NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	276.379
LogP:	2.091
LogD:	2.784
LogS:	-2.852
# Rotatable Bonds:	3
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	2.514
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.026
MDCK Permeability:	1.1452010767243337e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	93.97623443603516%
Volume Distribution (VD):	0.475
Pgp-substrate:	2.4586596488952637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.455
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.157
CYP2D6-substrate:	0.424
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	12.706
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.157
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.743
Skin Sensitization:	0.956
Carcinogencity:	0.041
Eye Corrosion:	0.11
Eye Irritation:	0.967
Respiratory Toxicity:	0.422

Download Data

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

Natural Product: NPC61516

Natural Product ID:	NPC61516
*Common Name:**	Trans-3,3',5,5'-Tetrahydroxy-4'-Methoxystilbene
IUPAC Name:	5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol
Synonyms:
Standard InCHIKey:	BKJYMZRGLINXRP-NSCUHMNNSA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-20-15-13(18)6-10(7-14(15)19)3-2-9-4-11(16)8-12(17)5-9/h2-8,16-19H,1H3/b3-2+
SMILES:	COc1c(O)cc(cc1O)/C=C/c1cc(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470459
PubChem CID:	13499470
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
NPO1943	Yucca schidigera	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757713]
NPO1943	Yucca schidigera	Species	Asparagaceae	Eukaryota	bark	n.a.	n.a.	PMID[15165156]
NPO4278	Wikstroemia monticola	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4278	Wikstroemia monticola	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1943	Yucca schidigera	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4278	Wikstroemia monticola	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO559	Mimusops globosa	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1671.1	Xanthium strumarium var. canadense	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6675	Aplophyllum myrtifolium	n.a.	n.a.	n.a.	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
Others	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.252	mM	PMID[522867]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	3.1	%	PMID[522867]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.9	%	PMID[522867]

☑ 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 NPC61516 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	427
0.1-0.2	2124
0.2-0.3	7620
0.3-0.4	12090
0.4-0.5	3573
0.5-0.6	4730
0.6-0.7	7733
0.7-0.8	3279
0.8-0.85	610
0.85-0.9	385
0.9-0.95	97
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232084
1.0	High Similarity	NPC247364
1.0	High Similarity	NPC10932
0.9739	High Similarity	NPC262253
0.9739	High Similarity	NPC71579
0.9739	High Similarity	NPC473411
0.9735	High Similarity	NPC226629
0.9655	High Similarity	NPC197757
0.9655	High Similarity	NPC228922
0.9649	High Similarity	NPC474565
0.9569	High Similarity	NPC41562
0.9565	High Similarity	NPC166759
0.9558	High Similarity	NPC259638
0.9492	High Similarity	NPC82483
0.9492	High Similarity	NPC17943
0.9492	High Similarity	NPC472093
0.9492	High Similarity	NPC265483
0.9492	High Similarity	NPC251855
0.9492	High Similarity	NPC299584
0.9492	High Similarity	NPC221077
0.9492	High Similarity	NPC208950
0.9492	High Similarity	NPC193544
0.9492	High Similarity	NPC203133
0.9492	High Similarity	NPC116907
0.9492	High Similarity	NPC298757
0.9492	High Similarity	NPC233410
0.9492	High Similarity	NPC57490
0.9492	High Similarity	NPC117214
0.9492	High Similarity	NPC475169
0.9483	High Similarity	NPC145780
0.9478	High Similarity	NPC229401
0.9469	High Similarity	NPC193067
0.9412	High Similarity	NPC44748
0.9412	High Similarity	NPC18924
0.9412	High Similarity	NPC78974
0.9412	High Similarity	NPC223136
0.9412	High Similarity	NPC214406
0.9412	High Similarity	NPC28730
0.9412	High Similarity	NPC103823
0.9407	High Similarity	NPC206487
0.9407	High Similarity	NPC5796
0.9391	High Similarity	NPC20674
0.9333	High Similarity	NPC127587
0.9333	High Similarity	NPC246620
0.9333	High Similarity	NPC124452
0.9333	High Similarity	NPC236791
0.9333	High Similarity	NPC282000
0.9333	High Similarity	NPC159968
0.9333	High Similarity	NPC324112
0.9333	High Similarity	NPC169474
0.9333	High Similarity	NPC210355
0.9333	High Similarity	NPC82679
0.9333	High Similarity	NPC74817
0.9333	High Similarity	NPC266555
0.9333	High Similarity	NPC293054
0.9328	High Similarity	NPC60885
0.9328	High Similarity	NPC234400
0.9322	High Similarity	NPC282496
0.9322	High Similarity	NPC84086
0.9322	High Similarity	NPC233526
0.9322	High Similarity	NPC95168
0.9322	High Similarity	NPC121115
0.9322	High Similarity	NPC136319
0.9256	High Similarity	NPC98631
0.9256	High Similarity	NPC206615
0.9256	High Similarity	NPC186843
0.9256	High Similarity	NPC470213
0.9256	High Similarity	NPC154866
0.925	High Similarity	NPC76451
0.9196	High Similarity	NPC296920
0.9196	High Similarity	NPC90520
0.918	High Similarity	NPC212015
0.918	High Similarity	NPC476968
0.918	High Similarity	NPC58164
0.918	High Similarity	NPC170844
0.918	High Similarity	NPC10225
0.918	High Similarity	NPC228769
0.918	High Similarity	NPC470633
0.9174	High Similarity	NPC252131
0.9167	High Similarity	NPC105925
0.916	High Similarity	NPC238810
0.9153	High Similarity	NPC75713
0.9153	High Similarity	NPC49341
0.913	High Similarity	NPC123948
0.9115	High Similarity	NPC280606
0.9106	High Similarity	NPC311680
0.9106	High Similarity	NPC472338
0.9106	High Similarity	NPC126836
0.9106	High Similarity	NPC234488
0.9106	High Similarity	NPC51840
0.9106	High Similarity	NPC299221
0.9098	High Similarity	NPC28765
0.9091	High Similarity	NPC223953
0.9083	High Similarity	NPC183446
0.9083	High Similarity	NPC228972
0.9083	High Similarity	NPC122792
0.9052	High Similarity	NPC293619
0.9032	High Similarity	NPC474017
0.9032	High Similarity	NPC470095
0.9032	High Similarity	NPC472597
0.9032	High Similarity	NPC470096
0.9032	High Similarity	NPC232275
0.9024	High Similarity	NPC45824
0.9018	High Similarity	NPC246358
0.9018	High Similarity	NPC36108
0.9018	High Similarity	NPC7097
0.9018	High Similarity	NPC233731
0.9016	High Similarity	NPC236760
0.9016	High Similarity	NPC470699
0.9008	High Similarity	NPC58279
0.9008	High Similarity	NPC300326
0.9008	High Similarity	NPC271985
0.9	High Similarity	NPC165375
0.9	High Similarity	NPC220598
0.8974	High Similarity	NPC470626
0.8966	High Similarity	NPC203113
0.896	High Similarity	NPC35932
0.896	High Similarity	NPC201587
0.896	High Similarity	NPC16208
0.896	High Similarity	NPC7903
0.896	High Similarity	NPC253105
0.896	High Similarity	NPC184447
0.896	High Similarity	NPC86655
0.896	High Similarity	NPC202762
0.896	High Similarity	NPC160991
0.896	High Similarity	NPC6451
0.8957	High Similarity	NPC228287
0.8957	High Similarity	NPC180508
0.8952	High Similarity	NPC91291
0.8952	High Similarity	NPC214860
0.8943	High Similarity	NPC266691
0.8938	High Similarity	NPC94045
0.8934	High Similarity	NPC181361
0.8929	High Similarity	NPC105727
0.8929	High Similarity	NPC114392
0.8929	High Similarity	NPC58427
0.8929	High Similarity	NPC34864
0.8898	High Similarity	NPC475961
0.8898	High Similarity	NPC254625
0.8889	High Similarity	NPC471391
0.8889	High Similarity	NPC36661
0.8889	High Similarity	NPC32778
0.8889	High Similarity	NPC158331
0.8889	High Similarity	NPC168059
0.8889	High Similarity	NPC471390
0.8889	High Similarity	NPC229442
0.8889	High Similarity	NPC475840
0.888	High Similarity	NPC474356
0.888	High Similarity	NPC12275
0.888	High Similarity	NPC45715
0.8871	High Similarity	NPC3439
0.8871	High Similarity	NPC226788
0.8871	High Similarity	NPC210623
0.8871	High Similarity	NPC273295
0.8871	High Similarity	NPC218856
0.8871	High Similarity	NPC202582
0.8871	High Similarity	NPC222004
0.8871	High Similarity	NPC285339
0.8871	High Similarity	NPC470258
0.8871	High Similarity	NPC190629
0.8862	High Similarity	NPC216836
0.8862	High Similarity	NPC474119
0.886	High Similarity	NPC203924
0.886	High Similarity	NPC156840
0.886	High Similarity	NPC257124
0.886	High Similarity	NPC8547
0.886	High Similarity	NPC78918
0.886	High Similarity	NPC173746
0.886	High Similarity	NPC139617
0.885	High Similarity	NPC165386
0.8843	High Similarity	NPC471693
0.8839	High Similarity	NPC176527
0.8833	High Similarity	NPC343720
0.8833	High Similarity	NPC54872
0.8833	High Similarity	NPC473853
0.8833	High Similarity	NPC184651
0.8833	High Similarity	NPC470212
0.8833	High Similarity	NPC113865
0.8833	High Similarity	NPC285289
0.8833	High Similarity	NPC262156
0.8833	High Similarity	NPC324571
0.8833	High Similarity	NPC312675
0.8824	High Similarity	NPC232316
0.8824	High Similarity	NPC227217
0.8824	High Similarity	NPC56214
0.8824	High Similarity	NPC117780
0.8824	High Similarity	NPC35071
0.8824	High Similarity	NPC177475
0.8824	High Similarity	NPC165133
0.8824	High Similarity	NPC148615
0.8824	High Similarity	NPC242885
0.8824	High Similarity	NPC95614
0.8819	High Similarity	NPC160697
0.8819	High Similarity	NPC287745
0.8819	High Similarity	NPC170694
0.8819	High Similarity	NPC111635
0.8819	High Similarity	NPC317380
0.8819	High Similarity	NPC310854
0.8814	High Similarity	NPC63083
0.8814	High Similarity	NPC255675

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 NPC61516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	1015
0.2-0.3	1993
0.3-0.4	2725
0.4-0.5	1547
0.5-0.6	873
0.6-0.7	524
0.7-0.8	88
0.8-0.85	7
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.918	High Similarity	NPD3027	Phase 3
0.886	High Similarity	NPD228	Approved
0.879	High Similarity	NPD1529	Clinical (unspecified phase)
0.871	High Similarity	NPD1530	Clinical (unspecified phase)
0.8689	High Similarity	NPD2983	Phase 2
0.8689	High Similarity	NPD2982	Phase 2
0.8661	High Similarity	NPD1613	Approved
0.8661	High Similarity	NPD1612	Clinical (unspecified phase)
0.8607	High Similarity	NPD2981	Phase 2
0.8537	High Similarity	NPD4379	Clinical (unspecified phase)
0.8413	Intermediate Similarity	NPD3018	Phase 2
0.8304	Intermediate Similarity	NPD1242	Phase 1
0.8235	Intermediate Similarity	NPD5283	Phase 1
0.8049	Intermediate Similarity	NPD1548	Phase 1
0.7967	Intermediate Similarity	NPD5536	Phase 2
0.7955	Intermediate Similarity	NPD1558	Phase 1
0.7937	Intermediate Similarity	NPD1610	Phase 2
0.7899	Intermediate Similarity	NPD3021	Approved
0.7899	Intermediate Similarity	NPD3022	Approved
0.7857	Intermediate Similarity	NPD9296	Approved
0.784	Intermediate Similarity	NPD1357	Approved
0.7786	Intermediate Similarity	NPD4357	Discontinued
0.7786	Intermediate Similarity	NPD4908	Phase 1
0.7737	Intermediate Similarity	NPD3540	Phase 1
0.7724	Intermediate Similarity	NPD1934	Approved
0.771	Intermediate Similarity	NPD9494	Approved
0.7671	Intermediate Similarity	NPD2801	Approved
0.7669	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3539	Phase 1
0.766	Intermediate Similarity	NPD1511	Approved
0.7569	Intermediate Similarity	NPD1653	Approved
0.7568	Intermediate Similarity	NPD3882	Suspended
0.7556	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3620	Phase 2
0.7552	Intermediate Similarity	NPD1512	Approved
0.7537	Intermediate Similarity	NPD3145	Approved
0.7537	Intermediate Similarity	NPD3144	Approved
0.7519	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7481	Intermediate Similarity	NPD2674	Phase 3
0.7466	Intermediate Similarity	NPD4675	Approved
0.7466	Intermediate Similarity	NPD4678	Approved
0.7463	Intermediate Similarity	NPD4625	Phase 3
0.7458	Intermediate Similarity	NPD291	Approved
0.7458	Intermediate Similarity	NPD940	Approved
0.7458	Intermediate Similarity	NPD846	Approved
0.7438	Intermediate Similarity	NPD290	Approved
0.7432	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4749	Approved
0.7394	Intermediate Similarity	NPD2219	Phase 1
0.7394	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3705	Approved
0.7377	Intermediate Similarity	NPD2684	Approved
0.7351	Intermediate Similarity	NPD6234	Discontinued
0.7343	Intermediate Similarity	NPD7124	Phase 2
0.7321	Intermediate Similarity	NPD9094	Approved
0.7299	Intermediate Similarity	NPD4060	Phase 1
0.7299	Intermediate Similarity	NPD1240	Approved
0.7299	Intermediate Similarity	NPD943	Approved
0.728	Intermediate Similarity	NPD7843	Approved
0.7279	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4005	Discontinued
0.7258	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1091	Approved
0.7248	Intermediate Similarity	NPD37	Approved
0.7244	Intermediate Similarity	NPD7157	Approved
0.7241	Intermediate Similarity	NPD2934	Approved
0.7241	Intermediate Similarity	NPD2933	Approved
0.7239	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7266	Discontinued
0.7226	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6166	Phase 2
0.7219	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2922	Phase 1
0.7214	Intermediate Similarity	NPD1510	Phase 2
0.7194	Intermediate Similarity	NPD1607	Approved
0.7185	Intermediate Similarity	NPD2861	Phase 2
0.7179	Intermediate Similarity	NPD2860	Approved
0.7179	Intermediate Similarity	NPD2859	Approved
0.7177	Intermediate Similarity	NPD4750	Phase 3
0.7172	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1358	Approved
0.7153	Intermediate Similarity	NPD5109	Approved
0.7153	Intermediate Similarity	NPD5110	Phase 2
0.7153	Intermediate Similarity	NPD5111	Phase 2
0.7153	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD3020	Approved
0.7143	Intermediate Similarity	NPD6111	Discontinued
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4236	Phase 3
0.7133	Intermediate Similarity	NPD4237	Approved
0.7132	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4123	Phase 3
0.7111	Intermediate Similarity	NPD6584	Phase 3
0.7109	Intermediate Similarity	NPD6671	Approved
0.7105	Intermediate Similarity	NPD4966	Approved
0.7105	Intermediate Similarity	NPD4965	Approved
0.7105	Intermediate Similarity	NPD4967	Phase 2
0.7097	Intermediate Similarity	NPD6232	Discontinued
0.7089	Intermediate Similarity	NPD7054	Approved
0.7086	Intermediate Similarity	NPD1465	Phase 2
0.7086	Intermediate Similarity	NPD2978	Approved
0.7086	Intermediate Similarity	NPD2977	Approved
0.708	Intermediate Similarity	NPD7095	Approved
0.7075	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9269	Phase 2
0.7063	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5297	Approved
0.7054	Intermediate Similarity	NPD111	Approved
0.7044	Intermediate Similarity	NPD7074	Phase 3
0.7044	Intermediate Similarity	NPD7472	Approved
0.704	Intermediate Similarity	NPD5451	Approved
0.7034	Intermediate Similarity	NPD6190	Approved
0.7032	Intermediate Similarity	NPD7199	Phase 2
0.7029	Intermediate Similarity	NPD5718	Phase 2
0.7025	Intermediate Similarity	NPD7228	Approved
0.7025	Intermediate Similarity	NPD3818	Discontinued
0.7021	Intermediate Similarity	NPD4536	Approved
0.7021	Intermediate Similarity	NPD4538	Approved
0.7021	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5177	Phase 3
0.7014	Intermediate Similarity	NPD4162	Approved
0.7008	Intermediate Similarity	NPD9377	Approved
0.7008	Intermediate Similarity	NPD9379	Approved
0.7	Intermediate Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD709	Approved
0.697	Remote Similarity	NPD9381	Approved
0.697	Remote Similarity	NPD9384	Approved
0.697	Remote Similarity	NPD5846	Approved
0.697	Remote Similarity	NPD6516	Phase 2
0.6963	Remote Similarity	NPD1283	Approved
0.6962	Remote Similarity	NPD7473	Discontinued
0.6957	Remote Similarity	NPD9295	Approved
0.6948	Remote Similarity	NPD4055	Discovery
0.6947	Remote Similarity	NPD1182	Approved
0.6944	Remote Similarity	NPD1549	Phase 2
0.6943	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1608	Approved
0.6933	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2238	Phase 2
0.6928	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1551	Phase 2
0.6923	Remote Similarity	NPD2935	Discontinued
0.6918	Remote Similarity	NPD5241	Discontinued
0.6917	Remote Similarity	NPD3847	Discontinued
0.6905	Remote Similarity	NPD556	Approved
0.6901	Remote Similarity	NPD6895	Approved
0.6901	Remote Similarity	NPD6896	Approved
0.6899	Remote Similarity	NPD9299	Approved
0.6897	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1652	Phase 2
0.6894	Remote Similarity	NPD1651	Approved
0.6894	Remote Similarity	NPD6797	Phase 2
0.6892	Remote Similarity	NPD1424	Approved
0.6892	Remote Similarity	NPD7447	Phase 1
0.6892	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6582	Phase 2
0.6889	Remote Similarity	NPD6583	Phase 3
0.6889	Remote Similarity	NPD1669	Approved
0.6889	Remote Similarity	NPD9622	Approved
0.6887	Remote Similarity	NPD4380	Phase 2
0.6879	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5535	Approved
0.6875	Remote Similarity	NPD1375	Discontinued
0.6875	Remote Similarity	NPD821	Approved
0.6875	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1535	Discovery
0.6857	Remote Similarity	NPD6233	Phase 2
0.6853	Remote Similarity	NPD5588	Approved
0.6853	Remote Similarity	NPD5960	Phase 3
0.6852	Remote Similarity	NPD7251	Discontinued
0.6849	Remote Similarity	NPD6331	Phase 2
0.6849	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3750	Approved
0.6849	Remote Similarity	NPD4110	Phase 3
0.6846	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2668	Approved
0.6842	Remote Similarity	NPD4626	Approved
0.6842	Remote Similarity	NPD2667	Approved
0.6838	Remote Similarity	NPD8651	Approved
0.6838	Remote Similarity	NPD9365	Approved
0.6829	Remote Similarity	NPD8053	Approved
0.6829	Remote Similarity	NPD8054	Approved
0.6824	Remote Similarity	NPD7212	Phase 2
0.6824	Remote Similarity	NPD7213	Phase 3
0.6824	Remote Similarity	NPD6799	Approved
0.6815	Remote Similarity	NPD2233	Approved
0.6815	Remote Similarity	NPD2230	Approved
0.6815	Remote Similarity	NPD1481	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