NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.14
Volume:	296.027
LogP:	4.189
LogD:	3.796
LogS:	-5.161
# Rotatable Bonds:	6
TPSA:	27.69
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	1.699
Fsp3:	0.294
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:	-4.759
MDCK Permeability:	2.13449038710678e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.496
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	97.45174407958984%
Volume Distribution (VD):	1.971
Pgp-substrate:	1.6658653020858765%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.769
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.909
CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.54

ADMET: Excretion

Clearance (CL):	10.658
Half-life (T1/2):	0.477

ADMET: Toxicity

hERG Blockers:	0.718
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.276
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.944
Carcinogencity:	0.041
Eye Corrosion:	0.445
Eye Irritation:	0.954
Respiratory Toxicity:	0.064

Download Data

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

Natural Product: NPC2682

Natural Product ID:	NPC2682
*Common Name:**	3,3',5-Trimethoxybibenzyl
IUPAC Name:	1,3-dimethoxy-5-[2-(3-methoxyphenyl)ethyl]benzene
Synonyms:	3,3',5-Trimethoxybibenzyl
Standard InCHIKey:	JKLWPFRFUHSWOA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O3/c1-18-15-6-4-5-13(9-15)7-8-14-10-16(19-2)12-17(11-14)20-3/h4-6,9-12H,7-8H2,1-3H3
SMILES:	COc1cccc(CCc2cc(cc(c2)OC)OC)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444998
PubChem CID:	15693460
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8787	Ariocarpus scapharostrus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15591	Tolpis webbii	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	2

Activity Type	# Activity
Tissue	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT548	Tissue	Ileum	Cavia porcellus	IC50	=	960.0	nM	PMID[533004]
NPT548	Tissue	Ileum	Cavia porcellus	Emax	=	75.57	%	PMID[533004]
NPT548	Tissue	Ileum	Cavia porcellus	Ratio IC50	=	4.41	n.a.	PMID[533004]

☑ 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 NPC2682 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	430
0.1-0.2	1941
0.2-0.3	5723
0.3-0.4	13561
0.4-0.5	3610
0.5-0.6	6521
0.6-0.7	8109
0.7-0.8	2366
0.8-0.85	331
0.85-0.9	66
0.9-0.95	33
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC35543
0.9615	High Similarity	NPC303521
0.9612	High Similarity	NPC245115
0.9533	High Similarity	NPC53906
0.9519	High Similarity	NPC82016
0.9439	High Similarity	NPC22610
0.9439	High Similarity	NPC276737
0.9358	High Similarity	NPC219070
0.9358	High Similarity	NPC15860
0.9358	High Similarity	NPC127894
0.9358	High Similarity	NPC33270
0.9358	High Similarity	NPC69261
0.9358	High Similarity	NPC474933
0.9358	High Similarity	NPC470759
0.9266	High Similarity	NPC114064
0.9266	High Similarity	NPC141090
0.9266	High Similarity	NPC150624
0.9189	High Similarity	NPC184302
0.9189	High Similarity	NPC475961
0.9189	High Similarity	NPC254625
0.9174	High Similarity	NPC808
0.9174	High Similarity	NPC167934
0.9099	High Similarity	NPC190514
0.9083	High Similarity	NPC228287
0.9083	High Similarity	NPC180508
0.9065	High Similarity	NPC94045
0.9065	High Similarity	NPC168657
0.9018	High Similarity	NPC15805
0.9009	High Similarity	NPC50521
0.9009	High Similarity	NPC244816
0.9009	High Similarity	NPC221549
0.9009	High Similarity	NPC195466
0.8947	High Similarity	NPC476633
0.8947	High Similarity	NPC477886
0.8919	High Similarity	NPC54507
0.8919	High Similarity	NPC123948
0.8919	High Similarity	NPC229147
0.8919	High Similarity	NPC85292
0.8899	High Similarity	NPC280606
0.887	High Similarity	NPC77789
0.887	High Similarity	NPC18128
0.886	High Similarity	NPC102639
0.886	High Similarity	NPC472596
0.8829	High Similarity	NPC185541
0.8829	High Similarity	NPC464
0.8818	High Similarity	NPC204120
0.8807	High Similarity	NPC90520
0.8807	High Similarity	NPC296920
0.8793	High Similarity	NPC282496
0.8793	High Similarity	NPC233526
0.8793	High Similarity	NPC136319
0.8761	High Similarity	NPC131118
0.875	High Similarity	NPC203113
0.8738	High Similarity	NPC470161
0.8707	High Similarity	NPC261661
0.8692	High Similarity	NPC164576
0.8684	High Similarity	NPC59561
0.8684	High Similarity	NPC172253
0.8673	High Similarity	NPC471498
0.8673	High Similarity	NPC471503
0.8644	High Similarity	NPC475169
0.8644	High Similarity	NPC193544
0.8644	High Similarity	NPC105925
0.8644	High Similarity	NPC472093
0.8644	High Similarity	NPC17943
0.8644	High Similarity	NPC251855
0.8644	High Similarity	NPC116907
0.8644	High Similarity	NPC105031
0.8644	High Similarity	NPC233410
0.8644	High Similarity	NPC298757
0.8644	High Similarity	NPC221077
0.8644	High Similarity	NPC57490
0.8644	High Similarity	NPC117214
0.8644	High Similarity	NPC208950
0.8644	High Similarity	NPC203133
0.8644	High Similarity	NPC113495
0.8636	High Similarity	NPC255068
0.8636	High Similarity	NPC203924
0.8621	High Similarity	NPC75713
0.8609	High Similarity	NPC471504
0.8609	High Similarity	NPC473290
0.8596	High Similarity	NPC474612
0.8571	High Similarity	NPC112571
0.8571	High Similarity	NPC170485
0.8571	High Similarity	NPC50683
0.8571	High Similarity	NPC285725
0.8559	High Similarity	NPC140521
0.8547	High Similarity	NPC41562
0.8545	High Similarity	NPC475852
0.8534	High Similarity	NPC218753
0.8534	High Similarity	NPC166759
0.8532	High Similarity	NPC75440
0.8505	High Similarity	NPC241891
0.85	High Similarity	NPC159968
0.85	High Similarity	NPC169474
0.85	High Similarity	NPC246620
0.85	High Similarity	NPC236760
0.85	High Similarity	NPC242032
0.85	High Similarity	NPC124452
0.85	High Similarity	NPC236791
0.85	High Similarity	NPC82679
0.85	High Similarity	NPC293054
0.85	High Similarity	NPC473221
0.85	High Similarity	NPC127587
0.85	High Similarity	NPC324112
0.85	High Similarity	NPC282000
0.85	High Similarity	NPC74817
0.8491	Intermediate Similarity	NPC300166
0.8487	Intermediate Similarity	NPC60885
0.8487	Intermediate Similarity	NPC234400
0.8487	Intermediate Similarity	NPC249836
0.8475	Intermediate Similarity	NPC474160
0.8475	Intermediate Similarity	NPC95168
0.8475	Intermediate Similarity	NPC228922
0.8475	Intermediate Similarity	NPC197757
0.8475	Intermediate Similarity	NPC84086
0.8475	Intermediate Similarity	NPC121115
0.8455	Intermediate Similarity	NPC165386
0.8448	Intermediate Similarity	NPC474565
0.843	Intermediate Similarity	NPC31707
0.843	Intermediate Similarity	NPC82862
0.843	Intermediate Similarity	NPC186843
0.843	Intermediate Similarity	NPC470213
0.843	Intermediate Similarity	NPC206615
0.843	Intermediate Similarity	NPC266691
0.843	Intermediate Similarity	NPC98631
0.843	Intermediate Similarity	NPC222127
0.8426	Intermediate Similarity	NPC134829
0.8417	Intermediate Similarity	NPC28730
0.8417	Intermediate Similarity	NPC78974
0.8417	Intermediate Similarity	NPC214406
0.8417	Intermediate Similarity	NPC223136
0.8417	Intermediate Similarity	NPC223953
0.8417	Intermediate Similarity	NPC103823
0.8417	Intermediate Similarity	NPC76451
0.8417	Intermediate Similarity	NPC186845
0.8417	Intermediate Similarity	NPC44748
0.8417	Intermediate Similarity	NPC82299
0.8417	Intermediate Similarity	NPC88297
0.8417	Intermediate Similarity	NPC18924
0.8417	Intermediate Similarity	NPC9891
0.8403	Intermediate Similarity	NPC5796
0.8403	Intermediate Similarity	NPC270030
0.8403	Intermediate Similarity	NPC138248
0.8403	Intermediate Similarity	NPC78446
0.8403	Intermediate Similarity	NPC206487
0.8403	Intermediate Similarity	NPC294156
0.8403	Intermediate Similarity	NPC228503
0.8403	Intermediate Similarity	NPC256015
0.839	Intermediate Similarity	NPC36016
0.839	Intermediate Similarity	NPC262253
0.839	Intermediate Similarity	NPC71579
0.839	Intermediate Similarity	NPC100099
0.839	Intermediate Similarity	NPC473411
0.8378	Intermediate Similarity	NPC106141
0.8362	Intermediate Similarity	NPC226629
0.8362	Intermediate Similarity	NPC85895
0.8362	Intermediate Similarity	NPC308217
0.8362	Intermediate Similarity	NPC137294
0.8361	Intermediate Similarity	NPC474227
0.8361	Intermediate Similarity	NPC471518
0.8361	Intermediate Similarity	NPC469951
0.8361	Intermediate Similarity	NPC471519
0.8361	Intermediate Similarity	NPC469963
0.8361	Intermediate Similarity	NPC190144
0.8361	Intermediate Similarity	NPC476968
0.8361	Intermediate Similarity	NPC170844
0.8349	Intermediate Similarity	NPC118286
0.8349	Intermediate Similarity	NPC109691
0.8349	Intermediate Similarity	NPC470700
0.8349	Intermediate Similarity	NPC39664
0.8349	Intermediate Similarity	NPC302681
0.8349	Intermediate Similarity	NPC113457
0.8349	Intermediate Similarity	NPC39097
0.8348	Intermediate Similarity	NPC304208
0.8348	Intermediate Similarity	NPC52464
0.8347	Intermediate Similarity	NPC471986
0.8347	Intermediate Similarity	NPC473093
0.8347	Intermediate Similarity	NPC202904
0.8347	Intermediate Similarity	NPC473092
0.8347	Intermediate Similarity	NPC189248
0.8347	Intermediate Similarity	NPC474119
0.8347	Intermediate Similarity	NPC46978
0.8347	Intermediate Similarity	NPC8050
0.8347	Intermediate Similarity	NPC210355
0.8333	Intermediate Similarity	NPC265483
0.8333	Intermediate Similarity	NPC299584
0.8333	Intermediate Similarity	NPC131397
0.8333	Intermediate Similarity	NPC82483
0.8333	Intermediate Similarity	NPC105718
0.8333	Intermediate Similarity	NPC278955
0.8333	Intermediate Similarity	NPC241224
0.8333	Intermediate Similarity	NPC476254
0.8319	Intermediate Similarity	NPC165106
0.8319	Intermediate Similarity	NPC38761
0.8319	Intermediate Similarity	NPC76465
0.8318	Intermediate Similarity	NPC100340
0.8318	Intermediate Similarity	NPC143659
0.8305	Intermediate Similarity	NPC54972
0.8305	Intermediate Similarity	NPC212965

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 NPC2682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	1063
0.2-0.3	1411
0.3-0.4	2747
0.4-0.5	1806
0.5-0.6	1061
0.6-0.7	540
0.7-0.8	109
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.839	Intermediate Similarity	NPD2981	Phase 2
0.8361	Intermediate Similarity	NPD3027	Phase 3
0.8319	Intermediate Similarity	NPD2983	Phase 2
0.8319	Intermediate Similarity	NPD2982	Phase 2
0.8319	Intermediate Similarity	NPD5283	Phase 1
0.8211	Intermediate Similarity	NPD4625	Phase 3
0.8197	Intermediate Similarity	NPD3018	Phase 2
0.8167	Intermediate Similarity	NPD4749	Approved
0.8151	Intermediate Similarity	NPD1610	Phase 2
0.813	Intermediate Similarity	NPD4908	Phase 1
0.8125	Intermediate Similarity	NPD5451	Approved
0.812	Intermediate Similarity	NPD1548	Phase 1
0.8115	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD1242	Phase 1
0.7857	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD17	Approved
0.7807	Intermediate Similarity	NPD4750	Phase 3
0.776	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD5535	Approved
0.775	Intermediate Similarity	NPD1651	Approved
0.7734	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1613	Approved
0.7719	Intermediate Similarity	NPD2684	Approved
0.7717	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6671	Approved
0.7658	Intermediate Similarity	NPD940	Approved
0.7658	Intermediate Similarity	NPD846	Approved
0.7642	Intermediate Similarity	NPD1608	Approved
0.7619	Intermediate Similarity	NPD2861	Phase 2
0.7603	Intermediate Similarity	NPD5585	Approved
0.7583	Intermediate Similarity	NPD5536	Phase 2
0.7581	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2796	Approved
0.7576	Intermediate Similarity	NPD3539	Phase 1
0.7563	Intermediate Similarity	NPD709	Approved
0.7563	Intermediate Similarity	NPD2557	Approved
0.7561	Intermediate Similarity	NPD422	Phase 1
0.7556	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD968	Approved
0.7523	Intermediate Similarity	NPD2860	Approved
0.7523	Intermediate Similarity	NPD2859	Approved
0.7521	Intermediate Similarity	NPD228	Approved
0.7519	Intermediate Similarity	NPD3540	Phase 1
0.75	Intermediate Similarity	NPD7124	Phase 2
0.75	Intermediate Similarity	NPD2230	Approved
0.75	Intermediate Similarity	NPD2232	Approved
0.75	Intermediate Similarity	NPD3596	Phase 2
0.75	Intermediate Similarity	NPD2233	Approved
0.7481	Intermediate Similarity	NPD3892	Phase 2
0.7477	Intermediate Similarity	NPD3020	Approved
0.7462	Intermediate Similarity	NPD1240	Approved
0.7462	Intermediate Similarity	NPD2238	Phase 2
0.7459	Intermediate Similarity	NPD3444	Approved
0.7459	Intermediate Similarity	NPD3443	Approved
0.7459	Intermediate Similarity	NPD3445	Approved
0.7459	Intermediate Similarity	NPD5691	Approved
0.7458	Intermediate Similarity	NPD7843	Approved
0.7444	Intermediate Similarity	NPD6100	Approved
0.7444	Intermediate Similarity	NPD6099	Approved
0.744	Intermediate Similarity	NPD5327	Phase 3
0.744	Intermediate Similarity	NPD1669	Approved
0.7431	Intermediate Similarity	NPD2933	Approved
0.7431	Intermediate Similarity	NPD2934	Approved
0.7424	Intermediate Similarity	NPD6111	Discontinued
0.7419	Intermediate Similarity	NPD3705	Approved
0.7419	Intermediate Similarity	NPD1281	Approved
0.7417	Intermediate Similarity	NPD6387	Discontinued
0.7417	Intermediate Similarity	NPD7157	Approved
0.7402	Intermediate Similarity	NPD6584	Phase 3
0.7402	Intermediate Similarity	NPD7905	Discontinued
0.7398	Intermediate Similarity	NPD2668	Approved
0.7398	Intermediate Similarity	NPD4626	Approved
0.7398	Intermediate Similarity	NPD2667	Approved
0.7398	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3134	Approved
0.7377	Intermediate Similarity	NPD6581	Approved
0.7377	Intermediate Similarity	NPD6580	Approved
0.7353	Intermediate Similarity	NPD7466	Approved
0.7348	Intermediate Similarity	NPD1607	Approved
0.7339	Intermediate Similarity	NPD3847	Discontinued
0.7328	Intermediate Similarity	NPD290	Approved
0.7317	Intermediate Similarity	NPD3049	Approved
0.7317	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4359	Approved
0.7293	Intermediate Similarity	NPD2200	Suspended
0.7286	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD1611	Approved
0.7266	Intermediate Similarity	NPD4624	Approved
0.7258	Intermediate Similarity	NPD6516	Phase 2
0.7258	Intermediate Similarity	NPD5846	Approved
0.7258	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1778	Approved
0.7244	Intermediate Similarity	NPD1283	Approved
0.7244	Intermediate Similarity	NPD2922	Phase 1
0.7239	Intermediate Similarity	NPD1510	Phase 2
0.7239	Intermediate Similarity	NPD3748	Approved
0.7236	Intermediate Similarity	NPD1182	Approved
0.7227	Intermediate Similarity	NPD1137	Approved
0.7227	Intermediate Similarity	NPD1139	Approved
0.7222	Intermediate Similarity	NPD2231	Phase 2
0.7222	Intermediate Similarity	NPD2235	Phase 2
0.7222	Intermediate Similarity	NPD3972	Approved
0.7207	Intermediate Similarity	NPD844	Approved
0.7203	Intermediate Similarity	NPD3022	Approved
0.7203	Intermediate Similarity	NPD3021	Approved
0.72	Intermediate Similarity	NPD3496	Discontinued
0.7188	Intermediate Similarity	NPD2797	Approved
0.7179	Intermediate Similarity	NPD1358	Approved
0.7176	Intermediate Similarity	NPD5110	Phase 2
0.7176	Intermediate Similarity	NPD5111	Phase 2
0.7176	Intermediate Similarity	NPD5109	Approved
0.7167	Intermediate Similarity	NPD1138	Approved
0.7167	Intermediate Similarity	NPD821	Approved
0.7165	Intermediate Similarity	NPD6582	Phase 2
0.7165	Intermediate Similarity	NPD6583	Phase 3
0.7165	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD1091	Approved
0.712	Intermediate Similarity	NPD2556	Approved
0.712	Intermediate Similarity	NPD2554	Approved
0.7109	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6696	Suspended
0.7109	Intermediate Similarity	NPD8651	Approved
0.7109	Intermediate Similarity	NPD1876	Approved
0.7107	Intermediate Similarity	NPD1241	Discontinued
0.7105	Intermediate Similarity	NPD3028	Approved
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7095	Approved
0.7097	Intermediate Similarity	NPD2486	Discontinued
0.709	Intermediate Similarity	NPD4097	Suspended
0.7087	Intermediate Similarity	NPD1840	Phase 2
0.7087	Intermediate Similarity	NPD1244	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4357	Discontinued
0.7071	Intermediate Similarity	NPD7213	Phase 3
0.7071	Intermediate Similarity	NPD7212	Phase 2
0.7068	Intermediate Similarity	NPD4060	Phase 1
0.7068	Intermediate Similarity	NPD2979	Phase 3
0.7063	Intermediate Similarity	NPD4005	Discontinued
0.7063	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7054	Intermediate Similarity	NPD3266	Approved
0.7054	Intermediate Similarity	NPD3267	Approved
0.7054	Intermediate Similarity	NPD4098	Discontinued
0.7045	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1296	Phase 2
0.7045	Intermediate Similarity	NPD5718	Phase 2
0.704	Intermediate Similarity	NPD6382	Discontinued
0.7037	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4536	Approved
0.7037	Intermediate Similarity	NPD4538	Approved
0.7031	Intermediate Similarity	NPD6539	Approved
0.7031	Intermediate Similarity	NPD6540	Phase 3
0.7031	Intermediate Similarity	NPD6542	Approved
0.7031	Intermediate Similarity	NPD6543	Approved
0.7023	Intermediate Similarity	NPD6832	Phase 2
0.7015	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5735	Approved
0.7015	Intermediate Similarity	NPD5124	Phase 1
0.7009	Intermediate Similarity	NPD9697	Approved
0.7007	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2798	Approved
0.6992	Remote Similarity	NPD4870	Approved
0.6991	Remote Similarity	NPD288	Approved
0.6986	Remote Similarity	NPD7819	Suspended
0.6986	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7033	Discontinued
0.6985	Remote Similarity	NPD4108	Discontinued
0.6978	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD3225	Approved
0.6977	Remote Similarity	NPD6538	Approved
0.6977	Remote Similarity	NPD6541	Approved
0.6972	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1894	Discontinued
0.6957	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1549	Phase 2
0.6957	Remote Similarity	NPD970	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6799	Approved
0.694	Remote Similarity	NPD1558	Phase 1
0.694	Remote Similarity	NPD4140	Approved
0.6934	Remote Similarity	NPD2438	Suspended
0.6934	Remote Similarity	NPD1551	Phase 2
0.6929	Remote Similarity	NPD3294	Phase 2
0.6918	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD37	Approved
0.6917	Remote Similarity	NPD3268	Approved
0.6912	Remote Similarity	NPD6896	Approved
0.6912	Remote Similarity	NPD6895	Approved
0.6911	Remote Similarity	NPD593	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