NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	575.25
Volume:	582.939
LogP:	3.593
LogD:	2.108
LogS:	-4.384
# Rotatable Bonds:	6
TPSA:	121.25
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	5.416
Fsp3:	0.515
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:	-5.347
MDCK Permeability:	2.172901076846756e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.12
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.823
30% Bioavailability (F30%):	0.444

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	97.14785766601562%
Volume Distribution (VD):	2.137
Pgp-substrate:	4.085165023803711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.251
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.731
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.911
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.393
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.51

ADMET: Excretion

Clearance (CL):	10.849
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.493
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.157
Skin Sensitization:	0.209
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC477902

Natural Product ID:	NPC477902
*Common Name:**	[(3R,4aR,5S,6R,6aR,10R,10bR)-10-benzoyloxy-5-hydroxy-4a,6a,7,10b-tetramethyl-2'-oxospiro[2,5,6,9,10,10a-hexahydro-1H-benzo[f]chromene-3,4'-oxolane]-6-yl] pyridine-3-carboxylate
IUPAC Name:	[(3R,4aR,5S,6R,6aR,10R,10bR)-10-benzoyloxy-5-hydroxy-4a,6a,7,10b-tetramethyl-2'-oxospiro[2,5,6,9,10,10a-hexahydro-1H-benzo[f]chromene-3,4'-oxolane]-6-yl] pyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	LHDUPMAARYESGH-PSANYURBSA-N
Standard InCHI:	InChI=1S/C33H37NO8/c1-20-12-13-23(40-28(37)21-9-6-5-7-10-21)25-30(2)14-15-33(17-24(35)39-19-33)42-32(30,4)26(36)27(31(20,25)3)41-29(38)22-11-8-16-34-18-22/h5-12,16,18,23,25-27,36H,13-15,17,19H2,1-4H3/t23-,25?,26+,27+,30-,31+,32+,33-/m1/s1
SMILES:	CC1=CC[C@H](C2[C@]1([C@H]([C@@H]([C@]3([C@@]2(CC[C@@]4(O3)CC(=O)OC4)C)C)O)OC(=O)C5=CN=CC=C5)C)OC(=O)C6=CC=CC=C6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122186893
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	34200	nM	PMID[26331882]

☑ 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 NPC477902 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	329
0.1-0.2	1387
0.2-0.3	3017
0.3-0.4	9341
0.4-0.5	17662
0.5-0.6	8762
0.6-0.7	1887
0.7-0.8	122
0.8-0.85	53
0.85-0.9	27
0.9-0.95	85
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC124029
0.9802	High Similarity	NPC211920
0.9659	High Similarity	NPC477906
0.9652	High Similarity	NPC477903
0.96	High Similarity	NPC62367
0.9557	High Similarity	NPC471980
0.9552	High Similarity	NPC216428
0.9552	High Similarity	NPC301368
0.9552	High Similarity	NPC84815
0.9548	High Similarity	NPC264674
0.951	High Similarity	NPC477900
0.951	High Similarity	NPC477899
0.9507	High Similarity	NPC235364
0.9507	High Similarity	NPC127720
0.9507	High Similarity	NPC127026
0.9502	High Similarity	NPC294579
0.9502	High Similarity	NPC144779
0.95	High Similarity	NPC42678
0.95	High Similarity	NPC477909
0.95	High Similarity	NPC477907
0.9469	High Similarity	NPC96801
0.9469	High Similarity	NPC150698
0.9458	High Similarity	NPC477912
0.9453	High Similarity	NPC6981
0.9453	High Similarity	NPC471016
0.9453	High Similarity	NPC475408
0.9453	High Similarity	NPC471014
0.9415	High Similarity	NPC26881
0.9409	High Similarity	NPC477901
0.9403	High Similarity	NPC470306
0.936	High Similarity	NPC472555
0.9353	High Similarity	NPC4421
0.935	High Similarity	NPC472553
0.9324	High Similarity	NPC475601
0.932	High Similarity	NPC328154
0.931	High Similarity	NPC473089
0.931	High Similarity	NPC6576
0.931	High Similarity	NPC158020
0.931	High Similarity	NPC75600
0.931	High Similarity	NPC473115
0.931	High Similarity	NPC212768
0.9279	High Similarity	NPC471190
0.9279	High Similarity	NPC475644
0.9279	High Similarity	NPC471977
0.9279	High Similarity	NPC470486
0.9275	High Similarity	NPC148860
0.9261	High Similarity	NPC477908
0.9261	High Similarity	NPC206343
0.9238	High Similarity	NPC469748
0.9238	High Similarity	NPC30456
0.9234	High Similarity	NPC91125
0.9231	High Similarity	NPC87152
0.9231	High Similarity	NPC477787
0.9231	High Similarity	NPC228377
0.9231	High Similarity	NPC328186
0.9231	High Similarity	NPC476110
0.9231	High Similarity	NPC475631
0.9231	High Similarity	NPC122968
0.9231	High Similarity	NPC475600
0.9227	High Similarity	NPC475137
0.9227	High Similarity	NPC473850
0.9227	High Similarity	NPC475498
0.9223	High Similarity	NPC477911
0.9212	High Similarity	NPC477910
0.92	High Similarity	NPC304179
0.92	High Similarity	NPC472550
0.92	High Similarity	NPC48042
0.919	High Similarity	NPC475303
0.919	High Similarity	NPC316841
0.919	High Similarity	NPC475596
0.9183	High Similarity	NPC473506
0.9179	High Similarity	NPC57797
0.9179	High Similarity	NPC250807
0.9179	High Similarity	NPC76565
0.9163	High Similarity	NPC319128
0.9151	High Similarity	NPC327769
0.915	High Similarity	NPC63041
0.9104	High Similarity	NPC237702
0.91	High Similarity	NPC473689
0.91	High Similarity	NPC292416
0.9095	High Similarity	NPC475362
0.907	High Similarity	NPC253482
0.9069	High Similarity	NPC228331
0.9061	High Similarity	NPC475426
0.9061	High Similarity	NPC35208
0.9061	High Similarity	NPC475406
0.9057	High Similarity	NPC320324
0.9057	High Similarity	NPC244839
0.9057	High Similarity	NPC319880
0.9048	High Similarity	NPC146824
0.9038	High Similarity	NPC477788
0.9032	High Similarity	NPC475648
0.9019	High Similarity	NPC38959
0.9019	High Similarity	NPC327904
0.8972	High Similarity	NPC170751
0.8932	High Similarity	NPC30570
0.8889	High Similarity	NPC162812
0.8878	High Similarity	NPC292517
0.8786	High Similarity	NPC476467
0.875	High Similarity	NPC238278
0.8704	High Similarity	NPC213143
0.8692	High Similarity	NPC285411
0.8692	High Similarity	NPC14116
0.8651	High Similarity	NPC134384
0.8651	High Similarity	NPC311196
0.8649	High Similarity	NPC180668
0.8649	High Similarity	NPC148896
0.8649	High Similarity	NPC471013
0.8606	High Similarity	NPC280473
0.8606	High Similarity	NPC323551
0.8598	High Similarity	NPC233727
0.8565	High Similarity	NPC41724
0.8565	High Similarity	NPC51008
0.8551	High Similarity	NPC472752
0.8546	High Similarity	NPC471015
0.8544	High Similarity	NPC475835
0.8537	High Similarity	NPC289086
0.8496	Intermediate Similarity	NPC10904
0.8483	Intermediate Similarity	NPC193361
0.8483	Intermediate Similarity	NPC62844
0.8444	Intermediate Similarity	NPC475533
0.8407	Intermediate Similarity	NPC324619
0.8407	Intermediate Similarity	NPC475315
0.8404	Intermediate Similarity	NPC187494
0.8389	Intermediate Similarity	NPC165837
0.8369	Intermediate Similarity	NPC471978
0.8362	Intermediate Similarity	NPC473833
0.8268	Intermediate Similarity	NPC326930
0.8268	Intermediate Similarity	NPC475301
0.8268	Intermediate Similarity	NPC85879
0.8268	Intermediate Similarity	NPC53255
0.8238	Intermediate Similarity	NPC476090
0.8233	Intermediate Similarity	NPC13603
0.8233	Intermediate Similarity	NPC319556
0.8213	Intermediate Similarity	NPC328928
0.8208	Intermediate Similarity	NPC470189
0.8208	Intermediate Similarity	NPC40919
0.8186	Intermediate Similarity	NPC471979
0.8164	Intermediate Similarity	NPC470279
0.8152	Intermediate Similarity	NPC470190
0.8143	Intermediate Similarity	NPC309498
0.814	Intermediate Similarity	NPC207531
0.8137	Intermediate Similarity	NPC103230
0.8037	Intermediate Similarity	NPC253314
0.7876	Intermediate Similarity	NPC471004
0.7834	Intermediate Similarity	NPC111732
0.781	Intermediate Similarity	NPC324245
0.781	Intermediate Similarity	NPC320748
0.7783	Intermediate Similarity	NPC32451
0.7783	Intermediate Similarity	NPC328559
0.7736	Intermediate Similarity	NPC79223
0.7678	Intermediate Similarity	NPC329024
0.7604	Intermediate Similarity	NPC156044
0.7559	Intermediate Similarity	NPC317672
0.7559	Intermediate Similarity	NPC59033
0.7512	Intermediate Similarity	NPC25442
0.7512	Intermediate Similarity	NPC12944
0.7489	Intermediate Similarity	NPC37473
0.7454	Intermediate Similarity	NPC155792
0.7437	Intermediate Similarity	NPC107123
0.7429	Intermediate Similarity	NPC44354
0.7427	Intermediate Similarity	NPC317010
0.7427	Intermediate Similarity	NPC471997
0.7422	Intermediate Similarity	NPC141385
0.7417	Intermediate Similarity	NPC476516
0.7342	Intermediate Similarity	NPC314834
0.7304	Intermediate Similarity	NPC235885
0.7302	Intermediate Similarity	NPC109922
0.7295	Intermediate Similarity	NPC478045
0.7293	Intermediate Similarity	NPC106593
0.7281	Intermediate Similarity	NPC160127
0.7281	Intermediate Similarity	NPC50997
0.7256	Intermediate Similarity	NPC135950
0.7254	Intermediate Similarity	NPC473441
0.7254	Intermediate Similarity	NPC131273
0.7252	Intermediate Similarity	NPC470280
0.7244	Intermediate Similarity	NPC317752
0.7229	Intermediate Similarity	NPC141428
0.7222	Intermediate Similarity	NPC242662
0.7222	Intermediate Similarity	NPC191193
0.7222	Intermediate Similarity	NPC215892
0.7222	Intermediate Similarity	NPC321072
0.7217	Intermediate Similarity	NPC328798
0.7217	Intermediate Similarity	NPC325775
0.7215	Intermediate Similarity	NPC136573
0.7215	Intermediate Similarity	NPC176371
0.7212	Intermediate Similarity	NPC274842
0.7207	Intermediate Similarity	NPC314297
0.7207	Intermediate Similarity	NPC315545
0.7205	Intermediate Similarity	NPC140311
0.7202	Intermediate Similarity	NPC90358
0.7202	Intermediate Similarity	NPC103361
0.7202	Intermediate Similarity	NPC123395
0.7202	Intermediate Similarity	NPC107828
0.72	Intermediate Similarity	NPC318299
0.7196	Intermediate Similarity	NPC473400
0.7196	Intermediate Similarity	NPC471754
0.7196	Intermediate Similarity	NPC324251
0.7196	Intermediate Similarity	NPC206211
0.7196	Intermediate Similarity	NPC471629

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 NPC477902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	529
0.2-0.3	670
0.3-0.4	1730
0.4-0.5	3346
0.5-0.6	2108
0.6-0.7	522
0.7-0.8	25
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
0.8282	Intermediate Similarity	NPD8468	Phase 2
0.799	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7396	Approved
0.7583	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD3795	Approved
0.7477	Intermediate Similarity	NPD3794	Approved
0.7466	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD1483	Discontinued
0.7378	Intermediate Similarity	NPD8325	Phase 3
0.7378	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD8326	Phase 3
0.7319	Intermediate Similarity	NPD5891	Approved
0.7286	Intermediate Similarity	NPD820	Phase 3
0.726	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7010	Phase 3
0.7228	Intermediate Similarity	NPD6635	Approved
0.7189	Intermediate Similarity	NPD8485	Approved
0.7177	Intermediate Similarity	NPD7708	Approved
0.7155	Intermediate Similarity	NPD7885	Phase 2
0.7155	Intermediate Similarity	NPD7886	Phase 2
0.7131	Intermediate Similarity	NPD7803	Approved
0.713	Intermediate Similarity	NPD3280	Approved
0.7124	Intermediate Similarity	NPD7069	Discontinued
0.7105	Intermediate Similarity	NPD3393	Approved
0.7105	Intermediate Similarity	NPD3394	Approved
0.7105	Intermediate Similarity	NPD3389	Approved
0.7103	Intermediate Similarity	NPD7233	Approved
0.7103	Intermediate Similarity	NPD7234	Approved
0.7091	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4417	Approved
0.7068	Intermediate Similarity	NPD7955	Approved
0.7068	Intermediate Similarity	NPD7956	Approved
0.7067	Intermediate Similarity	NPD6529	Discontinued
0.7061	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8479	Phase 2
0.704	Intermediate Similarity	NPD3947	Discontinued
0.7022	Intermediate Similarity	NPD2509	Approved
0.7022	Intermediate Similarity	NPD2510	Approved
0.7	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7778	Approved
0.7	Intermediate Similarity	NPD53	Approved
0.7	Intermediate Similarity	NPD7777	Approved
0.6991	Remote Similarity	NPD8360	Approved
0.6991	Remote Similarity	NPD8063	Discontinued
0.6991	Remote Similarity	NPD8361	Approved
0.6991	Remote Similarity	NPD8435	Approved
0.698	Remote Similarity	NPD6026	Approved
0.6971	Remote Similarity	NPD485	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7878	Phase 2
0.6968	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2336	Approved
0.6953	Remote Similarity	NPD4301	Approved
0.6935	Remote Similarity	NPD9271	Approved
0.6929	Remote Similarity	NPD8409	Suspended
0.692	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6642	Approved
0.6919	Remote Similarity	NPD6641	Approved
0.6916	Remote Similarity	NPD4506	Discontinued
0.6893	Remote Similarity	NPD5088	Discontinued
0.6889	Remote Similarity	NPD6987	Phase 1
0.6878	Remote Similarity	NPD2511	Approved
0.6875	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6770	Approved
0.6862	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5475	Discontinued
0.6853	Remote Similarity	NPD4989	Phase 2
0.6847	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7707	Approved
0.6835	Remote Similarity	NPD8289	Discontinued
0.6833	Remote Similarity	NPD2307	Discontinued
0.6826	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD2831	Approved
0.6787	Remote Similarity	NPD4427	Phase 2
0.6786	Remote Similarity	NPD4601	Approved
0.6786	Remote Similarity	NPD4600	Approved
0.6784	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD4376	Phase 3
0.6759	Remote Similarity	NPD8091	Phase 3
0.6757	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9074	Approved
0.675	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9075	Approved
0.6748	Remote Similarity	NPD8412	Phase 1
0.6743	Remote Similarity	NPD6791	Phase 2
0.6742	Remote Similarity	NPD6361	Phase 2
0.674	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8407	Phase 2
0.6726	Remote Similarity	NPD7187	Phase 2
0.6723	Remote Similarity	NPD7404	Approved
0.6711	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD8356	Approved
0.6707	Remote Similarity	NPD6790	Phase 1
0.6692	Remote Similarity	NPD8467	Approved
0.6692	Remote Similarity	NPD8466	Approved
0.6692	Remote Similarity	NPD8465	Approved
0.6682	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD1926	Approved
0.668	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8021	Approved
0.6667	Remote Similarity	NPD4948	Discontinued
0.6667	Remote Similarity	NPD8020	Approved
0.6667	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5901	Discontinued
0.6654	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD3925	Approved
0.6652	Remote Similarity	NPD5003	Discontinued
0.6652	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.664	Remote Similarity	NPD8370	Discontinued
0.664	Remote Similarity	NPD7417	Discontinued
0.6638	Remote Similarity	NPD7957	Phase 1
0.6638	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7470	Discontinued
0.6638	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD107	Approved
0.6625	Remote Similarity	NPD7426	Phase 1
0.6624	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5022	Discontinued
0.661	Remote Similarity	NPD7395	Discontinued
0.6609	Remote Similarity	NPD7562	Approved
0.6609	Remote Similarity	NPD5866	Approved
0.6598	Remote Similarity	NPD8430	Approved
0.6598	Remote Similarity	NPD4086	Phase 1
0.6597	Remote Similarity	NPD6298	Discontinued
0.6597	Remote Similarity	NPD5147	Discontinued
0.6596	Remote Similarity	NPD5490	Discontinued
0.6595	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD4528	Approved
0.6592	Remote Similarity	NPD8425	Approved
0.6592	Remote Similarity	NPD4529	Approved
0.6592	Remote Similarity	NPD8426	Approved
0.6592	Remote Similarity	NPD8460	Approved
0.6592	Remote Similarity	NPD8459	Approved
0.6592	Remote Similarity	NPD4526	Approved
0.659	Remote Similarity	NPD8363	Approved
0.659	Remote Similarity	NPD8364	Approved
0.659	Remote Similarity	NPD8368	Discontinued
0.6588	Remote Similarity	NPD6446	Discontinued
0.6587	Remote Similarity	NPD5482	Discontinued
0.6575	Remote Similarity	NPD4889	Approved
0.6574	Remote Similarity	NPD6276	Discontinued
0.6571	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD8404	Phase 2
0.6566	Remote Similarity	NPD8429	Approved
0.6566	Remote Similarity	NPD8428	Approved
0.6566	Remote Similarity	NPD8427	Approved
0.656	Remote Similarity	NPD7967	Discontinued
0.6556	Remote Similarity	NPD5640	Discontinued
0.655	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3006	Discontinued
0.654	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8462	Phase 1
0.6537	Remote Similarity	NPD3371	Approved
0.6533	Remote Similarity	NPD2896	Discontinued
0.6533	Remote Similarity	NPD6226	Phase 3
0.6532	Remote Similarity	NPD6281	Approved
0.6531	Remote Similarity	NPD4373	Phase 2
0.6524	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6874	Approved
0.652	Remote Similarity	NPD1270	Approved
0.6518	Remote Similarity	NPD5805	Approved
0.6516	Remote Similarity	NPD6962	Phase 2
0.6515	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7191	Phase 2
0.6504	Remote Similarity	NPD6206	Phase 1
0.65	Remote Similarity	NPD6995	Phase 1
0.6498	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6479	Discontinued
0.6491	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4897	Phase 2
0.6478	Remote Similarity	NPD5513	Phase 2
0.6478	Remote Similarity	NPD6176	Phase 1
0.6473	Remote Similarity	NPD3923	Approved
0.6473	Remote Similarity	NPD3921	Approved
0.6473	Remote Similarity	NPD6665	Discontinued
0.6473	Remote Similarity	NPD3924	Approved
0.6473	Remote Similarity	NPD3922	Approved
0.6471	Remote Similarity	NPD4375	Approved
0.6468	Remote Similarity	NPD3816	Phase 1
0.6468	Remote Similarity	NPD3815	Phase 1
0.6459	Remote Similarity	NPD2581	Approved
0.6459	Remote Similarity	NPD2582	Approved
0.6458	Remote Similarity	NPD5507	Approved
0.6458	Remote Similarity	NPD5506	Approved
0.6457	Remote Similarity	NPD2564	Approved
0.6457	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8101	Phase 3
0.6457	Remote Similarity	NPD2565	Phase 2
0.6453	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7688	Phase 1
0.6444	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3178	Discontinued

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