NPASS Compound

Structure

NPC88744 OpenBabel07101718182D 45 50 0 0 1 0 0 0 0 0999 V2000 -1.5489 -4.5807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2869 -3.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0373 2.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0569 2.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8769 -3.0222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2757 -2.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2459 -3.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9019 -2.9198 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8490 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7924 0.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6981 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3962 0.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6981 -1.9608 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7924 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9433 -0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0943 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8490 -0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0943 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1234 -0.6774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8490 -0.4902 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 -2.5471 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4904 0.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 -0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 -0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7246 0.2182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0984 -0.7799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 6 34 1 0 0 0 0 8 13 1 0 0 0 0 8 19 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 33 1 0 0 0 0 12 35 1 0 0 0 0 13 36 1 0 0 0 0 14 15 1 0 0 0 0 14 34 1 0 0 0 0 15 36 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 37 1 0 0 0 0 19 18 1 6 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 20 34 1 6 0 0 0 21 29 1 0 0 0 0 21 38 1 6 0 0 0 22 17 1 6 0 0 0 22 26 1 0 0 0 0 22 44 1 0 0 0 0 23 32 1 0 0 0 0 23 33 1 1 0 0 0 24 32 1 0 0 0 0 24 45 1 6 0 0 0 25 36 1 1 0 0 0 26 27 1 0 0 0 0 26 39 1 1 0 0 0 27 28 1 0 0 0 0 27 40 1 6 0 0 0 28 30 1 0 0 0 0 28 41 1 1 0 0 0 29 33 1 1 0 0 0 29 35 1 0 0 0 0 30 44 1 0 0 0 0 30 45 1 6 0 0 0 31 42 2 0 0 0 0 31 43 1 0 0 0 0 33 5 1 1 0 0 0 34 35 1 1 0 0 0 35 7 1 1 0 0 0 36 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.41
Volume:	653.712
LogP:	3.54
LogD:	3.937
LogS:	-3.26
# Rotatable Bonds:	5
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.195
Synthetic Accessibility Score:	5.412
Fsp3:	0.917
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:	-5.791
MDCK Permeability:	1.2335912288108375e-05
Pgp-inhibitor:	0.09
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.137
20% Bioavailability (F20%):	0.58
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	82.75897216796875%
Volume Distribution (VD):	0.497
Pgp-substrate:	6.978727340698242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.353
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.774
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	0.997
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.089
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.749

Download Data

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

Natural Product: NPC88744

Natural Product ID:	NPC88744
*Common Name:**	3-O-Beta-D-Glucopyranosyl 3Alpha,11Alpha-Dihydroxylup-20(29)-En-28-Oic Acid
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,9R,11aS,11bR,12R,13aR,13bR)-12-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:
Standard InCHIKey:	WRJZIYSNFOGUAQ-ZEJDLYSXSA-N
Standard InCHI:	InChI=1S/C36H58O9/c1-18(2)19-8-13-36(31(42)43)15-14-34(6)20(25(19)36)16-21(38)29-33(5)11-10-24(32(3,4)23(33)9-12-35(29,34)7)45-30-28(41)27(40)26(39)22(17-37)44-30/h19-30,37-41H,1,8-17H2,2-7H3,(H,42,43)/t19-,20+,21+,22+,23-,24+,25+,26+,27-,28+,29+,30-,33-,34+,35+,36-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3[C@H](O)C[C@H]3[C@@]2(C)CC[C@@]2([C@@H]3[C@@H](CC2)C(=C)C)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1269326
PubChem CID:	52949152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20621475]
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	steamed leaves	n.a.	n.a.	PMID[20932756]
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[504336]

☑ 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 NPC88744 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	272
0.1-0.2	2039
0.2-0.3	6391
0.3-0.4	13289
0.4-0.5	8113
0.5-0.6	5435
0.6-0.7	3744
0.7-0.8	2038
0.8-0.85	819
0.85-0.9	475
0.9-0.95	61
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC240125
0.99	High Similarity	NPC473844
0.99	High Similarity	NPC51947
0.99	High Similarity	NPC91583
0.9706	High Similarity	NPC11035
0.9706	High Similarity	NPC240734
0.9706	High Similarity	NPC204392
0.9706	High Similarity	NPC1876
0.9706	High Similarity	NPC91838
0.9706	High Similarity	NPC275668
0.9519	High Similarity	NPC146563
0.9495	High Similarity	NPC94919
0.9429	High Similarity	NPC469821
0.9423	High Similarity	NPC470543
0.934	High Similarity	NPC137414
0.934	High Similarity	NPC469820
0.934	High Similarity	NPC469823
0.9327	High Similarity	NPC272242
0.9314	High Similarity	NPC287269
0.9245	High Similarity	NPC54395
0.9238	High Similarity	NPC243572
0.9167	High Similarity	NPC469822
0.9151	High Similarity	NPC73986
0.9151	High Similarity	NPC102619
0.9143	High Similarity	NPC285410
0.9143	High Similarity	NPC263827
0.9143	High Similarity	NPC250481
0.9143	High Similarity	NPC274833
0.9135	High Similarity	NPC306746
0.9135	High Similarity	NPC204407
0.9135	High Similarity	NPC57362
0.9135	High Similarity	NPC8431
0.9135	High Similarity	NPC167383
0.9135	High Similarity	NPC237503
0.9074	High Similarity	NPC156651
0.9057	High Similarity	NPC472719
0.9057	High Similarity	NPC207845
0.9057	High Similarity	NPC233003
0.9048	High Similarity	NPC174679
0.9048	High Similarity	NPC29069
0.9048	High Similarity	NPC56713
0.9048	High Similarity	NPC136877
0.9048	High Similarity	NPC108709
0.9048	High Similarity	NPC68419
0.9048	High Similarity	NPC7870
0.9048	High Similarity	NPC110139
0.9048	High Similarity	NPC475296
0.9048	High Similarity	NPC274507
0.9048	High Similarity	NPC474589
0.9048	High Similarity	NPC129340
0.9048	High Similarity	NPC476882
0.9048	High Similarity	NPC476883
0.9048	High Similarity	NPC476887
0.9048	High Similarity	NPC90856
0.9048	High Similarity	NPC476880
0.9048	High Similarity	NPC476885
0.9048	High Similarity	NPC164194
0.9048	High Similarity	NPC270667
0.9048	High Similarity	NPC279554
0.9048	High Similarity	NPC102914
0.9048	High Similarity	NPC476886
0.9048	High Similarity	NPC199457
0.9048	High Similarity	NPC476884
0.9048	High Similarity	NPC75747
0.9048	High Similarity	NPC127056
0.9048	High Similarity	NPC59804
0.9048	High Similarity	NPC476881
0.9038	High Similarity	NPC28198
0.9038	High Similarity	NPC224414
0.9038	High Similarity	NPC476123
0.9038	High Similarity	NPC284807
0.9038	High Similarity	NPC195708
0.9038	High Similarity	NPC177246
0.8972	High Similarity	NPC251309
0.8962	High Similarity	NPC297208
0.8962	High Similarity	NPC30397
0.8962	High Similarity	NPC211798
0.8962	High Similarity	NPC235841
0.8962	High Similarity	NPC108748
0.8962	High Similarity	NPC164419
0.8962	High Similarity	NPC191763
0.8962	High Similarity	NPC473481
0.8962	High Similarity	NPC31839
0.8962	High Similarity	NPC179434
0.8952	High Similarity	NPC127853
0.8952	High Similarity	NPC265655
0.8952	High Similarity	NPC137917
0.8942	High Similarity	NPC283849
0.8942	High Similarity	NPC234160
0.8942	High Similarity	NPC473538
0.8919	High Similarity	NPC470478
0.8889	High Similarity	NPC473882
0.8879	High Similarity	NPC37739
0.8879	High Similarity	NPC292677
0.8879	High Similarity	NPC104400
0.8879	High Similarity	NPC471383
0.8879	High Similarity	NPC257468
0.8879	High Similarity	NPC101744
0.8879	High Similarity	NPC475504
0.8879	High Similarity	NPC116794
0.8879	High Similarity	NPC79718
0.8879	High Similarity	NPC104071
0.8879	High Similarity	NPC80843
0.8879	High Similarity	NPC471967
0.8879	High Similarity	NPC109079
0.8879	High Similarity	NPC102439
0.8879	High Similarity	NPC469946
0.8879	High Similarity	NPC48249
0.8879	High Similarity	NPC473373
0.8879	High Similarity	NPC1046
0.8879	High Similarity	NPC324875
0.8879	High Similarity	NPC473383
0.8879	High Similarity	NPC10320
0.8879	High Similarity	NPC139894
0.8879	High Similarity	NPC128925
0.8879	High Similarity	NPC276093
0.8879	High Similarity	NPC256798
0.8879	High Similarity	NPC46388
0.8879	High Similarity	NPC477253
0.8879	High Similarity	NPC475516
0.8879	High Similarity	NPC139044
0.8868	High Similarity	NPC220984
0.8868	High Similarity	NPC106760
0.8868	High Similarity	NPC242611
0.8868	High Similarity	NPC78046
0.8868	High Similarity	NPC269095
0.8857	High Similarity	NPC472988
0.8857	High Similarity	NPC295389
0.8857	High Similarity	NPC38217
0.8857	High Similarity	NPC230888
0.8857	High Similarity	NPC285576
0.8846	High Similarity	NPC473199
0.8846	High Similarity	NPC475611
0.8846	High Similarity	NPC165405
0.8818	High Similarity	NPC239293
0.8812	High Similarity	NPC157739
0.8807	High Similarity	NPC472718
0.8807	High Similarity	NPC244127
0.88	High Similarity	NPC472989
0.8796	High Similarity	NPC155410
0.8796	High Similarity	NPC47063
0.8796	High Similarity	NPC114287
0.8796	High Similarity	NPC73318
0.8796	High Similarity	NPC309714
0.8796	High Similarity	NPC163183
0.8796	High Similarity	NPC473343
0.8796	High Similarity	NPC138334
0.8796	High Similarity	NPC96641
0.8796	High Similarity	NPC151543
0.8796	High Similarity	NPC166422
0.8796	High Similarity	NPC271138
0.8796	High Similarity	NPC258885
0.8796	High Similarity	NPC133818
0.8796	High Similarity	NPC189884
0.8796	High Similarity	NPC323341
0.8796	High Similarity	NPC192600
0.8796	High Similarity	NPC475467
0.8796	High Similarity	NPC219180
0.8796	High Similarity	NPC150400
0.8796	High Similarity	NPC124296
0.8796	High Similarity	NPC114304
0.8796	High Similarity	NPC241909
0.8796	High Similarity	NPC238935
0.8796	High Similarity	NPC134835
0.8796	High Similarity	NPC475287
0.8796	High Similarity	NPC204458
0.8796	High Similarity	NPC46665
0.8796	High Similarity	NPC269315
0.8796	High Similarity	NPC174720
0.8796	High Similarity	NPC475208
0.8796	High Similarity	NPC251263
0.8796	High Similarity	NPC473826
0.8796	High Similarity	NPC295823
0.8785	High Similarity	NPC292196
0.8785	High Similarity	NPC477073
0.8774	High Similarity	NPC125361
0.8774	High Similarity	NPC477070
0.8774	High Similarity	NPC154085
0.8774	High Similarity	NPC477069
0.8774	High Similarity	NPC51925
0.8774	High Similarity	NPC43976
0.8774	High Similarity	NPC296761
0.875	High Similarity	NPC469827
0.8725	High Similarity	NPC317019
0.8716	High Similarity	NPC119592
0.8716	High Similarity	NPC164389
0.8716	High Similarity	NPC204414
0.8716	High Similarity	NPC79643
0.8716	High Similarity	NPC293330
0.8716	High Similarity	NPC71065
0.8716	High Similarity	NPC476068
0.8716	High Similarity	NPC471385
0.8716	High Similarity	NPC202828
0.8716	High Similarity	NPC261506
0.8716	High Similarity	NPC475160
0.8716	High Similarity	NPC294453
0.8716	High Similarity	NPC475486
0.8716	High Similarity	NPC298034
0.8716	High Similarity	NPC224381
0.8716	High Similarity	NPC305981

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 NPC88744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	2419
0.2-0.3	3990
0.3-0.4	1591
0.4-0.5	423
0.5-0.6	273
0.6-0.7	144
0.7-0.8	28
0.8-0.85	14
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8972	High Similarity	NPD8133	Approved
0.8426	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD8034	Phase 2
0.8218	Intermediate Similarity	NPD8035	Phase 2
0.8136	Intermediate Similarity	NPD7507	Approved
0.812	Intermediate Similarity	NPD8328	Phase 3
0.8073	Intermediate Similarity	NPD6412	Phase 2
0.8056	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD8377	Approved
0.8017	Intermediate Similarity	NPD8294	Approved
0.798	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD8033	Approved
0.7949	Intermediate Similarity	NPD8335	Approved
0.7949	Intermediate Similarity	NPD8380	Approved
0.7949	Intermediate Similarity	NPD8379	Approved
0.7949	Intermediate Similarity	NPD8296	Approved
0.7949	Intermediate Similarity	NPD8378	Approved
0.7934	Intermediate Similarity	NPD7319	Approved
0.7845	Intermediate Similarity	NPD7328	Approved
0.7845	Intermediate Similarity	NPD7327	Approved
0.7838	Intermediate Similarity	NPD6686	Approved
0.7778	Intermediate Similarity	NPD7516	Approved
0.7705	Intermediate Similarity	NPD7736	Approved
0.7619	Intermediate Similarity	NPD8171	Discontinued
0.75	Intermediate Similarity	NPD7503	Approved
0.748	Intermediate Similarity	NPD8293	Discontinued
0.7383	Intermediate Similarity	NPD7748	Approved
0.7339	Intermediate Similarity	NPD7902	Approved
0.7295	Intermediate Similarity	NPD6370	Approved
0.7273	Intermediate Similarity	NPD6114	Approved
0.7273	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6118	Approved
0.7273	Intermediate Similarity	NPD6115	Approved
0.7273	Intermediate Similarity	NPD7638	Approved
0.7265	Intermediate Similarity	NPD6882	Approved
0.7265	Intermediate Similarity	NPD8297	Approved
0.7227	Intermediate Similarity	NPD6940	Discontinued
0.7207	Intermediate Similarity	NPD7640	Approved
0.7207	Intermediate Similarity	NPD7639	Approved
0.7196	Intermediate Similarity	NPD7515	Phase 2
0.7177	Intermediate Similarity	NPD7492	Approved
0.7172	Intermediate Similarity	NPD6116	Phase 1
0.7167	Intermediate Similarity	NPD6009	Approved
0.7131	Intermediate Similarity	NPD6319	Approved
0.7131	Intermediate Similarity	NPD6059	Approved
0.7131	Intermediate Similarity	NPD6054	Approved
0.713	Intermediate Similarity	NPD6399	Phase 3
0.712	Intermediate Similarity	NPD6616	Approved
0.7073	Intermediate Similarity	NPD8513	Phase 3
0.7073	Intermediate Similarity	NPD8516	Approved
0.7073	Intermediate Similarity	NPD8515	Approved
0.7073	Intermediate Similarity	NPD8517	Approved
0.7071	Intermediate Similarity	NPD6117	Approved
0.7069	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7900	Approved
0.7064	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7078	Approved
0.7059	Intermediate Similarity	NPD4632	Approved
0.7043	Intermediate Similarity	NPD6675	Approved
0.7043	Intermediate Similarity	NPD6402	Approved
0.7043	Intermediate Similarity	NPD7128	Approved
0.7043	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD6373	Approved
0.696	Remote Similarity	NPD6067	Discontinued
0.6935	Remote Similarity	NPD6016	Approved
0.6935	Remote Similarity	NPD6015	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6891	Remote Similarity	NPD6649	Approved
0.6891	Remote Similarity	NPD6650	Approved
0.6891	Remote Similarity	NPD8130	Phase 1
0.6885	Remote Similarity	NPD7115	Discovery
0.688	Remote Similarity	NPD5988	Approved
0.6869	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5701	Approved
0.6838	Remote Similarity	NPD5697	Approved
0.6807	Remote Similarity	NPD6883	Approved
0.6807	Remote Similarity	NPD7102	Approved
0.6807	Remote Similarity	NPD7290	Approved
0.6796	Remote Similarity	NPD6928	Phase 2
0.6783	Remote Similarity	NPD7632	Discontinued
0.675	Remote Similarity	NPD6847	Approved
0.675	Remote Similarity	NPD6617	Approved
0.675	Remote Similarity	NPD6869	Approved
0.675	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6084	Phase 2
0.6726	Remote Similarity	NPD6083	Phase 2
0.6723	Remote Similarity	NPD6014	Approved
0.6723	Remote Similarity	NPD6013	Approved
0.6723	Remote Similarity	NPD6012	Approved
0.6698	Remote Similarity	NPD4786	Approved
0.6697	Remote Similarity	NPD5328	Approved
0.6693	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD6011	Approved
0.6635	Remote Similarity	NPD7525	Registered
0.6615	Remote Similarity	NPD6033	Approved
0.6612	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6008	Approved
0.6606	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3669	Approved
0.6604	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4788	Approved
0.6589	Remote Similarity	NPD6336	Discontinued
0.6579	Remote Similarity	NPD4755	Approved
0.6577	Remote Similarity	NPD6079	Approved
0.6574	Remote Similarity	NPD3618	Phase 1
0.6538	Remote Similarity	NPD7645	Phase 2
0.6535	Remote Similarity	NPD6921	Approved
0.6529	Remote Similarity	NPD4634	Approved
0.6518	Remote Similarity	NPD4202	Approved
0.6509	Remote Similarity	NPD3667	Approved
0.65	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3703	Phase 2
0.6466	Remote Similarity	NPD4700	Approved
0.6466	Remote Similarity	NPD4696	Approved
0.6466	Remote Similarity	NPD5285	Approved
0.6466	Remote Similarity	NPD5286	Approved
0.6455	Remote Similarity	NPD5737	Approved
0.6455	Remote Similarity	NPD6672	Approved
0.6422	Remote Similarity	NPD6684	Approved
0.6422	Remote Similarity	NPD6409	Approved
0.6422	Remote Similarity	NPD7521	Approved
0.6422	Remote Similarity	NPD5330	Approved
0.6422	Remote Similarity	NPD7334	Approved
0.6422	Remote Similarity	NPD7146	Approved
0.6418	Remote Similarity	NPD8449	Approved
0.6417	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1779	Approved
0.6415	Remote Similarity	NPD1780	Approved
0.6408	Remote Similarity	NPD7625	Phase 1
0.6404	Remote Similarity	NPD5695	Phase 3
0.64	Remote Similarity	NPD6274	Approved
0.6379	Remote Similarity	NPD5696	Approved
0.6379	Remote Similarity	NPD4225	Approved
0.6378	Remote Similarity	NPD7100	Approved
0.6378	Remote Similarity	NPD7101	Approved
0.637	Remote Similarity	NPD8450	Suspended
0.6356	Remote Similarity	NPD5225	Approved
0.6356	Remote Similarity	NPD5224	Approved
0.6356	Remote Similarity	NPD5211	Phase 2
0.6356	Remote Similarity	NPD5226	Approved
0.6356	Remote Similarity	NPD4633	Approved
0.6348	Remote Similarity	NPD4697	Phase 3
0.6348	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5222	Approved
0.6348	Remote Similarity	NPD5221	Approved
0.6339	Remote Similarity	NPD6698	Approved
0.6339	Remote Similarity	NPD46	Approved
0.6333	Remote Similarity	NPD4768	Approved
0.6333	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD3702	Approved
0.6306	Remote Similarity	NPD6903	Approved
0.6303	Remote Similarity	NPD5174	Approved
0.6303	Remote Similarity	NPD5175	Approved
0.63	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6335	Approved
0.6293	Remote Similarity	NPD5173	Approved
0.6288	Remote Similarity	NPD8074	Phase 3
0.6283	Remote Similarity	NPD6411	Approved
0.6283	Remote Similarity	NPD7637	Suspended
0.6279	Remote Similarity	NPD6909	Approved
0.6279	Remote Similarity	NPD6908	Approved
0.6271	Remote Similarity	NPD5223	Approved
0.627	Remote Similarity	NPD6868	Approved
0.6261	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD5141	Approved
0.6241	Remote Similarity	NPD8336	Approved
0.6241	Remote Similarity	NPD8337	Approved
0.6239	Remote Similarity	NPD3133	Approved
0.6239	Remote Similarity	NPD3666	Approved
0.6239	Remote Similarity	NPD3665	Phase 1
0.623	Remote Similarity	NPD4730	Approved
0.623	Remote Similarity	NPD4729	Approved
0.622	Remote Similarity	NPD6317	Approved
0.6216	Remote Similarity	NPD7524	Approved
0.6186	Remote Similarity	NPD8418	Phase 2
0.6176	Remote Similarity	NPD5777	Approved
0.6176	Remote Similarity	NPD6081	Approved
0.6176	Remote Similarity	NPD8338	Approved
0.6172	Remote Similarity	NPD6313	Approved
0.6172	Remote Similarity	NPD6314	Approved
0.6167	Remote Similarity	NPD4754	Approved
0.616	Remote Similarity	NPD6053	Discontinued
0.6148	Remote Similarity	NPD5956	Approved
0.614	Remote Similarity	NPD7983	Approved
0.6129	Remote Similarity	NPD5249	Phase 3
0.6129	Remote Similarity	NPD5247	Approved
0.6129	Remote Similarity	NPD5250	Approved
0.6129	Remote Similarity	NPD5248	Approved
0.6129	Remote Similarity	NPD5251	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