NPASS Compound

Structure

CID125153 OpenBabel06191715482D 21 22 0 0 1 0 0 0 0 0999 V2000 -0.9781 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 -0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4487 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 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 -2.4487 -1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 -0.1810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0181 1.4013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 1.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 6 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 17 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	307.454
LogP:	3.387
LogD:	3.006
LogS:	-4.12
# Rotatable Bonds:	4
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.863
Synthetic Accessibility Score:	3.03
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.067
MDCK Permeability:	2.3864811737439595e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.171
Plasma Protein Binding (PPB):	94.1040267944336%
Volume Distribution (VD):	0.212
Pgp-substrate:	3.873335838317871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.678
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.391
CYP2C9-substrate:	0.835
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.453
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	1.189
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.079
Skin Sensitization:	0.078
Carcinogencity:	0.328
Eye Corrosion:	0.015
Eye Irritation:	0.174
Respiratory Toxicity:	0.774

Download Data

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

Natural Product: NPC125153

Natural Product ID:	NPC125153
*Common Name:**	(1S,3R)-3-(4-Methoxybenzoyl)-1,2,2-Trimethylcyclopentane-1-Carboxylic Acid
IUPAC Name:	(1S,3R)-3-(4-methoxybenzoyl)-1,2,2-trimethylcyclopentane-1-carboxylic acid
Synonyms:
Standard InCHIKey:	JZMUCLZEZUFWDA-SUMWQHHRSA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-16(2)13(9-10-17(16,3)15(19)20)14(18)11-5-7-12(21-4)8-6-11/h5-8,13H,9-10H2,1-4H3,(H,19,20)/t13-,17+/m0/s1
SMILES:	COc1ccc(cc1)C(=O)[C@@H]1CC[C@](C1(C)C)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1553259
PubChem CID:	196225
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO14081	Derris eriocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14081	Derris eriocarpa	Species	Fabaceae	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
Potency	6

Activity Type	# Activity
Individual Protein	2
Organism	1
Others	2
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	112201.8	nM	PMID[456281]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[456281]
NPT2	Others	Unspecified		Potency	=	16360.1	nM	PMID[456281]
NPT2	Others	Unspecified		Potency	n.a.	16360.1	nM	PMID[456281]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[456281]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[456281]

☑ 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 NPC125153 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	281
0.1-0.2	1362
0.2-0.3	2816
0.3-0.4	7047
0.4-0.5	11497
0.5-0.6	6390
0.6-0.7	10038
0.7-0.8	3229
0.8-0.85	34
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8759	High Similarity	NPC51181
0.8468	Intermediate Similarity	NPC109241
0.8406	Intermediate Similarity	NPC170718
0.837	Intermediate Similarity	NPC470976
0.837	Intermediate Similarity	NPC470977
0.837	Intermediate Similarity	NPC196979
0.8359	Intermediate Similarity	NPC61779
0.8358	Intermediate Similarity	NPC194979
0.8346	Intermediate Similarity	NPC469954
0.8346	Intermediate Similarity	NPC293387
0.8346	Intermediate Similarity	NPC121104
0.8306	Intermediate Similarity	NPC23332
0.8296	Intermediate Similarity	NPC183348
0.8296	Intermediate Similarity	NPC282230
0.8284	Intermediate Similarity	NPC2596
0.8271	Intermediate Similarity	NPC204579
0.8271	Intermediate Similarity	NPC110211
0.8258	Intermediate Similarity	NPC221798
0.8235	Intermediate Similarity	NPC15083
0.8226	Intermediate Similarity	NPC183648
0.8222	Intermediate Similarity	NPC170546
0.8222	Intermediate Similarity	NPC66246
0.8189	Intermediate Similarity	NPC220540
0.8156	Intermediate Similarity	NPC148374
0.8156	Intermediate Similarity	NPC473988
0.8145	Intermediate Similarity	NPC234639
0.814	Intermediate Similarity	NPC293424
0.8138	Intermediate Similarity	NPC286038
0.8134	Intermediate Similarity	NPC475236
0.8129	Intermediate Similarity	NPC477596
0.8125	Intermediate Similarity	NPC470860
0.8106	Intermediate Similarity	NPC291189
0.8106	Intermediate Similarity	NPC69403
0.8099	Intermediate Similarity	NPC28398
0.8085	Intermediate Similarity	NPC23870
0.8082	Intermediate Similarity	NPC66991
0.8071	Intermediate Similarity	NPC471670
0.8062	Intermediate Similarity	NPC240664
0.806	Intermediate Similarity	NPC49938
0.806	Intermediate Similarity	NPC470858
0.8058	Intermediate Similarity	NPC477594
0.8045	Intermediate Similarity	NPC474691
0.8045	Intermediate Similarity	NPC473942
0.8029	Intermediate Similarity	NPC245395
0.8027	Intermediate Similarity	NPC161955
0.8014	Intermediate Similarity	NPC224418
0.8014	Intermediate Similarity	NPC213603
0.8014	Intermediate Similarity	NPC24394
0.8014	Intermediate Similarity	NPC477592
0.8	Intermediate Similarity	NPC474476
0.7984	Intermediate Similarity	NPC19290
0.7984	Intermediate Similarity	NPC131192
0.7971	Intermediate Similarity	NPC164295
0.7971	Intermediate Similarity	NPC239134
0.797	Intermediate Similarity	NPC67300
0.7958	Intermediate Similarity	NPC477593
0.7958	Intermediate Similarity	NPC202260
0.7956	Intermediate Similarity	NPC939
0.7947	Intermediate Similarity	NPC159692
0.7945	Intermediate Similarity	NPC472034
0.7931	Intermediate Similarity	NPC469615
0.7931	Intermediate Similarity	NPC46880
0.7929	Intermediate Similarity	NPC311339
0.7926	Intermediate Similarity	NPC137416
0.7917	Intermediate Similarity	NPC477595
0.7917	Intermediate Similarity	NPC11056
0.7914	Intermediate Similarity	NPC153453
0.7914	Intermediate Similarity	NPC112192
0.7914	Intermediate Similarity	NPC128348
0.7914	Intermediate Similarity	NPC189106
0.7914	Intermediate Similarity	NPC309717
0.7914	Intermediate Similarity	NPC66384
0.7914	Intermediate Similarity	NPC164236
0.791	Intermediate Similarity	NPC141252
0.791	Intermediate Similarity	NPC11799
0.791	Intermediate Similarity	NPC472704
0.7907	Intermediate Similarity	NPC322197
0.7907	Intermediate Similarity	NPC322358
0.7905	Intermediate Similarity	NPC279442
0.7903	Intermediate Similarity	NPC1065
0.7902	Intermediate Similarity	NPC475012
0.7899	Intermediate Similarity	NPC285776
0.7899	Intermediate Similarity	NPC327457
0.7899	Intermediate Similarity	NPC2989
0.7899	Intermediate Similarity	NPC86774
0.7899	Intermediate Similarity	NPC109778
0.7891	Intermediate Similarity	NPC472033
0.7891	Intermediate Similarity	NPC25844
0.7883	Intermediate Similarity	NPC473744
0.7877	Intermediate Similarity	NPC247221
0.7877	Intermediate Similarity	NPC469683
0.7877	Intermediate Similarity	NPC260152
0.7874	Intermediate Similarity	NPC57879
0.7872	Intermediate Similarity	NPC22644
0.7868	Intermediate Similarity	NPC473751
0.7868	Intermediate Similarity	NPC474737
0.7863	Intermediate Similarity	NPC94298
0.7863	Intermediate Similarity	NPC27633
0.7862	Intermediate Similarity	NPC103752
0.7857	Intermediate Similarity	NPC43627
0.7857	Intermediate Similarity	NPC95172
0.7852	Intermediate Similarity	NPC184219
0.7852	Intermediate Similarity	NPC237441
0.7838	Intermediate Similarity	NPC472036
0.7838	Intermediate Similarity	NPC93666
0.7836	Intermediate Similarity	NPC139171
0.7836	Intermediate Similarity	NPC472703
0.7826	Intermediate Similarity	NPC473019
0.7826	Intermediate Similarity	NPC272946
0.782	Intermediate Similarity	NPC225245
0.7817	Intermediate Similarity	NPC71638
0.7817	Intermediate Similarity	NPC215109
0.7817	Intermediate Similarity	NPC64230
0.7817	Intermediate Similarity	NPC170604
0.7812	Intermediate Similarity	NPC17693
0.781	Intermediate Similarity	NPC32163
0.781	Intermediate Similarity	NPC16651
0.781	Intermediate Similarity	NPC37512
0.7803	Intermediate Similarity	NPC264976
0.7801	Intermediate Similarity	NPC27643
0.7801	Intermediate Similarity	NPC213122
0.7801	Intermediate Similarity	NPC474097
0.78	Intermediate Similarity	NPC178048
0.78	Intermediate Similarity	NPC140133
0.7793	Intermediate Similarity	NPC184053
0.7793	Intermediate Similarity	NPC307990
0.7793	Intermediate Similarity	NPC16455
0.7786	Intermediate Similarity	NPC111888
0.7786	Intermediate Similarity	NPC183103
0.7786	Intermediate Similarity	NPC470160
0.7778	Intermediate Similarity	NPC472368
0.7778	Intermediate Similarity	NPC118853
0.777	Intermediate Similarity	NPC247779
0.777	Intermediate Similarity	NPC66905
0.777	Intermediate Similarity	NPC42292
0.777	Intermediate Similarity	NPC475092
0.777	Intermediate Similarity	NPC473149
0.777	Intermediate Similarity	NPC307732
0.777	Intermediate Similarity	NPC476336
0.7769	Intermediate Similarity	NPC51345
0.7763	Intermediate Similarity	NPC25351
0.7762	Intermediate Similarity	NPC119542
0.7755	Intermediate Similarity	NPC313039
0.7755	Intermediate Similarity	NPC169942
0.7755	Intermediate Similarity	NPC109812
0.7755	Intermediate Similarity	NPC473976
0.7755	Intermediate Similarity	NPC198459
0.7755	Intermediate Similarity	NPC131043
0.7754	Intermediate Similarity	NPC2401
0.7754	Intermediate Similarity	NPC229894
0.7748	Intermediate Similarity	NPC48671
0.7746	Intermediate Similarity	NPC89504
0.7746	Intermediate Similarity	NPC286336
0.7746	Intermediate Similarity	NPC88065
0.7746	Intermediate Similarity	NPC95485
0.7746	Intermediate Similarity	NPC61499
0.7744	Intermediate Similarity	NPC470092
0.7742	Intermediate Similarity	NPC38209
0.774	Intermediate Similarity	NPC229218
0.774	Intermediate Similarity	NPC472564
0.774	Intermediate Similarity	NPC18714
0.774	Intermediate Similarity	NPC192597
0.774	Intermediate Similarity	NPC176030
0.774	Intermediate Similarity	NPC250755
0.774	Intermediate Similarity	NPC141817
0.774	Intermediate Similarity	NPC169214
0.7737	Intermediate Similarity	NPC177925
0.7737	Intermediate Similarity	NPC154275
0.7737	Intermediate Similarity	NPC237868
0.7733	Intermediate Similarity	NPC212257
0.7733	Intermediate Similarity	NPC228842
0.773	Intermediate Similarity	NPC329913
0.773	Intermediate Similarity	NPC477368
0.773	Intermediate Similarity	NPC477359
0.773	Intermediate Similarity	NPC283823
0.773	Intermediate Similarity	NPC285054
0.773	Intermediate Similarity	NPC159418
0.773	Intermediate Similarity	NPC126516
0.7727	Intermediate Similarity	NPC161943
0.7727	Intermediate Similarity	NPC205502
0.7727	Intermediate Similarity	NPC474890
0.7727	Intermediate Similarity	NPC273282
0.7724	Intermediate Similarity	NPC109232
0.7724	Intermediate Similarity	NPC477956
0.7724	Intermediate Similarity	NPC155552
0.7724	Intermediate Similarity	NPC469911
0.7721	Intermediate Similarity	NPC89630
0.7721	Intermediate Similarity	NPC111088
0.7721	Intermediate Similarity	NPC470162
0.7721	Intermediate Similarity	NPC470163
0.7718	Intermediate Similarity	NPC52692
0.7714	Intermediate Similarity	NPC473982
0.7714	Intermediate Similarity	NPC473777
0.771	Intermediate Similarity	NPC28951
0.771	Intermediate Similarity	NPC325646
0.7708	Intermediate Similarity	NPC284409
0.7708	Intermediate Similarity	NPC234548
0.7708	Intermediate Similarity	NPC153979
0.7708	Intermediate Similarity	NPC62735
0.7708	Intermediate Similarity	NPC248287

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 NPC125153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	884
0.2-0.3	1386
0.3-0.4	2374
0.4-0.5	2299
0.5-0.6	1359
0.6-0.7	483
0.7-0.8	118
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8397	Intermediate Similarity	NPD1876	Approved
0.8385	Intermediate Similarity	NPD3972	Approved
0.8169	Intermediate Similarity	NPD4628	Phase 3
0.8099	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD2799	Discontinued
0.8014	Intermediate Similarity	NPD6273	Approved
0.7973	Intermediate Similarity	NPD7458	Discontinued
0.7917	Intermediate Similarity	NPD7003	Approved
0.7899	Intermediate Similarity	NPD3268	Approved
0.7868	Intermediate Similarity	NPD2798	Approved
0.7863	Intermediate Similarity	NPD9545	Approved
0.7762	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD6355	Discontinued
0.7721	Intermediate Similarity	NPD1283	Approved
0.7714	Intermediate Similarity	NPD8032	Phase 2
0.7704	Intermediate Similarity	NPD1608	Approved
0.7664	Intermediate Similarity	NPD3266	Approved
0.7664	Intermediate Similarity	NPD3267	Approved
0.7619	Intermediate Similarity	NPD3134	Approved
0.7615	Intermediate Similarity	NPD1241	Discontinued
0.7586	Intermediate Similarity	NPD2344	Approved
0.7586	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD9717	Approved
0.7566	Intermediate Similarity	NPD6599	Discontinued
0.7556	Intermediate Similarity	NPD3847	Discontinued
0.7551	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4110	Phase 3
0.7537	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD2797	Approved
0.7535	Intermediate Similarity	NPD1240	Approved
0.7534	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2313	Discontinued
0.7518	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD2354	Approved
0.75	Intermediate Similarity	NPD1281	Approved
0.7482	Intermediate Similarity	NPD5647	Approved
0.7481	Intermediate Similarity	NPD4626	Approved
0.7481	Intermediate Similarity	NPD17	Approved
0.7451	Intermediate Similarity	NPD7028	Phase 2
0.7448	Intermediate Similarity	NPD1510	Phase 2
0.7444	Intermediate Similarity	NPD9493	Approved
0.7432	Intermediate Similarity	NPD3750	Approved
0.7431	Intermediate Similarity	NPD1607	Approved
0.7429	Intermediate Similarity	NPD9494	Approved
0.7422	Intermediate Similarity	NPD1358	Approved
0.7422	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7819	Suspended
0.7413	Intermediate Similarity	NPD4140	Approved
0.74	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6799	Approved
0.7394	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2309	Approved
0.7383	Intermediate Similarity	NPD3887	Approved
0.7376	Intermediate Similarity	NPD6832	Phase 2
0.7368	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2932	Approved
0.7353	Intermediate Similarity	NPD3019	Approved
0.7353	Intermediate Similarity	NPD1778	Approved
0.7351	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2353	Approved
0.7347	Intermediate Similarity	NPD2346	Discontinued
0.7333	Intermediate Similarity	NPD1894	Discontinued
0.7333	Intermediate Similarity	NPD7236	Approved
0.7329	Intermediate Similarity	NPD3748	Approved
0.7329	Intermediate Similarity	NPD4308	Phase 3
0.7324	Intermediate Similarity	NPD7095	Approved
0.7308	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3140	Approved
0.7292	Intermediate Similarity	NPD3142	Approved
0.7292	Intermediate Similarity	NPD2979	Phase 3
0.7286	Intermediate Similarity	NPD6362	Approved
0.7286	Intermediate Similarity	NPD1203	Approved
0.7279	Intermediate Similarity	NPD2796	Approved
0.7279	Intermediate Similarity	NPD5691	Approved
0.7279	Intermediate Similarity	NPD5585	Approved
0.7279	Intermediate Similarity	NPD1651	Approved
0.7273	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2614	Approved
0.7252	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8127	Discontinued
0.7239	Intermediate Similarity	NPD7157	Approved
0.7237	Intermediate Similarity	NPD2532	Approved
0.7237	Intermediate Similarity	NPD2534	Approved
0.7237	Intermediate Similarity	NPD2533	Approved
0.7237	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4624	Approved
0.723	Intermediate Similarity	NPD6002	Phase 3
0.723	Intermediate Similarity	NPD6004	Phase 3
0.723	Intermediate Similarity	NPD1471	Phase 3
0.723	Intermediate Similarity	NPD6005	Phase 3
0.723	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6663	Approved
0.72	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8166	Discontinued
0.7194	Intermediate Similarity	NPD1481	Phase 2
0.7192	Intermediate Similarity	NPD6651	Approved
0.7192	Intermediate Similarity	NPD6653	Approved
0.7183	Intermediate Similarity	NPD5736	Approved
0.7181	Intermediate Similarity	NPD1549	Phase 2
0.7181	Intermediate Similarity	NPD4534	Discontinued
0.7181	Intermediate Similarity	NPD5958	Discontinued
0.7179	Intermediate Similarity	NPD6873	Phase 2
0.7174	Intermediate Similarity	NPD3026	Approved
0.7174	Intermediate Similarity	NPD3023	Approved
0.7174	Intermediate Similarity	NPD3496	Discontinued
0.7172	Intermediate Similarity	NPD4307	Phase 2
0.717	Intermediate Similarity	NPD7075	Discontinued
0.7169	Intermediate Similarity	NPD6765	Approved
0.7169	Intermediate Similarity	NPD6764	Approved
0.7164	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4476	Approved
0.7162	Intermediate Similarity	NPD4477	Approved
0.7153	Intermediate Similarity	NPD3024	Approved
0.7153	Intermediate Similarity	NPD411	Approved
0.7153	Intermediate Similarity	NPD3025	Approved
0.7152	Intermediate Similarity	NPD5977	Approved
0.7152	Intermediate Similarity	NPD5978	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD1670	Discontinued
0.7133	Intermediate Similarity	NPD1243	Approved
0.7133	Intermediate Similarity	NPD2800	Approved
0.7132	Intermediate Similarity	NPD5536	Phase 2
0.7123	Intermediate Similarity	NPD230	Phase 1
0.7123	Intermediate Similarity	NPD447	Suspended
0.7122	Intermediate Similarity	NPD1535	Discovery
0.7122	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1019	Discontinued
0.7105	Intermediate Similarity	NPD7440	Discontinued
0.7103	Intermediate Similarity	NPD6233	Phase 2
0.7103	Intermediate Similarity	NPD4062	Phase 3
0.7101	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2182	Approved
0.7099	Intermediate Similarity	NPD6808	Phase 2
0.7099	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7239	Suspended
0.7095	Intermediate Similarity	NPD7033	Discontinued
0.7083	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5049	Phase 3
0.7063	Intermediate Similarity	NPD3749	Approved
0.7054	Intermediate Similarity	NPD164	Approved
0.7051	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2438	Suspended
0.7047	Intermediate Similarity	NPD2531	Phase 2
0.7032	Intermediate Similarity	NPD920	Approved
0.7025	Intermediate Similarity	NPD7577	Discontinued
0.7025	Intermediate Similarity	NPD6801	Discontinued
0.7021	Intermediate Similarity	NPD4359	Approved
0.7013	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD6784	Approved
0.7	Intermediate Similarity	NPD6785	Approved
0.7	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD6287	Discontinued
0.6993	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1929	Approved
0.6977	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1930	Approved
0.6972	Remote Similarity	NPD3225	Approved
0.6972	Remote Similarity	NPD196	Phase 1
0.697	Remote Similarity	NPD7473	Discontinued
0.697	Remote Similarity	NPD2684	Approved
0.6964	Remote Similarity	NPD7685	Pre-registration
0.6963	Remote Similarity	NPD5283	Phase 1
0.6954	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD454	Approved
0.694	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4060	Phase 1
0.6937	Remote Similarity	NPD3817	Phase 2
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD7199	Phase 2
0.6933	Remote Similarity	NPD6100	Approved
0.6933	Remote Similarity	NPD1551	Phase 2
0.6928	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1164	Approved
0.6923	Remote Similarity	NPD987	Approved
0.6912	Remote Similarity	NPD5951	Approved
0.6909	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2654	Approved
0.6903	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5327	Phase 3
0.6894	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD9264	Approved
0.6894	Remote Similarity	NPD3882	Suspended
0.6894	Remote Similarity	NPD9267	Approved
0.6894	Remote Similarity	NPD9263	Approved
0.6892	Remote Similarity	NPD1933	Approved
0.689	Remote Similarity	NPD7315	Approved
0.689	Remote Similarity	NPD6232	Discontinued

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