NPASS Compound

Structure

NPC245120 OpenBabel07101718302D 24 25 0 0 0 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 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 5.1962 -4.0000 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 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 6.0622 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 -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 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 13 19 1 0 0 0 0 14 24 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	334.421
LogP:	2.672
LogD:	3.043
LogS:	-4.203
# Rotatable Bonds:	7
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	2.097
Fsp3:	0.167
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:	-4.785
MDCK Permeability:	1.753566539264284e-05
Pgp-inhibitor:	0.123
Pgp-substrate:	0.843
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	92.15596771240234%
Volume Distribution (VD):	0.318
Pgp-substrate:	6.650397300720215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.462
CYP2C9-inhibitor:	0.755
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.575
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.368

ADMET: Excretion

Clearance (CL):	10.843
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.323
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.591
Skin Sensitization:	0.956
Carcinogencity:	0.23
Eye Corrosion:	0.075
Eye Irritation:	0.907
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC245120

Natural Product ID:	NPC245120
*Common Name:**	(E)-3-Hydroxyphenyl 3-(3,4,5-Trimethoxyphenyl)Acrylate
IUPAC Name:	(3-hydroxyphenyl) (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	SOHZHPMUAVPDTB-BQYQJAHWSA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-21-15-9-12(10-16(22-2)18(15)23-3)7-8-17(20)24-14-6-4-5-13(19)11-14/h4-11,19H,1-3H3/b8-7+
SMILES:	COc1cc(/C=C/C(=O)Oc2cccc(c2)O)cc(c1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400718
PubChem CID:	23656637
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO33086	bermuda buttercup	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17922549]

☑ 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
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	=	10.0	%	PMID[480516]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	>=	80.0	%	PMID[480516]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	=	60.0	%	PMID[480516]

☑ 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 NPC245120 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	316
0.1-0.2	1798
0.2-0.3	5492
0.3-0.4	12264
0.4-0.5	4821
0.5-0.6	4330
0.6-0.7	6582
0.7-0.8	6289
0.8-0.85	612
0.85-0.9	179
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC111635
0.9685	High Similarity	NPC5423
0.96	High Similarity	NPC194841
0.9237	High Similarity	NPC92830
0.9219	High Similarity	NPC109275
0.9213	High Similarity	NPC127604
0.916	High Similarity	NPC36490
0.9147	High Similarity	NPC48315
0.9134	High Similarity	NPC300326
0.9134	High Similarity	NPC58279
0.912	High Similarity	NPC310373
0.9104	High Similarity	NPC164148
0.9104	High Similarity	NPC43500
0.9077	High Similarity	NPC19242
0.907	High Similarity	NPC474651
0.907	High Similarity	NPC474623
0.9048	High Similarity	NPC288238
0.904	High Similarity	NPC166759
0.903	High Similarity	NPC95162
0.903	High Similarity	NPC76336
0.903	High Similarity	NPC148835
0.903	High Similarity	NPC20511
0.903	High Similarity	NPC52086
0.903	High Similarity	NPC474886
0.903	High Similarity	NPC139548
0.9008	High Similarity	NPC73738
0.8993	High Similarity	NPC476347
0.8992	High Similarity	NPC210355
0.8984	High Similarity	NPC27352
0.8978	High Similarity	NPC34245
0.8978	High Similarity	NPC110067
0.8978	High Similarity	NPC256555
0.8978	High Similarity	NPC7439
0.8978	High Similarity	NPC91492
0.8963	High Similarity	NPC13067
0.896	High Similarity	NPC474565
0.896	High Similarity	NPC222175
0.8955	High Similarity	NPC126682
0.8955	High Similarity	NPC82271
0.8955	High Similarity	NPC471719
0.8947	High Similarity	NPC309744
0.8929	High Similarity	NPC476348
0.8929	High Similarity	NPC187398
0.8923	High Similarity	NPC210674
0.8921	High Similarity	NPC287275
0.8906	High Similarity	NPC246704
0.8898	High Similarity	NPC473411
0.8898	High Similarity	NPC262253
0.8898	High Similarity	NPC71579
0.8897	High Similarity	NPC267291
0.8889	High Similarity	NPC126206
0.8872	High Similarity	NPC36437
0.8872	High Similarity	NPC241341
0.8872	High Similarity	NPC233018
0.8865	High Similarity	NPC30688
0.8865	High Similarity	NPC176903
0.8857	High Similarity	NPC178129
0.8857	High Similarity	NPC231149
0.8837	High Similarity	NPC289459
0.8832	High Similarity	NPC300611
0.8832	High Similarity	NPC224876
0.8832	High Similarity	NPC83375
0.8828	High Similarity	NPC282496
0.8828	High Similarity	NPC238810
0.8828	High Similarity	NPC233526
0.8828	High Similarity	NPC108545
0.8819	High Similarity	NPC145780
0.8815	High Similarity	NPC471665
0.8815	High Similarity	NPC286843
0.8815	High Similarity	NPC471664
0.8806	High Similarity	NPC135127
0.8803	High Similarity	NPC294522
0.8803	High Similarity	NPC120426
0.8803	High Similarity	NPC205727
0.8803	High Similarity	NPC21184
0.88	High Similarity	NPC124916
0.8797	High Similarity	NPC137669
0.8794	High Similarity	NPC478237
0.8794	High Similarity	NPC139839
0.8788	High Similarity	NPC79184
0.8788	High Similarity	NPC307042
0.8788	High Similarity	NPC240722
0.8788	High Similarity	NPC476399
0.8788	High Similarity	NPC472338
0.8788	High Similarity	NPC244799
0.8769	High Similarity	NPC120225
0.8769	High Similarity	NPC213552
0.8768	High Similarity	NPC278469
0.8768	High Similarity	NPC193722
0.876	High Similarity	NPC140521
0.876	High Similarity	NPC122792
0.876	High Similarity	NPC228972
0.8741	High Similarity	NPC234865
0.874	High Similarity	NPC472596
0.874	High Similarity	NPC199023
0.8732	High Similarity	NPC475250
0.8732	High Similarity	NPC106138
0.8731	High Similarity	NPC26673
0.873	High Similarity	NPC37858
0.8723	High Similarity	NPC15577
0.8722	High Similarity	NPC472597
0.8712	High Similarity	NPC222004
0.8712	High Similarity	NPC190629
0.8712	High Similarity	NPC3439
0.8712	High Similarity	NPC285339
0.8712	High Similarity	NPC27239
0.8712	High Similarity	NPC470258
0.8712	High Similarity	NPC226788
0.8712	High Similarity	NPC210623
0.8712	High Similarity	NPC273295
0.8712	High Similarity	NPC123127
0.8712	High Similarity	NPC218856
0.8712	High Similarity	NPC202582
0.8705	High Similarity	NPC138212
0.8705	High Similarity	NPC6568
0.8702	High Similarity	NPC470699
0.8702	High Similarity	NPC474119
0.8692	High Similarity	NPC233410
0.8692	High Similarity	NPC116907
0.8692	High Similarity	NPC57490
0.8692	High Similarity	NPC208950
0.8692	High Similarity	NPC299584
0.8692	High Similarity	NPC221077
0.8692	High Similarity	NPC117214
0.8692	High Similarity	NPC203133
0.8692	High Similarity	NPC475169
0.8692	High Similarity	NPC17943
0.8692	High Similarity	NPC193544
0.8692	High Similarity	NPC82483
0.8692	High Similarity	NPC105925
0.8692	High Similarity	NPC472093
0.8692	High Similarity	NPC249836
0.8692	High Similarity	NPC251855
0.8692	High Similarity	NPC298757
0.8692	High Similarity	NPC271985
0.8692	High Similarity	NPC265483
0.8681	High Similarity	NPC163598
0.8681	High Similarity	NPC120774
0.8681	High Similarity	NPC264875
0.8672	High Similarity	NPC75713
0.8667	High Similarity	NPC474600
0.8667	High Similarity	NPC249791
0.8667	High Similarity	NPC476387
0.8667	High Similarity	NPC119060
0.8667	High Similarity	NPC237594
0.8662	High Similarity	NPC93924
0.8662	High Similarity	NPC48366
0.8661	High Similarity	NPC232084
0.8661	High Similarity	NPC61516
0.8661	High Similarity	NPC247364
0.8661	High Similarity	NPC10932
0.8657	High Similarity	NPC35932
0.8657	High Similarity	NPC160991
0.8657	High Similarity	NPC184447
0.8657	High Similarity	NPC319969
0.8657	High Similarity	NPC7903
0.8657	High Similarity	NPC16208
0.8657	High Similarity	NPC137949
0.8652	High Similarity	NPC268515
0.8652	High Similarity	NPC40222
0.8651	High Similarity	NPC277460
0.8647	High Similarity	NPC214860
0.8643	High Similarity	NPC471763
0.8643	High Similarity	NPC185127
0.864	High Similarity	NPC123948
0.8636	High Similarity	NPC110313
0.8633	High Similarity	NPC157816
0.8626	High Similarity	NPC44748
0.8626	High Similarity	NPC78974
0.8626	High Similarity	NPC223136
0.8626	High Similarity	NPC214406
0.8626	High Similarity	NPC18924
0.8626	High Similarity	NPC181361
0.8626	High Similarity	NPC103823
0.8626	High Similarity	NPC28730
0.8615	High Similarity	NPC78446
0.8613	High Similarity	NPC38874
0.8605	High Similarity	NPC261661
0.8603	High Similarity	NPC224941
0.8603	High Similarity	NPC311430
0.8603	High Similarity	NPC472521
0.8594	High Similarity	NPC189844
0.8594	High Similarity	NPC109083
0.8594	High Similarity	NPC60962
0.8594	High Similarity	NPC204466
0.8594	High Similarity	NPC14007
0.8594	High Similarity	NPC269843
0.8594	High Similarity	NPC224814
0.8593	High Similarity	NPC168059
0.8593	High Similarity	NPC229442
0.8593	High Similarity	NPC36661
0.8593	High Similarity	NPC475840
0.8593	High Similarity	NPC277021
0.8593	High Similarity	NPC474810
0.8592	High Similarity	NPC183083
0.8592	High Similarity	NPC137352
0.8583	High Similarity	NPC226629
0.8582	High Similarity	NPC469613
0.8582	High Similarity	NPC469625
0.8582	High Similarity	NPC125617

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 NPC245120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	942
0.2-0.3	1840
0.3-0.4	2789
0.4-0.5	1632
0.5-0.6	978
0.6-0.7	549
0.7-0.8	135
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8433	Intermediate Similarity	NPD3027	Phase 3
0.8397	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD422	Phase 1
0.8345	Intermediate Similarity	NPD1653	Approved
0.8258	Intermediate Similarity	NPD2983	Phase 2
0.8258	Intermediate Similarity	NPD2982	Phase 2
0.8222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2981	Phase 2
0.8148	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD5536	Phase 2
0.8116	Intermediate Similarity	NPD1613	Approved
0.8116	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD4357	Discontinued
0.8015	Intermediate Similarity	NPD3018	Phase 2
0.7971	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD3882	Suspended
0.7947	Intermediate Similarity	NPD2801	Approved
0.7895	Intermediate Similarity	NPD3817	Phase 2
0.7881	Intermediate Similarity	NPD1934	Approved
0.7826	Intermediate Similarity	NPD4908	Phase 1
0.7823	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1548	Phase 1
0.7801	Intermediate Similarity	NPD230	Phase 1
0.7801	Intermediate Similarity	NPD447	Suspended
0.7799	Intermediate Similarity	NPD5844	Phase 1
0.7785	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7266	Discontinued
0.7778	Intermediate Similarity	NPD1358	Approved
0.774	Intermediate Similarity	NPD3750	Approved
0.773	Intermediate Similarity	NPD4060	Phase 1
0.7718	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1465	Phase 2
0.7712	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1551	Phase 2
0.7704	Intermediate Similarity	NPD1610	Phase 2
0.7703	Intermediate Similarity	NPD6799	Approved
0.7703	Intermediate Similarity	NPD1511	Approved
0.7692	Intermediate Similarity	NPD5283	Phase 1
0.7676	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD5124	Phase 1
0.7674	Intermediate Similarity	NPD228	Approved
0.7671	Intermediate Similarity	NPD1652	Phase 2
0.7664	Intermediate Similarity	NPD3225	Approved
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4628	Phase 3
0.7615	Intermediate Similarity	NPD5535	Approved
0.7607	Intermediate Similarity	NPD7549	Discontinued
0.76	Intermediate Similarity	NPD1512	Approved
0.7595	Intermediate Similarity	NPD6232	Discontinued
0.7568	Intermediate Similarity	NPD6190	Approved
0.7564	Intermediate Similarity	NPD7075	Discontinued
0.7559	Intermediate Similarity	NPD3134	Approved
0.7552	Intermediate Similarity	NPD4340	Discontinued
0.7532	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD37	Approved
0.7518	Intermediate Similarity	NPD4625	Phase 3
0.7518	Intermediate Similarity	NPD7095	Approved
0.7516	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD4675	Approved
0.7516	Intermediate Similarity	NPD4678	Approved
0.7516	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7819	Suspended
0.7484	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1558	Phase 1
0.7482	Intermediate Similarity	NPD2797	Approved
0.7482	Intermediate Similarity	NPD1203	Approved
0.7469	Intermediate Similarity	NPD7054	Approved
0.7466	Intermediate Similarity	NPD2935	Discontinued
0.7464	Intermediate Similarity	NPD4749	Approved
0.7453	Intermediate Similarity	NPD7473	Discontinued
0.7447	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1242	Phase 1
0.7438	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1933	Approved
0.7423	Intermediate Similarity	NPD7472	Approved
0.7423	Intermediate Similarity	NPD7074	Phase 3
0.7417	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3540	Phase 1
0.7405	Intermediate Similarity	NPD919	Approved
0.7403	Intermediate Similarity	NPD6599	Discontinued
0.7397	Intermediate Similarity	NPD3748	Approved
0.7394	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1608	Approved
0.7389	Intermediate Similarity	NPD7768	Phase 2
0.7386	Intermediate Similarity	NPD3686	Approved
0.7386	Intermediate Similarity	NPD3687	Approved
0.7383	Intermediate Similarity	NPD4110	Phase 3
0.7383	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD9494	Approved
0.7365	Intermediate Similarity	NPD1549	Phase 2
0.7361	Intermediate Similarity	NPD1240	Approved
0.7358	Intermediate Similarity	NPD5677	Discontinued
0.7355	Intermediate Similarity	NPD7411	Suspended
0.7353	Intermediate Similarity	NPD1357	Approved
0.7351	Intermediate Similarity	NPD5297	Approved
0.7347	Intermediate Similarity	NPD3539	Phase 1
0.7343	Intermediate Similarity	NPD3268	Approved
0.7342	Intermediate Similarity	NPD6971	Discontinued
0.7333	Intermediate Similarity	NPD2219	Phase 1
0.7325	Intermediate Similarity	NPD5402	Approved
0.732	Intermediate Similarity	NPD5403	Approved
0.7319	Intermediate Similarity	NPD3705	Approved
0.7315	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6801	Discontinued
0.7299	Intermediate Similarity	NPD4626	Approved
0.7299	Intermediate Similarity	NPD1778	Approved
0.7297	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6233	Phase 2
0.7289	Intermediate Similarity	NPD7808	Phase 3
0.7279	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD6797	Phase 2
0.7266	Intermediate Similarity	NPD9717	Approved
0.726	Intermediate Similarity	NPD1607	Approved
0.7255	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2861	Phase 2
0.725	Intermediate Similarity	NPD5494	Approved
0.7233	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2796	Approved
0.7229	Intermediate Similarity	NPD7251	Discontinued
0.7226	Intermediate Similarity	NPD5585	Approved
0.7222	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD5242	Approved
0.7222	Intermediate Similarity	NPD1296	Phase 2
0.7219	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5353	Approved
0.7209	Intermediate Similarity	NPD9697	Approved
0.7205	Intermediate Similarity	NPD8127	Discontinued
0.7203	Intermediate Similarity	NPD6832	Phase 2
0.7195	Intermediate Similarity	NPD7228	Approved
0.7194	Intermediate Similarity	NPD1535	Discovery
0.7194	Intermediate Similarity	NPD1091	Approved
0.7192	Intermediate Similarity	NPD6355	Discontinued
0.7192	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5401	Approved
0.719	Intermediate Similarity	NPD4123	Phase 3
0.7179	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD2684	Approved
0.7174	Intermediate Similarity	NPD17	Approved
0.7172	Intermediate Similarity	NPD4062	Phase 3
0.7162	Intermediate Similarity	NPD4308	Phase 3
0.7154	Intermediate Similarity	NPD968	Approved
0.7153	Intermediate Similarity	NPD9545	Approved
0.7153	Intermediate Similarity	NPD1894	Discontinued
0.7152	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2653	Approved
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7134	Intermediate Similarity	NPD6386	Approved
0.7134	Intermediate Similarity	NPD6385	Approved
0.7126	Intermediate Similarity	NPD7039	Approved
0.7126	Intermediate Similarity	NPD7038	Approved
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7125	Intermediate Similarity	NPD3749	Approved
0.7123	Intermediate Similarity	NPD4140	Approved
0.7122	Intermediate Similarity	NPD3847	Discontinued
0.7121	Intermediate Similarity	NPD3021	Approved
0.7121	Intermediate Similarity	NPD3022	Approved
0.7117	Intermediate Similarity	NPD3926	Phase 2
0.7114	Intermediate Similarity	NPD6099	Approved
0.7114	Intermediate Similarity	NPD6100	Approved
0.7103	Intermediate Similarity	NPD411	Approved
0.7101	Intermediate Similarity	NPD9268	Approved
0.7101	Intermediate Similarity	NPD5691	Approved
0.709	Intermediate Similarity	NPD7843	Approved
0.7086	Intermediate Similarity	NPD3060	Approved
0.7083	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5762	Approved
0.7067	Intermediate Similarity	NPD5763	Approved
0.7063	Intermediate Similarity	NPD6584	Phase 3
0.7059	Intermediate Similarity	NPD7124	Phase 2
0.7059	Intermediate Similarity	NPD6671	Approved
0.7059	Intermediate Similarity	NPD7157	Approved
0.7047	Intermediate Similarity	NPD2799	Discontinued
0.7047	Intermediate Similarity	NPD7033	Discontinued
0.7027	Intermediate Similarity	NPD6653	Approved
0.7025	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5090	Approved
0.7025	Intermediate Similarity	NPD5089	Approved
0.7024	Intermediate Similarity	NPD7685	Pre-registration
0.7007	Intermediate Similarity	NPD943	Approved
0.7006	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4005	Discontinued
0.7	Intermediate Similarity	NPD6032	Approved
0.7	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8443	Clinical (unspecified phase)

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