NPASS Compound

Structure

NPC471966 OpenBabel07101718222D 37 41 0 0 1 0 0 0 0 0999 V2000 -5.0724 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0481 -2.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0243 -2.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0481 4.2621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0243 4.2621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 1.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3816 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3816 1.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 3.4167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6908 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 5.1075 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9178 1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 -1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 7 31 1 0 0 0 0 9 12 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 30 1 0 0 0 0 12 32 1 0 0 0 0 13 14 1 0 0 0 0 13 29 1 0 0 0 0 14 31 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 16 28 1 0 0 0 0 17 25 1 0 0 0 0 17 28 1 0 0 0 0 18 28 1 0 0 0 0 18 33 2 0 0 0 0 19 34 2 0 0 0 0 19 37 1 0 0 0 0 20 21 1 0 0 0 0 20 31 1 0 0 0 0 21 29 1 1 0 0 0 22 26 1 0 0 0 0 22 35 2 0 0 0 0 23 27 1 0 0 0 0 23 30 1 6 0 0 0 24 27 1 0 0 0 0 24 36 1 6 0 0 0 25 29 1 6 0 0 0 25 37 1 0 0 0 0 26 30 1 6 0 0 0 26 32 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 6 0 0 0 30 6 1 6 0 0 0 31 32 1 6 0 0 0 32 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.35
Volume:	552.651
LogP:	3.941
LogD:	3.498
LogS:	-4.62
# Rotatable Bonds:	3
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.27
Synthetic Accessibility Score:	5.277
Fsp3:	0.844
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152
MDCK Permeability:	2.04923653654987e-05
Pgp-inhibitor:	0.764
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	71.6922607421875%
Volume Distribution (VD):	1.505
Pgp-substrate:	19.730628967285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.786

ADMET: Excretion

Clearance (CL):	5.075
Half-life (T1/2):	0.435

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.761
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.917
Carcinogencity:	0.042
Eye Corrosion:	0.681
Eye Irritation:	0.148
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC471966

Natural Product ID:	NPC471966
*Common Name:**	UENSMJVQEAFMKY-YEIPECPNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UENSMJVQEAFMKY-YEIPECPNSA-N
Standard InCHI:	InChI=1S/C32H48O5/c1-19(34)37-25-17-28(4,18-33)16-21-20-15-22(35)26-30(6)11-10-24(36)27(2,3)23(30)9-12-32(26,8)31(20,7)14-13-29(21,25)5/h15,18,21,23-26,36H,9-14,16-17H2,1-8H3/t21-,23-,24-,25+,26+,28+,29+,30-,31+,32+/m0/s1
SMILES:	O=C[C@@]1(C)C[C@@H](OC(=O)C)[C@]2([C@@H](C1)C1=CC(=O)[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314505
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	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
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	69200.0	nM	PMID[524061]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[524061]

☑ 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 NPC471966 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	224
0.1-0.2	1396
0.2-0.3	4965
0.3-0.4	12129
0.4-0.5	10209
0.5-0.6	6078
0.6-0.7	4830
0.7-0.8	2374
0.8-0.85	216
0.85-0.9	218
0.9-0.95	56
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC74751
0.9451	High Similarity	NPC295643
0.9451	High Similarity	NPC214756
0.9451	High Similarity	NPC272075
0.9341	High Similarity	NPC158030
0.9341	High Similarity	NPC4036
0.9341	High Similarity	NPC233455
0.9341	High Similarity	NPC65120
0.9341	High Similarity	NPC145067
0.9255	High Similarity	NPC26413
0.9239	High Similarity	NPC86368
0.9231	High Similarity	NPC113989
0.9231	High Similarity	NPC120840
0.9231	High Similarity	NPC291028
0.9149	High Similarity	NPC98874
0.9149	High Similarity	NPC327179
0.913	High Similarity	NPC77099
0.913	High Similarity	NPC470590
0.913	High Similarity	NPC60755
0.913	High Similarity	NPC105189
0.913	High Similarity	NPC285184
0.9121	High Similarity	NPC30522
0.9043	High Similarity	NPC148523
0.9043	High Similarity	NPC139570
0.9043	High Similarity	NPC474727
0.9032	High Similarity	NPC298554
0.9032	High Similarity	NPC63118
0.9032	High Similarity	NPC474436
0.9032	High Similarity	NPC49776
0.9022	High Similarity	NPC290614
0.9022	High Similarity	NPC193750
0.9022	High Similarity	NPC477872
0.9022	High Similarity	NPC7260
0.9022	High Similarity	NPC210037
0.9022	High Similarity	NPC474728
0.9022	High Similarity	NPC227467
0.9022	High Similarity	NPC273621
0.9022	High Similarity	NPC18872
0.9022	High Similarity	NPC120968
0.9011	High Similarity	NPC40552
0.9011	High Similarity	NPC52169
0.9011	High Similarity	NPC182797
0.9011	High Similarity	NPC224145
0.9011	High Similarity	NPC246708
0.898	High Similarity	NPC282233
0.898	High Similarity	NPC95585
0.8958	High Similarity	NPC188833
0.8947	High Similarity	NPC230151
0.8936	High Similarity	NPC184006
0.8936	High Similarity	NPC23621
0.8936	High Similarity	NPC222047
0.8936	High Similarity	NPC296164
0.8936	High Similarity	NPC209868
0.8936	High Similarity	NPC78580
0.8925	High Similarity	NPC474525
0.8925	High Similarity	NPC187722
0.8925	High Similarity	NPC38754
0.8913	High Similarity	NPC130520
0.8913	High Similarity	NPC290972
0.8913	High Similarity	NPC263393
0.8913	High Similarity	NPC61543
0.8913	High Similarity	NPC64872
0.8913	High Similarity	NPC59263
0.8913	High Similarity	NPC198664
0.8913	High Similarity	NPC270768
0.8913	High Similarity	NPC121798
0.8913	High Similarity	NPC143232
0.8913	High Similarity	NPC225585
0.8913	High Similarity	NPC293048
0.8913	High Similarity	NPC470588
0.8913	High Similarity	NPC25906
0.8913	High Similarity	NPC274330
0.8913	High Similarity	NPC234346
0.8913	High Similarity	NPC127689
0.8901	High Similarity	NPC307426
0.8901	High Similarity	NPC293564
0.8901	High Similarity	NPC68160
0.8901	High Similarity	NPC171203
0.8901	High Similarity	NPC142415
0.8901	High Similarity	NPC88716
0.8901	High Similarity	NPC242468
0.8901	High Similarity	NPC162107
0.8901	High Similarity	NPC102683
0.8901	High Similarity	NPC98442
0.8901	High Similarity	NPC46912
0.8901	High Similarity	NPC130577
0.8901	High Similarity	NPC51700
0.8901	High Similarity	NPC18064
0.8878	High Similarity	NPC476890
0.8854	High Similarity	NPC476879
0.8854	High Similarity	NPC476878
0.8854	High Similarity	NPC187933
0.8854	High Similarity	NPC89225
0.8842	High Similarity	NPC195715
0.8842	High Similarity	NPC274417
0.8842	High Similarity	NPC23241
0.883	High Similarity	NPC158059
0.883	High Similarity	NPC307335
0.883	High Similarity	NPC118490
0.883	High Similarity	NPC229281
0.883	High Similarity	NPC74855
0.883	High Similarity	NPC202728
0.883	High Similarity	NPC136313
0.883	High Similarity	NPC118519
0.8817	High Similarity	NPC130278
0.8817	High Similarity	NPC470589
0.8817	High Similarity	NPC111110
0.8817	High Similarity	NPC46441
0.8817	High Similarity	NPC126369
0.8804	High Similarity	NPC474512
0.8804	High Similarity	NPC473242
0.8804	High Similarity	NPC181225
0.8804	High Similarity	NPC290690
0.8804	High Similarity	NPC17733
0.8804	High Similarity	NPC470629
0.8791	High Similarity	NPC9892
0.8791	High Similarity	NPC329943
0.8791	High Similarity	NPC74363
0.8791	High Similarity	NPC477579
0.8791	High Similarity	NPC325594
0.8791	High Similarity	NPC235341
0.8791	High Similarity	NPC10005
0.8791	High Similarity	NPC475862
0.8791	High Similarity	NPC91525
0.8791	High Similarity	NPC95594
0.8791	High Similarity	NPC72638
0.8788	High Similarity	NPC476889
0.8776	High Similarity	NPC54909
0.8776	High Similarity	NPC93744
0.8776	High Similarity	NPC476888
0.8776	High Similarity	NPC233012
0.8763	High Similarity	NPC478056
0.8763	High Similarity	NPC164349
0.8763	High Similarity	NPC58942
0.8763	High Similarity	NPC260149
0.875	High Similarity	NPC157113
0.875	High Similarity	NPC167193
0.875	High Similarity	NPC62516
0.875	High Similarity	NPC472806
0.8737	High Similarity	NPC269729
0.8737	High Similarity	NPC6818
0.8737	High Similarity	NPC191412
0.8737	High Similarity	NPC114159
0.8737	High Similarity	NPC91010
0.8737	High Similarity	NPC474529
0.8725	High Similarity	NPC310546
0.8723	High Similarity	NPC25299
0.8723	High Similarity	NPC471588
0.8723	High Similarity	NPC155120
0.8723	High Similarity	NPC235884
0.8723	High Similarity	NPC71074
0.8723	High Similarity	NPC282616
0.8723	High Similarity	NPC6255
0.8723	High Similarity	NPC300351
0.8723	High Similarity	NPC228784
0.8723	High Similarity	NPC52021
0.8723	High Similarity	NPC472149
0.8723	High Similarity	NPC324341
0.8723	High Similarity	NPC84319
0.8723	High Similarity	NPC306541
0.8723	High Similarity	NPC966
0.8723	High Similarity	NPC288833
0.871	High Similarity	NPC161751
0.871	High Similarity	NPC474972
0.871	High Similarity	NPC95246
0.871	High Similarity	NPC475049
0.8696	High Similarity	NPC73064
0.8687	High Similarity	NPC40918
0.8681	High Similarity	NPC133954
0.8681	High Similarity	NPC191965
0.8673	High Similarity	NPC475202
0.8673	High Similarity	NPC475385
0.8673	High Similarity	NPC475392
0.866	High Similarity	NPC259788
0.866	High Similarity	NPC158347
0.866	High Similarity	NPC255589
0.866	High Similarity	NPC473456
0.8646	High Similarity	NPC96916
0.8632	High Similarity	NPC169343
0.8632	High Similarity	NPC275809
0.8617	High Similarity	NPC86372
0.8617	High Similarity	NPC172361
0.8617	High Similarity	NPC49320
0.8617	High Similarity	NPC328141
0.8602	High Similarity	NPC472802
0.8602	High Similarity	NPC473229
0.8602	High Similarity	NPC474474
0.8602	High Similarity	NPC206060
0.8602	High Similarity	NPC474845
0.86	High Similarity	NPC478057
0.8587	High Similarity	NPC84121
0.8587	High Similarity	NPC73038
0.8587	High Similarity	NPC137306
0.8587	High Similarity	NPC213412
0.8571	High Similarity	NPC194196
0.8571	High Similarity	NPC96095
0.8557	High Similarity	NPC471039
0.8557	High Similarity	NPC73004
0.8557	High Similarity	NPC173744
0.8557	High Similarity	NPC207922

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 NPC471966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1716
0.2-0.3	3838
0.3-0.4	2272
0.4-0.5	668
0.5-0.6	209
0.6-0.7	170
0.7-0.8	73
0.8-0.85	1
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.956	High Similarity	NPD7748	Approved
0.9462	High Similarity	NPD7902	Approved
0.9341	High Similarity	NPD7515	Phase 2
0.914	High Similarity	NPD7901	Clinical (unspecified phase)
0.914	High Similarity	NPD7900	Approved
0.8191	Intermediate Similarity	NPD3618	Phase 1
0.8144	Intermediate Similarity	NPD8034	Phase 2
0.8144	Intermediate Similarity	NPD8035	Phase 2
0.8061	Intermediate Similarity	NPD6399	Phase 3
0.8021	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4697	Phase 3
0.7938	Intermediate Similarity	NPD5328	Approved
0.7905	Intermediate Similarity	NPD5739	Approved
0.7905	Intermediate Similarity	NPD6675	Approved
0.7905	Intermediate Similarity	NPD6402	Approved
0.7905	Intermediate Similarity	NPD7128	Approved
0.7895	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD6373	Approved
0.785	Intermediate Similarity	NPD6372	Approved
0.7843	Intermediate Similarity	NPD7638	Approved
0.7826	Intermediate Similarity	NPD7645	Phase 2
0.7812	Intermediate Similarity	NPD6409	Approved
0.7812	Intermediate Similarity	NPD7146	Approved
0.7812	Intermediate Similarity	NPD5330	Approved
0.7812	Intermediate Similarity	NPD6684	Approved
0.7812	Intermediate Similarity	NPD7334	Approved
0.7812	Intermediate Similarity	NPD7521	Approved
0.7778	Intermediate Similarity	NPD6079	Approved
0.7767	Intermediate Similarity	NPD7640	Approved
0.7767	Intermediate Similarity	NPD7639	Approved
0.7757	Intermediate Similarity	NPD6899	Approved
0.7757	Intermediate Similarity	NPD7320	Approved
0.7757	Intermediate Similarity	NPD6881	Approved
0.7755	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6084	Phase 2
0.7745	Intermediate Similarity	NPD6083	Phase 2
0.7739	Intermediate Similarity	NPD8328	Phase 3
0.7732	Intermediate Similarity	NPD3573	Approved
0.7706	Intermediate Similarity	NPD8130	Phase 1
0.7706	Intermediate Similarity	NPD6649	Approved
0.7706	Intermediate Similarity	NPD6650	Approved
0.7664	Intermediate Similarity	NPD5697	Approved
0.7664	Intermediate Similarity	NPD5701	Approved
0.7653	Intermediate Similarity	NPD5737	Approved
0.7653	Intermediate Similarity	NPD6903	Approved
0.7653	Intermediate Similarity	NPD6672	Approved
0.7636	Intermediate Similarity	NPD8297	Approved
0.7615	Intermediate Similarity	NPD6883	Approved
0.7615	Intermediate Similarity	NPD7290	Approved
0.7615	Intermediate Similarity	NPD7102	Approved
0.7604	Intermediate Similarity	NPD4786	Approved
0.7604	Intermediate Similarity	NPD3666	Approved
0.7604	Intermediate Similarity	NPD3665	Phase 1
0.7604	Intermediate Similarity	NPD3133	Approved
0.7593	Intermediate Similarity	NPD6011	Approved
0.7579	Intermediate Similarity	NPD3667	Approved
0.7549	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6617	Approved
0.7545	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6869	Approved
0.7545	Intermediate Similarity	NPD6847	Approved
0.7525	Intermediate Similarity	NPD4202	Approved
0.7523	Intermediate Similarity	NPD6013	Approved
0.7523	Intermediate Similarity	NPD6012	Approved
0.7523	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6014	Approved
0.7522	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD5696	Approved
0.7477	Intermediate Similarity	NPD6882	Approved
0.7476	Intermediate Similarity	NPD5221	Approved
0.7476	Intermediate Similarity	NPD5222	Approved
0.7476	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5173	Approved
0.7404	Intermediate Similarity	NPD4755	Approved
0.7379	Intermediate Similarity	NPD5695	Phase 3
0.7308	Intermediate Similarity	NPD7614	Phase 1
0.7308	Intermediate Similarity	NPD7732	Phase 3
0.7281	Intermediate Similarity	NPD6868	Approved
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5286	Approved
0.7264	Intermediate Similarity	NPD4696	Approved
0.7264	Intermediate Similarity	NPD5285	Approved
0.7264	Intermediate Similarity	NPD4700	Approved
0.7255	Intermediate Similarity	NPD6411	Approved
0.7248	Intermediate Similarity	NPD6008	Approved
0.7228	Intermediate Similarity	NPD6904	Approved
0.7228	Intermediate Similarity	NPD6673	Approved
0.7228	Intermediate Similarity	NPD6080	Approved
0.7228	Intermediate Similarity	NPD4753	Phase 2
0.7217	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5223	Approved
0.7188	Intermediate Similarity	NPD4695	Discontinued
0.7182	Intermediate Similarity	NPD6412	Phase 2
0.7172	Intermediate Similarity	NPD1694	Approved
0.717	Intermediate Similarity	NPD4225	Approved
0.7155	Intermediate Similarity	NPD6335	Approved
0.713	Intermediate Similarity	NPD5225	Approved
0.713	Intermediate Similarity	NPD5226	Approved
0.713	Intermediate Similarity	NPD4633	Approved
0.713	Intermediate Similarity	NPD7632	Discontinued
0.713	Intermediate Similarity	NPD6274	Approved
0.713	Intermediate Similarity	NPD5211	Phase 2
0.713	Intermediate Similarity	NPD5224	Approved
0.7115	Intermediate Similarity	NPD6001	Approved
0.7105	Intermediate Similarity	NPD4632	Approved
0.71	Intermediate Similarity	NPD5279	Phase 3
0.7094	Intermediate Similarity	NPD7101	Approved
0.7094	Intermediate Similarity	NPD7100	Approved
0.7087	Intermediate Similarity	NPD5284	Approved
0.7087	Intermediate Similarity	NPD5281	Approved
0.7071	Intermediate Similarity	NPD3668	Phase 3
0.7069	Intermediate Similarity	NPD6317	Approved
0.7064	Intermediate Similarity	NPD5174	Approved
0.7064	Intermediate Similarity	NPD4754	Approved
0.7064	Intermediate Similarity	NPD5175	Approved
0.7059	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6101	Approved
0.7049	Intermediate Similarity	NPD7736	Approved
0.7048	Intermediate Similarity	NPD4629	Approved
0.7048	Intermediate Similarity	NPD5210	Approved
0.7041	Intermediate Similarity	NPD4223	Phase 3
0.7041	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4221	Approved
0.7025	Intermediate Similarity	NPD7507	Approved
0.701	Intermediate Similarity	NPD7525	Registered
0.7009	Intermediate Similarity	NPD6314	Approved
0.7009	Intermediate Similarity	NPD6313	Approved
0.7	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD5141	Approved
0.6975	Remote Similarity	NPD6909	Approved
0.6975	Remote Similarity	NPD6908	Approved
0.6975	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5208	Approved
0.6947	Remote Similarity	NPD6117	Approved
0.6937	Remote Similarity	NPD4768	Approved
0.6937	Remote Similarity	NPD4767	Approved
0.6931	Remote Similarity	NPD6098	Approved
0.6923	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD6050	Approved
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4197	Approved
0.6891	Remote Similarity	NPD6319	Approved
0.6875	Remote Similarity	NPD6116	Phase 1
0.686	Remote Similarity	NPD7604	Phase 2
0.6855	Remote Similarity	NPD7319	Approved
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5983	Phase 2
0.6829	Remote Similarity	NPD8293	Discontinued
0.6827	Remote Similarity	NPD5692	Phase 3
0.6827	Remote Similarity	NPD5207	Approved
0.6814	Remote Similarity	NPD4730	Approved
0.6814	Remote Similarity	NPD5128	Approved
0.6814	Remote Similarity	NPD5168	Approved
0.6814	Remote Similarity	NPD6686	Approved
0.6814	Remote Similarity	NPD4729	Approved
0.6804	Remote Similarity	NPD6114	Approved
0.6804	Remote Similarity	NPD6697	Approved
0.6804	Remote Similarity	NPD6118	Approved
0.6804	Remote Similarity	NPD6115	Approved
0.6804	Remote Similarity	NPD3617	Approved
0.6803	Remote Similarity	NPD7492	Approved
0.68	Remote Similarity	NPD4788	Approved
0.6765	Remote Similarity	NPD4623	Approved
0.6765	Remote Similarity	NPD4690	Approved
0.6765	Remote Similarity	NPD4519	Discontinued
0.6765	Remote Similarity	NPD4689	Approved
0.6765	Remote Similarity	NPD5205	Approved
0.6765	Remote Similarity	NPD4693	Phase 3
0.6765	Remote Similarity	NPD4138	Approved
0.6765	Remote Similarity	NPD4688	Approved
0.6762	Remote Similarity	NPD5694	Approved
0.675	Remote Similarity	NPD6059	Approved
0.675	Remote Similarity	NPD6054	Approved
0.6748	Remote Similarity	NPD6336	Discontinued
0.6748	Remote Similarity	NPD6616	Approved
0.6737	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD5251	Approved
0.6696	Remote Similarity	NPD5248	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6696	Remote Similarity	NPD5247	Approved
0.6696	Remote Similarity	NPD5250	Approved
0.6696	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5249	Phase 3
0.6696	Remote Similarity	NPD5135	Approved
0.6696	Remote Similarity	NPD5169	Approved
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6638	Remote Similarity	NPD5216	Approved
0.6638	Remote Similarity	NPD5217	Approved
0.6638	Remote Similarity	NPD5127	Approved
0.6638	Remote Similarity	NPD5215	Approved
0.6612	Remote Similarity	NPD8377	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