NPASS Compound

Structure

NPC474101 OpenBabel07101718232D 28 31 0 0 1 0 0 0 0 0999 V2000 2.0792 2.6963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0204 5.0116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4190 -0.1150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 -0.1150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7065 0.9321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4413 1.6558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4413 1.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9190 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9248 2.3280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0705 0.5452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4685 1.9044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8781 4.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4689 1.9330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5218 2.4138 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3966 1.0526 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5218 0.2946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7503 0.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0705 2.1632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1329 0.9911 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9190 0.7510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3966 1.6558 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9248 0.3805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0503 3.6501 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6641 -0.6952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6921 0.6089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7254 2.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6641 3.4036 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 11 2 0 0 0 0 2 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 23 2 0 0 0 0 12 27 1 0 0 0 0 13 9 1 1 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 27 1 6 0 0 0 15 20 1 0 0 0 0 15 21 1 1 0 0 0 16 22 1 1 0 0 0 16 24 1 0 0 0 0 17 25 2 0 0 0 0 18 21 1 0 0 0 0 18 26 2 0 0 0 0 19 22 1 1 0 0 0 19 28 1 0 0 0 0 21 5 1 1 0 0 0 22 17 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.2
Volume:	397.038
LogP:	2.299
LogD:	2.035
LogS:	-4.068
# Rotatable Bonds:	2
TPSA:	93.2
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	6.058
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	2.594589750515297e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.102

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	71.69735717773438%
Volume Distribution (VD):	1.427
Pgp-substrate:	39.662532806396484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.143
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.258

ADMET: Excretion

Clearance (CL):	4.517
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.874
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.464
Carcinogencity:	0.16
Eye Corrosion:	0.202
Eye Irritation:	0.159
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC474101

Natural Product ID:	NPC474101
*Common Name:**	SGVAXGGRQGLXKO-TUUMUHJWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SGVAXGGRQGLXKO-TUUMUHJWSA-N
Standard InCHI:	InChI=1S/C22H30O6/c1-11-13-9-14(27-12(2)23)18(26)21(5)8-6-7-20(3,4)15(21)10-16(24)22(17(11)25)19(13)28-22/h13-16,19,24H,1,6-10H2,2-5H3/t13-,14-,15+,16+,19+,21+,22-/m0/s1
SMILES:	CC(=O)OC1CC2C3C(O3)(C(CC4C(CCCC4(C1=O)C)(C)C)O)C(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461486
PubChem CID:	10000469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0003677] Alpha-acyloxy carbonyl compounds [CHEMONTID:0003420] Alpha-acyloxy ketones

*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
NPO9759	Croton kongensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828479]
NPO9759	Croton kongensis	Species	Euphorbiaceae	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	4
MIC	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	0.9	ug.mL-1	PMID[482523]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.4	ug.mL-1	PMID[482523]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.2	ug.mL-1	PMID[482523]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	6.25	ug.mL-1	PMID[482523]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	1.0	ug.mL-1	PMID[482523]

☑ 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 NPC474101 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	260
0.1-0.2	1937
0.2-0.3	6809
0.3-0.4	12134
0.4-0.5	9102
0.5-0.6	7427
0.6-0.7	4266
0.7-0.8	752
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8208	Intermediate Similarity	NPC310586
0.8198	Intermediate Similarity	NPC300051
0.81	Intermediate Similarity	NPC65359
0.8095	Intermediate Similarity	NPC201718
0.8091	Intermediate Similarity	NPC470281
0.8058	Intermediate Similarity	NPC39859
0.8058	Intermediate Similarity	NPC470883
0.8058	Intermediate Similarity	NPC76862
0.8058	Intermediate Similarity	NPC158416
0.8039	Intermediate Similarity	NPC190294
0.802	Intermediate Similarity	NPC469627
0.8019	Intermediate Similarity	NPC15396
0.8	Intermediate Similarity	NPC471093
0.7982	Intermediate Similarity	NPC273155
0.7982	Intermediate Similarity	NPC112895
0.7982	Intermediate Similarity	NPC218123
0.7982	Intermediate Similarity	NPC211224
0.7982	Intermediate Similarity	NPC475401
0.7982	Intermediate Similarity	NPC231278
0.7963	Intermediate Similarity	NPC44004
0.7961	Intermediate Similarity	NPC322188
0.7944	Intermediate Similarity	NPC209298
0.7944	Intermediate Similarity	NPC277074
0.7944	Intermediate Similarity	NPC87927
0.7941	Intermediate Similarity	NPC475488
0.7928	Intermediate Similarity	NPC29505
0.7928	Intermediate Similarity	NPC213320
0.7925	Intermediate Similarity	NPC471767
0.7925	Intermediate Similarity	NPC52899
0.7925	Intermediate Similarity	NPC98225
0.7925	Intermediate Similarity	NPC289148
0.7925	Intermediate Similarity	NPC163963
0.7913	Intermediate Similarity	NPC477092
0.7909	Intermediate Similarity	NPC102741
0.7895	Intermediate Similarity	NPC475305
0.789	Intermediate Similarity	NPC166993
0.789	Intermediate Similarity	NPC176949
0.789	Intermediate Similarity	NPC201908
0.7885	Intermediate Similarity	NPC476009
0.7857	Intermediate Similarity	NPC473397
0.7857	Intermediate Similarity	NPC474927
0.7857	Intermediate Similarity	NPC473352
0.785	Intermediate Similarity	NPC76866
0.785	Intermediate Similarity	NPC88203
0.785	Intermediate Similarity	NPC304832
0.785	Intermediate Similarity	NPC286519
0.785	Intermediate Similarity	NPC214946
0.785	Intermediate Similarity	NPC148628
0.785	Intermediate Similarity	NPC246736
0.785	Intermediate Similarity	NPC250594
0.7838	Intermediate Similarity	NPC100908
0.783	Intermediate Similarity	NPC287676
0.783	Intermediate Similarity	NPC470388
0.7818	Intermediate Similarity	NPC471094
0.7818	Intermediate Similarity	NPC473410
0.7818	Intermediate Similarity	NPC469984
0.7818	Intermediate Similarity	NPC63841
0.7818	Intermediate Similarity	NPC189663
0.7818	Intermediate Similarity	NPC89860
0.7818	Intermediate Similarity	NPC55973
0.781	Intermediate Similarity	NPC328562
0.781	Intermediate Similarity	NPC323421
0.7798	Intermediate Similarity	NPC138908
0.7798	Intermediate Similarity	NPC200957
0.7798	Intermediate Similarity	NPC265127
0.7788	Intermediate Similarity	NPC471252
0.7788	Intermediate Similarity	NPC194100
0.7788	Intermediate Similarity	NPC475900
0.7788	Intermediate Similarity	NPC132668
0.7778	Intermediate Similarity	NPC122811
0.7778	Intermediate Similarity	NPC469985
0.7778	Intermediate Similarity	NPC216114
0.7778	Intermediate Similarity	NPC159442
0.7768	Intermediate Similarity	NPC157476
0.7768	Intermediate Similarity	NPC214797
0.7768	Intermediate Similarity	NPC118860
0.7768	Intermediate Similarity	NPC472003
0.7768	Intermediate Similarity	NPC231589
0.7757	Intermediate Similarity	NPC477356
0.7757	Intermediate Similarity	NPC46848
0.775	Intermediate Similarity	NPC473253
0.7748	Intermediate Similarity	NPC118721
0.7748	Intermediate Similarity	NPC252679
0.7748	Intermediate Similarity	NPC470257
0.7748	Intermediate Similarity	NPC475922
0.7736	Intermediate Similarity	NPC16911
0.7736	Intermediate Similarity	NPC474793
0.7736	Intermediate Similarity	NPC78427
0.7736	Intermediate Similarity	NPC471038
0.7727	Intermediate Similarity	NPC471474
0.7727	Intermediate Similarity	NPC471461
0.7727	Intermediate Similarity	NPC67745
0.7727	Intermediate Similarity	NPC186054
0.7723	Intermediate Similarity	NPC315911
0.7719	Intermediate Similarity	NPC243354
0.7714	Intermediate Similarity	NPC31645
0.7714	Intermediate Similarity	NPC91771
0.7714	Intermediate Similarity	NPC13949
0.7714	Intermediate Similarity	NPC142529
0.7706	Intermediate Similarity	NPC301787
0.7706	Intermediate Similarity	NPC84928
0.7706	Intermediate Similarity	NPC202793
0.7706	Intermediate Similarity	NPC474558
0.7706	Intermediate Similarity	NPC96268
0.7706	Intermediate Similarity	NPC98603
0.7699	Intermediate Similarity	NPC473877
0.7699	Intermediate Similarity	NPC170487
0.7685	Intermediate Similarity	NPC275990
0.7679	Intermediate Similarity	NPC471476
0.7679	Intermediate Similarity	NPC473324
0.7679	Intermediate Similarity	NPC161816
0.7679	Intermediate Similarity	NPC320383
0.7679	Intermediate Similarity	NPC115257
0.7679	Intermediate Similarity	NPC85391
0.7679	Intermediate Similarity	NPC137104
0.7679	Intermediate Similarity	NPC474786
0.767	Intermediate Similarity	NPC70251
0.767	Intermediate Similarity	NPC475881
0.7664	Intermediate Similarity	NPC471381
0.7664	Intermediate Similarity	NPC267921
0.7664	Intermediate Similarity	NPC186861
0.7658	Intermediate Similarity	NPC9013
0.7658	Intermediate Similarity	NPC117604
0.7652	Intermediate Similarity	NPC270478
0.7652	Intermediate Similarity	NPC229752
0.7652	Intermediate Similarity	NPC88945
0.7642	Intermediate Similarity	NPC111187
0.7642	Intermediate Similarity	NPC311904
0.7642	Intermediate Similarity	NPC111348
0.7642	Intermediate Similarity	NPC474313
0.7642	Intermediate Similarity	NPC87090
0.7642	Intermediate Similarity	NPC190080
0.7636	Intermediate Similarity	NPC37600
0.7636	Intermediate Similarity	NPC130511
0.7636	Intermediate Similarity	NPC50535
0.7636	Intermediate Similarity	NPC314244
0.7636	Intermediate Similarity	NPC222833
0.7636	Intermediate Similarity	NPC307660
0.7636	Intermediate Similarity	NPC56656
0.7632	Intermediate Similarity	NPC202889
0.7632	Intermediate Similarity	NPC194273
0.7627	Intermediate Similarity	NPC472000
0.7627	Intermediate Similarity	NPC472001
0.7627	Intermediate Similarity	NPC472401
0.7627	Intermediate Similarity	NPC471999
0.7623	Intermediate Similarity	NPC470880
0.7619	Intermediate Similarity	NPC470232
0.7619	Intermediate Similarity	NPC163228
0.7615	Intermediate Similarity	NPC139347
0.7615	Intermediate Similarity	NPC470310
0.7615	Intermediate Similarity	NPC96217
0.7611	Intermediate Similarity	NPC475495
0.7611	Intermediate Similarity	NPC317107
0.7611	Intermediate Similarity	NPC56025
0.7611	Intermediate Similarity	NPC94650
0.7611	Intermediate Similarity	NPC63244
0.7611	Intermediate Similarity	NPC122339
0.7607	Intermediate Similarity	NPC319570
0.7607	Intermediate Similarity	NPC473203
0.7596	Intermediate Similarity	NPC109414
0.7596	Intermediate Similarity	NPC475788
0.7593	Intermediate Similarity	NPC476270
0.7593	Intermediate Similarity	NPC236585
0.7593	Intermediate Similarity	NPC39683
0.7593	Intermediate Similarity	NPC252614
0.7593	Intermediate Similarity	NPC148279
0.7593	Intermediate Similarity	NPC471790
0.7593	Intermediate Similarity	NPC474339
0.7593	Intermediate Similarity	NPC164598
0.7589	Intermediate Similarity	NPC304495
0.7589	Intermediate Similarity	NPC274827
0.7589	Intermediate Similarity	NPC258543
0.7589	Intermediate Similarity	NPC131903
0.7589	Intermediate Similarity	NPC241927
0.7586	Intermediate Similarity	NPC476712
0.7586	Intermediate Similarity	NPC476713
0.7586	Intermediate Similarity	NPC78836
0.7586	Intermediate Similarity	NPC473304
0.7586	Intermediate Similarity	NPC156252
0.7583	Intermediate Similarity	NPC473255
0.7573	Intermediate Similarity	NPC246173
0.757	Intermediate Similarity	NPC28864
0.757	Intermediate Similarity	NPC38471
0.757	Intermediate Similarity	NPC89099
0.757	Intermediate Similarity	NPC20479
0.757	Intermediate Similarity	NPC26270
0.757	Intermediate Similarity	NPC98837
0.757	Intermediate Similarity	NPC38296
0.757	Intermediate Similarity	NPC477355
0.757	Intermediate Similarity	NPC162459
0.7568	Intermediate Similarity	NPC86852
0.7568	Intermediate Similarity	NPC474421
0.7568	Intermediate Similarity	NPC324327
0.7568	Intermediate Similarity	NPC72813
0.7568	Intermediate Similarity	NPC477513
0.7568	Intermediate Similarity	NPC58370
0.7568	Intermediate Similarity	NPC251824
0.7568	Intermediate Similarity	NPC43285
0.7568	Intermediate Similarity	NPC326994
0.7568	Intermediate Similarity	NPC194620

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 NPC474101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	2587
0.2-0.3	3870
0.3-0.4	1550
0.4-0.5	455
0.5-0.6	254
0.6-0.7	143
0.7-0.8	16
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
0.7845	Intermediate Similarity	NPD6319	Approved
0.7478	Intermediate Similarity	NPD4632	Approved
0.7438	Intermediate Similarity	NPD7492	Approved
0.7411	Intermediate Similarity	NPD5697	Approved
0.7395	Intermediate Similarity	NPD6054	Approved
0.7391	Intermediate Similarity	NPD8297	Approved
0.7377	Intermediate Similarity	NPD6616	Approved
0.7368	Intermediate Similarity	NPD6371	Approved
0.7345	Intermediate Similarity	NPD6899	Approved
0.7345	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6016	Approved
0.7333	Intermediate Similarity	NPD6015	Approved
0.7321	Intermediate Similarity	NPD6402	Approved
0.7321	Intermediate Similarity	NPD5739	Approved
0.7321	Intermediate Similarity	NPD6675	Approved
0.7321	Intermediate Similarity	NPD7128	Approved
0.7317	Intermediate Similarity	NPD7078	Approved
0.7304	Intermediate Similarity	NPD6649	Approved
0.7304	Intermediate Similarity	NPD6650	Approved
0.7288	Intermediate Similarity	NPD6009	Approved
0.7281	Intermediate Similarity	NPD6013	Approved
0.7281	Intermediate Similarity	NPD6014	Approved
0.7281	Intermediate Similarity	NPD6373	Approved
0.7281	Intermediate Similarity	NPD6012	Approved
0.7281	Intermediate Similarity	NPD6372	Approved
0.7273	Intermediate Similarity	NPD5988	Approved
0.7273	Intermediate Similarity	NPD6370	Approved
0.7273	Intermediate Similarity	NPD1700	Approved
0.7258	Intermediate Similarity	NPD7736	Approved
0.7257	Intermediate Similarity	NPD5701	Approved
0.725	Intermediate Similarity	NPD6059	Approved
0.7217	Intermediate Similarity	NPD7290	Approved
0.7217	Intermediate Similarity	NPD7102	Approved
0.7217	Intermediate Similarity	NPD6883	Approved
0.7217	Intermediate Similarity	NPD4634	Approved
0.7213	Intermediate Similarity	NPD7604	Phase 2
0.7193	Intermediate Similarity	NPD6011	Approved
0.7193	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7320	Approved
0.719	Intermediate Similarity	NPD5983	Phase 2
0.7177	Intermediate Similarity	NPD8293	Discontinued
0.7168	Intermediate Similarity	NPD6008	Approved
0.7156	Intermediate Similarity	NPD6083	Phase 2
0.7156	Intermediate Similarity	NPD6084	Phase 2
0.7155	Intermediate Similarity	NPD8130	Phase 1
0.7155	Intermediate Similarity	NPD6869	Approved
0.7155	Intermediate Similarity	NPD6617	Approved
0.7155	Intermediate Similarity	NPD6847	Approved
0.713	Intermediate Similarity	NPD5695	Phase 3
0.7094	Intermediate Similarity	NPD6882	Approved
0.7091	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD7115	Discovery
0.696	Remote Similarity	NPD6336	Discontinued
0.6957	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6274	Approved
0.6881	Remote Similarity	NPD5282	Discontinued
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.6864	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4755	Approved
0.681	Remote Similarity	NPD6412	Phase 2
0.68	Remote Similarity	NPD8328	Phase 3
0.6754	Remote Similarity	NPD5211	Phase 2
0.6754	Remote Similarity	NPD5224	Approved
0.6754	Remote Similarity	NPD5225	Approved
0.6754	Remote Similarity	NPD5226	Approved
0.6754	Remote Similarity	NPD4633	Approved
0.6748	Remote Similarity	NPD7100	Approved
0.6748	Remote Similarity	NPD7101	Approved
0.6726	Remote Similarity	NPD4700	Approved
0.6721	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6317	Approved
0.6719	Remote Similarity	NPD6033	Approved
0.6696	Remote Similarity	NPD5174	Approved
0.6696	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6638	Remote Similarity	NPD5141	Approved
0.6638	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4225	Approved
0.6636	Remote Similarity	NPD6399	Phase 3
0.6615	Remote Similarity	NPD5956	Approved
0.6612	Remote Similarity	NPD8133	Approved
0.661	Remote Similarity	NPD6686	Approved
0.6606	Remote Similarity	NPD46	Approved
0.6606	Remote Similarity	NPD6698	Approved
0.6604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4788	Approved
0.6562	Remote Similarity	NPD7507	Approved
0.6555	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7983	Approved
0.6538	Remote Similarity	NPD5369	Approved
0.6529	Remote Similarity	NPD6053	Discontinued
0.6514	Remote Similarity	NPD6673	Approved
0.6514	Remote Similarity	NPD6080	Approved
0.6514	Remote Similarity	NPD6904	Approved
0.6508	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6908	Approved
0.6508	Remote Similarity	NPD6921	Approved
0.6508	Remote Similarity	NPD6909	Approved
0.648	Remote Similarity	NPD4522	Approved
0.6476	Remote Similarity	NPD6435	Approved
0.6471	Remote Similarity	NPD5128	Approved
0.6471	Remote Similarity	NPD4730	Approved
0.6471	Remote Similarity	NPD4729	Approved
0.6455	Remote Similarity	NPD5785	Approved
0.6455	Remote Similarity	NPD5692	Phase 3
0.6441	Remote Similarity	NPD4767	Approved
0.6441	Remote Similarity	NPD4768	Approved
0.6422	Remote Similarity	NPD5737	Approved
0.6422	Remote Similarity	NPD6672	Approved
0.641	Remote Similarity	NPD4754	Approved
0.6396	Remote Similarity	NPD8034	Phase 2
0.6396	Remote Similarity	NPD6411	Approved
0.6396	Remote Similarity	NPD5694	Approved
0.6396	Remote Similarity	NPD6050	Approved
0.6396	Remote Similarity	NPD5281	Approved
0.6396	Remote Similarity	NPD8035	Phase 2
0.6396	Remote Similarity	NPD5693	Phase 1
0.6396	Remote Similarity	NPD5284	Approved
0.6389	Remote Similarity	NPD6098	Approved
0.6389	Remote Similarity	NPD5786	Approved
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5251	Approved
0.6364	Remote Similarity	NPD5249	Phase 3
0.6364	Remote Similarity	NPD1695	Approved
0.6364	Remote Similarity	NPD5250	Approved
0.6364	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD5247	Approved
0.6339	Remote Similarity	NPD5779	Approved
0.6339	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD5222	Approved
0.6316	Remote Similarity	NPD4697	Phase 3
0.6316	Remote Similarity	NPD5221	Approved
0.6316	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5216	Approved
0.6311	Remote Similarity	NPD5217	Approved
0.6311	Remote Similarity	NPD5215	Approved
0.6296	Remote Similarity	NPD5363	Approved
0.6286	Remote Similarity	NPD5368	Approved
0.6277	Remote Similarity	NPD6334	Approved
0.6277	Remote Similarity	NPD6333	Approved
0.6261	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.624	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD6684	Approved
0.6239	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7334	Approved
0.6239	Remote Similarity	NPD5690	Phase 2
0.6239	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD5344	Discontinued
0.6239	Remote Similarity	NPD6409	Approved
0.6239	Remote Similarity	NPD5279	Phase 3
0.6239	Remote Similarity	NPD5330	Approved
0.623	Remote Similarity	NPD5169	Approved
0.623	Remote Similarity	NPD5135	Approved
0.623	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6101	Approved
0.6207	Remote Similarity	NPD7638	Approved
0.6204	Remote Similarity	NPD4197	Approved
0.6204	Remote Similarity	NPD3133	Approved
0.6204	Remote Similarity	NPD3665	Phase 1
0.6204	Remote Similarity	NPD3666	Approved
0.6195	Remote Similarity	NPD4202	Approved
0.6179	Remote Similarity	NPD5127	Approved
0.6168	Remote Similarity	NPD4269	Approved
0.6168	Remote Similarity	NPD4270	Approved
0.6161	Remote Similarity	NPD7838	Discovery
0.6154	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD7639	Approved
0.6148	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5329	Approved
0.6147	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6903	Approved
0.6126	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5959	Approved
0.6117	Remote Similarity	NPD3702	Approved
0.6116	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6079	Approved
0.6091	Remote Similarity	NPD5280	Approved
0.6091	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4694	Approved
0.6087	Remote Similarity	NPD5654	Approved
0.6083	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD8080	Discontinued
0.6074	Remote Similarity	NPD7260	Phase 2
0.6071	Remote Similarity	NPD5328	Approved
0.6055	Remote Similarity	NPD4786	Approved
0.6048	Remote Similarity	NPD8413	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