NPASS Compound

Structure

NPC243354 OpenBabel07101718192D 29 33 0 0 1 0 0 0 0 0999 V2000 2.7048 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -3.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1236 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5123 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8102 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3118 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4896 -3.3002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8247 -0.3600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3369 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1668 0.3930 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 -0.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 0.3600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3557 -3.8002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5838 -1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3893 1.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1236 1.2261 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 1.4896 -2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 11 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 13 2 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 28 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 23 2 0 0 0 0 11 29 1 0 0 0 0 12 5 1 1 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 1 0 0 0 14 29 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 1 0 0 0 16 21 1 0 0 0 0 16 24 2 0 0 0 0 17 21 1 6 0 0 0 17 25 1 0 0 0 0 18 22 1 6 0 0 0 18 26 1 0 0 0 0 20 9 1 1 0 0 0 21 22 1 6 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	397.272
LogP:	1.89
LogD:	1.185
LogS:	-3.876
# Rotatable Bonds:	2
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	7.029
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.979
MDCK Permeability:	1.9924566004192457e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.408
Human Intestinal Absorption (HIA):	0.068
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.44

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.372
Plasma Protein Binding (PPB):	61.118675231933594%
Volume Distribution (VD):	0.934
Pgp-substrate:	52.776466369628906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.617
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	2.04
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.325
Rat Oral Acute Toxicity:	0.873
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.244
Carcinogencity:	0.866
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC243354

Natural Product ID:	NPC243354
*Common Name:**	Isoadenolin J
IUPAC Name:	n.a.
Synonyms:	isoadenolin J
Standard InCHIKey:	GSKRIVQTOXDITI-WNRVNUESSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-10-12-5-6-13-20-9-28-22(27,21(13,16(10)24)17(12)25)18(26)15(20)19(3,4)8-7-14(20)29-11(2)23/h6,12,14-15,17-18,25-27H,1,5,7-9H2,2-4H3/t12-,14-,15+,17+,18-,20+,21-,22+/m0/s1
SMILES:	CC(=O)O[C@H]1CCC([C@@H]2[C@]31CO[C@]([C@H]2O)([C@@]12C3=CC[C@H]([C@H]2O)C(=C)C1=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802165
PubChem CID:	56673380
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	>	10000.0	nM	PMID[479349]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[479349]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[479349]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[479349]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[479349]

☑ 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 NPC243354 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	255
0.1-0.2	1534
0.2-0.3	4686
0.3-0.4	8270
0.4-0.5	11993
0.5-0.6	6754
0.6-0.7	5031
0.7-0.8	3069
0.8-0.85	911
0.85-0.9	144
0.9-0.95	46
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9717	High Similarity	NPC194273
0.9714	High Similarity	NPC471243
0.9434	High Similarity	NPC471093
0.9352	High Similarity	NPC320118
0.9346	High Similarity	NPC213320
0.9346	High Similarity	NPC29505
0.934	High Similarity	NPC102741
0.9259	High Similarity	NPC473397
0.9259	High Similarity	NPC473352
0.9259	High Similarity	NPC474927
0.9245	High Similarity	NPC471094
0.9245	High Similarity	NPC55973
0.9245	High Similarity	NPC189663
0.9245	High Similarity	NPC89860
0.9245	High Similarity	NPC63841
0.9245	High Similarity	NPC473410
0.9245	High Similarity	NPC469984
0.9174	High Similarity	NPC471252
0.9174	High Similarity	NPC132668
0.9159	High Similarity	NPC252679
0.9159	High Similarity	NPC118721
0.9151	High Similarity	NPC186054
0.9151	High Similarity	NPC471461
0.9151	High Similarity	NPC67745
0.9151	High Similarity	NPC471474
0.9099	High Similarity	NPC218970
0.9099	High Similarity	NPC470171
0.9083	High Similarity	NPC205534
0.9074	High Similarity	NPC473324
0.9074	High Similarity	NPC85391
0.9074	High Similarity	NPC137104
0.9074	High Similarity	NPC320383
0.9074	High Similarity	NPC474786
0.9074	High Similarity	NPC471476
0.9057	High Similarity	NPC307660
0.9057	High Similarity	NPC56656
0.9057	High Similarity	NPC130511
0.9009	High Similarity	NPC88945
0.9009	High Similarity	NPC229752
0.8991	High Similarity	NPC201992
0.8991	High Similarity	NPC122339
0.8991	High Similarity	NPC63244
0.8981	High Similarity	NPC131903
0.8981	High Similarity	NPC274827
0.8962	High Similarity	NPC202793
0.8929	High Similarity	NPC78836
0.8929	High Similarity	NPC473304
0.8909	High Similarity	NPC289312
0.8909	High Similarity	NPC11252
0.8909	High Similarity	NPC471245
0.8909	High Similarity	NPC471244
0.8909	High Similarity	NPC473303
0.8868	High Similarity	NPC159442
0.8868	High Similarity	NPC139347
0.885	High Similarity	NPC188667
0.885	High Similarity	NPC297179
0.885	High Similarity	NPC204552
0.8829	High Similarity	NPC51978
0.8829	High Similarity	NPC471248
0.8829	High Similarity	NPC94141
0.8818	High Similarity	NPC56025
0.8807	High Similarity	NPC143706
0.8807	High Similarity	NPC472534
0.8803	High Similarity	NPC47113
0.8803	High Similarity	NPC174367
0.8785	High Similarity	NPC96268
0.8783	High Similarity	NPC477046
0.8783	High Similarity	NPC102822
0.8774	High Similarity	NPC475803
0.8774	High Similarity	NPC309388
0.8772	High Similarity	NPC469488
0.8761	High Similarity	NPC474654
0.8761	High Similarity	NPC287343
0.8761	High Similarity	NPC122033
0.8761	High Similarity	NPC470854
0.8761	High Similarity	NPC97908
0.875	High Similarity	NPC474906
0.875	High Similarity	NPC18547
0.875	High Similarity	NPC17165
0.8739	High Similarity	NPC157929
0.8739	High Similarity	NPC145625
0.8718	High Similarity	NPC473255
0.8716	High Similarity	NPC218123
0.8716	High Similarity	NPC273155
0.8716	High Similarity	NPC112895
0.8716	High Similarity	NPC293850
0.8716	High Similarity	NPC231278
0.8704	High Similarity	NPC102352
0.8696	High Similarity	NPC112038
0.8696	High Similarity	NPC476961
0.8692	High Similarity	NPC209298
0.8692	High Similarity	NPC277074
0.8684	High Similarity	NPC17772
0.8679	High Similarity	NPC14634
0.8673	High Similarity	NPC152199
0.8673	High Similarity	NPC235539
0.8673	High Similarity	NPC134869
0.8661	High Similarity	NPC194100
0.8661	High Similarity	NPC208998
0.8661	High Similarity	NPC255017
0.8661	High Similarity	NPC49451
0.8661	High Similarity	NPC7921
0.8649	High Similarity	NPC146945
0.8649	High Similarity	NPC329953
0.8649	High Similarity	NPC171888
0.8624	High Similarity	NPC166993
0.8624	High Similarity	NPC469746
0.8624	High Similarity	NPC3316
0.8624	High Similarity	NPC144854
0.8611	High Similarity	NPC474558
0.8609	High Similarity	NPC475775
0.8609	High Similarity	NPC476529
0.8609	High Similarity	NPC473203
0.8609	High Similarity	NPC470777
0.8596	High Similarity	NPC473968
0.8585	High Similarity	NPC470388
0.8584	High Similarity	NPC471398
0.8571	High Similarity	NPC287423
0.8571	High Similarity	NPC470882
0.8571	High Similarity	NPC302146
0.8559	High Similarity	NPC470922
0.8559	High Similarity	NPC474567
0.8547	High Similarity	NPC269642
0.8545	High Similarity	NPC469729
0.8545	High Similarity	NPC277017
0.8545	High Similarity	NPC154608
0.8545	High Similarity	NPC232133
0.8545	High Similarity	NPC192813
0.8545	High Similarity	NPC469733
0.8534	High Similarity	NPC109607
0.8534	High Similarity	NPC107338
0.8534	High Similarity	NPC471406
0.8532	High Similarity	NPC200957
0.8532	High Similarity	NPC12823
0.8532	High Similarity	NPC138908
0.8532	High Similarity	NPC4115
0.8522	High Similarity	NPC251310
0.8519	High Similarity	NPC122811
0.8519	High Similarity	NPC87927
0.8509	High Similarity	NPC328374
0.8509	High Similarity	NPC207217
0.8509	High Similarity	NPC40632
0.8509	High Similarity	NPC96312
0.8509	High Similarity	NPC251236
0.8505	High Similarity	NPC163963
0.8505	High Similarity	NPC471790
0.8505	High Similarity	NPC289148
0.8505	High Similarity	NPC52899
0.85	High Similarity	NPC311534
0.8491	Intermediate Similarity	NPC474793
0.8487	Intermediate Similarity	NPC293112
0.8482	Intermediate Similarity	NPC263827
0.8482	Intermediate Similarity	NPC285410
0.8482	Intermediate Similarity	NPC250481
0.8475	Intermediate Similarity	NPC11895
0.8475	Intermediate Similarity	NPC469789
0.8468	Intermediate Similarity	NPC469983
0.8468	Intermediate Similarity	NPC469744
0.8468	Intermediate Similarity	NPC218853
0.8462	Intermediate Similarity	NPC470921
0.8462	Intermediate Similarity	NPC202051
0.8455	Intermediate Similarity	NPC96333
0.8455	Intermediate Similarity	NPC230541
0.8455	Intermediate Similarity	NPC88833
0.8448	Intermediate Similarity	NPC475041
0.8448	Intermediate Similarity	NPC61520
0.8448	Intermediate Similarity	NPC319570
0.8443	Intermediate Similarity	NPC471855
0.844	Intermediate Similarity	NPC301787
0.844	Intermediate Similarity	NPC475036
0.844	Intermediate Similarity	NPC13149
0.8435	Intermediate Similarity	NPC476965
0.8435	Intermediate Similarity	NPC470775
0.8435	Intermediate Similarity	NPC470959
0.8435	Intermediate Similarity	NPC309433
0.8435	Intermediate Similarity	NPC176513
0.843	Intermediate Similarity	NPC476966
0.843	Intermediate Similarity	NPC231529
0.8426	Intermediate Similarity	NPC148628
0.8426	Intermediate Similarity	NPC286519
0.8426	Intermediate Similarity	NPC214946
0.8426	Intermediate Similarity	NPC88203
0.8426	Intermediate Similarity	NPC246736
0.8426	Intermediate Similarity	NPC304832
0.8426	Intermediate Similarity	NPC76866
0.8421	Intermediate Similarity	NPC469877
0.8421	Intermediate Similarity	NPC117712
0.8421	Intermediate Similarity	NPC473798
0.8421	Intermediate Similarity	NPC475633
0.8421	Intermediate Similarity	NPC470919
0.8417	Intermediate Similarity	NPC473265
0.8417	Intermediate Similarity	NPC305496
0.8417	Intermediate Similarity	NPC473253
0.8411	Intermediate Similarity	NPC287676
0.8407	Intermediate Similarity	NPC280782
0.8403	Intermediate Similarity	NPC248202
0.8403	Intermediate Similarity	NPC24651
0.8393	Intermediate Similarity	NPC197428
0.839	Intermediate Similarity	NPC28532
0.839	Intermediate Similarity	NPC170538

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 NPC243354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1799
0.2-0.3	3880
0.3-0.4	2100
0.4-0.5	618
0.5-0.6	279
0.6-0.7	140
0.7-0.8	105
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8376	Intermediate Similarity	NPD6319	Approved
0.825	Intermediate Similarity	NPD7492	Approved
0.822	Intermediate Similarity	NPD6054	Approved
0.8197	Intermediate Similarity	NPD7736	Approved
0.8182	Intermediate Similarity	NPD6616	Approved
0.8174	Intermediate Similarity	NPD4632	Approved
0.8167	Intermediate Similarity	NPD8328	Phase 3
0.8151	Intermediate Similarity	NPD6016	Approved
0.8151	Intermediate Similarity	NPD6015	Approved
0.8125	Intermediate Similarity	NPD6412	Phase 2
0.812	Intermediate Similarity	NPD6009	Approved
0.8115	Intermediate Similarity	NPD7078	Approved
0.8083	Intermediate Similarity	NPD5988	Approved
0.8083	Intermediate Similarity	NPD6370	Approved
0.8067	Intermediate Similarity	NPD6059	Approved
0.7984	Intermediate Similarity	NPD7319	Approved
0.7982	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8293	Discontinued
0.7966	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7115	Discovery
0.7965	Intermediate Similarity	NPD5697	Approved
0.7931	Intermediate Similarity	NPD6882	Approved
0.7931	Intermediate Similarity	NPD8297	Approved
0.7913	Intermediate Similarity	NPD4634	Approved
0.7895	Intermediate Similarity	NPD6881	Approved
0.7895	Intermediate Similarity	NPD6899	Approved
0.7886	Intermediate Similarity	NPD7507	Approved
0.7876	Intermediate Similarity	NPD7128	Approved
0.7876	Intermediate Similarity	NPD5739	Approved
0.7876	Intermediate Similarity	NPD6008	Approved
0.7876	Intermediate Similarity	NPD6675	Approved
0.7876	Intermediate Similarity	NPD6402	Approved
0.7845	Intermediate Similarity	NPD6649	Approved
0.7845	Intermediate Similarity	NPD6650	Approved
0.7826	Intermediate Similarity	NPD6012	Approved
0.7826	Intermediate Similarity	NPD6014	Approved
0.7826	Intermediate Similarity	NPD6372	Approved
0.7826	Intermediate Similarity	NPD6373	Approved
0.7826	Intermediate Similarity	NPD6013	Approved
0.7807	Intermediate Similarity	NPD5701	Approved
0.7759	Intermediate Similarity	NPD7290	Approved
0.7759	Intermediate Similarity	NPD6883	Approved
0.7759	Intermediate Similarity	NPD7102	Approved
0.7739	Intermediate Similarity	NPD7320	Approved
0.7739	Intermediate Similarity	NPD6011	Approved
0.7739	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD5983	Phase 2
0.7692	Intermediate Similarity	NPD6869	Approved
0.7692	Intermediate Similarity	NPD6617	Approved
0.7692	Intermediate Similarity	NPD8130	Phase 1
0.7692	Intermediate Similarity	NPD6847	Approved
0.7685	Intermediate Similarity	NPD6399	Phase 3
0.7589	Intermediate Similarity	NPD5286	Approved
0.7589	Intermediate Similarity	NPD5285	Approved
0.7589	Intermediate Similarity	NPD4696	Approved
0.7586	Intermediate Similarity	NPD6686	Approved
0.7581	Intermediate Similarity	NPD7604	Phase 2
0.7568	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD4225	Approved
0.748	Intermediate Similarity	NPD6033	Approved
0.746	Intermediate Similarity	NPD6336	Discontinued
0.7456	Intermediate Similarity	NPD5224	Approved
0.7456	Intermediate Similarity	NPD5211	Phase 2
0.7456	Intermediate Similarity	NPD5225	Approved
0.7456	Intermediate Similarity	NPD5226	Approved
0.7456	Intermediate Similarity	NPD4633	Approved
0.7438	Intermediate Similarity	NPD6274	Approved
0.7434	Intermediate Similarity	NPD4700	Approved
0.7431	Intermediate Similarity	NPD6079	Approved
0.7411	Intermediate Similarity	NPD7902	Approved
0.7407	Intermediate Similarity	NPD5328	Approved
0.7398	Intermediate Similarity	NPD7516	Approved
0.7395	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5175	Approved
0.7391	Intermediate Similarity	NPD5174	Approved
0.7373	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5223	Approved
0.7328	Intermediate Similarity	NPD5141	Approved
0.7321	Intermediate Similarity	NPD5222	Approved
0.7321	Intermediate Similarity	NPD5221	Approved
0.7321	Intermediate Similarity	NPD4697	Phase 3
0.7321	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7327	Approved
0.7317	Intermediate Similarity	NPD7328	Approved
0.7297	Intermediate Similarity	NPD7748	Approved
0.729	Intermediate Similarity	NPD3618	Phase 1
0.728	Intermediate Similarity	NPD8033	Approved
0.728	Intermediate Similarity	NPD8517	Approved
0.728	Intermediate Similarity	NPD8515	Approved
0.728	Intermediate Similarity	NPD8516	Approved
0.728	Intermediate Similarity	NPD8513	Phase 3
0.728	Intermediate Similarity	NPD7503	Approved
0.7273	Intermediate Similarity	NPD8133	Approved
0.7273	Intermediate Similarity	NPD7515	Phase 2
0.7273	Intermediate Similarity	NPD6411	Approved
0.7258	Intermediate Similarity	NPD7100	Approved
0.7258	Intermediate Similarity	NPD7101	Approved
0.7257	Intermediate Similarity	NPD6083	Phase 2
0.7257	Intermediate Similarity	NPD6084	Phase 2
0.7257	Intermediate Similarity	NPD5173	Approved
0.7236	Intermediate Similarity	NPD6317	Approved
0.7222	Intermediate Similarity	NPD3573	Approved
0.7207	Intermediate Similarity	NPD4202	Approved
0.72	Intermediate Similarity	NPD8294	Approved
0.72	Intermediate Similarity	NPD8377	Approved
0.7193	Intermediate Similarity	NPD7638	Approved
0.7193	Intermediate Similarity	NPD5696	Approved
0.7177	Intermediate Similarity	NPD6314	Approved
0.7177	Intermediate Similarity	NPD6335	Approved
0.7177	Intermediate Similarity	NPD6313	Approved
0.7167	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8380	Approved
0.7143	Intermediate Similarity	NPD8335	Approved
0.7143	Intermediate Similarity	NPD5128	Approved
0.7143	Intermediate Similarity	NPD7900	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD8379	Approved
0.7143	Intermediate Similarity	NPD8296	Approved
0.7143	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4729	Approved
0.7143	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8378	Approved
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7639	Approved
0.7119	Intermediate Similarity	NPD4768	Approved
0.7119	Intermediate Similarity	NPD4767	Approved
0.7117	Intermediate Similarity	NPD8035	Phase 2
0.7117	Intermediate Similarity	NPD8034	Phase 2
0.7103	Intermediate Similarity	NPD4786	Approved
0.7094	Intermediate Similarity	NPD4754	Approved
0.7091	Intermediate Similarity	NPD6101	Approved
0.7091	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5695	Phase 3
0.7075	Intermediate Similarity	NPD3667	Approved
0.7031	Intermediate Similarity	NPD6067	Discontinued
0.7025	Intermediate Similarity	NPD5251	Approved
0.7025	Intermediate Similarity	NPD6371	Approved
0.7025	Intermediate Similarity	NPD5250	Approved
0.7025	Intermediate Similarity	NPD5249	Phase 3
0.7025	Intermediate Similarity	NPD5248	Approved
0.7025	Intermediate Similarity	NPD5247	Approved
0.7016	Intermediate Similarity	NPD6868	Approved
0.7008	Intermediate Similarity	NPD6908	Approved
0.7008	Intermediate Similarity	NPD6909	Approved
0.7008	Intermediate Similarity	NPD6921	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6684	Approved
0.6972	Remote Similarity	NPD7334	Approved
0.6972	Remote Similarity	NPD7521	Approved
0.6972	Remote Similarity	NPD6409	Approved
0.6972	Remote Similarity	NPD7146	Approved
0.6972	Remote Similarity	NPD5330	Approved
0.697	Remote Similarity	NPD5956	Approved
0.6967	Remote Similarity	NPD5215	Approved
0.6967	Remote Similarity	NPD5217	Approved
0.6967	Remote Similarity	NPD5216	Approved
0.6944	Remote Similarity	NPD3666	Approved
0.6944	Remote Similarity	NPD3133	Approved
0.6944	Remote Similarity	NPD3665	Phase 1
0.6937	Remote Similarity	NPD4753	Phase 2
0.693	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4629	Approved
0.693	Remote Similarity	NPD5210	Approved
0.6917	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6053	Discontinued
0.6903	Remote Similarity	NPD5779	Approved
0.6903	Remote Similarity	NPD5778	Approved
0.6891	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5135	Approved
0.6885	Remote Similarity	NPD5169	Approved
0.6885	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8074	Phase 3
0.6861	Remote Similarity	NPD6334	Approved
0.6861	Remote Similarity	NPD6333	Approved
0.6847	Remote Similarity	NPD5737	Approved
0.6847	Remote Similarity	NPD6903	Approved
0.6847	Remote Similarity	NPD6672	Approved
0.6829	Remote Similarity	NPD5127	Approved
0.6814	Remote Similarity	NPD5284	Approved
0.6814	Remote Similarity	NPD5281	Approved
0.6783	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5168	Approved
0.6719	Remote Similarity	NPD4522	Approved
0.6696	Remote Similarity	NPD5282	Discontinued
0.6696	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6637	Remote Similarity	NPD6080	Approved
0.6637	Remote Similarity	NPD6904	Approved
0.6637	Remote Similarity	NPD6673	Approved
0.6636	Remote Similarity	NPD3668	Phase 3
0.6606	Remote Similarity	NPD4223	Phase 3
0.6606	Remote Similarity	NPD4221	Approved
0.6583	Remote Similarity	NPD7632	Discontinued
0.6579	Remote Similarity	NPD46	Approved
0.6579	Remote Similarity	NPD6698	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