NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	326.1
Volume:	308.023
LogP:	0.008
LogD:	-0.118
LogS:	-0.712
# Rotatable Bonds:	5
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	3.581
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.835
MDCK Permeability:	2.7882950234925374e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.534
Human Intestinal Absorption (HIA):	0.866
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	78.3450927734375%
Volume Distribution (VD):	0.431
Pgp-substrate:	29.23053741455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.722
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	2.347
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.291
Rat Oral Acute Toxicity:	0.659
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.925
Carcinogencity:	0.232
Eye Corrosion:	0.003
Eye Irritation:	0.067
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC476872

Natural Product ID:	NPC476872
*Common Name:**	6-O-(e)-p-coumaroyl glucopyranose
IUPAC Name:	[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	GKUSDFCBGXFHIL-CXXZEMTDSA-N
Standard InCHI:	InChI=1S/C15H18O8/c16-9-4-1-8(2-5-9)3-6-11(17)22-7-10-12(18)13(19)14(20)15(21)23-10/h1-6,10,12-16,18-21H,7H2/b6-3+/t10-,12-,13+,14-,15?/m1/s1
SMILES:	C1=CC(=CC=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H](C(O2)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10087731
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO33548	Clematis tashiroi	Species	Ranunculaceae	Eukaryota	aerial parts	Heping District, Taichung City, Taiwan	2012-AUG	PMID[26143931]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	5	%	PMID[26143931]

☑ 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 NPC476872 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	256
0.1-0.2	1205
0.2-0.3	3469
0.3-0.4	8687
0.4-0.5	9998
0.5-0.6	7253
0.6-0.7	9771
0.7-0.8	1714
0.8-0.85	256
0.85-0.9	50
0.9-0.95	35
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC11724
0.9826	High Similarity	NPC52097
0.9576	High Similarity	NPC126991
0.9576	High Similarity	NPC83218
0.9496	High Similarity	NPC471157
0.9496	High Similarity	NPC252114
0.9417	High Similarity	NPC173150
0.9417	High Similarity	NPC45224
0.9417	High Similarity	NPC471882
0.9417	High Similarity	NPC106677
0.9417	High Similarity	NPC471881
0.9417	High Similarity	NPC476873
0.9417	High Similarity	NPC35288
0.9417	High Similarity	NPC288416
0.9417	High Similarity	NPC156692
0.9339	High Similarity	NPC225307
0.9339	High Similarity	NPC232880
0.9262	High Similarity	NPC477294
0.9262	High Similarity	NPC229784
0.9262	High Similarity	NPC253595
0.9262	High Similarity	NPC477293
0.9211	High Similarity	NPC313193
0.9174	High Similarity	NPC61181
0.9113	High Similarity	NPC281798
0.9113	High Similarity	NPC138777
0.9113	High Similarity	NPC46137
0.9113	High Similarity	NPC478255
0.9113	High Similarity	NPC225384
0.9113	High Similarity	NPC219677
0.9113	High Similarity	NPC254819
0.9113	High Similarity	NPC235294
0.9113	High Similarity	NPC246869
0.9098	High Similarity	NPC103533
0.9052	High Similarity	NPC175771
0.904	High Similarity	NPC473924
0.904	High Similarity	NPC473285
0.8968	High Similarity	NPC254398
0.8968	High Similarity	NPC28637
0.8898	High Similarity	NPC471883
0.8898	High Similarity	NPC886
0.8898	High Similarity	NPC34293
0.8898	High Similarity	NPC287597
0.8879	High Similarity	NPC157338
0.8871	High Similarity	NPC146540
0.8828	High Similarity	NPC476870
0.8828	High Similarity	NPC263829
0.8819	High Similarity	NPC114116
0.88	High Similarity	NPC295970
0.876	High Similarity	NPC470572
0.876	High Similarity	NPC471345
0.876	High Similarity	NPC157554
0.876	High Similarity	NPC166180
0.876	High Similarity	NPC472132
0.876	High Similarity	NPC186418
0.875	High Similarity	NPC169398
0.8729	High Similarity	NPC148055
0.8692	High Similarity	NPC260425
0.8692	High Similarity	NPC78363
0.8692	High Similarity	NPC476376
0.8626	High Similarity	NPC321638
0.8626	High Similarity	NPC205195
0.8626	High Similarity	NPC321184
0.8626	High Similarity	NPC220942
0.8626	High Similarity	NPC226005
0.8626	High Similarity	NPC171134
0.8626	High Similarity	NPC197316
0.8626	High Similarity	NPC89105
0.8626	High Similarity	NPC328273
0.8626	High Similarity	NPC49597
0.8626	High Similarity	NPC220936
0.8626	High Similarity	NPC81515
0.8626	High Similarity	NPC31745
0.8626	High Similarity	NPC100389
0.8626	High Similarity	NPC476383
0.8626	High Similarity	NPC68092
0.8626	High Similarity	NPC64141
0.8626	High Similarity	NPC472350
0.8615	High Similarity	NPC37468
0.8595	High Similarity	NPC469702
0.8595	High Similarity	NPC282409
0.8561	High Similarity	NPC202700
0.855	High Similarity	NPC65262
0.855	High Similarity	NPC101686
0.855	High Similarity	NPC469364
0.8538	High Similarity	NPC185778
0.8525	High Similarity	NPC269242
0.8525	High Similarity	NPC476448
0.8525	High Similarity	NPC469703
0.8525	High Similarity	NPC476445
0.8525	High Similarity	NPC160854
0.8525	High Similarity	NPC469704
0.8525	High Similarity	NPC469548
0.8525	High Similarity	NPC201402
0.8522	High Similarity	NPC184633
0.8504	High Similarity	NPC469549
0.8496	Intermediate Similarity	NPC186406
0.8496	Intermediate Similarity	NPC134405
0.8496	Intermediate Similarity	NPC476377
0.8496	Intermediate Similarity	NPC476385
0.8496	Intermediate Similarity	NPC47471
0.8496	Intermediate Similarity	NPC46644
0.848	Intermediate Similarity	NPC123704
0.8473	Intermediate Similarity	NPC103409
0.8468	Intermediate Similarity	NPC474275
0.8468	Intermediate Similarity	NPC212176
0.8468	Intermediate Similarity	NPC224208
0.8455	Intermediate Similarity	NPC55608
0.8455	Intermediate Similarity	NPC469686
0.8455	Intermediate Similarity	NPC266045
0.8443	Intermediate Similarity	NPC60589
0.8443	Intermediate Similarity	NPC469708
0.8433	Intermediate Similarity	NPC140502
0.8433	Intermediate Similarity	NPC222433
0.8433	Intermediate Similarity	NPC157816
0.8433	Intermediate Similarity	NPC145319
0.8433	Intermediate Similarity	NPC265648
0.8421	Intermediate Similarity	NPC475530
0.8421	Intermediate Similarity	NPC473799
0.8387	Intermediate Similarity	NPC471067
0.8374	Intermediate Similarity	NPC198734
0.8374	Intermediate Similarity	NPC469412
0.837	Intermediate Similarity	NPC40305
0.837	Intermediate Similarity	NPC269141
0.837	Intermediate Similarity	NPC476380
0.837	Intermediate Similarity	NPC105005
0.837	Intermediate Similarity	NPC247032
0.837	Intermediate Similarity	NPC476397
0.837	Intermediate Similarity	NPC476378
0.837	Intermediate Similarity	NPC112
0.837	Intermediate Similarity	NPC298257
0.837	Intermediate Similarity	NPC478239
0.837	Intermediate Similarity	NPC175214
0.837	Intermediate Similarity	NPC264632
0.837	Intermediate Similarity	NPC76406
0.837	Intermediate Similarity	NPC204644
0.837	Intermediate Similarity	NPC205864
0.837	Intermediate Similarity	NPC476375
0.837	Intermediate Similarity	NPC478250
0.837	Intermediate Similarity	NPC476381
0.837	Intermediate Similarity	NPC96795
0.837	Intermediate Similarity	NPC119537
0.837	Intermediate Similarity	NPC476384
0.837	Intermediate Similarity	NPC293154
0.8358	Intermediate Similarity	NPC7518
0.8358	Intermediate Similarity	NPC154262
0.8358	Intermediate Similarity	NPC159387
0.8358	Intermediate Similarity	NPC137501
0.832	Intermediate Similarity	NPC232454
0.832	Intermediate Similarity	NPC178449
0.832	Intermediate Similarity	NPC470907
0.8319	Intermediate Similarity	NPC474641
0.8309	Intermediate Similarity	NPC473281
0.8309	Intermediate Similarity	NPC110063
0.8309	Intermediate Similarity	NPC63304
0.8309	Intermediate Similarity	NPC300894
0.8309	Intermediate Similarity	NPC296659
0.8309	Intermediate Similarity	NPC297342
0.8309	Intermediate Similarity	NPC251062
0.8309	Intermediate Similarity	NPC202391
0.8309	Intermediate Similarity	NPC476867
0.8309	Intermediate Similarity	NPC184464
0.8309	Intermediate Similarity	NPC141455
0.8309	Intermediate Similarity	NPC232228
0.8309	Intermediate Similarity	NPC196063
0.8309	Intermediate Similarity	NPC296954
0.8309	Intermediate Similarity	NPC292443
0.8309	Intermediate Similarity	NPC77922
0.8309	Intermediate Similarity	NPC64195
0.8305	Intermediate Similarity	NPC470825
0.8296	Intermediate Similarity	NPC296643
0.8276	Intermediate Similarity	NPC260952
0.8271	Intermediate Similarity	NPC124149
0.8268	Intermediate Similarity	NPC233559
0.8264	Intermediate Similarity	NPC473556
0.8264	Intermediate Similarity	NPC301651
0.8258	Intermediate Similarity	NPC55040
0.8254	Intermediate Similarity	NPC287429
0.825	Intermediate Similarity	NPC217472
0.8248	Intermediate Similarity	NPC262182
0.8248	Intermediate Similarity	NPC476869
0.8248	Intermediate Similarity	NPC476866
0.8248	Intermediate Similarity	NPC476868
0.8248	Intermediate Similarity	NPC475528
0.8248	Intermediate Similarity	NPC100998
0.8248	Intermediate Similarity	NPC216819
0.8248	Intermediate Similarity	NPC34927
0.8248	Intermediate Similarity	NPC287615
0.8248	Intermediate Similarity	NPC476382
0.8248	Intermediate Similarity	NPC476864
0.8248	Intermediate Similarity	NPC83743
0.8248	Intermediate Similarity	NPC34587
0.8248	Intermediate Similarity	NPC252292
0.8246	Intermediate Similarity	NPC304638
0.824	Intermediate Similarity	NPC476142
0.8235	Intermediate Similarity	NPC116104
0.8235	Intermediate Similarity	NPC302286
0.8235	Intermediate Similarity	NPC186296
0.8235	Intermediate Similarity	NPC475213
0.8235	Intermediate Similarity	NPC152796
0.8235	Intermediate Similarity	NPC237872

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 NPC476872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	742
0.2-0.3	1592
0.3-0.4	3010
0.4-0.5	1934
0.5-0.6	1233
0.6-0.7	410
0.7-0.8	13
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8626	High Similarity	NPD7266	Discontinued
0.816	Intermediate Similarity	NPD1091	Approved
0.8014	Intermediate Similarity	NPD1653	Approved
0.7815	Intermediate Similarity	NPD1358	Approved
0.7714	Intermediate Similarity	NPD6190	Approved
0.7705	Intermediate Similarity	NPD969	Suspended
0.7698	Intermediate Similarity	NPD9545	Approved
0.7447	Intermediate Similarity	NPD1652	Phase 2
0.7438	Intermediate Similarity	NPD3134	Approved
0.7351	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD422	Phase 1
0.7319	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7194	Intermediate Similarity	NPD4340	Discontinued
0.7153	Intermediate Similarity	NPD3027	Phase 3
0.7152	Intermediate Similarity	NPD8455	Phase 2
0.7122	Intermediate Similarity	NPD1613	Approved
0.7122	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1357	Approved
0.7097	Intermediate Similarity	NPD290	Approved
0.7097	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7097	Phase 1
0.709	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7843	Approved
0.7071	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5124	Phase 1
0.7067	Intermediate Similarity	NPD4380	Phase 2
0.705	Intermediate Similarity	NPD6233	Phase 2
0.7043	Intermediate Similarity	NPD689	Discontinued
0.704	Intermediate Similarity	NPD2684	Approved
0.7019	Intermediate Similarity	NPD7685	Pre-registration
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3764	Approved
0.6948	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7157	Approved
0.6917	Remote Similarity	NPD5126	Approved
0.6917	Remote Similarity	NPD5125	Phase 3
0.6914	Remote Similarity	NPD6559	Discontinued
0.6903	Remote Similarity	NPD7075	Discontinued
0.6894	Remote Similarity	NPD1548	Phase 1
0.6892	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2934	Approved
0.6891	Remote Similarity	NPD2933	Approved
0.6885	Remote Similarity	NPD1242	Phase 1
0.688	Remote Similarity	NPD968	Approved
0.6879	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD3818	Discontinued
0.6871	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5403	Approved
0.6866	Remote Similarity	NPD3496	Discontinued
0.6857	Remote Similarity	NPD6798	Discontinued
0.6857	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD111	Approved
0.6835	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2859	Approved
0.6833	Remote Similarity	NPD2860	Approved
0.6832	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7054	Approved
0.6829	Remote Similarity	NPD846	Approved
0.6829	Remote Similarity	NPD940	Approved
0.6824	Remote Similarity	NPD5058	Phase 3
0.6815	Remote Similarity	NPD1610	Phase 2
0.6815	Remote Similarity	NPD3705	Approved
0.6815	Remote Similarity	NPD1535	Discovery
0.6809	Remote Similarity	NPD4062	Phase 3
0.6803	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9697	Approved
0.679	Remote Similarity	NPD7074	Phase 3
0.679	Remote Similarity	NPD7472	Approved
0.6788	Remote Similarity	NPD3225	Approved
0.6783	Remote Similarity	NPD6653	Approved
0.6781	Remote Similarity	NPD1549	Phase 2
0.6781	Remote Similarity	NPD2424	Discontinued
0.6779	Remote Similarity	NPD6799	Approved
0.677	Remote Similarity	NPD7228	Approved
0.6765	Remote Similarity	NPD1481	Phase 2
0.6765	Remote Similarity	NPD9269	Phase 2
0.6763	Remote Similarity	NPD2861	Phase 2
0.6763	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1551	Phase 2
0.6753	Remote Similarity	NPD6801	Discontinued
0.6753	Remote Similarity	NPD37	Approved
0.6752	Remote Similarity	NPD6234	Discontinued
0.6748	Remote Similarity	NPD6797	Phase 2
0.6744	Remote Similarity	NPD228	Approved
0.6739	Remote Similarity	NPD1203	Approved
0.6736	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4536	Approved
0.6736	Remote Similarity	NPD4538	Approved
0.6735	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3536	Discontinued
0.6733	Remote Similarity	NPD5401	Approved
0.6731	Remote Similarity	NPD4965	Approved
0.6731	Remote Similarity	NPD4967	Phase 2
0.6731	Remote Similarity	NPD4966	Approved
0.6727	Remote Similarity	NPD8313	Approved
0.6727	Remote Similarity	NPD8312	Approved
0.6724	Remote Similarity	NPD1282	Approved
0.6719	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4908	Phase 1
0.6713	Remote Similarity	NPD6355	Discontinued
0.6712	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7251	Discontinued
0.6692	Remote Similarity	NPD5535	Approved
0.6692	Remote Similarity	NPD5536	Phase 2
0.6691	Remote Similarity	NPD5647	Approved
0.6691	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5588	Approved
0.669	Remote Similarity	NPD7033	Discontinued
0.669	Remote Similarity	NPD5960	Phase 3
0.6689	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD7808	Phase 3
0.6644	Remote Similarity	NPD2935	Discontinued
0.6643	Remote Similarity	NPD9494	Approved
0.6642	Remote Similarity	NPD9717	Approved
0.6642	Remote Similarity	NPD1894	Discontinued
0.6641	Remote Similarity	NPD74	Approved
0.6641	Remote Similarity	NPD9266	Approved
0.6641	Remote Similarity	NPD1241	Discontinued
0.6622	Remote Similarity	NPD6674	Discontinued
0.662	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1048	Approved
0.6619	Remote Similarity	NPD3094	Phase 2
0.6618	Remote Similarity	NPD3847	Discontinued
0.6612	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5763	Approved
0.6599	Remote Similarity	NPD5762	Approved
0.6594	Remote Similarity	NPD3685	Discontinued
0.6593	Remote Similarity	NPD9268	Approved
0.6593	Remote Similarity	NPD5691	Approved
0.6589	Remote Similarity	NPD3021	Approved
0.6589	Remote Similarity	NPD3022	Approved
0.6585	Remote Similarity	NPD9495	Approved
0.6581	Remote Similarity	NPD7411	Suspended
0.6579	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3750	Approved
0.6575	Remote Similarity	NPD1510	Phase 2
0.6573	Remote Similarity	NPD520	Approved
0.6562	Remote Similarity	NPD9264	Approved
0.6562	Remote Similarity	NPD9263	Approved
0.6562	Remote Similarity	NPD9267	Approved
0.656	Remote Similarity	NPD291	Approved
0.6558	Remote Similarity	NPD3455	Phase 2
0.6554	Remote Similarity	NPD970	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD3179	Approved
0.6549	Remote Similarity	NPD7095	Approved
0.6549	Remote Similarity	NPD3180	Approved
0.6548	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD8651	Approved
0.6545	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6516	Phase 2
0.6544	Remote Similarity	NPD9381	Approved
0.6544	Remote Similarity	NPD9384	Approved
0.6544	Remote Similarity	NPD5846	Approved
0.6544	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4198	Discontinued
0.6538	Remote Similarity	NPD1934	Approved
0.6536	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5048	Discontinued
0.6531	Remote Similarity	NPD9570	Approved
0.6528	Remote Similarity	NPD1240	Approved
0.6525	Remote Similarity	NPD5736	Approved
0.6516	Remote Similarity	NPD6599	Discontinued
0.6513	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6647	Phase 2
0.65	Remote Similarity	NPD2797	Approved
0.65	Remote Similarity	NPD6362	Approved
0.65	Remote Similarity	NPD9365	Approved
0.6497	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3686	Approved
0.6494	Remote Similarity	NPD3687	Approved
0.6486	Remote Similarity	NPD6004	Phase 3
0.6486	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6005	Phase 3
0.6486	Remote Similarity	NPD6002	Phase 3
0.6483	Remote Similarity	NPD1933	Approved
0.6483	Remote Similarity	NPD447	Suspended
0.6479	Remote Similarity	NPD6832	Phase 2
0.6479	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD2982	Phase 2
0.6475	Remote Similarity	NPD2983	Phase 2
0.6467	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3400	Discontinued
0.6466	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD2629	Approved
0.6462	Remote Similarity	NPD2067	Discontinued
0.6462	Remote Similarity	NPD556	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