NPASS Compound

Structure

NPC98193 OpenBabel07101719252D 36 40 0 0 1 0 0 0 0 0999 V2000 -3.1650 1.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0649 -1.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7450 -0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 -1.1499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5772 0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7969 0.6855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9309 1.1855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7969 -2.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1988 -0.8145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9309 -1.8145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3328 -0.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6629 -0.8145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9909 2.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4307 2.6418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6045 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7969 -0.3145 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6629 -1.8145 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0649 0.6855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0649 -0.3145 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1988 1.1855 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6386 1.6637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9964 2.2682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9309 -0.8145 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3328 0.6855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5897 1.3546 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5204 2.9508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2737 -2.1009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5290 -2.3145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4964 3.1342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4894 2.1160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 0.6855 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 5 1 0 0 0 0 3 27 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 18 2 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 14 30 1 0 0 0 0 15 28 1 0 0 0 0 15 31 1 0 0 0 0 16 26 1 1 0 0 0 17 32 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 24 1 0 0 0 0 19 28 1 1 0 0 0 20 26 1 1 0 0 0 21 27 1 1 0 0 0 22 14 1 1 0 0 0 22 29 1 0 0 0 0 23 29 1 1 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 24 34 1 6 0 0 0 25 22 1 6 0 0 0 25 36 1 0 0 0 0 26 2 1 1 0 0 0 27 29 1 6 0 0 0 28 4 1 1 0 0 0 28 36 1 0 0 0 0 29 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.34
Volume:	526.253
LogP:	2.61
LogD:	2.679
LogS:	-3.296
# Rotatable Bonds:	5
TPSA:	130.61
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.314
Synthetic Accessibility Score:	5.714
Fsp3:	0.931
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:	-5.111
MDCK Permeability:	0.00018865067977458239
Pgp-inhibitor:	0.896
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.73
30% Bioavailability (F30%):	0.699

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	59.91338348388672%
Volume Distribution (VD):	0.523
Pgp-substrate:	17.106521606445312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.662
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.639
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	8.165
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.202
Carcinogencity:	0.663
Eye Corrosion:	0.035
Eye Irritation:	0.022
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC98193

Natural Product ID:	NPC98193
*Common Name:**	Ajugasalicigenin
IUPAC Name:	(3S,5S,9R,10S,13S,14S,16S,17S)-17-[(1R)-1-[(2S,3S,4S,5S)-4-ethyl-3-hydroxy-5-(hydroxymethyl)-5-methyloxolan-2-yl]-2-hydroxyethyl]-10,13-dimethyl-1,2,3,4,5,6,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,16,17-triol
Synonyms:	ajugasalicigenin
Standard InCHIKey:	WTAODDALTKKQHM-LKMZUHJLSA-N
Standard InCHI:	InChI=1S/C29H48O7/c1-5-19-24(34)25(36-28(19,4)15-31)22(14-30)29(35)23(33)13-21-18-7-6-16-12-17(32)8-10-26(16,2)20(18)9-11-27(21,29)3/h7,16-17,19-25,30-35H,5-6,8-15H2,1-4H3/t16-,17-,19-,20-,21-,22+,23-,24-,25-,26-,27-,28+,29+/m0/s1
SMILES:	OC[C@@H]([C@@]1(O)[C@@H](O)C[C@@H]2[C@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2)O)[C@@H]1O[C@]([C@H]([C@@H]1O)CC)(C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512780
PubChem CID:	11060270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO21740	Ajuga salicifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713393]
NPO21740	Ajuga salicifolia	Species	Lamiaceae	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
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[560295]

☑ 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 NPC98193 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	205
0.1-0.2	1535
0.2-0.3	6025
0.3-0.4	14951
0.4-0.5	7751
0.5-0.6	5484
0.6-0.7	5080
0.7-0.8	1543
0.8-0.85	107
0.85-0.9	14
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9053	High Similarity	NPC475701
0.9032	High Similarity	NPC309493
0.9	High Similarity	NPC210268
0.8958	High Similarity	NPC474464
0.8866	High Similarity	NPC474015
0.8866	High Similarity	NPC26798
0.883	High Similarity	NPC5358
0.883	High Similarity	NPC216260
0.8763	High Similarity	NPC471111
0.8652	High Similarity	NPC125399
0.8652	High Similarity	NPC201273
0.8636	High Similarity	NPC124172
0.8621	High Similarity	NPC470614
0.8621	High Similarity	NPC30166
0.8621	High Similarity	NPC1272
0.86	High Similarity	NPC128133
0.8571	High Similarity	NPC105495
0.8571	High Similarity	NPC109744
0.8557	High Similarity	NPC22634
0.8556	High Similarity	NPC474657
0.8556	High Similarity	NPC186145
0.8542	High Similarity	NPC324598
0.8539	High Similarity	NPC474189
0.8539	High Similarity	NPC474349
0.8526	High Similarity	NPC475033
0.8526	High Similarity	NPC475032
0.8523	High Similarity	NPC110778
0.8523	High Similarity	NPC132635
0.8511	High Similarity	NPC8774
0.8478	Intermediate Similarity	NPC473956
0.8478	Intermediate Similarity	NPC475751
0.8478	Intermediate Similarity	NPC107189
0.8462	Intermediate Similarity	NPC473436
0.8462	Intermediate Similarity	NPC475664
0.8462	Intermediate Similarity	NPC474668
0.8454	Intermediate Similarity	NPC474022
0.8444	Intermediate Similarity	NPC24277
0.8444	Intermediate Similarity	NPC152808
0.8444	Intermediate Similarity	NPC293287
0.8444	Intermediate Similarity	NPC6605
0.8438	Intermediate Similarity	NPC275865
0.8431	Intermediate Similarity	NPC197231
0.8421	Intermediate Similarity	NPC288970
0.8421	Intermediate Similarity	NPC98457
0.8421	Intermediate Similarity	NPC227583
0.8421	Intermediate Similarity	NPC12103
0.8416	Intermediate Similarity	NPC42482
0.8416	Intermediate Similarity	NPC40440
0.8404	Intermediate Similarity	NPC127718
0.8404	Intermediate Similarity	NPC65402
0.84	Intermediate Similarity	NPC226642
0.8391	Intermediate Similarity	NPC26117
0.8387	Intermediate Similarity	NPC97404
0.8387	Intermediate Similarity	NPC41554
0.8384	Intermediate Similarity	NPC85593
0.8384	Intermediate Similarity	NPC31430
0.837	Intermediate Similarity	NPC470361
0.8352	Intermediate Similarity	NPC189777
0.835	Intermediate Similarity	NPC19888
0.8333	Intermediate Similarity	NPC177818
0.8333	Intermediate Similarity	NPC316604
0.8315	Intermediate Similarity	NPC477818
0.8315	Intermediate Similarity	NPC193870
0.8315	Intermediate Similarity	NPC141941
0.8315	Intermediate Similarity	NPC207013
0.83	Intermediate Similarity	NPC181845
0.83	Intermediate Similarity	NPC474569
0.8298	Intermediate Similarity	NPC242419
0.8298	Intermediate Similarity	NPC235126
0.8295	Intermediate Similarity	NPC70927
0.8283	Intermediate Similarity	NPC213190
0.828	Intermediate Similarity	NPC11216
0.828	Intermediate Similarity	NPC470832
0.828	Intermediate Similarity	NPC204188
0.828	Intermediate Similarity	NPC329596
0.828	Intermediate Similarity	NPC3345
0.828	Intermediate Similarity	NPC80561
0.828	Intermediate Similarity	NPC291484
0.8276	Intermediate Similarity	NPC328714
0.8276	Intermediate Similarity	NPC1319
0.8269	Intermediate Similarity	NPC178981
0.8265	Intermediate Similarity	NPC155974
0.8261	Intermediate Similarity	NPC2158
0.8261	Intermediate Similarity	NPC470542
0.8261	Intermediate Similarity	NPC133588
0.8252	Intermediate Similarity	NPC477032
0.8252	Intermediate Similarity	NPC477028
0.8252	Intermediate Similarity	NPC124677
0.8247	Intermediate Similarity	NPC476895
0.8242	Intermediate Similarity	NPC6391
0.8242	Intermediate Similarity	NPC121981
0.8242	Intermediate Similarity	NPC94462
0.8235	Intermediate Similarity	NPC476835
0.8222	Intermediate Similarity	NPC255882
0.8222	Intermediate Similarity	NPC127606
0.8222	Intermediate Similarity	NPC209802
0.8222	Intermediate Similarity	NPC475798
0.8218	Intermediate Similarity	NPC470432
0.8218	Intermediate Similarity	NPC14704
0.8218	Intermediate Similarity	NPC283829
0.8218	Intermediate Similarity	NPC230507
0.8218	Intermediate Similarity	NPC305423
0.8218	Intermediate Similarity	NPC113044
0.8218	Intermediate Similarity	NPC161676
0.8211	Intermediate Similarity	NPC144202
0.82	Intermediate Similarity	NPC475365
0.82	Intermediate Similarity	NPC471293
0.819	Intermediate Similarity	NPC32707
0.819	Intermediate Similarity	NPC167183
0.8182	Intermediate Similarity	NPC322313
0.8182	Intermediate Similarity	NPC102253
0.8182	Intermediate Similarity	NPC236237
0.8182	Intermediate Similarity	NPC236112
0.8182	Intermediate Similarity	NPC13554
0.8173	Intermediate Similarity	NPC254255
0.8173	Intermediate Similarity	NPC207251
0.8163	Intermediate Similarity	NPC208358
0.8161	Intermediate Similarity	NPC477522
0.8161	Intermediate Similarity	NPC87604
0.8152	Intermediate Similarity	NPC271967
0.8144	Intermediate Similarity	NPC476893
0.8144	Intermediate Similarity	NPC243728
0.8144	Intermediate Similarity	NPC210337
0.8144	Intermediate Similarity	NPC473890
0.8144	Intermediate Similarity	NPC476021
0.8144	Intermediate Similarity	NPC474994
0.8144	Intermediate Similarity	NPC261807
0.8144	Intermediate Similarity	NPC476040
0.8137	Intermediate Similarity	NPC98696
0.8137	Intermediate Similarity	NPC476541
0.8137	Intermediate Similarity	NPC476540
0.8137	Intermediate Similarity	NPC476539
0.8137	Intermediate Similarity	NPC476538
0.8132	Intermediate Similarity	NPC318390
0.8119	Intermediate Similarity	NPC242748
0.8111	Intermediate Similarity	NPC474634
0.8111	Intermediate Similarity	NPC211135
0.8111	Intermediate Similarity	NPC85095
0.8111	Intermediate Similarity	NPC216420
0.8111	Intermediate Similarity	NPC232023
0.8105	Intermediate Similarity	NPC27531
0.8105	Intermediate Similarity	NPC307776
0.8095	Intermediate Similarity	NPC79900
0.809	Intermediate Similarity	NPC470383
0.809	Intermediate Similarity	NPC474531
0.8085	Intermediate Similarity	NPC473269
0.8081	Intermediate Similarity	NPC88000
0.8081	Intermediate Similarity	NPC129372
0.8081	Intermediate Similarity	NPC472023
0.8081	Intermediate Similarity	NPC309425
0.8081	Intermediate Similarity	NPC476896
0.8081	Intermediate Similarity	NPC176406
0.8081	Intermediate Similarity	NPC4831
0.8081	Intermediate Similarity	NPC160734
0.8081	Intermediate Similarity	NPC475617
0.8081	Intermediate Similarity	NPC47566
0.8077	Intermediate Similarity	NPC13193
0.8077	Intermediate Similarity	NPC476547
0.8068	Intermediate Similarity	NPC80530
0.8068	Intermediate Similarity	NPC273410
0.8065	Intermediate Similarity	NPC22376
0.8061	Intermediate Similarity	NPC234287
0.8061	Intermediate Similarity	NPC158088
0.8061	Intermediate Similarity	NPC280825
0.8058	Intermediate Similarity	NPC150372
0.8058	Intermediate Similarity	NPC300557
0.8058	Intermediate Similarity	NPC218571
0.8058	Intermediate Similarity	NPC248746
0.8058	Intermediate Similarity	NPC46190
0.8058	Intermediate Similarity	NPC6806
0.8058	Intermediate Similarity	NPC84956
0.8058	Intermediate Similarity	NPC306131
0.8058	Intermediate Similarity	NPC102016
0.8058	Intermediate Similarity	NPC477026
0.8058	Intermediate Similarity	NPC22779
0.8058	Intermediate Similarity	NPC309278
0.8058	Intermediate Similarity	NPC95051
0.8058	Intermediate Similarity	NPC224098
0.8058	Intermediate Similarity	NPC171073
0.8058	Intermediate Similarity	NPC475333
0.8058	Intermediate Similarity	NPC475550
0.8058	Intermediate Similarity	NPC73243
0.8058	Intermediate Similarity	NPC249265
0.8058	Intermediate Similarity	NPC194207
0.8058	Intermediate Similarity	NPC477809
0.8058	Intermediate Similarity	NPC208383
0.8058	Intermediate Similarity	NPC477027
0.8058	Intermediate Similarity	NPC232054
0.8058	Intermediate Similarity	NPC470433
0.8058	Intermediate Similarity	NPC244086
0.8058	Intermediate Similarity	NPC475670
0.8058	Intermediate Similarity	NPC70204
0.8046	Intermediate Similarity	NPC130136
0.8046	Intermediate Similarity	NPC155986
0.8046	Intermediate Similarity	NPC198968
0.8046	Intermediate Similarity	NPC318495
0.8043	Intermediate Similarity	NPC71520
0.8043	Intermediate Similarity	NPC139724
0.8043	Intermediate Similarity	NPC269058
0.8043	Intermediate Similarity	NPC299068

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 NPC98193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1778
0.2-0.3	4448
0.3-0.4	1919
0.4-0.5	394
0.5-0.6	178
0.6-0.7	158
0.7-0.8	94
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
0.8182	Intermediate Similarity	NPD7525	Registered
0.7957	Intermediate Similarity	NPD7524	Approved
0.7931	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6942	Approved
0.7816	Intermediate Similarity	NPD7339	Approved
0.7766	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6695	Phase 3
0.7674	Intermediate Similarity	NPD4243	Approved
0.7658	Intermediate Similarity	NPD6054	Approved
0.7658	Intermediate Similarity	NPD6059	Approved
0.7528	Intermediate Similarity	NPD6933	Approved
0.7524	Intermediate Similarity	NPD6412	Phase 2
0.7522	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD4784	Approved
0.75	Intermediate Similarity	NPD4785	Approved
0.7477	Intermediate Similarity	NPD7328	Approved
0.7477	Intermediate Similarity	NPD4634	Approved
0.7477	Intermediate Similarity	NPD7327	Approved
0.7473	Intermediate Similarity	NPD7645	Phase 2
0.7453	Intermediate Similarity	NPD7320	Approved
0.7434	Intermediate Similarity	NPD6015	Approved
0.7434	Intermediate Similarity	NPD6016	Approved
0.7429	Intermediate Similarity	NPD6675	Approved
0.7429	Intermediate Similarity	NPD7128	Approved
0.7429	Intermediate Similarity	NPD6402	Approved
0.7429	Intermediate Similarity	NPD5739	Approved
0.7426	Intermediate Similarity	NPD4755	Approved
0.7411	Intermediate Similarity	NPD7516	Approved
0.7396	Intermediate Similarity	NPD7750	Discontinued
0.7391	Intermediate Similarity	NPD4748	Discontinued
0.7391	Intermediate Similarity	NPD7492	Approved
0.7391	Intermediate Similarity	NPD6930	Phase 2
0.7391	Intermediate Similarity	NPD6931	Approved
0.7374	Intermediate Similarity	NPD4202	Approved
0.7368	Intermediate Similarity	NPD5988	Approved
0.7345	Intermediate Similarity	NPD8377	Approved
0.7345	Intermediate Similarity	NPD8294	Approved
0.7345	Intermediate Similarity	NPD6319	Approved
0.7339	Intermediate Similarity	NPD8297	Approved
0.7328	Intermediate Similarity	NPD6616	Approved
0.7303	Intermediate Similarity	NPD6926	Approved
0.7303	Intermediate Similarity	NPD6924	Approved
0.729	Intermediate Similarity	NPD6881	Approved
0.729	Intermediate Similarity	NPD6899	Approved
0.7283	Intermediate Similarity	NPD6929	Approved
0.7282	Intermediate Similarity	NPD4700	Approved
0.7282	Intermediate Similarity	NPD4696	Approved
0.7282	Intermediate Similarity	NPD5285	Approved
0.7282	Intermediate Similarity	NPD5286	Approved
0.7281	Intermediate Similarity	NPD8033	Approved
0.7281	Intermediate Similarity	NPD8378	Approved
0.7281	Intermediate Similarity	NPD8296	Approved
0.7281	Intermediate Similarity	NPD8380	Approved
0.7281	Intermediate Similarity	NPD8379	Approved
0.7281	Intermediate Similarity	NPD8335	Approved
0.7273	Intermediate Similarity	NPD4632	Approved
0.7265	Intermediate Similarity	NPD7078	Approved
0.7265	Intermediate Similarity	NPD8293	Discontinued
0.7263	Intermediate Similarity	NPD4786	Approved
0.7255	Intermediate Similarity	NPD6083	Phase 2
0.7255	Intermediate Similarity	NPD6084	Phase 2
0.7253	Intermediate Similarity	NPD6932	Approved
0.7245	Intermediate Similarity	NPD4753	Phase 2
0.7222	Intermediate Similarity	NPD6372	Approved
0.7222	Intermediate Similarity	NPD4190	Phase 3
0.7222	Intermediate Similarity	NPD6373	Approved
0.7222	Intermediate Similarity	NPD5275	Approved
0.7203	Intermediate Similarity	NPD7736	Approved
0.72	Intermediate Similarity	NPD6399	Phase 3
0.7196	Intermediate Similarity	NPD5697	Approved
0.7196	Intermediate Similarity	NPD5701	Approved
0.7184	Intermediate Similarity	NPD7638	Approved
0.7156	Intermediate Similarity	NPD6883	Approved
0.7156	Intermediate Similarity	NPD7290	Approved
0.7156	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD5211	Phase 2
0.7143	Intermediate Similarity	NPD5225	Approved
0.7143	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD4633	Approved
0.713	Intermediate Similarity	NPD7503	Approved
0.7115	Intermediate Similarity	NPD7640	Approved
0.7115	Intermediate Similarity	NPD7639	Approved
0.7103	Intermediate Similarity	NPD6008	Approved
0.71	Intermediate Similarity	NPD7087	Discontinued
0.7097	Intermediate Similarity	NPD6683	Phase 2
0.7097	Intermediate Similarity	NPD4195	Approved
0.7091	Intermediate Similarity	NPD6650	Approved
0.7091	Intermediate Similarity	NPD8130	Phase 1
0.7091	Intermediate Similarity	NPD6847	Approved
0.7091	Intermediate Similarity	NPD6869	Approved
0.7091	Intermediate Similarity	NPD6649	Approved
0.7091	Intermediate Similarity	NPD6617	Approved
0.7083	Intermediate Similarity	NPD3666	Approved
0.7083	Intermediate Similarity	NPD3665	Phase 1
0.7083	Intermediate Similarity	NPD3133	Approved
0.7075	Intermediate Similarity	NPD5175	Approved
0.7075	Intermediate Similarity	NPD5174	Approved
0.7071	Intermediate Similarity	NPD6051	Approved
0.7071	Intermediate Similarity	NPD5328	Approved
0.7065	Intermediate Similarity	NPD5776	Phase 2
0.7065	Intermediate Similarity	NPD6925	Approved
0.7064	Intermediate Similarity	NPD6012	Approved
0.7064	Intermediate Similarity	NPD6014	Approved
0.7064	Intermediate Similarity	NPD6013	Approved
0.7059	Intermediate Similarity	NPD6033	Approved
0.7053	Intermediate Similarity	NPD3667	Approved
0.7048	Intermediate Similarity	NPD4159	Approved
0.7048	Intermediate Similarity	NPD5223	Approved
0.7045	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7507	Approved
0.703	Intermediate Similarity	NPD8171	Discontinued
0.7027	Intermediate Similarity	NPD6882	Approved
0.7021	Intermediate Similarity	NPD7514	Phase 3
0.7021	Intermediate Similarity	NPD6928	Phase 2
0.7021	Intermediate Similarity	NPD7509	Discontinued
0.701	Intermediate Similarity	NPD6893	Approved
0.7009	Intermediate Similarity	NPD5141	Approved
0.7009	Intermediate Similarity	NPD6067	Discontinued
0.6989	Remote Similarity	NPD7145	Approved
0.6972	Remote Similarity	NPD6011	Approved
0.6944	Remote Similarity	NPD4767	Approved
0.6944	Remote Similarity	NPD4768	Approved
0.6939	Remote Similarity	NPD3618	Phase 1
0.6937	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6079	Approved
0.693	Remote Similarity	NPD6009	Approved
0.6916	Remote Similarity	NPD4754	Approved
0.6893	Remote Similarity	NPD5210	Approved
0.6893	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5695	Phase 3
0.6893	Remote Similarity	NPD4629	Approved
0.6889	Remote Similarity	NPD7150	Approved
0.6889	Remote Similarity	NPD7152	Approved
0.6889	Remote Similarity	NPD7151	Approved
0.6875	Remote Similarity	NPD4223	Phase 3
0.6875	Remote Similarity	NPD4221	Approved
0.6864	Remote Similarity	NPD7604	Phase 2
0.686	Remote Similarity	NPD7319	Approved
0.6857	Remote Similarity	NPD5696	Approved
0.6854	Remote Similarity	NPD6922	Approved
0.6854	Remote Similarity	NPD6923	Approved
0.6842	Remote Similarity	NPD7332	Phase 2
0.6838	Remote Similarity	NPD5983	Phase 2
0.6837	Remote Similarity	NPD5329	Approved
0.6818	Remote Similarity	NPD4730	Approved
0.6818	Remote Similarity	NPD5128	Approved
0.6818	Remote Similarity	NPD4729	Approved
0.68	Remote Similarity	NPD6903	Approved
0.6783	Remote Similarity	NPD7115	Discovery
0.6778	Remote Similarity	NPD7143	Approved
0.6778	Remote Similarity	NPD7144	Approved
0.6771	Remote Similarity	NPD6898	Phase 1
0.6771	Remote Similarity	NPD6902	Approved
0.6768	Remote Similarity	NPD6684	Approved
0.6768	Remote Similarity	NPD7334	Approved
0.6768	Remote Similarity	NPD7146	Approved
0.6768	Remote Similarity	NPD6409	Approved
0.6768	Remote Similarity	NPD5330	Approved
0.6768	Remote Similarity	NPD7521	Approved
0.675	Remote Similarity	NPD6336	Discontinued
0.6735	Remote Similarity	NPD4197	Approved
0.6698	Remote Similarity	NPD4225	Approved
0.6696	Remote Similarity	NPD5248	Approved
0.6696	Remote Similarity	NPD5249	Phase 3
0.6696	Remote Similarity	NPD5247	Approved
0.6696	Remote Similarity	NPD5250	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6696	Remote Similarity	NPD5251	Approved
0.6694	Remote Similarity	NPD8449	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4522	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.664	Remote Similarity	NPD8450	Suspended
0.6637	Remote Similarity	NPD5216	Approved
0.6637	Remote Similarity	NPD5217	Approved
0.6637	Remote Similarity	NPD5215	Approved
0.6634	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4788	Approved
0.6607	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5173	Approved
0.6602	Remote Similarity	NPD8035	Phase 2
0.6602	Remote Similarity	NPD8034	Phase 2
0.6602	Remote Similarity	NPD7637	Suspended
0.66	Remote Similarity	NPD4689	Approved
0.66	Remote Similarity	NPD4693	Phase 3
0.66	Remote Similarity	NPD5205	Approved
0.66	Remote Similarity	NPD6098	Approved
0.66	Remote Similarity	NPD4688	Approved
0.66	Remote Similarity	NPD4138	Approved
0.66	Remote Similarity	NPD4690	Approved
0.6593	Remote Similarity	NPD4787	Phase 1
0.6581	Remote Similarity	NPD6335	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