NPASS Compound

Structure

NPC472993 OpenBabel07101719252D 44 48 0 0 1 0 0 0 0 0999 V2000 6.9282 -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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 40 1 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 2 0 0 0 0 3 15 1 0 0 0 0 4 6 1 0 0 0 0 4 16 2 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 26 1 0 0 0 0 10 15 2 0 0 0 0 10 23 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 24 2 0 0 0 0 13 21 1 0 0 0 0 13 22 2 0 0 0 0 14 41 1 0 0 0 0 16 22 1 0 0 0 0 17 32 1 0 0 0 0 18 42 1 0 0 0 0 19 23 2 0 0 0 0 19 33 1 0 0 0 0 20 27 2 0 0 0 0 20 34 1 0 0 0 0 21 27 1 0 0 0 0 21 35 2 0 0 0 0 22 43 1 0 0 0 0 23 40 1 0 0 0 0 24 27 1 0 0 0 0 24 43 1 0 0 0 0 25 14 1 6 0 0 0 25 28 1 0 0 0 0 25 44 1 0 0 0 0 26 36 2 0 0 0 0 26 41 1 0 0 0 0 28 29 1 0 0 0 0 28 37 1 1 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 31 1 0 0 0 0 30 39 1 1 0 0 0 31 42 1 6 0 0 0 31 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.15
Volume:	581.949
LogP:	3.511
LogD:	2.532
LogS:	-4.366
# Rotatable Bonds:	9
TPSA:	205.58
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	4.146
Fsp3:	0.226
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.189
MDCK Permeability:	2.2534679374075495e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.912
Human Intestinal Absorption (HIA):	0.507
20% Bioavailability (F20%):	0.211
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	99.9837417602539%
Volume Distribution (VD):	0.527
Pgp-substrate:	4.621647834777832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.573
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.33
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.759
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.654
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.394
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	4.73
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.817
AMES Toxicity:	0.703
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.951
Carcinogencity:	0.378
Eye Corrosion:	0.003
Eye Irritation:	0.286
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC472993

Natural Product ID:	NPC472993
*Common Name:**	RFBRMMMSAPRGDM-TUYFOBMESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RFBRMMMSAPRGDM-TUYFOBMESA-N
Standard InCHI:	InChI=1S/C31H28O13/c1-40-23-10-15(2-8-19(23)33)3-9-26(36)41-14-25-28(37)29(38)30(39)31(44-25)42-18-11-20(34)27-21(35)13-22(43-24(27)12-18)16-4-6-17(32)7-5-16/h2-13,25,28-34,37-39H,14H2,1H3/b9-3+/t25-,28-,29+,30-,31-/m1/s1
SMILES:	COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597471
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356064]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283497]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	leaf	Putz City, Chiayi County, Taiwan	2009-Nov	PMID[25999202]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28742368]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29397715]
NPO26700	Tinospora crispa	Species	Menispermaceae	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
IC50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	8800.0	nM	PMID[463197]
NPT35	Others	n.a.		Retention_time	=	41.8	min	PMID[463197]

☑ 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 NPC472993 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	407
0.1-0.2	1722
0.2-0.3	3912
0.3-0.4	8977
0.4-0.5	9177
0.5-0.6	4390
0.6-0.7	5170
0.7-0.8	5487
0.8-0.85	2047
0.85-0.9	808
0.9-0.95	517
0.95-1	83

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC217520
0.9817	High Similarity	NPC139571
0.9758	High Similarity	NPC471030
0.9756	High Similarity	NPC472991
0.9756	High Similarity	NPC472992
0.9755	High Similarity	NPC88560
0.9755	High Similarity	NPC172033
0.9755	High Similarity	NPC175230
0.9753	High Similarity	NPC149011
0.9753	High Similarity	NPC204937
0.9697	High Similarity	NPC477895
0.9697	High Similarity	NPC35167
0.9695	High Similarity	NPC34267
0.9695	High Similarity	NPC81042
0.9695	High Similarity	NPC223426
0.9695	High Similarity	NPC214621
0.9693	High Similarity	NPC47140
0.9693	High Similarity	NPC67134
0.9641	High Similarity	NPC36138
0.9641	High Similarity	NPC35924
0.9641	High Similarity	NPC199172
0.9636	High Similarity	NPC144097
0.9636	High Similarity	NPC61904
0.9632	High Similarity	NPC231194
0.9632	High Similarity	NPC51326
0.963	High Similarity	NPC116745
0.963	High Similarity	NPC229729
0.9627	High Similarity	NPC311830
0.9627	High Similarity	NPC22832
0.9583	High Similarity	NPC470720
0.9583	High Similarity	NPC470713
0.9583	High Similarity	NPC470717
0.9583	High Similarity	NPC460984
0.9583	High Similarity	NPC470416
0.9583	High Similarity	NPC25946
0.9583	High Similarity	NPC21359
0.9578	High Similarity	NPC217387
0.9578	High Similarity	NPC258044
0.9578	High Similarity	NPC476623
0.9578	High Similarity	NPC37668
0.9578	High Similarity	NPC196127
0.9578	High Similarity	NPC476621
0.9578	High Similarity	NPC476620
0.9578	High Similarity	NPC472387
0.9578	High Similarity	NPC267680
0.9578	High Similarity	NPC113836
0.9578	High Similarity	NPC476619
0.9578	High Similarity	NPC476622
0.9578	High Similarity	NPC293626
0.9578	High Similarity	NPC253521
0.9578	High Similarity	NPC476618
0.9573	High Similarity	NPC211594
0.9573	High Similarity	NPC254540
0.9573	High Similarity	NPC153755
0.9573	High Similarity	NPC172807
0.9571	High Similarity	NPC195257
0.9571	High Similarity	NPC209296
0.9568	High Similarity	NPC115674
0.9568	High Similarity	NPC210073
0.9565	High Similarity	NPC222936
0.9565	High Similarity	NPC270335
0.9565	High Similarity	NPC88023
0.9565	High Similarity	NPC243930
0.9565	High Similarity	NPC284960
0.9565	High Similarity	NPC168822
0.9565	High Similarity	NPC309025
0.9565	High Similarity	NPC191306
0.9565	High Similarity	NPC19709
0.9527	High Similarity	NPC474093
0.9527	High Similarity	NPC473554
0.9527	High Similarity	NPC470719
0.9527	High Similarity	NPC104910
0.9527	High Similarity	NPC295625
0.9524	High Similarity	NPC470718
0.9524	High Similarity	NPC241781
0.9524	High Similarity	NPC156785
0.9524	High Similarity	NPC162394
0.9515	High Similarity	NPC4390
0.9512	High Similarity	NPC244776
0.9512	High Similarity	NPC116864
0.9512	High Similarity	NPC206123
0.9503	High Similarity	NPC473043
0.9503	High Similarity	NPC189142
0.9503	High Similarity	NPC77660
0.9471	High Similarity	NPC475179
0.9467	High Similarity	NPC249560
0.9467	High Similarity	NPC223860
0.9467	High Similarity	NPC275977
0.9461	High Similarity	NPC173837
0.9461	High Similarity	NPC120952
0.9458	High Similarity	NPC477848
0.9455	High Similarity	NPC235575
0.9455	High Similarity	NPC205076
0.9455	High Similarity	NPC307518
0.9455	High Similarity	NPC190003
0.9455	High Similarity	NPC175107
0.9455	High Similarity	NPC48773
0.9455	High Similarity	NPC256760
0.9451	High Similarity	NPC186807
0.9451	High Similarity	NPC105025
0.9451	High Similarity	NPC219904
0.9451	High Similarity	NPC223747
0.9451	High Similarity	NPC45638
0.9451	High Similarity	NPC469931
0.9451	High Similarity	NPC86008
0.9451	High Similarity	NPC120099
0.9451	High Similarity	NPC225434
0.9451	High Similarity	NPC93337
0.9451	High Similarity	NPC201292
0.9451	High Similarity	NPC226294
0.9451	High Similarity	NPC58053
0.9451	High Similarity	NPC475942
0.9451	High Similarity	NPC229687
0.9451	High Similarity	NPC203050
0.9448	High Similarity	NPC8856
0.9448	High Similarity	NPC21100
0.9448	High Similarity	NPC197285
0.9448	High Similarity	NPC236934
0.9448	High Similarity	NPC5778
0.9444	High Similarity	NPC88043
0.9441	High Similarity	NPC305987
0.9441	High Similarity	NPC84324
0.9441	High Similarity	NPC472994
0.9441	High Similarity	NPC477629
0.9441	High Similarity	NPC182045
0.9441	High Similarity	NPC195685
0.9441	High Similarity	NPC270675
0.9441	High Similarity	NPC113163
0.9441	High Similarity	NPC477628
0.9441	High Similarity	NPC210961
0.9441	High Similarity	NPC66618
0.9441	High Similarity	NPC288131
0.9441	High Similarity	NPC165970
0.9412	High Similarity	NPC33083
0.9408	High Similarity	NPC135831
0.9408	High Similarity	NPC297503
0.9408	High Similarity	NPC97119
0.9401	High Similarity	NPC472385
0.9401	High Similarity	NPC198324
0.9401	High Similarity	NPC296018
0.9401	High Similarity	NPC471669
0.9401	High Similarity	NPC154741
0.9401	High Similarity	NPC233994
0.9401	High Similarity	NPC211532
0.9401	High Similarity	NPC89127
0.9398	High Similarity	NPC204693
0.9398	High Similarity	NPC208668
0.9394	High Similarity	NPC285197
0.9394	High Similarity	NPC44328
0.9394	High Similarity	NPC95866
0.9394	High Similarity	NPC105511
0.9394	High Similarity	NPC224462
0.9394	High Similarity	NPC155763
0.9394	High Similarity	NPC150767
0.9394	High Similarity	NPC105095
0.9394	High Similarity	NPC79056
0.9394	High Similarity	NPC177731
0.9394	High Similarity	NPC67105
0.9394	High Similarity	NPC78734
0.9394	High Similarity	NPC20505
0.9394	High Similarity	NPC235260
0.939	High Similarity	NPC84362
0.939	High Similarity	NPC45618
0.939	High Similarity	NPC58716
0.939	High Similarity	NPC173637
0.939	High Similarity	NPC226304
0.939	High Similarity	NPC265530
0.939	High Similarity	NPC52550
0.939	High Similarity	NPC45400
0.939	High Similarity	NPC317489
0.939	High Similarity	NPC127546
0.939	High Similarity	NPC325555
0.939	High Similarity	NPC146792
0.939	High Similarity	NPC223424
0.9387	High Similarity	NPC475366
0.9387	High Similarity	NPC139060
0.9387	High Similarity	NPC277205
0.9387	High Similarity	NPC475497
0.9387	High Similarity	NPC165720
0.9387	High Similarity	NPC284277
0.9383	High Similarity	NPC285108
0.9383	High Similarity	NPC33298
0.9383	High Similarity	NPC300537
0.9383	High Similarity	NPC127782
0.9379	High Similarity	NPC110349
0.9379	High Similarity	NPC101731
0.9357	High Similarity	NPC97817
0.9357	High Similarity	NPC30011
0.9357	High Similarity	NPC72554
0.9349	High Similarity	NPC469371
0.9345	High Similarity	NPC476773
0.9341	High Similarity	NPC237435
0.9341	High Similarity	NPC220173
0.9341	High Similarity	NPC101191
0.9341	High Similarity	NPC115760
0.9341	High Similarity	NPC198199
0.9341	High Similarity	NPC253685
0.9341	High Similarity	NPC473327
0.9341	High Similarity	NPC16194
0.9341	High Similarity	NPC19108

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 NPC472993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	937
0.2-0.3	1932
0.3-0.4	2615
0.4-0.5	1874
0.5-0.6	928
0.6-0.7	318
0.7-0.8	132
0.8-0.85	29
0.85-0.9	12
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9571	High Similarity	NPD7054	Approved
0.9512	High Similarity	NPD7472	Approved
0.9394	High Similarity	NPD7074	Phase 3
0.9341	High Similarity	NPD4338	Clinical (unspecified phase)
0.9337	High Similarity	NPD6797	Phase 2
0.9281	High Similarity	NPD7251	Discontinued
0.9273	High Similarity	NPD3818	Discontinued
0.9226	High Similarity	NPD7808	Phase 3
0.9152	High Similarity	NPD6167	Clinical (unspecified phase)
0.9152	High Similarity	NPD6168	Clinical (unspecified phase)
0.9152	High Similarity	NPD6166	Phase 2
0.9136	High Similarity	NPD4381	Clinical (unspecified phase)
0.8957	High Similarity	NPD4868	Clinical (unspecified phase)
0.8889	High Similarity	NPD1934	Approved
0.878	High Similarity	NPD3817	Phase 2
0.8765	High Similarity	NPD7804	Clinical (unspecified phase)
0.872	High Similarity	NPD2801	Approved
0.872	High Similarity	NPD2393	Clinical (unspecified phase)
0.8663	High Similarity	NPD7993	Clinical (unspecified phase)
0.8613	High Similarity	NPD6559	Discontinued
0.8537	High Similarity	NPD4380	Phase 2
0.8509	High Similarity	NPD1511	Approved
0.8503	High Similarity	NPD3882	Suspended
0.8452	Intermediate Similarity	NPD7075	Discontinued
0.8439	Intermediate Similarity	NPD5844	Phase 1
0.8415	Intermediate Similarity	NPD1653	Approved
0.8405	Intermediate Similarity	NPD1512	Approved
0.8373	Intermediate Similarity	NPD7411	Suspended
0.8354	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5402	Approved
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.8274	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6232	Discontinued
0.8242	Intermediate Similarity	NPD5403	Approved
0.8218	Intermediate Similarity	NPD7473	Discontinued
0.8202	Intermediate Similarity	NPD8313	Approved
0.8202	Intermediate Similarity	NPD8312	Approved
0.8198	Intermediate Similarity	NPD7199	Phase 2
0.8192	Intermediate Similarity	NPD7685	Pre-registration
0.8187	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8177	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD7228	Approved
0.8166	Intermediate Similarity	NPD1465	Phase 2
0.8166	Intermediate Similarity	NPD7819	Suspended
0.8161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD5494	Approved
0.8121	Intermediate Similarity	NPD5401	Approved
0.8121	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6959	Discontinued
0.8086	Intermediate Similarity	NPD1549	Phase 2
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6234	Discontinued
0.7966	Intermediate Similarity	NPD3751	Discontinued
0.7963	Intermediate Similarity	NPD2796	Approved
0.7952	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD8151	Discontinued
0.7914	Intermediate Similarity	NPD7266	Discontinued
0.7912	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1510	Phase 2
0.7895	Intermediate Similarity	NPD37	Approved
0.7882	Intermediate Similarity	NPD6599	Discontinued
0.7879	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD4967	Phase 2
0.7861	Intermediate Similarity	NPD7768	Phase 2
0.7861	Intermediate Similarity	NPD4965	Approved
0.7861	Intermediate Similarity	NPD4966	Approved
0.7849	Intermediate Similarity	NPD8455	Phase 2
0.7841	Intermediate Similarity	NPD3787	Discontinued
0.7826	Intermediate Similarity	NPD1933	Approved
0.7816	Intermediate Similarity	NPD3749	Approved
0.7771	Intermediate Similarity	NPD919	Approved
0.7771	Intermediate Similarity	NPD3750	Approved
0.776	Intermediate Similarity	NPD7435	Discontinued
0.7758	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6190	Approved
0.7716	Intermediate Similarity	NPD230	Phase 1
0.7711	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD6782	Approved
0.7696	Intermediate Similarity	NPD6779	Approved
0.7696	Intermediate Similarity	NPD6778	Approved
0.7696	Intermediate Similarity	NPD6776	Approved
0.7696	Intermediate Similarity	NPD6777	Approved
0.7696	Intermediate Similarity	NPD6780	Approved
0.7696	Intermediate Similarity	NPD6781	Approved
0.7692	Intermediate Similarity	NPD7240	Approved
0.7665	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7783	Phase 2
0.7665	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD1240	Approved
0.7654	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1613	Approved
0.7641	Intermediate Similarity	NPD7584	Approved
0.7636	Intermediate Similarity	NPD1551	Phase 2
0.7632	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD447	Suspended
0.7598	Intermediate Similarity	NPD3926	Phase 2
0.7561	Intermediate Similarity	NPD1607	Approved
0.7546	Intermediate Similarity	NPD943	Approved
0.7538	Intermediate Similarity	NPD7871	Phase 2
0.7538	Intermediate Similarity	NPD7870	Phase 2
0.7531	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2935	Discontinued
0.7525	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7874	Approved
0.7514	Intermediate Similarity	NPD7458	Discontinued
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7698	Approved
0.7486	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3748	Approved
0.7469	Intermediate Similarity	NPD3027	Phase 3
0.7436	Intermediate Similarity	NPD6823	Phase 2
0.7435	Intermediate Similarity	NPD6534	Approved
0.7435	Intermediate Similarity	NPD6535	Approved
0.7424	Intermediate Similarity	NPD7701	Phase 2
0.7424	Intermediate Similarity	NPD7585	Approved
0.7414	Intermediate Similarity	NPD3226	Approved
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD920	Approved
0.7398	Intermediate Similarity	NPD7680	Approved
0.7394	Intermediate Similarity	NPD8150	Discontinued
0.7384	Intermediate Similarity	NPD2534	Approved
0.7384	Intermediate Similarity	NPD2532	Approved
0.7384	Intermediate Similarity	NPD2533	Approved
0.7374	Intermediate Similarity	NPD7583	Approved
0.7371	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8320	Phase 1
0.736	Intermediate Similarity	NPD8319	Approved
0.7351	Intermediate Similarity	NPD5953	Discontinued
0.7346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7699	Phase 2
0.732	Intermediate Similarity	NPD7700	Phase 2
0.7314	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7801	Approved
0.7301	Intermediate Similarity	NPD6832	Phase 2
0.7294	Intermediate Similarity	NPD1243	Approved
0.7283	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7549	Discontinued
0.7267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7033	Discontinued
0.7246	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7286	Phase 2
0.7225	Intermediate Similarity	NPD7390	Discontinued
0.7222	Intermediate Similarity	NPD1203	Approved
0.7219	Intermediate Similarity	NPD7039	Approved
0.7219	Intermediate Similarity	NPD7038	Approved
0.7212	Intermediate Similarity	NPD2313	Discontinued
0.7212	Intermediate Similarity	NPD6798	Discontinued
0.7211	Intermediate Similarity	NPD8434	Phase 2
0.7207	Intermediate Similarity	NPD5353	Approved
0.7202	Intermediate Similarity	NPD6212	Phase 3
0.7202	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6213	Phase 3
0.7198	Intermediate Similarity	NPD8127	Discontinued
0.7195	Intermediate Similarity	NPD4908	Phase 1
0.7193	Intermediate Similarity	NPD1652	Phase 2
0.7193	Intermediate Similarity	NPD6674	Discontinued
0.7186	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2346	Discontinued
0.7174	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6233	Phase 2
0.716	Intermediate Similarity	NPD2799	Discontinued
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD9494	Approved
0.712	Intermediate Similarity	NPD5242	Approved
0.7108	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6844	Discontinued
0.7095	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2800	Approved
0.709	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5124	Phase 1
0.7081	Intermediate Similarity	NPD1091	Approved
0.7077	Intermediate Similarity	NPD4360	Phase 2
0.7077	Intermediate Similarity	NPD4363	Phase 3
0.7076	Intermediate Similarity	NPD2344	Approved
0.7073	Intermediate Similarity	NPD2798	Approved
0.7039	Intermediate Similarity	NPD6386	Approved
0.7039	Intermediate Similarity	NPD6385	Approved
0.7037	Intermediate Similarity	NPD9269	Phase 2
0.7037	Intermediate Similarity	NPD9717	Approved
0.7018	Intermediate Similarity	NPD6099	Approved
0.7018	Intermediate Similarity	NPD6100	Approved
0.7016	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD5005	Approved
0.7	Intermediate Similarity	NPD5006	Approved
0.7	Intermediate Similarity	NPD7097	Phase 1
0.6989	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD422	Phase 1

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