NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	502.18
Volume:	478.997
LogP:	2.362
LogD:	1.154
LogS:	-3.617
# Rotatable Bonds:	1
TPSA:	156.03
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	6.071
Fsp3:	0.654
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:	-5.616
MDCK Permeability:	1.3851510630047414e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.871
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.709

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.756
Plasma Protein Binding (PPB):	75.80419158935547%
Volume Distribution (VD):	0.6
Pgp-substrate:	25.139362335205078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.324
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.461
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	10.44
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.172
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.213
Carcinogencity:	0.488
Eye Corrosion:	0.006
Eye Irritation:	0.143
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC476862

Natural Product ID:	NPC476862
*Common Name:**	(1R,2R,4S,7S,8S,10S,11R,12R,18R)-10-hydroxy-7-(2-hydroxy-5-oxo-2H-furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione
IUPAC Name:	(1R,2R,4S,7S,8S,10S,11R,12R,18R)-10-hydroxy-7-(2-hydroxy-5-oxo-2H-furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione
Synonyms:
Standard InCHIKey:	RAWMXEPWEDJCIT-FXMLJRRDSA-N
Standard InCHI:	InChI=1S/C26H30O10/c1-22(2)13-9-14(28)25(5)17(23(13,3)7-6-15(29)35-22)12(27)10-24(4)18(11-8-16(30)33-20(11)31)34-21(32)19-26(24,25)36-19/h6-8,12-13,17-20,27,31H,9-10H2,1-5H3/t12-,13-,17+,18+,19+,20?,23-,24-,25+,26+/m0/s1
SMILES:	C[C@@]12C[C@@H]([C@@H]3[C@]4(C=CC(=O)OC([C@@H]4CC(=O)[C@]3([C@@]15[C@H](O5)C(=O)O[C@@H]2C6=CC(=O)OC6O)C)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90670775
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 NPC476862 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	296
0.1-0.2	1722
0.2-0.3	4657
0.3-0.4	7729
0.4-0.5	11709
0.5-0.6	9312
0.6-0.7	5254
0.7-0.8	1928
0.8-0.85	82
0.85-0.9	1
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476863
0.9669	High Similarity	NPC476855
0.9667	High Similarity	NPC476859
0.9587	High Similarity	NPC476854
0.9508	High Similarity	NPC476852
0.9426	High Similarity	NPC476851
0.8537	High Similarity	NPC268958
0.8492	Intermediate Similarity	NPC470922
0.8462	Intermediate Similarity	NPC168879
0.8438	Intermediate Similarity	NPC473620
0.8425	Intermediate Similarity	NPC225049
0.8397	Intermediate Similarity	NPC471234
0.8346	Intermediate Similarity	NPC476729
0.8346	Intermediate Similarity	NPC140045
0.8346	Intermediate Similarity	NPC295885
0.8346	Intermediate Similarity	NPC24651
0.8333	Intermediate Similarity	NPC312833
0.832	Intermediate Similarity	NPC48692
0.8306	Intermediate Similarity	NPC240509
0.8293	Intermediate Similarity	NPC270478
0.8281	Intermediate Similarity	NPC222307
0.8271	Intermediate Similarity	NPC190065
0.8271	Intermediate Similarity	NPC141215
0.8271	Intermediate Similarity	NPC251998
0.8271	Intermediate Similarity	NPC243014
0.8271	Intermediate Similarity	NPC471089
0.8268	Intermediate Similarity	NPC67251
0.8268	Intermediate Similarity	NPC91693
0.8268	Intermediate Similarity	NPC105926
0.8268	Intermediate Similarity	NPC265557
0.8268	Intermediate Similarity	NPC18945
0.8254	Intermediate Similarity	NPC470779
0.8254	Intermediate Similarity	NPC477046
0.8254	Intermediate Similarity	NPC102822
0.8244	Intermediate Similarity	NPC102316
0.8244	Intermediate Similarity	NPC231240
0.8231	Intermediate Similarity	NPC104382
0.8231	Intermediate Similarity	NPC472770
0.8231	Intermediate Similarity	NPC175186
0.8226	Intermediate Similarity	NPC474483
0.8217	Intermediate Similarity	NPC42399
0.8217	Intermediate Similarity	NPC287423
0.8217	Intermediate Similarity	NPC298841
0.8211	Intermediate Similarity	NPC299849
0.8209	Intermediate Similarity	NPC596
0.8195	Intermediate Similarity	NPC262813
0.8182	Intermediate Similarity	NPC316915
0.8175	Intermediate Similarity	NPC107338
0.8175	Intermediate Similarity	NPC112038
0.8175	Intermediate Similarity	NPC109607
0.8168	Intermediate Similarity	NPC471170
0.816	Intermediate Similarity	NPC234522
0.816	Intermediate Similarity	NPC251310
0.8154	Intermediate Similarity	NPC270109
0.8145	Intermediate Similarity	NPC471816
0.8145	Intermediate Similarity	NPC213084
0.8145	Intermediate Similarity	NPC190185
0.813	Intermediate Similarity	NPC159333
0.8125	Intermediate Similarity	NPC120724
0.8125	Intermediate Similarity	NPC472399
0.8125	Intermediate Similarity	NPC469789
0.8125	Intermediate Similarity	NPC472768
0.8106	Intermediate Similarity	NPC6274
0.8106	Intermediate Similarity	NPC472769
0.8106	Intermediate Similarity	NPC33378
0.8106	Intermediate Similarity	NPC254146
0.8106	Intermediate Similarity	NPC471855
0.8106	Intermediate Similarity	NPC478154
0.8106	Intermediate Similarity	NPC475139
0.8106	Intermediate Similarity	NPC180902
0.8095	Intermediate Similarity	NPC469488
0.8095	Intermediate Similarity	NPC476529
0.8095	Intermediate Similarity	NPC475775
0.8092	Intermediate Similarity	NPC470851
0.8092	Intermediate Similarity	NPC473593
0.8092	Intermediate Similarity	NPC477196
0.808	Intermediate Similarity	NPC13713
0.808	Intermediate Similarity	NPC477116
0.808	Intermediate Similarity	NPC27999
0.808	Intermediate Similarity	NPC469684
0.8077	Intermediate Similarity	NPC470780
0.8077	Intermediate Similarity	NPC476008
0.8065	Intermediate Similarity	NPC261330
0.8062	Intermediate Similarity	NPC473709
0.8062	Intermediate Similarity	NPC473919
0.8049	Intermediate Similarity	NPC317687
0.8049	Intermediate Similarity	NPC90952
0.8047	Intermediate Similarity	NPC23786
0.8047	Intermediate Similarity	NPC470419
0.8047	Intermediate Similarity	NPC470265
0.8045	Intermediate Similarity	NPC478151
0.8033	Intermediate Similarity	NPC476766
0.8031	Intermediate Similarity	NPC476150
0.8031	Intermediate Similarity	NPC476127
0.803	Intermediate Similarity	NPC477197
0.803	Intermediate Similarity	NPC478155
0.803	Intermediate Similarity	NPC25998
0.8017	Intermediate Similarity	NPC476765
0.8016	Intermediate Similarity	NPC188667
0.8016	Intermediate Similarity	NPC297179
0.8016	Intermediate Similarity	NPC17772
0.8016	Intermediate Similarity	NPC470776
0.8016	Intermediate Similarity	NPC204552
0.8015	Intermediate Similarity	NPC477193
0.8015	Intermediate Similarity	NPC470850
0.8015	Intermediate Similarity	NPC477192
0.8015	Intermediate Similarity	NPC477191
0.8015	Intermediate Similarity	NPC477194
0.8015	Intermediate Similarity	NPC311534
0.8015	Intermediate Similarity	NPC236999
0.8	Intermediate Similarity	NPC477745
0.8	Intermediate Similarity	NPC293112
0.7985	Intermediate Similarity	NPC475154
0.7985	Intermediate Similarity	NPC100017
0.7985	Intermediate Similarity	NPC182266
0.7985	Intermediate Similarity	NPC475500
0.7985	Intermediate Similarity	NPC471136
0.7985	Intermediate Similarity	NPC471137
0.7985	Intermediate Similarity	NPC473548
0.7985	Intermediate Similarity	NPC223356
0.7984	Intermediate Similarity	NPC473802
0.7984	Intermediate Similarity	NPC264153
0.7984	Intermediate Similarity	NPC33360
0.7984	Intermediate Similarity	NPC94509
0.797	Intermediate Similarity	NPC478150
0.797	Intermediate Similarity	NPC100390
0.797	Intermediate Similarity	NPC476193
0.797	Intermediate Similarity	NPC478152
0.797	Intermediate Similarity	NPC477195
0.797	Intermediate Similarity	NPC478153
0.797	Intermediate Similarity	NPC312650
0.797	Intermediate Similarity	NPC254614
0.797	Intermediate Similarity	NPC476776
0.7969	Intermediate Similarity	NPC472000
0.7969	Intermediate Similarity	NPC470418
0.7969	Intermediate Similarity	NPC471999
0.7969	Intermediate Similarity	NPC472001
0.7969	Intermediate Similarity	NPC472401
0.7969	Intermediate Similarity	NPC67569
0.7967	Intermediate Similarity	NPC470246
0.7967	Intermediate Similarity	NPC317107
0.7955	Intermediate Similarity	NPC280029
0.7955	Intermediate Similarity	NPC477077
0.7955	Intermediate Similarity	NPC477079
0.7955	Intermediate Similarity	NPC477076
0.7955	Intermediate Similarity	NPC244296
0.7955	Intermediate Similarity	NPC476966
0.7955	Intermediate Similarity	NPC141600
0.7955	Intermediate Similarity	NPC115656
0.7955	Intermediate Similarity	NPC82380
0.7955	Intermediate Similarity	NPC162495
0.7955	Intermediate Similarity	NPC47995
0.7955	Intermediate Similarity	NPC107536
0.7955	Intermediate Similarity	NPC470518
0.7955	Intermediate Similarity	NPC1314
0.7955	Intermediate Similarity	NPC88311
0.7955	Intermediate Similarity	NPC472267
0.7955	Intermediate Similarity	NPC252657
0.7955	Intermediate Similarity	NPC273878
0.7955	Intermediate Similarity	NPC97918
0.7955	Intermediate Similarity	NPC269484
0.7955	Intermediate Similarity	NPC470880
0.7955	Intermediate Similarity	NPC11577
0.7955	Intermediate Similarity	NPC265841
0.7955	Intermediate Similarity	NPC470913
0.7955	Intermediate Similarity	NPC471407
0.7955	Intermediate Similarity	NPC264192
0.7955	Intermediate Similarity	NPC252289
0.7955	Intermediate Similarity	NPC9470
0.7955	Intermediate Similarity	NPC305793
0.7953	Intermediate Similarity	NPC473839
0.7953	Intermediate Similarity	NPC472933
0.7953	Intermediate Similarity	NPC77689
0.7953	Intermediate Similarity	NPC473636
0.7953	Intermediate Similarity	NPC158963
0.7953	Intermediate Similarity	NPC470777
0.7953	Intermediate Similarity	NPC211093
0.7951	Intermediate Similarity	NPC220705
0.7939	Intermediate Similarity	NPC471940
0.7939	Intermediate Similarity	NPC473253
0.7939	Intermediate Similarity	NPC471357
0.7939	Intermediate Similarity	NPC146456
0.7939	Intermediate Similarity	NPC469757
0.7939	Intermediate Similarity	NPC117702
0.7937	Intermediate Similarity	NPC287343
0.7937	Intermediate Similarity	NPC475809
0.7937	Intermediate Similarity	NPC176513
0.7937	Intermediate Similarity	NPC473968
0.7937	Intermediate Similarity	NPC470775
0.7937	Intermediate Similarity	NPC146432
0.7937	Intermediate Similarity	NPC474654
0.7937	Intermediate Similarity	NPC97908
0.7937	Intermediate Similarity	NPC134430
0.7937	Intermediate Similarity	NPC470854
0.7937	Intermediate Similarity	NPC470778
0.7937	Intermediate Similarity	NPC122033
0.7929	Intermediate Similarity	NPC48813
0.7929	Intermediate Similarity	NPC194854
0.7926	Intermediate Similarity	NPC171619
0.7926	Intermediate Similarity	NPC279915

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 NPC476862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	1866
0.2-0.3	3776
0.3-0.4	2085
0.4-0.5	699
0.5-0.6	277
0.6-0.7	147
0.7-0.8	38
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
0.7869	Intermediate Similarity	NPD6686	Approved
0.7846	Intermediate Similarity	NPD8328	Phase 3
0.782	Intermediate Similarity	NPD7319	Approved
0.7769	Intermediate Similarity	NPD6370	Approved
0.7752	Intermediate Similarity	NPD6319	Approved
0.7744	Intermediate Similarity	NPD7736	Approved
0.7727	Intermediate Similarity	NPD7507	Approved
0.7724	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7115	Discovery
0.7652	Intermediate Similarity	NPD7492	Approved
0.7615	Intermediate Similarity	NPD6054	Approved
0.76	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6616	Approved
0.7557	Intermediate Similarity	NPD6015	Approved
0.7557	Intermediate Similarity	NPD6016	Approved
0.7537	Intermediate Similarity	NPD8293	Discontinued
0.7537	Intermediate Similarity	NPD7078	Approved
0.752	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD5988	Approved
0.748	Intermediate Similarity	NPD8297	Approved
0.748	Intermediate Similarity	NPD6882	Approved
0.7402	Intermediate Similarity	NPD6650	Approved
0.7402	Intermediate Similarity	NPD6649	Approved
0.7385	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5697	Approved
0.7348	Intermediate Similarity	NPD6059	Approved
0.7328	Intermediate Similarity	NPD7328	Approved
0.7328	Intermediate Similarity	NPD7327	Approved
0.7302	Intermediate Similarity	NPD6881	Approved
0.7302	Intermediate Similarity	NPD6899	Approved
0.7293	Intermediate Similarity	NPD8513	Phase 3
0.7293	Intermediate Similarity	NPD8516	Approved
0.7293	Intermediate Similarity	NPD8517	Approved
0.7293	Intermediate Similarity	NPD8515	Approved
0.7287	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD7516	Approved
0.7244	Intermediate Similarity	NPD6014	Approved
0.7244	Intermediate Similarity	NPD6373	Approved
0.7244	Intermediate Similarity	NPD6012	Approved
0.7244	Intermediate Similarity	NPD6013	Approved
0.7244	Intermediate Similarity	NPD6372	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	NPD6011	Approved
0.7164	Intermediate Similarity	NPD6921	Approved
0.7164	Intermediate Similarity	NPD5983	Phase 2
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7132	Intermediate Similarity	NPD6617	Approved
0.7132	Intermediate Similarity	NPD6847	Approved
0.7132	Intermediate Similarity	NPD6869	Approved
0.7132	Intermediate Similarity	NPD8130	Phase 1
0.709	Intermediate Similarity	NPD8294	Approved
0.709	Intermediate Similarity	NPD8377	Approved
0.7087	Intermediate Similarity	NPD5701	Approved
0.7054	Intermediate Similarity	NPD4634	Approved
0.704	Intermediate Similarity	NPD5211	Phase 2
0.7037	Intermediate Similarity	NPD8379	Approved
0.7037	Intermediate Similarity	NPD8378	Approved
0.7037	Intermediate Similarity	NPD7503	Approved
0.7037	Intermediate Similarity	NPD8296	Approved
0.7037	Intermediate Similarity	NPD8380	Approved
0.7037	Intermediate Similarity	NPD8033	Approved
0.7037	Intermediate Similarity	NPD8335	Approved
0.7031	Intermediate Similarity	NPD7320	Approved
0.7016	Intermediate Similarity	NPD7640	Approved
0.7016	Intermediate Similarity	NPD7639	Approved
0.6977	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6336	Discontinued
0.6953	Remote Similarity	NPD6412	Phase 2
0.695	Remote Similarity	NPD7260	Phase 2
0.6935	Remote Similarity	NPD7638	Approved
0.6929	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD6371	Approved
0.6894	Remote Similarity	NPD8133	Approved
0.688	Remote Similarity	NPD5286	Approved
0.688	Remote Similarity	NPD5285	Approved
0.688	Remote Similarity	NPD4696	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.6857	Remote Similarity	NPD6033	Approved
0.6825	Remote Similarity	NPD5344	Discontinued
0.68	Remote Similarity	NPD5696	Approved
0.6791	Remote Similarity	NPD6274	Approved
0.6786	Remote Similarity	NPD8074	Phase 3
0.6772	Remote Similarity	NPD5225	Approved
0.6772	Remote Similarity	NPD4633	Approved
0.6772	Remote Similarity	NPD5226	Approved
0.6772	Remote Similarity	NPD5224	Approved
0.6765	Remote Similarity	NPD7101	Approved
0.6765	Remote Similarity	NPD7100	Approved
0.6742	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6317	Approved
0.672	Remote Similarity	NPD4755	Approved
0.6719	Remote Similarity	NPD5174	Approved
0.6719	Remote Similarity	NPD5175	Approved
0.6712	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD5223	Approved
0.6692	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6335	Approved
0.6691	Remote Similarity	NPD6314	Approved
0.6691	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD4730	Approved
0.6641	Remote Similarity	NPD4729	Approved
0.664	Remote Similarity	NPD5222	Approved
0.664	Remote Similarity	NPD5221	Approved
0.664	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6698	Approved
0.6639	Remote Similarity	NPD46	Approved
0.6614	Remote Similarity	NPD4700	Approved
0.6614	Remote Similarity	NPD6648	Approved
0.6587	Remote Similarity	NPD6083	Phase 2
0.6587	Remote Similarity	NPD5173	Approved
0.6587	Remote Similarity	NPD6084	Phase 2
0.6571	Remote Similarity	NPD7642	Approved
0.656	Remote Similarity	NPD4629	Approved
0.656	Remote Similarity	NPD5210	Approved
0.6552	Remote Similarity	NPD6845	Suspended
0.6547	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6868	Approved
0.6541	Remote Similarity	NPD5251	Approved
0.6541	Remote Similarity	NPD5249	Phase 3
0.6541	Remote Similarity	NPD5248	Approved
0.6541	Remote Similarity	NPD5250	Approved
0.6541	Remote Similarity	NPD5247	Approved
0.6535	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3573	Approved
0.6528	Remote Similarity	NPD5956	Approved
0.6512	Remote Similarity	NPD7632	Discontinued
0.6508	Remote Similarity	NPD4697	Phase 3
0.6489	Remote Similarity	NPD4768	Approved
0.6489	Remote Similarity	NPD4767	Approved
0.648	Remote Similarity	NPD5282	Discontinued
0.6457	Remote Similarity	NPD7902	Approved
0.6454	Remote Similarity	NPD7829	Approved
0.6454	Remote Similarity	NPD7830	Approved
0.6452	Remote Similarity	NPD6079	Approved
0.6444	Remote Similarity	NPD6053	Discontinued
0.6443	Remote Similarity	NPD6334	Approved
0.6443	Remote Similarity	NPD6333	Approved
0.6429	Remote Similarity	NPD7799	Discontinued
0.6429	Remote Similarity	NPD6908	Approved
0.6429	Remote Similarity	NPD6909	Approved
0.6429	Remote Similarity	NPD5695	Phase 3
0.64	Remote Similarity	NPD5778	Approved
0.64	Remote Similarity	NPD5779	Approved
0.6391	Remote Similarity	NPD5128	Approved
0.6387	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.637	Remote Similarity	NPD5216	Approved
0.637	Remote Similarity	NPD5217	Approved
0.637	Remote Similarity	NPD5215	Approved
0.6364	Remote Similarity	NPD1694	Approved
0.6349	Remote Similarity	NPD7748	Approved
0.6338	Remote Similarity	NPD6067	Discontinued
0.6336	Remote Similarity	NPD4754	Approved
0.6327	Remote Similarity	NPD8338	Approved
0.632	Remote Similarity	NPD7515	Phase 2
0.632	Remote Similarity	NPD6411	Approved
0.632	Remote Similarity	NPD5693	Phase 1
0.632	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD3618	Phase 1
0.6309	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5169	Approved
0.6296	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5135	Approved
0.629	Remote Similarity	NPD5328	Approved
0.627	Remote Similarity	NPD6399	Phase 3
0.6268	Remote Similarity	NPD8080	Discontinued
0.625	Remote Similarity	NPD5127	Approved
0.6242	Remote Similarity	NPD8415	Approved
0.624	Remote Similarity	NPD7838	Discovery
0.624	Remote Similarity	NPD5785	Approved
0.622	Remote Similarity	NPD7900	Approved
0.622	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6672	Approved
0.621	Remote Similarity	NPD5737	Approved
0.6197	Remote Similarity	NPD8444	Approved
0.619	Remote Similarity	NPD6914	Discontinued
0.6185	Remote Similarity	NPD8368	Discontinued
0.6183	Remote Similarity	NPD1700	Approved
0.6179	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD8407	Phase 2
0.6164	Remote Similarity	NPD8336	Approved
0.6164	Remote Similarity	NPD8337	Approved
0.616	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.616	Remote Similarity	NPD4753	Phase 2
0.616	Remote Similarity	NPD6101	Approved
0.6148	Remote Similarity	NPD5168	Approved
0.6142	Remote Similarity	NPD4202	Approved
0.6138	Remote Similarity	NPD8451	Approved
0.6124	Remote Similarity	NPD7839	Suspended
0.6115	Remote Similarity	NPD5167	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