NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	272.862
LogP:	2.628
LogD:	2.684
LogS:	-4.06
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	3.762
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.449
MDCK Permeability:	2.0630890503525734e-05
Pgp-inhibitor:	0.872
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.361
Plasma Protein Binding (PPB):	86.80601501464844%
Volume Distribution (VD):	1.669
Pgp-substrate:	13.292142868041992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.716
CYP2C9-substrate:	0.753
CYP2D6-inhibitor:	0.956
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.523

ADMET: Excretion

Clearance (CL):	3.616
Half-life (T1/2):	0.672

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.833
Drug-inuced Liver Injury (DILI):	0.477
AMES Toxicity:	0.933
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.532
Carcinogencity:	0.908
Eye Corrosion:	0.032
Eye Irritation:	0.874
Respiratory Toxicity:	0.545

Download Data

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

Natural Product: NPC211164

Natural Product ID:	NPC211164
*Common Name:**	Eupatobenzofuran
IUPAC Name:	[(2S,3R)-3-hydroxy-3,6-dimethyl-2H-1-benzofuran-2-yl] (Z)-2-methylbut-2-enoate
Synonyms:	Eupatobenzofuran
Standard InCHIKey:	QBRJXXZJFOHOGJ-KJUPGIGJSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-5-10(3)13(16)19-14-15(4,17)11-7-6-9(2)8-12(11)18-14/h5-8,14,17H,1-4H3/b10-5-/t14-,15+/m0/s1
SMILES:	C/C=C(/C)C(=O)O[C@H]1[C@@](C)(c2ccc(C)cc2O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795987
PubChem CID:	53262898
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans

*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	=	37.1	%	PMID[505520]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11300.0	nM	PMID[505520]

☑ 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 NPC211164 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	280
0.1-0.2	1336
0.2-0.3	3476
0.3-0.4	8643
0.4-0.5	10308
0.5-0.6	4127
0.6-0.7	11045
0.7-0.8	3439
0.8-0.85	39
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8779	High Similarity	NPC329272
0.876	High Similarity	NPC327070
0.876	High Similarity	NPC325301
0.8561	High Similarity	NPC183781
0.8527	High Similarity	NPC328485
0.8462	Intermediate Similarity	NPC322569
0.845	Intermediate Similarity	NPC98748
0.8421	Intermediate Similarity	NPC170749
0.837	Intermediate Similarity	NPC146540
0.8308	Intermediate Similarity	NPC160235
0.8288	Intermediate Similarity	NPC169510
0.8255	Intermediate Similarity	NPC469699
0.8219	Intermediate Similarity	NPC296377
0.8214	Intermediate Similarity	NPC185778
0.8203	Intermediate Similarity	NPC41851
0.8194	Intermediate Similarity	NPC242756
0.8168	Intermediate Similarity	NPC38181
0.8168	Intermediate Similarity	NPC20230
0.8162	Intermediate Similarity	NPC473993
0.8162	Intermediate Similarity	NPC469386
0.8134	Intermediate Similarity	NPC477152
0.8133	Intermediate Similarity	NPC34965
0.8133	Intermediate Similarity	NPC183536
0.8125	Intermediate Similarity	NPC469564
0.8125	Intermediate Similarity	NPC145319
0.8099	Intermediate Similarity	NPC134260
0.8092	Intermediate Similarity	NPC329980
0.8085	Intermediate Similarity	NPC33986
0.8082	Intermediate Similarity	NPC476450
0.8082	Intermediate Similarity	NPC85624
0.8079	Intermediate Similarity	NPC470331
0.8067	Intermediate Similarity	NPC470264
0.806	Intermediate Similarity	NPC188997
0.8056	Intermediate Similarity	NPC215512
0.8056	Intermediate Similarity	NPC476442
0.8043	Intermediate Similarity	NPC97326
0.8042	Intermediate Similarity	NPC151946
0.8028	Intermediate Similarity	NPC115861
0.8028	Intermediate Similarity	NPC166180
0.8028	Intermediate Similarity	NPC37468
0.8027	Intermediate Similarity	NPC199928
0.8015	Intermediate Similarity	NPC470510
0.8015	Intermediate Similarity	NPC85830
0.8014	Intermediate Similarity	NPC98179
0.8014	Intermediate Similarity	NPC253574
0.8014	Intermediate Similarity	NPC292443
0.8	Intermediate Similarity	NPC329427
0.8	Intermediate Similarity	NPC261992
0.8	Intermediate Similarity	NPC317601
0.8	Intermediate Similarity	NPC248786
0.7986	Intermediate Similarity	NPC325003
0.7985	Intermediate Similarity	NPC226712
0.7974	Intermediate Similarity	NPC228357
0.7973	Intermediate Similarity	NPC87950
0.7973	Intermediate Similarity	NPC471764
0.7972	Intermediate Similarity	NPC155963
0.7971	Intermediate Similarity	NPC81261
0.7971	Intermediate Similarity	NPC40377
0.797	Intermediate Similarity	NPC193193
0.797	Intermediate Similarity	NPC14177
0.797	Intermediate Similarity	NPC31314
0.7959	Intermediate Similarity	NPC138915
0.7959	Intermediate Similarity	NPC163898
0.7943	Intermediate Similarity	NPC469449
0.7933	Intermediate Similarity	NPC88886
0.7933	Intermediate Similarity	NPC104172
0.7931	Intermediate Similarity	NPC152771
0.7931	Intermediate Similarity	NPC210192
0.7931	Intermediate Similarity	NPC195357
0.7926	Intermediate Similarity	NPC132518
0.7926	Intermediate Similarity	NPC477151
0.7926	Intermediate Similarity	NPC302211
0.7919	Intermediate Similarity	NPC83975
0.7919	Intermediate Similarity	NPC236166
0.7919	Intermediate Similarity	NPC92054
0.7919	Intermediate Similarity	NPC93924
0.7919	Intermediate Similarity	NPC140722
0.7919	Intermediate Similarity	NPC4958
0.7917	Intermediate Similarity	NPC226005
0.7917	Intermediate Similarity	NPC100389
0.791	Intermediate Similarity	NPC475529
0.7907	Intermediate Similarity	NPC26615
0.7907	Intermediate Similarity	NPC280760
0.7902	Intermediate Similarity	NPC38099
0.7902	Intermediate Similarity	NPC475628
0.7902	Intermediate Similarity	NPC26954
0.7902	Intermediate Similarity	NPC471872
0.7902	Intermediate Similarity	NPC126101
0.7902	Intermediate Similarity	NPC103409
0.7902	Intermediate Similarity	NPC154485
0.7902	Intermediate Similarity	NPC186418
0.7899	Intermediate Similarity	NPC95034
0.7899	Intermediate Similarity	NPC142087
0.7895	Intermediate Similarity	NPC308739
0.7895	Intermediate Similarity	NPC126405
0.7895	Intermediate Similarity	NPC297271
0.7895	Intermediate Similarity	NPC57501
0.7895	Intermediate Similarity	NPC16791
0.7895	Intermediate Similarity	NPC53669
0.7895	Intermediate Similarity	NPC77237
0.7895	Intermediate Similarity	NPC37858
0.7895	Intermediate Similarity	NPC217708
0.7895	Intermediate Similarity	NPC472593
0.7891	Intermediate Similarity	NPC232228
0.7887	Intermediate Similarity	NPC34456
0.7887	Intermediate Similarity	NPC307412
0.7887	Intermediate Similarity	NPC50896
0.7887	Intermediate Similarity	NPC204353
0.7887	Intermediate Similarity	NPC264956
0.7887	Intermediate Similarity	NPC55149
0.7887	Intermediate Similarity	NPC62366
0.7887	Intermediate Similarity	NPC326600
0.7877	Intermediate Similarity	NPC31081
0.7877	Intermediate Similarity	NPC164599
0.7877	Intermediate Similarity	NPC245219
0.7872	Intermediate Similarity	NPC269421
0.7872	Intermediate Similarity	NPC2190
0.7871	Intermediate Similarity	NPC478269
0.7871	Intermediate Similarity	NPC241600
0.7871	Intermediate Similarity	NPC173726
0.7862	Intermediate Similarity	NPC312881
0.7857	Intermediate Similarity	NPC11089
0.7857	Intermediate Similarity	NPC275950
0.7857	Intermediate Similarity	NPC262606
0.7857	Intermediate Similarity	NPC474491
0.7857	Intermediate Similarity	NPC473323
0.7852	Intermediate Similarity	NPC41844
0.7852	Intermediate Similarity	NPC114845
0.7852	Intermediate Similarity	NPC476165
0.7852	Intermediate Similarity	NPC469700
0.7847	Intermediate Similarity	NPC477534
0.7847	Intermediate Similarity	NPC184861
0.7847	Intermediate Similarity	NPC232246
0.7847	Intermediate Similarity	NPC20796
0.7847	Intermediate Similarity	NPC153818
0.7847	Intermediate Similarity	NPC281014
0.7847	Intermediate Similarity	NPC212124
0.7847	Intermediate Similarity	NPC294456
0.7847	Intermediate Similarity	NPC225106
0.7846	Intermediate Similarity	NPC190212
0.7843	Intermediate Similarity	NPC198461
0.7838	Intermediate Similarity	NPC226722
0.7832	Intermediate Similarity	NPC51087
0.7832	Intermediate Similarity	NPC161856
0.7832	Intermediate Similarity	NPC472525
0.7832	Intermediate Similarity	NPC291119
0.7832	Intermediate Similarity	NPC281169
0.7829	Intermediate Similarity	NPC302610
0.7829	Intermediate Similarity	NPC176186
0.7829	Intermediate Similarity	NPC169404
0.7829	Intermediate Similarity	NPC476452
0.7829	Intermediate Similarity	NPC53587
0.7826	Intermediate Similarity	NPC474476
0.7823	Intermediate Similarity	NPC478239
0.782	Intermediate Similarity	NPC206205
0.782	Intermediate Similarity	NPC283616
0.7817	Intermediate Similarity	NPC472591
0.7817	Intermediate Similarity	NPC25821
0.7817	Intermediate Similarity	NPC222036
0.7817	Intermediate Similarity	NPC163557
0.7817	Intermediate Similarity	NPC7526
0.781	Intermediate Similarity	NPC20443
0.781	Intermediate Similarity	NPC60517
0.781	Intermediate Similarity	NPC146886
0.781	Intermediate Similarity	NPC147896
0.781	Intermediate Similarity	NPC469568
0.7808	Intermediate Similarity	NPC287286
0.7808	Intermediate Similarity	NPC477537
0.7808	Intermediate Similarity	NPC186406
0.7806	Intermediate Similarity	NPC475592
0.7803	Intermediate Similarity	NPC33717
0.7801	Intermediate Similarity	NPC29734
0.7801	Intermediate Similarity	NPC324488
0.7801	Intermediate Similarity	NPC166168
0.7801	Intermediate Similarity	NPC476345
0.78	Intermediate Similarity	NPC474795
0.78	Intermediate Similarity	NPC474940
0.78	Intermediate Similarity	NPC130959
0.78	Intermediate Similarity	NPC469425
0.78	Intermediate Similarity	NPC159697
0.78	Intermediate Similarity	NPC96294
0.78	Intermediate Similarity	NPC303013
0.7793	Intermediate Similarity	NPC211110
0.7793	Intermediate Similarity	NPC279573
0.7792	Intermediate Similarity	NPC476065
0.7786	Intermediate Similarity	NPC295970
0.7778	Intermediate Similarity	NPC327735
0.7778	Intermediate Similarity	NPC157554
0.7778	Intermediate Similarity	NPC188380
0.7778	Intermediate Similarity	NPC204466
0.7778	Intermediate Similarity	NPC92932
0.7778	Intermediate Similarity	NPC96423
0.7778	Intermediate Similarity	NPC24562
0.7778	Intermediate Similarity	NPC150442
0.7778	Intermediate Similarity	NPC224543
0.7778	Intermediate Similarity	NPC78746
0.7771	Intermediate Similarity	NPC478267
0.777	Intermediate Similarity	NPC110063
0.777	Intermediate Similarity	NPC471763
0.777	Intermediate Similarity	NPC64948

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 NPC211164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	832
0.2-0.3	1742
0.3-0.4	2596
0.4-0.5	1900
0.5-0.6	1139
0.6-0.7	594
0.7-0.8	100
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
0.8045	Intermediate Similarity	NPD3496	Discontinued
0.7985	Intermediate Similarity	NPD1091	Approved
0.7836	Intermediate Similarity	NPD1778	Approved
0.7836	Intermediate Similarity	NPD4626	Approved
0.7762	Intermediate Similarity	NPD6653	Approved
0.7761	Intermediate Similarity	NPD5691	Approved
0.7748	Intermediate Similarity	NPD1653	Approved
0.7746	Intermediate Similarity	NPD4060	Phase 1
0.7692	Intermediate Similarity	NPD447	Suspended
0.7635	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2797	Approved
0.7606	Intermediate Similarity	NPD411	Approved
0.7569	Intermediate Similarity	NPD6355	Discontinued
0.7561	Intermediate Similarity	NPD6559	Discontinued
0.7551	Intermediate Similarity	NPD5762	Approved
0.7551	Intermediate Similarity	NPD5763	Approved
0.7536	Intermediate Similarity	NPD9717	Approved
0.7535	Intermediate Similarity	NPD7095	Approved
0.7534	Intermediate Similarity	NPD4308	Phase 3
0.7519	Intermediate Similarity	NPD290	Approved
0.7519	Intermediate Similarity	NPD1358	Approved
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD2424	Discontinued
0.7483	Intermediate Similarity	NPD3268	Approved
0.7464	Intermediate Similarity	NPD1611	Approved
0.7463	Intermediate Similarity	NPD6671	Approved
0.7424	Intermediate Similarity	NPD969	Suspended
0.7372	Intermediate Similarity	NPD1357	Approved
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6032	Approved
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7361	Intermediate Similarity	NPD6798	Discontinued
0.7361	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7985	Registered
0.7357	Intermediate Similarity	NPD4749	Approved
0.7355	Intermediate Similarity	NPD7458	Discontinued
0.7355	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7097	Phase 1
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7338	Intermediate Similarity	NPD3705	Approved
0.7333	Intermediate Similarity	NPD6674	Discontinued
0.7333	Intermediate Similarity	NPD7157	Approved
0.7329	Intermediate Similarity	NPD7199	Phase 2
0.7328	Intermediate Similarity	NPD2684	Approved
0.7325	Intermediate Similarity	NPD37	Approved
0.732	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3818	Discontinued
0.7315	Intermediate Similarity	NPD6002	Phase 3
0.7315	Intermediate Similarity	NPD6004	Phase 3
0.7315	Intermediate Similarity	NPD6005	Phase 3
0.7315	Intermediate Similarity	NPD7266	Discontinued
0.7315	Intermediate Similarity	NPD2346	Discontinued
0.7315	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6234	Discontinued
0.7305	Intermediate Similarity	NPD6696	Suspended
0.7296	Intermediate Similarity	NPD4967	Phase 2
0.7296	Intermediate Similarity	NPD4965	Approved
0.7296	Intermediate Similarity	NPD4966	Approved
0.7285	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2237	Approved
0.7262	Intermediate Similarity	NPD8313	Approved
0.7262	Intermediate Similarity	NPD8312	Approved
0.726	Intermediate Similarity	NPD4307	Phase 2
0.7254	Intermediate Similarity	NPD1203	Approved
0.7254	Intermediate Similarity	NPD987	Approved
0.725	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1551	Phase 2
0.7246	Intermediate Similarity	NPD5585	Approved
0.7241	Intermediate Similarity	NPD1048	Approved
0.7241	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7843	Approved
0.7239	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD9697	Approved
0.7222	Intermediate Similarity	NPD6832	Phase 2
0.7219	Intermediate Similarity	NPD1652	Phase 2
0.7211	Intermediate Similarity	NPD1933	Approved
0.7211	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2534	Approved
0.7208	Intermediate Similarity	NPD2532	Approved
0.7208	Intermediate Similarity	NPD2533	Approved
0.7208	Intermediate Similarity	NPD1578	Phase 2
0.7203	Intermediate Similarity	NPD1019	Discontinued
0.7203	Intermediate Similarity	NPD5647	Approved
0.72	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6599	Discontinued
0.7192	Intermediate Similarity	NPD6233	Phase 2
0.7183	Intermediate Similarity	NPD3225	Approved
0.7181	Intermediate Similarity	NPD7033	Discontinued
0.7176	Intermediate Similarity	NPD3134	Approved
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7171	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4110	Phase 3
0.717	Intermediate Similarity	NPD8455	Phase 2
0.7163	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4140	Approved
0.7133	Intermediate Similarity	NPD6362	Approved
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD3267	Approved
0.7123	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7228	Approved
0.7103	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5124	Phase 1
0.7095	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2799	Discontinued
0.7066	Intermediate Similarity	NPD5844	Phase 1
0.7063	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1398	Phase 1
0.7055	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2676	Approved
0.7051	Intermediate Similarity	NPD2675	Approved
0.7037	Intermediate Similarity	NPD228	Approved
0.7034	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1712	Approved
0.7034	Intermediate Similarity	NPD2861	Phase 2
0.7032	Intermediate Similarity	NPD6799	Approved
0.7029	Intermediate Similarity	NPD9493	Approved
0.7027	Intermediate Similarity	NPD2203	Discontinued
0.7025	Intermediate Similarity	NPD3226	Approved
0.7024	Intermediate Similarity	NPD7074	Phase 3
0.702	Intermediate Similarity	NPD6100	Approved
0.702	Intermediate Similarity	NPD6099	Approved
0.7019	Intermediate Similarity	NPD5402	Approved
0.7007	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2313	Discontinued
0.7006	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4359	Approved
0.6993	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4908	Phase 1
0.6985	Remote Similarity	NPD5535	Approved
0.6985	Remote Similarity	NPD1138	Approved
0.6981	Remote Similarity	NPD7028	Phase 2
0.6978	Remote Similarity	NPD7644	Approved
0.6977	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3882	Suspended
0.6974	Remote Similarity	NPD1375	Discontinued
0.6972	Remote Similarity	NPD1610	Phase 2
0.6968	Remote Similarity	NPD5058	Phase 3
0.6966	Remote Similarity	NPD2798	Approved
0.6966	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7054	Approved
0.6959	Remote Similarity	NPD4062	Phase 3
0.6957	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7819	Suspended
0.6957	Remote Similarity	NPD4198	Discontinued
0.695	Remote Similarity	NPD17	Approved
0.6948	Remote Similarity	NPD3750	Approved
0.6943	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6273	Approved
0.6939	Remote Similarity	NPD3027	Phase 3
0.6934	Remote Similarity	NPD1241	Discontinued
0.6933	Remote Similarity	NPD7075	Discontinued
0.6928	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7472	Approved
0.6917	Remote Similarity	NPD968	Approved
0.6914	Remote Similarity	NPD3817	Phase 2
0.6913	Remote Similarity	NPD2979	Phase 3
0.6912	Remote Similarity	NPD1139	Approved
0.6912	Remote Similarity	NPD1137	Approved
0.6909	Remote Similarity	NPD8127	Discontinued
0.6908	Remote Similarity	NPD2438	Suspended
0.6906	Remote Similarity	NPD7340	Approved
0.6905	Remote Similarity	NPD3751	Discontinued
0.6901	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5403	Approved
0.6894	Remote Similarity	NPD1934	Approved
0.6892	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6797	Phase 2
0.6875	Remote Similarity	NPD844	Approved
0.6867	Remote Similarity	NPD4340	Discontinued
0.6867	Remote Similarity	NPD230	Phase 1
0.6864	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5536	Phase 2
0.6853	Remote Similarity	NPD1535	Discovery
0.6853	Remote Similarity	NPD1281	Approved
0.6853	Remote Similarity	NPD776	Approved
0.6852	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD558	Phase 2
0.6842	Remote Similarity	NPD7240	Approved
0.6842	Remote Similarity	NPD7251	Discontinued
0.6842	Remote Similarity	NPD7685	Pre-registration
0.6839	Remote Similarity	NPD7003	Approved
0.6835	Remote Similarity	NPD709	Approved
0.6831	Remote Similarity	NPD5125	Phase 3
0.6831	Remote Similarity	NPD5126	Approved
0.6828	Remote Similarity	NPD8651	Approved
0.6822	Remote Similarity	NPD288	Approved
0.6818	Remote Similarity	NPD4534	Discontinued
0.6818	Remote Similarity	NPD5958	Discontinued
0.6813	Remote Similarity	NPD3111	Phase 1
0.6812	Remote Similarity	NPD5283	Phase 1

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