NPASS Compound

Structure

NPC475023 OpenBabel07101719522D 26 28 0 0 1 0 0 0 0 0999 V2000 1.4049 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7788 -0.7399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7788 -4.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 -5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -1.6910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9049 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -3.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9049 -5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.0388 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.0388 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4049 -6.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9049 -6.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4049 -6.0981 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 24 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 22 24 1 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 M CHG 1 26 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	351.23
Volume:	398.434
LogP:	4.072
LogD:	4.283
LogS:	-4.926
# Rotatable Bonds:	4
TPSA:	40.13
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.581
Synthetic Accessibility Score:	4.746
Fsp3:	0.542
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	3.741853288374841e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.469

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.29546356201172%
Volume Distribution (VD):	0.92
Pgp-substrate:	2.7909061908721924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.284
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.486
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.331
CYP2D6-inhibitor:	0.1
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.861
CYP3A4-substrate:	0.562

ADMET: Excretion

Clearance (CL):	1.933
Half-life (T1/2):	0.548

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.841
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.034
Carcinogencity:	0.009
Eye Corrosion:	0.011
Eye Irritation:	0.357
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC475023

Natural Product ID:	NPC475023
*Common Name:**	Plakotenin Sodium Salt
IUPAC Name:	sodium;(E)-3-[(1R,3R,3aR,4S,5S,7aR)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoate
Synonyms:	Plakotenin Sodium Salt
Standard InCHIKey:	IJHAJSPVOFHBHD-YYLAWESZSA-M
Standard InCHI:	InChI=1S/C24H32O2.Na/c1-6-24(14-18(5)23(25)26)20(19-10-8-7-9-11-19)13-16(3)21-15(2)12-17(4)22(21)24;/h7-11,13-15,17,20-22H,6,12H2,1-5H3,(H,25,26);/q;+1/p-1/b18-14+;/t15-,17-,20+,21+,22-,24+;/m1./s1
SMILES:	CC[C@]1(/C=C(/C(=O)[O-])C)[C@@H](C=C([C@H]2[C@H]1[C@H](C)C[C@H]2C)C)c1ccccc1.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492405
PubChem CID:	21775549
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[10479343]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11277756]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722494]
NPO4331	Plakortis lita	Species	Plakinidae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	35.7	%	PMID[528150]

☑ 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 NPC475023 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	202
0.1-0.2	1565
0.2-0.3	3158
0.3-0.4	15134
0.4-0.5	17681
0.5-0.6	4197
0.6-0.7	710
0.7-0.8	45
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475059
0.9884	High Similarity	NPC475057
0.9444	High Similarity	NPC251579
0.9444	High Similarity	NPC133135
0.837	Intermediate Similarity	NPC26224
0.8144	Intermediate Similarity	NPC120393
0.8125	Intermediate Similarity	NPC469893
0.8041	Intermediate Similarity	NPC469890
0.8041	Intermediate Similarity	NPC469892
0.8041	Intermediate Similarity	NPC469891
0.798	Intermediate Similarity	NPC264728
0.7767	Intermediate Similarity	NPC244933
0.7767	Intermediate Similarity	NPC85560
0.7717	Intermediate Similarity	NPC267704
0.7677	Intermediate Similarity	NPC239185
0.7664	Intermediate Similarity	NPC306977
0.7664	Intermediate Similarity	NPC206414
0.7664	Intermediate Similarity	NPC242957
0.7664	Intermediate Similarity	NPC287055
0.764	Intermediate Similarity	NPC50192
0.7629	Intermediate Similarity	NPC1682
0.7629	Intermediate Similarity	NPC59677
0.7629	Intermediate Similarity	NPC188844
0.7629	Intermediate Similarity	NPC153885
0.76	Intermediate Similarity	NPC75724
0.76	Intermediate Similarity	NPC134882
0.7596	Intermediate Similarity	NPC472700
0.7596	Intermediate Similarity	NPC472699
0.7582	Intermediate Similarity	NPC303245
0.7551	Intermediate Similarity	NPC238219
0.7528	Intermediate Similarity	NPC3672
0.7528	Intermediate Similarity	NPC287790
0.7526	Intermediate Similarity	NPC284475
0.7526	Intermediate Similarity	NPC133461
0.7524	Intermediate Similarity	NPC472701
0.7524	Intermediate Similarity	NPC472683
0.7524	Intermediate Similarity	NPC472695
0.7524	Intermediate Similarity	NPC472696
0.75	Intermediate Similarity	NPC32203
0.75	Intermediate Similarity	NPC206800
0.75	Intermediate Similarity	NPC265220
0.75	Intermediate Similarity	NPC226041
0.7475	Intermediate Similarity	NPC260233
0.7451	Intermediate Similarity	NPC109514
0.7451	Intermediate Similarity	NPC476993
0.7449	Intermediate Similarity	NPC323420
0.7449	Intermediate Similarity	NPC155232
0.7447	Intermediate Similarity	NPC53299
0.7419	Intermediate Similarity	NPC208183
0.7419	Intermediate Similarity	NPC243289
0.7404	Intermediate Similarity	NPC472221
0.7404	Intermediate Similarity	NPC329282
0.7404	Intermediate Similarity	NPC472222
0.74	Intermediate Similarity	NPC219573
0.74	Intermediate Similarity	NPC185208
0.7396	Intermediate Similarity	NPC157778
0.7363	Intermediate Similarity	NPC167577
0.7363	Intermediate Similarity	NPC78517
0.7358	Intermediate Similarity	NPC249811
0.7353	Intermediate Similarity	NPC7435
0.7353	Intermediate Similarity	NPC221825
0.732	Intermediate Similarity	NPC298115
0.7292	Intermediate Similarity	NPC43945
0.7283	Intermediate Similarity	NPC17408
0.7283	Intermediate Similarity	NPC285716
0.7282	Intermediate Similarity	NPC133809
0.7282	Intermediate Similarity	NPC136810
0.7282	Intermediate Similarity	NPC128248
0.7282	Intermediate Similarity	NPC225079
0.7255	Intermediate Similarity	NPC49994
0.7253	Intermediate Similarity	NPC176228
0.7245	Intermediate Similarity	NPC58872
0.7245	Intermediate Similarity	NPC173413
0.7241	Intermediate Similarity	NPC95289
0.7232	Intermediate Similarity	NPC471936
0.7204	Intermediate Similarity	NPC89950
0.7204	Intermediate Similarity	NPC71795
0.7204	Intermediate Similarity	NPC242628
0.7172	Intermediate Similarity	NPC125226
0.7168	Intermediate Similarity	NPC152812
0.7143	Intermediate Similarity	NPC472691
0.7143	Intermediate Similarity	NPC471829
0.7143	Intermediate Similarity	NPC3190
0.7143	Intermediate Similarity	NPC179726
0.7143	Intermediate Similarity	NPC475939
0.7143	Intermediate Similarity	NPC249018
0.7143	Intermediate Similarity	NPC113307
0.7143	Intermediate Similarity	NPC474866
0.713	Intermediate Similarity	NPC470585
0.7128	Intermediate Similarity	NPC99240
0.7128	Intermediate Similarity	NPC230068
0.7126	Intermediate Similarity	NPC98880
0.7115	Intermediate Similarity	NPC472879
0.7113	Intermediate Similarity	NPC69057
0.7103	Intermediate Similarity	NPC37914
0.71	Intermediate Similarity	NPC77273
0.7091	Intermediate Similarity	NPC280789
0.7087	Intermediate Similarity	NPC179411
0.708	Intermediate Similarity	NPC470820
0.7079	Intermediate Similarity	NPC54269
0.7071	Intermediate Similarity	NPC303967
0.7071	Intermediate Similarity	NPC213156
0.7071	Intermediate Similarity	NPC240108
0.7071	Intermediate Similarity	NPC67585
0.7071	Intermediate Similarity	NPC110420
0.7065	Intermediate Similarity	NPC103488
0.7053	Intermediate Similarity	NPC127491
0.7053	Intermediate Similarity	NPC308619
0.7053	Intermediate Similarity	NPC324835
0.7043	Intermediate Similarity	NPC470814
0.7033	Intermediate Similarity	NPC175393
0.7027	Intermediate Similarity	NPC93287
0.7018	Intermediate Similarity	NPC84129
0.7011	Intermediate Similarity	NPC311343
0.701	Intermediate Similarity	NPC160339
0.701	Intermediate Similarity	NPC307
0.7	Intermediate Similarity	NPC95126
0.7	Intermediate Similarity	NPC475002
0.7	Intermediate Similarity	NPC86987
0.7	Intermediate Similarity	NPC133308
0.6991	Remote Similarity	NPC9274
0.6991	Remote Similarity	NPC476476
0.6989	Remote Similarity	NPC139901
0.6989	Remote Similarity	NPC159661
0.6989	Remote Similarity	NPC151405
0.6981	Remote Similarity	NPC247976
0.6979	Remote Similarity	NPC44546
0.6977	Remote Similarity	NPC178527
0.6972	Remote Similarity	NPC470252
0.6966	Remote Similarity	NPC155429
0.6966	Remote Similarity	NPC326200
0.6964	Remote Similarity	NPC471721
0.6964	Remote Similarity	NPC294458
0.6957	Remote Similarity	NPC89324
0.6952	Remote Similarity	NPC245927
0.6952	Remote Similarity	NPC469481
0.6947	Remote Similarity	NPC103387
0.6944	Remote Similarity	NPC191215
0.6944	Remote Similarity	NPC142326
0.6944	Remote Similarity	NPC274089
0.6944	Remote Similarity	NPC94751
0.6939	Remote Similarity	NPC96625
0.6937	Remote Similarity	NPC66208
0.6923	Remote Similarity	NPC50872
0.6915	Remote Similarity	NPC190567
0.6915	Remote Similarity	NPC157055
0.6909	Remote Similarity	NPC273837
0.6907	Remote Similarity	NPC252067
0.6907	Remote Similarity	NPC123476
0.6907	Remote Similarity	NPC475710
0.6903	Remote Similarity	NPC476357
0.6903	Remote Similarity	NPC93181
0.69	Remote Similarity	NPC84288
0.69	Remote Similarity	NPC86670
0.69	Remote Similarity	NPC19256
0.69	Remote Similarity	NPC277277
0.69	Remote Similarity	NPC274455
0.69	Remote Similarity	NPC70940
0.6897	Remote Similarity	NPC204784
0.6889	Remote Similarity	NPC1901
0.6887	Remote Similarity	NPC304873
0.6882	Remote Similarity	NPC137847
0.6882	Remote Similarity	NPC76455
0.6881	Remote Similarity	NPC21929
0.6875	Remote Similarity	NPC44830
0.6875	Remote Similarity	NPC215008
0.6875	Remote Similarity	NPC270507
0.6869	Remote Similarity	NPC267262
0.6869	Remote Similarity	NPC153308
0.6863	Remote Similarity	NPC289883
0.6863	Remote Similarity	NPC23453
0.686	Remote Similarity	NPC32312
0.686	Remote Similarity	NPC155172
0.686	Remote Similarity	NPC198023
0.6854	Remote Similarity	NPC263385
0.6842	Remote Similarity	NPC145053
0.6837	Remote Similarity	NPC243166
0.6829	Remote Similarity	NPC475138
0.6827	Remote Similarity	NPC278228
0.6824	Remote Similarity	NPC29680
0.6822	Remote Similarity	NPC329556
0.6818	Remote Similarity	NPC470039
0.6818	Remote Similarity	NPC475006
0.681	Remote Similarity	NPC472697
0.681	Remote Similarity	NPC472698
0.6809	Remote Similarity	NPC272260
0.6809	Remote Similarity	NPC190211
0.6809	Remote Similarity	NPC300205
0.68	Remote Similarity	NPC418308
0.68	Remote Similarity	NPC173443
0.6796	Remote Similarity	NPC472880
0.6792	Remote Similarity	NPC289117
0.6789	Remote Similarity	NPC100767
0.6786	Remote Similarity	NPC218855
0.678	Remote Similarity	NPC311175
0.678	Remote Similarity	NPC473439
0.678	Remote Similarity	NPC300827
0.678	Remote Similarity	NPC37641
0.6777	Remote Similarity	NPC470818
0.6774	Remote Similarity	NPC9796

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 NPC475023 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	994
0.2-0.3	1453
0.3-0.4	3562
0.4-0.5	2172
0.5-0.6	676
0.6-0.7	89
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8222	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD6049	Phase 2
0.8	Intermediate Similarity	NPD3971	Phase 1
0.7677	Intermediate Similarity	NPD3495	Discontinued
0.7629	Intermediate Similarity	NPD7631	Approved
0.7526	Intermediate Similarity	NPD7609	Phase 3
0.75	Intermediate Similarity	NPD6858	Approved
0.75	Intermediate Similarity	NPD9716	Approved
0.75	Intermediate Similarity	NPD7094	Approved
0.7374	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD650	Approved
0.729	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1508	Approved
0.7184	Intermediate Similarity	NPD2066	Phase 3
0.7113	Intermediate Similarity	NPD1087	Approved
0.71	Intermediate Similarity	NPD1088	Approved
0.7087	Intermediate Similarity	NPD5926	Approved
0.7059	Intermediate Similarity	NPD1843	Approved
0.7054	Intermediate Similarity	NPD5951	Approved
0.6981	Remote Similarity	NPD6647	Phase 2
0.6961	Remote Similarity	NPD1693	Approved
0.6957	Remote Similarity	NPD7009	Phase 2
0.6923	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5909	Discontinued
0.69	Remote Similarity	NPD1086	Approved
0.69	Remote Similarity	NPD1089	Approved
0.69	Remote Similarity	NPD3672	Approved
0.69	Remote Similarity	NPD3673	Approved
0.69	Remote Similarity	NPD1090	Approved
0.687	Remote Similarity	NPD7610	Discontinued
0.6838	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1929	Approved
0.6822	Remote Similarity	NPD1930	Approved
0.68	Remote Similarity	NPD800	Approved
0.68	Remote Similarity	NPD5347	Phase 2
0.68	Remote Similarity	NPD5346	Phase 2
0.6768	Remote Similarity	NPD1282	Approved
0.6754	Remote Similarity	NPD4766	Approved
0.6742	Remote Similarity	NPD1673	Approved
0.6731	Remote Similarity	NPD1989	Approved
0.6702	Remote Similarity	NPD225	Approved
0.6702	Remote Similarity	NPD227	Approved
0.6699	Remote Similarity	NPD1563	Approved
0.6696	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD942	Approved
0.6667	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD7076	Approved
0.6667	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7077	Approved
0.66	Remote Similarity	NPD4793	Discontinued
0.6574	Remote Similarity	NPD1932	Approved
0.6562	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD2932	Approved
0.6549	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1202	Approved
0.6518	Remote Similarity	NPD2329	Discontinued
0.6518	Remote Similarity	NPD2182	Approved
0.6514	Remote Similarity	NPD5765	Approved
0.6509	Remote Similarity	NPD1565	Approved
0.6509	Remote Similarity	NPD1564	Approved
0.6509	Remote Similarity	NPD1566	Phase 3
0.6505	Remote Similarity	NPD1239	Approved
0.65	Remote Similarity	NPD9259	Approved
0.65	Remote Similarity	NPD9257	Approved
0.6495	Remote Similarity	NPD226	Approved
0.6486	Remote Similarity	NPD6685	Approved
0.648	Remote Similarity	NPD7055	Discontinued
0.6476	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3025	Approved
0.6471	Remote Similarity	NPD689	Discontinued
0.6471	Remote Similarity	NPD3024	Approved
0.6465	Remote Similarity	NPD4544	Approved
0.6458	Remote Similarity	NPD9490	Approved
0.6457	Remote Similarity	NPD7961	Discontinued
0.6455	Remote Similarity	NPD164	Approved
0.6452	Remote Similarity	NPD4687	Approved
0.6452	Remote Similarity	NPD4058	Approved
0.6417	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD3019	Approved
0.64	Remote Similarity	NPD5736	Approved
0.6364	Remote Similarity	NPD675	Discontinued
0.6364	Remote Similarity	NPD9491	Approved
0.6364	Remote Similarity	NPD3023	Approved
0.6364	Remote Similarity	NPD3026	Approved
0.6325	Remote Similarity	NPD2629	Approved
0.6321	Remote Similarity	NPD4094	Approved
0.6316	Remote Similarity	NPD4233	Approved
0.6316	Remote Similarity	NPD4234	Approved
0.6316	Remote Similarity	NPD5239	Approved
0.6316	Remote Similarity	NPD5240	Approved
0.6316	Remote Similarity	NPD2067	Discontinued
0.6316	Remote Similarity	NPD5236	Approved
0.6316	Remote Similarity	NPD5237	Approved
0.6316	Remote Similarity	NPD5235	Approved
0.6311	Remote Similarity	NPD5618	Discontinued
0.6299	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5733	Approved
0.6273	Remote Similarity	NPD2193	Phase 2
0.6273	Remote Similarity	NPD2196	Discontinued
0.6273	Remote Similarity	NPD2648	Phase 3
0.6271	Remote Similarity	NPD4198	Discontinued
0.627	Remote Similarity	NPD7084	Phase 3
0.6261	Remote Similarity	NPD2201	Approved
0.625	Remote Similarity	NPD7236	Approved
0.625	Remote Similarity	NPD4479	Discontinued
0.625	Remote Similarity	NPD9258	Approved
0.625	Remote Similarity	NPD5048	Discontinued
0.625	Remote Similarity	NPD9256	Approved
0.6239	Remote Similarity	NPD1238	Approved
0.6237	Remote Similarity	NPD5276	Approved
0.6207	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4655	Approved
0.6204	Remote Similarity	NPD4657	Approved
0.6202	Remote Similarity	NPD6663	Approved
0.6202	Remote Similarity	NPD8032	Phase 2
0.6196	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5706	Approved
0.6195	Remote Similarity	NPD3134	Approved
0.6195	Remote Similarity	NPD5704	Approved
0.6195	Remote Similarity	NPD5705	Approved
0.619	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6287	Discontinued
0.6176	Remote Similarity	NPD3099	Discontinued
0.6174	Remote Similarity	NPD1317	Discontinued
0.6172	Remote Similarity	NPD7008	Discontinued
0.6154	Remote Similarity	NPD2607	Approved
0.6148	Remote Similarity	NPD4059	Approved
0.6136	Remote Similarity	NPD4193	Approved
0.6136	Remote Similarity	NPD4194	Approved
0.6136	Remote Similarity	NPD4191	Approved
0.6136	Remote Similarity	NPD4192	Approved
0.6129	Remote Similarity	NPD6637	Approved
0.6129	Remote Similarity	NPD4691	Approved
0.6129	Remote Similarity	NPD4747	Approved
0.6124	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD3644	Approved
0.6121	Remote Similarity	NPD3642	Approved
0.6121	Remote Similarity	NPD3643	Approved
0.6117	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7741	Discontinued
0.6116	Remote Similarity	NPD3091	Approved
0.6111	Remote Similarity	NPD3093	Approved
0.6111	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD3346	Approved
0.6095	Remote Similarity	NPD3344	Approved
0.6083	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD1066	Discontinued
0.6075	Remote Similarity	NPD3982	Approved
0.6075	Remote Similarity	NPD2878	Approved
0.6075	Remote Similarity	NPD3980	Approved
0.6071	Remote Similarity	NPD3357	Discontinued
0.6071	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6912	Phase 3
0.6066	Remote Similarity	NPD5691	Approved
0.6061	Remote Similarity	NPD3979	Approved
0.6061	Remote Similarity	NPD3904	Approved
0.6061	Remote Similarity	NPD3981	Approved
0.6061	Remote Similarity	NPD3903	Approved
0.6058	Remote Similarity	NPD1101	Approved
0.605	Remote Similarity	NPD690	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4635	Approved
0.6034	Remote Similarity	NPD1752	Approved
0.6034	Remote Similarity	NPD5278	Discontinued
0.6034	Remote Similarity	NPD1756	Approved
0.6034	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6065	Approved
0.6032	Remote Similarity	NPD1876	Approved
0.6031	Remote Similarity	NPD4140	Approved
0.6028	Remote Similarity	NPD7239	Suspended
0.6022	Remote Similarity	NPD4137	Phase 3
0.6019	Remote Similarity	NPD1697	Approved
0.6019	Remote Similarity	NPD9260	Approved
0.6016	Remote Similarity	NPD4199	Phase 3
0.6016	Remote Similarity	NPD4626	Approved
0.6016	Remote Similarity	NPD3095	Discontinued
0.6	Remote Similarity	NPD4263	Approved
0.6	Remote Similarity	NPD253	Approved
0.6	Remote Similarity	NPD3035	Approved
0.6	Remote Similarity	NPD3317	Approved
0.6	Remote Similarity	NPD4813	Approved
0.5983	Remote Similarity	NPD5927	Discontinued
0.5982	Remote Similarity	NPD6027	Approved
0.5982	Remote Similarity	NPD4803	Discontinued
0.5982	Remote Similarity	NPD2171	Approved
0.5982	Remote Similarity	NPD6024	Approved
0.597	Remote Similarity	NPD7305	Phase 1
0.5966	Remote Similarity	NPD2650	Approved
0.5966	Remote Similarity	NPD3598	Phase 3
0.5966	Remote Similarity	NPD2652	Approved
0.5965	Remote Similarity	NPD1677	Discontinued
0.5965	Remote Similarity	NPD2197	Approved
0.5965	Remote Similarity	NPD2192	Approved
0.5963	Remote Similarity	NPD2895	Discontinued
0.595	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.595	Remote Similarity	NPD3797	Approved
0.5946	Remote Similarity	NPD3020	Approved
0.5946	Remote Similarity	NPD7798	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