NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	633.26
Volume:	638.395
LogP:	3.513
LogD:	2.301
LogS:	-3.692
# Rotatable Bonds:	11
TPSA:	165.62
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	5.04
Fsp3:	0.429
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:	-5.658
MDCK Permeability:	1.9065686501562595e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.149
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.899

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	99.15222930908203%
Volume Distribution (VD):	0.911
Pgp-substrate:	6.1981329917907715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.312
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.204
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.712
CYP2C9-substrate:	0.689
CYP2D6-inhibitor:	0.933
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	10.097
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.29
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.114
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: NPC477912

Natural Product ID:	NPC477912
*Common Name:**	[(1R,2S,3R,4S,8aR)-4-[(1S)-1-acetyloxy-2-(4-hydroxy-5-oxo-2H-furan-3-yl)ethyl]-2-benzoyloxy-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
IUPAC Name:	[(1R,2S,3R,4S,8aR)-4-[(1S)-1-acetyloxy-2-(4-hydroxy-5-oxo-2H-furan-3-yl)ethyl]-2-benzoyloxy-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	PMRCLNAMSQXGTL-QZXBMSDESA-N
Standard InCHI:	InChI=1S/C35H39NO10/c1-20-11-9-15-25-33(20,3)28(45-31(40)23-14-10-16-36-18-23)29(46-30(39)22-12-7-6-8-13-22)35(5,42)34(25,4)26(44-21(2)37)17-24-19-43-32(41)27(24)38/h6-8,10-14,16,18,25-26,28-29,38,42H,9,15,17,19H2,1-5H3/t25?,26-,28-,29-,33-,34-,35-/m0/s1
SMILES:	CC1=CCCC2[C@]1([C@H]([C@@H]([C@]([C@]2(C)[C@H](CC3=C(C(=O)OC3)O)OC(=O)C)(C)O)OC(=O)C4=CC=CC=C4)OC(=O)C5=CN=CC=C5)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122186903
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	>	50000	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 NPC477912 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	327
0.1-0.2	1400
0.2-0.3	3458
0.3-0.4	10233
0.4-0.5	16216
0.5-0.6	9080
0.6-0.7	1690
0.7-0.8	110
0.8-0.85	55
0.85-0.9	76
0.9-0.95	41
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC62367
0.98	High Similarity	NPC148860
0.9797	High Similarity	NPC216428
0.9745	High Similarity	NPC477909
0.9745	High Similarity	NPC42678
0.9745	High Similarity	NPC477907
0.965	High Similarity	NPC477911
0.9645	High Similarity	NPC477910
0.9598	High Similarity	NPC301368
0.9598	High Similarity	NPC84815
0.9594	High Similarity	NPC319128
0.9592	High Similarity	NPC472553
0.9554	High Similarity	NPC328154
0.95	High Similarity	NPC472555
0.9497	High Similarity	NPC471016
0.9497	High Similarity	NPC6981
0.9495	High Similarity	NPC228331
0.9458	High Similarity	NPC477902
0.9455	High Similarity	NPC127720
0.9455	High Similarity	NPC127026
0.945	High Similarity	NPC144779
0.945	High Similarity	NPC294579
0.9447	High Similarity	NPC470306
0.9439	High Similarity	NPC48042
0.9439	High Similarity	NPC304179
0.9439	High Similarity	NPC472550
0.9409	High Similarity	NPC471980
0.94	High Similarity	NPC471014
0.94	High Similarity	NPC206343
0.94	High Similarity	NPC475408
0.94	High Similarity	NPC477908
0.9397	High Similarity	NPC4421
0.9366	High Similarity	NPC124029
0.9324	High Similarity	NPC292416
0.9324	High Similarity	NPC96801
0.9324	High Similarity	NPC150698
0.9324	High Similarity	NPC473689
0.9289	High Similarity	NPC63041
0.9279	High Similarity	NPC244839
0.9279	High Similarity	NPC319880
0.9279	High Similarity	NPC320324
0.9272	High Similarity	NPC476110
0.9272	High Similarity	NPC228377
0.9272	High Similarity	NPC146824
0.9272	High Similarity	NPC475600
0.9272	High Similarity	NPC475601
0.9272	High Similarity	NPC87152
0.9272	High Similarity	NPC475631
0.9272	High Similarity	NPC122968
0.9272	High Similarity	NPC477787
0.9272	High Similarity	NPC328186
0.9272	High Similarity	NPC211920
0.9257	High Similarity	NPC473115
0.9257	High Similarity	NPC158020
0.9257	High Similarity	NPC473089
0.9257	High Similarity	NPC6576
0.9257	High Similarity	NPC75600
0.9257	High Similarity	NPC212768
0.9234	High Similarity	NPC237702
0.9227	High Similarity	NPC471977
0.9227	High Similarity	NPC471190
0.9227	High Similarity	NPC475362
0.9227	High Similarity	NPC470486
0.9227	High Similarity	NPC475644
0.922	High Similarity	NPC57797
0.922	High Similarity	NPC250807
0.922	High Similarity	NPC76565
0.9216	High Similarity	NPC477903
0.9204	High Similarity	NPC264674
0.919	High Similarity	NPC475406
0.9175	High Similarity	NPC473850
0.9175	High Similarity	NPC475137
0.9175	High Similarity	NPC475498
0.9147	High Similarity	NPC38959
0.9147	High Similarity	NPC327904
0.9139	High Similarity	NPC475303
0.9139	High Similarity	NPC316841
0.9139	High Similarity	NPC477906
0.9139	High Similarity	NPC475596
0.913	High Similarity	NPC473506
0.9095	High Similarity	NPC469748
0.9095	High Similarity	NPC30456
0.9082	High Similarity	NPC477899
0.9082	High Similarity	NPC477900
0.9078	High Similarity	NPC477788
0.9078	High Similarity	NPC235364
0.9019	High Similarity	NPC253482
0.9009	High Similarity	NPC35208
0.9009	High Similarity	NPC327769
0.899	High Similarity	NPC26881
0.8981	High Similarity	NPC477901
0.892	High Similarity	NPC170751
0.8905	High Similarity	NPC14116
0.8905	High Similarity	NPC285411
0.8894	High Similarity	NPC475648
0.8863	High Similarity	NPC134384
0.8863	High Similarity	NPC311196
0.8832	High Similarity	NPC475426
0.8824	High Similarity	NPC476467
0.8821	High Similarity	NPC91125
0.8756	High Similarity	NPC289086
0.8727	High Similarity	NPC475533
0.8698	High Similarity	NPC238278
0.8696	High Similarity	NPC30570
0.8688	High Similarity	NPC475315
0.8688	High Similarity	NPC324619
0.8654	High Similarity	NPC162812
0.8651	High Similarity	NPC213143
0.8641	High Similarity	NPC280473
0.8641	High Similarity	NPC323551
0.8641	High Similarity	NPC292517
0.8599	High Similarity	NPC51008
0.8599	High Similarity	NPC41724
0.8585	High Similarity	NPC472752
0.8578	High Similarity	NPC475835
0.8545	High Similarity	NPC233727
0.854	High Similarity	NPC475301
0.854	High Similarity	NPC326930
0.854	High Similarity	NPC85879
0.854	High Similarity	NPC53255
0.8514	High Similarity	NPC148896
0.8514	High Similarity	NPC180668
0.8514	High Similarity	NPC471013
0.8502	High Similarity	NPC13603
0.8496	Intermediate Similarity	NPC471015
0.8436	Intermediate Similarity	NPC187494
0.8413	Intermediate Similarity	NPC470189
0.8413	Intermediate Similarity	NPC40919
0.8398	Intermediate Similarity	NPC328928
0.8391	Intermediate Similarity	NPC473833
0.8363	Intermediate Similarity	NPC10904
0.8357	Intermediate Similarity	NPC470190
0.8349	Intermediate Similarity	NPC319556
0.8333	Intermediate Similarity	NPC165837
0.8319	Intermediate Similarity	NPC471978
0.8259	Intermediate Similarity	NPC103230
0.8255	Intermediate Similarity	NPC62844
0.8255	Intermediate Similarity	NPC207531
0.8255	Intermediate Similarity	NPC193361
0.8213	Intermediate Similarity	NPC471979
0.8107	Intermediate Similarity	NPC470279
0.8106	Intermediate Similarity	NPC476090
0.8086	Intermediate Similarity	NPC309498
0.7982	Intermediate Similarity	NPC253314
0.7902	Intermediate Similarity	NPC471004
0.786	Intermediate Similarity	NPC111732
0.7837	Intermediate Similarity	NPC320748
0.7837	Intermediate Similarity	NPC324245
0.781	Intermediate Similarity	NPC32451
0.781	Intermediate Similarity	NPC328559
0.7762	Intermediate Similarity	NPC79223
0.7711	Intermediate Similarity	NPC471997
0.7703	Intermediate Similarity	NPC329024
0.7628	Intermediate Similarity	NPC156044
0.7621	Intermediate Similarity	NPC44354
0.7583	Intermediate Similarity	NPC317672
0.7583	Intermediate Similarity	NPC59033
0.7571	Intermediate Similarity	NPC109922
0.7535	Intermediate Similarity	NPC12944
0.7535	Intermediate Similarity	NPC25442
0.7511	Intermediate Similarity	NPC37473
0.7395	Intermediate Similarity	NPC155792
0.7366	Intermediate Similarity	NPC317010
0.7366	Intermediate Similarity	NPC141385
0.7364	Intermediate Similarity	NPC476516
0.7311	Intermediate Similarity	NPC107123
0.7302	Intermediate Similarity	NPC123395
0.7302	Intermediate Similarity	NPC160127
0.7302	Intermediate Similarity	NPC50997
0.7286	Intermediate Similarity	NPC327699
0.7277	Intermediate Similarity	NPC135950
0.7277	Intermediate Similarity	NPC146724
0.7265	Intermediate Similarity	NPC317752
0.7253	Intermediate Similarity	NPC70155
0.7249	Intermediate Similarity	NPC235885
0.7245	Intermediate Similarity	NPC107287
0.7238	Intermediate Similarity	NPC325775
0.7238	Intermediate Similarity	NPC328798
0.7237	Intermediate Similarity	NPC106593
0.7233	Intermediate Similarity	NPC164340
0.7225	Intermediate Similarity	NPC140311
0.7222	Intermediate Similarity	NPC103361
0.722	Intermediate Similarity	NPC318299
0.7215	Intermediate Similarity	NPC477043
0.7212	Intermediate Similarity	NPC327373
0.7207	Intermediate Similarity	NPC314834
0.7205	Intermediate Similarity	NPC473667
0.7195	Intermediate Similarity	NPC470280
0.7177	Intermediate Similarity	NPC207851
0.7174	Intermediate Similarity	NPC141428
0.7157	Intermediate Similarity	NPC249614
0.7155	Intermediate Similarity	NPC15406
0.7137	Intermediate Similarity	NPC233334
0.7136	Intermediate Similarity	NPC275170
0.7136	Intermediate Similarity	NPC317882
0.7136	Intermediate Similarity	NPC306001
0.7136	Intermediate Similarity	NPC473300
0.7136	Intermediate Similarity	NPC453583
0.7136	Intermediate Similarity	NPC114974
0.7136	Intermediate Similarity	NPC471754

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 NPC477912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	532
0.2-0.3	691
0.3-0.4	1585
0.4-0.5	3277
0.5-0.6	2276
0.6-0.7	538
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
0.8393	Intermediate Similarity	NPD8468	Phase 2
0.8112	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD7396	Approved
0.7692	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3794	Approved
0.75	Intermediate Similarity	NPD3795	Approved
0.7489	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD820	Phase 3
0.7339	Intermediate Similarity	NPD7010	Phase 3
0.7337	Intermediate Similarity	NPD6635	Approved
0.7297	Intermediate Similarity	NPD7069	Discontinued
0.7265	Intermediate Similarity	NPD5891	Approved
0.7257	Intermediate Similarity	NPD1483	Discontinued
0.725	Intermediate Similarity	NPD5088	Discontinued
0.7202	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7886	Phase 2
0.7173	Intermediate Similarity	NPD7885	Phase 2
0.7168	Intermediate Similarity	NPD8325	Phase 3
0.7168	Intermediate Similarity	NPD8326	Phase 3
0.7168	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6529	Discontinued
0.7149	Intermediate Similarity	NPD3280	Approved
0.7136	Intermediate Similarity	NPD2831	Approved
0.7098	Intermediate Similarity	NPD4417	Approved
0.7073	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3947	Discontinued
0.7059	Intermediate Similarity	NPD6987	Phase 1
0.7051	Intermediate Similarity	NPD8485	Approved
0.7048	Intermediate Similarity	NPD3389	Approved
0.7048	Intermediate Similarity	NPD3394	Approved
0.7048	Intermediate Similarity	NPD3393	Approved
0.7042	Intermediate Similarity	NPD7234	Approved
0.7042	Intermediate Similarity	NPD7233	Approved
0.7041	Intermediate Similarity	NPD9271	Approved
0.704	Intermediate Similarity	NPD2510	Approved
0.704	Intermediate Similarity	NPD2509	Approved
0.7018	Intermediate Similarity	NPD4989	Phase 2
0.7	Intermediate Similarity	NPD6026	Approved
0.7	Intermediate Similarity	NPD8479	Phase 2
0.6986	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4506	Discontinued
0.693	Remote Similarity	NPD8360	Approved
0.693	Remote Similarity	NPD8361	Approved
0.693	Remote Similarity	NPD7707	Approved
0.693	Remote Similarity	NPD8435	Approved
0.693	Remote Similarity	NPD8063	Discontinued
0.692	Remote Similarity	NPD7708	Approved
0.6916	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6361	Phase 2
0.6898	Remote Similarity	NPD2336	Approved
0.6897	Remote Similarity	NPD4301	Approved
0.6883	Remote Similarity	NPD6770	Approved
0.6877	Remote Similarity	NPD7803	Approved
0.6872	Remote Similarity	NPD5475	Discontinued
0.687	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4376	Phase 3
0.6864	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD9074	Approved
0.6853	Remote Similarity	NPD9075	Approved
0.6837	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7955	Approved
0.6813	Remote Similarity	NPD7956	Approved
0.6809	Remote Similarity	NPD3925	Approved
0.6804	Remote Similarity	NPD4427	Phase 2
0.6787	Remote Similarity	NPD7778	Approved
0.6787	Remote Similarity	NPD7777	Approved
0.6787	Remote Similarity	NPD53	Approved
0.678	Remote Similarity	NPD5640	Discontinued
0.6777	Remote Similarity	NPD6642	Approved
0.6777	Remote Similarity	NPD6641	Approved
0.6773	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD2307	Discontinued
0.677	Remote Similarity	NPD7562	Approved
0.6767	Remote Similarity	NPD7878	Phase 2
0.6759	Remote Similarity	NPD6791	Phase 2
0.6756	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4889	Approved
0.6741	Remote Similarity	NPD7187	Phase 2
0.6736	Remote Similarity	NPD8409	Suspended
0.6736	Remote Similarity	NPD6962	Phase 2
0.6735	Remote Similarity	NPD107	Approved
0.6732	Remote Similarity	NPD2511	Approved
0.6726	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7417	Discontinued
0.6709	Remote Similarity	NPD8289	Discontinued
0.6706	Remote Similarity	NPD8091	Phase 3
0.6696	Remote Similarity	NPD5866	Approved
0.6695	Remote Similarity	NPD7395	Discontinued
0.6695	Remote Similarity	NPD5022	Discontinued
0.6682	Remote Similarity	NPD4948	Discontinued
0.6682	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6298	Discontinued
0.6681	Remote Similarity	NPD5901	Discontinued
0.668	Remote Similarity	NPD4373	Phase 2
0.6667	Remote Similarity	NPD7404	Approved
0.6653	Remote Similarity	NPD8356	Approved
0.6653	Remote Similarity	NPD6790	Phase 1
0.6652	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7470	Discontinued
0.6641	Remote Similarity	NPD8465	Approved
0.6641	Remote Similarity	NPD8467	Approved
0.6641	Remote Similarity	NPD8466	Approved
0.664	Remote Similarity	NPD7967	Discontinued
0.6636	Remote Similarity	NPD3921	Approved
0.6636	Remote Similarity	NPD3922	Approved
0.6636	Remote Similarity	NPD3924	Approved
0.6636	Remote Similarity	NPD3923	Approved
0.6633	Remote Similarity	NPD2896	Discontinued
0.6627	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3006	Discontinued
0.6626	Remote Similarity	NPD8412	Phase 1
0.6624	Remote Similarity	NPD1926	Approved
0.6622	Remote Similarity	NPD6226	Phase 3
0.6609	Remote Similarity	NPD5490	Discontinued
0.6608	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8021	Approved
0.6606	Remote Similarity	NPD4528	Approved
0.6606	Remote Similarity	NPD4529	Approved
0.6606	Remote Similarity	NPD4526	Approved
0.6606	Remote Similarity	NPD8020	Approved
0.66	Remote Similarity	NPD5482	Discontinued
0.6598	Remote Similarity	NPD5805	Approved
0.6596	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7467	Discontinued
0.6594	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.659	Remote Similarity	NPD8407	Phase 2
0.6581	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6479	Discontinued
0.6571	Remote Similarity	NPD6825	Phase 1
0.6569	Remote Similarity	NPD7426	Phase 1
0.6567	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4897	Phase 2
0.6562	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4375	Approved
0.6556	Remote Similarity	NPD4952	Phase 3
0.6553	Remote Similarity	NPD2581	Approved
0.6553	Remote Similarity	NPD2582	Approved
0.655	Remote Similarity	NPD3371	Approved
0.655	Remote Similarity	NPD5429	Discontinued
0.6545	Remote Similarity	NPD6281	Approved
0.6542	Remote Similarity	NPD8430	Approved
0.6541	Remote Similarity	NPD8425	Approved
0.6541	Remote Similarity	NPD8459	Approved
0.6541	Remote Similarity	NPD8426	Approved
0.6541	Remote Similarity	NPD8460	Approved
0.654	Remote Similarity	NPD5507	Approved
0.654	Remote Similarity	NPD5147	Discontinued
0.654	Remote Similarity	NPD5506	Approved
0.6537	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1270	Approved
0.6533	Remote Similarity	NPD6874	Approved
0.6532	Remote Similarity	NPD4551	Phase 2
0.6529	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD8368	Discontinued
0.6528	Remote Similarity	NPD3386	Phase 2
0.6524	Remote Similarity	NPD6446	Discontinued
0.6522	Remote Similarity	NPD7191	Phase 2
0.652	Remote Similarity	NPD6276	Discontinued
0.6518	Remote Similarity	NPD6206	Phase 1
0.6518	Remote Similarity	NPD5003	Discontinued
0.6515	Remote Similarity	NPD8427	Approved
0.6515	Remote Similarity	NPD8428	Approved
0.6515	Remote Similarity	NPD8429	Approved
0.6512	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD8404	Phase 2
0.6509	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7957	Phase 1
0.6507	Remote Similarity	NPD7001	Phase 3
0.6506	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD4600	Approved
0.6504	Remote Similarity	NPD4601	Approved
0.6504	Remote Similarity	NPD6219	Discontinued
0.6496	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6716	Phase 1
0.6491	Remote Similarity	NPD6176	Phase 1
0.6491	Remote Similarity	NPD5513	Phase 2
0.6486	Remote Similarity	NPD6665	Discontinued
0.6486	Remote Similarity	NPD6569	Phase 2
0.6483	Remote Similarity	NPD3354	Phase 2
0.6483	Remote Similarity	NPD4429	Discontinued
0.6481	Remote Similarity	NPD3816	Phase 1

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