NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	562.21
Volume:	531.169
LogP:	2.115
LogD:	0.961
LogS:	-3.954
# Rotatable Bonds:	3
TPSA:	182.33
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	6.135
Fsp3:	0.714
Lipinski Rule-of-5:	Rejected
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:	-5.583
MDCK Permeability:	4.894042285741307e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.431
20% Bioavailability (F20%):	0.915
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.223
Plasma Protein Binding (PPB):	56.16861343383789%
Volume Distribution (VD):	0.593
Pgp-substrate:	34.05906295776367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	6.855
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.611
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.839
Maximum Recommended Daily Dose:	0.771
Skin Sensitization:	0.191
Carcinogencity:	0.236
Eye Corrosion:	0.019
Eye Irritation:	0.08
Respiratory Toxicity:	0.842

Download Data

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

Natural Product: NPC476855

Natural Product ID:	NPC476855
*Common Name:**	[(1R,2R,4S,7R,8S,10S,11R,12R,13S,18R)-10-hydroxy-7-(2-hydroxy-5-oxo-2H-furan-4-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icosan-13-yl] acetate
IUPAC Name:	[(1R,2R,4S,7R,8S,10S,11R,12R,13S,18R)-10-hydroxy-7-(2-hydroxy-5-oxo-2H-furan-4-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icosan-13-yl] acetate
Synonyms:
Standard InCHIKey:	GDCYPRWXUUCAKK-UVVLWALHSA-N
Standard InCHI:	InChI=1S/C28H34O12/c1-11(29)36-16-9-18(33)39-24(2,3)14-8-15(31)27(6)19(26(14,16)5)13(30)10-25(4)20(12-7-17(32)37-22(12)34)38-23(35)21-28(25,27)40-21/h7,13-14,16-17,19-21,30,32H,8-10H2,1-6H3/t13-,14-,16-,17?,19+,20-,21+,25-,26+,27+,28+/m0/s1
SMILES:	CC(=O)O[C@H]1CC(=O)OC([C@H]2[C@]1([C@H]3[C@H](C[C@]4([C@@H](OC(=O)[C@@H]5[C@@]4([C@@]3(C(=O)C2)C)O5)C6=CC(OC6=O)O)C)O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90670772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO33678	Clausena emarginata	Species	Rutaceae	Eukaryota	stems	Xishuangbanna, Yunnan Province, China	2010-AUG	PMID[24593150]

☑ 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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT1820	Cell Line	NCI-H1650	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT2	Others	Unspecified		IC50	>	10000	nM	PMID[24593150]

☑ 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 NPC476855 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	314
0.1-0.2	1811
0.2-0.3	4962
0.3-0.4	7935
0.4-0.5	11945
0.5-0.6	8840
0.6-0.7	5133
0.7-0.8	1671
0.8-0.85	79
0.85-0.9	0
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC476854
0.9832	High Similarity	NPC476859
0.9669	High Similarity	NPC476862
0.9669	High Similarity	NPC476852
0.9669	High Similarity	NPC476863
0.9587	High Similarity	NPC476851
0.864	High Similarity	NPC470922
0.8516	High Similarity	NPC472770
0.8492	Intermediate Similarity	NPC476729
0.8485	Intermediate Similarity	NPC295885
0.8485	Intermediate Similarity	NPC140045
0.8438	Intermediate Similarity	NPC473620
0.8425	Intermediate Similarity	NPC222307
0.8413	Intermediate Similarity	NPC472768
0.8413	Intermediate Similarity	NPC67251
0.8413	Intermediate Similarity	NPC265557
0.8413	Intermediate Similarity	NPC18945
0.8413	Intermediate Similarity	NPC91693
0.8413	Intermediate Similarity	NPC105926
0.8409	Intermediate Similarity	NPC471089
0.8409	Intermediate Similarity	NPC251998
0.8409	Intermediate Similarity	NPC141215
0.8409	Intermediate Similarity	NPC190065
0.84	Intermediate Similarity	NPC470779
0.8397	Intermediate Similarity	NPC471234
0.8387	Intermediate Similarity	NPC268958
0.8385	Intermediate Similarity	NPC472769
0.8374	Intermediate Similarity	NPC474483
0.8359	Intermediate Similarity	NPC42399
0.8359	Intermediate Similarity	NPC298841
0.8346	Intermediate Similarity	NPC596
0.8346	Intermediate Similarity	NPC24651
0.8333	Intermediate Similarity	NPC312833
0.8333	Intermediate Similarity	NPC262813
0.8321	Intermediate Similarity	NPC168879
0.832	Intermediate Similarity	NPC48692
0.832	Intermediate Similarity	NPC107338
0.832	Intermediate Similarity	NPC109607
0.8306	Intermediate Similarity	NPC240509
0.8295	Intermediate Similarity	NPC270109
0.8293	Intermediate Similarity	NPC213084
0.8293	Intermediate Similarity	NPC190185
0.8293	Intermediate Similarity	NPC471816
0.8281	Intermediate Similarity	NPC225049
0.8279	Intermediate Similarity	NPC159333
0.8271	Intermediate Similarity	NPC243014
0.8268	Intermediate Similarity	NPC472399
0.8254	Intermediate Similarity	NPC477046
0.8254	Intermediate Similarity	NPC102822
0.8244	Intermediate Similarity	NPC478154
0.8244	Intermediate Similarity	NPC102316
0.8244	Intermediate Similarity	NPC231240
0.824	Intermediate Similarity	NPC476529
0.824	Intermediate Similarity	NPC475775
0.8231	Intermediate Similarity	NPC477196
0.8231	Intermediate Similarity	NPC104382
0.8231	Intermediate Similarity	NPC175186
0.8217	Intermediate Similarity	NPC470780
0.8217	Intermediate Similarity	NPC287423
0.8211	Intermediate Similarity	NPC299849
0.8197	Intermediate Similarity	NPC317687
0.8182	Intermediate Similarity	NPC478151
0.8182	Intermediate Similarity	NPC316915
0.8175	Intermediate Similarity	NPC112038
0.8175	Intermediate Similarity	NPC476150
0.8175	Intermediate Similarity	NPC476127
0.8168	Intermediate Similarity	NPC25998
0.8168	Intermediate Similarity	NPC478155
0.8168	Intermediate Similarity	NPC471170
0.8168	Intermediate Similarity	NPC477197
0.816	Intermediate Similarity	NPC234522
0.816	Intermediate Similarity	NPC297179
0.816	Intermediate Similarity	NPC251310
0.8154	Intermediate Similarity	NPC477192
0.8154	Intermediate Similarity	NPC477194
0.8154	Intermediate Similarity	NPC477193
0.8154	Intermediate Similarity	NPC311534
0.8154	Intermediate Similarity	NPC477191
0.8145	Intermediate Similarity	NPC270478
0.813	Intermediate Similarity	NPC94509
0.813	Intermediate Similarity	NPC264153
0.8125	Intermediate Similarity	NPC120724
0.8125	Intermediate Similarity	NPC469789
0.8115	Intermediate Similarity	NPC317107
0.811	Intermediate Similarity	NPC472401
0.8106	Intermediate Similarity	NPC100390
0.8106	Intermediate Similarity	NPC33378
0.8106	Intermediate Similarity	NPC6274
0.8106	Intermediate Similarity	NPC476776
0.8106	Intermediate Similarity	NPC477195
0.8106	Intermediate Similarity	NPC254614
0.8106	Intermediate Similarity	NPC254146
0.8106	Intermediate Similarity	NPC478152
0.8106	Intermediate Similarity	NPC476193
0.8106	Intermediate Similarity	NPC471855
0.8106	Intermediate Similarity	NPC478153
0.8106	Intermediate Similarity	NPC478150
0.8106	Intermediate Similarity	NPC475139
0.8106	Intermediate Similarity	NPC180902
0.8095	Intermediate Similarity	NPC472933
0.8092	Intermediate Similarity	NPC280029
0.8092	Intermediate Similarity	NPC470518
0.8092	Intermediate Similarity	NPC1314
0.8092	Intermediate Similarity	NPC252657
0.8092	Intermediate Similarity	NPC273878
0.8092	Intermediate Similarity	NPC473593
0.8092	Intermediate Similarity	NPC244296
0.8092	Intermediate Similarity	NPC82380
0.8092	Intermediate Similarity	NPC477077
0.8092	Intermediate Similarity	NPC9470
0.8092	Intermediate Similarity	NPC115656
0.8092	Intermediate Similarity	NPC472267
0.8092	Intermediate Similarity	NPC477079
0.8092	Intermediate Similarity	NPC88311
0.8092	Intermediate Similarity	NPC265841
0.8092	Intermediate Similarity	NPC269484
0.8092	Intermediate Similarity	NPC477076
0.8092	Intermediate Similarity	NPC107536
0.8092	Intermediate Similarity	NPC470913
0.8092	Intermediate Similarity	NPC97918
0.8092	Intermediate Similarity	NPC11577
0.8092	Intermediate Similarity	NPC305793
0.8092	Intermediate Similarity	NPC141600
0.8092	Intermediate Similarity	NPC47995
0.8092	Intermediate Similarity	NPC252289
0.808	Intermediate Similarity	NPC13713
0.808	Intermediate Similarity	NPC473968
0.808	Intermediate Similarity	NPC470778
0.808	Intermediate Similarity	NPC146432
0.8077	Intermediate Similarity	NPC146456
0.8077	Intermediate Similarity	NPC469757
0.8077	Intermediate Similarity	NPC476008
0.8077	Intermediate Similarity	NPC117702
0.8077	Intermediate Similarity	NPC471357
0.8065	Intermediate Similarity	NPC181145
0.8062	Intermediate Similarity	NPC473709
0.8062	Intermediate Similarity	NPC473919
0.806	Intermediate Similarity	NPC171619
0.8049	Intermediate Similarity	NPC269530
0.8047	Intermediate Similarity	NPC23786
0.8047	Intermediate Similarity	NPC19464
0.8047	Intermediate Similarity	NPC471965
0.8047	Intermediate Similarity	NPC470265
0.8045	Intermediate Similarity	NPC476779
0.8045	Intermediate Similarity	NPC88668
0.8033	Intermediate Similarity	NPC476766
0.8031	Intermediate Similarity	NPC471128
0.8031	Intermediate Similarity	NPC157252
0.8031	Intermediate Similarity	NPC145182
0.8031	Intermediate Similarity	NPC471126
0.803	Intermediate Similarity	NPC173435
0.803	Intermediate Similarity	NPC478064
0.803	Intermediate Similarity	NPC134914
0.803	Intermediate Similarity	NPC329993
0.803	Intermediate Similarity	NPC264566
0.803	Intermediate Similarity	NPC271610
0.803	Intermediate Similarity	NPC476780
0.803	Intermediate Similarity	NPC301639
0.803	Intermediate Similarity	NPC476774
0.803	Intermediate Similarity	NPC476074
0.803	Intermediate Similarity	NPC478065
0.803	Intermediate Similarity	NPC475377
0.803	Intermediate Similarity	NPC172374
0.803	Intermediate Similarity	NPC475167
0.803	Intermediate Similarity	NPC45346
0.803	Intermediate Similarity	NPC476775
0.803	Intermediate Similarity	NPC262796
0.8017	Intermediate Similarity	NPC177524
0.8017	Intermediate Similarity	NPC476765
0.8017	Intermediate Similarity	NPC219900
0.8017	Intermediate Similarity	NPC392
0.8017	Intermediate Similarity	NPC322903
0.8016	Intermediate Similarity	NPC188667
0.8016	Intermediate Similarity	NPC17772
0.8016	Intermediate Similarity	NPC470776
0.8016	Intermediate Similarity	NPC204552
0.8015	Intermediate Similarity	NPC475636
0.8015	Intermediate Similarity	NPC329923
0.8015	Intermediate Similarity	NPC470475
0.8015	Intermediate Similarity	NPC295220
0.8015	Intermediate Similarity	NPC477075
0.8015	Intermediate Similarity	NPC475281
0.8015	Intermediate Similarity	NPC236999
0.8015	Intermediate Similarity	NPC477078
0.8015	Intermediate Similarity	NPC188291
0.8015	Intermediate Similarity	NPC470476
0.8	Intermediate Similarity	NPC474046
0.8	Intermediate Similarity	NPC259306
0.8	Intermediate Similarity	NPC134869
0.8	Intermediate Similarity	NPC477745
0.8	Intermediate Similarity	NPC235539
0.8	Intermediate Similarity	NPC89929
0.8	Intermediate Similarity	NPC152199
0.8	Intermediate Similarity	NPC470628
0.8	Intermediate Similarity	NPC285091
0.8	Intermediate Similarity	NPC293112
0.8	Intermediate Similarity	NPC217901
0.7985	Intermediate Similarity	NPC100017
0.7985	Intermediate Similarity	NPC182266
0.7985	Intermediate Similarity	NPC475500

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 NPC476855 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	2044
0.2-0.3	3798
0.3-0.4	1952
0.4-0.5	652
0.5-0.6	258
0.6-0.7	141
0.7-0.8	28
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
0.8017	Intermediate Similarity	NPD6686	Approved
0.7984	Intermediate Similarity	NPD8328	Phase 3
0.7955	Intermediate Similarity	NPD7319	Approved
0.7863	Intermediate Similarity	NPD7507	Approved
0.7769	Intermediate Similarity	NPD6370	Approved
0.7744	Intermediate Similarity	NPD7736	Approved
0.7724	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD8293	Discontinued
0.7656	Intermediate Similarity	NPD7115	Discovery
0.7652	Intermediate Similarity	NPD7492	Approved
0.7615	Intermediate Similarity	NPD6054	Approved
0.7615	Intermediate Similarity	NPD6319	Approved
0.76	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6616	Approved
0.7537	Intermediate Similarity	NPD7078	Approved
0.752	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6059	Approved
0.748	Intermediate Similarity	NPD8297	Approved
0.748	Intermediate Similarity	NPD6882	Approved
0.7462	Intermediate Similarity	NPD7328	Approved
0.7462	Intermediate Similarity	NPD7327	Approved
0.7424	Intermediate Similarity	NPD6016	Approved
0.7424	Intermediate Similarity	NPD6015	Approved
0.7405	Intermediate Similarity	NPD7516	Approved
0.7402	Intermediate Similarity	NPD6650	Approved
0.7402	Intermediate Similarity	NPD6649	Approved
0.7385	Intermediate Similarity	NPD6009	Approved
0.7381	Intermediate Similarity	NPD6373	Approved
0.7381	Intermediate Similarity	NPD6372	Approved
0.7368	Intermediate Similarity	NPD5988	Approved
0.736	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6881	Approved
0.7302	Intermediate Similarity	NPD6899	Approved
0.7293	Intermediate Similarity	NPD8516	Approved
0.7293	Intermediate Similarity	NPD8513	Phase 3
0.7293	Intermediate Similarity	NPD8517	Approved
0.7293	Intermediate Similarity	NPD8515	Approved
0.728	Intermediate Similarity	NPD6402	Approved
0.728	Intermediate Similarity	NPD6675	Approved
0.728	Intermediate Similarity	NPD5739	Approved
0.728	Intermediate Similarity	NPD7128	Approved
0.7222	Intermediate Similarity	NPD5697	Approved
0.7218	Intermediate Similarity	NPD8377	Approved
0.7218	Intermediate Similarity	NPD8294	Approved
0.7213	Intermediate Similarity	NPD4225	Approved
0.7188	Intermediate Similarity	NPD7290	Approved
0.7188	Intermediate Similarity	NPD6883	Approved
0.7188	Intermediate Similarity	NPD7102	Approved
0.7185	Intermediate Similarity	NPD7604	Phase 2
0.7165	Intermediate Similarity	NPD7320	Approved
0.7164	Intermediate Similarity	NPD6921	Approved
0.7164	Intermediate Similarity	NPD8033	Approved
0.7164	Intermediate Similarity	NPD8296	Approved
0.7164	Intermediate Similarity	NPD8380	Approved
0.7164	Intermediate Similarity	NPD8379	Approved
0.7164	Intermediate Similarity	NPD8335	Approved
0.7164	Intermediate Similarity	NPD8378	Approved
0.7154	Intermediate Similarity	NPD7640	Approved
0.7154	Intermediate Similarity	NPD7639	Approved
0.7154	Intermediate Similarity	NPD4632	Approved
0.7132	Intermediate Similarity	NPD6617	Approved
0.7132	Intermediate Similarity	NPD6847	Approved
0.7132	Intermediate Similarity	NPD8130	Phase 1
0.7132	Intermediate Similarity	NPD6869	Approved
0.7109	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6014	Approved
0.7109	Intermediate Similarity	NPD6013	Approved
0.7109	Intermediate Similarity	NPD6012	Approved
0.7087	Intermediate Similarity	NPD5701	Approved
0.7087	Intermediate Similarity	NPD6412	Phase 2
0.7073	Intermediate Similarity	NPD7638	Approved
0.7054	Intermediate Similarity	NPD6371	Approved
0.7037	Intermediate Similarity	NPD7503	Approved
0.7037	Intermediate Similarity	NPD5983	Phase 2
0.7031	Intermediate Similarity	NPD6011	Approved
0.7023	Intermediate Similarity	NPD8133	Approved
0.6978	Remote Similarity	NPD6033	Approved
0.6957	Remote Similarity	NPD6336	Discontinued
0.695	Remote Similarity	NPD7260	Phase 2
0.6923	Remote Similarity	NPD4634	Approved
0.6905	Remote Similarity	NPD5211	Phase 2
0.6875	Remote Similarity	NPD6008	Approved
0.687	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5344	Discontinued
0.6822	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5696	Approved
0.6797	Remote Similarity	NPD5141	Approved
0.6791	Remote Similarity	NPD6274	Approved
0.6786	Remote Similarity	NPD8074	Phase 3
0.6777	Remote Similarity	NPD46	Approved
0.6777	Remote Similarity	NPD6698	Approved
0.6765	Remote Similarity	NPD7101	Approved
0.6765	Remote Similarity	NPD7100	Approved
0.6746	Remote Similarity	NPD5285	Approved
0.6746	Remote Similarity	NPD5286	Approved
0.6746	Remote Similarity	NPD4696	Approved
0.6742	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4755	Approved
0.672	Remote Similarity	NPD6083	Phase 2
0.672	Remote Similarity	NPD6084	Phase 2
0.6712	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6053	Discontinued
0.6691	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6845	Suspended
0.6641	Remote Similarity	NPD7632	Discontinued
0.6641	Remote Similarity	NPD5224	Approved
0.6641	Remote Similarity	NPD4633	Approved
0.6641	Remote Similarity	NPD5226	Approved
0.6641	Remote Similarity	NPD5225	Approved
0.6618	Remote Similarity	NPD6317	Approved
0.6614	Remote Similarity	NPD4700	Approved
0.6614	Remote Similarity	NPD6648	Approved
0.6589	Remote Similarity	NPD5175	Approved
0.6589	Remote Similarity	NPD5174	Approved
0.6587	Remote Similarity	NPD7902	Approved
0.6571	Remote Similarity	NPD7642	Approved
0.6569	Remote Similarity	NPD6313	Approved
0.6569	Remote Similarity	NPD6314	Approved
0.6562	Remote Similarity	NPD5223	Approved
0.656	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6909	Approved
0.6547	Remote Similarity	NPD6908	Approved
0.6544	Remote Similarity	NPD6868	Approved
0.6535	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4730	Approved
0.6515	Remote Similarity	NPD4729	Approved
0.6508	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5222	Approved
0.6508	Remote Similarity	NPD5221	Approved
0.6508	Remote Similarity	NPD4697	Phase 3
0.6489	Remote Similarity	NPD4767	Approved
0.6489	Remote Similarity	NPD4768	Approved
0.648	Remote Similarity	NPD7748	Approved
0.6457	Remote Similarity	NPD5173	Approved
0.6454	Remote Similarity	NPD6067	Discontinued
0.6454	Remote Similarity	NPD7829	Approved
0.6454	Remote Similarity	NPD7830	Approved
0.6452	Remote Similarity	NPD7515	Phase 2
0.6452	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD7799	Discontinued
0.6429	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD4629	Approved
0.6423	Remote Similarity	NPD5328	Approved
0.6419	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5251	Approved
0.6418	Remote Similarity	NPD5248	Approved
0.6418	Remote Similarity	NPD5249	Phase 3
0.6418	Remote Similarity	NPD5247	Approved
0.6418	Remote Similarity	NPD5250	Approved
0.6414	Remote Similarity	NPD5956	Approved
0.64	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD5778	Approved
0.64	Remote Similarity	NPD5779	Approved
0.6393	Remote Similarity	NPD3573	Approved
0.6391	Remote Similarity	NPD5128	Approved
0.6387	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8080	Discontinued
0.6349	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5282	Discontinued
0.6349	Remote Similarity	NPD7900	Approved
0.6341	Remote Similarity	NPD6672	Approved
0.6341	Remote Similarity	NPD5737	Approved
0.6336	Remote Similarity	NPD4754	Approved
0.6333	Remote Similarity	NPD6334	Approved
0.6333	Remote Similarity	NPD6333	Approved
0.6327	Remote Similarity	NPD8338	Approved
0.632	Remote Similarity	NPD7983	Approved
0.632	Remote Similarity	NPD6411	Approved
0.632	Remote Similarity	NPD5693	Phase 1
0.6311	Remote Similarity	NPD3618	Phase 1
0.6301	Remote Similarity	NPD6914	Discontinued
0.6276	Remote Similarity	NPD8337	Approved
0.6276	Remote Similarity	NPD8336	Approved
0.625	Remote Similarity	NPD5217	Approved
0.625	Remote Similarity	NPD5215	Approved
0.625	Remote Similarity	NPD5216	Approved
0.6242	Remote Similarity	NPD8415	Approved
0.624	Remote Similarity	NPD7838	Discovery
0.624	Remote Similarity	NPD5785	Approved
0.623	Remote Similarity	NPD1694	Approved
0.6197	Remote Similarity	NPD8444	Approved
0.6197	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD8368	Discontinued
0.6183	Remote Similarity	NPD1700	Approved
0.6179	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5169	Approved
0.6176	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5135	Approved
0.6172	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD8407	Phase 2
0.616	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.616	Remote Similarity	NPD4753	Phase 2
0.616	Remote Similarity	NPD6080	Approved
0.616	Remote Similarity	NPD6904	Approved
0.616	Remote Similarity	NPD6673	Approved
0.616	Remote Similarity	NPD6101	Approved
0.6148	Remote Similarity	NPD6400	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data