NPASS Compound

Structure

NPC166759 OpenBabel07101718202D 21 22 0 0 0 0 0 0 0 0999 V2000 7.7942 0.5000 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 -1.7321 -0.0000 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 3.4641 -0.0000 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 0.8660 -1.5000 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 5.1962 -0.0000 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 15 2 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	302.181
LogP:	3.034
LogD:	3.504
LogS:	-4.063
# Rotatable Bonds:	5
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.853
Synthetic Accessibility Score:	1.963
Fsp3:	0.176
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:	-4.91
MDCK Permeability:	1.545748636999633e-05
Pgp-inhibitor:	0.111
Pgp-substrate:	0.528
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	94.72004699707031%
Volume Distribution (VD):	0.728
Pgp-substrate:	2.9616878032684326%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.765
CYP2C19-substrate:	0.491
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.33
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.386

ADMET: Excretion

Clearance (CL):	11.016
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.334
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.818
AMES Toxicity:	0.148
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.264
Skin Sensitization:	0.932
Carcinogencity:	0.101
Eye Corrosion:	0.05
Eye Irritation:	0.811
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC166759

Natural Product ID:	NPC166759
*Common Name:**	3-Hydroxy-4,3',5'-Trimethoxy-Trans-Stilbene
IUPAC Name:	3-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-5-methoxyphenol
Synonyms:
Standard InCHIKey:	VLLUXNYOVSHCHO-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-19-15-9-13(8-14(18)11-15)5-4-12-6-7-16(20-2)17(10-12)21-3/h4-11,18H,1-3H3/b5-4+
SMILES:	COc1cc(/C=C/c2ccc(c(c2)OC)OC)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL109860
PubChem CID:	15698945
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
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10714491]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384315]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	Stems	n.a.	n.a.	PMID[29227656]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO88	Rheum undulatum	Species	Polygonaceae	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
ED50	1
IC50	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[569914]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	8.7	nM	PMID[569914]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	19000.0	nM	PMID[569913]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[569914]

☑ 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 NPC166759 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	357
0.1-0.2	1961
0.2-0.3	6556
0.3-0.4	13045
0.4-0.5	3466
0.5-0.6	4630
0.6-0.7	7819
0.7-0.8	3608
0.8-0.85	713
0.85-0.9	398
0.9-0.95	111
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC474565
0.9826	High Similarity	NPC473411
0.9826	High Similarity	NPC262253
0.9826	High Similarity	NPC71579
0.9741	High Similarity	NPC233526
0.9741	High Similarity	NPC282496
0.9576	High Similarity	NPC117214
0.9576	High Similarity	NPC193544
0.9576	High Similarity	NPC475169
0.9576	High Similarity	NPC265483
0.9576	High Similarity	NPC299584
0.9576	High Similarity	NPC82483
0.9576	High Similarity	NPC17943
0.9576	High Similarity	NPC221077
0.9576	High Similarity	NPC233410
0.9576	High Similarity	NPC251855
0.9576	High Similarity	NPC208950
0.9576	High Similarity	NPC116907
0.9576	High Similarity	NPC105925
0.9576	High Similarity	NPC57490
0.9576	High Similarity	NPC472093
0.9576	High Similarity	NPC203133
0.9576	High Similarity	NPC298757
0.9569	High Similarity	NPC75713
0.9565	High Similarity	NPC247364
0.9565	High Similarity	NPC10932
0.9565	High Similarity	NPC61516
0.9565	High Similarity	NPC232084
0.9558	High Similarity	NPC123948
0.9496	High Similarity	NPC103823
0.9496	High Similarity	NPC18924
0.9496	High Similarity	NPC28730
0.9496	High Similarity	NPC44748
0.9496	High Similarity	NPC78974
0.9496	High Similarity	NPC223136
0.9496	High Similarity	NPC214406
0.9478	High Similarity	NPC226629
0.9417	High Similarity	NPC293054
0.9417	High Similarity	NPC127587
0.9417	High Similarity	NPC246620
0.9417	High Similarity	NPC282000
0.9417	High Similarity	NPC74817
0.9417	High Similarity	NPC124452
0.9417	High Similarity	NPC324112
0.9417	High Similarity	NPC236791
0.9417	High Similarity	NPC169474
0.9417	High Similarity	NPC159968
0.9417	High Similarity	NPC82679
0.9417	High Similarity	NPC210355
0.9412	High Similarity	NPC234400
0.9412	High Similarity	NPC60885
0.9407	High Similarity	NPC95168
0.9407	High Similarity	NPC136319
0.9407	High Similarity	NPC228922
0.9407	High Similarity	NPC197757
0.9381	High Similarity	NPC180508
0.9381	High Similarity	NPC228287
0.9339	High Similarity	NPC470213
0.9339	High Similarity	NPC206615
0.9339	High Similarity	NPC98631
0.9339	High Similarity	NPC186843
0.9333	High Similarity	NPC223953
0.9333	High Similarity	NPC76451
0.9322	High Similarity	NPC41562
0.931	High Similarity	NPC475961
0.931	High Similarity	NPC254625
0.9304	High Similarity	NPC259638
0.9262	High Similarity	NPC228769
0.9262	High Similarity	NPC58164
0.9262	High Similarity	NPC470633
0.9262	High Similarity	NPC476968
0.9262	High Similarity	NPC10225
0.9262	High Similarity	NPC170844
0.9237	High Similarity	NPC145780
0.9231	High Similarity	NPC229401
0.9217	High Similarity	NPC193067
0.9204	High Similarity	NPC280606
0.9187	High Similarity	NPC51840
0.9187	High Similarity	NPC224157
0.9187	High Similarity	NPC192687
0.9187	High Similarity	NPC299221
0.9187	High Similarity	NPC311680
0.9187	High Similarity	NPC126836
0.9187	High Similarity	NPC234488
0.9187	High Similarity	NPC472338
0.9187	High Similarity	NPC63574
0.918	High Similarity	NPC28765
0.918	High Similarity	NPC154866
0.9167	High Similarity	NPC5796
0.9167	High Similarity	NPC122792
0.9167	High Similarity	NPC206487
0.9167	High Similarity	NPC228972
0.9153	High Similarity	NPC199023
0.9153	High Similarity	NPC472596
0.9145	High Similarity	NPC20674
0.9138	High Similarity	NPC474933
0.9115	High Similarity	NPC203924
0.9115	High Similarity	NPC90520
0.9115	High Similarity	NPC296920
0.9113	High Similarity	NPC470095
0.9113	High Similarity	NPC470096
0.9113	High Similarity	NPC472597
0.9113	High Similarity	NPC474017
0.9106	High Similarity	NPC469963
0.9106	High Similarity	NPC190144
0.9106	High Similarity	NPC3439
0.9106	High Similarity	NPC218856
0.9106	High Similarity	NPC226788
0.9106	High Similarity	NPC210623
0.9106	High Similarity	NPC190629
0.9106	High Similarity	NPC222004
0.9106	High Similarity	NPC285339
0.9106	High Similarity	NPC202582
0.9106	High Similarity	NPC470258
0.9106	High Similarity	NPC273295
0.9106	High Similarity	NPC469951
0.9106	High Similarity	NPC212015
0.9098	High Similarity	NPC252131
0.9098	High Similarity	NPC474119
0.9098	High Similarity	NPC236760
0.9098	High Similarity	NPC266555
0.9098	High Similarity	NPC470699
0.9098	High Similarity	NPC242032
0.9083	High Similarity	NPC84086
0.9083	High Similarity	NPC121115
0.9076	High Similarity	NPC477886
0.9076	High Similarity	NPC49341
0.906	High Similarity	NPC63083
0.9052	High Similarity	NPC141090
0.9052	High Similarity	NPC203113
0.904	High Similarity	NPC6451
0.904	High Similarity	NPC184447
0.904	High Similarity	NPC35932
0.904	High Similarity	NPC16208
0.904	High Similarity	NPC253105
0.904	High Similarity	NPC160991
0.904	High Similarity	NPC245120
0.904	High Similarity	NPC7903
0.904	High Similarity	NPC201587
0.9032	High Similarity	NPC214860
0.9027	High Similarity	NPC94045
0.9024	High Similarity	NPC266691
0.9016	High Similarity	NPC181361
0.9008	High Similarity	NPC183446
0.9	High Similarity	NPC261661
0.8983	High Similarity	NPC15805
0.8974	High Similarity	NPC470759
0.8974	High Similarity	NPC219070
0.8974	High Similarity	NPC127894
0.8974	High Similarity	NPC15860
0.8968	High Similarity	NPC475840
0.8968	High Similarity	NPC471391
0.8968	High Similarity	NPC158331
0.8968	High Similarity	NPC471390
0.8968	High Similarity	NPC32778
0.8968	High Similarity	NPC168059
0.8968	High Similarity	NPC36661
0.8968	High Similarity	NPC229442
0.8966	High Similarity	NPC53906
0.896	High Similarity	NPC232275
0.896	High Similarity	NPC45715
0.896	High Similarity	NPC30043
0.896	High Similarity	NPC469613
0.896	High Similarity	NPC469625
0.896	High Similarity	NPC474356
0.896	High Similarity	NPC12275
0.8957	High Similarity	NPC204120
0.8952	High Similarity	NPC45824
0.8938	High Similarity	NPC165386
0.8938	High Similarity	NPC82016
0.8926	High Similarity	NPC220598
0.8926	High Similarity	NPC238810
0.8926	High Similarity	NPC165375
0.8926	High Similarity	NPC471693
0.8917	High Similarity	NPC285289
0.8917	High Similarity	NPC476633
0.8898	High Similarity	NPC170694
0.8898	High Similarity	NPC287745
0.8898	High Similarity	NPC470626
0.8898	High Similarity	NPC317380
0.8898	High Similarity	NPC111635
0.8898	High Similarity	NPC310854
0.8889	High Similarity	NPC161958
0.8889	High Similarity	NPC14224
0.8889	High Similarity	NPC114064
0.8889	High Similarity	NPC204215
0.8889	High Similarity	NPC127624
0.8889	High Similarity	NPC86655
0.8889	High Similarity	NPC202762
0.8889	High Similarity	NPC175067
0.8889	High Similarity	NPC470752
0.888	High Similarity	NPC91291
0.888	High Similarity	NPC469614
0.888	High Similarity	NPC184814
0.888	High Similarity	NPC469612
0.8879	High Similarity	NPC276737
0.8879	High Similarity	NPC22610
0.8852	High Similarity	NPC114901
0.8852	High Similarity	NPC48990
0.8852	High Similarity	NPC293701

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 NPC166759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	1014
0.2-0.3	1858
0.3-0.4	2780
0.4-0.5	1586
0.5-0.6	915
0.6-0.7	560
0.7-0.8	101
0.8-0.85	10
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9262	High Similarity	NPD3027	Phase 3
0.9083	High Similarity	NPD2982	Phase 2
0.9083	High Similarity	NPD2983	Phase 2
0.9	High Similarity	NPD2981	Phase 2
0.879	High Similarity	NPD3018	Phase 2
0.8571	High Similarity	NPD1529	Clinical (unspecified phase)
0.8492	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8475	Intermediate Similarity	NPD5283	Phase 1
0.8468	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD228	Approved
0.845	Intermediate Similarity	NPD1613	Approved
0.845	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD1242	Phase 1
0.8197	Intermediate Similarity	NPD5536	Phase 2
0.814	Intermediate Similarity	NPD4908	Phase 1
0.813	Intermediate Similarity	NPD1548	Phase 1
0.8116	Intermediate Similarity	NPD4357	Discontinued
0.8074	Intermediate Similarity	NPD3540	Phase 1
0.8016	Intermediate Similarity	NPD1610	Phase 2
0.8015	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3539	Phase 1
0.792	Intermediate Similarity	NPD1357	Approved
0.7833	Intermediate Similarity	NPD3021	Approved
0.7833	Intermediate Similarity	NPD3022	Approved
0.7803	Intermediate Similarity	NPD4625	Phase 3
0.7778	Intermediate Similarity	NPD4678	Approved
0.7778	Intermediate Similarity	NPD4675	Approved
0.7761	Intermediate Similarity	NPD1558	Phase 1
0.7752	Intermediate Similarity	NPD4749	Approved
0.774	Intermediate Similarity	NPD2801	Approved
0.7734	Intermediate Similarity	NPD3705	Approved
0.7714	Intermediate Similarity	NPD2219	Phase 1
0.7714	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3060	Approved
0.7671	Intermediate Similarity	NPD1934	Approved
0.766	Intermediate Similarity	NPD7124	Phase 2
0.7635	Intermediate Similarity	NPD3882	Suspended
0.7615	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD422	Phase 1
0.7586	Intermediate Similarity	NPD4005	Discontinued
0.7576	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD37	Approved
0.7542	Intermediate Similarity	NPD846	Approved
0.7542	Intermediate Similarity	NPD940	Approved
0.7519	Intermediate Similarity	NPD2861	Phase 2
0.7517	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD3620	Phase 2
0.75	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3145	Approved
0.7481	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3144	Approved
0.7478	Intermediate Similarity	NPD2933	Approved
0.7478	Intermediate Similarity	NPD9296	Approved
0.7478	Intermediate Similarity	NPD2934	Approved
0.7464	Intermediate Similarity	NPD6111	Discontinued
0.7459	Intermediate Similarity	NPD2684	Approved
0.7448	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4236	Phase 3
0.7447	Intermediate Similarity	NPD4237	Approved
0.7438	Intermediate Similarity	NPD968	Approved
0.7431	Intermediate Similarity	NPD4123	Phase 3
0.7426	Intermediate Similarity	NPD2674	Phase 3
0.7424	Intermediate Similarity	NPD2922	Phase 1
0.7417	Intermediate Similarity	NPD6234	Discontinued
0.7414	Intermediate Similarity	NPD2860	Approved
0.7414	Intermediate Similarity	NPD2859	Approved
0.74	Intermediate Similarity	NPD4966	Approved
0.74	Intermediate Similarity	NPD4967	Phase 2
0.74	Intermediate Similarity	NPD4965	Approved
0.7398	Intermediate Similarity	NPD4750	Phase 3
0.7388	Intermediate Similarity	NPD9494	Approved
0.7386	Intermediate Similarity	NPD6232	Discontinued
0.7379	Intermediate Similarity	NPD1512	Approved
0.7373	Intermediate Similarity	NPD3020	Approved
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7372	Intermediate Similarity	NPD1240	Approved
0.7361	Intermediate Similarity	NPD5297	Approved
0.736	Intermediate Similarity	NPD7843	Approved
0.7353	Intermediate Similarity	NPD5111	Phase 2
0.7353	Intermediate Similarity	NPD5110	Phase 2
0.7353	Intermediate Similarity	NPD5109	Approved
0.7351	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1091	Approved
0.7323	Intermediate Similarity	NPD7157	Approved
0.7323	Intermediate Similarity	NPD6671	Approved
0.7319	Intermediate Similarity	NPD230	Phase 1
0.7313	Intermediate Similarity	NPD6584	Phase 3
0.7305	Intermediate Similarity	NPD7266	Discontinued
0.729	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6166	Phase 2
0.729	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1510	Phase 2
0.7285	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1607	Approved
0.726	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5451	Approved
0.725	Intermediate Similarity	NPD291	Approved
0.7244	Intermediate Similarity	NPD7473	Discontinued
0.7237	Intermediate Similarity	NPD4055	Discovery
0.7236	Intermediate Similarity	NPD290	Approved
0.7236	Intermediate Similarity	NPD1358	Approved
0.723	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5718	Phase 2
0.7219	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7199	Phase 2
0.7203	Intermediate Similarity	NPD5177	Phase 3
0.7192	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7447	Phase 1
0.7161	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7212	Phase 2
0.7123	Intermediate Similarity	NPD7213	Phase 3
0.7122	Intermediate Similarity	NPD2238	Phase 2
0.7121	Intermediate Similarity	NPD3847	Discontinued
0.7115	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2935	Discontinued
0.7113	Intermediate Similarity	NPD6100	Approved
0.7113	Intermediate Similarity	NPD6099	Approved
0.7107	Intermediate Similarity	NPD7472	Approved
0.7107	Intermediate Similarity	NPD7074	Phase 3
0.7103	Intermediate Similarity	NPD6190	Approved
0.7103	Intermediate Similarity	NPD5241	Discontinued
0.7092	Intermediate Similarity	NPD6896	Approved
0.7092	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4536	Approved
0.7092	Intermediate Similarity	NPD6895	Approved
0.7092	Intermediate Similarity	NPD4538	Approved
0.709	Intermediate Similarity	NPD6582	Phase 2
0.709	Intermediate Similarity	NPD6583	Phase 3
0.7089	Intermediate Similarity	NPD3818	Discontinued
0.7089	Intermediate Similarity	NPD7228	Approved
0.7087	Intermediate Similarity	NPD5535	Approved
0.7083	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4162	Approved
0.7077	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1424	Approved
0.7067	Intermediate Similarity	NPD4380	Phase 2
0.7063	Intermediate Similarity	NPD1375	Discontinued
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5846	Approved
0.7045	Intermediate Similarity	NPD6516	Phase 2
0.7045	Intermediate Similarity	NPD2668	Approved
0.7045	Intermediate Similarity	NPD4626	Approved
0.7045	Intermediate Similarity	NPD2667	Approved
0.7044	Intermediate Similarity	NPD5844	Phase 1
0.7039	Intermediate Similarity	NPD2977	Approved
0.7039	Intermediate Similarity	NPD2978	Approved
0.7037	Intermediate Similarity	NPD8651	Approved
0.7034	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3892	Phase 2
0.7034	Intermediate Similarity	NPD4110	Phase 3
0.7034	Intermediate Similarity	NPD6331	Phase 2
0.7034	Intermediate Similarity	NPD3750	Approved
0.7023	Intermediate Similarity	NPD7534	Approved
0.7023	Intermediate Similarity	NPD7533	Approved
0.702	Intermediate Similarity	NPD5089	Approved
0.702	Intermediate Similarity	NPD5090	Approved
0.7016	Intermediate Similarity	NPD3134	Approved
0.7015	Intermediate Similarity	NPD2233	Approved
0.7015	Intermediate Similarity	NPD2232	Approved
0.7015	Intermediate Similarity	NPD2230	Approved
0.7015	Intermediate Similarity	NPD1608	Approved
0.7014	Intermediate Similarity	NPD1549	Phase 2
0.7007	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD943	Approved
0.6993	Remote Similarity	NPD1551	Phase 2
0.6991	Remote Similarity	NPD111	Approved
0.6975	Remote Similarity	NPD7808	Phase 3
0.697	Remote Similarity	NPD1651	Approved
0.6966	Remote Similarity	NPD1652	Phase 2
0.6966	Remote Similarity	NPD6674	Discontinued
0.6963	Remote Similarity	NPD1669	Approved
0.6957	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9094	Approved
0.6957	Remote Similarity	NPD6797	Phase 2
0.6953	Remote Similarity	NPD821	Approved
0.695	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.695	Remote Similarity	NPD447	Suspended
0.695	Remote Similarity	NPD3657	Discovery
0.695	Remote Similarity	NPD5124	Phase 1
0.695	Remote Similarity	NPD4340	Discontinued
0.6948	Remote Similarity	NPD6788	Approved
0.6944	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4624	Approved
0.6933	Remote Similarity	NPD3686	Approved
0.6933	Remote Similarity	NPD3687	Approved
0.6929	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6233	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