NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	272.628
LogP:	4.11
LogD:	4.03
LogS:	-4.252
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.813
Synthetic Accessibility Score:	2.458
Fsp3:	0.4
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:	-4.51
MDCK Permeability:	4.6168293920345604e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.943
Plasma Protein Binding (PPB):	90.52202606201172%
Volume Distribution (VD):	1.262
Pgp-substrate:	12.525025367736816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.925
CYP2C19-substrate:	0.209
CYP2C9-inhibitor:	0.867
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.479
CYP2D6-substrate:	0.317
CYP3A4-inhibitor:	0.391
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	14.968
Half-life (T1/2):	0.779

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.423
Rat Oral Acute Toxicity:	0.279
Maximum Recommended Daily Dose:	0.572
Skin Sensitization:	0.842
Carcinogencity:	0.858
Eye Corrosion:	0.137
Eye Irritation:	0.784
Respiratory Toxicity:	0.323

Download Data

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

Natural Product: NPC190212

Natural Product ID:	NPC190212
*Common Name:**	9-(3-Methylbutanoyl)-8,10-Dehydrothymol
IUPAC Name:	2-(2-hydroxy-4-methylphenyl)prop-2-enyl 3-methylbutanoate
Synonyms:
Standard InCHIKey:	IYXKURCVMVQNOD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-10(2)7-15(17)18-9-12(4)13-6-5-11(3)8-14(13)16/h5-6,8,10,16H,4,7,9H2,1-3H3
SMILES:	CC(CC(=O)OCC(=C)c1ccc(cc1O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795986
PubChem CID:	53262899
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001272] Cresols [CHEMONTID:0001273] Meta cresols

*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
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21391659]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30653318]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	39.6	%	PMID[547485]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18300.0	nM	PMID[547485]

☑ 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 NPC190212 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	209
0.1-0.2	1082
0.2-0.3	3092
0.3-0.4	8100
0.4-0.5	11382
0.5-0.6	7194
0.6-0.7	9464
0.7-0.8	2032
0.8-0.85	123
0.85-0.9	12
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9905	High Similarity	NPC26615
0.9537	High Similarity	NPC41851
0.9204	High Similarity	NPC328485
0.8947	High Similarity	NPC160235
0.8868	High Similarity	NPC235762
0.8868	High Similarity	NPC471228
0.8803	High Similarity	NPC325301
0.8803	High Similarity	NPC327070
0.8785	High Similarity	NPC475225
0.8696	High Similarity	NPC206205
0.8679	High Similarity	NPC174911
0.8661	High Similarity	NPC228452
0.8621	High Similarity	NPC472593
0.8609	High Similarity	NPC160199
0.8545	High Similarity	NPC66834
0.8509	High Similarity	NPC197513
0.8505	High Similarity	NPC72729
0.85	High Similarity	NPC469568
0.8491	Intermediate Similarity	NPC79241
0.8491	Intermediate Similarity	NPC6597
0.8487	Intermediate Similarity	NPC132518
0.8487	Intermediate Similarity	NPC477151
0.8426	Intermediate Similarity	NPC94343
0.8411	Intermediate Similarity	NPC171843
0.8407	Intermediate Similarity	NPC228609
0.8396	Intermediate Similarity	NPC259512
0.8396	Intermediate Similarity	NPC312132
0.8393	Intermediate Similarity	NPC75272
0.8393	Intermediate Similarity	NPC471954
0.839	Intermediate Similarity	NPC478121
0.8362	Intermediate Similarity	NPC123559
0.8347	Intermediate Similarity	NPC117794
0.8333	Intermediate Similarity	NPC478058
0.8333	Intermediate Similarity	NPC121168
0.8333	Intermediate Similarity	NPC472591
0.8333	Intermediate Similarity	NPC280760
0.8319	Intermediate Similarity	NPC322569
0.8318	Intermediate Similarity	NPC474073
0.8306	Intermediate Similarity	NPC131684
0.8305	Intermediate Similarity	NPC98748
0.8304	Intermediate Similarity	NPC31274
0.8293	Intermediate Similarity	NPC257947
0.8293	Intermediate Similarity	NPC66331
0.8291	Intermediate Similarity	NPC325295
0.8291	Intermediate Similarity	NPC76308
0.8279	Intermediate Similarity	NPC472592
0.8279	Intermediate Similarity	NPC287473
0.8276	Intermediate Similarity	NPC232165
0.8273	Intermediate Similarity	NPC130817
0.8264	Intermediate Similarity	NPC477152
0.8257	Intermediate Similarity	NPC477685
0.825	Intermediate Similarity	NPC25168
0.8241	Intermediate Similarity	NPC299762
0.8241	Intermediate Similarity	NPC33675
0.823	Intermediate Similarity	NPC98392
0.8214	Intermediate Similarity	NPC233320
0.8198	Intermediate Similarity	NPC47284
0.8197	Intermediate Similarity	NPC474237
0.819	Intermediate Similarity	NPC81808
0.819	Intermediate Similarity	NPC114918
0.819	Intermediate Similarity	NPC231150
0.8182	Intermediate Similarity	NPC13426
0.8182	Intermediate Similarity	NPC304638
0.8167	Intermediate Similarity	NPC241001
0.8167	Intermediate Similarity	NPC165197
0.8165	Intermediate Similarity	NPC129373
0.8165	Intermediate Similarity	NPC48730
0.8165	Intermediate Similarity	NPC248396
0.8158	Intermediate Similarity	NPC132720
0.8148	Intermediate Similarity	NPC152097
0.8142	Intermediate Similarity	NPC279887
0.8142	Intermediate Similarity	NPC68260
0.813	Intermediate Similarity	NPC170749
0.8125	Intermediate Similarity	NPC53740
0.812	Intermediate Similarity	NPC474967
0.8108	Intermediate Similarity	NPC93831
0.8103	Intermediate Similarity	NPC28784
0.8103	Intermediate Similarity	NPC296144
0.8091	Intermediate Similarity	NPC252105
0.8091	Intermediate Similarity	NPC80800
0.8087	Intermediate Similarity	NPC275627
0.8087	Intermediate Similarity	NPC139946
0.8087	Intermediate Similarity	NPC54373
0.8083	Intermediate Similarity	NPC14177
0.8083	Intermediate Similarity	NPC72977
0.808	Intermediate Similarity	NPC81261
0.8073	Intermediate Similarity	NPC260775
0.807	Intermediate Similarity	NPC26013
0.807	Intermediate Similarity	NPC282855
0.8067	Intermediate Similarity	NPC203124
0.8067	Intermediate Similarity	NPC41567
0.8067	Intermediate Similarity	NPC309434
0.8053	Intermediate Similarity	NPC474352
0.8049	Intermediate Similarity	NPC265413
0.8049	Intermediate Similarity	NPC10154
0.8036	Intermediate Similarity	NPC303141
0.8034	Intermediate Similarity	NPC33749
0.8034	Intermediate Similarity	NPC474114
0.8034	Intermediate Similarity	NPC474050
0.8034	Intermediate Similarity	NPC473931
0.8034	Intermediate Similarity	NPC328593
0.8034	Intermediate Similarity	NPC261453
0.8033	Intermediate Similarity	NPC297193
0.8033	Intermediate Similarity	NPC46634
0.8031	Intermediate Similarity	NPC7012
0.8018	Intermediate Similarity	NPC108497
0.8018	Intermediate Similarity	NPC12870
0.8018	Intermediate Similarity	NPC24327
0.8017	Intermediate Similarity	NPC17693
0.8017	Intermediate Similarity	NPC302371
0.8	Intermediate Similarity	NPC38181
0.8	Intermediate Similarity	NPC471535
0.8	Intermediate Similarity	NPC70677
0.8	Intermediate Similarity	NPC183700
0.8	Intermediate Similarity	NPC121866
0.8	Intermediate Similarity	NPC208229
0.8	Intermediate Similarity	NPC130756
0.8	Intermediate Similarity	NPC253746
0.8	Intermediate Similarity	NPC130103
0.8	Intermediate Similarity	NPC63345
0.8	Intermediate Similarity	NPC20230
0.8	Intermediate Similarity	NPC12931
0.8	Intermediate Similarity	NPC328459
0.8	Intermediate Similarity	NPC90522
0.7983	Intermediate Similarity	NPC175799
0.7983	Intermediate Similarity	NPC610
0.7983	Intermediate Similarity	NPC145023
0.7983	Intermediate Similarity	NPC200988
0.7982	Intermediate Similarity	NPC475078
0.7982	Intermediate Similarity	NPC169450
0.7967	Intermediate Similarity	NPC261992
0.7967	Intermediate Similarity	NPC275145
0.7966	Intermediate Similarity	NPC233669
0.7965	Intermediate Similarity	NPC310456
0.7965	Intermediate Similarity	NPC30416
0.7965	Intermediate Similarity	NPC317592
0.7963	Intermediate Similarity	NPC246679
0.7963	Intermediate Similarity	NPC257182
0.7951	Intermediate Similarity	NPC249340
0.7951	Intermediate Similarity	NPC162935
0.7949	Intermediate Similarity	NPC109241
0.7949	Intermediate Similarity	NPC148969
0.7949	Intermediate Similarity	NPC264558
0.7949	Intermediate Similarity	NPC95381
0.7946	Intermediate Similarity	NPC475580
0.7946	Intermediate Similarity	NPC227458
0.7946	Intermediate Similarity	NPC244513
0.7946	Intermediate Similarity	NPC218879
0.7946	Intermediate Similarity	NPC272029
0.7946	Intermediate Similarity	NPC323810
0.7944	Intermediate Similarity	NPC210497
0.7944	Intermediate Similarity	NPC147284
0.7944	Intermediate Similarity	NPC306884
0.7944	Intermediate Similarity	NPC162314
0.7944	Intermediate Similarity	NPC94139
0.7944	Intermediate Similarity	NPC29373
0.7944	Intermediate Similarity	NPC3358
0.7937	Intermediate Similarity	NPC176590
0.7928	Intermediate Similarity	NPC12221
0.7925	Intermediate Similarity	NPC312304
0.7925	Intermediate Similarity	NPC192
0.7923	Intermediate Similarity	NPC29317
0.7923	Intermediate Similarity	NPC229638
0.7923	Intermediate Similarity	NPC267539
0.7923	Intermediate Similarity	NPC475011
0.7923	Intermediate Similarity	NPC176102
0.7923	Intermediate Similarity	NPC71108
0.7923	Intermediate Similarity	NPC204257
0.7923	Intermediate Similarity	NPC254832
0.792	Intermediate Similarity	NPC474944
0.7917	Intermediate Similarity	NPC328694
0.7917	Intermediate Similarity	NPC94637
0.7917	Intermediate Similarity	NPC86198
0.7913	Intermediate Similarity	NPC473524
0.7909	Intermediate Similarity	NPC245561
0.7909	Intermediate Similarity	NPC128723
0.7905	Intermediate Similarity	NPC27974
0.7903	Intermediate Similarity	NPC474532
0.7903	Intermediate Similarity	NPC184219
0.7899	Intermediate Similarity	NPC281277
0.7895	Intermediate Similarity	NPC158253
0.7895	Intermediate Similarity	NPC228737
0.7895	Intermediate Similarity	NPC204901
0.7895	Intermediate Similarity	NPC320439
0.7895	Intermediate Similarity	NPC232523
0.7895	Intermediate Similarity	NPC260952
0.7891	Intermediate Similarity	NPC258073
0.7886	Intermediate Similarity	NPC302211
0.7886	Intermediate Similarity	NPC188997
0.7876	Intermediate Similarity	NPC243677
0.7876	Intermediate Similarity	NPC288760
0.7876	Intermediate Similarity	NPC127676
0.7876	Intermediate Similarity	NPC37802
0.7876	Intermediate Similarity	NPC227255
0.7876	Intermediate Similarity	NPC117115
0.787	Intermediate Similarity	NPC245187
0.787	Intermediate Similarity	NPC152415
0.7869	Intermediate Similarity	NPC470849
0.7869	Intermediate Similarity	NPC96423
0.7869	Intermediate Similarity	NPC164852

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 NPC190212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	821
0.2-0.3	1457
0.3-0.4	2522
0.4-0.5	2095
0.5-0.6	1284
0.6-0.7	659
0.7-0.8	110
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8476	Intermediate Similarity	NPD844	Approved
0.8396	Intermediate Similarity	NPD288	Approved
0.839	Intermediate Similarity	NPD1778	Approved
0.8083	Intermediate Similarity	NPD4626	Approved
0.8017	Intermediate Similarity	NPD3496	Discontinued
0.8	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5691	Approved
0.7857	Intermediate Similarity	NPD5736	Approved
0.7815	Intermediate Similarity	NPD6671	Approved
0.7778	Intermediate Similarity	NPD845	Approved
0.776	Intermediate Similarity	NPD1283	Approved
0.7759	Intermediate Similarity	NPD4750	Phase 3
0.775	Intermediate Similarity	NPD9493	Approved
0.7712	Intermediate Similarity	NPD7635	Approved
0.7705	Intermediate Similarity	NPD5585	Approved
0.7692	Intermediate Similarity	NPD4060	Phase 1
0.7623	Intermediate Similarity	NPD9545	Approved
0.7615	Intermediate Similarity	NPD6663	Approved
0.76	Intermediate Similarity	NPD1608	Approved
0.7589	Intermediate Similarity	NPD3020	Approved
0.7578	Intermediate Similarity	NPD2237	Approved
0.7559	Intermediate Similarity	NPD2797	Approved
0.7545	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD1281	Approved
0.752	Intermediate Similarity	NPD1611	Approved
0.75	Intermediate Similarity	NPD3134	Approved
0.7477	Intermediate Similarity	NPD2860	Approved
0.7477	Intermediate Similarity	NPD2859	Approved
0.7456	Intermediate Similarity	NPD846	Approved
0.7456	Intermediate Similarity	NPD940	Approved
0.7444	Intermediate Similarity	NPD6653	Approved
0.7424	Intermediate Similarity	NPD2979	Phase 3
0.7407	Intermediate Similarity	NPD2935	Discontinued
0.7407	Intermediate Similarity	NPD6032	Approved
0.7402	Intermediate Similarity	NPD4359	Approved
0.7402	Intermediate Similarity	NPD4749	Approved
0.7387	Intermediate Similarity	NPD2934	Approved
0.7387	Intermediate Similarity	NPD2933	Approved
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.736	Intermediate Similarity	NPD2932	Approved
0.736	Intermediate Similarity	NPD3019	Approved
0.736	Intermediate Similarity	NPD17	Approved
0.735	Intermediate Similarity	NPD968	Approved
0.735	Intermediate Similarity	NPD1444	Approved
0.735	Intermediate Similarity	NPD1445	Approved
0.7333	Intermediate Similarity	NPD228	Approved
0.7321	Intermediate Similarity	NPD1809	Phase 2
0.7319	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD8166	Discontinued
0.7311	Intermediate Similarity	NPD3021	Approved
0.7311	Intermediate Similarity	NPD3022	Approved
0.7308	Intermediate Similarity	NPD2861	Phase 2
0.7302	Intermediate Similarity	NPD3847	Discontinued
0.7295	Intermediate Similarity	NPD2629	Approved
0.7293	Intermediate Similarity	NPD4140	Approved
0.7293	Intermediate Similarity	NPD826	Approved
0.7293	Intermediate Similarity	NPD825	Approved
0.7288	Intermediate Similarity	NPD290	Approved
0.7288	Intermediate Similarity	NPD2342	Discontinued
0.7288	Intermediate Similarity	NPD1358	Approved
0.728	Intermediate Similarity	NPD1651	Approved
0.7273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7266	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD800	Approved
0.7244	Intermediate Similarity	NPD1535	Discovery
0.7244	Intermediate Similarity	NPD422	Phase 1
0.7236	Intermediate Similarity	NPD4198	Discontinued
0.7236	Intermediate Similarity	NPD255	Approved
0.7236	Intermediate Similarity	NPD256	Approved
0.7234	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD2684	Approved
0.7227	Intermediate Similarity	NPD9266	Approved
0.7227	Intermediate Similarity	NPD74	Approved
0.7226	Intermediate Similarity	NPD6004	Phase 3
0.7226	Intermediate Similarity	NPD6005	Phase 3
0.7226	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6002	Phase 3
0.7226	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5763	Approved
0.7213	Intermediate Similarity	NPD1398	Phase 1
0.7209	Intermediate Similarity	NPD6696	Suspended
0.72	Intermediate Similarity	NPD3091	Approved
0.72	Intermediate Similarity	NPD1894	Discontinued
0.72	Intermediate Similarity	NPD1759	Phase 1
0.7197	Intermediate Similarity	NPD7095	Approved
0.7196	Intermediate Similarity	NPD111	Approved
0.7188	Intermediate Similarity	NPD2230	Approved
0.7188	Intermediate Similarity	NPD1481	Phase 2
0.7188	Intermediate Similarity	NPD2232	Approved
0.7188	Intermediate Similarity	NPD9717	Approved
0.7188	Intermediate Similarity	NPD2233	Approved
0.7182	Intermediate Similarity	NPD1086	Approved
0.7182	Intermediate Similarity	NPD1090	Approved
0.7182	Intermediate Similarity	NPD1089	Approved
0.7177	Intermediate Similarity	NPD7340	Approved
0.7167	Intermediate Similarity	NPD1792	Phase 2
0.7154	Intermediate Similarity	NPD6362	Approved
0.7153	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD9264	Approved
0.7143	Intermediate Similarity	NPD9263	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7985	Registered
0.7143	Intermediate Similarity	NPD9267	Approved
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7097	Phase 1
0.7131	Intermediate Similarity	NPD5535	Approved
0.712	Intermediate Similarity	NPD7644	Approved
0.712	Intermediate Similarity	NPD1758	Phase 1
0.7119	Intermediate Similarity	NPD9697	Approved
0.7111	Intermediate Similarity	NPD230	Phase 1
0.7111	Intermediate Similarity	NPD447	Suspended
0.7109	Intermediate Similarity	NPD1610	Phase 2
0.7109	Intermediate Similarity	NPD1201	Approved
0.7101	Intermediate Similarity	NPD2346	Discontinued
0.709	Intermediate Similarity	NPD4870	Approved
0.708	Intermediate Similarity	NPD1693	Approved
0.708	Intermediate Similarity	NPD4308	Phase 3
0.708	Intermediate Similarity	NPD7033	Discontinued
0.7071	Intermediate Similarity	NPD7003	Approved
0.7071	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4110	Phase 3
0.7068	Intermediate Similarity	NPD4625	Phase 3
0.7054	Intermediate Similarity	NPD2235	Phase 2
0.7054	Intermediate Similarity	NPD2231	Phase 2
0.7054	Intermediate Similarity	NPD1088	Approved
0.705	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1712	Approved
0.7043	Intermediate Similarity	NPD9495	Approved
0.704	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5909	Discontinued
0.7034	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2531	Phase 2
0.7029	Intermediate Similarity	NPD2438	Suspended
0.7029	Intermediate Similarity	NPD1551	Phase 2
0.7029	Intermediate Similarity	NPD4477	Approved
0.7029	Intermediate Similarity	NPD4476	Approved
0.7023	Intermediate Similarity	NPD1203	Approved
0.7023	Intermediate Similarity	NPD987	Approved
0.7016	Intermediate Similarity	NPD9614	Approved
0.7016	Intermediate Similarity	NPD9618	Approved
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2533	Approved
0.6993	Remote Similarity	NPD1578	Phase 2
0.6993	Remote Similarity	NPD2532	Approved
0.6993	Remote Similarity	NPD2534	Approved
0.6992	Remote Similarity	NPD4908	Phase 1
0.6992	Remote Similarity	NPD821	Approved
0.6992	Remote Similarity	NPD1138	Approved
0.6992	Remote Similarity	NPD7843	Approved
0.6992	Remote Similarity	NPD2614	Approved
0.6985	Remote Similarity	NPD4618	Approved
0.6985	Remote Similarity	NPD4622	Approved
0.6985	Remote Similarity	NPD555	Phase 2
0.6978	Remote Similarity	NPD7266	Discontinued
0.6978	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3092	Approved
0.697	Remote Similarity	NPD258	Approved
0.697	Remote Similarity	NPD257	Approved
0.697	Remote Similarity	NPD5647	Approved
0.697	Remote Similarity	NPD2798	Approved
0.697	Remote Similarity	NPD6584	Phase 3
0.6966	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8032	Phase 2
0.6963	Remote Similarity	NPD6233	Phase 2
0.696	Remote Similarity	NPD709	Approved
0.696	Remote Similarity	NPD7157	Approved
0.6957	Remote Similarity	NPD2799	Discontinued
0.695	Remote Similarity	NPD4628	Phase 3
0.6949	Remote Similarity	NPD6647	Phase 2
0.6947	Remote Similarity	NPD3225	Approved
0.6935	Remote Similarity	NPD1241	Discontinued
0.6935	Remote Similarity	NPD5283	Phase 1
0.6929	Remote Similarity	NPD1548	Phase 1
0.6923	Remote Similarity	NPD1242	Phase 1
0.6912	Remote Similarity	NPD2203	Discontinued
0.6911	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1139	Approved
0.6911	Remote Similarity	NPD1137	Approved
0.6909	Remote Similarity	NPD1087	Approved
0.6905	Remote Similarity	NPD9568	Approved
0.6894	Remote Similarity	NPD1164	Approved
0.6894	Remote Similarity	NPD1470	Approved
0.6894	Remote Similarity	NPD3094	Phase 2
0.6894	Remote Similarity	NPD3267	Approved
0.6894	Remote Similarity	NPD3266	Approved
0.6889	Remote Similarity	NPD1048	Approved
0.6889	Remote Similarity	NPD2313	Discontinued
0.6889	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3764	Approved
0.6885	Remote Similarity	NPD2067	Discontinued
0.6884	Remote Similarity	NPD5688	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