NPASS Compound

Structure

NPC473150 OpenBabel07101718322D 28 30 0 0 1 0 0 0 0 0999 V2000 -1.0361 4.0743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.4563 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 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 -0.0850 3.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 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 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 1 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 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 4.4344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 1.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 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 -1.7321 -0.0000 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 0.1229 2.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 3 4 2 0 0 0 0 3 17 1 0 0 0 0 4 25 1 0 0 0 0 5 9 1 0 0 0 0 5 16 1 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 7 28 1 0 0 0 0 8 6 1 6 0 0 0 8 10 1 0 0 0 0 8 26 1 0 0 0 0 9 17 1 1 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 1 0 0 0 11 12 1 0 0 0 0 11 22 1 6 0 0 0 12 14 1 0 0 0 0 12 23 1 1 0 0 0 13 15 1 0 0 0 0 13 16 1 6 0 0 0 13 17 1 0 0 0 0 14 26 1 0 0 0 0 14 27 1 6 0 0 0 15 25 1 0 0 0 0 15 27 1 1 0 0 0 16 2 1 1 0 0 0 16 28 1 0 0 0 0 17 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.15
Volume:	368.338
LogP:	-0.997
LogD:	-0.604
LogS:	-1.72
# Rotatable Bonds:	5
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.264
Synthetic Accessibility Score:	4.97
Fsp3:	0.824
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.164
MDCK Permeability:	0.0001274352107429877
Pgp-inhibitor:	0.002
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.898
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	20.45106315612793%
Volume Distribution (VD):	0.358
Pgp-substrate:	64.46363067626953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.036

ADMET: Excretion

Clearance (CL):	1.238
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.321
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.088
Carcinogencity:	0.954
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC473150

Natural Product ID:	NPC473150
*Common Name:**	CAFTUQNGDROXEZ-NINKYYIQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CAFTUQNGDROXEZ-NINKYYIQSA-N
Standard InCHI:	InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16-,17-/m1/s1
SMILES:	CC(=O)OC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622809
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid 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
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	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	6

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	38.5	%	PMID[496524]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	38.6	%	PMID[496524]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	39.1	%	PMID[496524]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	37.3	%	PMID[496524]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	37.7	%	PMID[496524]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	38.8	%	PMID[496524]

☑ 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 NPC473150 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	175
0.1-0.2	1889
0.2-0.3	6850
0.3-0.4	15229
0.4-0.5	9327
0.5-0.6	7358
0.6-0.7	1730
0.7-0.8	109
0.8-0.85	16
0.85-0.9	6
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC294643
1.0	High Similarity	NPC274274
0.9765	High Similarity	NPC93190
0.9535	High Similarity	NPC50464
0.9412	High Similarity	NPC171484
0.9412	High Similarity	NPC149018
0.8953	High Similarity	NPC98276
0.8953	High Similarity	NPC259296
0.8876	High Similarity	NPC22918
0.8764	High Similarity	NPC148534
0.8652	High Similarity	NPC258501
0.8478	Intermediate Similarity	NPC276298
0.828	Intermediate Similarity	NPC235051
0.8211	Intermediate Similarity	NPC6765
0.8211	Intermediate Similarity	NPC93869
0.82	Intermediate Similarity	NPC127235
0.8163	Intermediate Similarity	NPC216911
0.8125	Intermediate Similarity	NPC284063
0.8105	Intermediate Similarity	NPC274588
0.8061	Intermediate Similarity	NPC476211
0.8061	Intermediate Similarity	NPC476320
0.8041	Intermediate Similarity	NPC470684
0.8041	Intermediate Similarity	NPC470683
0.8041	Intermediate Similarity	NPC86843
0.8039	Intermediate Similarity	NPC110701
0.8	Intermediate Similarity	NPC329834
0.798	Intermediate Similarity	NPC3488
0.798	Intermediate Similarity	NPC287539
0.798	Intermediate Similarity	NPC27474
0.798	Intermediate Similarity	NPC476230
0.7941	Intermediate Similarity	NPC148270
0.7941	Intermediate Similarity	NPC80338
0.7941	Intermediate Similarity	NPC197813
0.7938	Intermediate Similarity	NPC161293
0.7938	Intermediate Similarity	NPC170527
0.7885	Intermediate Similarity	NPC193741
0.7843	Intermediate Similarity	NPC170432
0.7822	Intermediate Similarity	NPC475928
0.7822	Intermediate Similarity	NPC37240
0.7822	Intermediate Similarity	NPC329704
0.78	Intermediate Similarity	NPC476228
0.78	Intermediate Similarity	NPC20673
0.7736	Intermediate Similarity	NPC475924
0.7736	Intermediate Similarity	NPC475851
0.7723	Intermediate Similarity	NPC304163
0.7723	Intermediate Similarity	NPC35185
0.7723	Intermediate Similarity	NPC4899
0.7723	Intermediate Similarity	NPC177013
0.7723	Intermediate Similarity	NPC474730
0.7717	Intermediate Similarity	NPC136699
0.7717	Intermediate Similarity	NPC220167
0.77	Intermediate Similarity	NPC244878
0.7636	Intermediate Similarity	NPC219656
0.7629	Intermediate Similarity	NPC280390
0.7604	Intermediate Similarity	NPC117596
0.76	Intermediate Similarity	NPC151093
0.7576	Intermediate Similarity	NPC241911
0.7526	Intermediate Similarity	NPC66504
0.7526	Intermediate Similarity	NPC472126
0.7526	Intermediate Similarity	NPC472124
0.7526	Intermediate Similarity	NPC472125
0.7525	Intermediate Similarity	NPC306344
0.7525	Intermediate Similarity	NPC22149
0.7525	Intermediate Similarity	NPC255677
0.75	Intermediate Similarity	NPC472290
0.75	Intermediate Similarity	NPC233500
0.7475	Intermediate Similarity	NPC101051
0.7453	Intermediate Similarity	NPC208307
0.7451	Intermediate Similarity	NPC4637
0.7451	Intermediate Similarity	NPC98859
0.7451	Intermediate Similarity	NPC28304
0.7451	Intermediate Similarity	NPC219038
0.7451	Intermediate Similarity	NPC298255
0.7449	Intermediate Similarity	NPC61201
0.7434	Intermediate Similarity	NPC196130
0.7426	Intermediate Similarity	NPC96399
0.7426	Intermediate Similarity	NPC117066
0.7426	Intermediate Similarity	NPC469919
0.7426	Intermediate Similarity	NPC469918
0.7426	Intermediate Similarity	NPC223700
0.7423	Intermediate Similarity	NPC307699
0.7416	Intermediate Similarity	NPC279575
0.7404	Intermediate Similarity	NPC86095
0.74	Intermediate Similarity	NPC474297
0.7387	Intermediate Similarity	NPC472080
0.7379	Intermediate Similarity	NPC471599
0.7379	Intermediate Similarity	NPC13171
0.7379	Intermediate Similarity	NPC195510
0.7379	Intermediate Similarity	NPC106668
0.7374	Intermediate Similarity	NPC63897
0.7368	Intermediate Similarity	NPC219804
0.7363	Intermediate Similarity	NPC170595
0.7327	Intermediate Similarity	NPC263674
0.7327	Intermediate Similarity	NPC261372
0.7327	Intermediate Similarity	NPC58267
0.7308	Intermediate Similarity	NPC118761
0.7308	Intermediate Similarity	NPC197541
0.7308	Intermediate Similarity	NPC284929
0.7308	Intermediate Similarity	NPC27687
0.7308	Intermediate Similarity	NPC267869
0.7308	Intermediate Similarity	NPC234304
0.7292	Intermediate Similarity	NPC31349
0.7273	Intermediate Similarity	NPC470187
0.7264	Intermediate Similarity	NPC470170
0.7264	Intermediate Similarity	NPC470169
0.7255	Intermediate Similarity	NPC37866
0.7255	Intermediate Similarity	NPC157739
0.7212	Intermediate Similarity	NPC261117
0.7212	Intermediate Similarity	NPC222062
0.7212	Intermediate Similarity	NPC250545
0.7212	Intermediate Similarity	NPC310804
0.7188	Intermediate Similarity	NPC470657
0.7182	Intermediate Similarity	NPC287075
0.7157	Intermediate Similarity	NPC236580
0.7157	Intermediate Similarity	NPC304445
0.7157	Intermediate Similarity	NPC473555
0.7157	Intermediate Similarity	NPC278939
0.7157	Intermediate Similarity	NPC471770
0.7143	Intermediate Similarity	NPC276047
0.7143	Intermediate Similarity	NPC299527
0.7143	Intermediate Similarity	NPC267733
0.7129	Intermediate Similarity	NPC241407
0.7129	Intermediate Similarity	NPC291709
0.7117	Intermediate Similarity	NPC106446
0.7115	Intermediate Similarity	NPC67296
0.7113	Intermediate Similarity	NPC316629
0.7103	Intermediate Similarity	NPC470166
0.71	Intermediate Similarity	NPC474835
0.7087	Intermediate Similarity	NPC274458
0.7083	Intermediate Similarity	NPC470658
0.7083	Intermediate Similarity	NPC477747
0.7083	Intermediate Similarity	NPC477746
0.7079	Intermediate Similarity	NPC470659
0.7079	Intermediate Similarity	NPC470660
0.7071	Intermediate Similarity	NPC270908
0.7071	Intermediate Similarity	NPC231710
0.7071	Intermediate Similarity	NPC470573
0.7071	Intermediate Similarity	NPC120021
0.7071	Intermediate Similarity	NPC65665
0.7071	Intermediate Similarity	NPC216826
0.7048	Intermediate Similarity	NPC154452
0.7037	Intermediate Similarity	NPC295980
0.7019	Intermediate Similarity	NPC317019
0.7019	Intermediate Similarity	NPC473146
0.7019	Intermediate Similarity	NPC91497
0.7009	Intermediate Similarity	NPC165405
0.7	Intermediate Similarity	NPC472197
0.7	Intermediate Similarity	NPC470748
0.7	Intermediate Similarity	NPC472199
0.699	Remote Similarity	NPC347923
0.699	Remote Similarity	NPC153559
0.699	Remote Similarity	NPC476057
0.699	Remote Similarity	NPC182811
0.6981	Remote Similarity	NPC471467
0.6981	Remote Similarity	NPC197736
0.6975	Remote Similarity	NPC145287
0.697	Remote Similarity	NPC104129
0.697	Remote Similarity	NPC249408
0.697	Remote Similarity	NPC477748
0.6961	Remote Similarity	NPC240838
0.6952	Remote Similarity	NPC21064
0.6952	Remote Similarity	NPC144486
0.6952	Remote Similarity	NPC121072
0.6944	Remote Similarity	NPC469957
0.6944	Remote Similarity	NPC469959
0.6944	Remote Similarity	NPC474285
0.6944	Remote Similarity	NPC254538
0.6944	Remote Similarity	NPC108682
0.6944	Remote Similarity	NPC472263
0.6942	Remote Similarity	NPC42206
0.6931	Remote Similarity	NPC472195
0.6931	Remote Similarity	NPC238090
0.6931	Remote Similarity	NPC472196
0.6923	Remote Similarity	NPC124181
0.6923	Remote Similarity	NPC79449
0.6923	Remote Similarity	NPC473307
0.6923	Remote Similarity	NPC90819
0.6923	Remote Similarity	NPC249171
0.6923	Remote Similarity	NPC474957
0.6923	Remote Similarity	NPC49833
0.6903	Remote Similarity	NPC477031
0.69	Remote Similarity	NPC6414
0.69	Remote Similarity	NPC202886
0.69	Remote Similarity	NPC327253
0.69	Remote Similarity	NPC303451
0.6889	Remote Similarity	NPC248427
0.6887	Remote Similarity	NPC200672
0.6887	Remote Similarity	NPC80144
0.6887	Remote Similarity	NPC31085
0.6887	Remote Similarity	NPC214714
0.687	Remote Similarity	NPC5883
0.687	Remote Similarity	NPC44899
0.687	Remote Similarity	NPC304260
0.687	Remote Similarity	NPC29639
0.6869	Remote Similarity	NPC137368
0.6863	Remote Similarity	NPC159698
0.6863	Remote Similarity	NPC472198
0.6863	Remote Similarity	NPC256368
0.6857	Remote Similarity	NPC130792
0.6857	Remote Similarity	NPC79631

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 NPC473150 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	2462
0.2-0.3	4074
0.3-0.4	1709
0.4-0.5	475
0.5-0.6	239
0.6-0.7	34
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7188	Intermediate Similarity	NPD4249	Approved
0.7113	Intermediate Similarity	NPD4250	Approved
0.7113	Intermediate Similarity	NPD4251	Approved
0.7043	Intermediate Similarity	NPD7503	Approved
0.6752	Remote Similarity	NPD8033	Approved
0.6737	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7327	Approved
0.6638	Remote Similarity	NPD7328	Approved
0.6581	Remote Similarity	NPD7516	Approved
0.6562	Remote Similarity	NPD4819	Approved
0.6562	Remote Similarity	NPD4821	Approved
0.6562	Remote Similarity	NPD4820	Approved
0.6562	Remote Similarity	NPD4822	Approved
0.6526	Remote Similarity	NPD4271	Approved
0.6526	Remote Similarity	NPD4268	Approved
0.6525	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD8294	Approved
0.6471	Remote Similarity	NPD8379	Approved
0.6471	Remote Similarity	NPD8296	Approved
0.6471	Remote Similarity	NPD8335	Approved
0.6471	Remote Similarity	NPD8378	Approved
0.6471	Remote Similarity	NPD8380	Approved
0.6449	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD8133	Approved
0.6404	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6412	Phase 2
0.6333	Remote Similarity	NPD8513	Phase 3
0.6283	Remote Similarity	NPD6686	Approved
0.626	Remote Similarity	NPD7507	Approved
0.6207	Remote Similarity	NPD6053	Discontinued
0.62	Remote Similarity	NPD7154	Phase 3
0.6198	Remote Similarity	NPD8515	Approved
0.6198	Remote Similarity	NPD8516	Approved
0.6198	Remote Similarity	NPD8517	Approved
0.6117	Remote Similarity	NPD7524	Approved
0.6111	Remote Similarity	NPD7319	Approved
0.61	Remote Similarity	NPD6435	Approved
0.6095	Remote Similarity	NPD46	Approved
0.6095	Remote Similarity	NPD6698	Approved
0.604	Remote Similarity	NPD5362	Discontinued
0.6038	Remote Similarity	NPD7983	Approved
0.6038	Remote Similarity	NPD7637	Suspended
0.6018	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD8171	Discontinued
0.598	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7838	Discovery
0.5906	Remote Similarity	NPD7736	Approved
0.59	Remote Similarity	NPD5368	Approved
0.5893	Remote Similarity	NPD5344	Discontinued
0.5887	Remote Similarity	NPD6370	Approved
0.5882	Remote Similarity	NPD5332	Approved
0.5882	Remote Similarity	NPD6695	Phase 3
0.5882	Remote Similarity	NPD5331	Approved
0.5868	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6319	Approved
0.5842	Remote Similarity	NPD5369	Approved
0.5842	Remote Similarity	NPD4790	Discontinued
0.5827	Remote Similarity	NPD8293	Discontinued
0.5825	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7492	Approved
0.5794	Remote Similarity	NPD8340	Approved
0.5794	Remote Similarity	NPD8299	Approved
0.5794	Remote Similarity	NPD8341	Approved
0.5794	Remote Similarity	NPD8342	Approved
0.5789	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4269	Approved
0.5784	Remote Similarity	NPD4270	Approved
0.5776	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6371	Approved
0.5748	Remote Similarity	NPD6616	Approved
0.5743	Remote Similarity	NPD4252	Approved
0.5739	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6009	Approved
0.5728	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD3669	Approved
0.5726	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD5786	Approved
0.5703	Remote Similarity	NPD7078	Approved
0.5703	Remote Similarity	NPD8074	Phase 3
0.568	Remote Similarity	NPD6015	Approved
0.568	Remote Similarity	NPD6016	Approved
0.568	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7839	Suspended
0.5667	Remote Similarity	NPD6882	Approved
0.566	Remote Similarity	NPD7750	Discontinued
0.5652	Remote Similarity	NPD1407	Approved
0.5648	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD5988	Approved
0.5635	Remote Similarity	NPD8080	Discontinued
0.5625	Remote Similarity	NPD8451	Approved
0.562	Remote Similarity	NPD4632	Approved
0.5619	Remote Similarity	NPD5363	Approved
0.56	Remote Similarity	NPD6059	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