NPASS Compound

Structure

NPC64106 OpenBabel07101718232D 47 52 0 0 1 0 0 0 0 0999 V2000 2.5491 4.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 3.4340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 -2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 2.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6472 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0585 -2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 3.4340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6994 2.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3987 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7975 0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8497 0.4906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6994 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7975 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9478 -0.4906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0981 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6994 -0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3987 -0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0981 0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3987 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5491 -1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8497 0.4906 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 2.5491 1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4969 0.9811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 -3.1711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -2.4528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6472 -0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9478 -1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 -0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 -1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9478 1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 1.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 5 34 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 36 1 0 0 0 0 11 12 1 0 0 0 0 11 34 1 0 0 0 0 12 36 1 0 0 0 0 13 21 1 0 0 0 0 13 32 1 0 0 0 0 14 20 1 0 0 0 0 14 35 1 0 0 0 0 15 37 1 0 0 0 0 16 33 1 0 0 0 0 16 38 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 24 2 0 0 0 0 19 24 1 0 0 0 0 19 34 1 0 0 0 0 20 28 1 0 0 0 0 20 39 1 1 0 0 0 21 29 1 0 0 0 0 21 40 1 6 0 0 0 22 15 1 6 0 0 0 22 25 1 0 0 0 0 22 46 1 0 0 0 0 23 32 1 1 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 26 1 0 0 0 0 25 41 1 1 0 0 0 26 27 1 0 0 0 0 26 42 1 6 0 0 0 27 30 1 0 0 0 0 27 43 1 1 0 0 0 28 32 1 1 0 0 0 28 33 1 0 0 0 0 29 33 1 1 0 0 0 29 44 1 0 0 0 0 30 46 1 0 0 0 0 30 47 1 6 0 0 0 31 45 2 0 0 0 0 31 47 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:	664.38
Volume:	668.656
LogP:	2.007
LogD:	1.228
LogS:	-3.202
# Rotatable Bonds:	5
TPSA:	197.37
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	5.825
Fsp3:	0.861
Lipinski Rule-of-5:	Rejected
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:	-5.542
MDCK Permeability:	1.1897237527591642e-05
Pgp-inhibitor:	0.838
Pgp-substrate:	0.738
Human Intestinal Absorption (HIA):	0.828
20% Bioavailability (F20%):	0.302
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	84.07721710205078%
Volume Distribution (VD):	0.443
Pgp-substrate:	6.439037799835205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.596
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.448
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	1.174
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.257
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.263
Rat Oral Acute Toxicity:	0.52
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.123
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.746

Download Data

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

Natural Product: NPC64106

Natural Product ID:	NPC64106
*Common Name:**	Quadranoside V
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,13-dodecahydro-2H-picene-4a-carboxylate
Synonyms:	Quadranoside V
Standard InCHIKey:	XNXMFRGRMHPZKN-JJPABSQASA-N
Standard InCHI:	InChI=1S/C36H56O11/c1-17-9-10-36(31(45)47-30-27(43)26(42)25(41)22(15-37)46-30)12-11-34(5)19(24(36)18(17)2)7-8-23-32(3)13-21(40)29(44)33(4,16-38)28(32)20(39)14-35(23,34)6/h7,17,20-23,25-30,37-44H,8-16H2,1-6H3/t17-,20-,21-,22-,23-,25-,26+,27-,28-,29+,30+,32-,33+,34-,35-,36+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H](C(=C3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)C[C@@H](O)[C@@H]2[C@]4(C)C[C@H]([C@@H]([C@@]2(C)CO)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500700
PubChem CID:	10327071
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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	80.1	%	PMID[566127]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	77.7	%	PMID[566127]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	67.5	%	PMID[566127]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	59.3	%	PMID[566127]

☑ 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 NPC64106 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	262
0.1-0.2	1567
0.2-0.3	4647
0.3-0.4	9795
0.4-0.5	12217
0.5-0.6	6711
0.6-0.7	4554
0.7-0.8	2050
0.8-0.85	491
0.85-0.9	199
0.9-0.95	195
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65590
1.0	High Similarity	NPC125923
1.0	High Similarity	NPC212968
0.9903	High Similarity	NPC190837
0.9808	High Similarity	NPC195132
0.9808	High Similarity	NPC161434
0.9615	High Similarity	NPC220984
0.9519	High Similarity	NPC137917
0.9434	High Similarity	NPC116794
0.9429	High Similarity	NPC199457
0.9429	High Similarity	NPC102914
0.9429	High Similarity	NPC75747
0.9429	High Similarity	NPC110139
0.9429	High Similarity	NPC269095
0.9429	High Similarity	NPC274507
0.9429	High Similarity	NPC68419
0.9429	High Similarity	NPC78046
0.9429	High Similarity	NPC7870
0.9429	High Similarity	NPC108709
0.9423	High Similarity	NPC285576
0.9346	High Similarity	NPC271138
0.9346	High Similarity	NPC269315
0.934	High Similarity	NPC179434
0.934	High Similarity	NPC473481
0.934	High Similarity	NPC30397
0.934	High Similarity	NPC211798
0.934	High Similarity	NPC191763
0.934	High Similarity	NPC108748
0.934	High Similarity	NPC235841
0.934	High Similarity	NPC297208
0.9333	High Similarity	NPC306746
0.9333	High Similarity	NPC127853
0.9333	High Similarity	NPC237503
0.9333	High Similarity	NPC204407
0.9333	High Similarity	NPC167383
0.9333	High Similarity	NPC57362
0.9259	High Similarity	NPC475633
0.9252	High Similarity	NPC473383
0.9252	High Similarity	NPC256798
0.9252	High Similarity	NPC46388
0.9252	High Similarity	NPC128925
0.9252	High Similarity	NPC48249
0.9252	High Similarity	NPC139894
0.9252	High Similarity	NPC37739
0.9245	High Similarity	NPC476881
0.9245	High Similarity	NPC475296
0.9245	High Similarity	NPC279554
0.9245	High Similarity	NPC127056
0.9245	High Similarity	NPC270667
0.9245	High Similarity	NPC29069
0.9245	High Similarity	NPC90856
0.9245	High Similarity	NPC474589
0.9245	High Similarity	NPC59804
0.9245	High Similarity	NPC174679
0.9245	High Similarity	NPC476887
0.9245	High Similarity	NPC476882
0.9245	High Similarity	NPC164194
0.9245	High Similarity	NPC476883
0.9245	High Similarity	NPC136877
0.9245	High Similarity	NPC56713
0.9245	High Similarity	NPC476884
0.9245	High Similarity	NPC476885
0.9245	High Similarity	NPC476886
0.9245	High Similarity	NPC476880
0.9238	High Similarity	NPC28198
0.9238	High Similarity	NPC476123
0.9238	High Similarity	NPC177246
0.9238	High Similarity	NPC284807
0.9174	High Similarity	NPC473126
0.9167	High Similarity	NPC258885
0.9167	High Similarity	NPC47063
0.9167	High Similarity	NPC138334
0.9167	High Similarity	NPC150400
0.9167	High Similarity	NPC124296
0.9167	High Similarity	NPC134835
0.9167	High Similarity	NPC96641
0.9167	High Similarity	NPC73318
0.9167	High Similarity	NPC475208
0.9167	High Similarity	NPC163183
0.9167	High Similarity	NPC189884
0.9167	High Similarity	NPC204458
0.9167	High Similarity	NPC473343
0.9167	High Similarity	NPC238935
0.9159	High Similarity	NPC31839
0.9159	High Similarity	NPC164419
0.9143	High Similarity	NPC283849
0.9143	High Similarity	NPC473538
0.9074	High Similarity	NPC475504
0.9074	High Similarity	NPC104400
0.9074	High Similarity	NPC471383
0.9074	High Similarity	NPC475516
0.9074	High Similarity	NPC276093
0.9074	High Similarity	NPC257468
0.9074	High Similarity	NPC104071
0.9074	High Similarity	NPC1046
0.9074	High Similarity	NPC102439
0.9074	High Similarity	NPC79718
0.9074	High Similarity	NPC473373
0.9074	High Similarity	NPC471967
0.9074	High Similarity	NPC109079
0.9074	High Similarity	NPC10320
0.9074	High Similarity	NPC469946
0.9074	High Similarity	NPC324875
0.9074	High Similarity	NPC80843
0.9074	High Similarity	NPC292677
0.9074	High Similarity	NPC139044
0.9074	High Similarity	NPC101744
0.9065	High Similarity	NPC242611
0.9048	High Similarity	NPC475611
0.9	High Similarity	NPC471384
0.9	High Similarity	NPC160415
0.9	High Similarity	NPC58448
0.9	High Similarity	NPC161674
0.8991	High Similarity	NPC166422
0.8991	High Similarity	NPC251309
0.8991	High Similarity	NPC475287
0.8991	High Similarity	NPC133818
0.8991	High Similarity	NPC46665
0.8991	High Similarity	NPC192600
0.8991	High Similarity	NPC114304
0.8991	High Similarity	NPC475467
0.8991	High Similarity	NPC323341
0.8991	High Similarity	NPC219180
0.8991	High Similarity	NPC151543
0.8991	High Similarity	NPC155410
0.8991	High Similarity	NPC309714
0.8991	High Similarity	NPC174720
0.8991	High Similarity	NPC241909
0.8991	High Similarity	NPC295823
0.8991	High Similarity	NPC473826
0.8991	High Similarity	NPC251263
0.8991	High Similarity	NPC114287
0.8981	High Similarity	NPC292196
0.8981	High Similarity	NPC285410
0.8981	High Similarity	NPC250481
0.8981	High Similarity	NPC263827
0.8919	High Similarity	NPC110633
0.8919	High Similarity	NPC471547
0.8919	High Similarity	NPC148417
0.8919	High Similarity	NPC68175
0.8919	High Similarity	NPC136768
0.8919	High Similarity	NPC300419
0.8919	High Similarity	NPC473405
0.8909	High Similarity	NPC293330
0.8909	High Similarity	NPC79643
0.8909	High Similarity	NPC476068
0.8909	High Similarity	NPC102088
0.8909	High Similarity	NPC204414
0.8909	High Similarity	NPC71065
0.8909	High Similarity	NPC57484
0.8909	High Similarity	NPC67857
0.8909	High Similarity	NPC119592
0.8909	High Similarity	NPC471550
0.8909	High Similarity	NPC250247
0.8909	High Similarity	NPC76972
0.8909	High Similarity	NPC123199
0.8909	High Similarity	NPC475160
0.8909	High Similarity	NPC471385
0.8909	High Similarity	NPC54636
0.8909	High Similarity	NPC41061
0.8909	High Similarity	NPC469782
0.8909	High Similarity	NPC261506
0.8909	High Similarity	NPC305981
0.8909	High Similarity	NPC202828
0.8909	High Similarity	NPC70809
0.8909	High Similarity	NPC100639
0.8909	High Similarity	NPC309907
0.8909	High Similarity	NPC298034
0.8909	High Similarity	NPC164389
0.8909	High Similarity	NPC4328
0.8909	High Similarity	NPC294453
0.8909	High Similarity	NPC236638
0.8909	High Similarity	NPC65105
0.8909	High Similarity	NPC43550
0.8909	High Similarity	NPC161717
0.8909	High Similarity	NPC473714
0.8909	High Similarity	NPC475486
0.8909	High Similarity	NPC60557
0.8909	High Similarity	NPC224381
0.8909	High Similarity	NPC227551
0.8909	High Similarity	NPC475140
0.8899	High Similarity	NPC100383
0.8899	High Similarity	NPC477253
0.8899	High Similarity	NPC233003
0.8889	High Similarity	NPC129340
0.886	High Similarity	NPC275343
0.8857	High Similarity	NPC99627
0.8857	High Similarity	NPC473129
0.8839	High Similarity	NPC471548
0.8839	High Similarity	NPC36831
0.8839	High Similarity	NPC237191
0.8839	High Similarity	NPC475899
0.8829	High Similarity	NPC26626
0.8829	High Similarity	NPC476992
0.8829	High Similarity	NPC75287
0.8829	High Similarity	NPC37134
0.8829	High Similarity	NPC288205
0.8829	High Similarity	NPC305267
0.8829	High Similarity	NPC51465
0.8829	High Similarity	NPC291903

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 NPC64106 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	1801
0.2-0.3	3770
0.3-0.4	2162
0.4-0.5	719
0.5-0.6	299
0.6-0.7	131
0.7-0.8	30
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9151	High Similarity	NPD8132	Clinical (unspecified phase)
0.8584	High Similarity	NPD8295	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD8328	Phase 3
0.8	Intermediate Similarity	NPD8133	Approved
0.7946	Intermediate Similarity	NPD6412	Phase 2
0.7876	Intermediate Similarity	NPD6686	Approved
0.7724	Intermediate Similarity	NPD7507	Approved
0.7686	Intermediate Similarity	NPD8516	Approved
0.7686	Intermediate Similarity	NPD8515	Approved
0.7686	Intermediate Similarity	NPD8033	Approved
0.7686	Intermediate Similarity	NPD8513	Phase 3
0.7686	Intermediate Similarity	NPD8517	Approved
0.7603	Intermediate Similarity	NPD8294	Approved
0.7603	Intermediate Similarity	NPD8377	Approved
0.7593	Intermediate Similarity	NPD7748	Approved
0.7545	Intermediate Similarity	NPD7902	Approved
0.7541	Intermediate Similarity	NPD8380	Approved
0.7541	Intermediate Similarity	NPD8335	Approved
0.7541	Intermediate Similarity	NPD8379	Approved
0.7541	Intermediate Similarity	NPD8296	Approved
0.7541	Intermediate Similarity	NPD7503	Approved
0.7541	Intermediate Similarity	NPD8378	Approved
0.754	Intermediate Similarity	NPD7319	Approved
0.7521	Intermediate Similarity	NPD7516	Approved
0.746	Intermediate Similarity	NPD7736	Approved
0.7438	Intermediate Similarity	NPD7327	Approved
0.7438	Intermediate Similarity	NPD7328	Approved
0.7407	Intermediate Similarity	NPD7515	Phase 2
0.7273	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7900	Approved
0.7248	Intermediate Similarity	NPD6411	Approved
0.7244	Intermediate Similarity	NPD8293	Discontinued
0.7203	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6101	Approved
0.7064	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6370	Approved
0.7027	Intermediate Similarity	NPD6399	Phase 3
0.7025	Intermediate Similarity	NPD6882	Approved
0.7025	Intermediate Similarity	NPD8297	Approved
0.7018	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7639	Approved
0.6957	Remote Similarity	NPD7640	Approved
0.6953	Remote Similarity	NPD7492	Approved
0.6942	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8035	Phase 2
0.6937	Remote Similarity	NPD8034	Phase 2
0.6935	Remote Similarity	NPD6009	Approved
0.6905	Remote Similarity	NPD6054	Approved
0.6905	Remote Similarity	NPD6059	Approved
0.6905	Remote Similarity	NPD6319	Approved
0.6899	Remote Similarity	NPD6616	Approved
0.6875	Remote Similarity	NPD5778	Approved
0.6875	Remote Similarity	NPD5779	Approved
0.6875	Remote Similarity	NPD6067	Discontinued
0.6846	Remote Similarity	NPD7078	Approved
0.6846	Remote Similarity	NPD8074	Phase 3
0.6829	Remote Similarity	NPD4632	Approved
0.6807	Remote Similarity	NPD5739	Approved
0.6807	Remote Similarity	NPD6402	Approved
0.6807	Remote Similarity	NPD6675	Approved
0.6807	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD7115	Discovery
0.6786	Remote Similarity	NPD7983	Approved
0.6777	Remote Similarity	NPD6372	Approved
0.6777	Remote Similarity	NPD6373	Approved
0.6762	Remote Similarity	NPD7645	Phase 2
0.675	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8171	Discontinued
0.6719	Remote Similarity	NPD6016	Approved
0.6719	Remote Similarity	NPD6015	Approved
0.6697	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD46	Approved
0.6696	Remote Similarity	NPD6698	Approved
0.6694	Remote Similarity	NPD7320	Approved
0.6694	Remote Similarity	NPD6881	Approved
0.6694	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6612	Remote Similarity	NPD5697	Approved
0.6612	Remote Similarity	NPD5701	Approved
0.6606	Remote Similarity	NPD4786	Approved
0.6589	Remote Similarity	NPD6921	Approved
0.6585	Remote Similarity	NPD6883	Approved
0.6585	Remote Similarity	NPD7102	Approved
0.6585	Remote Similarity	NPD7290	Approved
0.6581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4225	Approved
0.6574	Remote Similarity	NPD3667	Approved
0.6555	Remote Similarity	NPD7632	Discontinued
0.6532	Remote Similarity	NPD6617	Approved
0.6532	Remote Similarity	NPD6847	Approved
0.6532	Remote Similarity	NPD6869	Approved
0.6529	Remote Similarity	NPD6008	Approved
0.6518	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6013	Approved
0.6504	Remote Similarity	NPD6014	Approved
0.6504	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD6084	Phase 2
0.6496	Remote Similarity	NPD6083	Phase 2
0.6489	Remote Similarity	NPD7604	Phase 2
0.6486	Remote Similarity	NPD3618	Phase 1
0.6462	Remote Similarity	NPD5983	Phase 2
0.646	Remote Similarity	NPD5328	Approved
0.6457	Remote Similarity	NPD6940	Discontinued
0.6429	Remote Similarity	NPD3573	Approved
0.6429	Remote Similarity	NPD7524	Approved
0.6423	Remote Similarity	NPD6011	Approved
0.6418	Remote Similarity	NPD6033	Approved
0.641	Remote Similarity	NPD7839	Suspended
0.6404	Remote Similarity	NPD7838	Discovery
0.64	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6336	Discontinued
0.6364	Remote Similarity	NPD3669	Approved
0.6364	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD7641	Discontinued
0.6356	Remote Similarity	NPD4755	Approved
0.6355	Remote Similarity	NPD6114	Approved
0.6355	Remote Similarity	NPD6115	Approved
0.6355	Remote Similarity	NPD6697	Approved
0.6355	Remote Similarity	NPD6118	Approved
0.635	Remote Similarity	NPD8449	Approved
0.6348	Remote Similarity	NPD6079	Approved
0.6348	Remote Similarity	NPD7637	Suspended
0.6339	Remote Similarity	NPD7146	Approved
0.6339	Remote Similarity	NPD6684	Approved
0.6339	Remote Similarity	NPD5330	Approved
0.6339	Remote Similarity	NPD7334	Approved
0.6339	Remote Similarity	NPD7521	Approved
0.6339	Remote Similarity	NPD6409	Approved
0.6333	Remote Similarity	NPD5344	Discontinued
0.6325	Remote Similarity	NPD5695	Phase 3
0.632	Remote Similarity	NPD4634	Approved
0.6316	Remote Similarity	NPD8340	Approved
0.6316	Remote Similarity	NPD8341	Approved
0.6316	Remote Similarity	NPD8342	Approved
0.6316	Remote Similarity	NPD8299	Approved
0.6304	Remote Similarity	NPD8450	Suspended
0.6293	Remote Similarity	NPD4202	Approved
0.6279	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7260	Phase 2
0.6271	Remote Similarity	NPD7732	Phase 3
0.6271	Remote Similarity	NPD7614	Phase 1
0.6269	Remote Similarity	NPD8451	Approved
0.6262	Remote Similarity	NPD6116	Phase 1
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD4700	Approved
0.6241	Remote Similarity	NPD7829	Approved
0.6241	Remote Similarity	NPD7830	Approved
0.6239	Remote Similarity	NPD7525	Registered
0.6233	Remote Similarity	NPD7625	Phase 1
0.6228	Remote Similarity	NPD5737	Approved
0.6228	Remote Similarity	NPD6903	Approved
0.6228	Remote Similarity	NPD6672	Approved
0.6222	Remote Similarity	NPD8448	Approved
0.6212	Remote Similarity	NPD8444	Approved
0.6211	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5281	Approved
0.6207	Remote Similarity	NPD5284	Approved
0.6204	Remote Similarity	NPD8391	Approved
0.6204	Remote Similarity	NPD8392	Approved
0.6204	Remote Similarity	NPD8390	Approved
0.6202	Remote Similarity	NPD6274	Approved
0.6195	Remote Similarity	NPD5279	Phase 3
0.6183	Remote Similarity	NPD7100	Approved
0.6183	Remote Similarity	NPD7101	Approved
0.6182	Remote Similarity	NPD1779	Approved
0.6182	Remote Similarity	NPD1780	Approved
0.6168	Remote Similarity	NPD6117	Approved
0.6167	Remote Similarity	NPD5696	Approved
0.6161	Remote Similarity	NPD3133	Approved
0.6161	Remote Similarity	NPD3665	Phase 1
0.6161	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3666	Approved
0.6161	Remote Similarity	NPD3668	Phase 3
0.6148	Remote Similarity	NPD5225	Approved
0.6148	Remote Similarity	NPD4633	Approved
0.6148	Remote Similarity	NPD5226	Approved
0.6148	Remote Similarity	NPD5224	Approved
0.6148	Remote Similarity	NPD5211	Phase 2
0.6134	Remote Similarity	NPD5222	Approved
0.6134	Remote Similarity	NPD4697	Phase 3
0.6134	Remote Similarity	NPD5221	Approved
0.6134	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4767	Approved
0.6129	Remote Similarity	NPD4768	Approved
0.6115	Remote Similarity	NPD8338	Approved
0.6115	Remote Similarity	NPD6845	Suspended
0.6107	Remote Similarity	NPD6335	Approved
0.6098	Remote Similarity	NPD5174	Approved
0.6098	Remote Similarity	NPD5175	Approved
0.6094	Remote Similarity	NPD6053	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data