NPASS Compound

Structure

NPC41853 OpenBabel07101718232D 25 29 0 0 0 0 0 0 0 0999 V2000 0.8660 1.5000 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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -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 -2.5981 -0.5000 0.0000 C 0 0 0 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 -6.7350 -2.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 0.8660 -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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 22 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 18 1 0 0 0 0 12 20 2 0 0 0 0 13 16 2 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.06
Volume:	323.411
LogP:	4.53
LogD:	3.001
LogS:	-6.263
# Rotatable Bonds:	2
TPSA:	71.04
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.552
Synthetic Accessibility Score:	2.581
Fsp3:	0.105
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:	-4.726
MDCK Permeability:	4.350940798758529e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.287

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	90.66280364990234%
Volume Distribution (VD):	0.521
Pgp-substrate:	8.242854118347168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.432
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.807
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	9.552
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.554
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.654
Skin Sensitization:	0.382
Carcinogencity:	0.921
Eye Corrosion:	0.003
Eye Irritation:	0.483
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC41853

Natural Product ID:	NPC41853
*Common Name:**	BKQQOWSJCUCPPA-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BKQQOWSJCUCPPA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12O6/c1-21-19-11-4-5-22-15(11)8-17-18(19)12(20)7-14(25-17)10-2-3-13-16(6-10)24-9-23-13/h2-8H,9H2,1H3
SMILES:	COc1c2ccoc2cc2c1c(=O)cc(c1ccc3c(c1)OCO3)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581066
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001759] Furanoflavones

*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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	100000.0	nM	PMID[533887]

☑ 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 NPC41853 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	566
0.1-0.2	2160
0.2-0.3	5186
0.3-0.4	11416
0.4-0.5	6243
0.5-0.6	4256
0.6-0.7	5948
0.7-0.8	4837
0.8-0.85	1803
0.85-0.9	252
0.9-0.95	26
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC167479
0.9814	High Similarity	NPC62640
0.9632	High Similarity	NPC66804
0.963	High Similarity	NPC157522
0.9571	High Similarity	NPC72455
0.9379	High Similarity	NPC65846
0.9177	High Similarity	NPC130015
0.9177	High Similarity	NPC38361
0.9157	High Similarity	NPC475964
0.9136	High Similarity	NPC109238
0.9085	High Similarity	NPC187923
0.9068	High Similarity	NPC310206
0.9062	High Similarity	NPC233776
0.9057	High Similarity	NPC68882
0.9051	High Similarity	NPC135303
0.9051	High Similarity	NPC148423
0.9048	High Similarity	NPC236327
0.9048	High Similarity	NPC290304
0.9036	High Similarity	NPC211309
0.9018	High Similarity	NPC264293
0.9018	High Similarity	NPC34376
0.9012	High Similarity	NPC113055
0.9006	High Similarity	NPC155063
0.8982	High Similarity	NPC190351
0.897	High Similarity	NPC38914
0.8963	High Similarity	NPC273021
0.8963	High Similarity	NPC18284
0.8944	High Similarity	NPC478238
0.8938	High Similarity	NPC292460
0.8938	High Similarity	NPC153008
0.8938	High Similarity	NPC148497
0.8924	High Similarity	NPC306788
0.8909	High Similarity	NPC110257
0.8896	High Similarity	NPC250076
0.8889	High Similarity	NPC261484
0.8882	High Similarity	NPC41719
0.8882	High Similarity	NPC279930
0.8882	High Similarity	NPC244371
0.8882	High Similarity	NPC478213
0.8875	High Similarity	NPC472407
0.8862	High Similarity	NPC241820
0.8861	High Similarity	NPC198427
0.8848	High Similarity	NPC302741
0.8841	High Similarity	NPC243509
0.8841	High Similarity	NPC131557
0.8834	High Similarity	NPC76458
0.8834	High Similarity	NPC258644
0.8834	High Similarity	NPC82733
0.8827	High Similarity	NPC284353
0.8827	High Similarity	NPC3273
0.8802	High Similarity	NPC193881
0.8802	High Similarity	NPC210460
0.8802	High Similarity	NPC155264
0.8802	High Similarity	NPC67450
0.8797	High Similarity	NPC190572
0.8795	High Similarity	NPC179464
0.8788	High Similarity	NPC94155
0.8788	High Similarity	NPC216092
0.878	High Similarity	NPC15764
0.878	High Similarity	NPC33320
0.8773	High Similarity	NPC261090
0.8765	High Similarity	NPC57211
0.8758	High Similarity	NPC279061
0.8757	High Similarity	NPC131866
0.8735	High Similarity	NPC193998
0.8735	High Similarity	NPC78612
0.8735	High Similarity	NPC234536
0.8735	High Similarity	NPC478199
0.8735	High Similarity	NPC19948
0.8735	High Similarity	NPC125991
0.8734	High Similarity	NPC224687
0.8727	High Similarity	NPC139876
0.872	High Similarity	NPC19097
0.8713	High Similarity	NPC469601
0.8704	High Similarity	NPC52623
0.8704	High Similarity	NPC263676
0.8696	High Similarity	NPC472406
0.8675	High Similarity	NPC296540
0.8675	High Similarity	NPC99968
0.8675	High Similarity	NPC304387
0.8675	High Similarity	NPC309335
0.8667	High Similarity	NPC104459
0.8667	High Similarity	NPC257914
0.8667	High Similarity	NPC62518
0.8667	High Similarity	NPC238405
0.8667	High Similarity	NPC215375
0.8634	High Similarity	NPC88445
0.8631	High Similarity	NPC173149
0.8631	High Similarity	NPC179015
0.8616	High Similarity	NPC471590
0.8616	High Similarity	NPC296575
0.8616	High Similarity	NPC136278
0.8614	High Similarity	NPC74749
0.8614	High Similarity	NPC43971
0.8614	High Similarity	NPC19554
0.8614	High Similarity	NPC269906
0.8613	High Similarity	NPC469600
0.8606	High Similarity	NPC167595
0.8596	High Similarity	NPC60848
0.8596	High Similarity	NPC475825
0.8596	High Similarity	NPC223375
0.8589	High Similarity	NPC253872
0.8589	High Similarity	NPC40033
0.8589	High Similarity	NPC35544
0.8589	High Similarity	NPC104728
0.858	High Similarity	NPC191104
0.858	High Similarity	NPC5840
0.858	High Similarity	NPC189270
0.8571	High Similarity	NPC476342
0.8563	High Similarity	NPC295009
0.8563	High Similarity	NPC260640
0.8563	High Similarity	NPC183843
0.8563	High Similarity	NPC104682
0.8553	High Similarity	NPC113089
0.8547	High Similarity	NPC310794
0.8547	High Similarity	NPC233956
0.8547	High Similarity	NPC277510
0.8545	High Similarity	NPC301897
0.8545	High Similarity	NPC45131
0.8538	High Similarity	NPC135370
0.8538	High Similarity	NPC144288
0.8537	High Similarity	NPC186507
0.8537	High Similarity	NPC128961
0.8537	High Similarity	NPC472408
0.8529	High Similarity	NPC247973
0.8528	High Similarity	NPC116604
0.8521	High Similarity	NPC470773
0.8521	High Similarity	NPC300053
0.8512	High Similarity	NPC219861
0.8512	High Similarity	NPC469575
0.8509	High Similarity	NPC74539
0.8509	High Similarity	NPC304443
0.8509	High Similarity	NPC205522
0.8503	High Similarity	NPC285973
0.8503	High Similarity	NPC225624
0.8503	High Similarity	NPC304839
0.8503	High Similarity	NPC298093
0.8503	High Similarity	NPC220582
0.8503	High Similarity	NPC78944
0.8491	Intermediate Similarity	NPC70853
0.8491	Intermediate Similarity	NPC9966
0.8491	Intermediate Similarity	NPC476054
0.8485	Intermediate Similarity	NPC278010
0.8485	Intermediate Similarity	NPC295608
0.8485	Intermediate Similarity	NPC250769
0.848	Intermediate Similarity	NPC471287
0.8476	Intermediate Similarity	NPC166201
0.8471	Intermediate Similarity	NPC119589
0.8471	Intermediate Similarity	NPC113093
0.8471	Intermediate Similarity	NPC277480
0.8462	Intermediate Similarity	NPC470178
0.8462	Intermediate Similarity	NPC470772
0.8457	Intermediate Similarity	NPC10304
0.8457	Intermediate Similarity	NPC63256
0.8452	Intermediate Similarity	NPC470756
0.8452	Intermediate Similarity	NPC188486
0.8452	Intermediate Similarity	NPC258331
0.8452	Intermediate Similarity	NPC15212
0.8452	Intermediate Similarity	NPC162668
0.8448	Intermediate Similarity	NPC156635
0.8448	Intermediate Similarity	NPC107244
0.8448	Intermediate Similarity	NPC325176
0.8447	Intermediate Similarity	NPC14958
0.8447	Intermediate Similarity	NPC120924
0.8447	Intermediate Similarity	NPC195919
0.8447	Intermediate Similarity	NPC110639
0.8447	Intermediate Similarity	NPC106461
0.8447	Intermediate Similarity	NPC215932
0.8447	Intermediate Similarity	NPC231013
0.8447	Intermediate Similarity	NPC216314
0.8447	Intermediate Similarity	NPC40818
0.8443	Intermediate Similarity	NPC196879
0.8443	Intermediate Similarity	NPC50430
0.8443	Intermediate Similarity	NPC16935
0.8443	Intermediate Similarity	NPC125713
0.8438	Intermediate Similarity	NPC293201
0.8438	Intermediate Similarity	NPC17262
0.8434	Intermediate Similarity	NPC470625
0.8434	Intermediate Similarity	NPC180340
0.843	Intermediate Similarity	NPC281835
0.843	Intermediate Similarity	NPC212748
0.843	Intermediate Similarity	NPC51404
0.8428	Intermediate Similarity	NPC185607
0.8428	Intermediate Similarity	NPC29536
0.8427	Intermediate Similarity	NPC73703
0.8424	Intermediate Similarity	NPC472462
0.8424	Intermediate Similarity	NPC131725
0.8421	Intermediate Similarity	NPC135345
0.8421	Intermediate Similarity	NPC320789
0.8421	Intermediate Similarity	NPC471288
0.8415	Intermediate Similarity	NPC170169
0.8412	Intermediate Similarity	NPC37183
0.8405	Intermediate Similarity	NPC238366
0.8402	Intermediate Similarity	NPC312056
0.8402	Intermediate Similarity	NPC84515
0.8402	Intermediate Similarity	NPC81679
0.8402	Intermediate Similarity	NPC61141
0.8402	Intermediate Similarity	NPC272722
0.84	Intermediate Similarity	NPC67302
0.8395	Intermediate Similarity	NPC85233

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 NPC41853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	459
0.1-0.2	1017
0.2-0.3	1968
0.3-0.4	2780
0.4-0.5	1714
0.5-0.6	827
0.6-0.7	263
0.7-0.8	92
0.8-0.85	25
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9018	High Similarity	NPD1247	Approved
0.878	High Similarity	NPD919	Approved
0.8529	High Similarity	NPD3818	Discontinued
0.8509	High Similarity	NPD920	Approved
0.8503	High Similarity	NPD5494	Approved
0.8439	Intermediate Similarity	NPD6559	Discontinued
0.8385	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD3926	Phase 2
0.8155	Intermediate Similarity	NPD3817	Phase 2
0.8144	Intermediate Similarity	NPD1934	Approved
0.8107	Intermediate Similarity	NPD3882	Suspended
0.8095	Intermediate Similarity	NPD2801	Approved
0.8095	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1243	Approved
0.8057	Intermediate Similarity	NPD7054	Approved
0.8011	Intermediate Similarity	NPD7074	Phase 3
0.8011	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD2796	Approved
0.7953	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1511	Approved
0.7877	Intermediate Similarity	NPD7808	Phase 3
0.7877	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6232	Discontinued
0.787	Intermediate Similarity	NPD7411	Suspended
0.7865	Intermediate Similarity	NPD6797	Phase 2
0.7841	Intermediate Similarity	NPD7473	Discontinued
0.7831	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7251	Discontinued
0.7784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6166	Phase 2
0.7784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD7819	Suspended
0.7778	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD5844	Phase 1
0.7753	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6801	Discontinued
0.7714	Intermediate Similarity	NPD7199	Phase 2
0.7706	Intermediate Similarity	NPD4380	Phase 2
0.7688	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6799	Approved
0.7644	Intermediate Similarity	NPD3749	Approved
0.7644	Intermediate Similarity	NPD7075	Discontinued
0.764	Intermediate Similarity	NPD1933	Approved
0.763	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1510	Phase 2
0.7586	Intermediate Similarity	NPD4965	Approved
0.7586	Intermediate Similarity	NPD4967	Phase 2
0.7586	Intermediate Similarity	NPD4966	Approved
0.7584	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1549	Phase 2
0.753	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD6599	Discontinued
0.7429	Intermediate Similarity	NPD5402	Approved
0.7416	Intermediate Similarity	NPD6959	Discontinued
0.7414	Intermediate Similarity	NPD37	Approved
0.741	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2344	Approved
0.7403	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3748	Approved
0.7386	Intermediate Similarity	NPD7768	Phase 2
0.7371	Intermediate Similarity	NPD1465	Phase 2
0.7362	Intermediate Similarity	NPD1240	Approved
0.7341	Intermediate Similarity	NPD3226	Approved
0.734	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2800	Approved
0.731	Intermediate Similarity	NPD2532	Approved
0.731	Intermediate Similarity	NPD5401	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD2533	Approved
0.7305	Intermediate Similarity	NPD1471	Phase 3
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1607	Approved
0.7246	Intermediate Similarity	NPD1551	Phase 2
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7235	Intermediate Similarity	NPD2309	Approved
0.7234	Intermediate Similarity	NPD8434	Phase 2
0.7225	Intermediate Similarity	NPD5403	Approved
0.7213	Intermediate Similarity	NPD3751	Discontinued
0.7213	Intermediate Similarity	NPD7228	Approved
0.7212	Intermediate Similarity	NPD447	Suspended
0.7207	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5006	Approved
0.7194	Intermediate Similarity	NPD5005	Approved
0.7182	Intermediate Similarity	NPD6808	Phase 2
0.7181	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3750	Approved
0.716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD5242	Approved
0.7108	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2403	Approved
0.7101	Intermediate Similarity	NPD2346	Discontinued
0.7088	Intermediate Similarity	NPD3787	Discontinued
0.7088	Intermediate Similarity	NPD7229	Phase 3
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4420	Approved
0.7074	Intermediate Similarity	NPD8312	Approved
0.7074	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD7240	Approved
0.703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6280	Approved
0.7022	Intermediate Similarity	NPD6279	Approved
0.7021	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6832	Phase 2
0.7006	Intermediate Similarity	NPD230	Phase 1
0.7005	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2798	Approved
0.6989	Remote Similarity	NPD7286	Phase 2
0.6989	Remote Similarity	NPD1653	Approved
0.698	Remote Similarity	NPD8151	Discontinued
0.6968	Remote Similarity	NPD7685	Pre-registration
0.6966	Remote Similarity	NPD6386	Approved
0.6966	Remote Similarity	NPD6385	Approved
0.6949	Remote Similarity	NPD7458	Discontinued
0.6944	Remote Similarity	NPD5353	Approved
0.6935	Remote Similarity	NPD2163	Approved
0.6933	Remote Similarity	NPD3267	Approved
0.6933	Remote Similarity	NPD3266	Approved
0.6889	Remote Similarity	NPD5760	Phase 2
0.6889	Remote Similarity	NPD8455	Phase 2
0.6889	Remote Similarity	NPD5761	Phase 2
0.6882	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7584	Approved
0.6879	Remote Similarity	NPD4628	Phase 3
0.6872	Remote Similarity	NPD5890	Approved
0.6872	Remote Similarity	NPD5889	Approved
0.6848	Remote Similarity	NPD9494	Approved
0.6845	Remote Similarity	NPD1613	Approved
0.6845	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6781	Approved
0.6834	Remote Similarity	NPD6778	Approved
0.6834	Remote Similarity	NPD6780	Approved
0.6834	Remote Similarity	NPD6782	Approved
0.6834	Remote Similarity	NPD6777	Approved
0.6834	Remote Similarity	NPD6776	Approved
0.6834	Remote Similarity	NPD6779	Approved
0.6821	Remote Similarity	NPD2654	Approved
0.6813	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD5710	Approved
0.6811	Remote Similarity	NPD5711	Approved
0.6807	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4287	Approved
0.679	Remote Similarity	NPD3705	Approved
0.6782	Remote Similarity	NPD7871	Phase 2
0.6782	Remote Similarity	NPD7870	Phase 2
0.6771	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7390	Discontinued
0.6758	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD2296	Approved
0.6748	Remote Similarity	NPD7783	Phase 2
0.6748	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4307	Phase 2
0.6738	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7698	Approved
0.6733	Remote Similarity	NPD7697	Approved
0.6733	Remote Similarity	NPD7696	Phase 3
0.6733	Remote Similarity	NPD7435	Discontinued
0.6726	Remote Similarity	NPD3268	Approved
0.6723	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7028	Phase 2
0.6722	Remote Similarity	NPD6585	Discontinued
0.67	Remote Similarity	NPD8285	Discontinued
0.6687	Remote Similarity	NPD5536	Phase 2
0.6687	Remote Similarity	NPD1019	Discontinued
0.6686	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7033	Discontinued
0.6682	Remote Similarity	NPD4846	Phase 2
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6651	Approved
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD17	Approved
0.665	Remote Similarity	NPD7680	Approved
0.6633	Remote Similarity	NPD4361	Phase 2
0.6633	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1296	Phase 2
0.6627	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1203	Approved
0.6615	Remote Similarity	NPD6764	Approved
0.6615	Remote Similarity	NPD6765	Approved
0.6602	Remote Similarity	NPD7701	Phase 2
0.6601	Remote Similarity	NPD6823	Phase 2
0.6597	Remote Similarity	NPD1729	Discontinued
0.6593	Remote Similarity	NPD7615	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