NPASS Compound

Structure

CID277588 OpenBabel06191716082D 23 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 6.0622 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 1.7321 1.0000 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 0.0000 1.0000 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 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 6 1 0 0 0 0 3 12 2 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.15
Volume:	336.773
LogP:	3.986
LogD:	3.55
LogS:	-3.308
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	2.643
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.008
MDCK Permeability:	1.5021835679362994e-05
Pgp-inhibitor:	0.134
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	98.04966735839844%
Volume Distribution (VD):	1.462
Pgp-substrate:	1.7922570705413818%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.322
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.945
CYP2D6-substrate:	0.744
CYP3A4-inhibitor:	0.538
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	18.295
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.545
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.966
Carcinogencity:	0.036
Eye Corrosion:	0.018
Eye Irritation:	0.927
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC277588

Natural Product ID:	NPC277588
*Common Name:**	Alpha,Alpha'-Dihydro-3,5,3',4'-Tetrahydroxy-5'-Isopentenylstilbene
IUPAC Name:	5-[2-(3,5-dihydroxyphenyl)ethyl]-3-(3-methylbut-2-enyl)benzene-1,2-diol
Synonyms:
Standard InCHIKey:	OLUUBKULUYLOQV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H22O4/c1-12(2)3-6-15-7-13(10-18(22)19(15)23)4-5-14-8-16(20)11-17(21)9-14/h3,7-11,20-23H,4-6H2,1-2H3
SMILES:	CC(=CCc1cc(CCc2cc(cc(c2)O)O)cc(c1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465166
PubChem CID:	10335780
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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	9.0	10'4/M/s	PMID[514702]

☑ 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 NPC277588 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	340
0.1-0.2	1827
0.2-0.3	5679
0.3-0.4	13762
0.4-0.5	4785
0.5-0.6	5269
0.6-0.7	7910
0.7-0.8	2600
0.8-0.85	401
0.85-0.9	100
0.9-0.95	20
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.982	High Similarity	NPC191866
0.9646	High Similarity	NPC24125
0.9561	High Similarity	NPC237667
0.9554	High Similarity	NPC144343
0.9397	High Similarity	NPC53567
0.9364	High Similarity	NPC43525
0.9316	High Similarity	NPC224342
0.9298	High Similarity	NPC217174
0.9273	High Similarity	NPC165770
0.9273	High Similarity	NPC268032
0.9273	High Similarity	NPC225679
0.9273	High Similarity	NPC4493
0.9273	High Similarity	NPC476632
0.9224	High Similarity	NPC39029
0.9115	High Similarity	NPC472893
0.9107	High Similarity	NPC117846
0.9083	High Similarity	NPC252131
0.9052	High Similarity	NPC223451
0.9027	High Similarity	NPC107240
0.9008	High Similarity	NPC28765
0.9	High Similarity	NPC114392
0.9	High Similarity	NPC61885
0.9	High Similarity	NPC58427
0.9	High Similarity	NPC34864
0.9	High Similarity	NPC63698
0.9	High Similarity	NPC105727
0.8909	High Similarity	NPC176527
0.8889	High Similarity	NPC472071
0.8889	High Similarity	NPC475245
0.885	High Similarity	NPC166995
0.879	High Similarity	NPC15543
0.877	High Similarity	NPC74817
0.877	High Similarity	NPC246620
0.877	High Similarity	NPC124452
0.877	High Similarity	NPC324112
0.877	High Similarity	NPC293054
0.877	High Similarity	NPC169474
0.877	High Similarity	NPC82679
0.877	High Similarity	NPC236791
0.877	High Similarity	NPC282000
0.877	High Similarity	NPC159968
0.875	High Similarity	NPC33728
0.875	High Similarity	NPC254833
0.875	High Similarity	NPC136319
0.875	High Similarity	NPC228343
0.875	High Similarity	NPC19808
0.8727	High Similarity	NPC292452
0.8727	High Similarity	NPC246056
0.8727	High Similarity	NPC474839
0.8689	High Similarity	NPC28730
0.8689	High Similarity	NPC214406
0.8689	High Similarity	NPC44748
0.8689	High Similarity	NPC78974
0.8689	High Similarity	NPC223136
0.8689	High Similarity	NPC18924
0.8689	High Similarity	NPC103823
0.8661	High Similarity	NPC174981
0.8651	High Similarity	NPC474453
0.8649	High Similarity	NPC470700
0.8649	High Similarity	NPC39664
0.8649	High Similarity	NPC39097
0.8649	High Similarity	NPC109691
0.8649	High Similarity	NPC118286
0.8649	High Similarity	NPC302681
0.8636	High Similarity	NPC471511
0.8636	High Similarity	NPC102216
0.8636	High Similarity	NPC119860
0.8636	High Similarity	NPC241891
0.8636	High Similarity	NPC30506
0.8629	High Similarity	NPC212015
0.8609	High Similarity	NPC23804
0.8609	High Similarity	NPC263753
0.8607	High Similarity	NPC82483
0.8607	High Similarity	NPC105925
0.8607	High Similarity	NPC472093
0.8607	High Similarity	NPC234400
0.8607	High Similarity	NPC203133
0.8607	High Similarity	NPC17943
0.8607	High Similarity	NPC265483
0.8607	High Similarity	NPC251855
0.8607	High Similarity	NPC60885
0.8607	High Similarity	NPC33654
0.8607	High Similarity	NPC233410
0.8607	High Similarity	NPC116907
0.8607	High Similarity	NPC298757
0.8607	High Similarity	NPC221077
0.8607	High Similarity	NPC57490
0.8607	High Similarity	NPC299584
0.8607	High Similarity	NPC117214
0.8607	High Similarity	NPC193544
0.8607	High Similarity	NPC475169
0.8607	High Similarity	NPC208950
0.8596	High Similarity	NPC179002
0.8596	High Similarity	NPC257430
0.8596	High Similarity	NPC187583
0.8596	High Similarity	NPC224527
0.8595	High Similarity	NPC197757
0.8595	High Similarity	NPC121115
0.8595	High Similarity	NPC228922
0.8583	High Similarity	NPC476633
0.8571	High Similarity	NPC54844
0.856	High Similarity	NPC51840
0.856	High Similarity	NPC299221
0.856	High Similarity	NPC234488
0.856	High Similarity	NPC311680
0.856	High Similarity	NPC126836
0.8559	High Similarity	NPC37802
0.8559	High Similarity	NPC134829
0.8548	High Similarity	NPC154866
0.8547	High Similarity	NPC115808
0.8537	High Similarity	NPC76451
0.8534	High Similarity	NPC120280
0.8522	High Similarity	NPC471179
0.8516	High Similarity	NPC473413
0.8516	High Similarity	NPC256262
0.8512	High Similarity	NPC41562
0.8509	High Similarity	NPC147634
0.8509	High Similarity	NPC79793
0.8509	High Similarity	NPC174096
0.8509	High Similarity	NPC226401
0.8509	High Similarity	NPC120982
0.8509	High Similarity	NPC224870
0.8509	High Similarity	NPC475018
0.8492	Intermediate Similarity	NPC232275
0.8487	Intermediate Similarity	NPC176893
0.8482	Intermediate Similarity	NPC99836
0.8482	Intermediate Similarity	NPC12640
0.8482	Intermediate Similarity	NPC201662
0.8482	Intermediate Similarity	NPC248904
0.848	Intermediate Similarity	NPC58164
0.848	Intermediate Similarity	NPC10225
0.8475	Intermediate Similarity	NPC470760
0.8468	Intermediate Similarity	NPC244513
0.8468	Intermediate Similarity	NPC218879
0.8468	Intermediate Similarity	NPC127587
0.8468	Intermediate Similarity	NPC236760
0.8468	Intermediate Similarity	NPC266555
0.8468	Intermediate Similarity	NPC227458
0.8462	Intermediate Similarity	NPC84999
0.8462	Intermediate Similarity	NPC246760
0.8455	Intermediate Similarity	NPC11280
0.8455	Intermediate Similarity	NPC147310
0.8455	Intermediate Similarity	NPC192032
0.8455	Intermediate Similarity	NPC137415
0.8455	Intermediate Similarity	NPC100340
0.8455	Intermediate Similarity	NPC143659
0.8455	Intermediate Similarity	NPC166313
0.8455	Intermediate Similarity	NPC294186
0.8455	Intermediate Similarity	NPC24407
0.845	Intermediate Similarity	NPC264112
0.845	Intermediate Similarity	NPC65005
0.845	Intermediate Similarity	NPC470802
0.845	Intermediate Similarity	NPC194764
0.8448	Intermediate Similarity	NPC261343
0.8443	Intermediate Similarity	NPC84086
0.8443	Intermediate Similarity	NPC95168
0.8443	Intermediate Similarity	NPC282496
0.8443	Intermediate Similarity	NPC233526
0.8438	Intermediate Similarity	NPC209199
0.8438	Intermediate Similarity	NPC125649
0.8425	Intermediate Similarity	NPC127624
0.8425	Intermediate Similarity	NPC6451
0.8421	Intermediate Similarity	NPC55617
0.8421	Intermediate Similarity	NPC202647
0.8421	Intermediate Similarity	NPC299568
0.8421	Intermediate Similarity	NPC186385
0.8421	Intermediate Similarity	NPC62258
0.8413	Intermediate Similarity	NPC244441
0.8407	Intermediate Similarity	NPC158253
0.8407	Intermediate Similarity	NPC204901
0.8407	Intermediate Similarity	NPC232523
0.84	Intermediate Similarity	NPC206615
0.84	Intermediate Similarity	NPC186843
0.84	Intermediate Similarity	NPC266691
0.84	Intermediate Similarity	NPC470213
0.84	Intermediate Similarity	NPC98631
0.8393	Intermediate Similarity	NPC239291
0.8387	Intermediate Similarity	NPC223953
0.8387	Intermediate Similarity	NPC181361
0.8385	Intermediate Similarity	NPC242715
0.8385	Intermediate Similarity	NPC22902
0.8385	Intermediate Similarity	NPC56329
0.8378	Intermediate Similarity	NPC146798
0.8378	Intermediate Similarity	NPC302219
0.8378	Intermediate Similarity	NPC24404
0.8378	Intermediate Similarity	NPC222522
0.8378	Intermediate Similarity	NPC106396
0.8378	Intermediate Similarity	NPC168303
0.8378	Intermediate Similarity	NPC71002
0.8378	Intermediate Similarity	NPC94351
0.8378	Intermediate Similarity	NPC85479
0.8378	Intermediate Similarity	NPC196479
0.8378	Intermediate Similarity	NPC242342
0.8378	Intermediate Similarity	NPC53051
0.8378	Intermediate Similarity	NPC249828
0.8378	Intermediate Similarity	NPC313030
0.8376	Intermediate Similarity	NPC473137
0.8376	Intermediate Similarity	NPC12656
0.8372	Intermediate Similarity	NPC108198
0.8372	Intermediate Similarity	NPC10314

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 NPC277588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	1014
0.2-0.3	1682
0.3-0.4	3052
0.4-0.5	1635
0.5-0.6	969
0.6-0.7	391
0.7-0.8	59
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD3021	Approved
0.875	High Similarity	NPD3022	Approved
0.8455	Intermediate Similarity	NPD940	Approved
0.8455	Intermediate Similarity	NPD846	Approved
0.8421	Intermediate Similarity	NPD4750	Phase 3
0.8364	Intermediate Similarity	NPD1242	Phase 1
0.8333	Intermediate Similarity	NPD3027	Phase 3
0.832	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2860	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD2859	Approved
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7946	Intermediate Similarity	NPD3020	Approved
0.7909	Intermediate Similarity	NPD2933	Approved
0.7909	Intermediate Similarity	NPD2934	Approved
0.771	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1809	Phase 2
0.7679	Intermediate Similarity	NPD844	Approved
0.7634	Intermediate Similarity	NPD4625	Phase 3
0.7615	Intermediate Similarity	NPD3018	Phase 2
0.7603	Intermediate Similarity	NPD7635	Approved
0.7557	Intermediate Similarity	NPD4908	Phase 1
0.7521	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD845	Approved
0.7479	Intermediate Similarity	NPD2342	Discontinued
0.7466	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD288	Approved
0.7442	Intermediate Similarity	NPD2983	Phase 2
0.7442	Intermediate Similarity	NPD2982	Phase 2
0.7442	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4749	Approved
0.7438	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD1610	Phase 2
0.7414	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5283	Phase 1
0.7381	Intermediate Similarity	NPD1548	Phase 1
0.7372	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD2981	Phase 2
0.7364	Intermediate Similarity	NPD9094	Approved
0.7364	Intermediate Similarity	NPD9269	Phase 2
0.7328	Intermediate Similarity	NPD3094	Phase 2
0.7328	Intermediate Similarity	NPD3055	Approved
0.7328	Intermediate Similarity	NPD3053	Approved
0.7317	Intermediate Similarity	NPD9379	Approved
0.7317	Intermediate Similarity	NPD9377	Approved
0.7308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3092	Approved
0.7273	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD5310	Approved
0.7252	Intermediate Similarity	NPD5311	Approved
0.7246	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3061	Approved
0.7206	Intermediate Similarity	NPD3059	Approved
0.7206	Intermediate Similarity	NPD3062	Approved
0.7206	Intermediate Similarity	NPD4060	Phase 1
0.7203	Intermediate Similarity	NPD7390	Discontinued
0.7203	Intermediate Similarity	NPD1511	Approved
0.7185	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1934	Approved
0.7153	Intermediate Similarity	NPD230	Phase 1
0.7153	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7132	Intermediate Similarity	NPD6405	Approved
0.7132	Intermediate Similarity	NPD6407	Approved
0.7132	Intermediate Similarity	NPD4589	Approved
0.7132	Intermediate Similarity	NPD9384	Approved
0.7132	Intermediate Similarity	NPD9381	Approved
0.712	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3028	Approved
0.7114	Intermediate Similarity	NPD2801	Approved
0.7109	Intermediate Similarity	NPD5303	Approved
0.7109	Intermediate Similarity	NPD3091	Approved
0.7109	Intermediate Similarity	NPD5304	Approved
0.7103	Intermediate Similarity	NPD1512	Approved
0.7101	Intermediate Similarity	NPD5314	Approved
0.7101	Intermediate Similarity	NPD2568	Approved
0.7091	Intermediate Similarity	NPD111	Approved
0.708	Intermediate Similarity	NPD3620	Phase 2
0.708	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1555	Discontinued
0.7068	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9268	Approved
0.7054	Intermediate Similarity	NPD4093	Discontinued
0.7045	Intermediate Similarity	NPD9622	Approved
0.7039	Intermediate Similarity	NPD6234	Discontinued
0.7023	Intermediate Similarity	NPD422	Phase 1
0.7021	Intermediate Similarity	NPD3540	Phase 1
0.702	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3882	Suspended
0.7008	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD4059	Approved
0.7	Intermediate Similarity	NPD2286	Discontinued
0.7	Intermediate Similarity	NPD2932	Approved
0.7	Intermediate Similarity	NPD3019	Approved
0.6984	Remote Similarity	NPD2229	Approved
0.6984	Remote Similarity	NPD2234	Approved
0.6984	Remote Similarity	NPD2228	Approved
0.697	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2421	Approved
0.6966	Remote Similarity	NPD2420	Approved
0.6963	Remote Similarity	NPD2861	Phase 2
0.6957	Remote Similarity	NPD1558	Phase 1
0.6953	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5404	Approved
0.695	Remote Similarity	NPD3539	Phase 1
0.695	Remote Similarity	NPD5406	Approved
0.695	Remote Similarity	NPD5408	Approved
0.695	Remote Similarity	NPD5405	Approved
0.695	Remote Similarity	NPD2935	Discontinued
0.6935	Remote Similarity	NPD1792	Phase 2
0.6934	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD37	Approved
0.6929	Remote Similarity	NPD497	Approved
0.6923	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6232	Discontinued
0.6894	Remote Similarity	NPD1201	Approved
0.6889	Remote Similarity	NPD258	Approved
0.6889	Remote Similarity	NPD9619	Approved
0.6889	Remote Similarity	NPD257	Approved
0.6889	Remote Similarity	NPD9621	Approved
0.6889	Remote Similarity	NPD9620	Approved
0.6881	Remote Similarity	NPD9093	Approved
0.687	Remote Similarity	NPD3095	Discontinued
0.687	Remote Similarity	NPD4626	Approved
0.687	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.686	Remote Similarity	NPD9500	Approved
0.685	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.685	Remote Similarity	NPD498	Approved
0.685	Remote Similarity	NPD495	Approved
0.685	Remote Similarity	NPD496	Approved
0.6846	Remote Similarity	NPD7330	Discontinued
0.6835	Remote Similarity	NPD1240	Approved
0.6831	Remote Similarity	NPD6100	Approved
0.6831	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6099	Approved
0.6829	Remote Similarity	NPD1445	Approved
0.6829	Remote Similarity	NPD1444	Approved
0.6828	Remote Similarity	NPD302	Approved
0.6828	Remote Similarity	NPD6190	Approved
0.6818	Remote Similarity	NPD9089	Approved
0.6815	Remote Similarity	NPD1133	Approved
0.6815	Remote Similarity	NPD1129	Approved
0.6815	Remote Similarity	NPD1164	Approved
0.6815	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1470	Approved
0.6815	Remote Similarity	NPD6166	Phase 2
0.6815	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1134	Approved
0.6815	Remote Similarity	NPD1131	Approved
0.6815	Remote Similarity	NPD1135	Approved
0.6812	Remote Similarity	NPD597	Approved
0.6812	Remote Similarity	NPD598	Approved
0.6812	Remote Similarity	NPD601	Approved
0.6809	Remote Similarity	NPD3552	Approved
0.6809	Remote Similarity	NPD3554	Approved
0.6809	Remote Similarity	NPD3555	Approved
0.6809	Remote Similarity	NPD3553	Approved
0.6803	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4380	Phase 2
0.6797	Remote Similarity	NPD4967	Phase 2
0.6797	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4965	Approved
0.6797	Remote Similarity	NPD4966	Approved
0.6779	Remote Similarity	NPD1653	Approved
0.6772	Remote Similarity	NPD7473	Discontinued
0.6769	Remote Similarity	NPD5536	Phase 2
0.6763	Remote Similarity	NPD1132	Approved
0.6763	Remote Similarity	NPD1136	Approved
0.6763	Remote Similarity	NPD1130	Approved
0.6761	Remote Similarity	NPD1510	Phase 2
0.6759	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD8166	Discontinued
0.6742	Remote Similarity	NPD1751	Approved
0.6741	Remote Similarity	NPD6696	Suspended
0.6741	Remote Similarity	NPD8651	Approved
0.6738	Remote Similarity	NPD817	Approved
0.6738	Remote Similarity	NPD823	Approved
0.6738	Remote Similarity	NPD4097	Suspended
0.6738	Remote Similarity	NPD1607	Approved
0.6735	Remote Similarity	NPD4357	Discontinued
0.6733	Remote Similarity	NPD4005	Discontinued
0.673	Remote Similarity	NPD7228	Approved
0.672	Remote Similarity	NPD2684	Approved
0.6718	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD826	Approved
0.6714	Remote Similarity	NPD825	Approved
0.6712	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4538	Approved
0.669	Remote Similarity	NPD4536	Approved
0.669	Remote Similarity	NPD6674	Discontinued
0.669	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3060	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