NPASS Compound

Structure

NPC472992 OpenBabel07101719252D 43 47 0 0 1 0 0 0 0 0999 V2000 6.0622 1.5000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 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 -1.7321 5.0000 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 -0.8660 -1.5000 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 5.0000 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 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 -2.5981 4.5000 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 0.0000 -1.0000 0.0000 C 0 0 2 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 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 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 1 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 8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 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 3.4641 -1.0000 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 0.8660 3.5000 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 3.5000 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 1 14 2 0 0 0 0 2 7 2 0 0 0 0 2 14 1 0 0 0 0 3 10 2 0 0 0 0 3 14 1 0 0 0 0 4 8 1 0 0 0 0 4 15 2 0 0 0 0 5 9 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 11 20 2 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 13 31 1 0 0 0 0 15 20 1 0 0 0 0 16 32 1 0 0 0 0 17 33 1 0 0 0 0 18 24 1 0 0 0 0 18 34 2 0 0 0 0 19 28 1 0 0 0 0 19 35 1 0 0 0 0 20 40 1 0 0 0 0 21 24 2 0 0 0 0 21 40 1 0 0 0 0 22 13 1 1 0 0 0 22 25 1 0 0 0 0 22 41 1 0 0 0 0 23 36 2 0 0 0 0 23 42 1 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 25 37 1 6 0 0 0 26 28 2 0 0 0 0 26 38 1 0 0 0 0 27 29 1 0 0 0 0 27 39 1 1 0 0 0 28 43 1 0 0 0 0 29 30 1 0 0 0 0 29 42 1 6 0 0 0 30 41 1 0 0 0 0 30 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.14
Volume:	564.653
LogP:	3.077
LogD:	1.754
LogS:	-4.141
# Rotatable Bonds:	8
TPSA:	216.58
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.12
Synthetic Accessibility Score:	4.239
Fsp3:	0.2
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:	-6.136
MDCK Permeability:	1.2263877579243854e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.595
Human Intestinal Absorption (HIA):	0.381
20% Bioavailability (F20%):	0.487
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	100.57835388183594%
Volume Distribution (VD):	0.498
Pgp-substrate:	3.7330753803253174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.444
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.581
CYP2C9-substrate:	0.697
CYP2D6-inhibitor:	0.587
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.277
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	4.478
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.208
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.537
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.951
Carcinogencity:	0.137
Eye Corrosion:	0.003
Eye Irritation:	0.237
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC472992

Natural Product ID:	NPC472992
*Common Name:**	ACHIQCZROFTJIU-DBIPPQOESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ACHIQCZROFTJIU-DBIPPQOESA-N
Standard InCHI:	InChI=1S/C30H26O13/c31-13-22-25(37)27(39)29(42-23(36)10-3-14-1-6-16(32)7-2-14)30(41-22)43-28-19(35)12-21-24(26(28)38)18(34)11-20(40-21)15-4-8-17(33)9-5-15/h1-12,22,25,27,29-33,35,37-39H,13H2/b10-3+/t22-,25-,27+,29-,30+/m1/s1
SMILES:	C1=CC(=CC=C1C=CC(=O)OC2C(C(C(OC2OC3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597470
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

*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	=	4300.0	nM	PMID[540567]
NPT35	Others	n.a.		Retention_time	=	36.5	min	PMID[540567]

☑ 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 NPC472992 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	442
0.1-0.2	1830
0.2-0.3	4287
0.3-0.4	9512
0.4-0.5	8561
0.5-0.6	4348
0.6-0.7	5260
0.7-0.8	5262
0.8-0.85	1763
0.85-0.9	862
0.9-0.95	487
0.95-1	83

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472991
0.9818	High Similarity	NPC476618
0.9818	High Similarity	NPC476622
0.9818	High Similarity	NPC476619
0.9818	High Similarity	NPC476623
0.9818	High Similarity	NPC476621
0.9818	High Similarity	NPC476620
0.976	High Similarity	NPC36138
0.9756	High Similarity	NPC472993
0.9755	High Similarity	NPC149011
0.9755	High Similarity	NPC204937
0.9702	High Similarity	NPC470416
0.9699	High Similarity	NPC472387
0.9695	High Similarity	NPC211594
0.9695	High Similarity	NPC172807
0.9695	High Similarity	NPC254540
0.9639	High Similarity	NPC144097
0.9639	High Similarity	NPC61904
0.9636	High Similarity	NPC172033
0.9636	High Similarity	NPC88560
0.9636	High Similarity	NPC175230
0.9632	High Similarity	NPC58716
0.9632	High Similarity	NPC45618
0.9632	High Similarity	NPC146792
0.9581	High Similarity	NPC113836
0.9581	High Similarity	NPC139571
0.9581	High Similarity	NPC37668
0.9581	High Similarity	NPC253521
0.9581	High Similarity	NPC217520
0.9581	High Similarity	NPC35167
0.9578	High Similarity	NPC237435
0.9578	High Similarity	NPC43211
0.9578	High Similarity	NPC115760
0.9578	High Similarity	NPC223426
0.9578	High Similarity	NPC81042
0.9578	High Similarity	NPC49344
0.9578	High Similarity	NPC135277
0.9578	High Similarity	NPC210094
0.9578	High Similarity	NPC214621
0.9578	High Similarity	NPC101191
0.9578	High Similarity	NPC34267
0.9578	High Similarity	NPC477848
0.9576	High Similarity	NPC205076
0.9576	High Similarity	NPC307518
0.9576	High Similarity	NPC48773
0.9576	High Similarity	NPC67134
0.9576	High Similarity	NPC259152
0.9576	High Similarity	NPC47140
0.9576	High Similarity	NPC3583
0.9573	High Similarity	NPC186807
0.9573	High Similarity	NPC93337
0.9573	High Similarity	NPC226294
0.9573	High Similarity	NPC469931
0.9573	High Similarity	NPC45638
0.9573	High Similarity	NPC105025
0.9573	High Similarity	NPC58053
0.9573	High Similarity	NPC201292
0.9573	High Similarity	NPC475942
0.9524	High Similarity	NPC471030
0.9521	High Similarity	NPC233994
0.9521	High Similarity	NPC211532
0.9521	High Similarity	NPC472385
0.9521	High Similarity	NPC198324
0.9518	High Similarity	NPC204693
0.9515	High Similarity	NPC282987
0.9515	High Similarity	NPC105511
0.9515	High Similarity	NPC224462
0.9515	High Similarity	NPC34287
0.9515	High Similarity	NPC471416
0.9515	High Similarity	NPC245014
0.9515	High Similarity	NPC84265
0.9512	High Similarity	NPC116745
0.9464	High Similarity	NPC293626
0.9464	High Similarity	NPC267680
0.9464	High Similarity	NPC217387
0.9464	High Similarity	NPC196127
0.9464	High Similarity	NPC258044
0.9464	High Similarity	NPC477895
0.9461	High Similarity	NPC264735
0.9458	High Similarity	NPC476405
0.9458	High Similarity	NPC472386
0.9458	High Similarity	NPC117260
0.9455	High Similarity	NPC471457
0.9455	High Similarity	NPC170675
0.9455	High Similarity	NPC112755
0.9448	High Similarity	NPC191306
0.9448	High Similarity	NPC270335
0.9448	High Similarity	NPC168822
0.9448	High Similarity	NPC88043
0.9412	High Similarity	NPC297503
0.9412	High Similarity	NPC470446
0.9412	High Similarity	NPC199172
0.9412	High Similarity	NPC470445
0.9412	High Similarity	NPC35924
0.9412	High Similarity	NPC97119
0.9412	High Similarity	NPC135831
0.9412	High Similarity	NPC470718
0.9412	High Similarity	NPC470449
0.9412	High Similarity	NPC470447
0.9405	High Similarity	NPC8573
0.9405	High Similarity	NPC169733
0.9405	High Similarity	NPC296018
0.9405	High Similarity	NPC154741
0.9405	High Similarity	NPC268533
0.9401	High Similarity	NPC239549
0.9401	High Similarity	NPC236191
0.9401	High Similarity	NPC24043
0.9401	High Similarity	NPC4390
0.9401	High Similarity	NPC169977
0.9401	High Similarity	NPC101026
0.9401	High Similarity	NPC42773
0.9401	High Similarity	NPC51774
0.9401	High Similarity	NPC45522
0.9401	High Similarity	NPC21666
0.9398	High Similarity	NPC155763
0.9398	High Similarity	NPC235260
0.9398	High Similarity	NPC21190
0.9398	High Similarity	NPC44558
0.9398	High Similarity	NPC474434
0.9398	High Similarity	NPC20505
0.9398	High Similarity	NPC22195
0.9398	High Similarity	NPC51326
0.9398	High Similarity	NPC183357
0.9398	High Similarity	NPC231194
0.9394	High Similarity	NPC229729
0.9394	High Similarity	NPC135345
0.9394	High Similarity	NPC45400
0.9394	High Similarity	NPC243877
0.939	High Similarity	NPC22832
0.939	High Similarity	NPC165720
0.939	High Similarity	NPC311830
0.9387	High Similarity	NPC90905
0.9387	High Similarity	NPC77660
0.9387	High Similarity	NPC189142
0.9387	High Similarity	NPC4013
0.9357	High Similarity	NPC470451
0.9357	High Similarity	NPC470717
0.9357	High Similarity	NPC25946
0.9357	High Similarity	NPC470720
0.9357	High Similarity	NPC470455
0.9357	High Similarity	NPC21359
0.9357	High Similarity	NPC460984
0.9357	High Similarity	NPC470713
0.9353	High Similarity	NPC222674
0.9349	High Similarity	NPC476773
0.9345	High Similarity	NPC472607
0.9345	High Similarity	NPC253685
0.9341	High Similarity	NPC271848
0.9341	High Similarity	NPC267254
0.9341	High Similarity	NPC475155
0.9341	High Similarity	NPC175107
0.9341	High Similarity	NPC81332
0.9341	High Similarity	NPC262580
0.9341	High Similarity	NPC289396
0.9341	High Similarity	NPC212038
0.9341	High Similarity	NPC301683
0.9341	High Similarity	NPC190003
0.9341	High Similarity	NPC153755
0.9337	High Similarity	NPC210042
0.9337	High Similarity	NPC138927
0.9337	High Similarity	NPC183036
0.9337	High Similarity	NPC472383
0.9337	High Similarity	NPC472381
0.9337	High Similarity	NPC209296
0.9337	High Similarity	NPC195257
0.9337	High Similarity	NPC229687
0.9337	High Similarity	NPC95855
0.9337	High Similarity	NPC86008
0.9333	High Similarity	NPC21100
0.9333	High Similarity	NPC8856
0.9333	High Similarity	NPC197285
0.9333	High Similarity	NPC115674
0.9333	High Similarity	NPC99957
0.9333	High Similarity	NPC181616
0.9333	High Similarity	NPC210073
0.9329	High Similarity	NPC284960
0.9329	High Similarity	NPC94777
0.9329	High Similarity	NPC88023
0.9329	High Similarity	NPC19709
0.9329	High Similarity	NPC309025
0.9329	High Similarity	NPC222936
0.9329	High Similarity	NPC243930
0.9325	High Similarity	NPC195685
0.9325	High Similarity	NPC210961
0.9325	High Similarity	NPC477629
0.9325	High Similarity	NPC477628
0.9325	High Similarity	NPC472994
0.9325	High Similarity	NPC270675
0.9302	High Similarity	NPC295625
0.9302	High Similarity	NPC104910
0.9302	High Similarity	NPC473554
0.9302	High Similarity	NPC474093
0.9302	High Similarity	NPC261623
0.9302	High Similarity	NPC111490
0.9302	High Similarity	NPC470719
0.9298	High Similarity	NPC162394
0.9298	High Similarity	NPC241781
0.9298	High Similarity	NPC107987
0.9298	High Similarity	NPC156785
0.9294	High Similarity	NPC110941

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 NPC472992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	960
0.2-0.3	2024
0.3-0.4	2659
0.4-0.5	1794
0.5-0.6	880
0.6-0.7	274
0.7-0.8	121
0.8-0.85	25
0.85-0.9	12
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9578	High Similarity	NPD4338	Clinical (unspecified phase)
0.9337	High Similarity	NPD7054	Approved
0.9281	High Similarity	NPD7472	Approved
0.9277	High Similarity	NPD3818	Discontinued
0.9167	High Similarity	NPD7074	Phase 3
0.9112	High Similarity	NPD6797	Phase 2
0.9059	High Similarity	NPD7251	Discontinued
0.9024	High Similarity	NPD4381	Clinical (unspecified phase)
0.9006	High Similarity	NPD7808	Phase 3
0.8963	High Similarity	NPD4868	Clinical (unspecified phase)
0.8929	High Similarity	NPD6168	Clinical (unspecified phase)
0.8929	High Similarity	NPD6167	Clinical (unspecified phase)
0.8929	High Similarity	NPD6166	Phase 2
0.8841	High Similarity	NPD2801	Approved
0.8671	High Similarity	NPD7993	Clinical (unspecified phase)
0.8667	High Similarity	NPD1934	Approved
0.8563	High Similarity	NPD5402	Approved
0.8563	High Similarity	NPD3817	Phase 2
0.8555	High Similarity	NPD7804	Clinical (unspecified phase)
0.8537	High Similarity	NPD1653	Approved
0.8503	High Similarity	NPD2393	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD5844	Phase 1
0.8434	Intermediate Similarity	NPD4380	Phase 2
0.8409	Intermediate Similarity	NPD6559	Discontinued
0.8405	Intermediate Similarity	NPD1511	Approved
0.8402	Intermediate Similarity	NPD3882	Suspended
0.8303	Intermediate Similarity	NPD1512	Approved
0.8297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8287	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD5494	Approved
0.8246	Intermediate Similarity	NPD7075	Discontinued
0.8212	Intermediate Similarity	NPD8313	Approved
0.8212	Intermediate Similarity	NPD8312	Approved
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8166	Intermediate Similarity	NPD7411	Suspended
0.8161	Intermediate Similarity	NPD6232	Discontinued
0.8144	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5403	Approved
0.8125	Intermediate Similarity	NPD7473	Discontinued
0.8118	Intermediate Similarity	NPD6801	Discontinued
0.8101	Intermediate Similarity	NPD7685	Pre-registration
0.8079	Intermediate Similarity	NPD7228	Approved
0.8079	Intermediate Similarity	NPD3751	Discontinued
0.807	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7988	Intermediate Similarity	NPD1549	Phase 2
0.7966	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7819	Suspended
0.7964	Intermediate Similarity	NPD6799	Approved
0.7955	Intermediate Similarity	NPD3787	Discontinued
0.7927	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7886	Intermediate Similarity	NPD6234	Discontinued
0.7865	Intermediate Similarity	NPD7435	Discontinued
0.7846	Intermediate Similarity	NPD8151	Discontinued
0.7844	Intermediate Similarity	NPD6190	Approved
0.7829	Intermediate Similarity	NPD3749	Approved
0.7811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1510	Phase 2
0.7803	Intermediate Similarity	NPD37	Approved
0.7801	Intermediate Similarity	NPD6777	Approved
0.7801	Intermediate Similarity	NPD6782	Approved
0.7801	Intermediate Similarity	NPD6778	Approved
0.7801	Intermediate Similarity	NPD6780	Approved
0.7801	Intermediate Similarity	NPD6779	Approved
0.7801	Intermediate Similarity	NPD6776	Approved
0.7801	Intermediate Similarity	NPD6781	Approved
0.7784	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4967	Phase 2
0.7771	Intermediate Similarity	NPD4966	Approved
0.7771	Intermediate Similarity	NPD4965	Approved
0.7766	Intermediate Similarity	NPD7783	Phase 2
0.7766	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD8455	Phase 2
0.7758	Intermediate Similarity	NPD2796	Approved
0.7751	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7266	Discontinued
0.7688	Intermediate Similarity	NPD6599	Discontinued
0.7679	Intermediate Similarity	NPD3750	Approved
0.767	Intermediate Similarity	NPD7768	Phase 2
0.7641	Intermediate Similarity	NPD7870	Phase 2
0.7641	Intermediate Similarity	NPD7871	Phase 2
0.7626	Intermediate Similarity	NPD7874	Approved
0.7626	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD230	Phase 1
0.7622	Intermediate Similarity	NPD1933	Approved
0.7609	Intermediate Similarity	NPD7240	Approved
0.7598	Intermediate Similarity	NPD1247	Approved
0.759	Intermediate Similarity	NPD7697	Approved
0.759	Intermediate Similarity	NPD7696	Phase 3
0.759	Intermediate Similarity	NPD7698	Approved
0.7584	Intermediate Similarity	NPD919	Approved
0.7561	Intermediate Similarity	NPD943	Approved
0.7561	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1613	Approved
0.756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2935	Discontinued
0.7545	Intermediate Similarity	NPD1551	Phase 2
0.7539	Intermediate Similarity	NPD6534	Approved
0.7539	Intermediate Similarity	NPD6535	Approved
0.7538	Intermediate Similarity	NPD6823	Phase 2
0.7525	Intermediate Similarity	NPD7701	Phase 2
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD447	Suspended
0.7514	Intermediate Similarity	NPD3926	Phase 2
0.7475	Intermediate Similarity	NPD7584	Approved
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7461	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1240	Approved
0.7423	Intermediate Similarity	NPD7700	Phase 2
0.7423	Intermediate Similarity	NPD7699	Phase 2
0.7413	Intermediate Similarity	NPD7801	Approved
0.7407	Intermediate Similarity	NPD8150	Discontinued
0.7399	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD1607	Approved
0.7343	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7458	Discontinued
0.733	Intermediate Similarity	NPD3226	Approved
0.7323	Intermediate Similarity	NPD7680	Approved
0.7317	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD920	Approved
0.7306	Intermediate Similarity	NPD6213	Phase 3
0.7306	Intermediate Similarity	NPD6212	Phase 3
0.7306	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2534	Approved
0.7299	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2533	Approved
0.7299	Intermediate Similarity	NPD2532	Approved
0.7296	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7549	Discontinued
0.7286	Intermediate Similarity	NPD8320	Phase 1
0.7286	Intermediate Similarity	NPD8319	Approved
0.7273	Intermediate Similarity	NPD5953	Discontinued
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7264	Intermediate Similarity	NPD7585	Approved
0.7256	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2313	Discontinued
0.7225	Intermediate Similarity	NPD8434	Phase 2
0.7214	Intermediate Similarity	NPD7583	Approved
0.7207	Intermediate Similarity	NPD6844	Discontinued
0.7186	Intermediate Similarity	NPD6233	Phase 2
0.7184	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7286	Phase 2
0.7134	Intermediate Similarity	NPD1203	Approved
0.7127	Intermediate Similarity	NPD5353	Approved
0.711	Intermediate Similarity	NPD1243	Approved
0.7108	Intermediate Similarity	NPD6832	Phase 2
0.7093	Intermediate Similarity	NPD2346	Discontinued
0.7076	Intermediate Similarity	NPD2799	Discontinued
0.7076	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD9269	Phase 2
0.7053	Intermediate Similarity	NPD7039	Approved
0.7053	Intermediate Similarity	NPD7038	Approved
0.7048	Intermediate Similarity	NPD9494	Approved
0.7045	Intermediate Similarity	NPD7390	Discontinued
0.7043	Intermediate Similarity	NPD5242	Approved
0.7028	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8127	Discontinued
0.7024	Intermediate Similarity	NPD6798	Discontinued
0.7011	Intermediate Similarity	NPD2800	Approved
0.7011	Intermediate Similarity	NPD6674	Discontinued
0.7011	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7005	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1091	Approved
0.6994	Remote Similarity	NPD2344	Approved
0.6974	Remote Similarity	NPD4287	Approved
0.6971	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6386	Approved
0.6961	Remote Similarity	NPD6385	Approved
0.6943	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5005	Approved
0.6931	Remote Similarity	NPD5006	Approved
0.693	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8059	Phase 3
0.6927	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4360	Phase 2
0.6919	Remote Similarity	NPD4363	Phase 3
0.6919	Remote Similarity	NPD7097	Phase 1
0.691	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5124	Phase 1
0.6901	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5711	Approved
0.6898	Remote Similarity	NPD5710	Approved
0.6898	Remote Similarity	NPD7229	Phase 3

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