NPASS Compound

Structure

NPC472640 OpenBabel07101718332D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0132 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 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 2 9 1 0 0 0 0 3 10 1 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 7 17 1 0 0 0 0 8 1 1 1 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 10 22 1 0 0 0 0 11 16 1 6 0 0 0 12 17 1 0 0 0 0 13 22 1 1 0 0 0 14 16 1 1 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 4 1 6 0 0 0 17 21 1 6 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.16
Volume:	321.751
LogP:	2.043
LogD:	2.321
LogS:	-2.739
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	4.821
Fsp3:	0.765
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:	-5.06
MDCK Permeability:	6.0600199503824115e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.611
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.779

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.393
Plasma Protein Binding (PPB):	46.90361785888672%
Volume Distribution (VD):	0.779
Pgp-substrate:	31.444772720336914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.462
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	5.158
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.339
AMES Toxicity:	0.383
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.28
Skin Sensitization:	0.147
Carcinogencity:	0.136
Eye Corrosion:	0.005
Eye Irritation:	0.042
Respiratory Toxicity:	0.265

Download Data

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

Natural Product: NPC472640

Natural Product ID:	NPC472640
*Common Name:**	GIBGTMIKVMTTHM-BYTXZFODSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GIBGTMIKVMTTHM-BYTXZFODSA-N
Standard InCHI:	InChI=1S/C17H24O6/c1-8-11-5-12-9(2)15(20)23-17(12,21)7-16(11,4)14(19)6-13(8)22-10(3)18/h8,11,13-14,19,21H,5-7H2,1-4H3/t8-,11-,13+,14-,16+,17-/m1/s1
SMILES:	C[C@@H]1[C@H]2CC3=C(C)C(=O)O[C@@]3(C[C@]2(C)[C@@H](C[C@@H]1OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581364
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23337296]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24484201]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25739048]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933899]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28960981]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1371	Teucrium viscidum	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	7

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[547527]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[547527]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[547527]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[547528]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[547527]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[547527]

☑ 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 NPC472640 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	211
0.1-0.2	1463
0.2-0.3	4574
0.3-0.4	8340
0.4-0.5	13469
0.5-0.6	7124
0.6-0.7	6020
0.7-0.8	1331
0.8-0.85	118
0.85-0.9	37
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472641
0.9767	High Similarity	NPC472642
0.9551	High Similarity	NPC471915
0.9432	High Similarity	NPC78594
0.9231	High Similarity	NPC165632
0.9149	High Similarity	NPC471914
0.914	High Similarity	NPC16601
0.9121	High Similarity	NPC111273
0.9111	High Similarity	NPC110022
0.9053	High Similarity	NPC471938
0.8966	High Similarity	NPC253604
0.8958	High Similarity	NPC471937
0.8851	High Similarity	NPC32223
0.8737	High Similarity	NPC324841
0.871	High Similarity	NPC276110
0.8696	High Similarity	NPC472812
0.8667	High Similarity	NPC242448
0.866	High Similarity	NPC474822
0.8652	High Similarity	NPC131813
0.8632	High Similarity	NPC325229
0.8632	High Similarity	NPC275086
0.8617	High Similarity	NPC234993
0.8617	High Similarity	NPC134072
0.8602	High Similarity	NPC105490
0.8587	High Similarity	NPC472811
0.8586	High Similarity	NPC471205
0.8557	High Similarity	NPC121423
0.8557	High Similarity	NPC475038
0.8557	High Similarity	NPC109195
0.8542	High Similarity	NPC38855
0.8526	High Similarity	NPC51499
0.85	High Similarity	NPC38948
0.85	High Similarity	NPC181994
0.85	High Similarity	NPC325054
0.8495	Intermediate Similarity	NPC7349
0.8478	Intermediate Similarity	NPC78973
0.8469	Intermediate Similarity	NPC471208
0.8469	Intermediate Similarity	NPC45897
0.8469	Intermediate Similarity	NPC120009
0.8462	Intermediate Similarity	NPC472810
0.8462	Intermediate Similarity	NPC472809
0.8438	Intermediate Similarity	NPC278673
0.8416	Intermediate Similarity	NPC206618
0.8416	Intermediate Similarity	NPC31522
0.8404	Intermediate Similarity	NPC57117
0.84	Intermediate Similarity	NPC122816
0.84	Intermediate Similarity	NPC475074
0.8387	Intermediate Similarity	NPC329842
0.8367	Intermediate Similarity	NPC476081
0.8367	Intermediate Similarity	NPC165250
0.8367	Intermediate Similarity	NPC472815
0.8367	Intermediate Similarity	NPC295791
0.8367	Intermediate Similarity	NPC58329
0.8351	Intermediate Similarity	NPC476767
0.8317	Intermediate Similarity	NPC90946
0.8317	Intermediate Similarity	NPC300614
0.8316	Intermediate Similarity	NPC472441
0.8315	Intermediate Similarity	NPC311070
0.83	Intermediate Similarity	NPC218158
0.83	Intermediate Similarity	NPC51719
0.8298	Intermediate Similarity	NPC139692
0.8298	Intermediate Similarity	NPC162615
0.8298	Intermediate Similarity	NPC152778
0.8298	Intermediate Similarity	NPC53555
0.8298	Intermediate Similarity	NPC205034
0.8283	Intermediate Similarity	NPC281378
0.8283	Intermediate Similarity	NPC159533
0.8265	Intermediate Similarity	NPC198992
0.8265	Intermediate Similarity	NPC11974
0.8247	Intermediate Similarity	NPC474440
0.8229	Intermediate Similarity	NPC319861
0.8229	Intermediate Similarity	NPC202833
0.8229	Intermediate Similarity	NPC242848
0.8222	Intermediate Similarity	NPC102048
0.8218	Intermediate Similarity	NPC67321
0.8218	Intermediate Similarity	NPC187435
0.8211	Intermediate Similarity	NPC474554
0.8211	Intermediate Similarity	NPC470255
0.82	Intermediate Similarity	NPC161775
0.8191	Intermediate Similarity	NPC72845
0.8191	Intermediate Similarity	NPC124374
0.8182	Intermediate Similarity	NPC10636
0.8182	Intermediate Similarity	NPC472552
0.8172	Intermediate Similarity	NPC470734
0.8163	Intermediate Similarity	NPC477721
0.8163	Intermediate Similarity	NPC477716
0.8163	Intermediate Similarity	NPC251680
0.8163	Intermediate Similarity	NPC47024
0.8155	Intermediate Similarity	NPC177047
0.8152	Intermediate Similarity	NPC471779
0.8144	Intermediate Similarity	NPC477718
0.8144	Intermediate Similarity	NPC287668
0.8144	Intermediate Similarity	NPC477719
0.8144	Intermediate Similarity	NPC199099
0.8119	Intermediate Similarity	NPC34768
0.8105	Intermediate Similarity	NPC99653
0.81	Intermediate Similarity	NPC97487
0.81	Intermediate Similarity	NPC165608
0.81	Intermediate Similarity	NPC189588
0.81	Intermediate Similarity	NPC10232
0.81	Intermediate Similarity	NPC187302
0.81	Intermediate Similarity	NPC196471
0.81	Intermediate Similarity	NPC120321
0.8085	Intermediate Similarity	NPC220216
0.8085	Intermediate Similarity	NPC310479
0.8085	Intermediate Similarity	NPC209816
0.8085	Intermediate Similarity	NPC280149
0.8085	Intermediate Similarity	NPC182136
0.8085	Intermediate Similarity	NPC221111
0.8081	Intermediate Similarity	NPC471412
0.8081	Intermediate Similarity	NPC472554
0.8081	Intermediate Similarity	NPC477717
0.8065	Intermediate Similarity	NPC291665
0.8061	Intermediate Similarity	NPC473154
0.8058	Intermediate Similarity	NPC322912
0.8058	Intermediate Similarity	NPC475030
0.8058	Intermediate Similarity	NPC299590
0.8041	Intermediate Similarity	NPC473153
0.8041	Intermediate Similarity	NPC16967
0.8041	Intermediate Similarity	NPC475380
0.8041	Intermediate Similarity	NPC209297
0.8041	Intermediate Similarity	NPC221801
0.8041	Intermediate Similarity	NPC211810
0.8041	Intermediate Similarity	NPC17578
0.8041	Intermediate Similarity	NPC284194
0.8041	Intermediate Similarity	NPC240673
0.8041	Intermediate Similarity	NPC471765
0.8021	Intermediate Similarity	NPC191521
0.8021	Intermediate Similarity	NPC182826
0.8021	Intermediate Similarity	NPC161998
0.8021	Intermediate Similarity	NPC105375
0.8021	Intermediate Similarity	NPC474555
0.8021	Intermediate Similarity	NPC140277
0.8021	Intermediate Similarity	NPC469697
0.8	Intermediate Similarity	NPC162973
0.8	Intermediate Similarity	NPC41239
0.8	Intermediate Similarity	NPC238397
0.8	Intermediate Similarity	NPC42658
0.8	Intermediate Similarity	NPC471363
0.8	Intermediate Similarity	NPC249034
0.8	Intermediate Similarity	NPC473675
0.7981	Intermediate Similarity	NPC472666
0.798	Intermediate Similarity	NPC477972
0.798	Intermediate Similarity	NPC20113
0.798	Intermediate Similarity	NPC477968
0.798	Intermediate Similarity	NPC471413
0.798	Intermediate Similarity	NPC477971
0.798	Intermediate Similarity	NPC470761
0.798	Intermediate Similarity	NPC228251
0.798	Intermediate Similarity	NPC473219
0.798	Intermediate Similarity	NPC219285
0.798	Intermediate Similarity	NPC161527
0.7979	Intermediate Similarity	NPC474396
0.7979	Intermediate Similarity	NPC261320
0.7979	Intermediate Similarity	NPC50488
0.7979	Intermediate Similarity	NPC314727
0.7961	Intermediate Similarity	NPC476765
0.7961	Intermediate Similarity	NPC470024
0.7961	Intermediate Similarity	NPC50124
0.7961	Intermediate Similarity	NPC306265
0.7959	Intermediate Similarity	NPC473244
0.7959	Intermediate Similarity	NPC100912
0.7959	Intermediate Similarity	NPC151681
0.7959	Intermediate Similarity	NPC311241
0.7959	Intermediate Similarity	NPC121402
0.7959	Intermediate Similarity	NPC205143
0.7959	Intermediate Similarity	NPC475446
0.7959	Intermediate Similarity	NPC224356
0.7959	Intermediate Similarity	NPC254121
0.7959	Intermediate Similarity	NPC175351
0.7959	Intermediate Similarity	NPC132753
0.7959	Intermediate Similarity	NPC475709
0.7957	Intermediate Similarity	NPC166857
0.7957	Intermediate Similarity	NPC473891
0.7957	Intermediate Similarity	NPC471796
0.7944	Intermediate Similarity	NPC471816
0.7941	Intermediate Similarity	NPC471206
0.7941	Intermediate Similarity	NPC85670
0.7941	Intermediate Similarity	NPC220217
0.7941	Intermediate Similarity	NPC111952
0.7941	Intermediate Similarity	NPC472818
0.7941	Intermediate Similarity	NPC119855
0.7941	Intermediate Similarity	NPC477090
0.7941	Intermediate Similarity	NPC239961
0.7941	Intermediate Similarity	NPC81630
0.7941	Intermediate Similarity	NPC82251
0.7938	Intermediate Similarity	NPC329435
0.7938	Intermediate Similarity	NPC157686
0.7938	Intermediate Similarity	NPC259042
0.7925	Intermediate Similarity	NPC264153
0.7921	Intermediate Similarity	NPC134270
0.7921	Intermediate Similarity	NPC7613
0.7921	Intermediate Similarity	NPC475889
0.7921	Intermediate Similarity	NPC7644
0.7921	Intermediate Similarity	NPC23584
0.7921	Intermediate Similarity	NPC127933
0.7921	Intermediate Similarity	NPC160583
0.7921	Intermediate Similarity	NPC472821
0.7917	Intermediate Similarity	NPC472303
0.7912	Intermediate Similarity	NPC79945

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 NPC472640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1803
0.2-0.3	3834
0.3-0.4	2193
0.4-0.5	707
0.5-0.6	252
0.6-0.7	160
0.7-0.8	23
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
0.8163	Intermediate Similarity	NPD7640	Approved
0.8163	Intermediate Similarity	NPD7639	Approved
0.8061	Intermediate Similarity	NPD7638	Approved
0.8058	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7632	Discontinued
0.7879	Intermediate Similarity	NPD4225	Approved
0.781	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD6686	Approved
0.7636	Intermediate Similarity	NPD7328	Approved
0.7636	Intermediate Similarity	NPD7327	Approved
0.7568	Intermediate Similarity	NPD7516	Approved
0.7524	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8335	Approved
0.7434	Intermediate Similarity	NPD8378	Approved
0.7434	Intermediate Similarity	NPD8379	Approved
0.7434	Intermediate Similarity	NPD8296	Approved
0.7434	Intermediate Similarity	NPD8380	Approved
0.7379	Intermediate Similarity	NPD5344	Discontinued
0.7345	Intermediate Similarity	NPD8377	Approved
0.7345	Intermediate Similarity	NPD8294	Approved
0.7281	Intermediate Similarity	NPD8033	Approved
0.7263	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD7319	Approved
0.7115	Intermediate Similarity	NPD6648	Approved
0.71	Intermediate Similarity	NPD7637	Suspended
0.6983	Remote Similarity	NPD7503	Approved
0.6909	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6695	Phase 3
0.6796	Remote Similarity	NPD7748	Approved
0.6789	Remote Similarity	NPD5739	Approved
0.6789	Remote Similarity	NPD6675	Approved
0.6789	Remote Similarity	NPD7128	Approved
0.6789	Remote Similarity	NPD6402	Approved
0.6783	Remote Similarity	NPD7115	Discovery
0.6765	Remote Similarity	NPD7515	Phase 2
0.6762	Remote Similarity	NPD7902	Approved
0.6727	Remote Similarity	NPD5701	Approved
0.6727	Remote Similarity	NPD6412	Phase 2
0.6727	Remote Similarity	NPD5697	Approved
0.6726	Remote Similarity	NPD6882	Approved
0.6698	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6638	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD6014	Approved
0.6607	Remote Similarity	NPD6372	Approved
0.6607	Remote Similarity	NPD6013	Approved
0.6607	Remote Similarity	NPD6373	Approved
0.6607	Remote Similarity	NPD6012	Approved
0.66	Remote Similarity	NPD3618	Phase 1
0.6562	Remote Similarity	NPD6929	Approved
0.6549	Remote Similarity	NPD7102	Approved
0.6549	Remote Similarity	NPD6883	Approved
0.6549	Remote Similarity	NPD7290	Approved
0.6538	Remote Similarity	NPD6399	Phase 3
0.6538	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD5779	Approved
0.6535	Remote Similarity	NPD7524	Approved
0.6535	Remote Similarity	NPD7750	Discontinued
0.6529	Remote Similarity	NPD7492	Approved
0.6522	Remote Similarity	NPD4632	Approved
0.6518	Remote Similarity	NPD6011	Approved
0.6514	Remote Similarity	NPD5211	Phase 2
0.6496	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7525	Registered
0.6495	Remote Similarity	NPD6930	Phase 2
0.6495	Remote Similarity	NPD6931	Approved
0.6491	Remote Similarity	NPD8130	Phase 1
0.6491	Remote Similarity	NPD6617	Approved
0.6491	Remote Similarity	NPD6649	Approved
0.6491	Remote Similarity	NPD6847	Approved
0.6491	Remote Similarity	NPD6869	Approved
0.6491	Remote Similarity	NPD6650	Approved
0.6486	Remote Similarity	NPD6008	Approved
0.6476	Remote Similarity	NPD7900	Approved
0.6476	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6616	Approved
0.6471	Remote Similarity	NPD6059	Approved
0.6471	Remote Similarity	NPD6319	Approved
0.6471	Remote Similarity	NPD6054	Approved
0.6449	Remote Similarity	NPD6084	Phase 2
0.6449	Remote Similarity	NPD4755	Approved
0.6449	Remote Similarity	NPD6083	Phase 2
0.6446	Remote Similarity	NPD8328	Phase 3
0.6442	Remote Similarity	NPD8035	Phase 2
0.6442	Remote Similarity	NPD8034	Phase 2
0.6435	Remote Similarity	NPD8297	Approved
0.6435	Remote Similarity	NPD6053	Discontinued
0.6423	Remote Similarity	NPD8293	Discontinued
0.6423	Remote Similarity	NPD7078	Approved
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD6015	Approved
0.6408	Remote Similarity	NPD5328	Approved
0.6408	Remote Similarity	NPD6051	Approved
0.6404	Remote Similarity	NPD6371	Approved
0.6396	Remote Similarity	NPD5141	Approved
0.6392	Remote Similarity	NPD7645	Phase 2
0.6381	Remote Similarity	NPD4202	Approved
0.6371	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6354	Remote Similarity	NPD5776	Phase 2
0.6354	Remote Similarity	NPD6925	Approved
0.6348	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5286	Approved
0.633	Remote Similarity	NPD5285	Approved
0.633	Remote Similarity	NPD4700	Approved
0.633	Remote Similarity	NPD4696	Approved
0.6327	Remote Similarity	NPD7332	Phase 2
0.6327	Remote Similarity	NPD7514	Phase 3
0.6289	Remote Similarity	NPD6118	Approved
0.6289	Remote Similarity	NPD7145	Approved
0.6289	Remote Similarity	NPD6114	Approved
0.6289	Remote Similarity	NPD6115	Approved
0.6289	Remote Similarity	NPD6697	Approved
0.6286	Remote Similarity	NPD6079	Approved
0.6286	Remote Similarity	NPD7087	Discontinued
0.6281	Remote Similarity	NPD5983	Phase 2
0.6275	Remote Similarity	NPD6409	Approved
0.6275	Remote Similarity	NPD5330	Approved
0.6275	Remote Similarity	NPD7521	Approved
0.6275	Remote Similarity	NPD4249	Approved
0.6275	Remote Similarity	NPD7146	Approved
0.6275	Remote Similarity	NPD6684	Approved
0.6275	Remote Similarity	NPD7334	Approved
0.6273	Remote Similarity	NPD4159	Approved
0.6271	Remote Similarity	NPD6274	Approved
0.6263	Remote Similarity	NPD6902	Approved
0.6262	Remote Similarity	NPD5695	Phase 3
0.6262	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5696	Approved
0.6238	Remote Similarity	NPD3666	Approved
0.6238	Remote Similarity	NPD3133	Approved
0.6238	Remote Similarity	NPD3665	Phase 1
0.6216	Remote Similarity	NPD5225	Approved
0.6216	Remote Similarity	NPD5224	Approved
0.6216	Remote Similarity	NPD5226	Approved
0.6216	Remote Similarity	NPD4633	Approved
0.6214	Remote Similarity	NPD4251	Approved
0.6214	Remote Similarity	NPD4250	Approved
0.6214	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4697	Phase 3
0.6204	Remote Similarity	NPD5221	Approved
0.6204	Remote Similarity	NPD5222	Approved
0.6204	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3667	Approved
0.619	Remote Similarity	NPD3168	Discontinued
0.619	Remote Similarity	NPD5785	Approved
0.6186	Remote Similarity	NPD6116	Phase 1
0.6179	Remote Similarity	NPD7604	Phase 2
0.6179	Remote Similarity	NPD6067	Discontinued
0.6176	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6893	Approved
0.6162	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5175	Approved
0.6161	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD6672	Approved
0.6148	Remote Similarity	NPD8515	Approved
0.6148	Remote Similarity	NPD8513	Phase 3
0.6148	Remote Similarity	NPD8517	Approved
0.6148	Remote Similarity	NPD8516	Approved
0.6147	Remote Similarity	NPD5173	Approved
0.6132	Remote Similarity	NPD6411	Approved
0.6132	Remote Similarity	NPD5693	Phase 1
0.6126	Remote Similarity	NPD5223	Approved
0.6121	Remote Similarity	NPD4634	Approved
0.6116	Remote Similarity	NPD7100	Approved
0.6116	Remote Similarity	NPD7101	Approved
0.61	Remote Similarity	NPD6898	Phase 1
0.6095	Remote Similarity	NPD4753	Phase 2
0.6083	Remote Similarity	NPD6317	Approved
0.6082	Remote Similarity	NPD6117	Approved
0.6082	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6336	Discontinued
0.6078	Remote Similarity	NPD4786	Approved
0.6064	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3573	Approved
0.6053	Remote Similarity	NPD4768	Approved
0.6053	Remote Similarity	NPD4767	Approved
0.6033	Remote Similarity	NPD6314	Approved
0.6033	Remote Similarity	NPD6313	Approved
0.6033	Remote Similarity	NPD6335	Approved
0.602	Remote Similarity	NPD6932	Approved
0.6019	Remote Similarity	NPD5282	Discontinued
0.6018	Remote Similarity	NPD4754	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