NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.08
Volume:	241.503
LogP:	3.036
LogD:	3.097
LogS:	-2.793
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	2.031
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.051
MDCK Permeability:	1.58078419190133e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	98.89696502685547%
Volume Distribution (VD):	0.666
Pgp-substrate:	1.0324749946594238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.932
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.597
CYP2D6-inhibitor:	0.433
CYP2D6-substrate:	0.835
CYP3A4-inhibitor:	0.207
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	15.918
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.393
Drug-inuced Liver Injury (DILI):	0.098
AMES Toxicity:	0.364
Rat Oral Acute Toxicity:	0.659
Maximum Recommended Daily Dose:	0.162
Skin Sensitization:	0.966
Carcinogencity:	0.297
Eye Corrosion:	0.025
Eye Irritation:	0.941
Respiratory Toxicity:	0.439

Download Data

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

Natural Product: NPC176527

Natural Product ID:	NPC176527
*Common Name:**	3,4,5-Trihydroxy-Transstilbene
IUPAC Name:	5-[(E)-2-phenylethenyl]benzene-1,2,3-triol
Synonyms:	3,4,5-Trihydroxy-Transstilbene
Standard InCHIKey:	IYWFOPPYQUEKHN-VOTSOKGWSA-N
Standard InCHI:	InChI=1S/C14H12O3/c15-12-8-11(9-13(16)14(12)17)7-6-10-4-2-1-3-5-10/h1-9,15-17H/b7-6+
SMILES:	Oc1cc(/C=C/c2ccccc2)cc(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455488
PubChem CID:	9964599
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
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	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
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	70.0	%	PMID[559637]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	54.0	%	PMID[559637]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	38.0	%	PMID[559637]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	56.15	%	PMID[559637]
NPT35	Others	n.a.		Time	=	2.9	10'3s	PMID[559638]
NPT35	Others	n.a.		INH	=	1.3	10'4L/mol/s	PMID[559638]
NPT35	Others	n.a.		Time	=	2.4	10'3s	PMID[559638]
NPT35	Others	n.a.		INH	=	3.1	10'4L/mol/s	PMID[559638]

☑ 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 NPC176527 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	444
0.1-0.2	2334
0.2-0.3	9491
0.3-0.4	10525
0.4-0.5	4689
0.5-0.6	7432
0.6-0.7	5831
0.7-0.8	1686
0.8-0.85	193
0.85-0.9	58
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC114392
0.99	High Similarity	NPC58427
0.99	High Similarity	NPC105727
0.99	High Similarity	NPC34864
0.9612	High Similarity	NPC268032
0.9394	High Similarity	NPC161571
0.9394	High Similarity	NPC248573
0.9394	High Similarity	NPC275053
0.92	High Similarity	NPC223393
0.9192	High Similarity	NPC291789
0.9118	High Similarity	NPC30506
0.9074	High Similarity	NPC472893
0.9029	High Similarity	NPC292452
0.9	High Similarity	NPC144343
0.8932	High Similarity	NPC471511
0.8922	High Similarity	NPC143659
0.8922	High Similarity	NPC100340
0.8919	High Similarity	NPC217174
0.8919	High Similarity	NPC226629
0.8909	High Similarity	NPC277588
0.8846	High Similarity	NPC239291
0.8839	High Similarity	NPC10932
0.8839	High Similarity	NPC232084
0.8839	High Similarity	NPC472071
0.8839	High Similarity	NPC61516
0.8839	High Similarity	NPC247364
0.8812	High Similarity	NPC109955
0.88	High Similarity	NPC107522
0.8761	High Similarity	NPC24125
0.875	High Similarity	NPC102216
0.875	High Similarity	NPC191866
0.875	High Similarity	NPC241891
0.875	High Similarity	NPC12278
0.8725	High Similarity	NPC131587
0.8692	High Similarity	NPC202647
0.8684	High Similarity	NPC237667
0.8667	High Similarity	NPC134829
0.8609	High Similarity	NPC71579
0.8609	High Similarity	NPC473411
0.8609	High Similarity	NPC262253
0.8609	High Similarity	NPC41562
0.86	High Similarity	NPC295295
0.8598	High Similarity	NPC233835
0.8585	High Similarity	NPC248904
0.8585	High Similarity	NPC109691
0.8585	High Similarity	NPC470700
0.8585	High Similarity	NPC302681
0.8585	High Similarity	NPC39097
0.8585	High Similarity	NPC118286
0.8585	High Similarity	NPC39664
0.8571	High Similarity	NPC259638
0.8571	High Similarity	NPC119860
0.8558	High Similarity	NPC110764
0.8545	High Similarity	NPC471485
0.8534	High Similarity	NPC136319
0.8534	High Similarity	NPC53567
0.8534	High Similarity	NPC228922
0.8534	High Similarity	NPC84086
0.8534	High Similarity	NPC197757
0.8532	High Similarity	NPC257430
0.8532	High Similarity	NPC179002
0.8532	High Similarity	NPC296920
0.8532	High Similarity	NPC165770
0.8532	High Similarity	NPC187583
0.8532	High Similarity	NPC4493
0.8532	High Similarity	NPC225679
0.8532	High Similarity	NPC476632
0.8532	High Similarity	NPC90520
0.8522	High Similarity	NPC145780
0.8522	High Similarity	NPC39029
0.8519	High Similarity	NPC228343
0.8519	High Similarity	NPC55617
0.8519	High Similarity	NPC254833
0.8519	High Similarity	NPC62258
0.8509	High Similarity	NPC474565
0.8505	High Similarity	NPC54844
0.8491	Intermediate Similarity	NPC474839
0.8491	Intermediate Similarity	NPC246056
0.8482	Intermediate Similarity	NPC193067
0.8476	Intermediate Similarity	NPC196479
0.8468	Intermediate Similarity	NPC120280
0.8462	Intermediate Similarity	NPC228972
0.8462	Intermediate Similarity	NPC122792
0.8462	Intermediate Similarity	NPC10588
0.8462	Intermediate Similarity	NPC206487
0.8462	Intermediate Similarity	NPC166761
0.8462	Intermediate Similarity	NPC5796
0.8455	Intermediate Similarity	NPC43525
0.8455	Intermediate Similarity	NPC166995
0.8455	Intermediate Similarity	NPC280606
0.844	Intermediate Similarity	NPC226401
0.844	Intermediate Similarity	NPC147634
0.844	Intermediate Similarity	NPC120982
0.844	Intermediate Similarity	NPC79793
0.844	Intermediate Similarity	NPC174096
0.8435	Intermediate Similarity	NPC166759
0.8431	Intermediate Similarity	NPC274678
0.8426	Intermediate Similarity	NPC174981
0.8421	Intermediate Similarity	NPC20674
0.8396	Intermediate Similarity	NPC79672
0.8396	Intermediate Similarity	NPC120719
0.8396	Intermediate Similarity	NPC52087
0.839	Intermediate Similarity	NPC203133
0.839	Intermediate Similarity	NPC475169
0.839	Intermediate Similarity	NPC299584
0.839	Intermediate Similarity	NPC82483
0.839	Intermediate Similarity	NPC472093
0.839	Intermediate Similarity	NPC234400
0.839	Intermediate Similarity	NPC265483
0.839	Intermediate Similarity	NPC208950
0.839	Intermediate Similarity	NPC298757
0.839	Intermediate Similarity	NPC60885
0.839	Intermediate Similarity	NPC116907
0.839	Intermediate Similarity	NPC117214
0.839	Intermediate Similarity	NPC221077
0.839	Intermediate Similarity	NPC193544
0.839	Intermediate Similarity	NPC57490
0.839	Intermediate Similarity	NPC251855
0.839	Intermediate Similarity	NPC17943
0.839	Intermediate Similarity	NPC233410
0.8381	Intermediate Similarity	NPC72947
0.8381	Intermediate Similarity	NPC284011
0.8378	Intermediate Similarity	NPC117846
0.8365	Intermediate Similarity	NPC80027
0.8364	Intermediate Similarity	NPC297657
0.8349	Intermediate Similarity	NPC19808
0.8349	Intermediate Similarity	NPC33728
0.8348	Intermediate Similarity	NPC229401
0.8319	Intermediate Similarity	NPC28730
0.8319	Intermediate Similarity	NPC103823
0.8319	Intermediate Similarity	NPC214406
0.8319	Intermediate Similarity	NPC44748
0.8319	Intermediate Similarity	NPC78974
0.8319	Intermediate Similarity	NPC18924
0.8319	Intermediate Similarity	NPC223136
0.8305	Intermediate Similarity	NPC224342
0.8304	Intermediate Similarity	NPC107240
0.8304	Intermediate Similarity	NPC180508
0.8304	Intermediate Similarity	NPC228287
0.8302	Intermediate Similarity	NPC168303
0.8302	Intermediate Similarity	NPC222522
0.8302	Intermediate Similarity	NPC302219
0.8302	Intermediate Similarity	NPC242342
0.8302	Intermediate Similarity	NPC53051
0.8302	Intermediate Similarity	NPC477801
0.8302	Intermediate Similarity	NPC24404
0.8302	Intermediate Similarity	NPC477802
0.8302	Intermediate Similarity	NPC249828
0.8302	Intermediate Similarity	NPC146798
0.8302	Intermediate Similarity	NPC313030
0.8302	Intermediate Similarity	NPC71002
0.8302	Intermediate Similarity	NPC85479
0.8302	Intermediate Similarity	NPC94351
0.8302	Intermediate Similarity	NPC106396
0.8288	Intermediate Similarity	NPC51698
0.8283	Intermediate Similarity	NPC280254
0.8273	Intermediate Similarity	NPC94045
0.8257	Intermediate Similarity	NPC61885
0.8257	Intermediate Similarity	NPC63698
0.825	Intermediate Similarity	NPC127587
0.825	Intermediate Similarity	NPC293054
0.825	Intermediate Similarity	NPC236791
0.825	Intermediate Similarity	NPC210355
0.825	Intermediate Similarity	NPC470699
0.825	Intermediate Similarity	NPC156539
0.825	Intermediate Similarity	NPC282000
0.825	Intermediate Similarity	NPC324112
0.825	Intermediate Similarity	NPC159968
0.825	Intermediate Similarity	NPC246620
0.825	Intermediate Similarity	NPC74817
0.825	Intermediate Similarity	NPC124452
0.825	Intermediate Similarity	NPC82679
0.825	Intermediate Similarity	NPC107672
0.825	Intermediate Similarity	NPC266555
0.825	Intermediate Similarity	NPC169474
0.8241	Intermediate Similarity	NPC19149
0.8241	Intermediate Similarity	NPC1075
0.8241	Intermediate Similarity	NPC1786
0.8241	Intermediate Similarity	NPC477814
0.8241	Intermediate Similarity	NPC294902
0.822	Intermediate Similarity	NPC233526
0.822	Intermediate Similarity	NPC121115
0.822	Intermediate Similarity	NPC95168
0.822	Intermediate Similarity	NPC282496
0.8208	Intermediate Similarity	NPC166313
0.8208	Intermediate Similarity	NPC147310
0.8208	Intermediate Similarity	NPC294186
0.8208	Intermediate Similarity	NPC192032
0.8208	Intermediate Similarity	NPC137415
0.8208	Intermediate Similarity	NPC11280
0.8208	Intermediate Similarity	NPC24407
0.8198	Intermediate Similarity	NPC224527
0.819	Intermediate Similarity	NPC223451
0.8182	Intermediate Similarity	NPC470213
0.8182	Intermediate Similarity	NPC226331
0.8182	Intermediate Similarity	NPC154866
0.8182	Intermediate Similarity	NPC206615
0.8182	Intermediate Similarity	NPC186843
0.8182	Intermediate Similarity	NPC46274
0.8182	Intermediate Similarity	NPC98631

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 NPC176527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	422
0.1-0.2	1037
0.2-0.3	1880
0.3-0.4	2991
0.4-0.5	1597
0.5-0.6	891
0.6-0.7	277
0.7-0.8	48
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9394	High Similarity	NPD1242	Phase 1
0.8519	High Similarity	NPD3022	Approved
0.8519	High Similarity	NPD3021	Approved
0.8283	Intermediate Similarity	NPD9094	Approved
0.8208	Intermediate Similarity	NPD940	Approved
0.8208	Intermediate Similarity	NPD846	Approved
0.8182	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD3027	Phase 3
0.8099	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD2933	Approved
0.7981	Intermediate Similarity	NPD2934	Approved
0.7946	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD1613	Approved
0.792	Intermediate Similarity	NPD943	Approved
0.792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2859	Approved
0.7905	Intermediate Similarity	NPD2860	Approved
0.7876	Intermediate Similarity	NPD228	Approved
0.7857	Intermediate Similarity	NPD4750	Phase 3
0.785	Intermediate Similarity	NPD3020	Approved
0.7807	Intermediate Similarity	NPD9379	Approved
0.7807	Intermediate Similarity	NPD9377	Approved
0.78	Intermediate Similarity	NPD111	Approved
0.7686	Intermediate Similarity	NPD9269	Phase 2
0.7677	Intermediate Similarity	NPD9089	Approved
0.7623	Intermediate Similarity	NPD2982	Phase 2
0.7623	Intermediate Similarity	NPD2983	Phase 2
0.7583	Intermediate Similarity	NPD9384	Approved
0.7583	Intermediate Similarity	NPD9381	Approved
0.7576	Intermediate Similarity	NPD9093	Approved
0.7563	Intermediate Similarity	NPD1548	Phase 1
0.7541	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD2981	Phase 2
0.748	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD1610	Phase 2
0.7419	Intermediate Similarity	NPD5310	Approved
0.7419	Intermediate Similarity	NPD5311	Approved
0.7407	Intermediate Similarity	NPD844	Approved
0.7381	Intermediate Similarity	NPD3018	Phase 2
0.736	Intermediate Similarity	NPD3053	Approved
0.736	Intermediate Similarity	NPD3055	Approved
0.7355	Intermediate Similarity	NPD9268	Approved
0.7339	Intermediate Similarity	NPD9622	Approved
0.7339	Intermediate Similarity	NPD288	Approved
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7297	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3061	Approved
0.7231	Intermediate Similarity	NPD1558	Phase 1
0.7231	Intermediate Similarity	NPD3062	Approved
0.7231	Intermediate Similarity	NPD3059	Approved
0.7226	Intermediate Similarity	NPD1511	Approved
0.7165	Intermediate Similarity	NPD9620	Approved
0.7165	Intermediate Similarity	NPD9619	Approved
0.7165	Intermediate Similarity	NPD9621	Approved
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7122	Intermediate Similarity	NPD1512	Approved
0.7121	Intermediate Similarity	NPD5314	Approved
0.7077	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2342	Discontinued
0.7054	Intermediate Similarity	NPD4908	Phase 1
0.704	Intermediate Similarity	NPD422	Phase 1
0.704	Intermediate Similarity	NPD3092	Approved
0.7037	Intermediate Similarity	NPD7266	Discontinued
0.7008	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4625	Phase 3
0.6992	Remote Similarity	NPD2568	Approved
0.6991	Remote Similarity	NPD3028	Approved
0.6983	Remote Similarity	NPD968	Approved
0.6964	Remote Similarity	NPD9273	Approved
0.6957	Remote Similarity	NPD302	Approved
0.6957	Remote Similarity	NPD6190	Approved
0.6953	Remote Similarity	NPD3094	Phase 2
0.6949	Remote Similarity	NPD1792	Phase 2
0.6949	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD598	Approved
0.6947	Remote Similarity	NPD597	Approved
0.6947	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD601	Approved
0.6937	Remote Similarity	NPD1809	Phase 2
0.6935	Remote Similarity	NPD1357	Approved
0.6929	Remote Similarity	NPD4749	Approved
0.6917	Remote Similarity	NPD7635	Approved
0.6912	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5536	Phase 2
0.6909	Remote Similarity	NPD845	Approved
0.6899	Remote Similarity	NPD258	Approved
0.6899	Remote Similarity	NPD257	Approved
0.6894	Remote Similarity	NPD1132	Approved
0.6894	Remote Similarity	NPD1130	Approved
0.6894	Remote Similarity	NPD1136	Approved
0.688	Remote Similarity	NPD2286	Discontinued
0.687	Remote Similarity	NPD9500	Approved
0.6869	Remote Similarity	NPD9087	Approved
0.6866	Remote Similarity	NPD823	Approved
0.6866	Remote Similarity	NPD817	Approved
0.686	Remote Similarity	NPD2234	Approved
0.686	Remote Similarity	NPD2228	Approved
0.686	Remote Similarity	NPD2229	Approved
0.6857	Remote Similarity	NPD4357	Discontinued
0.6855	Remote Similarity	NPD3091	Approved
0.6847	Remote Similarity	NPD9296	Approved
0.6846	Remote Similarity	NPD9569	Approved
0.6846	Remote Similarity	NPD9494	Approved
0.6838	Remote Similarity	NPD1445	Approved
0.6838	Remote Similarity	NPD1444	Approved
0.6828	Remote Similarity	NPD1934	Approved
0.6822	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.681	Remote Similarity	NPD9608	Approved
0.681	Remote Similarity	NPD9610	Approved
0.6803	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4093	Discontinued
0.6788	Remote Similarity	NPD3540	Phase 1
0.6783	Remote Similarity	NPD1653	Approved
0.6781	Remote Similarity	NPD2801	Approved
0.6781	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.678	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1201	Approved
0.6765	Remote Similarity	NPD9088	Approved
0.6765	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2932	Approved
0.6746	Remote Similarity	NPD3019	Approved
0.6746	Remote Similarity	NPD4059	Approved
0.6718	Remote Similarity	NPD2861	Phase 2
0.6716	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1240	Approved
0.6716	Remote Similarity	NPD3620	Phase 2
0.6716	Remote Similarity	NPD1555	Discontinued
0.6715	Remote Similarity	NPD9570	Approved
0.6715	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3539	Phase 1
0.6692	Remote Similarity	NPD3145	Approved
0.6692	Remote Similarity	NPD3144	Approved
0.6689	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD259	Phase 1
0.6642	Remote Similarity	NPD1510	Phase 2
0.6642	Remote Similarity	NPD2674	Phase 3
0.6641	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD599	Approved
0.6641	Remote Similarity	NPD859	Approved
0.6641	Remote Similarity	NPD858	Approved
0.6641	Remote Similarity	NPD602	Approved
0.6639	Remote Similarity	NPD290	Approved
0.6618	Remote Similarity	NPD1607	Approved
0.6617	Remote Similarity	NPD9537	Phase 1
0.6617	Remote Similarity	NPD9536	Phase 1
0.6614	Remote Similarity	NPD1751	Approved
0.6613	Remote Similarity	NPD6671	Approved
0.6593	Remote Similarity	NPD825	Approved
0.6593	Remote Similarity	NPD826	Approved
0.6589	Remote Similarity	NPD2561	Approved
0.6589	Remote Similarity	NPD2562	Approved
0.6583	Remote Similarity	NPD2684	Approved
0.6577	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4675	Approved
0.6575	Remote Similarity	NPD4678	Approved
0.6571	Remote Similarity	NPD3060	Approved
0.6567	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD1470	Approved
0.6565	Remote Similarity	NPD1164	Approved
0.6544	Remote Similarity	NPD274	Approved
0.6544	Remote Similarity	NPD275	Approved
0.6544	Remote Similarity	NPD555	Phase 2
0.6538	Remote Similarity	NPD4659	Approved
0.6532	Remote Similarity	NPD9614	Approved
0.6532	Remote Similarity	NPD9618	Approved
0.6519	Remote Similarity	NPD6405	Approved
0.6519	Remote Similarity	NPD6407	Approved
0.6515	Remote Similarity	NPD6584	Phase 3
0.6512	Remote Similarity	NPD1091	Approved
0.6508	Remote Similarity	NPD317	Approved
0.6508	Remote Similarity	NPD318	Approved
0.6508	Remote Similarity	NPD856	Approved
0.6508	Remote Similarity	NPD16	Approved
0.6505	Remote Similarity	NPD9294	Approved
0.649	Remote Similarity	NPD6234	Discontinued
0.6484	Remote Similarity	NPD4589	Approved
0.6484	Remote Similarity	NPD3095	Discontinued
0.648	Remote Similarity	NPD709	Approved
0.6479	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD2219	Phase 1
0.6471	Remote Similarity	NPD4060	Phase 1
0.6462	Remote Similarity	NPD1608	Approved
0.6458	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1182	Approved
0.6457	Remote Similarity	NPD5304	Approved
0.6457	Remote Similarity	NPD5303	Approved
0.6457	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD9545	Approved
0.6446	Remote Similarity	NPD74	Approved
0.6446	Remote Similarity	NPD9266	Approved
0.6443	Remote Similarity	NPD1465	Phase 2
0.6439	Remote Similarity	NPD4103	Phase 2
0.6439	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7124	Phase 2
0.6434	Remote Similarity	NPD1980	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