NPASS Compound

Structure

NPC472562 OpenBabel07101718332D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.0739 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3340 -0.2181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1128 0.6199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6128 -3.7102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1128 -1.1121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1128 -1.1121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1128 -2.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0250 -1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6128 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1128 -1.1121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1128 -2.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6128 -1.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6128 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6128 -0.2461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6128 -3.7102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6128 -1.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 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 -2.0250 -2.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 7 13 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 12 2 1 1 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 14 1 6 0 0 0 19 28 1 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.16
Volume:	389.128
LogP:	4.834
LogD:	3.677
LogS:	-5.823
# Rotatable Bonds:	6
TPSA:	55.38
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	3.582
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.687
MDCK Permeability:	2.816330743371509e-05
Pgp-inhibitor:	0.661
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	91.32902526855469%
Volume Distribution (VD):	0.838
Pgp-substrate:	10.8765230178833%

ADMET: Metabolism

CYP1A2-inhibitor:	0.22
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.95
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.89
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.746
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.885

ADMET: Excretion

Clearance (CL):	13.191
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.362
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.468
Skin Sensitization:	0.921
Carcinogencity:	0.852
Eye Corrosion:	0.003
Eye Irritation:	0.181
Respiratory Toxicity:	0.521

Download Data

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

Natural Product: NPC472562

Natural Product ID:	NPC472562
*Common Name:**	NURXSAWWSQDCDU-BUXKBTBVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NURXSAWWSQDCDU-BUXKBTBVSA-N
Standard InCHI:	InChI=1S/C22H24O6/c1-6-7-13-8-17-22(27-11-26-17)18-12(2)19(28-20(13)18)14-9-15(23-3)21(25-5)16(10-14)24-4/h6,8-10,12,19H,1,7,11H2,2-5H3/t12-,19-/m0/s1
SMILES:	C=CCc1cc2OCOc2c2c1O[C@@H]([C@H]2C)c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577183
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO33212	ocotea cymosa	Species	Lauraceae	Eukaryota	stems or bark	Zahamena National Park, 1728'45?S, 04844'10?E, Madagascar	2000-JAN	PMID[25650896]

☑ 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	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1381	Organism	Aedes aegypti	Aedes aegypti	mortality	>=	80.0	%	PMID[558065]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	450.0	nM	PMID[558065]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4700.0	nM	PMID[558065]

☑ 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 NPC472562 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	544
0.1-0.2	1718
0.2-0.3	4937
0.3-0.4	12414
0.4-0.5	5674
0.5-0.6	4895
0.6-0.7	8334
0.7-0.8	3230
0.8-0.85	720
0.85-0.9	190
0.9-0.95	34
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC80326
0.9638	High Similarity	NPC205316
0.9632	High Similarity	NPC58137
0.9632	High Similarity	NPC300798
0.9562	High Similarity	NPC174522
0.9496	High Similarity	NPC180953
0.9478	High Similarity	NPC170779
0.9478	High Similarity	NPC90083
0.9433	High Similarity	NPC71726
0.9403	High Similarity	NPC266848
0.9403	High Similarity	NPC136750
0.9338	High Similarity	NPC78047
0.9328	High Similarity	NPC72046
0.9328	High Similarity	NPC65183
0.9328	High Similarity	NPC261812
0.9328	High Similarity	NPC7744
0.9281	High Similarity	NPC311057
0.9265	High Similarity	NPC189474
0.9254	High Similarity	NPC192255
0.9231	High Similarity	NPC240521
0.922	High Similarity	NPC11422
0.922	High Similarity	NPC178014
0.922	High Similarity	NPC42716
0.922	High Similarity	NPC474749
0.9214	High Similarity	NPC474808
0.9209	High Similarity	NPC312199
0.9191	High Similarity	NPC474478
0.9191	High Similarity	NPC31530
0.9178	High Similarity	NPC159922
0.9161	High Similarity	NPC166584
0.9161	High Similarity	NPC301961
0.9155	High Similarity	NPC162193
0.9137	High Similarity	NPC216434
0.9137	High Similarity	NPC103448
0.9124	High Similarity	NPC25333
0.9124	High Similarity	NPC49235
0.9124	High Similarity	NPC148893
0.9091	High Similarity	NPC116019
0.9065	High Similarity	NPC9068
0.9058	High Similarity	NPC121651
0.9037	High Similarity	NPC237169
0.9037	High Similarity	NPC470624
0.9034	High Similarity	NPC238140
0.903	High Similarity	NPC158471
0.903	High Similarity	NPC57119
0.903	High Similarity	NPC222127
0.903	High Similarity	NPC226862
0.903	High Similarity	NPC82862
0.903	High Similarity	NPC165128
0.9028	High Similarity	NPC270751
0.9021	High Similarity	NPC226540
0.9007	High Similarity	NPC474295
0.9	High Similarity	NPC226547
0.8993	High Similarity	NPC477938
0.8993	High Similarity	NPC185908
0.8993	High Similarity	NPC196420
0.8986	High Similarity	NPC474139
0.8971	High Similarity	NPC227160
0.8971	High Similarity	NPC82111
0.8955	High Similarity	NPC473093
0.8955	High Similarity	NPC8050
0.8955	High Similarity	NPC473092
0.8955	High Similarity	NPC98745
0.8951	High Similarity	NPC307466
0.8929	High Similarity	NPC113550
0.8921	High Similarity	NPC197166
0.8921	High Similarity	NPC11453
0.8921	High Similarity	NPC32189
0.8897	High Similarity	NPC233224
0.8897	High Similarity	NPC271208
0.8889	High Similarity	NPC281864
0.8889	High Similarity	NPC33832
0.8889	High Similarity	NPC54321
0.8889	High Similarity	NPC328682
0.8881	High Similarity	NPC45257
0.8881	High Similarity	NPC112571
0.8881	High Similarity	NPC50683
0.8881	High Similarity	NPC93323
0.8881	High Similarity	NPC280092
0.8881	High Similarity	NPC12641
0.8881	High Similarity	NPC285725
0.8873	High Similarity	NPC41782
0.8865	High Similarity	NPC46591
0.8865	High Similarity	NPC27495
0.8865	High Similarity	NPC254759
0.8865	High Similarity	NPC160283
0.8865	High Similarity	NPC284464
0.8865	High Similarity	NPC177868
0.8857	High Similarity	NPC283949
0.8849	High Similarity	NPC150534
0.8841	High Similarity	NPC196937
0.8841	High Similarity	NPC1474
0.8811	High Similarity	NPC298317
0.8811	High Similarity	NPC47633
0.8811	High Similarity	NPC102044
0.8811	High Similarity	NPC85264
0.8811	High Similarity	NPC255566
0.8803	High Similarity	NPC87725
0.8803	High Similarity	NPC263261
0.8794	High Similarity	NPC292882
0.8794	High Similarity	NPC6369
0.8794	High Similarity	NPC292487
0.8794	High Similarity	NPC30951
0.8786	High Similarity	NPC143895
0.8786	High Similarity	NPC172818
0.8786	High Similarity	NPC25695
0.8784	High Similarity	NPC302610
0.8777	High Similarity	NPC256776
0.8777	High Similarity	NPC145722
0.8777	High Similarity	NPC185680
0.8776	High Similarity	NPC472710
0.8776	High Similarity	NPC472709
0.8768	High Similarity	NPC171928
0.8768	High Similarity	NPC158526
0.8768	High Similarity	NPC100223
0.8768	High Similarity	NPC16830
0.8768	High Similarity	NPC230219
0.8768	High Similarity	NPC129687
0.8768	High Similarity	NPC33611
0.875	High Similarity	NPC172171
0.875	High Similarity	NPC63879
0.875	High Similarity	NPC31707
0.875	High Similarity	NPC79429
0.875	High Similarity	NPC239254
0.875	High Similarity	NPC471667
0.875	High Similarity	NPC217635
0.8741	High Similarity	NPC186845
0.8741	High Similarity	NPC253878
0.8741	High Similarity	NPC9891
0.8741	High Similarity	NPC287124
0.8741	High Similarity	NPC88297
0.8741	High Similarity	NPC107161
0.8732	High Similarity	NPC56091
0.8731	High Similarity	NPC34902
0.8731	High Similarity	NPC18449
0.8731	High Similarity	NPC191768
0.8731	High Similarity	NPC92869
0.8731	High Similarity	NPC283170
0.8731	High Similarity	NPC121783
0.8716	High Similarity	NPC474975
0.8707	High Similarity	NPC51328
0.8707	High Similarity	NPC286235
0.8707	High Similarity	NPC55158
0.8705	High Similarity	NPC26394
0.8705	High Similarity	NPC58585
0.8699	High Similarity	NPC16269
0.8699	High Similarity	NPC21776
0.869	High Similarity	NPC475868
0.869	High Similarity	NPC43508
0.869	High Similarity	NPC476301
0.8681	High Similarity	NPC218510
0.8681	High Similarity	NPC76415
0.8681	High Similarity	NPC81638
0.8681	High Similarity	NPC12728
0.8681	High Similarity	NPC477616
0.8681	High Similarity	NPC258083
0.8681	High Similarity	NPC185071
0.8671	High Similarity	NPC311530
0.8671	High Similarity	NPC471414
0.8671	High Similarity	NPC247291
0.8662	High Similarity	NPC471388
0.8652	High Similarity	NPC173660
0.8649	High Similarity	NPC98624
0.8643	High Similarity	NPC47181
0.8643	High Similarity	NPC16485
0.8639	High Similarity	NPC130449
0.8639	High Similarity	NPC248132
0.8639	High Similarity	NPC175976
0.8633	High Similarity	NPC219671
0.8633	High Similarity	NPC104077
0.8633	High Similarity	NPC259742
0.8633	High Similarity	NPC475856
0.8633	High Similarity	NPC147616
0.863	High Similarity	NPC154971
0.863	High Similarity	NPC252286
0.8623	High Similarity	NPC476399
0.8623	High Similarity	NPC258483
0.8621	High Similarity	NPC477701
0.8621	High Similarity	NPC326144
0.8621	High Similarity	NPC141569
0.8621	High Similarity	NPC166884
0.8611	High Similarity	NPC229172
0.8611	High Similarity	NPC176586
0.8611	High Similarity	NPC230538
0.8611	High Similarity	NPC103637
0.8611	High Similarity	NPC246947
0.8611	High Similarity	NPC36531
0.8611	High Similarity	NPC210354
0.8609	High Similarity	NPC164152
0.8601	High Similarity	NPC184797
0.8601	High Similarity	NPC309124
0.8601	High Similarity	NPC259519
0.8592	High Similarity	NPC474039
0.8582	High Similarity	NPC211231
0.8582	High Similarity	NPC142547
0.8582	High Similarity	NPC195022
0.8582	High Similarity	NPC126409
0.8582	High Similarity	NPC134968
0.8582	High Similarity	NPC174191
0.8582	High Similarity	NPC135777

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 NPC472562 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	910
0.2-0.3	1992
0.3-0.4	2785
0.4-0.5	1554
0.5-0.6	875
0.6-0.7	536
0.7-0.8	62
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD3705	Approved
0.8194	Intermediate Similarity	NPD4966	Approved
0.8194	Intermediate Similarity	NPD4965	Approved
0.8194	Intermediate Similarity	NPD4967	Phase 2
0.8089	Intermediate Similarity	NPD6234	Discontinued
0.8038	Intermediate Similarity	NPD5494	Approved
0.8028	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD37	Approved
0.7987	Intermediate Similarity	NPD7199	Phase 2
0.7986	Intermediate Similarity	NPD1613	Approved
0.7986	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6674	Discontinued
0.7888	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD5283	Phase 1
0.7832	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD3018	Phase 2
0.7762	Intermediate Similarity	NPD2861	Phase 2
0.7762	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7228	Approved
0.7742	Intermediate Similarity	NPD1653	Approved
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.766	Intermediate Similarity	NPD2981	Phase 2
0.7613	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2983	Phase 2
0.7606	Intermediate Similarity	NPD2982	Phase 2
0.7589	Intermediate Similarity	NPD1610	Phase 2
0.7564	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7240	Approved
0.7547	Intermediate Similarity	NPD3383	Approved
0.7547	Intermediate Similarity	NPD3384	Approved
0.7547	Intermediate Similarity	NPD3382	Approved
0.753	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7468	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1091	Approved
0.7419	Intermediate Similarity	NPD5058	Phase 3
0.7415	Intermediate Similarity	NPD4625	Phase 3
0.7391	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4060	Phase 1
0.7376	Intermediate Similarity	NPD1357	Approved
0.7372	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD1247	Approved
0.7329	Intermediate Similarity	NPD1934	Approved
0.732	Intermediate Similarity	NPD1375	Discontinued
0.7305	Intermediate Similarity	NPD1548	Phase 1
0.7284	Intermediate Similarity	NPD2801	Approved
0.7278	Intermediate Similarity	NPD7054	Approved
0.7255	Intermediate Similarity	NPD3539	Phase 1
0.7251	Intermediate Similarity	NPD6559	Discontinued
0.7248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4749	Approved
0.7239	Intermediate Similarity	NPD3817	Phase 2
0.7239	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7472	Approved
0.7222	Intermediate Similarity	NPD1611	Approved
0.7212	Intermediate Similarity	NPD919	Approved
0.7209	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3540	Phase 1
0.7197	Intermediate Similarity	NPD7124	Phase 2
0.7195	Intermediate Similarity	NPD3882	Suspended
0.7192	Intermediate Similarity	NPD8651	Approved
0.719	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6331	Phase 2
0.7179	Intermediate Similarity	NPD7466	Approved
0.717	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3454	Phase 3
0.7126	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5976	Discontinued
0.7123	Intermediate Similarity	NPD5327	Phase 3
0.711	Intermediate Similarity	NPD7808	Phase 3
0.711	Intermediate Similarity	NPD7549	Discontinued
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7105	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5762	Approved
0.7097	Intermediate Similarity	NPD5763	Approved
0.7095	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6797	Phase 2
0.7091	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.7081	Intermediate Similarity	NPD4210	Discontinued
0.7078	Intermediate Similarity	NPD5588	Approved
0.7078	Intermediate Similarity	NPD4108	Discontinued
0.7075	Intermediate Similarity	NPD6696	Suspended
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.707	Intermediate Similarity	NPD3892	Phase 2
0.707	Intermediate Similarity	NPD4110	Phase 3
0.707	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7251	Discontinued
0.7048	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3926	Phase 2
0.7032	Intermediate Similarity	NPD2796	Approved
0.7014	Intermediate Similarity	NPD5691	Approved
0.7013	Intermediate Similarity	NPD4538	Approved
0.7013	Intermediate Similarity	NPD6111	Discontinued
0.7013	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4536	Approved
0.7007	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4675	Approved
0.6994	Remote Similarity	NPD4678	Approved
0.6993	Remote Similarity	NPD5735	Approved
0.6993	Remote Similarity	NPD5536	Phase 2
0.6993	Remote Similarity	NPD3657	Discovery
0.6987	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6005	Phase 3
0.6987	Remote Similarity	NPD6002	Phase 3
0.6987	Remote Similarity	NPD6004	Phase 3
0.6987	Remote Similarity	NPD7266	Discontinued
0.6982	Remote Similarity	NPD3787	Discontinued
0.6982	Remote Similarity	NPD6232	Discontinued
0.6981	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6387	Discontinued
0.6972	Remote Similarity	NPD7157	Approved
0.6972	Remote Similarity	NPD6671	Approved
0.697	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7819	Suspended
0.6966	Remote Similarity	NPD5125	Phase 3
0.6966	Remote Similarity	NPD5126	Approved
0.6959	Remote Similarity	NPD7473	Discontinued
0.6957	Remote Similarity	NPD2684	Approved
0.6957	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1137	Approved
0.6929	Remote Similarity	NPD1139	Approved
0.6928	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3620	Phase 2
0.6923	Remote Similarity	NPD2161	Phase 2
0.6923	Remote Similarity	NPD2438	Suspended
0.6918	Remote Similarity	NPD3496	Discontinued
0.6908	Remote Similarity	NPD5111	Phase 2
0.6908	Remote Similarity	NPD5110	Phase 2
0.6908	Remote Similarity	NPD5109	Approved
0.6903	Remote Similarity	NPD7097	Phase 1
0.6901	Remote Similarity	NPD4481	Phase 3
0.6899	Remote Similarity	NPD4237	Approved
0.6899	Remote Similarity	NPD4236	Phase 3
0.6899	Remote Similarity	NPD1652	Phase 2
0.6897	Remote Similarity	NPD5585	Approved
0.6894	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7028	Phase 2
0.6883	Remote Similarity	NPD1933	Approved
0.6882	Remote Similarity	NPD7680	Approved
0.6879	Remote Similarity	NPD5535	Approved
0.6879	Remote Similarity	NPD7843	Approved
0.6879	Remote Similarity	NPD1138	Approved
0.6871	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD2978	Approved
0.6867	Remote Similarity	NPD2977	Approved
0.6863	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6233	Phase 2
0.6859	Remote Similarity	NPD5960	Phase 3
0.6859	Remote Similarity	NPD3748	Approved
0.6855	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD17	Approved
0.6845	Remote Similarity	NPD7075	Discontinued
0.6839	Remote Similarity	NPD2157	Approved
0.6835	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2424	Discontinued
0.6832	Remote Similarity	NPD6799	Approved
0.6832	Remote Similarity	NPD1511	Approved
0.6829	Remote Similarity	NPD4005	Discontinued
0.6828	Remote Similarity	NPD5006	Approved
0.6828	Remote Similarity	NPD5005	Approved
0.6826	Remote Similarity	NPD2560	Approved
0.6826	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2563	Approved
0.6826	Remote Similarity	NPD5402	Approved
0.6824	Remote Similarity	NPD8127	Discontinued
0.6818	Remote Similarity	NPD2979	Phase 3
0.6818	Remote Similarity	NPD4140	Approved
0.6816	Remote Similarity	NPD6843	Phase 3
0.6816	Remote Similarity	NPD6841	Approved
0.6816	Remote Similarity	NPD6842	Approved
0.6816	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2935	Discontinued
0.6813	Remote Similarity	NPD2677	Approved
0.681	Remote Similarity	NPD920	Approved
0.6809	Remote Similarity	NPD228	Approved
0.6807	Remote Similarity	NPD6801	Discontinued
0.6797	Remote Similarity	NPD6798	Discontinued
0.6797	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7119	Phase 2
0.6792	Remote Similarity	NPD5177	Phase 3
0.679	Remote Similarity	NPD7004	Clinical (unspecified phase)

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