NPASS Compound

Structure

CID39683 OpenBabel06191715372D 26 30 0 0 1 0 0 0 0 0999 V2000 3.0115 -2.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9260 -2.1451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6018 -2.7745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 -2.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 -2.3190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8131 -3.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6261 -1.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0675 -0.7987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 -0.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0955 -2.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6261 -2.8164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0001 -2.8164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6018 -0.9528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7518 -1.4081 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7912 -0.0618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8130 -0.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 -1.4082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8130 -1.4082 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8130 -1.4081 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7932 -3.2744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2098 -0.6148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1817 0.6151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6018 -0.0139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6971 0.0334 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 10 2 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 18 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 8 25 1 0 0 0 0 9 19 1 0 0 0 0 9 26 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 6 1 6 0 0 0 12 13 1 0 0 0 0 12 21 1 1 0 0 0 13 19 1 1 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 20 1 6 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 18 2 1 6 0 0 0 19 5 1 1 0 0 0 20 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	356.526
LogP:	1.553
LogD:	1.056
LogS:	-4.061
# Rotatable Bonds:	0
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	6.727
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:	-5.413
MDCK Permeability:	1.3881732229492627e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.617

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797
Plasma Protein Binding (PPB):	43.4171142578125%
Volume Distribution (VD):	1.156
Pgp-substrate:	63.285194396972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.793
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	3.065
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.178
Rat Oral Acute Toxicity:	0.735
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.252
Carcinogencity:	0.622
Eye Corrosion:	0.006
Eye Irritation:	0.339
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC39683

Natural Product ID:	NPC39683
*Common Name:**	Guidongnin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BEOHZDZVHPQJNV-SJOQVHCZSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-10-11-6-12(21)13-19(9-26-17(24)20(13,7-11)15(10)22)5-3-4-18(2)8-25-16(23)14(18)19/h11-15,21-22H,1,3-9H2,2H3/t11-,12-,13+,14-,15-,18+,19-,20+/m1/s1
SMILES:	O[C@@H]1C[C@@H]2C[C@]3([C@@H]1[C@@]1(CCC[C@@]4([C@H]1C(=O)OC4)C)COC3=O)[C@@H](C2=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460333
PubChem CID:	12067312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575445]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20521771]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25590529]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28626	Isodon rubescens	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
NPT111	Cell Line	K562	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[463465]

☑ 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 NPC39683 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	227
0.1-0.2	1645
0.2-0.3	5819
0.3-0.4	11457
0.4-0.5	9471
0.5-0.6	5950
0.6-0.7	6010
0.7-0.8	1831
0.8-0.85	184
0.85-0.9	84
0.9-0.95	18
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC285927
0.9208	High Similarity	NPC98633
0.9208	High Similarity	NPC255655
0.9208	High Similarity	NPC130302
0.91	High Similarity	NPC471246
0.9072	High Similarity	NPC267921
0.902	High Similarity	NPC124053
0.9	High Similarity	NPC37600
0.898	High Similarity	NPC121218
0.898	High Similarity	NPC253886
0.8942	High Similarity	NPC285086
0.8932	High Similarity	NPC471251
0.8922	High Similarity	NPC471250
0.8878	High Similarity	NPC108371
0.8812	High Similarity	NPC295366
0.88	High Similarity	NPC469985
0.8788	High Similarity	NPC295276
0.8776	High Similarity	NPC474793
0.875	High Similarity	NPC56025
0.8725	High Similarity	NPC88833
0.8725	High Similarity	NPC96333
0.8713	High Similarity	NPC47281
0.87	High Similarity	NPC170615
0.8673	High Similarity	NPC253586
0.8667	High Similarity	NPC40608
0.8654	High Similarity	NPC42776
0.8627	High Similarity	NPC103172
0.8627	High Similarity	NPC50535
0.8627	High Similarity	NPC164600
0.8614	High Similarity	NPC140723
0.8614	High Similarity	NPC96217
0.8614	High Similarity	NPC139347
0.8614	High Similarity	NPC266
0.8614	High Similarity	NPC87927
0.86	High Similarity	NPC163963
0.86	High Similarity	NPC289148
0.86	High Similarity	NPC148279
0.86	High Similarity	NPC46848
0.86	High Similarity	NPC52899
0.86	High Similarity	NPC236585
0.86	High Similarity	NPC75941
0.8586	High Similarity	NPC26270
0.8586	High Similarity	NPC471038
0.8544	High Similarity	NPC61071
0.8529	High Similarity	NPC101842
0.8529	High Similarity	NPC202793
0.8529	High Similarity	NPC474558
0.8529	High Similarity	NPC13149
0.8515	High Similarity	NPC124544
0.8515	High Similarity	NPC214946
0.8515	High Similarity	NPC76866
0.8515	High Similarity	NPC246736
0.8515	High Similarity	NPC304832
0.8515	High Similarity	NPC148628
0.8515	High Similarity	NPC286519
0.8515	High Similarity	NPC88203
0.8515	High Similarity	NPC275990
0.85	High Similarity	NPC180733
0.85	High Similarity	NPC37047
0.85	High Similarity	NPC287676
0.85	High Similarity	NPC41971
0.8476	Intermediate Similarity	NPC49730
0.8476	Intermediate Similarity	NPC98069
0.8469	Intermediate Similarity	NPC470232
0.8454	Intermediate Similarity	NPC147272
0.8447	Intermediate Similarity	NPC28791
0.8438	Intermediate Similarity	NPC100313
0.8431	Intermediate Similarity	NPC216114
0.8416	Intermediate Similarity	NPC14634
0.8411	Intermediate Similarity	NPC52634
0.84	Intermediate Similarity	NPC28864
0.84	Intermediate Similarity	NPC20479
0.84	Intermediate Similarity	NPC469986
0.84	Intermediate Similarity	NPC38296
0.84	Intermediate Similarity	NPC98837
0.84	Intermediate Similarity	NPC78427
0.84	Intermediate Similarity	NPC89099
0.84	Intermediate Similarity	NPC162459
0.84	Intermediate Similarity	NPC16911
0.84	Intermediate Similarity	NPC38471
0.8396	Intermediate Similarity	NPC94650
0.8396	Intermediate Similarity	NPC470311
0.8384	Intermediate Similarity	NPC200054
0.8384	Intermediate Similarity	NPC13949
0.8384	Intermediate Similarity	NPC329910
0.8384	Intermediate Similarity	NPC234564
0.8384	Intermediate Similarity	NPC29410
0.8367	Intermediate Similarity	NPC470386
0.8367	Intermediate Similarity	NPC470385
0.8367	Intermediate Similarity	NPC280804
0.8367	Intermediate Similarity	NPC475118
0.8365	Intermediate Similarity	NPC251824
0.8365	Intermediate Similarity	NPC86852
0.8351	Intermediate Similarity	NPC250753
0.835	Intermediate Similarity	NPC84928
0.835	Intermediate Similarity	NPC98603
0.8333	Intermediate Similarity	NPC309388
0.8333	Intermediate Similarity	NPC200580
0.8333	Intermediate Similarity	NPC164551
0.8333	Intermediate Similarity	NPC475803
0.8333	Intermediate Similarity	NPC194642
0.8318	Intermediate Similarity	NPC126691
0.8317	Intermediate Similarity	NPC218383
0.8317	Intermediate Similarity	NPC470388
0.8317	Intermediate Similarity	NPC293866
0.8317	Intermediate Similarity	NPC94906
0.8302	Intermediate Similarity	NPC471093
0.83	Intermediate Similarity	NPC10864
0.8286	Intermediate Similarity	NPC469984
0.8286	Intermediate Similarity	NPC218123
0.8286	Intermediate Similarity	NPC63841
0.8286	Intermediate Similarity	NPC232133
0.8286	Intermediate Similarity	NPC231278
0.8286	Intermediate Similarity	NPC471094
0.8286	Intermediate Similarity	NPC473410
0.8286	Intermediate Similarity	NPC112895
0.8283	Intermediate Similarity	NPC98639
0.8283	Intermediate Similarity	NPC205173
0.8283	Intermediate Similarity	NPC471624
0.8283	Intermediate Similarity	NPC197158
0.8283	Intermediate Similarity	NPC470229
0.8269	Intermediate Similarity	NPC200957
0.8269	Intermediate Similarity	NPC138908
0.8252	Intermediate Similarity	NPC277074
0.8252	Intermediate Similarity	NPC209298
0.8252	Intermediate Similarity	NPC122811
0.8252	Intermediate Similarity	NPC159442
0.8247	Intermediate Similarity	NPC219937
0.8247	Intermediate Similarity	NPC194485
0.8247	Intermediate Similarity	NPC53890
0.8247	Intermediate Similarity	NPC123252
0.8241	Intermediate Similarity	NPC9848
0.8241	Intermediate Similarity	NPC312017
0.8235	Intermediate Similarity	NPC242666
0.8235	Intermediate Similarity	NPC471790
0.8229	Intermediate Similarity	NPC160304
0.8224	Intermediate Similarity	NPC213320
0.8224	Intermediate Similarity	NPC29505
0.8224	Intermediate Similarity	NPC329953
0.8218	Intermediate Similarity	NPC472028
0.8208	Intermediate Similarity	NPC102741
0.8208	Intermediate Similarity	NPC469983
0.82	Intermediate Similarity	NPC256227
0.82	Intermediate Similarity	NPC470387
0.819	Intermediate Similarity	NPC201908
0.819	Intermediate Similarity	NPC176949
0.819	Intermediate Similarity	NPC186054
0.819	Intermediate Similarity	NPC166993
0.819	Intermediate Similarity	NPC469746
0.819	Intermediate Similarity	NPC78966
0.819	Intermediate Similarity	NPC284732
0.819	Intermediate Similarity	NPC471474
0.8182	Intermediate Similarity	NPC47853
0.8182	Intermediate Similarity	NPC470171
0.8182	Intermediate Similarity	NPC469982
0.8173	Intermediate Similarity	NPC96268
0.8163	Intermediate Similarity	NPC198242
0.8163	Intermediate Similarity	NPC211403
0.8148	Intermediate Similarity	NPC473352
0.8148	Intermediate Similarity	NPC474927
0.8148	Intermediate Similarity	NPC473397
0.8131	Intermediate Similarity	NPC137104
0.8131	Intermediate Similarity	NPC320383
0.8131	Intermediate Similarity	NPC474786
0.8131	Intermediate Similarity	NPC85391
0.8125	Intermediate Similarity	NPC472497
0.8125	Intermediate Similarity	NPC472495
0.8125	Intermediate Similarity	NPC134197
0.8119	Intermediate Similarity	NPC96839
0.8119	Intermediate Similarity	NPC469810
0.8119	Intermediate Similarity	NPC190080
0.8119	Intermediate Similarity	NPC111187
0.8113	Intermediate Similarity	NPC469733
0.8113	Intermediate Similarity	NPC89860
0.8113	Intermediate Similarity	NPC55973
0.8113	Intermediate Similarity	NPC211224
0.8113	Intermediate Similarity	NPC37628
0.8113	Intermediate Similarity	NPC273155
0.8113	Intermediate Similarity	NPC189663
0.8113	Intermediate Similarity	NPC469729
0.81	Intermediate Similarity	NPC157686
0.81	Intermediate Similarity	NPC84018
0.81	Intermediate Similarity	NPC263135
0.81	Intermediate Similarity	NPC259042
0.81	Intermediate Similarity	NPC138245
0.81	Intermediate Similarity	NPC288906
0.81	Intermediate Similarity	NPC231060
0.81	Intermediate Similarity	NPC210214
0.8095	Intermediate Similarity	NPC307660
0.8095	Intermediate Similarity	NPC12823
0.8095	Intermediate Similarity	NPC130511
0.8095	Intermediate Similarity	NPC56656
0.8095	Intermediate Similarity	NPC4115
0.8091	Intermediate Similarity	NPC49492
0.8091	Intermediate Similarity	NPC266728
0.8081	Intermediate Similarity	NPC144739
0.8081	Intermediate Similarity	NPC294263
0.8081	Intermediate Similarity	NPC181594
0.8081	Intermediate Similarity	NPC26046
0.8081	Intermediate Similarity	NPC472496

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 NPC39683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	2074
0.2-0.3	4053
0.3-0.4	1834
0.4-0.5	494
0.5-0.6	218
0.6-0.7	194
0.7-0.8	70
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
0.7757	Intermediate Similarity	NPD6008	Approved
0.7624	Intermediate Similarity	NPD8034	Phase 2
0.7624	Intermediate Similarity	NPD8035	Phase 2
0.7615	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD7320	Approved
0.7593	Intermediate Similarity	NPD6675	Approved
0.7593	Intermediate Similarity	NPD7128	Approved
0.7593	Intermediate Similarity	NPD5739	Approved
0.7593	Intermediate Similarity	NPD6402	Approved
0.7545	Intermediate Similarity	NPD6373	Approved
0.7545	Intermediate Similarity	NPD6372	Approved
0.7542	Intermediate Similarity	NPD7492	Approved
0.7523	Intermediate Similarity	NPD5701	Approved
0.7523	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.7479	Intermediate Similarity	NPD6616	Approved
0.7455	Intermediate Similarity	NPD6899	Approved
0.7455	Intermediate Similarity	NPD6881	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7438	Intermediate Similarity	NPD7319	Approved
0.7436	Intermediate Similarity	NPD6015	Approved
0.7436	Intermediate Similarity	NPD6016	Approved
0.7417	Intermediate Similarity	NPD7078	Approved
0.7417	Intermediate Similarity	NPD8293	Discontinued
0.7411	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD6649	Approved
0.7387	Intermediate Similarity	NPD6013	Approved
0.7387	Intermediate Similarity	NPD6012	Approved
0.7387	Intermediate Similarity	NPD6014	Approved
0.7374	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5988	Approved
0.7373	Intermediate Similarity	NPD6370	Approved
0.7358	Intermediate Similarity	NPD7638	Approved
0.7355	Intermediate Similarity	NPD7736	Approved
0.7333	Intermediate Similarity	NPD7507	Approved
0.7321	Intermediate Similarity	NPD7102	Approved
0.7321	Intermediate Similarity	NPD7290	Approved
0.7321	Intermediate Similarity	NPD6883	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7297	Intermediate Similarity	NPD6011	Approved
0.7281	Intermediate Similarity	NPD8133	Approved
0.7281	Intermediate Similarity	NPD4632	Approved
0.7264	Intermediate Similarity	NPD4755	Approved
0.7257	Intermediate Similarity	NPD8130	Phase 1
0.7257	Intermediate Similarity	NPD6617	Approved
0.7257	Intermediate Similarity	NPD6869	Approved
0.7257	Intermediate Similarity	NPD6847	Approved
0.7212	Intermediate Similarity	NPD6399	Phase 3
0.7193	Intermediate Similarity	NPD8297	Approved
0.7193	Intermediate Similarity	NPD6882	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7168	Intermediate Similarity	NPD4634	Approved
0.713	Intermediate Similarity	NPD5286	Approved
0.713	Intermediate Similarity	NPD4696	Approved
0.713	Intermediate Similarity	NPD4700	Approved
0.713	Intermediate Similarity	NPD5285	Approved
0.7115	Intermediate Similarity	NPD6411	Approved
0.7105	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6084	Phase 2
0.7103	Intermediate Similarity	NPD6083	Phase 2
0.7094	Intermediate Similarity	NPD6009	Approved
0.7075	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD1700	Approved
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7053	Intermediate Similarity	NPD3702	Approved
0.7048	Intermediate Similarity	NPD5778	Approved
0.7048	Intermediate Similarity	NPD5779	Approved
0.7043	Intermediate Similarity	NPD6053	Discontinued
0.7037	Intermediate Similarity	NPD5696	Approved
0.7037	Intermediate Similarity	NPD4225	Approved
0.701	Intermediate Similarity	NPD6697	Approved
0.701	Intermediate Similarity	NPD6115	Approved
0.701	Intermediate Similarity	NPD6118	Approved
0.701	Intermediate Similarity	NPD6114	Approved
0.7009	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD4633	Approved
0.7	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5226	Approved
0.7	Intermediate Similarity	NPD5225	Approved
0.7	Intermediate Similarity	NPD5983	Phase 2
0.7	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD5224	Approved
0.6952	Remote Similarity	NPD7637	Suspended
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7115	Discovery
0.6937	Remote Similarity	NPD5175	Approved
0.6937	Remote Similarity	NPD5174	Approved
0.6935	Remote Similarity	NPD6033	Approved
0.6923	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5328	Approved
0.6916	Remote Similarity	NPD5695	Phase 3
0.6909	Remote Similarity	NPD5223	Approved
0.6907	Remote Similarity	NPD6116	Phase 1
0.6887	Remote Similarity	NPD4202	Approved
0.6885	Remote Similarity	NPD8328	Phase 3
0.6885	Remote Similarity	NPD7604	Phase 2
0.6875	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6921	Approved
0.6852	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD6686	Approved
0.6833	Remote Similarity	NPD7101	Approved
0.6833	Remote Similarity	NPD7100	Approved
0.6832	Remote Similarity	NPD4788	Approved
0.6827	Remote Similarity	NPD6903	Approved
0.6822	Remote Similarity	NPD6001	Approved
0.6814	Remote Similarity	NPD4767	Approved
0.6814	Remote Similarity	NPD4768	Approved
0.6807	Remote Similarity	NPD6317	Approved
0.6804	Remote Similarity	NPD6117	Approved
0.6796	Remote Similarity	NPD7146	Approved
0.6796	Remote Similarity	NPD7334	Approved
0.6796	Remote Similarity	NPD6684	Approved
0.6796	Remote Similarity	NPD5330	Approved
0.6796	Remote Similarity	NPD7521	Approved
0.6796	Remote Similarity	NPD3618	Phase 1
0.6796	Remote Similarity	NPD6409	Approved
0.6792	Remote Similarity	NPD6079	Approved
0.6789	Remote Similarity	NPD7902	Approved
0.6786	Remote Similarity	NPD4754	Approved
0.6783	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6336	Discontinued
0.6765	Remote Similarity	NPD3665	Phase 1
0.6765	Remote Similarity	NPD3666	Approved
0.6765	Remote Similarity	NPD3133	Approved
0.6762	Remote Similarity	NPD4753	Phase 2
0.6759	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6335	Approved
0.675	Remote Similarity	NPD6313	Approved
0.675	Remote Similarity	NPD7328	Approved
0.675	Remote Similarity	NPD6314	Approved
0.675	Remote Similarity	NPD7327	Approved
0.6724	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6909	Approved
0.6721	Remote Similarity	NPD6908	Approved
0.6701	Remote Similarity	NPD3703	Phase 2
0.6697	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5222	Approved
0.6697	Remote Similarity	NPD5221	Approved
0.6696	Remote Similarity	NPD4730	Approved
0.6696	Remote Similarity	NPD4729	Approved
0.6696	Remote Similarity	NPD5128	Approved
0.6694	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD7748	Approved
0.6639	Remote Similarity	NPD8377	Approved
0.6639	Remote Similarity	NPD8294	Approved
0.6636	Remote Similarity	NPD5173	Approved
0.6636	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD5284	Approved
0.6636	Remote Similarity	NPD5281	Approved
0.6635	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5786	Approved
0.6635	Remote Similarity	NPD4249	Approved
0.6606	Remote Similarity	NPD5210	Approved
0.6606	Remote Similarity	NPD4629	Approved
0.6602	Remote Similarity	NPD4786	Approved
0.6598	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6334	Approved
0.6591	Remote Similarity	NPD6333	Approved
0.6585	Remote Similarity	NPD8033	Approved
0.6585	Remote Similarity	NPD8516	Approved
0.6585	Remote Similarity	NPD8379	Approved
0.6585	Remote Similarity	NPD8515	Approved
0.6585	Remote Similarity	NPD8517	Approved
0.6585	Remote Similarity	NPD8335	Approved
0.6585	Remote Similarity	NPD8378	Approved
0.6585	Remote Similarity	NPD8513	Phase 3
0.6585	Remote Similarity	NPD8296	Approved
0.6585	Remote Similarity	NPD8380	Approved
0.6581	Remote Similarity	NPD5247	Approved
0.6581	Remote Similarity	NPD5249	Phase 3
0.6581	Remote Similarity	NPD5250	Approved
0.6581	Remote Similarity	NPD5251	Approved
0.6581	Remote Similarity	NPD6371	Approved
0.6581	Remote Similarity	NPD5248	Approved
0.6571	Remote Similarity	NPD4250	Approved
0.6571	Remote Similarity	NPD4251	Approved
0.6569	Remote Similarity	NPD3667	Approved
0.6569	Remote Similarity	NPD6435	Approved
0.6542	Remote Similarity	NPD5207	Approved
0.6535	Remote Similarity	NPD6928	Phase 2
0.6525	Remote Similarity	NPD5216	Approved
0.6525	Remote Similarity	NPD5215	Approved
0.6525	Remote Similarity	NPD5217	Approved
0.6514	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7900	Approved
0.6509	Remote Similarity	NPD6672	Approved
0.6509	Remote Similarity	NPD5737	Approved
0.6505	Remote Similarity	NPD5362	Discontinued
0.6481	Remote Similarity	NPD7983	Approved
0.6481	Remote Similarity	NPD5693	Phase 1
0.648	Remote Similarity	NPD6067	Discontinued
0.6476	Remote Similarity	NPD6098	Approved
0.6466	Remote Similarity	NPD5954	Clinical (unspecified phase)

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