NPASS Compound

Structure

NPC57362 OpenBabel07101718182D 45 50 0 0 1 0 0 0 0 0999 V2000 -2.5471 -4.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -3.4314 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 3.0373 2.3196 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 -0.0000 -1.9608 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 -2.9412 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 -3.3962 -1.9608 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 7.6414 1.4706 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 -2.5471 -3.4314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6981 -2.9412 0.0000 C 0 0 1 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 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 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 3.3962 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6981 -1.9608 0.0000 C 0 0 1 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 5.0943 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 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 2.5471 1.4706 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 2.5471 3.1687 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 -3.3962 0.0000 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 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 5 34 1 0 0 0 0 7 8 1 0 0 0 0 7 21 2 0 0 0 0 8 24 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 32 1 0 0 0 0 13 35 1 0 0 0 0 14 36 1 0 0 0 0 15 16 1 0 0 0 0 15 34 1 0 0 0 0 16 36 1 0 0 0 0 17 37 1 0 0 0 0 18 33 1 0 0 0 0 18 38 1 0 0 0 0 19 1 1 6 0 0 0 19 20 1 0 0 0 0 20 2 1 1 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 21 34 1 0 0 0 0 22 17 1 6 0 0 0 22 27 1 0 0 0 0 22 44 1 0 0 0 0 23 32 1 1 0 0 0 23 33 1 0 0 0 0 24 32 1 1 0 0 0 24 35 1 0 0 0 0 25 33 1 1 0 0 0 25 45 1 0 0 0 0 26 36 1 6 0 0 0 27 28 1 0 0 0 0 27 39 1 1 0 0 0 28 29 1 0 0 0 0 28 40 1 6 0 0 0 29 30 1 0 0 0 0 29 41 1 1 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 32 3 1 1 0 0 0 33 4 1 1 0 0 0 34 35 1 1 0 0 0 35 6 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:	3.696
LogD:	3.543
LogS:	-3.768
# 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:	5.383
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:	-5.847
MDCK Permeability:	1.1561749488464557e-05
Pgp-inhibitor:	0.505
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.821
20% Bioavailability (F20%):	0.31
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	93.07792663574219%
Volume Distribution (VD):	0.428
Pgp-substrate:	3.857912063598633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.726
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	1.049
Half-life (T1/2):	0.598

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.174
Skin Sensitization:	0.049
Carcinogencity:	0.059
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC57362

Natural Product ID:	NPC57362
*Common Name:**	3-O-(Beta-D-Glucopyranosyl)-23-Hydroxyursolic Acid
IUPAC Name:	(1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	SHSTYRBKXWDVCB-CWVWMCCNSA-N
Standard InCHI:	InChI=1S/C36H58O9/c1-19-9-14-36(31(42)43)16-15-34(5)21(26(36)20(19)2)7-8-24-32(3)12-11-25(33(4,18-38)23(32)10-13-35(24,34)6)45-30-29(41)28(40)27(39)22(17-37)44-30/h7,19-20,22-30,37-41H,8-18H2,1-6H3,(H,42,43)/t19-,20+,22-,23-,24-,25+,26+,27-,28+,29-,30+,32+,33+,34-,35-,36+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3[C@@H](C)[C@H](C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461104
PubChem CID:	21589723
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
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510614]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24490	Cussonia bancoensis	Species	Araliaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	22100.0	nM	PMID[549157]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	126000.0	nM	PMID[549157]

☑ 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 NPC57362 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	257
0.1-0.2	1714
0.2-0.3	5022
0.3-0.4	11700
0.4-0.5	10437
0.5-0.6	6116
0.6-0.7	4148
0.7-0.8	1952
0.8-0.85	672
0.85-0.9	298
0.9-0.95	142
0.95-1	239

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167383
1.0	High Similarity	NPC237503
1.0	High Similarity	NPC204407
1.0	High Similarity	NPC306746
0.9901	High Similarity	NPC474589
0.9901	High Similarity	NPC476881
0.9901	High Similarity	NPC29069
0.9901	High Similarity	NPC56713
0.9901	High Similarity	NPC476885
0.9901	High Similarity	NPC476883
0.9901	High Similarity	NPC475296
0.9901	High Similarity	NPC102914
0.9901	High Similarity	NPC199457
0.9901	High Similarity	NPC108709
0.9901	High Similarity	NPC476887
0.9901	High Similarity	NPC476880
0.9901	High Similarity	NPC90856
0.9901	High Similarity	NPC127056
0.9901	High Similarity	NPC476882
0.9901	High Similarity	NPC476886
0.9901	High Similarity	NPC59804
0.9901	High Similarity	NPC270667
0.9901	High Similarity	NPC68419
0.9901	High Similarity	NPC476884
0.9901	High Similarity	NPC110139
0.9901	High Similarity	NPC164194
0.9901	High Similarity	NPC174679
0.9901	High Similarity	NPC136877
0.9901	High Similarity	NPC274507
0.9901	High Similarity	NPC7870
0.9901	High Similarity	NPC279554
0.9901	High Similarity	NPC75747
0.99	High Similarity	NPC177246
0.99	High Similarity	NPC476123
0.99	High Similarity	NPC28198
0.99	High Similarity	NPC284807
0.9804	High Similarity	NPC235841
0.9804	High Similarity	NPC164419
0.9804	High Similarity	NPC211798
0.9804	High Similarity	NPC179434
0.9804	High Similarity	NPC30397
0.9804	High Similarity	NPC191763
0.9804	High Similarity	NPC108748
0.9804	High Similarity	NPC473481
0.9804	High Similarity	NPC31839
0.9804	High Similarity	NPC297208
0.9802	High Similarity	NPC137917
0.9802	High Similarity	NPC127853
0.98	High Similarity	NPC473538
0.98	High Similarity	NPC283849
0.9709	High Similarity	NPC475504
0.9709	High Similarity	NPC128925
0.9709	High Similarity	NPC257468
0.9709	High Similarity	NPC469946
0.9709	High Similarity	NPC139894
0.9709	High Similarity	NPC475516
0.9709	High Similarity	NPC101744
0.9709	High Similarity	NPC471383
0.9709	High Similarity	NPC473373
0.9709	High Similarity	NPC109079
0.9709	High Similarity	NPC80843
0.9709	High Similarity	NPC79718
0.9709	High Similarity	NPC471967
0.9709	High Similarity	NPC473383
0.9709	High Similarity	NPC139044
0.9709	High Similarity	NPC46388
0.9709	High Similarity	NPC102439
0.9709	High Similarity	NPC48249
0.9709	High Similarity	NPC1046
0.9709	High Similarity	NPC256798
0.9709	High Similarity	NPC116794
0.9709	High Similarity	NPC37739
0.9709	High Similarity	NPC104071
0.9709	High Similarity	NPC324875
0.9709	High Similarity	NPC10320
0.9709	High Similarity	NPC276093
0.9709	High Similarity	NPC292677
0.9709	High Similarity	NPC104400
0.9706	High Similarity	NPC269095
0.9706	High Similarity	NPC242611
0.9706	High Similarity	NPC78046
0.9706	High Similarity	NPC220984
0.97	High Similarity	NPC475611
0.9615	High Similarity	NPC219180
0.9615	High Similarity	NPC163183
0.9615	High Similarity	NPC251263
0.9615	High Similarity	NPC114287
0.9615	High Similarity	NPC473343
0.9615	High Similarity	NPC238935
0.9615	High Similarity	NPC204458
0.9615	High Similarity	NPC96641
0.9615	High Similarity	NPC309714
0.9615	High Similarity	NPC241909
0.9615	High Similarity	NPC258885
0.9615	High Similarity	NPC295823
0.9615	High Similarity	NPC189884
0.9615	High Similarity	NPC475467
0.9615	High Similarity	NPC138334
0.9615	High Similarity	NPC192600
0.9615	High Similarity	NPC166422
0.9615	High Similarity	NPC155410
0.9615	High Similarity	NPC133818
0.9615	High Similarity	NPC473826
0.9615	High Similarity	NPC475287
0.9615	High Similarity	NPC47063
0.9615	High Similarity	NPC174720
0.9615	High Similarity	NPC151543
0.9615	High Similarity	NPC73318
0.9615	High Similarity	NPC271138
0.9615	High Similarity	NPC269315
0.9615	High Similarity	NPC475208
0.9615	High Similarity	NPC114304
0.9615	High Similarity	NPC323341
0.9615	High Similarity	NPC150400
0.9615	High Similarity	NPC124296
0.9615	High Similarity	NPC46665
0.9615	High Similarity	NPC134835
0.9524	High Similarity	NPC475633
0.9524	High Similarity	NPC293330
0.9524	High Similarity	NPC475140
0.9524	High Similarity	NPC227551
0.9524	High Similarity	NPC473714
0.9524	High Similarity	NPC475486
0.9524	High Similarity	NPC65105
0.9524	High Similarity	NPC76972
0.9524	High Similarity	NPC204414
0.9524	High Similarity	NPC123199
0.9524	High Similarity	NPC100639
0.9524	High Similarity	NPC41061
0.9524	High Similarity	NPC469782
0.9524	High Similarity	NPC54636
0.9524	High Similarity	NPC164389
0.9524	High Similarity	NPC67857
0.9524	High Similarity	NPC119592
0.9524	High Similarity	NPC57484
0.9524	High Similarity	NPC4328
0.9524	High Similarity	NPC70809
0.9524	High Similarity	NPC471385
0.9524	High Similarity	NPC161717
0.9524	High Similarity	NPC476068
0.9524	High Similarity	NPC60557
0.9524	High Similarity	NPC298034
0.9524	High Similarity	NPC202828
0.9524	High Similarity	NPC224381
0.9524	High Similarity	NPC305981
0.9524	High Similarity	NPC261506
0.9524	High Similarity	NPC43550
0.9524	High Similarity	NPC236638
0.9524	High Similarity	NPC71065
0.9524	High Similarity	NPC79643
0.9524	High Similarity	NPC250247
0.9524	High Similarity	NPC471550
0.9524	High Similarity	NPC309907
0.9524	High Similarity	NPC475160
0.9524	High Similarity	NPC294453
0.9519	High Similarity	NPC100383
0.951	High Similarity	NPC285576
0.9434	High Similarity	NPC476992
0.9434	High Similarity	NPC471384
0.9434	High Similarity	NPC160415
0.9434	High Similarity	NPC288205
0.9434	High Similarity	NPC26626
0.9434	High Similarity	NPC291903
0.9434	High Similarity	NPC37134
0.9434	High Similarity	NPC75287
0.9434	High Similarity	NPC161674
0.9434	High Similarity	NPC305267
0.9434	High Similarity	NPC51465
0.9434	High Similarity	NPC58448
0.9423	High Similarity	NPC190837
0.9406	High Similarity	NPC173583
0.9346	High Similarity	NPC148417
0.9346	High Similarity	NPC300419
0.9346	High Similarity	NPC136768
0.9346	High Similarity	NPC102505
0.9346	High Similarity	NPC471547
0.9346	High Similarity	NPC220160
0.9346	High Similarity	NPC191827
0.9346	High Similarity	NPC323359
0.9346	High Similarity	NPC33012
0.9346	High Similarity	NPC123522
0.9346	High Similarity	NPC473405
0.9346	High Similarity	NPC104137
0.9346	High Similarity	NPC473824
0.9346	High Similarity	NPC85154
0.9346	High Similarity	NPC309223
0.9346	High Similarity	NPC68175
0.9346	High Similarity	NPC185466
0.9346	High Similarity	NPC69811
0.9346	High Similarity	NPC470876
0.9346	High Similarity	NPC110633
0.9346	High Similarity	NPC475119
0.9346	High Similarity	NPC475209
0.9346	High Similarity	NPC473452
0.9346	High Similarity	NPC8524
0.9346	High Similarity	NPC286457
0.9346	High Similarity	NPC475514
0.9333	High Similarity	NPC125923
0.9333	High Similarity	NPC64106
0.9333	High Similarity	NPC65590

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 NPC57362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	2008
0.2-0.3	3871
0.3-0.4	1977
0.4-0.5	605
0.5-0.6	273
0.6-0.7	147
0.7-0.8	20
0.8-0.85	11
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD8132	Clinical (unspecified phase)
0.885	High Similarity	NPD8328	Phase 3
0.8818	High Similarity	NPD8295	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD8133	Approved
0.8333	Intermediate Similarity	NPD6412	Phase 2
0.8257	Intermediate Similarity	NPD6686	Approved
0.8155	Intermediate Similarity	NPD7748	Approved
0.8095	Intermediate Similarity	NPD7902	Approved
0.8067	Intermediate Similarity	NPD7507	Approved
0.7961	Intermediate Similarity	NPD7515	Phase 2
0.7949	Intermediate Similarity	NPD8377	Approved
0.7949	Intermediate Similarity	NPD8294	Approved
0.7881	Intermediate Similarity	NPD8378	Approved
0.7881	Intermediate Similarity	NPD8296	Approved
0.7881	Intermediate Similarity	NPD8380	Approved
0.7881	Intermediate Similarity	NPD8379	Approved
0.7881	Intermediate Similarity	NPD8033	Approved
0.7881	Intermediate Similarity	NPD8335	Approved
0.7869	Intermediate Similarity	NPD7319	Approved
0.781	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD7900	Approved
0.7787	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD7327	Approved
0.7712	Intermediate Similarity	NPD7516	Approved
0.7583	Intermediate Similarity	NPD7503	Approved
0.7583	Intermediate Similarity	NPD8516	Approved
0.7583	Intermediate Similarity	NPD8515	Approved
0.7583	Intermediate Similarity	NPD8513	Phase 3
0.7583	Intermediate Similarity	NPD8517	Approved
0.7561	Intermediate Similarity	NPD8293	Discontinued
0.7453	Intermediate Similarity	NPD8035	Phase 2
0.7453	Intermediate Similarity	NPD8034	Phase 2
0.7377	Intermediate Similarity	NPD6370	Approved
0.7364	Intermediate Similarity	NPD7638	Approved
0.735	Intermediate Similarity	NPD8297	Approved
0.735	Intermediate Similarity	NPD6882	Approved
0.7345	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7645	Phase 2
0.7297	Intermediate Similarity	NPD7640	Approved
0.7297	Intermediate Similarity	NPD7639	Approved
0.7258	Intermediate Similarity	NPD7492	Approved
0.725	Intermediate Similarity	NPD6009	Approved
0.7241	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7213	Intermediate Similarity	NPD6054	Approved
0.7213	Intermediate Similarity	NPD6059	Approved
0.7213	Intermediate Similarity	NPD6319	Approved
0.7212	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6616	Approved
0.7177	Intermediate Similarity	NPD6067	Discontinued
0.7155	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD4632	Approved
0.713	Intermediate Similarity	NPD7128	Approved
0.713	Intermediate Similarity	NPD6402	Approved
0.713	Intermediate Similarity	NPD6675	Approved
0.713	Intermediate Similarity	NPD5739	Approved
0.7119	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6373	Approved
0.7094	Intermediate Similarity	NPD6372	Approved
0.7034	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6016	Approved
0.7016	Intermediate Similarity	NPD6015	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD6899	Approved
0.6975	Remote Similarity	NPD8130	Phase 1
0.6975	Remote Similarity	NPD6649	Approved
0.6975	Remote Similarity	NPD6650	Approved
0.6972	Remote Similarity	NPD6411	Approved
0.6967	Remote Similarity	NPD7115	Discovery
0.696	Remote Similarity	NPD5988	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD5697	Approved
0.6909	Remote Similarity	NPD8171	Discontinued
0.6891	Remote Similarity	NPD6883	Approved
0.6891	Remote Similarity	NPD7102	Approved
0.6891	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD6698	Approved
0.6881	Remote Similarity	NPD46	Approved
0.6852	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6869	Approved
0.6833	Remote Similarity	NPD6847	Approved
0.6833	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD3618	Phase 1
0.6814	Remote Similarity	NPD6084	Phase 2
0.6814	Remote Similarity	NPD6083	Phase 2
0.6807	Remote Similarity	NPD6014	Approved
0.6807	Remote Similarity	NPD6012	Approved
0.6807	Remote Similarity	NPD6013	Approved
0.6792	Remote Similarity	NPD4786	Approved
0.6789	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6101	Approved
0.6789	Remote Similarity	NPD5328	Approved
0.678	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7604	Phase 2
0.6762	Remote Similarity	NPD3667	Approved
0.6759	Remote Similarity	NPD3573	Approved
0.6754	Remote Similarity	NPD4225	Approved
0.6746	Remote Similarity	NPD5983	Phase 2
0.6744	Remote Similarity	NPD8074	Phase 3
0.6724	Remote Similarity	NPD7632	Discontinued
0.6723	Remote Similarity	NPD6011	Approved
0.6695	Remote Similarity	NPD6008	Approved
0.6694	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6921	Approved
0.6613	Remote Similarity	NPD6940	Discontinued
0.6612	Remote Similarity	NPD4634	Approved
0.6607	Remote Similarity	NPD5778	Approved
0.6607	Remote Similarity	NPD5779	Approved
0.6607	Remote Similarity	NPD4202	Approved
0.6571	Remote Similarity	NPD7525	Registered
0.6552	Remote Similarity	NPD5286	Approved
0.6552	Remote Similarity	NPD4700	Approved
0.6552	Remote Similarity	NPD4696	Approved
0.6552	Remote Similarity	NPD5285	Approved
0.6545	Remote Similarity	NPD5737	Approved
0.6545	Remote Similarity	NPD6903	Approved
0.6545	Remote Similarity	NPD6672	Approved
0.6542	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3669	Approved
0.6538	Remote Similarity	NPD6697	Approved
0.6538	Remote Similarity	NPD6118	Approved
0.6538	Remote Similarity	NPD6115	Approved
0.6538	Remote Similarity	NPD6114	Approved
0.6493	Remote Similarity	NPD8449	Approved
0.6491	Remote Similarity	NPD5695	Phase 3
0.6481	Remote Similarity	NPD3133	Approved
0.6481	Remote Similarity	NPD3666	Approved
0.6481	Remote Similarity	NPD3665	Phase 1
0.648	Remote Similarity	NPD6274	Approved
0.6466	Remote Similarity	NPD5696	Approved
0.6466	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7101	Approved
0.6457	Remote Similarity	NPD7100	Approved
0.6444	Remote Similarity	NPD8450	Suspended
0.6442	Remote Similarity	NPD6116	Phase 1
0.6441	Remote Similarity	NPD5225	Approved
0.6441	Remote Similarity	NPD5224	Approved
0.6441	Remote Similarity	NPD5226	Approved
0.6441	Remote Similarity	NPD4633	Approved
0.6441	Remote Similarity	NPD5211	Phase 2
0.6435	Remote Similarity	NPD5222	Approved
0.6435	Remote Similarity	NPD5221	Approved
0.6435	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4697	Phase 3
0.6417	Remote Similarity	NPD4768	Approved
0.6417	Remote Similarity	NPD4767	Approved
0.6387	Remote Similarity	NPD5174	Approved
0.6387	Remote Similarity	NPD5175	Approved
0.6379	Remote Similarity	NPD5173	Approved
0.6378	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD7625	Phase 1
0.6357	Remote Similarity	NPD6908	Approved
0.6357	Remote Similarity	NPD6909	Approved
0.6356	Remote Similarity	NPD5344	Discontinued
0.6356	Remote Similarity	NPD5223	Approved
0.6355	Remote Similarity	NPD1780	Approved
0.6355	Remote Similarity	NPD1779	Approved
0.6349	Remote Similarity	NPD6868	Approved
0.6348	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6117	Approved
0.6339	Remote Similarity	NPD4753	Phase 2
0.6333	Remote Similarity	NPD5141	Approved
0.633	Remote Similarity	NPD3668	Phase 3
0.6316	Remote Similarity	NPD8336	Approved
0.6316	Remote Similarity	NPD8337	Approved
0.6311	Remote Similarity	NPD4729	Approved
0.6311	Remote Similarity	NPD4730	Approved
0.6299	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6317	Approved
0.6293	Remote Similarity	NPD7839	Suspended
0.6293	Remote Similarity	NPD7614	Phase 1
0.6293	Remote Similarity	NPD7732	Phase 3
0.6283	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD8338	Approved
0.625	Remote Similarity	NPD7641	Discontinued
0.625	Remote Similarity	NPD4754	Approved
0.625	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD6314	Approved
0.624	Remote Similarity	NPD6053	Discontinued
0.6228	Remote Similarity	NPD7637	Suspended
0.6222	Remote Similarity	NPD5956	Approved
0.6216	Remote Similarity	NPD6098	Approved
0.6212	Remote Similarity	NPD8342	Approved
0.6212	Remote Similarity	NPD8340	Approved
0.6212	Remote Similarity	NPD8341	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