NPASS Compound

Structure

CID143446 OpenBabel06191715502D 34 36 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 8 31 1 0 0 0 0 9 12 2 0 0 0 0 10 7 1 1 0 0 0 10 13 1 0 0 0 0 10 32 1 0 0 0 0 11 8 1 1 0 0 0 11 14 1 0 0 0 0 11 33 1 0 0 0 0 12 19 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 6 0 0 0 14 16 1 0 0 0 0 14 25 1 6 0 0 0 15 17 1 0 0 0 0 15 26 1 1 0 0 0 16 18 1 0 0 0 0 16 27 1 1 0 0 0 17 20 1 0 0 0 0 17 28 1 6 0 0 0 18 21 1 0 0 0 0 18 29 1 6 0 0 0 19 30 2 0 0 0 0 19 34 1 0 0 0 0 20 31 1 1 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 21 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.22
Volume:	463.609
LogP:	-0.16
LogD:	0.111
LogS:	-2.186
# Rotatable Bonds:	7
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	4.703
Fsp3:	0.864
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.992
MDCK Permeability:	8.729934052098542e-05
Pgp-inhibitor:	0.862
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.972
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	61.28941345214844%
Volume Distribution (VD):	0.69
Pgp-substrate:	27.598169326782227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.178
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	1.014
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.125
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC143446

Natural Product ID:	NPC143446
*Common Name:**	Jasminoside S
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] 2,6,6-trimethylcyclohexene-1-carboxylate
Synonyms:	jasminoside S
Standard InCHIKey:	URTXXFGOVQACIC-NQAKZDGPSA-N
Standard InCHI:	InChI=1S/C22H36O12/c1-9-5-4-6-22(2,3)12(9)19(30)34-21-18(29)16(27)14(25)11(33-21)8-31-20-17(28)15(26)13(24)10(7-23)32-20/h10-11,13-18,20-21,23-29H,4-8H2,1-3H3/t10-,11-,13-,14-,15+,16+,17-,18-,20-,21+/m1/s1
SMILES:	CC1=C(C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O2)O)O)O)C(C)(C)CCC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2316921
PubChem CID:	71552547
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
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[512831]

☑ 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 NPC143446 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	231
0.1-0.2	1455
0.2-0.3	4804
0.3-0.4	9669
0.4-0.5	11950
0.5-0.6	7829
0.6-0.7	5499
0.7-0.8	1183
0.8-0.85	62
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8614	High Similarity	NPC219900
0.8614	High Similarity	NPC177524
0.8614	High Similarity	NPC392
0.8557	High Similarity	NPC56071
0.8557	High Similarity	NPC198422
0.8557	High Similarity	NPC70733
0.8557	High Similarity	NPC40182
0.8526	High Similarity	NPC294293
0.8485	Intermediate Similarity	NPC201191
0.8421	Intermediate Similarity	NPC320089
0.84	Intermediate Similarity	NPC309398
0.83	Intermediate Similarity	NPC223834
0.8269	Intermediate Similarity	NPC83005
0.8265	Intermediate Similarity	NPC278506
0.8247	Intermediate Similarity	NPC108141
0.8235	Intermediate Similarity	NPC476740
0.8235	Intermediate Similarity	NPC476738
0.8218	Intermediate Similarity	NPC473816
0.8218	Intermediate Similarity	NPC474581
0.8218	Intermediate Similarity	NPC475367
0.8148	Intermediate Similarity	NPC474483
0.8144	Intermediate Similarity	NPC25701
0.8144	Intermediate Similarity	NPC2003
0.8119	Intermediate Similarity	NPC121423
0.8077	Intermediate Similarity	NPC473807
0.8077	Intermediate Similarity	NPC193765
0.8073	Intermediate Similarity	NPC291564
0.8058	Intermediate Similarity	NPC82251
0.8041	Intermediate Similarity	NPC238090
0.8041	Intermediate Similarity	NPC472196
0.8041	Intermediate Similarity	NPC472195
0.8039	Intermediate Similarity	NPC151516
0.8037	Intermediate Similarity	NPC311592
0.8037	Intermediate Similarity	NPC474410
0.8037	Intermediate Similarity	NPC293658
0.8037	Intermediate Similarity	NPC75167
0.8021	Intermediate Similarity	NPC202886
0.802	Intermediate Similarity	NPC198992
0.802	Intermediate Similarity	NPC280991
0.8018	Intermediate Similarity	NPC476204
0.8018	Intermediate Similarity	NPC170084
0.8	Intermediate Similarity	NPC232258
0.8	Intermediate Similarity	NPC81483
0.8	Intermediate Similarity	NPC61630
0.8	Intermediate Similarity	NPC307517
0.8	Intermediate Similarity	NPC472015
0.8	Intermediate Similarity	NPC169468
0.7982	Intermediate Similarity	NPC473405
0.798	Intermediate Similarity	NPC54731
0.7963	Intermediate Similarity	NPC181145
0.7959	Intermediate Similarity	NPC159698
0.7941	Intermediate Similarity	NPC313569
0.7938	Intermediate Similarity	NPC472197
0.7938	Intermediate Similarity	NPC477749
0.7928	Intermediate Similarity	NPC476150
0.7928	Intermediate Similarity	NPC476127
0.7928	Intermediate Similarity	NPC48692
0.7917	Intermediate Similarity	NPC477748
0.7909	Intermediate Similarity	NPC471548
0.79	Intermediate Similarity	NPC155319
0.79	Intermediate Similarity	NPC96597
0.79	Intermediate Similarity	NPC239547
0.79	Intermediate Similarity	NPC91197
0.79	Intermediate Similarity	NPC309503
0.79	Intermediate Similarity	NPC125551
0.7885	Intermediate Similarity	NPC239961
0.7857	Intermediate Similarity	NPC129434
0.7843	Intermediate Similarity	NPC154127
0.7838	Intermediate Similarity	NPC122971
0.781	Intermediate Similarity	NPC293512
0.78	Intermediate Similarity	NPC306041
0.7778	Intermediate Similarity	NPC474554
0.7778	Intermediate Similarity	NPC477253
0.7778	Intermediate Similarity	NPC471967
0.7778	Intermediate Similarity	NPC477348
0.7778	Intermediate Similarity	NPC174836
0.7778	Intermediate Similarity	NPC238264
0.7778	Intermediate Similarity	NPC477345
0.7768	Intermediate Similarity	NPC470312
0.7767	Intermediate Similarity	NPC473596
0.7766	Intermediate Similarity	NPC288471
0.7757	Intermediate Similarity	NPC78046
0.7757	Intermediate Similarity	NPC279554
0.7757	Intermediate Similarity	NPC475296
0.7757	Intermediate Similarity	NPC59804
0.7757	Intermediate Similarity	NPC270667
0.7757	Intermediate Similarity	NPC235014
0.7757	Intermediate Similarity	NPC90856
0.7757	Intermediate Similarity	NPC136877
0.7757	Intermediate Similarity	NPC29069
0.7757	Intermediate Similarity	NPC174679
0.7757	Intermediate Similarity	NPC474589
0.7757	Intermediate Similarity	NPC269095
0.7757	Intermediate Similarity	NPC127056
0.7757	Intermediate Similarity	NPC164194
0.7757	Intermediate Similarity	NPC56713
0.7755	Intermediate Similarity	NPC472199
0.7755	Intermediate Similarity	NPC477349
0.7748	Intermediate Similarity	NPC473828
0.7748	Intermediate Similarity	NPC13710
0.7748	Intermediate Similarity	NPC234522
0.7748	Intermediate Similarity	NPC473617
0.7739	Intermediate Similarity	NPC297950
0.7736	Intermediate Similarity	NPC272576
0.7736	Intermediate Similarity	NPC285576
0.7736	Intermediate Similarity	NPC473288
0.7736	Intermediate Similarity	NPC325054
0.7723	Intermediate Similarity	NPC474194
0.7723	Intermediate Similarity	NPC266842
0.7714	Intermediate Similarity	NPC85670
0.7706	Intermediate Similarity	NPC473159
0.7706	Intermediate Similarity	NPC264153
0.77	Intermediate Similarity	NPC469543
0.7685	Intermediate Similarity	NPC179434
0.7685	Intermediate Similarity	NPC30397
0.7685	Intermediate Similarity	NPC164419
0.7685	Intermediate Similarity	NPC235841
0.7685	Intermediate Similarity	NPC473481
0.7685	Intermediate Similarity	NPC211798
0.7685	Intermediate Similarity	NPC297208
0.7685	Intermediate Similarity	NPC477073
0.7685	Intermediate Similarity	NPC108748
0.7679	Intermediate Similarity	NPC477071
0.7672	Intermediate Similarity	NPC470516
0.767	Intermediate Similarity	NPC471637
0.767	Intermediate Similarity	NPC154132
0.767	Intermediate Similarity	NPC2313
0.767	Intermediate Similarity	NPC57586
0.767	Intermediate Similarity	NPC475655
0.767	Intermediate Similarity	NPC476611
0.767	Intermediate Similarity	NPC475157
0.7664	Intermediate Similarity	NPC137917
0.7664	Intermediate Similarity	NPC31522
0.7664	Intermediate Similarity	NPC57362
0.7664	Intermediate Similarity	NPC306746
0.7664	Intermediate Similarity	NPC167383
0.7664	Intermediate Similarity	NPC477069
0.7664	Intermediate Similarity	NPC118225
0.7664	Intermediate Similarity	NPC477070
0.7664	Intermediate Similarity	NPC204407
0.7664	Intermediate Similarity	NPC237503
0.766	Intermediate Similarity	NPC470313
0.766	Intermediate Similarity	NPC156089
0.766	Intermediate Similarity	NPC38295
0.766	Intermediate Similarity	NPC473500
0.7658	Intermediate Similarity	NPC473968
0.7658	Intermediate Similarity	NPC309433
0.7658	Intermediate Similarity	NPC471547
0.7658	Intermediate Similarity	NPC477252
0.7652	Intermediate Similarity	NPC318135
0.7647	Intermediate Similarity	NPC222303
0.7642	Intermediate Similarity	NPC472390
0.7634	Intermediate Similarity	NPC16090
0.7629	Intermediate Similarity	NPC248312
0.7629	Intermediate Similarity	NPC471755
0.7629	Intermediate Similarity	NPC471756
0.7624	Intermediate Similarity	NPC255410
0.7624	Intermediate Similarity	NPC476066
0.7624	Intermediate Similarity	NPC475593
0.7624	Intermediate Similarity	NPC475164
0.7624	Intermediate Similarity	NPC475375
0.7624	Intermediate Similarity	NPC473765
0.7624	Intermediate Similarity	NPC473605
0.7624	Intermediate Similarity	NPC256230
0.7624	Intermediate Similarity	NPC475525
0.7624	Intermediate Similarity	NPC475241
0.7624	Intermediate Similarity	NPC240673
0.7624	Intermediate Similarity	NPC475540
0.7624	Intermediate Similarity	NPC17578
0.7619	Intermediate Similarity	NPC223741
0.7619	Intermediate Similarity	NPC472748
0.7619	Intermediate Similarity	NPC469869
0.7619	Intermediate Similarity	NPC470768
0.7615	Intermediate Similarity	NPC139044
0.7615	Intermediate Similarity	NPC161434
0.7615	Intermediate Similarity	NPC109079
0.7615	Intermediate Similarity	NPC257468
0.7615	Intermediate Similarity	NPC80843
0.7615	Intermediate Similarity	NPC475516
0.7615	Intermediate Similarity	NPC104400
0.7615	Intermediate Similarity	NPC10320
0.7615	Intermediate Similarity	NPC79718
0.7615	Intermediate Similarity	NPC139894
0.7615	Intermediate Similarity	NPC256798
0.7615	Intermediate Similarity	NPC101744
0.7615	Intermediate Similarity	NPC469946
0.7615	Intermediate Similarity	NPC473383
0.7615	Intermediate Similarity	NPC471383
0.7615	Intermediate Similarity	NPC104071
0.7615	Intermediate Similarity	NPC195132
0.7615	Intermediate Similarity	NPC276093
0.7615	Intermediate Similarity	NPC233003
0.7615	Intermediate Similarity	NPC473373
0.7615	Intermediate Similarity	NPC475504
0.7615	Intermediate Similarity	NPC128925
0.7615	Intermediate Similarity	NPC1046
0.7615	Intermediate Similarity	NPC102439
0.7615	Intermediate Similarity	NPC324875
0.7615	Intermediate Similarity	NPC292677
0.7607	Intermediate Similarity	NPC472269

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 NPC143446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1831
0.2-0.3	3797
0.3-0.4	2156
0.4-0.5	692
0.5-0.6	321
0.6-0.7	134
0.7-0.8	9
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8614	High Similarity	NPD6686	Approved
0.8021	Intermediate Similarity	NPD6698	Approved
0.8021	Intermediate Similarity	NPD46	Approved
0.7664	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6412	Phase 2
0.7476	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7507	Approved
0.7387	Intermediate Similarity	NPD8133	Approved
0.7364	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8328	Phase 3
0.725	Intermediate Similarity	NPD7319	Approved
0.7241	Intermediate Similarity	NPD8515	Approved
0.7241	Intermediate Similarity	NPD8513	Phase 3
0.7241	Intermediate Similarity	NPD8517	Approved
0.7241	Intermediate Similarity	NPD8516	Approved
0.7216	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8294	Approved
0.7155	Intermediate Similarity	NPD8377	Approved
0.713	Intermediate Similarity	NPD7328	Approved
0.713	Intermediate Similarity	NPD7327	Approved
0.7117	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8380	Approved
0.7094	Intermediate Similarity	NPD8296	Approved
0.7094	Intermediate Similarity	NPD8033	Approved
0.7094	Intermediate Similarity	NPD8379	Approved
0.7094	Intermediate Similarity	NPD7503	Approved
0.7094	Intermediate Similarity	NPD8335	Approved
0.7094	Intermediate Similarity	NPD8378	Approved
0.7069	Intermediate Similarity	NPD7516	Approved
0.6975	Remote Similarity	NPD7830	Approved
0.6975	Remote Similarity	NPD7829	Approved
0.6961	Remote Similarity	NPD7838	Discovery
0.6893	Remote Similarity	NPD7983	Approved
0.6847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7638	Approved
0.6759	Remote Similarity	NPD7640	Approved
0.6759	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD7642	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6612	Remote Similarity	NPD8080	Discontinued
0.661	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8451	Approved
0.6571	Remote Similarity	NPD6411	Approved
0.6555	Remote Similarity	NPD7641	Discontinued
0.6552	Remote Similarity	NPD6053	Discontinued
0.6549	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8448	Approved
0.6532	Remote Similarity	NPD8293	Discontinued
0.6529	Remote Similarity	NPD8444	Approved
0.6514	Remote Similarity	NPD4225	Approved
0.6509	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD5778	Approved
0.6508	Remote Similarity	NPD8390	Approved
0.6508	Remote Similarity	NPD8392	Approved
0.6508	Remote Similarity	NPD8391	Approved
0.6491	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7839	Suspended
0.648	Remote Similarity	NPD7736	Approved
0.6475	Remote Similarity	NPD6370	Approved
0.6471	Remote Similarity	NPD7115	Discovery
0.6458	Remote Similarity	NPD8039	Approved
0.641	Remote Similarity	NPD6882	Approved
0.6396	Remote Similarity	NPD5344	Discontinued
0.6393	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6101	Approved
0.6381	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8299	Approved
0.6371	Remote Similarity	NPD8340	Approved
0.6371	Remote Similarity	NPD7492	Approved
0.6371	Remote Similarity	NPD8342	Approved
0.6371	Remote Similarity	NPD8341	Approved
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6009	Approved
0.632	Remote Similarity	NPD6616	Approved
0.6311	Remote Similarity	NPD6054	Approved
0.6311	Remote Similarity	NPD6319	Approved
0.6311	Remote Similarity	NPD6059	Approved
0.6296	Remote Similarity	NPD7748	Approved
0.629	Remote Similarity	NPD6067	Discontinued
0.6273	Remote Similarity	NPD6084	Phase 2
0.6273	Remote Similarity	NPD6083	Phase 2
0.6273	Remote Similarity	NPD7902	Approved
0.6271	Remote Similarity	NPD8297	Approved
0.627	Remote Similarity	NPD7078	Approved
0.6262	Remote Similarity	NPD7515	Phase 2
0.6228	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4632	Approved
0.6204	Remote Similarity	NPD6399	Phase 3
0.6202	Remote Similarity	NPD7260	Phase 2
0.6174	Remote Similarity	NPD6402	Approved
0.6174	Remote Similarity	NPD5739	Approved
0.6174	Remote Similarity	NPD7128	Approved
0.6174	Remote Similarity	NPD6675	Approved
0.6168	Remote Similarity	NPD5785	Approved
0.6154	Remote Similarity	NPD6373	Approved
0.6154	Remote Similarity	NPD6845	Suspended
0.6154	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD6372	Approved
0.6129	Remote Similarity	NPD6016	Approved
0.6129	Remote Similarity	NPD6015	Approved
0.6117	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7154	Phase 3
0.6117	Remote Similarity	NPD3669	Approved
0.6111	Remote Similarity	NPD7637	Suspended
0.6095	Remote Similarity	NPD7334	Approved
0.6095	Remote Similarity	NPD7521	Approved
0.6095	Remote Similarity	NPD6409	Approved
0.6095	Remote Similarity	NPD5330	Approved
0.6095	Remote Similarity	NPD7146	Approved
0.6095	Remote Similarity	NPD6684	Approved
0.6094	Remote Similarity	NPD8337	Approved
0.6094	Remote Similarity	NPD8336	Approved
0.6091	Remote Similarity	NPD5695	Phase 3
0.6091	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.609	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5988	Approved
0.6068	Remote Similarity	NPD7320	Approved
0.6068	Remote Similarity	NPD6899	Approved
0.6068	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD8083	Approved
0.6053	Remote Similarity	NPD8084	Approved
0.6053	Remote Similarity	NPD8085	Approved
0.6053	Remote Similarity	NPD8086	Approved
0.6053	Remote Similarity	NPD8138	Approved
0.6053	Remote Similarity	NPD8139	Approved
0.6053	Remote Similarity	NPD8082	Approved
0.605	Remote Similarity	NPD6650	Approved
0.605	Remote Similarity	NPD6649	Approved
0.604	Remote Similarity	NPD7329	Approved
0.6018	Remote Similarity	NPD6648	Approved
0.6015	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6921	Approved
0.6	Remote Similarity	NPD8276	Approved
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD8275	Approved
0.6	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5701	Approved
0.5983	Remote Similarity	NPD5697	Approved
0.5981	Remote Similarity	NPD5737	Approved
0.5981	Remote Similarity	NPD6672	Approved
0.5981	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6903	Approved
0.5966	Remote Similarity	NPD7102	Approved
0.5966	Remote Similarity	NPD7290	Approved
0.5966	Remote Similarity	NPD6883	Approved
0.5962	Remote Similarity	NPD6110	Phase 1
0.5948	Remote Similarity	NPD8081	Approved
0.5941	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.594	Remote Similarity	NPD8415	Approved
0.5935	Remote Similarity	NPD7500	Approved
0.5929	Remote Similarity	NPD5696	Approved
0.5922	Remote Similarity	NPD1780	Approved
0.5922	Remote Similarity	NPD1779	Approved
0.5917	Remote Similarity	NPD6869	Approved
0.5917	Remote Similarity	NPD6617	Approved
0.5917	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD8130	Phase 1
0.5917	Remote Similarity	NPD6847	Approved
0.5906	Remote Similarity	NPD7604	Phase 2
0.5905	Remote Similarity	NPD3133	Approved
0.5905	Remote Similarity	NPD3665	Phase 1
0.5905	Remote Similarity	NPD3666	Approved
0.5897	Remote Similarity	NPD8393	Approved
0.5888	Remote Similarity	NPD4250	Approved
0.5888	Remote Similarity	NPD4251	Approved
0.5882	Remote Similarity	NPD6012	Approved
0.5882	Remote Similarity	NPD6013	Approved
0.5882	Remote Similarity	NPD6014	Approved
0.5878	Remote Similarity	NPD6914	Discontinued
0.5873	Remote Similarity	NPD8269	Approved
0.5873	Remote Similarity	NPD8267	Approved
0.5873	Remote Similarity	NPD5983	Phase 2
0.5873	Remote Similarity	NPD8266	Approved
0.5873	Remote Similarity	NPD8268	Approved
0.5865	Remote Similarity	NPD6435	Approved
0.5849	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8140	Approved
0.5847	Remote Similarity	NPD8307	Discontinued
0.5846	Remote Similarity	NPD6033	Approved
0.5833	Remote Similarity	NPD6421	Discontinued
0.5825	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5693	Phase 1
0.5816	Remote Similarity	NPD7625	Phase 1
0.5814	Remote Similarity	NPD8273	Phase 1
0.5814	Remote Similarity	NPD6336	Discontinued
0.581	Remote Similarity	NPD5362	Discontinued
0.5798	Remote Similarity	NPD6011	Approved
0.5794	Remote Similarity	NPD3618	Phase 1
0.5794	Remote Similarity	NPD4249	Approved
0.5794	Remote Similarity	NPD5279	Phase 3
0.5785	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5328	Approved
0.578	Remote Similarity	NPD4753	Phase 2

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