NPASS Compound

Structure

CID322569 OpenBabel06191716162D 21 21 0 0 1 0 0 0 0 0999 V2000 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 16 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	313.374
LogP:	3.456
LogD:	3.798
LogS:	-3.663
# Rotatable Bonds:	7
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	2.986
Fsp3:	0.412
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:	-4.764
MDCK Permeability:	2.163984754588455e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.756
Plasma Protein Binding (PPB):	92.43000030517578%
Volume Distribution (VD):	0.603
Pgp-substrate:	17.111440658569336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.741
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.62
CYP2D6-inhibitor:	0.85
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.598

ADMET: Excretion

Clearance (CL):	5.583
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.33
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.3
Skin Sensitization:	0.934
Carcinogencity:	0.288
Eye Corrosion:	0.019
Eye Irritation:	0.842
Respiratory Toxicity:	0.572

Download Data

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

Natural Product: NPC322569

Natural Product ID:	NPC322569
*Common Name:**	9-Acetoxythymol 3-O-Tiglate
IUPAC Name:	[2-(1-acetyloxypropan-2-yl)-5-methylphenyl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	NZQYJWRRXAUWML-WUXMJOGZSA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-6-12(3)17(19)21-16-9-11(2)7-8-15(16)13(4)10-20-14(5)18/h6-9,13H,10H2,1-5H3/b12-6+
SMILES:	CC=C(C)C(=O)OC1=C(C=CC(=C1)C)C(C)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795992
PubChem CID:	11808409
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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]
NPO21343	Eupatorium fortunei	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]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21343	Eupatorium fortunei	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[TCM_Taiwan]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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.	IC50	=	18400.0	nM	PMID[459600]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	21.6	%	PMID[459600]

☑ 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 NPC322569 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	279
0.1-0.2	1498
0.2-0.3	3851
0.3-0.4	10421
0.4-0.5	8462
0.5-0.6	5165
0.6-0.7	11194
0.7-0.8	1742
0.8-0.85	76
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9823	High Similarity	NPC98748
0.9333	High Similarity	NPC329272
0.9204	High Similarity	NPC280760
0.9091	High Similarity	NPC170749
0.8718	High Similarity	NPC87563
0.8689	High Similarity	NPC476332
0.8689	High Similarity	NPC473464
0.8571	High Similarity	NPC81261
0.8559	High Similarity	NPC41851
0.8537	High Similarity	NPC325301
0.8462	Intermediate Similarity	NPC211164
0.8443	Intermediate Similarity	NPC14177
0.8435	Intermediate Similarity	NPC151530
0.8435	Intermediate Similarity	NPC157473
0.8407	Intermediate Similarity	NPC12870
0.8407	Intermediate Similarity	NPC24327
0.839	Intermediate Similarity	NPC26615
0.8387	Intermediate Similarity	NPC327070
0.8376	Intermediate Similarity	NPC473809
0.8361	Intermediate Similarity	NPC234956
0.8358	Intermediate Similarity	NPC472523
0.8348	Intermediate Similarity	NPC30416
0.8348	Intermediate Similarity	NPC326447
0.8348	Intermediate Similarity	NPC176971
0.8319	Intermediate Similarity	NPC190212
0.8293	Intermediate Similarity	NPC31314
0.8293	Intermediate Similarity	NPC328485
0.8293	Intermediate Similarity	NPC473290
0.8293	Intermediate Similarity	NPC193193
0.8293	Intermediate Similarity	NPC471504
0.8291	Intermediate Similarity	NPC149545
0.8279	Intermediate Similarity	NPC293424
0.8279	Intermediate Similarity	NPC159916
0.8268	Intermediate Similarity	NPC128321
0.8268	Intermediate Similarity	NPC101894
0.8261	Intermediate Similarity	NPC128730
0.8261	Intermediate Similarity	NPC139891
0.8261	Intermediate Similarity	NPC473855
0.824	Intermediate Similarity	NPC188997
0.8203	Intermediate Similarity	NPC95034
0.8203	Intermediate Similarity	NPC142087
0.8203	Intermediate Similarity	NPC156298
0.8197	Intermediate Similarity	NPC471503
0.8197	Intermediate Similarity	NPC471498
0.8195	Intermediate Similarity	NPC115861
0.8189	Intermediate Similarity	NPC471827
0.8189	Intermediate Similarity	NPC471828
0.8175	Intermediate Similarity	NPC261992
0.8175	Intermediate Similarity	NPC248786
0.8175	Intermediate Similarity	NPC470887
0.8174	Intermediate Similarity	NPC283546
0.8168	Intermediate Similarity	NPC317601
0.8168	Intermediate Similarity	NPC329427
0.816	Intermediate Similarity	NPC476165
0.8154	Intermediate Similarity	NPC249425
0.8148	Intermediate Similarity	NPC476191
0.814	Intermediate Similarity	NPC176590
0.814	Intermediate Similarity	NPC472519
0.812	Intermediate Similarity	NPC281241
0.812	Intermediate Similarity	NPC471625
0.812	Intermediate Similarity	NPC472424
0.812	Intermediate Similarity	NPC471909
0.812	Intermediate Similarity	NPC86892
0.8115	Intermediate Similarity	NPC163398
0.8115	Intermediate Similarity	NPC33717
0.811	Intermediate Similarity	NPC73413
0.811	Intermediate Similarity	NPC147896
0.811	Intermediate Similarity	NPC27671
0.811	Intermediate Similarity	NPC201667
0.811	Intermediate Similarity	NPC89630
0.811	Intermediate Similarity	NPC474237
0.8103	Intermediate Similarity	NPC288760
0.8103	Intermediate Similarity	NPC227255
0.8092	Intermediate Similarity	NPC470977
0.8092	Intermediate Similarity	NPC470976
0.8092	Intermediate Similarity	NPC196979
0.8087	Intermediate Similarity	NPC179686
0.8083	Intermediate Similarity	NPC199462
0.808	Intermediate Similarity	NPC267064
0.808	Intermediate Similarity	NPC235190
0.808	Intermediate Similarity	NPC180006
0.808	Intermediate Similarity	NPC163200
0.8077	Intermediate Similarity	NPC168710
0.8067	Intermediate Similarity	NPC231251
0.8067	Intermediate Similarity	NPC88868
0.8067	Intermediate Similarity	NPC25067
0.8065	Intermediate Similarity	NPC160235
0.8065	Intermediate Similarity	NPC37858
0.8062	Intermediate Similarity	NPC473993
0.806	Intermediate Similarity	NPC160727
0.806	Intermediate Similarity	NPC55615
0.806	Intermediate Similarity	NPC476455
0.806	Intermediate Similarity	NPC283019
0.806	Intermediate Similarity	NPC177281
0.806	Intermediate Similarity	NPC149320
0.806	Intermediate Similarity	NPC128529
0.806	Intermediate Similarity	NPC471630
0.8051	Intermediate Similarity	NPC291837
0.8049	Intermediate Similarity	NPC183154
0.8049	Intermediate Similarity	NPC238075
0.8049	Intermediate Similarity	NPC263754
0.8045	Intermediate Similarity	NPC198381
0.8045	Intermediate Similarity	NPC18804
0.8045	Intermediate Similarity	NPC287182
0.8045	Intermediate Similarity	NPC164269
0.8045	Intermediate Similarity	NPC127888
0.8045	Intermediate Similarity	NPC319859
0.8045	Intermediate Similarity	NPC55149
0.8045	Intermediate Similarity	NPC260265
0.8045	Intermediate Similarity	NPC307412
0.8045	Intermediate Similarity	NPC267412
0.8045	Intermediate Similarity	NPC84894
0.8045	Intermediate Similarity	NPC74655
0.8045	Intermediate Similarity	NPC195343
0.8045	Intermediate Similarity	NPC166672
0.8045	Intermediate Similarity	NPC100986
0.8045	Intermediate Similarity	NPC47163
0.8031	Intermediate Similarity	NPC109675
0.8031	Intermediate Similarity	NPC273772
0.8031	Intermediate Similarity	NPC320287
0.8031	Intermediate Similarity	NPC472518
0.8029	Intermediate Similarity	NPC469564
0.8017	Intermediate Similarity	NPC303522
0.8015	Intermediate Similarity	NPC183348
0.8015	Intermediate Similarity	NPC282230
0.8015	Intermediate Similarity	NPC80170
0.8015	Intermediate Similarity	NPC19242
0.8	Intermediate Similarity	NPC230951
0.8	Intermediate Similarity	NPC306365
0.8	Intermediate Similarity	NPC199204
0.8	Intermediate Similarity	NPC131198
0.8	Intermediate Similarity	NPC474874
0.8	Intermediate Similarity	NPC14697
0.8	Intermediate Similarity	NPC307425
0.8	Intermediate Similarity	NPC84325
0.7985	Intermediate Similarity	NPC281169
0.7985	Intermediate Similarity	NPC291119
0.7984	Intermediate Similarity	NPC127604
0.7984	Intermediate Similarity	NPC171023
0.7984	Intermediate Similarity	NPC124916
0.7984	Intermediate Similarity	NPC277460
0.797	Intermediate Similarity	NPC222036
0.797	Intermediate Similarity	NPC133956
0.797	Intermediate Similarity	NPC472524
0.797	Intermediate Similarity	NPC296624
0.797	Intermediate Similarity	NPC472591
0.797	Intermediate Similarity	NPC7526
0.797	Intermediate Similarity	NPC471910
0.797	Intermediate Similarity	NPC167111
0.797	Intermediate Similarity	NPC233018
0.797	Intermediate Similarity	NPC241341
0.797	Intermediate Similarity	NPC36437
0.797	Intermediate Similarity	NPC207002
0.797	Intermediate Similarity	NPC31849
0.797	Intermediate Similarity	NPC318400
0.7969	Intermediate Similarity	NPC469568
0.7969	Intermediate Similarity	NPC470163
0.7969	Intermediate Similarity	NPC190086
0.7969	Intermediate Similarity	NPC56332
0.7969	Intermediate Similarity	NPC470162
0.7969	Intermediate Similarity	NPC276962
0.7967	Intermediate Similarity	NPC128633
0.7955	Intermediate Similarity	NPC15083
0.7953	Intermediate Similarity	NPC248429
0.7953	Intermediate Similarity	NPC302211
0.7953	Intermediate Similarity	NPC132518
0.7953	Intermediate Similarity	NPC477151
0.7953	Intermediate Similarity	NPC96286
0.7949	Intermediate Similarity	NPC473393
0.7941	Intermediate Similarity	NPC307883
0.7939	Intermediate Similarity	NPC170546
0.7939	Intermediate Similarity	NPC66246
0.7939	Intermediate Similarity	NPC271832
0.7937	Intermediate Similarity	NPC212559
0.7923	Intermediate Similarity	NPC474670
0.7923	Intermediate Similarity	NPC161322
0.792	Intermediate Similarity	NPC51341
0.792	Intermediate Similarity	NPC264976
0.792	Intermediate Similarity	NPC298796
0.792	Intermediate Similarity	NPC471449
0.792	Intermediate Similarity	NPC281356
0.7913	Intermediate Similarity	NPC107101
0.791	Intermediate Similarity	NPC27394
0.7907	Intermediate Similarity	NPC232387
0.7899	Intermediate Similarity	NPC20631
0.7899	Intermediate Similarity	NPC93640
0.7895	Intermediate Similarity	NPC14248
0.7895	Intermediate Similarity	NPC19157
0.7895	Intermediate Similarity	NPC137669
0.7895	Intermediate Similarity	NPC319969
0.7895	Intermediate Similarity	NPC470161
0.7891	Intermediate Similarity	NPC21238
0.7891	Intermediate Similarity	NPC279379
0.7891	Intermediate Similarity	NPC315807
0.7886	Intermediate Similarity	NPC283169
0.7883	Intermediate Similarity	NPC475012
0.7881	Intermediate Similarity	NPC326801
0.7879	Intermediate Similarity	NPC2989
0.7874	Intermediate Similarity	NPC114845
0.7874	Intermediate Similarity	NPC475839

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 NPC322569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	1002
0.2-0.3	1467
0.3-0.4	2587
0.4-0.5	1869
0.5-0.6	1214
0.6-0.7	617
0.7-0.8	124
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD5691	Approved
0.8678	High Similarity	NPD3496	Discontinued
0.8492	Intermediate Similarity	NPD2237	Approved
0.8455	Intermediate Similarity	NPD1611	Approved
0.8443	Intermediate Similarity	NPD4626	Approved
0.8361	Intermediate Similarity	NPD5585	Approved
0.8348	Intermediate Similarity	NPD3134	Approved
0.8293	Intermediate Similarity	NPD1778	Approved
0.8261	Intermediate Similarity	NPD9697	Approved
0.812	Intermediate Similarity	NPD1358	Approved
0.8083	Intermediate Similarity	NPD5535	Approved
0.8049	Intermediate Similarity	NPD7644	Approved
0.8047	Intermediate Similarity	NPD3267	Approved
0.8047	Intermediate Similarity	NPD3266	Approved
0.8047	Intermediate Similarity	NPD2797	Approved
0.8031	Intermediate Similarity	NPD4359	Approved
0.8	Intermediate Similarity	NPD6832	Phase 2
0.797	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4060	Phase 1
0.7895	Intermediate Similarity	NPD4307	Phase 2
0.7895	Intermediate Similarity	NPD2979	Phase 3
0.7879	Intermediate Similarity	NPD3268	Approved
0.7857	Intermediate Similarity	NPD17	Approved
0.7846	Intermediate Similarity	NPD1019	Discontinued
0.781	Intermediate Similarity	NPD2346	Discontinued
0.777	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD4140	Approved
0.7744	Intermediate Similarity	NPD411	Approved
0.7744	Intermediate Similarity	NPD7985	Registered
0.7742	Intermediate Similarity	NPD6671	Approved
0.7734	Intermediate Similarity	NPD1281	Approved
0.7724	Intermediate Similarity	NPD1241	Discontinued
0.7704	Intermediate Similarity	NPD6355	Discontinued
0.7687	Intermediate Similarity	NPD8032	Phase 2
0.7687	Intermediate Similarity	NPD4870	Approved
0.7681	Intermediate Similarity	NPD5763	Approved
0.7681	Intermediate Similarity	NPD5762	Approved
0.7674	Intermediate Similarity	NPD1608	Approved
0.7674	Intermediate Similarity	NPD9717	Approved
0.7664	Intermediate Similarity	NPD2799	Discontinued
0.7664	Intermediate Similarity	NPD4308	Phase 3
0.7647	Intermediate Similarity	NPD6653	Approved
0.7609	Intermediate Similarity	NPD6032	Approved
0.7603	Intermediate Similarity	NPD2684	Approved
0.76	Intermediate Similarity	NPD7157	Approved
0.7586	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD5283	Phase 1
0.7574	Intermediate Similarity	NPD447	Suspended
0.7574	Intermediate Similarity	NPD4618	Approved
0.7574	Intermediate Similarity	NPD4622	Approved
0.7557	Intermediate Similarity	NPD1283	Approved
0.7554	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD7095	Approved
0.7518	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD6362	Approved
0.75	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD1651	Approved
0.7482	Intermediate Similarity	NPD2531	Phase 2
0.7482	Intermediate Similarity	NPD2438	Suspended
0.7482	Intermediate Similarity	NPD2935	Discontinued
0.7481	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6798	Discontinued
0.7481	Intermediate Similarity	NPD2313	Discontinued
0.7481	Intermediate Similarity	NPD4749	Approved
0.7481	Intermediate Similarity	NPD5327	Phase 3
0.748	Intermediate Similarity	NPD5536	Phase 2
0.7466	Intermediate Similarity	NPD3226	Approved
0.7464	Intermediate Similarity	NPD5689	Approved
0.7464	Intermediate Similarity	NPD5688	Approved
0.7462	Intermediate Similarity	NPD422	Phase 1
0.7462	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2798	Approved
0.7431	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6004	Phase 3
0.7429	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6005	Phase 3
0.7429	Intermediate Similarity	NPD6002	Phase 3
0.7424	Intermediate Similarity	NPD3225	Approved
0.7419	Intermediate Similarity	NPD1137	Approved
0.7419	Intermediate Similarity	NPD1139	Approved
0.7405	Intermediate Similarity	NPD3972	Approved
0.7394	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4110	Phase 3
0.7388	Intermediate Similarity	NPD2861	Phase 2
0.7379	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2676	Approved
0.7379	Intermediate Similarity	NPD2675	Approved
0.7377	Intermediate Similarity	NPD290	Approved
0.7368	Intermediate Similarity	NPD1203	Approved
0.7364	Intermediate Similarity	NPD3444	Approved
0.7364	Intermediate Similarity	NPD3443	Approved
0.7364	Intermediate Similarity	NPD3445	Approved
0.736	Intermediate Similarity	NPD1138	Approved
0.7353	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7097	Phase 1
0.7333	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2614	Approved
0.7324	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2557	Approved
0.7319	Intermediate Similarity	NPD5124	Phase 1
0.7319	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1578	Phase 2
0.7293	Intermediate Similarity	NPD6696	Suspended
0.7287	Intermediate Similarity	NPD1894	Discontinued
0.7286	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD7003	Approved
0.7266	Intermediate Similarity	NPD2653	Approved
0.7266	Intermediate Similarity	NPD7340	Approved
0.7259	Intermediate Similarity	NPD1712	Approved
0.7252	Intermediate Similarity	NPD3847	Discontinued
0.7246	Intermediate Similarity	NPD2203	Discontinued
0.7241	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD987	Approved
0.7234	Intermediate Similarity	NPD4477	Approved
0.7234	Intermediate Similarity	NPD4476	Approved
0.7234	Intermediate Similarity	NPD1551	Phase 2
0.7226	Intermediate Similarity	NPD1296	Phase 2
0.7218	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8127	Discontinued
0.7206	Intermediate Similarity	NPD4908	Phase 1
0.7203	Intermediate Similarity	NPD288	Approved
0.7197	Intermediate Similarity	NPD3705	Approved
0.7194	Intermediate Similarity	NPD1933	Approved
0.7188	Intermediate Similarity	NPD6387	Discontinued
0.7185	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5647	Approved
0.7183	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6599	Discontinued
0.7177	Intermediate Similarity	NPD2182	Approved
0.7174	Intermediate Similarity	NPD6233	Phase 2
0.7172	Intermediate Similarity	NPD6666	Approved
0.7172	Intermediate Similarity	NPD6667	Approved
0.7165	Intermediate Similarity	NPD1398	Phase 1
0.7164	Intermediate Similarity	NPD1876	Approved
0.7163	Intermediate Similarity	NPD7033	Discontinued
0.7154	Intermediate Similarity	NPD968	Approved
0.7153	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7143	Intermediate Similarity	NPD2232	Approved
0.7143	Intermediate Similarity	NPD2233	Approved
0.7143	Intermediate Similarity	NPD2230	Approved
0.7133	Intermediate Similarity	NPD2897	Discontinued
0.7133	Intermediate Similarity	NPD2424	Discontinued
0.7119	Intermediate Similarity	NPD844	Approved
0.7114	Intermediate Similarity	NPD7458	Discontinued
0.7113	Intermediate Similarity	NPD2796	Approved
0.7113	Intermediate Similarity	NPD6100	Approved
0.7113	Intermediate Similarity	NPD6099	Approved
0.7101	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3049	Approved
0.709	Intermediate Similarity	NPD3685	Discontinued
0.709	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD821	Approved
0.7083	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1652	Phase 2
0.7075	Intermediate Similarity	NPD2534	Approved
0.7075	Intermediate Similarity	NPD2533	Approved
0.7075	Intermediate Similarity	NPD2532	Approved
0.7068	Intermediate Similarity	NPD1535	Discovery
0.7068	Intermediate Similarity	NPD1610	Phase 2
0.7063	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD709	Approved
0.705	Intermediate Similarity	NPD4062	Phase 3
0.7047	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5844	Phase 1
0.7037	Intermediate Similarity	NPD8651	Approved
0.7034	Intermediate Similarity	NPD3750	Approved
0.7031	Intermediate Similarity	NPD592	Approved
0.7031	Intermediate Similarity	NPD594	Approved
0.7029	Intermediate Similarity	NPD5163	Phase 2
0.7029	Intermediate Similarity	NPD5746	Approved
0.7027	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2157	Approved
0.7015	Intermediate Similarity	NPD1481	Phase 2
0.7014	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD3596	Phase 2
0.6993	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3887	Approved
0.6985	Remote Similarity	NPD4098	Discontinued
0.6984	Remote Similarity	NPD2067	Discontinued
0.6984	Remote Similarity	NPD5451	Approved
0.698	Remote Similarity	NPD920	Approved
0.6978	Remote Similarity	NPD1048	Approved
0.695	Remote Similarity	NPD5735	Approved
0.695	Remote Similarity	NPD4340	Discontinued
0.694	Remote Similarity	NPD1091	Approved
0.6934	Remote Similarity	NPD3691	Phase 2
0.6934	Remote Similarity	NPD3690	Phase 2

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