NPASS Compound

Structure

NPC122339 OpenBabel07101718222D 28 32 0 0 1 0 0 0 0 0999 V2000 2.6091 -2.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5661 -1.0419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0838 -0.2065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6707 -2.6238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4233 -0.9731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7461 -1.1277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6015 -1.7365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2299 -1.1753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7247 -0.3473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2031 -0.6946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6015 -1.7365 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.6946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2895 -0.9607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0900 0.3791 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.6946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6015 -1.0419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6015 -1.0419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2031 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6015 0.3473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4369 -2.2188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5631 -1.5953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3047 1.3195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8354 0.4823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0838 1.1827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6707 -1.6592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 5 1 1 0 0 0 10 15 1 0 0 0 0 11 19 1 1 0 0 0 11 20 1 0 0 0 0 12 19 1 1 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 1 0 0 0 14 20 1 0 0 0 0 14 23 2 0 0 0 0 15 20 1 6 0 0 0 15 24 1 0 0 0 0 16 21 1 6 0 0 0 16 25 1 0 0 0 0 17 19 1 1 0 0 0 17 27 1 0 0 0 0 17 28 1 0 0 0 0 20 21 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.2
Volume:	385.249
LogP:	1.374
LogD:	0.956
LogS:	-4.266
# Rotatable Bonds:	1
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	7.014
Fsp3:	0.857
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:	-5.013
MDCK Permeability:	9.60098986979574e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.142
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.266

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.193
Plasma Protein Binding (PPB):	52.19966125488281%
Volume Distribution (VD):	0.861
Pgp-substrate:	61.6633415222168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.636
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	2.877
Half-life (T1/2):	0.307

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.659
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.478
Carcinogencity:	0.531
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC122339

Natural Product ID:	NPC122339
*Common Name:**	UHERRNNNKBWWKU-BBTAMKDRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UHERRNNNKBWWKU-BBTAMKDRSA-N
Standard InCHI:	InChI=1S/C21H30O7/c1-9-10-5-6-11-19-12(22)7-8-18(2,3)13(19)16(25)21(26,28-17(19)27-4)20(11,14(9)23)15(10)24/h10-13,15-17,22,24-26H,1,5-8H2,2-4H3/t10-,11-,12-,13+,15+,16-,17-,19-,20-,21+/m0/s1
SMILES:	CO[C@H]1O[C@]2(O)[C@H]([C@H]3[C@@]1([C@@H](O)CCC3(C)C)[C@H]1[C@@]32[C@H](O)[C@@H](CC1)C(=C)C3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2407389
PubChem CID:	73356653
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[23819871]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000.0	nM	PMID[535781]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	9400.0	nM	PMID[535781]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[535781]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[535781]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[535781]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	7000.0	nM	PMID[535781]

☑ 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 NPC122339 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	298
0.1-0.2	2104
0.2-0.3	6225
0.3-0.4	10493
0.4-0.5	10591
0.5-0.6	6280
0.6-0.7	3792
0.7-0.8	2155
0.8-0.85	625
0.85-0.9	60
0.9-0.95	38
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC473303
0.9903	High Similarity	NPC471245
0.9902	High Similarity	NPC473324
0.9806	High Similarity	NPC63244
0.9712	High Similarity	NPC145625
0.9712	High Similarity	NPC471244
0.9709	High Similarity	NPC471476
0.9706	High Similarity	NPC55973
0.9619	High Similarity	NPC94141
0.9608	High Similarity	NPC471461
0.9608	High Similarity	NPC67745
0.9533	High Similarity	NPC473304
0.9528	High Similarity	NPC17165
0.9524	High Similarity	NPC157929
0.9519	High Similarity	NPC471093
0.9515	High Similarity	NPC189663
0.9515	High Similarity	NPC469729
0.9515	High Similarity	NPC89860
0.9515	High Similarity	NPC469733
0.951	High Similarity	NPC12823
0.9439	High Similarity	NPC88945
0.9439	High Similarity	NPC229752
0.9434	High Similarity	NPC471248
0.9434	High Similarity	NPC132668
0.9429	High Similarity	NPC29505
0.9423	High Similarity	NPC252679
0.9423	High Similarity	NPC118721
0.9352	High Similarity	NPC78836
0.9327	High Similarity	NPC63841
0.932	High Similarity	NPC307660
0.932	High Similarity	NPC130511
0.9252	High Similarity	NPC471252
0.9245	High Similarity	NPC213320
0.9245	High Similarity	NPC329953
0.9238	High Similarity	NPC469744
0.9238	High Similarity	NPC102741
0.9231	High Similarity	NPC469746
0.9231	High Similarity	NPC186054
0.9216	High Similarity	NPC475803
0.9216	High Similarity	NPC309388
0.9159	High Similarity	NPC473352
0.9159	High Similarity	NPC474927
0.9159	High Similarity	NPC473397
0.9143	High Similarity	NPC471094
0.9143	High Similarity	NPC469984
0.9143	High Similarity	NPC473410
0.9135	High Similarity	NPC4115
0.9065	High Similarity	NPC471243
0.9048	High Similarity	NPC471474
0.8991	High Similarity	NPC243354
0.8972	High Similarity	NPC85391
0.8972	High Similarity	NPC320383
0.8972	High Similarity	NPC474786
0.8972	High Similarity	NPC137104
0.8952	High Similarity	NPC56656
0.8942	High Similarity	NPC139347
0.8932	High Similarity	NPC14634
0.8879	High Similarity	NPC274827
0.8879	High Similarity	NPC131903
0.8879	High Similarity	NPC8431
0.8857	High Similarity	NPC13149
0.8857	High Similarity	NPC202793
0.8807	High Similarity	NPC472719
0.8807	High Similarity	NPC207845
0.8785	High Similarity	NPC231278
0.8785	High Similarity	NPC232133
0.8785	High Similarity	NPC218123
0.8785	High Similarity	NPC273155
0.8785	High Similarity	NPC112895
0.8762	High Similarity	NPC209298
0.8762	High Similarity	NPC277074
0.875	High Similarity	NPC471790
0.8727	High Similarity	NPC73986
0.8727	High Similarity	NPC194273
0.8716	High Similarity	NPC56025
0.8716	High Similarity	NPC274833
0.8704	High Similarity	NPC469983
0.8692	High Similarity	NPC88833
0.8692	High Similarity	NPC166993
0.8692	High Similarity	NPC96333
0.8654	High Similarity	NPC291785
0.8654	High Similarity	NPC470388
0.8654	High Similarity	NPC127408
0.8624	High Similarity	NPC98069
0.8624	High Similarity	NPC49730
0.8598	High Similarity	NPC103172
0.8598	High Similarity	NPC138908
0.8598	High Similarity	NPC200957
0.8598	High Similarity	NPC164600
0.8585	High Similarity	NPC87927
0.8585	High Similarity	NPC107385
0.8585	High Similarity	NPC122811
0.8571	High Similarity	NPC52899
0.8571	High Similarity	NPC289148
0.8571	High Similarity	NPC163963
0.8571	High Similarity	NPC472718
0.8519	High Similarity	NPC61071
0.8505	High Similarity	NPC101842
0.8505	High Similarity	NPC301787
0.8505	High Similarity	NPC474558
0.8496	Intermediate Similarity	NPC218970
0.8491	Intermediate Similarity	NPC304832
0.8491	Intermediate Similarity	NPC76866
0.8491	Intermediate Similarity	NPC214946
0.8491	Intermediate Similarity	NPC88203
0.8491	Intermediate Similarity	NPC148628
0.8491	Intermediate Similarity	NPC286519
0.8491	Intermediate Similarity	NPC246736
0.8476	Intermediate Similarity	NPC287676
0.8468	Intermediate Similarity	NPC243572
0.8468	Intermediate Similarity	NPC205534
0.8447	Intermediate Similarity	NPC41070
0.8447	Intermediate Similarity	NPC84018
0.8447	Intermediate Similarity	NPC231060
0.8447	Intermediate Similarity	NPC138245
0.8431	Intermediate Similarity	NPC144739
0.8431	Intermediate Similarity	NPC181594
0.8426	Intermediate Similarity	NPC222833
0.8411	Intermediate Similarity	NPC216114
0.8396	Intermediate Similarity	NPC252614
0.8396	Intermediate Similarity	NPC46848
0.8393	Intermediate Similarity	NPC320118
0.8393	Intermediate Similarity	NPC102619
0.839	Intermediate Similarity	NPC47113
0.839	Intermediate Similarity	NPC174367
0.8381	Intermediate Similarity	NPC78427
0.8381	Intermediate Similarity	NPC16911
0.8381	Intermediate Similarity	NPC474793
0.8381	Intermediate Similarity	NPC471038
0.8378	Intermediate Similarity	NPC11035
0.8378	Intermediate Similarity	NPC272242
0.8365	Intermediate Similarity	NPC13949
0.8364	Intermediate Similarity	NPC91583
0.8364	Intermediate Similarity	NPC240125
0.835	Intermediate Similarity	NPC215271
0.835	Intermediate Similarity	NPC302008
0.835	Intermediate Similarity	NPC289539
0.835	Intermediate Similarity	NPC153775
0.835	Intermediate Similarity	NPC111524
0.835	Intermediate Similarity	NPC191094
0.835	Intermediate Similarity	NPC101233
0.835	Intermediate Similarity	NPC261333
0.835	Intermediate Similarity	NPC91772
0.835	Intermediate Similarity	NPC292374
0.835	Intermediate Similarity	NPC129004
0.835	Intermediate Similarity	NPC104371
0.835	Intermediate Similarity	NPC29247
0.8333	Intermediate Similarity	NPC299185
0.8333	Intermediate Similarity	NPC476168
0.8333	Intermediate Similarity	NPC98603
0.8333	Intermediate Similarity	NPC84928
0.8333	Intermediate Similarity	NPC470167
0.8319	Intermediate Similarity	NPC102088
0.8319	Intermediate Similarity	NPC477580
0.8318	Intermediate Similarity	NPC275990
0.8304	Intermediate Similarity	NPC470543
0.8291	Intermediate Similarity	NPC28532
0.8288	Intermediate Similarity	NPC98633
0.8288	Intermediate Similarity	NPC130302
0.8276	Intermediate Similarity	NPC281840
0.8273	Intermediate Similarity	NPC230888
0.8273	Intermediate Similarity	NPC88744
0.8269	Intermediate Similarity	NPC470232
0.8261	Intermediate Similarity	NPC239293
0.8257	Intermediate Similarity	NPC285927
0.8252	Intermediate Similarity	NPC59170
0.8241	Intermediate Similarity	NPC96217
0.8235	Intermediate Similarity	NPC273962
0.8235	Intermediate Similarity	NPC149761
0.8235	Intermediate Similarity	NPC470378
0.8235	Intermediate Similarity	NPC180849
0.8235	Intermediate Similarity	NPC80401
0.8235	Intermediate Similarity	NPC261994
0.823	Intermediate Similarity	NPC293038
0.823	Intermediate Similarity	NPC62696
0.823	Intermediate Similarity	NPC260665
0.823	Intermediate Similarity	NPC146563
0.8224	Intermediate Similarity	NPC236585
0.8224	Intermediate Similarity	NPC148279
0.8214	Intermediate Similarity	NPC471251
0.8214	Intermediate Similarity	NPC94650
0.8208	Intermediate Similarity	NPC89099
0.8208	Intermediate Similarity	NPC38296
0.8208	Intermediate Similarity	NPC38471
0.8208	Intermediate Similarity	NPC162459
0.8208	Intermediate Similarity	NPC98837
0.8208	Intermediate Similarity	NPC20479
0.8208	Intermediate Similarity	NPC28864
0.8205	Intermediate Similarity	NPC470478
0.8198	Intermediate Similarity	NPC471250
0.8198	Intermediate Similarity	NPC246205
0.8198	Intermediate Similarity	NPC473844
0.8198	Intermediate Similarity	NPC51947
0.819	Intermediate Similarity	NPC256227
0.819	Intermediate Similarity	NPC135548
0.819	Intermediate Similarity	NPC140242
0.819	Intermediate Similarity	NPC104568
0.819	Intermediate Similarity	NPC329910
0.819	Intermediate Similarity	NPC200054
0.819	Intermediate Similarity	NPC264979

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 NPC122339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	2455
0.2-0.3	4022
0.3-0.4	1496
0.4-0.5	450
0.5-0.6	252
0.6-0.7	135
0.7-0.8	36
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8018	Intermediate Similarity	NPD6412	Phase 2
0.7983	Intermediate Similarity	NPD6370	Approved
0.7951	Intermediate Similarity	NPD7736	Approved
0.7917	Intermediate Similarity	NPD8328	Phase 3
0.7886	Intermediate Similarity	NPD7319	Approved
0.7863	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6054	Approved
0.7787	Intermediate Similarity	NPD7507	Approved
0.7759	Intermediate Similarity	NPD8133	Approved
0.775	Intermediate Similarity	NPD6016	Approved
0.775	Intermediate Similarity	NPD6015	Approved
0.7719	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD5988	Approved
0.7679	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6059	Approved
0.7581	Intermediate Similarity	NPD8293	Discontinued
0.7561	Intermediate Similarity	NPD7492	Approved
0.7521	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6616	Approved
0.7478	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7078	Approved
0.7417	Intermediate Similarity	NPD6009	Approved
0.735	Intermediate Similarity	NPD4634	Approved
0.7328	Intermediate Similarity	NPD6686	Approved
0.7311	Intermediate Similarity	NPD4632	Approved
0.7295	Intermediate Similarity	NPD7516	Approved
0.7227	Intermediate Similarity	NPD6882	Approved
0.7213	Intermediate Similarity	NPD7327	Approved
0.7213	Intermediate Similarity	NPD7328	Approved
0.7177	Intermediate Similarity	NPD8033	Approved
0.7156	Intermediate Similarity	NPD8034	Phase 2
0.7156	Intermediate Similarity	NPD8035	Phase 2
0.7131	Intermediate Similarity	NPD7115	Discovery
0.7109	Intermediate Similarity	NPD6033	Approved
0.7097	Intermediate Similarity	NPD8294	Approved
0.7097	Intermediate Similarity	NPD8377	Approved
0.7094	Intermediate Similarity	NPD5697	Approved
0.7083	Intermediate Similarity	NPD8297	Approved
0.704	Intermediate Similarity	NPD8296	Approved
0.704	Intermediate Similarity	NPD8335	Approved
0.704	Intermediate Similarity	NPD8380	Approved
0.704	Intermediate Similarity	NPD8378	Approved
0.704	Intermediate Similarity	NPD8379	Approved
0.7034	Intermediate Similarity	NPD6881	Approved
0.7034	Intermediate Similarity	NPD6899	Approved
0.7018	Intermediate Similarity	NPD5286	Approved
0.7018	Intermediate Similarity	NPD4696	Approved
0.7018	Intermediate Similarity	NPD5285	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD6008	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6649	Approved
0.6991	Remote Similarity	NPD4755	Approved
0.6975	Remote Similarity	NPD6373	Approved
0.6975	Remote Similarity	NPD6372	Approved
0.6975	Remote Similarity	NPD6014	Approved
0.6975	Remote Similarity	NPD6012	Approved
0.6975	Remote Similarity	NPD6013	Approved
0.6949	Remote Similarity	NPD5701	Approved
0.6929	Remote Similarity	NPD6067	Discontinued
0.6917	Remote Similarity	NPD6883	Approved
0.6917	Remote Similarity	NPD7290	Approved
0.6917	Remote Similarity	NPD7102	Approved
0.6916	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5983	Phase 2
0.6905	Remote Similarity	NPD7503	Approved
0.6905	Remote Similarity	NPD8513	Phase 3
0.6905	Remote Similarity	NPD8516	Approved
0.6905	Remote Similarity	NPD8517	Approved
0.6905	Remote Similarity	NPD8515	Approved
0.6897	Remote Similarity	NPD5226	Approved
0.6897	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD5225	Approved
0.6897	Remote Similarity	NPD4633	Approved
0.6897	Remote Similarity	NPD5224	Approved
0.6891	Remote Similarity	NPD7320	Approved
0.6891	Remote Similarity	NPD6011	Approved
0.687	Remote Similarity	NPD4700	Approved
0.686	Remote Similarity	NPD6617	Approved
0.686	Remote Similarity	NPD6847	Approved
0.686	Remote Similarity	NPD6869	Approved
0.686	Remote Similarity	NPD8130	Phase 1
0.6847	Remote Similarity	NPD6079	Approved
0.6838	Remote Similarity	NPD5175	Approved
0.6838	Remote Similarity	NPD5174	Approved
0.6818	Remote Similarity	NPD5328	Approved
0.681	Remote Similarity	NPD5223	Approved
0.6797	Remote Similarity	NPD7604	Phase 2
0.6786	Remote Similarity	NPD8171	Discontinued
0.6786	Remote Similarity	NPD6399	Phase 3
0.6783	Remote Similarity	NPD4225	Approved
0.678	Remote Similarity	NPD5141	Approved
0.6772	Remote Similarity	NPD6921	Approved
0.6754	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5221	Approved
0.6754	Remote Similarity	NPD5222	Approved
0.6754	Remote Similarity	NPD4697	Phase 3
0.6729	Remote Similarity	NPD4788	Approved
0.6697	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD5173	Approved
0.6696	Remote Similarity	NPD7902	Approved
0.6694	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6336	Discontinued
0.664	Remote Similarity	NPD6274	Approved
0.6638	Remote Similarity	NPD7638	Approved
0.6637	Remote Similarity	NPD4202	Approved
0.6617	Remote Similarity	NPD5956	Approved
0.6612	Remote Similarity	NPD4730	Approved
0.6612	Remote Similarity	NPD4729	Approved
0.6612	Remote Similarity	NPD5128	Approved
0.6602	Remote Similarity	NPD3703	Phase 2
0.6585	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4767	Approved
0.6583	Remote Similarity	NPD4768	Approved
0.6581	Remote Similarity	NPD7639	Approved
0.6581	Remote Similarity	NPD7640	Approved
0.6579	Remote Similarity	NPD7748	Approved
0.6555	Remote Similarity	NPD4754	Approved
0.6549	Remote Similarity	NPD7515	Phase 2
0.6545	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4786	Approved
0.6508	Remote Similarity	NPD6940	Discontinued
0.6504	Remote Similarity	NPD5248	Approved
0.6504	Remote Similarity	NPD5250	Approved
0.6504	Remote Similarity	NPD5249	Phase 3
0.6504	Remote Similarity	NPD5251	Approved
0.6504	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5247	Approved
0.6484	Remote Similarity	NPD7101	Approved
0.6484	Remote Similarity	NPD7100	Approved
0.6481	Remote Similarity	NPD3667	Approved
0.6457	Remote Similarity	NPD6317	Approved
0.6452	Remote Similarity	NPD5216	Approved
0.6452	Remote Similarity	NPD5215	Approved
0.6452	Remote Similarity	NPD5217	Approved
0.6449	Remote Similarity	NPD6928	Phase 2
0.6435	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7900	Approved
0.6415	Remote Similarity	NPD6115	Approved
0.6415	Remote Similarity	NPD6118	Approved
0.6415	Remote Similarity	NPD6114	Approved
0.6415	Remote Similarity	NPD6697	Approved
0.641	Remote Similarity	NPD6084	Phase 2
0.641	Remote Similarity	NPD6083	Phase 2
0.6406	Remote Similarity	NPD6313	Approved
0.6406	Remote Similarity	NPD6314	Approved
0.6406	Remote Similarity	NPD6335	Approved
0.6404	Remote Similarity	NPD6411	Approved
0.6387	Remote Similarity	NPD1700	Approved
0.6385	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4629	Approved
0.6379	Remote Similarity	NPD5210	Approved
0.6372	Remote Similarity	NPD4753	Phase 2
0.6371	Remote Similarity	NPD5169	Approved
0.6371	Remote Similarity	NPD6371	Approved
0.6371	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5135	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6356	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD3573	Approved
0.6321	Remote Similarity	NPD6116	Phase 1
0.632	Remote Similarity	NPD5127	Approved
0.6293	Remote Similarity	NPD5282	Discontinued
0.6283	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD8074	Phase 3
0.626	Remote Similarity	NPD6908	Approved
0.626	Remote Similarity	NPD6909	Approved
0.626	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD5695	Phase 3
0.6239	Remote Similarity	NPD1780	Approved
0.6239	Remote Similarity	NPD1779	Approved
0.6231	Remote Similarity	NPD4522	Approved
0.6228	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6101	Approved
0.6226	Remote Similarity	NPD6117	Approved
0.621	Remote Similarity	NPD5168	Approved
0.6198	Remote Similarity	NPD7632	Discontinued
0.6172	Remote Similarity	NPD5167	Approved
0.617	Remote Similarity	NPD6334	Approved
0.617	Remote Similarity	NPD6333	Approved
0.6159	Remote Similarity	NPD8338	Approved
0.6154	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7525	Registered
0.6142	Remote Similarity	NPD6053	Discontinued
0.6126	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD3669	Approved
0.6117	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7146	Approved
0.6106	Remote Similarity	NPD6409	Approved
0.6106	Remote Similarity	NPD7521	Approved
0.6106	Remote Similarity	NPD6684	Approved
0.6106	Remote Similarity	NPD7334	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