NPASS Compound

Structure

CID167479 OpenBabel06191715542D 23 27 0 0 0 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -3.8005 2.5827 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 -1.5000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -2.5981 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 1.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 2.4781 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 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 15 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 20 1 0 0 0 0 7 10 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 21 1 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.05
Volume:	297.325
LogP:	4.37
LogD:	3.026
LogS:	-6.647
# Rotatable Bonds:	1
TPSA:	61.81
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	2.468
Fsp3:	0.056
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:	-4.711
MDCK Permeability:	3.8030957512091845e-05
Pgp-inhibitor:	0.816
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	94.2674331665039%
Volume Distribution (VD):	0.816
Pgp-substrate:	5.4679131507873535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.594
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	9.883
Half-life (T1/2):	0.125

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.272
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.381
Skin Sensitization:	0.105
Carcinogencity:	0.94
Eye Corrosion:	0.003
Eye Irritation:	0.425
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC167479

Natural Product ID:	NPC167479
*Common Name:**	Pongaglabrone
IUPAC Name:	2-(1,3-benzodioxol-5-yl)furo[2,3-h]chromen-4-one
Synonyms:	Pongaglabrone
Standard InCHIKey:	OLRNTGNFKYRPHW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H10O5/c19-13-8-16(10-1-3-15-17(7-10)22-9-21-15)23-18-11(13)2-4-14-12(18)5-6-20-14/h1-8H,9H2
SMILES:	c1cc2c(cc1c1cc(=O)c3ccc4c(cco4)c3o1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL583961
PubChem CID:	10957726
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]
NPO3037	Derris indica	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[19515570]
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]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	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	6

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	45670.0	nM	PMID[531336]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	6800.0	nM	PMID[531337]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	6400.0	nM	PMID[531337]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	3400.0	nM	PMID[531337]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	8200.0	nM	PMID[531337]
NPT2	Others	Unspecified		IC50	=	8.6	%	PMID[531335]

☑ 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 NPC167479 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	680
0.1-0.2	2420
0.2-0.3	5919
0.3-0.4	11973
0.4-0.5	4985
0.5-0.6	4713
0.6-0.7	5896
0.7-0.8	4918
0.8-0.85	1070
0.85-0.9	105
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC41853
0.9752	High Similarity	NPC62640
0.9571	High Similarity	NPC66804
0.9568	High Similarity	NPC157522
0.9509	High Similarity	NPC72455
0.9317	High Similarity	NPC65846
0.9114	High Similarity	NPC130015
0.9114	High Similarity	NPC38361
0.9096	High Similarity	NPC475964
0.9074	High Similarity	NPC109238
0.9024	High Similarity	NPC187923
0.9024	High Similarity	NPC38914
0.9006	High Similarity	NPC310206
0.9	High Similarity	NPC233776
0.8994	High Similarity	NPC68882
0.8988	High Similarity	NPC290304
0.8988	High Similarity	NPC236327
0.8987	High Similarity	NPC135303
0.8987	High Similarity	NPC148423
0.8981	High Similarity	NPC306788
0.8976	High Similarity	NPC211309
0.8963	High Similarity	NPC110257
0.8957	High Similarity	NPC34376
0.8957	High Similarity	NPC264293
0.8951	High Similarity	NPC113055
0.8944	High Similarity	NPC155063
0.8931	High Similarity	NPC472407
0.8922	High Similarity	NPC190351
0.8916	High Similarity	NPC241820
0.8902	High Similarity	NPC18284
0.8902	High Similarity	NPC273021
0.8882	High Similarity	NPC478238
0.8875	High Similarity	NPC153008
0.8875	High Similarity	NPC148497
0.8875	High Similarity	NPC292460
0.8834	High Similarity	NPC250076
0.8827	High Similarity	NPC261484
0.8827	High Similarity	NPC261090
0.882	High Similarity	NPC478213
0.882	High Similarity	NPC244371
0.882	High Similarity	NPC41719
0.882	High Similarity	NPC279930
0.8797	High Similarity	NPC198427
0.8788	High Similarity	NPC302741
0.878	High Similarity	NPC131557
0.878	High Similarity	NPC243509
0.8773	High Similarity	NPC258644
0.8773	High Similarity	NPC82733
0.8773	High Similarity	NPC76458
0.8765	High Similarity	NPC3273
0.8765	High Similarity	NPC284353
0.8743	High Similarity	NPC67450
0.8743	High Similarity	NPC210460
0.8743	High Similarity	NPC193881
0.8743	High Similarity	NPC155264
0.8735	High Similarity	NPC179464
0.8734	High Similarity	NPC190572
0.8727	High Similarity	NPC304387
0.8727	High Similarity	NPC94155
0.8727	High Similarity	NPC216092
0.872	High Similarity	NPC33320
0.872	High Similarity	NPC15764
0.8704	High Similarity	NPC57211
0.8698	High Similarity	NPC131866
0.8696	High Similarity	NPC279061
0.8675	High Similarity	NPC234536
0.8675	High Similarity	NPC478199
0.8675	High Similarity	NPC19948
0.8675	High Similarity	NPC125991
0.8675	High Similarity	NPC78612
0.8675	High Similarity	NPC193998
0.8671	High Similarity	NPC224687
0.8667	High Similarity	NPC139876
0.8659	High Similarity	NPC19097
0.8655	High Similarity	NPC469601
0.8642	High Similarity	NPC52623
0.8642	High Similarity	NPC263676
0.8642	High Similarity	NPC253872
0.8642	High Similarity	NPC104728
0.8642	High Similarity	NPC35544
0.8634	High Similarity	NPC472406
0.8614	High Similarity	NPC99968
0.8614	High Similarity	NPC296540
0.8614	High Similarity	NPC309335
0.8606	High Similarity	NPC215375
0.8606	High Similarity	NPC257914
0.8606	High Similarity	NPC62518
0.8606	High Similarity	NPC238405
0.8606	High Similarity	NPC104459
0.858	High Similarity	NPC116604
0.8571	High Similarity	NPC179015
0.8571	High Similarity	NPC173149
0.8571	High Similarity	NPC88445
0.8555	High Similarity	NPC469600
0.8554	High Similarity	NPC19554
0.8554	High Similarity	NPC269906
0.8554	High Similarity	NPC43971
0.8554	High Similarity	NPC285973
0.8554	High Similarity	NPC225624
0.8554	High Similarity	NPC74749
0.8553	High Similarity	NPC136278
0.8553	High Similarity	NPC296575
0.8553	High Similarity	NPC471590
0.8545	High Similarity	NPC167595
0.8539	High Similarity	NPC60848
0.8538	High Similarity	NPC223375
0.8538	High Similarity	NPC475825
0.8528	High Similarity	NPC40033
0.8519	High Similarity	NPC189270
0.8519	High Similarity	NPC5840
0.8519	High Similarity	NPC191104
0.8512	High Similarity	NPC470178
0.8509	High Similarity	NPC476342
0.8506	High Similarity	NPC183843
0.8506	High Similarity	NPC104682
0.8503	High Similarity	NPC260640
0.8503	High Similarity	NPC295009
0.8503	High Similarity	NPC162668
0.8491	Intermediate Similarity	NPC113089
0.8488	Intermediate Similarity	NPC233956
0.8488	Intermediate Similarity	NPC277510
0.8488	Intermediate Similarity	NPC310794
0.8485	Intermediate Similarity	NPC45131
0.8485	Intermediate Similarity	NPC301897
0.848	Intermediate Similarity	NPC144288
0.848	Intermediate Similarity	NPC135370
0.8476	Intermediate Similarity	NPC472408
0.8476	Intermediate Similarity	NPC128961
0.8476	Intermediate Similarity	NPC186507
0.8475	Intermediate Similarity	NPC73703
0.8471	Intermediate Similarity	NPC247973
0.8462	Intermediate Similarity	NPC470773
0.8462	Intermediate Similarity	NPC300053
0.8452	Intermediate Similarity	NPC219861
0.8452	Intermediate Similarity	NPC469575
0.8447	Intermediate Similarity	NPC74539
0.8447	Intermediate Similarity	NPC304443
0.8447	Intermediate Similarity	NPC205522
0.8443	Intermediate Similarity	NPC220582
0.8443	Intermediate Similarity	NPC78944
0.8443	Intermediate Similarity	NPC298093
0.8443	Intermediate Similarity	NPC304839
0.8439	Intermediate Similarity	NPC472607
0.8438	Intermediate Similarity	NPC246903
0.843	Intermediate Similarity	NPC248593
0.843	Intermediate Similarity	NPC28589
0.8428	Intermediate Similarity	NPC9966
0.8428	Intermediate Similarity	NPC476054
0.8428	Intermediate Similarity	NPC70853
0.8424	Intermediate Similarity	NPC278010
0.8424	Intermediate Similarity	NPC250769
0.8424	Intermediate Similarity	NPC295608
0.8421	Intermediate Similarity	NPC471287
0.8415	Intermediate Similarity	NPC166201
0.8412	Intermediate Similarity	NPC277480
0.8412	Intermediate Similarity	NPC119589
0.8412	Intermediate Similarity	NPC113093
0.8402	Intermediate Similarity	NPC470772
0.8402	Intermediate Similarity	NPC15819
0.8395	Intermediate Similarity	NPC63256
0.8395	Intermediate Similarity	NPC10304
0.8393	Intermediate Similarity	NPC15212
0.8393	Intermediate Similarity	NPC258331
0.8393	Intermediate Similarity	NPC188486
0.8393	Intermediate Similarity	NPC470756
0.8391	Intermediate Similarity	NPC156635
0.8391	Intermediate Similarity	NPC325176
0.8391	Intermediate Similarity	NPC107244
0.8385	Intermediate Similarity	NPC231013
0.8385	Intermediate Similarity	NPC216314
0.8385	Intermediate Similarity	NPC120924
0.8385	Intermediate Similarity	NPC14958
0.8385	Intermediate Similarity	NPC106461
0.8385	Intermediate Similarity	NPC40818
0.8385	Intermediate Similarity	NPC110639
0.8385	Intermediate Similarity	NPC215932
0.8385	Intermediate Similarity	NPC195919
0.8383	Intermediate Similarity	NPC16935
0.8383	Intermediate Similarity	NPC196879
0.8383	Intermediate Similarity	NPC50430
0.8383	Intermediate Similarity	NPC125713
0.8375	Intermediate Similarity	NPC17262
0.8375	Intermediate Similarity	NPC293201
0.8373	Intermediate Similarity	NPC470625
0.8373	Intermediate Similarity	NPC180340
0.8373	Intermediate Similarity	NPC472461
0.8372	Intermediate Similarity	NPC281835
0.8372	Intermediate Similarity	NPC212748
0.8372	Intermediate Similarity	NPC51404
0.8365	Intermediate Similarity	NPC29536
0.8365	Intermediate Similarity	NPC185607
0.8364	Intermediate Similarity	NPC472462
0.8364	Intermediate Similarity	NPC131725
0.8363	Intermediate Similarity	NPC320789
0.8363	Intermediate Similarity	NPC42892
0.8363	Intermediate Similarity	NPC471288
0.8363	Intermediate Similarity	NPC135345
0.8354	Intermediate Similarity	NPC170169
0.8353	Intermediate Similarity	NPC37183
0.8353	Intermediate Similarity	NPC165720

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 NPC167479 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	555
0.1-0.2	1042
0.2-0.3	2090
0.3-0.4	2794
0.4-0.5	1599
0.5-0.6	740
0.6-0.7	229
0.7-0.8	81
0.8-0.85	15
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8957	High Similarity	NPD1247	Approved
0.872	High Similarity	NPD919	Approved
0.858	High Similarity	NPD3818	Discontinued
0.8447	Intermediate Similarity	NPD920	Approved
0.8443	Intermediate Similarity	NPD5494	Approved
0.8438	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6559	Discontinued
0.8313	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3926	Phase 2
0.8095	Intermediate Similarity	NPD3817	Phase 2
0.8084	Intermediate Similarity	NPD1934	Approved
0.8047	Intermediate Similarity	NPD3882	Suspended
0.8036	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD2801	Approved
0.8012	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7472	Approved
0.7955	Intermediate Similarity	NPD7074	Phase 3
0.7937	Intermediate Similarity	NPD2796	Approved
0.7927	Intermediate Similarity	NPD1511	Approved
0.7921	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1512	Approved
0.7821	Intermediate Similarity	NPD7808	Phase 3
0.7816	Intermediate Similarity	NPD6232	Discontinued
0.7811	Intermediate Similarity	NPD7411	Suspended
0.7809	Intermediate Similarity	NPD6797	Phase 2
0.7784	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7251	Discontinued
0.7751	Intermediate Similarity	NPD4380	Phase 2
0.7733	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6166	Phase 2
0.7719	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7819	Suspended
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3749	Approved
0.7661	Intermediate Similarity	NPD6801	Discontinued
0.7657	Intermediate Similarity	NPD7199	Phase 2
0.7654	Intermediate Similarity	NPD1510	Phase 2
0.7622	Intermediate Similarity	NPD1549	Phase 2
0.7605	Intermediate Similarity	NPD6799	Approved
0.7605	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7075	Discontinued
0.7578	Intermediate Similarity	NPD1933	Approved
0.7572	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4965	Approved
0.7528	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5402	Approved
0.747	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6234	Discontinued
0.7442	Intermediate Similarity	NPD6599	Discontinued
0.7439	Intermediate Similarity	NPD3748	Approved
0.7414	Intermediate Similarity	NPD1465	Phase 2
0.736	Intermediate Similarity	NPD6959	Discontinued
0.7356	Intermediate Similarity	NPD37	Approved
0.7353	Intermediate Similarity	NPD5401	Approved
0.7349	Intermediate Similarity	NPD2344	Approved
0.7349	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7768	Phase 2
0.7322	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1240	Approved
0.7289	Intermediate Similarity	NPD1551	Phase 2
0.7287	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2313	Discontinued
0.7283	Intermediate Similarity	NPD3226	Approved
0.7267	Intermediate Similarity	NPD5403	Approved
0.7262	Intermediate Similarity	NPD2800	Approved
0.7253	Intermediate Similarity	NPD3751	Discontinued
0.7251	Intermediate Similarity	NPD2533	Approved
0.7251	Intermediate Similarity	NPD2532	Approved
0.7251	Intermediate Similarity	NPD2534	Approved
0.7246	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD3750	Approved
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1607	Approved
0.7195	Intermediate Similarity	NPD943	Approved
0.7181	Intermediate Similarity	NPD8434	Phase 2
0.7176	Intermediate Similarity	NPD2309	Approved
0.7158	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD447	Suspended
0.7151	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD5006	Approved
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD3787	Discontinued
0.7127	Intermediate Similarity	NPD6808	Phase 2
0.7112	Intermediate Similarity	NPD8313	Approved
0.7112	Intermediate Similarity	NPD8312	Approved
0.7101	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5242	Approved
0.7083	Intermediate Similarity	NPD2935	Discontinued
0.7049	Intermediate Similarity	NPD2403	Approved
0.7048	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2346	Discontinued
0.7033	Intermediate Similarity	NPD7229	Phase 3
0.7031	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1653	Approved
0.7026	Intermediate Similarity	NPD4420	Approved
0.7024	Intermediate Similarity	NPD2799	Discontinued
0.7005	Intermediate Similarity	NPD7240	Approved
0.697	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6280	Approved
0.6966	Remote Similarity	NPD6279	Approved
0.6952	Remote Similarity	NPD5953	Discontinued
0.6951	Remote Similarity	NPD6832	Phase 2
0.6946	Remote Similarity	NPD230	Phase 1
0.6935	Remote Similarity	NPD7286	Phase 2
0.6933	Remote Similarity	NPD2798	Approved
0.6931	Remote Similarity	NPD8151	Discontinued
0.6927	Remote Similarity	NPD8455	Phase 2
0.6915	Remote Similarity	NPD7685	Pre-registration
0.691	Remote Similarity	NPD6386	Approved
0.691	Remote Similarity	NPD6385	Approved
0.6893	Remote Similarity	NPD7458	Discontinued
0.6889	Remote Similarity	NPD5353	Approved
0.6886	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1613	Approved
0.6882	Remote Similarity	NPD2163	Approved
0.6871	Remote Similarity	NPD3266	Approved
0.6871	Remote Similarity	NPD3267	Approved
0.6851	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4287	Approved
0.6833	Remote Similarity	NPD5760	Phase 2
0.6833	Remote Similarity	NPD5761	Phase 2
0.6832	Remote Similarity	NPD7584	Approved
0.6824	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4628	Phase 3
0.6816	Remote Similarity	NPD5889	Approved
0.6816	Remote Similarity	NPD5890	Approved
0.6788	Remote Similarity	NPD9494	Approved
0.6788	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6779	Approved
0.6784	Remote Similarity	NPD6780	Approved
0.6784	Remote Similarity	NPD6777	Approved
0.6784	Remote Similarity	NPD6781	Approved
0.6784	Remote Similarity	NPD6782	Approved
0.6784	Remote Similarity	NPD6776	Approved
0.6784	Remote Similarity	NPD6778	Approved
0.6763	Remote Similarity	NPD2654	Approved
0.6761	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5711	Approved
0.6757	Remote Similarity	NPD5710	Approved
0.6733	Remote Similarity	NPD7871	Phase 2
0.6733	Remote Similarity	NPD7870	Phase 2
0.6728	Remote Similarity	NPD3705	Approved
0.6725	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4846	Phase 2
0.6705	Remote Similarity	NPD7390	Discontinued
0.6704	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2296	Approved
0.6699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7783	Phase 2
0.6686	Remote Similarity	NPD4307	Phase 2
0.6684	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7435	Discontinued
0.6683	Remote Similarity	NPD7696	Phase 3
0.6683	Remote Similarity	NPD7698	Approved
0.6683	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD6585	Discontinued
0.6667	Remote Similarity	NPD1296	Phase 2
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8285	Discontinued
0.6628	Remote Similarity	NPD7033	Discontinued
0.6627	Remote Similarity	NPD1019	Discontinued
0.6625	Remote Similarity	NPD5536	Phase 2
0.6612	Remote Similarity	NPD4288	Approved
0.6608	Remote Similarity	NPD6651	Approved
0.6607	Remote Similarity	NPD3027	Phase 3
0.6605	Remote Similarity	NPD17	Approved
0.6601	Remote Similarity	NPD7680	Approved
0.6591	Remote Similarity	NPD6190	Approved
0.6583	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4361	Phase 2
0.6568	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3764	Approved
0.6566	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6764	Approved
0.6562	Remote Similarity	NPD6765	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