NPASS Compound

Structure

NPC194273 OpenBabel07101718192D 28 32 0 0 1 0 0 0 0 0999 V2000 2.8998 2.3308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9425 2.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7600 -0.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7601 -0.8548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4225 2.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0751 2.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8545 1.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3307 2.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0690 2.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1397 2.6095 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0215 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2256 1.4587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6397 1.0707 0.0000 C 0 0 0 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 -1.2471 0.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6074 1.0893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6397 1.0707 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6289 0.3507 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0541 3.9714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2275 0.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6288 0.3357 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 -1.2106 2.4586 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 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 6 14 2 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 27 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 28 1 0 0 0 0 13 5 1 1 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 6 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 6 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 22 1 1 0 0 0 18 25 1 0 0 0 0 20 10 1 6 0 0 0 21 22 1 6 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.19
Volume:	388.481
LogP:	2.375
LogD:	1.671
LogS:	-3.923
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	6.975
Fsp3:	0.727
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:	-4.92
MDCK Permeability:	3.094510975643061e-05
Pgp-inhibitor:	0.554
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.135

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.594
Plasma Protein Binding (PPB):	78.95487213134766%
Volume Distribution (VD):	1.497
Pgp-substrate:	31.11774253845215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.708
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	2.026
Half-life (T1/2):	0.441

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.282
AMES Toxicity:	0.58
Rat Oral Acute Toxicity:	0.471
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.106
Carcinogencity:	0.772
Eye Corrosion:	0.004
Eye Irritation:	0.035
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC194273

Natural Product ID:	NPC194273
*Common Name:**	Isoadenolin I
IUPAC Name:	n.a.
Synonyms:	isoadenolin I
Standard InCHIKey:	YANOCUIQFVTZFB-QMDSWMCQSA-N
Standard InCHI:	InChI=1S/C22H28O6/c1-11-13-5-6-14-20-10-27-22(26,21(14,9-13)17(11)24)18(25)16(20)19(3,4)8-7-15(20)28-12(2)23/h6,13,15-16,18,25-26H,1,5,7-10H2,2-4H3/t13-,15+,16-,18+,20-,21+,22-/m1/s1
SMILES:	CC(=O)O[C@H]1CCC([C@@H]2[C@]31CO[C@]([C@H]2O)([C@]12C3=CC[C@H](C1)C(=C)C2=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802174
PubChem CID:	56683363
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002012] Oxanes

*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
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21534539]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	aerial parts	Shangrila, Yunnan Province, China	2008-AUG	PMID[21534539]
NPO18055	Isodon adenolomus	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2600.0	nM	PMID[528449]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	3000.0	nM	PMID[528449]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5000.0	nM	PMID[528449]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2600.0	nM	PMID[528449]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	3100.0	nM	PMID[528449]

☑ 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 NPC194273 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	248
0.1-0.2	1518
0.2-0.3	4613
0.3-0.4	8172
0.4-0.5	11990
0.5-0.6	6818
0.6-0.7	5115
0.7-0.8	2956
0.8-0.85	1053
0.85-0.9	165
0.9-0.95	44
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9717	High Similarity	NPC243354
0.9623	High Similarity	NPC320118
0.9619	High Similarity	NPC471243
0.9333	High Similarity	NPC471094
0.9333	High Similarity	NPC473410
0.9333	High Similarity	NPC469984
0.9252	High Similarity	NPC213320
0.9245	High Similarity	NPC102741
0.9238	High Similarity	NPC471474
0.9182	High Similarity	NPC470171
0.9182	High Similarity	NPC218970
0.9167	High Similarity	NPC474927
0.9167	High Similarity	NPC473397
0.9167	High Similarity	NPC473352
0.9159	High Similarity	NPC137104
0.9159	High Similarity	NPC474786
0.9159	High Similarity	NPC85391
0.9159	High Similarity	NPC471093
0.9159	High Similarity	NPC320383
0.9151	High Similarity	NPC89860
0.9151	High Similarity	NPC63841
0.9151	High Similarity	NPC189663
0.9143	High Similarity	NPC56656
0.9143	High Similarity	NPC130511
0.9143	High Similarity	NPC307660
0.9083	High Similarity	NPC132668
0.9074	High Similarity	NPC29505
0.9065	High Similarity	NPC274827
0.9065	High Similarity	NPC131903
0.9065	High Similarity	NPC118721
0.9065	High Similarity	NPC252679
0.9057	High Similarity	NPC186054
0.8991	High Similarity	NPC205534
0.8981	High Similarity	NPC471476
0.8972	High Similarity	NPC55973
0.8919	High Similarity	NPC229752
0.8919	High Similarity	NPC88945
0.8909	High Similarity	NPC471252
0.8899	High Similarity	NPC201992
0.8899	High Similarity	NPC63244
0.8879	High Similarity	NPC471461
0.8879	High Similarity	NPC67745
0.8868	High Similarity	NPC202793
0.8839	High Similarity	NPC78836
0.8818	High Similarity	NPC11252
0.8818	High Similarity	NPC471244
0.8818	High Similarity	NPC289312
0.8807	High Similarity	NPC473324
0.8774	High Similarity	NPC159442
0.8774	High Similarity	NPC139347
0.8772	High Similarity	NPC476961
0.8762	High Similarity	NPC14634
0.8761	High Similarity	NPC204552
0.8761	High Similarity	NPC297179
0.8761	High Similarity	NPC188667
0.8739	High Similarity	NPC94141
0.8739	High Similarity	NPC194100
0.8739	High Similarity	NPC471248
0.8739	High Similarity	NPC51978
0.8727	High Similarity	NPC122339
0.8727	High Similarity	NPC56025
0.8716	High Similarity	NPC143706
0.8716	High Similarity	NPC472534
0.8696	High Similarity	NPC102822
0.8696	High Similarity	NPC477046
0.8692	High Similarity	NPC96268
0.8684	High Similarity	NPC469488
0.8673	High Similarity	NPC474654
0.8673	High Similarity	NPC287343
0.8673	High Similarity	NPC97908
0.8673	High Similarity	NPC122033
0.8673	High Similarity	NPC470854
0.8673	High Similarity	NPC473304
0.8661	High Similarity	NPC17165
0.8661	High Similarity	NPC474906
0.8661	High Similarity	NPC18547
0.8649	High Similarity	NPC145625
0.8649	High Similarity	NPC473303
0.8649	High Similarity	NPC157929
0.8649	High Similarity	NPC471245
0.8624	High Similarity	NPC232133
0.8624	High Similarity	NPC293850
0.8624	High Similarity	NPC273155
0.8611	High Similarity	NPC102352
0.8609	High Similarity	NPC112038
0.8598	High Similarity	NPC277074
0.8598	High Similarity	NPC209298
0.8596	High Similarity	NPC17772
0.8584	High Similarity	NPC235539
0.8584	High Similarity	NPC134869
0.8584	High Similarity	NPC152199
0.8571	High Similarity	NPC255017
0.8571	High Similarity	NPC49451
0.8571	High Similarity	NPC7921
0.8571	High Similarity	NPC208998
0.8559	High Similarity	NPC171888
0.8559	High Similarity	NPC47113
0.8559	High Similarity	NPC174367
0.8559	High Similarity	NPC146945
0.8545	High Similarity	NPC469983
0.8534	High Similarity	NPC202051
0.8532	High Similarity	NPC3316
0.8532	High Similarity	NPC144854
0.8532	High Similarity	NPC469746
0.8532	High Similarity	NPC166993
0.8522	High Similarity	NPC470777
0.8522	High Similarity	NPC476529
0.8522	High Similarity	NPC475775
0.8519	High Similarity	NPC474558
0.8509	High Similarity	NPC470959
0.8509	High Similarity	NPC476965
0.8509	High Similarity	NPC309433
0.8509	High Similarity	NPC473968
0.8505	High Similarity	NPC309388
0.8505	High Similarity	NPC475803
0.8491	Intermediate Similarity	NPC470388
0.8482	Intermediate Similarity	NPC302146
0.8475	Intermediate Similarity	NPC130229
0.8475	Intermediate Similarity	NPC473255
0.8475	Intermediate Similarity	NPC470922
0.8468	Intermediate Similarity	NPC474567
0.8455	Intermediate Similarity	NPC112895
0.8455	Intermediate Similarity	NPC154608
0.8455	Intermediate Similarity	NPC192813
0.8455	Intermediate Similarity	NPC231278
0.8455	Intermediate Similarity	NPC218123
0.8455	Intermediate Similarity	NPC277017
0.8448	Intermediate Similarity	NPC107338
0.8448	Intermediate Similarity	NPC109607
0.844	Intermediate Similarity	NPC200957
0.844	Intermediate Similarity	NPC138908
0.8435	Intermediate Similarity	NPC251310
0.8426	Intermediate Similarity	NPC122811
0.8421	Intermediate Similarity	NPC328374
0.8421	Intermediate Similarity	NPC207217
0.8421	Intermediate Similarity	NPC44170
0.8421	Intermediate Similarity	NPC96312
0.8421	Intermediate Similarity	NPC251236
0.8421	Intermediate Similarity	NPC40632
0.8417	Intermediate Similarity	NPC245094
0.8407	Intermediate Similarity	NPC251309
0.8403	Intermediate Similarity	NPC293112
0.8396	Intermediate Similarity	NPC474793
0.8393	Intermediate Similarity	NPC329953
0.8393	Intermediate Similarity	NPC263827
0.8393	Intermediate Similarity	NPC250481
0.8393	Intermediate Similarity	NPC285410
0.8393	Intermediate Similarity	NPC472003
0.839	Intermediate Similarity	NPC469789
0.839	Intermediate Similarity	NPC11895
0.8378	Intermediate Similarity	NPC218853
0.8378	Intermediate Similarity	NPC118225
0.8378	Intermediate Similarity	NPC469744
0.8364	Intermediate Similarity	NPC230541
0.8364	Intermediate Similarity	NPC293512
0.8364	Intermediate Similarity	NPC96333
0.8364	Intermediate Similarity	NPC88833
0.8362	Intermediate Similarity	NPC473203
0.8362	Intermediate Similarity	NPC476960
0.8349	Intermediate Similarity	NPC152966
0.8349	Intermediate Similarity	NPC475036
0.8349	Intermediate Similarity	NPC301787
0.8348	Intermediate Similarity	NPC470775
0.8348	Intermediate Similarity	NPC176513
0.8348	Intermediate Similarity	NPC477252
0.8347	Intermediate Similarity	NPC476966
0.8333	Intermediate Similarity	NPC116024
0.8333	Intermediate Similarity	NPC287423
0.8333	Intermediate Similarity	NPC470882
0.8333	Intermediate Similarity	NPC471398
0.8333	Intermediate Similarity	NPC117712
0.8333	Intermediate Similarity	NPC475633
0.8333	Intermediate Similarity	NPC473798
0.8333	Intermediate Similarity	NPC470919
0.8333	Intermediate Similarity	NPC469877
0.8333	Intermediate Similarity	NPC470953
0.8333	Intermediate Similarity	NPC473882
0.8319	Intermediate Similarity	NPC177820
0.8319	Intermediate Similarity	NPC7850
0.8319	Intermediate Similarity	NPC6615
0.8319	Intermediate Similarity	NPC248202
0.8319	Intermediate Similarity	NPC233003
0.8319	Intermediate Similarity	NPC30188
0.8319	Intermediate Similarity	NPC24651
0.8305	Intermediate Similarity	NPC269642
0.8305	Intermediate Similarity	NPC471965
0.8305	Intermediate Similarity	NPC170538
0.8304	Intermediate Similarity	NPC129340
0.8304	Intermediate Similarity	NPC210005
0.8291	Intermediate Similarity	NPC471406
0.8288	Intermediate Similarity	NPC469729
0.8288	Intermediate Similarity	NPC469733
0.8288	Intermediate Similarity	NPC295389
0.8276	Intermediate Similarity	NPC470776
0.8276	Intermediate Similarity	NPC239293
0.8273	Intermediate Similarity	NPC210178
0.8273	Intermediate Similarity	NPC4115
0.8273	Intermediate Similarity	NPC12823
0.8273	Intermediate Similarity	NPC222833
0.8264	Intermediate Similarity	NPC311534

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 NPC194273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1777
0.2-0.3	3850
0.3-0.4	2139
0.4-0.5	636
0.5-0.6	272
0.6-0.7	148
0.7-0.8	103
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD8328	Phase 3
0.8136	Intermediate Similarity	NPD6319	Approved
0.8034	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD7492	Approved
0.7983	Intermediate Similarity	NPD6054	Approved
0.7967	Intermediate Similarity	NPD7736	Approved
0.7951	Intermediate Similarity	NPD6616	Approved
0.7931	Intermediate Similarity	NPD4632	Approved
0.7917	Intermediate Similarity	NPD6016	Approved
0.7917	Intermediate Similarity	NPD6015	Approved
0.7895	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7078	Approved
0.7881	Intermediate Similarity	NPD6009	Approved
0.7881	Intermediate Similarity	NPD7115	Discovery
0.7876	Intermediate Similarity	NPD6412	Phase 2
0.7851	Intermediate Similarity	NPD5988	Approved
0.7851	Intermediate Similarity	NPD6370	Approved
0.7833	Intermediate Similarity	NPD6059	Approved
0.776	Intermediate Similarity	NPD7319	Approved
0.7742	Intermediate Similarity	NPD8293	Discontinued
0.7719	Intermediate Similarity	NPD5697	Approved
0.7692	Intermediate Similarity	NPD6882	Approved
0.7692	Intermediate Similarity	NPD8297	Approved
0.7672	Intermediate Similarity	NPD4634	Approved
0.7661	Intermediate Similarity	NPD7507	Approved
0.7652	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD6899	Approved
0.7652	Intermediate Similarity	NPD6881	Approved
0.7632	Intermediate Similarity	NPD6402	Approved
0.7632	Intermediate Similarity	NPD5739	Approved
0.7632	Intermediate Similarity	NPD7128	Approved
0.7632	Intermediate Similarity	NPD6008	Approved
0.7632	Intermediate Similarity	NPD6675	Approved
0.7607	Intermediate Similarity	NPD6650	Approved
0.7607	Intermediate Similarity	NPD6649	Approved
0.7593	Intermediate Similarity	NPD6399	Phase 3
0.7586	Intermediate Similarity	NPD6373	Approved
0.7586	Intermediate Similarity	NPD6014	Approved
0.7586	Intermediate Similarity	NPD6372	Approved
0.7586	Intermediate Similarity	NPD6012	Approved
0.7586	Intermediate Similarity	NPD6013	Approved
0.7565	Intermediate Similarity	NPD5701	Approved
0.7521	Intermediate Similarity	NPD7102	Approved
0.7521	Intermediate Similarity	NPD6883	Approved
0.7521	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.748	Intermediate Similarity	NPD8516	Approved
0.748	Intermediate Similarity	NPD8513	Phase 3
0.748	Intermediate Similarity	NPD5983	Phase 2
0.748	Intermediate Similarity	NPD8517	Approved
0.748	Intermediate Similarity	NPD8515	Approved
0.7458	Intermediate Similarity	NPD8130	Phase 1
0.7458	Intermediate Similarity	NPD6617	Approved
0.7458	Intermediate Similarity	NPD6869	Approved
0.7458	Intermediate Similarity	NPD6847	Approved
0.7411	Intermediate Similarity	NPD4225	Approved
0.736	Intermediate Similarity	NPD7604	Phase 2
0.7345	Intermediate Similarity	NPD5286	Approved
0.7345	Intermediate Similarity	NPD4696	Approved
0.7345	Intermediate Similarity	NPD5285	Approved
0.7339	Intermediate Similarity	NPD6079	Approved
0.7339	Intermediate Similarity	NPD6411	Approved
0.7333	Intermediate Similarity	NPD8133	Approved
0.7321	Intermediate Similarity	NPD7902	Approved
0.7321	Intermediate Similarity	NPD4755	Approved
0.7315	Intermediate Similarity	NPD5328	Approved
0.7288	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6033	Approved
0.7244	Intermediate Similarity	NPD6336	Discontinued
0.7232	Intermediate Similarity	NPD4697	Phase 3
0.7232	Intermediate Similarity	NPD5221	Approved
0.7232	Intermediate Similarity	NPD5222	Approved
0.7232	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5224	Approved
0.7217	Intermediate Similarity	NPD5211	Phase 2
0.7217	Intermediate Similarity	NPD5225	Approved
0.7217	Intermediate Similarity	NPD4633	Approved
0.7217	Intermediate Similarity	NPD5226	Approved
0.7213	Intermediate Similarity	NPD6274	Approved
0.7207	Intermediate Similarity	NPD7748	Approved
0.72	Intermediate Similarity	NPD8033	Approved
0.7196	Intermediate Similarity	NPD3618	Phase 1
0.7193	Intermediate Similarity	NPD4700	Approved
0.7182	Intermediate Similarity	NPD7515	Phase 2
0.7177	Intermediate Similarity	NPD7516	Approved
0.7168	Intermediate Similarity	NPD5173	Approved
0.7167	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6101	Approved
0.7155	Intermediate Similarity	NPD5174	Approved
0.7155	Intermediate Similarity	NPD5175	Approved
0.713	Intermediate Similarity	NPD5223	Approved
0.713	Intermediate Similarity	NPD3573	Approved
0.712	Intermediate Similarity	NPD8377	Approved
0.712	Intermediate Similarity	NPD8294	Approved
0.7105	Intermediate Similarity	NPD7638	Approved
0.7097	Intermediate Similarity	NPD7327	Approved
0.7097	Intermediate Similarity	NPD7328	Approved
0.7094	Intermediate Similarity	NPD5141	Approved
0.7083	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8380	Approved
0.7063	Intermediate Similarity	NPD8335	Approved
0.7063	Intermediate Similarity	NPD7503	Approved
0.7063	Intermediate Similarity	NPD8378	Approved
0.7063	Intermediate Similarity	NPD8379	Approved
0.7063	Intermediate Similarity	NPD8296	Approved
0.7054	Intermediate Similarity	NPD8074	Phase 3
0.7054	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7900	Approved
0.7043	Intermediate Similarity	NPD7639	Approved
0.7043	Intermediate Similarity	NPD7640	Approved
0.704	Intermediate Similarity	NPD7101	Approved
0.704	Intermediate Similarity	NPD7100	Approved
0.7027	Intermediate Similarity	NPD8035	Phase 2
0.7027	Intermediate Similarity	NPD8034	Phase 2
0.7018	Intermediate Similarity	NPD6083	Phase 2
0.7018	Intermediate Similarity	NPD6084	Phase 2
0.7016	Intermediate Similarity	NPD6317	Approved
0.7009	Intermediate Similarity	NPD4786	Approved
0.6991	Remote Similarity	NPD5695	Phase 3
0.6981	Remote Similarity	NPD3667	Approved
0.6964	Remote Similarity	NPD5778	Approved
0.6964	Remote Similarity	NPD5779	Approved
0.6964	Remote Similarity	NPD4202	Approved
0.696	Remote Similarity	NPD6314	Approved
0.696	Remote Similarity	NPD6335	Approved
0.696	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD5696	Approved
0.6942	Remote Similarity	NPD6371	Approved
0.6935	Remote Similarity	NPD6868	Approved
0.6929	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6921	Approved
0.6917	Remote Similarity	NPD5128	Approved
0.6917	Remote Similarity	NPD4730	Approved
0.6917	Remote Similarity	NPD4729	Approved
0.6891	Remote Similarity	NPD4767	Approved
0.6891	Remote Similarity	NPD4768	Approved
0.6881	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4754	Approved
0.6842	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6053	Discontinued
0.6822	Remote Similarity	NPD6067	Discontinued
0.6807	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5248	Approved
0.6803	Remote Similarity	NPD5247	Approved
0.6803	Remote Similarity	NPD5251	Approved
0.6803	Remote Similarity	NPD5249	Phase 3
0.6803	Remote Similarity	NPD5250	Approved
0.6797	Remote Similarity	NPD6908	Approved
0.6797	Remote Similarity	NPD6909	Approved
0.6789	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5956	Approved
0.6757	Remote Similarity	NPD6672	Approved
0.6757	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5737	Approved
0.6754	Remote Similarity	NPD5282	Discontinued
0.6748	Remote Similarity	NPD5216	Approved
0.6748	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5215	Approved
0.6748	Remote Similarity	NPD5217	Approved
0.6727	Remote Similarity	NPD6684	Approved
0.6727	Remote Similarity	NPD7334	Approved
0.6727	Remote Similarity	NPD6409	Approved
0.6727	Remote Similarity	NPD7521	Approved
0.6727	Remote Similarity	NPD5330	Approved
0.6727	Remote Similarity	NPD7146	Approved
0.6726	Remote Similarity	NPD7983	Approved
0.6726	Remote Similarity	NPD5284	Approved
0.6726	Remote Similarity	NPD5281	Approved
0.6716	Remote Similarity	NPD7260	Phase 2
0.6697	Remote Similarity	NPD3665	Phase 1
0.6697	Remote Similarity	NPD3666	Approved
0.6697	Remote Similarity	NPD3133	Approved
0.6696	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5210	Approved
0.6696	Remote Similarity	NPD4629	Approved
0.6696	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD6334	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6333	Approved
0.6639	Remote Similarity	NPD5168	Approved
0.6637	Remote Similarity	NPD6698	Approved
0.6637	Remote Similarity	NPD46	Approved
0.6617	Remote Similarity	NPD8337	Approved
0.6617	Remote Similarity	NPD8336	Approved
0.6613	Remote Similarity	NPD5127	Approved
0.6607	Remote Similarity	NPD6903	Approved
0.6579	Remote Similarity	NPD7637	Suspended
0.6577	Remote Similarity	NPD5279	Phase 3
0.6555	Remote Similarity	NPD5344	Discontinued
0.6545	Remote Similarity	NPD3668	Phase 3
0.6544	Remote Similarity	NPD8338	Approved
0.6512	Remote Similarity	NPD4522	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6486	Remote Similarity	NPD1694	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