NPASS Compound

Structure

CID276298 OpenBabel06191716082D 36 40 0 0 1 0 0 0 0 0999 V2000 0.2514 3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6146 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5429 -2.1083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8108 1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4062 0.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2514 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5429 -1.1083 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9448 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6146 1.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4089 -0.6083 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9448 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4089 0.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0787 3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5429 0.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2127 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4807 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6768 0.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2127 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4089 -2.6083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9349 0.0982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9727 1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2749 -1.1083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8108 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2749 0.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0787 4.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5429 1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3467 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4807 3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8108 0.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6768 -0.6083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0787 1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3467 1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 31 1 0 0 0 0 3 22 1 0 0 0 0 4 32 1 0 0 0 0 5 23 1 0 0 0 0 6 1 1 1 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 3 1 6 0 0 0 7 11 1 0 0 0 0 7 33 1 0 0 0 0 8 4 1 6 0 0 0 8 12 1 0 0 0 0 8 34 1 0 0 0 0 9 18 1 0 0 0 0 9 21 1 1 0 0 0 10 17 1 0 0 0 0 10 24 1 6 0 0 0 11 13 1 0 0 0 0 11 25 1 6 0 0 0 12 14 1 0 0 0 0 12 26 1 1 0 0 0 13 15 1 0 0 0 0 13 27 1 6 0 0 0 14 16 1 0 0 0 0 14 28 1 6 0 0 0 15 19 1 0 0 0 0 15 29 1 1 0 0 0 16 20 1 0 0 0 0 16 30 1 1 0 0 0 17 21 1 1 0 0 0 17 36 1 0 0 0 0 18 31 1 0 0 0 0 18 35 1 6 0 0 0 19 32 1 1 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 20 35 1 6 0 0 0 21 5 1 1 0 0 0 21 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.17
Volume:	458.207
LogP:	-2.162
LogD:	-1.179
LogS:	-1.572
# Rotatable Bonds:	7
TPSA:	240.75
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.141
Synthetic Accessibility Score:	5.438
Fsp3:	0.905
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:	-6.578
MDCK Permeability:	0.0001945473486557603
Pgp-inhibitor:	0.002
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.97
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	20.24872398376465%
Volume Distribution (VD):	0.377
Pgp-substrate:	49.21088409423828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	0.893
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.339
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.723
Carcinogencity:	0.324
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC276298

Natural Product ID:	NPC276298
*Common Name:**	Rehmannioside A
IUPAC Name:	(2S,3R,4S,5R,6R)-2-[[(2R,3S,4S,5R,6S)-6-[[(1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-1a-(hydroxymethyl)-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-2-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	DTNSOISBYQKHCS-XTOBSYSVSA-N
Standard InCHI:	InChI=1S/C21H32O15/c22-3-7-11(25)13(27)15(29)19(33-7)32-4-8-12(26)14(28)16(30)20(34-8)35-18-9-6(1-2-31-18)10(24)17-21(9,5-23)36-17/h1-2,6-20,22-30H,3-5H2/t6-,7-,8-,9-,10+,11+,12-,13+,14+,15-,16-,17+,18+,19+,20+,21-/m1/s1
SMILES:	OC[C@H]1O[C@H](OC[C@H]2O[C@@H](O[C@@H]3OC=C[C@@H]4[C@H]3[C@@]3(CO)O[C@H]3[C@H]4O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3810015
PubChem CID:	6325881
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO40316	Rehmannia chingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26859776]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[549431]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[549431]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[549431]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[549431]

☑ 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 NPC276298 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	229
0.1-0.2	2371
0.2-0.3	9318
0.3-0.4	14496
0.4-0.5	8998
0.5-0.6	5671
0.6-0.7	1520
0.7-0.8	72
0.8-0.85	13
0.85-0.9	3
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC22918
0.9529	High Similarity	NPC258501
0.9419	High Similarity	NPC148534
0.8953	High Similarity	NPC98276
0.8953	High Similarity	NPC259296
0.8817	High Similarity	NPC470684
0.8817	High Similarity	NPC470683
0.875	High Similarity	NPC149018
0.875	High Similarity	NPC171484
0.8667	High Similarity	NPC50464
0.8478	Intermediate Similarity	NPC473150
0.8478	Intermediate Similarity	NPC294643
0.8478	Intermediate Similarity	NPC274274
0.8261	Intermediate Similarity	NPC93190
0.8	Intermediate Similarity	NPC280390
0.7677	Intermediate Similarity	NPC86843
0.7653	Intermediate Similarity	NPC6765
0.7653	Intermediate Similarity	NPC93869
0.7647	Intermediate Similarity	NPC329834
0.7614	Intermediate Similarity	NPC279575
0.7576	Intermediate Similarity	NPC284063
0.7556	Intermediate Similarity	NPC170595
0.7551	Intermediate Similarity	NPC274588
0.7547	Intermediate Similarity	NPC193741
0.7527	Intermediate Similarity	NPC220167
0.7527	Intermediate Similarity	NPC136699
0.7526	Intermediate Similarity	NPC235051
0.75	Intermediate Similarity	NPC474569
0.75	Intermediate Similarity	NPC76486
0.7451	Intermediate Similarity	NPC476228
0.7451	Intermediate Similarity	NPC216911
0.7407	Intermediate Similarity	NPC475851
0.7407	Intermediate Similarity	NPC475924
0.74	Intermediate Similarity	NPC170527
0.7353	Intermediate Similarity	NPC476211
0.7353	Intermediate Similarity	NPC476320
0.7353	Intermediate Similarity	NPC91497
0.7347	Intermediate Similarity	NPC66504
0.7333	Intermediate Similarity	NPC127235
0.7312	Intermediate Similarity	NPC20072
0.729	Intermediate Similarity	NPC42482
0.729	Intermediate Similarity	NPC40440
0.7282	Intermediate Similarity	NPC476230
0.7282	Intermediate Similarity	NPC27474
0.7273	Intermediate Similarity	NPC470659
0.7273	Intermediate Similarity	NPC470660
0.7264	Intermediate Similarity	NPC148270
0.7264	Intermediate Similarity	NPC80338
0.7264	Intermediate Similarity	NPC197813
0.7248	Intermediate Similarity	NPC19888
0.7238	Intermediate Similarity	NPC312774
0.7238	Intermediate Similarity	NPC475521
0.7216	Intermediate Similarity	NPC248312
0.7212	Intermediate Similarity	NPC272015
0.7196	Intermediate Similarity	NPC7213
0.7184	Intermediate Similarity	NPC244878
0.7172	Intermediate Similarity	NPC48463
0.717	Intermediate Similarity	NPC473923
0.717	Intermediate Similarity	NPC26798
0.717	Intermediate Similarity	NPC473476
0.717	Intermediate Similarity	NPC181845
0.717	Intermediate Similarity	NPC242748
0.717	Intermediate Similarity	NPC170432
0.7168	Intermediate Similarity	NPC219656
0.7156	Intermediate Similarity	NPC477032
0.7156	Intermediate Similarity	NPC197231
0.7156	Intermediate Similarity	NPC124677
0.7156	Intermediate Similarity	NPC477028
0.7143	Intermediate Similarity	NPC329704
0.7143	Intermediate Similarity	NPC37240
0.7143	Intermediate Similarity	NPC475928
0.7115	Intermediate Similarity	NPC20673
0.7115	Intermediate Similarity	NPC287539
0.7115	Intermediate Similarity	NPC31346
0.7115	Intermediate Similarity	NPC470168
0.7115	Intermediate Similarity	NPC3488
0.7103	Intermediate Similarity	NPC113044
0.7103	Intermediate Similarity	NPC94272
0.7103	Intermediate Similarity	NPC14704
0.7103	Intermediate Similarity	NPC161676
0.7103	Intermediate Similarity	NPC473469
0.7103	Intermediate Similarity	NPC283829
0.7103	Intermediate Similarity	NPC226642
0.7103	Intermediate Similarity	NPC230507
0.7103	Intermediate Similarity	NPC470432
0.7103	Intermediate Similarity	NPC305423
0.7091	Intermediate Similarity	NPC308140
0.7091	Intermediate Similarity	NPC254255
0.7087	Intermediate Similarity	NPC151093
0.7087	Intermediate Similarity	NPC158088
0.7087	Intermediate Similarity	NPC157739
0.708	Intermediate Similarity	NPC472080
0.7079	Intermediate Similarity	NPC248427
0.7075	Intermediate Similarity	NPC470885
0.7075	Intermediate Similarity	NPC187400
0.7075	Intermediate Similarity	NPC475365
0.7075	Intermediate Similarity	NPC474464
0.7075	Intermediate Similarity	NPC221562
0.7071	Intermediate Similarity	NPC307699
0.7069	Intermediate Similarity	NPC219804
0.7059	Intermediate Similarity	NPC161293
0.7059	Intermediate Similarity	NPC207617
0.7059	Intermediate Similarity	NPC472989
0.7048	Intermediate Similarity	NPC177013
0.7048	Intermediate Similarity	NPC35185
0.7048	Intermediate Similarity	NPC474730
0.7048	Intermediate Similarity	NPC4899
0.7048	Intermediate Similarity	NPC136816
0.7048	Intermediate Similarity	NPC304163
0.7043	Intermediate Similarity	NPC233500
0.7037	Intermediate Similarity	NPC98696
0.7037	Intermediate Similarity	NPC476538
0.7037	Intermediate Similarity	NPC476540
0.7037	Intermediate Similarity	NPC476539
0.7037	Intermediate Similarity	NPC472897
0.7037	Intermediate Similarity	NPC472896
0.7037	Intermediate Similarity	NPC476541
0.7037	Intermediate Similarity	NPC295980
0.7037	Intermediate Similarity	NPC110701
0.7037	Intermediate Similarity	NPC475634
0.7037	Intermediate Similarity	NPC235824
0.703	Intermediate Similarity	NPC63897
0.7027	Intermediate Similarity	NPC476546
0.7027	Intermediate Similarity	NPC287075
0.7019	Intermediate Similarity	NPC471247
0.7009	Intermediate Similarity	NPC309448
0.7009	Intermediate Similarity	NPC474015
0.7	Intermediate Similarity	NPC472987
0.7	Intermediate Similarity	NPC470748
0.7	Intermediate Similarity	NPC472125
0.7	Intermediate Similarity	NPC473021
0.7	Intermediate Similarity	NPC472126
0.7	Intermediate Similarity	NPC13193
0.7	Intermediate Similarity	NPC472124
0.699	Remote Similarity	NPC278939
0.699	Remote Similarity	NPC473555
0.699	Remote Similarity	NPC471770
0.699	Remote Similarity	NPC473890
0.699	Remote Similarity	NPC263674
0.699	Remote Similarity	NPC58267
0.699	Remote Similarity	NPC261372
0.699	Remote Similarity	NPC243728
0.6983	Remote Similarity	NPC196130
0.6981	Remote Similarity	NPC31907
0.6981	Remote Similarity	NPC286969
0.6981	Remote Similarity	NPC16520
0.6981	Remote Similarity	NPC120123
0.6981	Remote Similarity	NPC472252
0.6981	Remote Similarity	NPC189852
0.6981	Remote Similarity	NPC131479
0.6981	Remote Similarity	NPC473020
0.6981	Remote Similarity	NPC475701
0.6981	Remote Similarity	NPC157659
0.6981	Remote Similarity	NPC155010
0.6981	Remote Similarity	NPC8039
0.6981	Remote Similarity	NPC245280
0.6981	Remote Similarity	NPC211879
0.6981	Remote Similarity	NPC114874
0.6972	Remote Similarity	NPC244086
0.6972	Remote Similarity	NPC218571
0.6972	Remote Similarity	NPC208383
0.6972	Remote Similarity	NPC22779
0.6972	Remote Similarity	NPC475333
0.6972	Remote Similarity	NPC249265
0.6972	Remote Similarity	NPC84956
0.6972	Remote Similarity	NPC102016
0.6972	Remote Similarity	NPC472901
0.6972	Remote Similarity	NPC477809
0.6972	Remote Similarity	NPC477027
0.6972	Remote Similarity	NPC248746
0.6972	Remote Similarity	NPC150372
0.6972	Remote Similarity	NPC224098
0.6972	Remote Similarity	NPC70204
0.6972	Remote Similarity	NPC309278
0.6972	Remote Similarity	NPC475550
0.6972	Remote Similarity	NPC46190
0.6972	Remote Similarity	NPC95051
0.6972	Remote Similarity	NPC73243
0.6972	Remote Similarity	NPC232054
0.6972	Remote Similarity	NPC470433
0.6972	Remote Similarity	NPC476835
0.6972	Remote Similarity	NPC300557
0.6972	Remote Similarity	NPC474573
0.6972	Remote Similarity	NPC306131
0.6972	Remote Similarity	NPC171073
0.6972	Remote Similarity	NPC6806
0.6972	Remote Similarity	NPC194207
0.6972	Remote Similarity	NPC475670
0.6972	Remote Similarity	NPC477026
0.697	Remote Similarity	NPC104129
0.697	Remote Similarity	NPC249408
0.697	Remote Similarity	NPC299527
0.6964	Remote Similarity	NPC477810
0.6964	Remote Similarity	NPC32707
0.6964	Remote Similarity	NPC167183
0.6964	Remote Similarity	NPC208832
0.6961	Remote Similarity	NPC101051
0.6952	Remote Similarity	NPC88000
0.6952	Remote Similarity	NPC129372
0.6952	Remote Similarity	NPC4637

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 NPC276298 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	2777
0.2-0.3	4326
0.3-0.4	1220
0.4-0.5	386
0.5-0.6	237
0.6-0.7	19
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6752	Remote Similarity	NPD7503	Approved
0.661	Remote Similarity	NPD8033	Approved
0.6486	Remote Similarity	NPD6412	Phase 2
0.6442	Remote Similarity	NPD8171	Discontinued
0.6387	Remote Similarity	NPD8294	Approved
0.6387	Remote Similarity	NPD8377	Approved
0.6356	Remote Similarity	NPD7328	Approved
0.6356	Remote Similarity	NPD7327	Approved
0.6333	Remote Similarity	NPD8380	Approved
0.6333	Remote Similarity	NPD8335	Approved
0.6333	Remote Similarity	NPD8296	Approved
0.6333	Remote Similarity	NPD8379	Approved
0.6333	Remote Similarity	NPD8378	Approved
0.6303	Remote Similarity	NPD7516	Approved
0.6293	Remote Similarity	NPD8133	Approved
0.6275	Remote Similarity	NPD4251	Approved
0.6275	Remote Similarity	NPD4250	Approved
0.6176	Remote Similarity	NPD4249	Approved
0.6121	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7524	Approved
0.6016	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD6686	Approved
0.598	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8513	Phase 3
0.5932	Remote Similarity	NPD6053	Discontinued
0.59	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6695	Phase 3
0.5877	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7319	Approved
0.5856	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6054	Approved
0.5846	Remote Similarity	NPD8449	Approved
0.5843	Remote Similarity	NPD6123	Approved
0.5806	Remote Similarity	NPD8517	Approved
0.5806	Remote Similarity	NPD8516	Approved
0.5806	Remote Similarity	NPD8515	Approved
0.5802	Remote Similarity	NPD8450	Suspended
0.5794	Remote Similarity	NPD7838	Discovery
0.5794	Remote Similarity	NPD6698	Approved
0.5794	Remote Similarity	NPD46	Approved
0.5781	Remote Similarity	NPD7736	Approved
0.5773	Remote Similarity	NPD1810	Approved
0.5773	Remote Similarity	NPD1811	Approved
0.5765	Remote Similarity	NPD892	Phase 3
0.5765	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD893	Approved
0.5765	Remote Similarity	NPD888	Phase 3
0.5765	Remote Similarity	NPD891	Phase 3
0.5743	Remote Similarity	NPD4821	Approved
0.5743	Remote Similarity	NPD4820	Approved
0.5743	Remote Similarity	NPD4819	Approved
0.5743	Remote Similarity	NPD4822	Approved
0.5743	Remote Similarity	NPD6928	Phase 2
0.5726	Remote Similarity	NPD6059	Approved
0.5703	Remote Similarity	NPD8293	Discontinued
0.57	Remote Similarity	NPD4268	Approved
0.57	Remote Similarity	NPD4271	Approved
0.568	Remote Similarity	NPD6015	Approved
0.568	Remote Similarity	NPD6016	Approved
0.5669	Remote Similarity	NPD7492	Approved
0.566	Remote Similarity	NPD7750	Discontinued
0.5657	Remote Similarity	NPD6933	Approved
0.5648	Remote Similarity	NPD3168	Discontinued
0.5647	Remote Similarity	NPD2269	Approved
0.5635	Remote Similarity	NPD5988	Approved
0.5631	Remote Similarity	NPD6435	Approved
0.5625	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6616	Approved
0.5614	Remote Similarity	NPD5344	Discontinued
0.561	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6319	Approved
0.56	Remote Similarity	NPD6932	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