.7381	Intermediate Similarity	NPC91248
0.7381	Intermediate Similarity	NPC474845
0.7381	Intermediate Similarity	NPC224652
0.7381	Intermediate Similarity	NPC28227
0.7368	Intermediate Similarity	NPC474551
0.7349	Intermediate Similarity	NPC279859
0.7349	Intermediate Similarity	NPC38576
0.7349	Intermediate Similarity	NPC6979
0.7344	Intermediate Similarity	NPC244452
0.7342	Intermediate Similarity	NPC209995
0.7342	Intermediate Similarity	NPC98557
0.7342	Intermediate Similarity	NPC167881
0.7333	Intermediate Similarity	NPC29328
0.7333	Intermediate Similarity	NPC288667
0.7333	Intermediate Similarity	NPC40327
0.7326	Intermediate Similarity	NPC123177
0.7326	Intermediate Similarity	NPC150978

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 NPC296522 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1992
0.2-0.3	4209
0.3-0.4	1890
0.4-0.5	521
0.5-0.6	279
0.6-0.7	66
0.7-0.8	20
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
0.7439	Intermediate Similarity	NPD1694	Approved
0.7375	Intermediate Similarity	NPD5369	Approved
0.7294	Intermediate Similarity	NPD1695	Approved
0.7284	Intermediate Similarity	NPD6435	Approved
0.7229	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4270	Approved
0.7073	Intermediate Similarity	NPD4269	Approved
0.7037	Intermediate Similarity	NPD5368	Approved
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5362	Discontinued
0.6988	Remote Similarity	NPD7154	Phase 3
0.6977	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6903	Approved
0.6941	Remote Similarity	NPD5786	Approved
0.6867	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6399	Phase 3
0.6835	Remote Similarity	NPD8039	Approved
0.6829	Remote Similarity	NPD4252	Approved
0.6824	Remote Similarity	NPD5363	Approved
0.6782	Remote Similarity	NPD6672	Approved
0.6782	Remote Similarity	NPD5737	Approved
0.6757	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5209	Approved
0.6629	Remote Similarity	NPD5207	Approved
0.6629	Remote Similarity	NPD5785	Approved
0.6628	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7900	Approved
0.6593	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD29	Approved
0.6567	Remote Similarity	NPD28	Approved
0.6552	Remote Similarity	NPD6098	Approved
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6101	Approved
0.6517	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3667	Approved
0.6452	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7331	Phase 2
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD4819	Approved
0.6413	Remote Similarity	NPD6001	Approved
0.6413	Remote Similarity	NPD7748	Approved
0.6413	Remote Similarity	NPD5282	Discontinued
0.6404	Remote Similarity	NPD5208	Approved
0.64	Remote Similarity	NPD3197	Phase 1
0.6395	Remote Similarity	NPD5332	Approved
0.6395	Remote Similarity	NPD5331	Approved
0.6386	Remote Similarity	NPD4271	Approved
0.6386	Remote Similarity	NPD4268	Approved
0.6383	Remote Similarity	NPD7902	Approved
0.6377	Remote Similarity	NPD3172	Approved
0.6374	Remote Similarity	NPD6411	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6364	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD6422	Discontinued
0.6353	Remote Similarity	NPD4790	Discontinued
0.6344	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD6904	Approved
0.6333	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD6080	Approved
0.6322	Remote Similarity	NPD3665	Phase 1
0.6322	Remote Similarity	NPD3668	Phase 3
0.6322	Remote Similarity	NPD3133	Approved
0.6322	Remote Similarity	NPD3666	Approved
0.6322	Remote Similarity	NPD4786	Approved
0.6316	Remote Similarity	NPD5696	Approved
0.6304	Remote Similarity	NPD5778	Approved
0.6304	Remote Similarity	NPD5779	Approved
0.6292	Remote Similarity	NPD4251	Approved
0.6292	Remote Similarity	NPD4250	Approved
0.6292	Remote Similarity	NPD3573	Approved
0.6286	Remote Similarity	NPD4266	Approved
0.6286	Remote Similarity	NPD3195	Phase 2
0.6286	Remote Similarity	NPD3194	Approved
0.6286	Remote Similarity	NPD3196	Approved
0.6264	Remote Similarity	NPD46	Approved
0.6264	Remote Similarity	NPD5692	Phase 3
0.6264	Remote Similarity	NPD6698	Approved
0.6263	Remote Similarity	NPD6008	Approved
0.6211	Remote Similarity	NPD6083	Phase 2
0.6211	Remote Similarity	NPD6084	Phase 2
0.62	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5694	Approved
0.6196	Remote Similarity	NPD6050	Approved
0.6196	Remote Similarity	NPD7983	Approved
0.6196	Remote Similarity	NPD5693	Phase 1
0.6196	Remote Similarity	NPD7515	Phase 2
0.618	Remote Similarity	NPD5279	Phase 3
0.6176	Remote Similarity	NPD6371	Approved
0.6163	Remote Similarity	NPD857	Phase 3
0.6154	Remote Similarity	NPD5370	Suspended
0.6119	Remote Similarity	NPD5343	Approved
0.6104	Remote Similarity	NPD7341	Phase 2
0.6087	Remote Similarity	NPD3673	Approved
0.6087	Remote Similarity	NPD3672	Approved
0.6081	Remote Similarity	NPD3198	Approved
0.6061	Remote Similarity	NPD3174	Discontinued
0.6026	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD8035	Phase 2
0.6022	Remote Similarity	NPD5281	Approved
0.6022	Remote Similarity	NPD5284	Approved
0.6022	Remote Similarity	NPD8034	Phase 2
0.6022	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4137	Phase 3
0.6	Remote Similarity	NPD1145	Discontinued
0.5979	Remote Similarity	NPD4225	Approved
0.5978	Remote Similarity	NPD5328	Approved
0.5957	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5739	Approved
0.5941	Remote Similarity	NPD6675	Approved
0.5941	Remote Similarity	NPD7128	Approved
0.5941	Remote Similarity	NPD6402	Approved
0.5938	Remote Similarity	NPD7839	Suspended
0.5926	Remote Similarity	NPD4747	Approved
0.5926	Remote Similarity	NPD4691	Approved
0.5922	Remote Similarity	NPD6372	Approved
0.5922	Remote Similarity	NPD6373	Approved
0.5909	Remote Similarity	NPD4221	Approved
0.5909	Remote Similarity	NPD2699	Approved
0.5909	Remote Similarity	NPD4223	Phase 3
0.59	Remote Similarity	NPD6052	Approved
0.5897	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4756	Discovery
0.5882	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD622	Approved
0.5882	Remote Similarity	NPD5697	Approved
0.5875	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD229	Approved
0.5862	Remote Similarity	NPD4695	Discontinued
0.5857	Remote Similarity	NPD6927	Phase 3
0.5854	Remote Similarity	NPD5276	Approved
0.5854	Remote Similarity	NPD5777	Approved
0.5851	Remote Similarity	NPD6079	Approved
0.5851	Remote Similarity	NPD7637	Suspended
0.5833	Remote Similarity	NPD5654	Approved
0.5833	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD9298	Approved
0.5825	Remote Similarity	NPD6011	Approved
0.5825	Remote Similarity	NPD6899	Approved
0.5825	Remote Similarity	NPD6881	Approved
0.5825	Remote Similarity	NPD7320	Approved
0.5821	Remote Similarity	NPD634	Phase 3
0.5816	Remote Similarity	NPD7638	Approved
0.5814	Remote Similarity	NPD3732	Approved
0.581	Remote Similarity	NPD6649	Approved
0.581	Remote Similarity	NPD6650	Approved
0.5806	Remote Similarity	NPD6051	Approved
0.5806	Remote Similarity	NPD4753	Phase 2
0.5797	Remote Similarity	NPD3173	Approved
0.5789	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4202	Approved
0.5778	Remote Similarity	NPD4197	Approved
0.5773	Remote Similarity	NPD4697	Phase 3
0.5769	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6014	Approved
0.5769	Remote Similarity	NPD6012	Approved
0.5769	Remote Similarity	NPD6013	Approved
0.5758	Remote Similarity	NPD7640	Approved
0.5758	Remote Similarity	NPD7639	Approved
0.5733	Remote Similarity	NPD287	Approved
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD5959	Approved
0.5714	Remote Similarity	NPD5329	Approved
0.5714	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD5733	Approved
0.5714	Remote Similarity	NPD4058	Approved
0.5714	Remote Similarity	NPD4687	Approved
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD368	Approved
0.5673	Remote Similarity	NPD6686	Approved
0.5672	Remote Similarity	NPD6097	Approved
0.5672	Remote Similarity	NPD6096	Approved
0.567	Remote Similarity	NPD1693	Approved
0.567	Remote Similarity	NPD5210	Approved
0.567	Remote Similarity	NPD4629	Approved
0.566	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.566	Remote Similarity	NPD8130	Phase 1
0.566	Remote Similarity	NPD6869	Approved
0.566	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6617	Approved
0.566	Remote Similarity	NPD6847	Approved
0.5652	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5205	Approved
0.5652	Remote Similarity	NPD4693	Phase 3
0.5652	Remote Similarity	NPD5690	Phase 2
0.5652	Remote Similarity	NPD4694	Approved
0.5652	Remote Similarity	NPD4689	Approved
0.5652	Remote Similarity	NPD4688	Approved
0.5652	Remote Similarity	NPD4138	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