NPASS Compound

Structure

NPC471242 OpenBabel07101718322D 26 30 0 0 1 0 0 0 0 0999 V2000 2.7048 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1236 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5123 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8102 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3118 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8247 -0.3600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3369 -0.9960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1668 0.3930 0.0000 C 0 0 2 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 -0.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4896 -2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5838 -1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3893 1.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1236 1.2261 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 9 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 5 1 0 0 0 0 5 11 2 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 17 1 0 0 0 0 8 26 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 4 1 1 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 1 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 1 0 0 0 14 19 1 1 0 0 0 14 22 1 0 0 0 0 15 19 1 6 0 0 0 15 23 1 0 0 0 0 16 20 1 6 0 0 0 16 24 1 0 0 0 0 18 8 1 1 0 0 0 19 20 1 6 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.19
Volume:	359.162
LogP:	1.541
LogD:	0.532
LogS:	-3.509
# Rotatable Bonds:	0
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	7.205
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.318
MDCK Permeability:	1.0755332368717063e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.827
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.296

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	60.87363815307617%
Volume Distribution (VD):	0.777
Pgp-substrate:	53.28907775878906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.207
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.645
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	2.005
Half-life (T1/2):	0.628

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.543
Carcinogencity:	0.492
Eye Corrosion:	0.005
Eye Irritation:	0.042
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC471242

Natural Product ID:	NPC471242
*Common Name:**	NKEDCEDIFVIJPA-FQZJVCEQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NKEDCEDIFVIJPA-FQZJVCEQSA-N
Standard InCHI:	InChI=1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h5,10,12-16,21-25H,1,4,6-8H2,2-3H3/t10-,12-,13+,14+,15+,16-,18+,19-,20-/m0/s1
SMILES:	C=C1[C@@H]2CC=C3[C@]([C@@H]1O)([C@@H]2O)[C@@]1(O)OC[C@@]23[C@@H](O)CCC([C@H]2[C@@H]1O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2407381
PubChem CID:	71745897
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[23819871]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17800	Isodon rosthornii	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[528881]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000.0	nM	PMID[528881]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[528881]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[528881]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[528881]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[528881]

☑ 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 NPC471242 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	238
0.1-0.2	1785
0.2-0.3	5458
0.3-0.4	12486
0.4-0.5	10303
0.5-0.6	5571
0.6-0.7	4020
0.7-0.8	2376
0.8-0.85	380
0.85-0.9	72
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC152966
0.9355	High Similarity	NPC473348
0.9149	High Similarity	NPC30477
0.914	High Similarity	NPC296620
0.8878	High Similarity	NPC144486
0.8878	High Similarity	NPC470168
0.88	High Similarity	NPC474464
0.8776	High Similarity	NPC471247
0.875	High Similarity	NPC476894
0.8713	High Similarity	NPC474015
0.8713	High Similarity	NPC242748
0.87	High Similarity	NPC475701
0.8673	High Similarity	NPC469725
0.8673	High Similarity	NPC476895
0.8641	High Similarity	NPC128133
0.8614	High Similarity	NPC75608
0.86	High Similarity	NPC31085
0.8598	High Similarity	NPC470171
0.8586	High Similarity	NPC91497
0.8586	High Similarity	NPC64348
0.8571	High Similarity	NPC476893
0.8529	High Similarity	NPC473923
0.8529	High Similarity	NPC473476
0.8515	High Similarity	NPC471467
0.8515	High Similarity	NPC473198
0.85	High Similarity	NPC474022
0.85	High Similarity	NPC476896
0.85	High Similarity	NPC470434
0.8491	Intermediate Similarity	NPC307642
0.8485	Intermediate Similarity	NPC275865
0.8447	Intermediate Similarity	NPC473469
0.8447	Intermediate Similarity	NPC470166
0.8431	Intermediate Similarity	NPC471111
0.8431	Intermediate Similarity	NPC470885
0.8431	Intermediate Similarity	NPC221562
0.8431	Intermediate Similarity	NPC187400
0.8416	Intermediate Similarity	NPC177701
0.8416	Intermediate Similarity	NPC22634
0.84	Intermediate Similarity	NPC473790
0.84	Intermediate Similarity	NPC469942
0.8396	Intermediate Similarity	NPC477050
0.8396	Intermediate Similarity	NPC19888
0.8384	Intermediate Similarity	NPC475032
0.8384	Intermediate Similarity	NPC475033
0.8384	Intermediate Similarity	NPC76486
0.8384	Intermediate Similarity	NPC177818
0.8384	Intermediate Similarity	NPC243728
0.8384	Intermediate Similarity	NPC473890
0.8381	Intermediate Similarity	NPC141433
0.8365	Intermediate Similarity	NPC476541
0.8365	Intermediate Similarity	NPC476538
0.8365	Intermediate Similarity	NPC476540
0.8365	Intermediate Similarity	NPC476539
0.8365	Intermediate Similarity	NPC7213
0.835	Intermediate Similarity	NPC472898
0.835	Intermediate Similarity	NPC472900
0.835	Intermediate Similarity	NPC474569
0.835	Intermediate Similarity	NPC181845
0.835	Intermediate Similarity	NPC472899
0.8333	Intermediate Similarity	NPC16573
0.8318	Intermediate Similarity	NPC51154
0.8317	Intermediate Similarity	NPC176406
0.8317	Intermediate Similarity	NPC155974
0.8302	Intermediate Similarity	NPC114188
0.8302	Intermediate Similarity	NPC13190
0.8302	Intermediate Similarity	NPC197231
0.8302	Intermediate Similarity	NPC476547
0.83	Intermediate Similarity	NPC234287
0.83	Intermediate Similarity	NPC158088
0.83	Intermediate Similarity	NPC280825
0.8286	Intermediate Similarity	NPC477027
0.8286	Intermediate Similarity	NPC306131
0.8286	Intermediate Similarity	NPC475670
0.8286	Intermediate Similarity	NPC70204
0.8286	Intermediate Similarity	NPC477026
0.8283	Intermediate Similarity	NPC207617
0.8269	Intermediate Similarity	NPC470432
0.8269	Intermediate Similarity	NPC14704
0.8269	Intermediate Similarity	NPC283829
0.8269	Intermediate Similarity	NPC113044
0.8269	Intermediate Similarity	NPC161676
0.8269	Intermediate Similarity	NPC190395
0.8269	Intermediate Similarity	NPC305423
0.8269	Intermediate Similarity	NPC470169
0.8269	Intermediate Similarity	NPC231340
0.8269	Intermediate Similarity	NPC226642
0.8269	Intermediate Similarity	NPC94272
0.8269	Intermediate Similarity	NPC470170
0.8269	Intermediate Similarity	NPC230507
0.8265	Intermediate Similarity	NPC305160
0.8265	Intermediate Similarity	NPC477927
0.8265	Intermediate Similarity	NPC72817
0.8257	Intermediate Similarity	NPC218970
0.8252	Intermediate Similarity	NPC273879
0.8252	Intermediate Similarity	NPC93352
0.8252	Intermediate Similarity	NPC470768
0.8252	Intermediate Similarity	NPC165033
0.8252	Intermediate Similarity	NPC312774
0.8241	Intermediate Similarity	NPC477810
0.8235	Intermediate Similarity	NPC159036
0.8235	Intermediate Similarity	NPC272015
0.8235	Intermediate Similarity	NPC136816
0.8235	Intermediate Similarity	NPC312553
0.8235	Intermediate Similarity	NPC288694
0.8229	Intermediate Similarity	NPC105495
0.8224	Intermediate Similarity	NPC210569
0.8224	Intermediate Similarity	NPC244431
0.8224	Intermediate Similarity	NPC32361
0.8224	Intermediate Similarity	NPC263359
0.8224	Intermediate Similarity	NPC473567
0.8224	Intermediate Similarity	NPC216595
0.8224	Intermediate Similarity	NPC31896
0.8224	Intermediate Similarity	NPC112274
0.8218	Intermediate Similarity	NPC7341
0.8218	Intermediate Similarity	NPC282669
0.8218	Intermediate Similarity	NPC208358
0.8218	Intermediate Similarity	NPC473200
0.82	Intermediate Similarity	NPC240372
0.819	Intermediate Similarity	NPC472897
0.819	Intermediate Similarity	NPC295980
0.819	Intermediate Similarity	NPC98696
0.819	Intermediate Similarity	NPC472896
0.8173	Intermediate Similarity	NPC470767
0.8173	Intermediate Similarity	NPC470763
0.8173	Intermediate Similarity	NPC309448
0.8173	Intermediate Similarity	NPC26798
0.8163	Intermediate Similarity	NPC242419
0.8163	Intermediate Similarity	NPC235126
0.8155	Intermediate Similarity	NPC245280
0.8155	Intermediate Similarity	NPC155010
0.8155	Intermediate Similarity	NPC131479
0.8155	Intermediate Similarity	NPC114874
0.8155	Intermediate Similarity	NPC211879
0.8155	Intermediate Similarity	NPC120123
0.8155	Intermediate Similarity	NPC162354
0.8155	Intermediate Similarity	NPC8039
0.8155	Intermediate Similarity	NPC189852
0.8155	Intermediate Similarity	NPC472252
0.8155	Intermediate Similarity	NPC473020
0.8155	Intermediate Similarity	NPC286969
0.8155	Intermediate Similarity	NPC31907
0.8155	Intermediate Similarity	NPC16520
0.8155	Intermediate Similarity	NPC157659
0.8148	Intermediate Similarity	NPC476546
0.8148	Intermediate Similarity	NPC79900
0.8148	Intermediate Similarity	NPC144068
0.8137	Intermediate Similarity	NPC475617
0.8137	Intermediate Similarity	NPC309425
0.8137	Intermediate Similarity	NPC267510
0.8137	Intermediate Similarity	NPC47566
0.8137	Intermediate Similarity	NPC129372
0.8137	Intermediate Similarity	NPC88000
0.8137	Intermediate Similarity	NPC4831
0.8137	Intermediate Similarity	NPC472023
0.8137	Intermediate Similarity	NPC160734
0.8131	Intermediate Similarity	NPC56025
0.8131	Intermediate Similarity	NPC475247
0.8131	Intermediate Similarity	NPC294129
0.8119	Intermediate Similarity	NPC309493
0.8119	Intermediate Similarity	NPC5358
0.8119	Intermediate Similarity	NPC216260
0.8113	Intermediate Similarity	NPC218571
0.8113	Intermediate Similarity	NPC143706
0.8113	Intermediate Similarity	NPC84956
0.8113	Intermediate Similarity	NPC102016
0.8113	Intermediate Similarity	NPC46190
0.8113	Intermediate Similarity	NPC6806
0.8113	Intermediate Similarity	NPC302057
0.8113	Intermediate Similarity	NPC14630
0.8113	Intermediate Similarity	NPC95051
0.8113	Intermediate Similarity	NPC472534
0.8113	Intermediate Similarity	NPC208383
0.8113	Intermediate Similarity	NPC40440
0.8113	Intermediate Similarity	NPC475550
0.8113	Intermediate Similarity	NPC250089
0.8113	Intermediate Similarity	NPC248746
0.8113	Intermediate Similarity	NPC249265
0.8113	Intermediate Similarity	NPC244086
0.8113	Intermediate Similarity	NPC476835
0.8113	Intermediate Similarity	NPC22779
0.8113	Intermediate Similarity	NPC224098
0.8113	Intermediate Similarity	NPC171073
0.8113	Intermediate Similarity	NPC232054
0.8113	Intermediate Similarity	NPC157530
0.8113	Intermediate Similarity	NPC194207
0.8113	Intermediate Similarity	NPC309278
0.8113	Intermediate Similarity	NPC470433
0.8113	Intermediate Similarity	NPC42482
0.8113	Intermediate Similarity	NPC475333
0.8113	Intermediate Similarity	NPC477809
0.8113	Intermediate Similarity	NPC73243
0.8113	Intermediate Similarity	NPC150372
0.8113	Intermediate Similarity	NPC300557
0.81	Intermediate Similarity	NPC90583
0.8095	Intermediate Similarity	NPC33053
0.8095	Intermediate Similarity	NPC181467
0.8095	Intermediate Similarity	NPC476594
0.8077	Intermediate Similarity	NPC475521
0.8077	Intermediate Similarity	NPC475365
0.8073	Intermediate Similarity	NPC11548

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 NPC471242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1922
0.2-0.3	4179
0.3-0.4	1909
0.4-0.5	518
0.5-0.6	228
0.6-0.7	166
0.7-0.8	26
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7807	Intermediate Similarity	NPD8033	Approved
0.7632	Intermediate Similarity	NPD7516	Approved
0.7593	Intermediate Similarity	NPD6412	Phase 2
0.7565	Intermediate Similarity	NPD8377	Approved
0.7565	Intermediate Similarity	NPD8294	Approved
0.7544	Intermediate Similarity	NPD7327	Approved
0.7544	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7475	Intermediate Similarity	NPD7524	Approved
0.735	Intermediate Similarity	NPD7503	Approved
0.73	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7525	Registered
0.7107	Intermediate Similarity	NPD7507	Approved
0.7071	Intermediate Similarity	NPD6695	Phase 3
0.7043	Intermediate Similarity	NPD8133	Approved
0.7037	Intermediate Similarity	NPD7640	Approved
0.7037	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD7645	Phase 2
0.6991	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6059	Approved
0.6975	Remote Similarity	NPD6054	Approved
0.6952	Remote Similarity	NPD8171	Discontinued
0.6947	Remote Similarity	NPD6942	Approved
0.6947	Remote Similarity	NPD7339	Approved
0.6944	Remote Similarity	NPD7638	Approved
0.6935	Remote Similarity	NPD7319	Approved
0.6917	Remote Similarity	NPD6015	Approved
0.6917	Remote Similarity	NPD6016	Approved
0.6897	Remote Similarity	NPD4632	Approved
0.6864	Remote Similarity	NPD6009	Approved
0.686	Remote Similarity	NPD6370	Approved
0.686	Remote Similarity	NPD5988	Approved
0.6837	Remote Similarity	NPD6929	Approved
0.6833	Remote Similarity	NPD6319	Approved
0.6818	Remote Similarity	NPD4159	Approved
0.6796	Remote Similarity	NPD7750	Discontinued
0.6789	Remote Similarity	NPD4225	Approved
0.6772	Remote Similarity	NPD8449	Approved
0.6768	Remote Similarity	NPD4748	Discontinued
0.6768	Remote Similarity	NPD6931	Approved
0.6768	Remote Similarity	NPD6930	Phase 2
0.6768	Remote Similarity	NPD6928	Phase 2
0.6762	Remote Similarity	NPD3168	Discontinued
0.6757	Remote Similarity	NPD5211	Phase 2
0.6754	Remote Similarity	NPD6686	Approved
0.6748	Remote Similarity	NPD7492	Approved
0.6726	Remote Similarity	NPD6402	Approved
0.6726	Remote Similarity	NPD5739	Approved
0.6726	Remote Similarity	NPD7128	Approved
0.6726	Remote Similarity	NPD6675	Approved
0.6723	Remote Similarity	NPD7115	Discovery
0.6723	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7736	Approved
0.6719	Remote Similarity	NPD8450	Suspended
0.6697	Remote Similarity	NPD4755	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD5344	Discontinued
0.664	Remote Similarity	NPD8293	Discontinued
0.664	Remote Similarity	NPD7078	Approved
0.6638	Remote Similarity	NPD4634	Approved
0.6637	Remote Similarity	NPD5141	Approved
0.6636	Remote Similarity	NPD4202	Approved
0.6636	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD5776	Phase 2
0.6633	Remote Similarity	NPD6925	Approved
0.6609	Remote Similarity	NPD7320	Approved
0.6609	Remote Similarity	NPD6899	Approved
0.6609	Remote Similarity	NPD6881	Approved
0.6579	Remote Similarity	NPD6008	Approved
0.6577	Remote Similarity	NPD5286	Approved
0.6577	Remote Similarity	NPD5285	Approved
0.6577	Remote Similarity	NPD4700	Approved
0.6577	Remote Similarity	NPD4696	Approved
0.6566	Remote Similarity	NPD7145	Approved
0.6552	Remote Similarity	NPD6373	Approved
0.6552	Remote Similarity	NPD6012	Approved
0.6552	Remote Similarity	NPD6013	Approved
0.6552	Remote Similarity	NPD6014	Approved
0.6552	Remote Similarity	NPD6372	Approved
0.6542	Remote Similarity	NPD7087	Discontinued
0.6532	Remote Similarity	NPD6067	Discontinued
0.6531	Remote Similarity	NPD6933	Approved
0.6505	Remote Similarity	NPD4786	Approved
0.6504	Remote Similarity	NPD8513	Phase 3
0.6504	Remote Similarity	NPD8516	Approved
0.6504	Remote Similarity	NPD5983	Phase 2
0.6504	Remote Similarity	NPD8515	Approved
0.6504	Remote Similarity	NPD8517	Approved
0.6496	Remote Similarity	NPD7102	Approved
0.6496	Remote Similarity	NPD7290	Approved
0.6496	Remote Similarity	NPD6883	Approved
0.6495	Remote Similarity	NPD4785	Approved
0.6495	Remote Similarity	NPD4784	Approved
0.6471	Remote Similarity	NPD3667	Approved
0.6466	Remote Similarity	NPD6011	Approved
0.646	Remote Similarity	NPD7632	Discontinued
0.646	Remote Similarity	NPD5226	Approved
0.646	Remote Similarity	NPD5225	Approved
0.646	Remote Similarity	NPD4633	Approved
0.646	Remote Similarity	NPD5224	Approved
0.6458	Remote Similarity	NPD4243	Approved
0.6457	Remote Similarity	NPD6033	Approved
0.6442	Remote Similarity	NPD6893	Approved
0.6441	Remote Similarity	NPD6649	Approved
0.6441	Remote Similarity	NPD6869	Approved
0.6441	Remote Similarity	NPD8130	Phase 1
0.6441	Remote Similarity	NPD6617	Approved
0.6441	Remote Similarity	NPD6847	Approved
0.6441	Remote Similarity	NPD6650	Approved
0.6436	Remote Similarity	NPD7514	Phase 3
0.6404	Remote Similarity	NPD5174	Approved
0.6404	Remote Similarity	NPD5175	Approved
0.64	Remote Similarity	NPD7604	Phase 2
0.6396	Remote Similarity	NPD6084	Phase 2
0.6396	Remote Similarity	NPD6083	Phase 2
0.6389	Remote Similarity	NPD7637	Suspended
0.6387	Remote Similarity	NPD6053	Discontinued
0.6381	Remote Similarity	NPD3618	Phase 1
0.6373	Remote Similarity	NPD6902	Approved
0.6372	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6356	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5328	Approved
0.6355	Remote Similarity	NPD4753	Phase 2
0.6355	Remote Similarity	NPD6051	Approved
0.6348	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3666	Approved
0.6346	Remote Similarity	NPD3133	Approved
0.6346	Remote Similarity	NPD3665	Phase 1
0.6327	Remote Similarity	NPD6924	Approved
0.6327	Remote Similarity	NPD6926	Approved
0.6325	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6932	Approved
0.6299	Remote Similarity	NPD6336	Discontinued
0.6293	Remote Similarity	NPD4768	Approved
0.6293	Remote Similarity	NPD4767	Approved
0.6283	Remote Similarity	NPD6648	Approved
0.6275	Remote Similarity	NPD7332	Phase 2
0.6273	Remote Similarity	NPD7748	Approved
0.6263	Remote Similarity	NPD4190	Phase 3
0.6263	Remote Similarity	NPD8264	Approved
0.6263	Remote Similarity	NPD5275	Approved
0.6261	Remote Similarity	NPD4754	Approved
0.6259	Remote Similarity	NPD7625	Phase 1
0.625	Remote Similarity	NPD7902	Approved
0.6239	Remote Similarity	NPD8035	Phase 2
0.6239	Remote Similarity	NPD6079	Approved
0.6239	Remote Similarity	NPD7515	Phase 2
0.6239	Remote Similarity	NPD8034	Phase 2
0.623	Remote Similarity	NPD6274	Approved
0.6226	Remote Similarity	NPD4249	Approved
0.6214	Remote Similarity	NPD6898	Phase 1
0.6195	Remote Similarity	NPD5696	Approved
0.6186	Remote Similarity	NPD4730	Approved
0.6186	Remote Similarity	NPD5128	Approved
0.6186	Remote Similarity	NPD4729	Approved
0.6176	Remote Similarity	NPD4195	Approved
0.6176	Remote Similarity	NPD6683	Phase 2
0.6168	Remote Similarity	NPD4251	Approved
0.6168	Remote Similarity	NPD4250	Approved
0.6162	Remote Similarity	NPD1810	Approved
0.6162	Remote Similarity	NPD1811	Approved
0.6161	Remote Similarity	NPD5221	Approved
0.6161	Remote Similarity	NPD4697	Phase 3
0.6161	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD5357	Phase 1
0.6132	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8074	Phase 3
0.6122	Remote Similarity	NPD7152	Approved
0.6122	Remote Similarity	NPD7151	Approved
0.6122	Remote Similarity	NPD7150	Approved
0.6117	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7509	Discontinued
0.6111	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD5956	Approved
0.6106	Remote Similarity	NPD5173	Approved
0.6102	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6411	Approved
0.6083	Remote Similarity	NPD5250	Approved
0.6083	Remote Similarity	NPD6371	Approved
0.6083	Remote Similarity	NPD5248	Approved
0.6083	Remote Similarity	NPD5251	Approved
0.6083	Remote Similarity	NPD5249	Phase 3
0.6083	Remote Similarity	NPD5247	Approved
0.6082	Remote Similarity	NPD6923	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