NPASS Compound

Structure

NPC472156 OpenBabel07101718202D 28 32 0 0 1 0 0 0 0 0999 V2000 0.7366 3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3689 -0.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3689 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3689 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2350 1.9342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5029 -1.0658 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1294 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 1.9342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2350 0.9342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6369 -0.5658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5029 0.9342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6369 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1010 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 -2.0658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1010 0.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2291 -1.0658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 1.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 1.2029 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 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 9 1 0 0 0 0 4 9 1 0 0 0 0 5 13 2 0 0 0 0 6 14 2 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 17 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 1 0 0 0 12 18 1 0 0 0 0 12 22 1 1 0 0 0 13 16 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 15 23 2 0 0 0 0 17 24 1 1 0 0 0 18 20 1 0 0 0 0 18 25 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 27 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.1
Volume:	363.56
LogP:	1.076
LogD:	0.628
LogS:	-3.219
# Rotatable Bonds:	0
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	5.079
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.663
MDCK Permeability:	1.1747303688025568e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.748
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.286
Plasma Protein Binding (PPB):	80.4671401977539%
Volume Distribution (VD):	0.986
Pgp-substrate:	12.328940391540527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.638
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.311
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	2.212
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.588
Rat Oral Acute Toxicity:	0.726
Maximum Recommended Daily Dose:	0.37
Skin Sensitization:	0.094
Carcinogencity:	0.722
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.811

Download Data

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

Natural Product: NPC472156

Natural Product ID:	NPC472156
*Common Name:**	QUYXDKPCDHWNLZ-OHUKFJGISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QUYXDKPCDHWNLZ-OHUKFJGISA-N
Standard InCHI:	InChI=1S/C20H18O8/c21-11-8-15(23)19(26)10(17(11)24)7-12(22)18(25)20(19)27-13-5-1-3-9-4-2-6-14(28-20)16(9)13/h1-7,11-12,17-18,21-22,24-26H,8H2/t11-,12-,17+,18+,19+/m0/s1
SMILES:	C1C(C(C2=CC(C(C3(C2(C1=O)O)OC4=CC=CC5=C4C(=CC=C5)O3)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342636
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO33512	berkleasmium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25237727]

☑ 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
MIC	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[492829]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[492829]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[492829]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[492829]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[492829]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[492829]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[492829]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[492829]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[492829]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[492829]

☑ 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 NPC472156 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	410
0.1-0.2	1557
0.2-0.3	3418
0.3-0.4	8190
0.4-0.5	9707
0.5-0.6	5076
0.6-0.7	6220
0.7-0.8	7352
0.8-0.85	738
0.85-0.9	22
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC472150
0.961	High Similarity	NPC472153
0.9487	High Similarity	NPC74371
0.9487	High Similarity	NPC120677
0.9427	High Similarity	NPC75944
0.9367	High Similarity	NPC175082
0.8896	High Similarity	NPC137460
0.8896	High Similarity	NPC472152
0.8882	High Similarity	NPC472154
0.8875	High Similarity	NPC73148
0.8874	High Similarity	NPC197461
0.8834	High Similarity	NPC103633
0.8827	High Similarity	NPC11608
0.8827	High Similarity	NPC297404
0.8701	High Similarity	NPC288531
0.8701	High Similarity	NPC97662
0.8693	High Similarity	NPC472155
0.8675	High Similarity	NPC193920
0.8634	High Similarity	NPC193749
0.8554	High Similarity	NPC222455
0.8554	High Similarity	NPC67424
0.8519	High Similarity	NPC183402
0.8516	High Similarity	NPC173630
0.8512	High Similarity	NPC470438
0.8506	High Similarity	NPC314672
0.8506	High Similarity	NPC133585
0.8503	High Similarity	NPC84265
0.8503	High Similarity	NPC265214
0.8503	High Similarity	NPC282987
0.8503	High Similarity	NPC245014
0.8485	Intermediate Similarity	NPC277205
0.8462	Intermediate Similarity	NPC3718
0.8452	Intermediate Similarity	NPC476405
0.8452	Intermediate Similarity	NPC257404
0.8452	Intermediate Similarity	NPC117260
0.8452	Intermediate Similarity	NPC151704
0.8434	Intermediate Similarity	NPC56077
0.8434	Intermediate Similarity	NPC197285
0.8434	Intermediate Similarity	NPC21100
0.8434	Intermediate Similarity	NPC276222
0.8434	Intermediate Similarity	NPC308404
0.8434	Intermediate Similarity	NPC179950
0.8434	Intermediate Similarity	NPC88789
0.8434	Intermediate Similarity	NPC281131
0.8434	Intermediate Similarity	NPC145038
0.8434	Intermediate Similarity	NPC274618
0.8434	Intermediate Similarity	NPC118284
0.8434	Intermediate Similarity	NPC253662
0.8421	Intermediate Similarity	NPC153578
0.8421	Intermediate Similarity	NPC244903
0.8421	Intermediate Similarity	NPC114257
0.8421	Intermediate Similarity	NPC299149
0.8421	Intermediate Similarity	NPC277710
0.8415	Intermediate Similarity	NPC470125
0.8412	Intermediate Similarity	NPC470949
0.8412	Intermediate Similarity	NPC272656
0.8412	Intermediate Similarity	NPC169733
0.8412	Intermediate Similarity	NPC61904
0.8412	Intermediate Similarity	NPC8573
0.8412	Intermediate Similarity	NPC144097
0.8412	Intermediate Similarity	NPC65563
0.8412	Intermediate Similarity	NPC475246
0.8408	Intermediate Similarity	NPC474422
0.8405	Intermediate Similarity	NPC57072
0.8405	Intermediate Similarity	NPC231475
0.8402	Intermediate Similarity	NPC470336
0.8402	Intermediate Similarity	NPC470335
0.8402	Intermediate Similarity	NPC24043
0.8402	Intermediate Similarity	NPC101026
0.8402	Intermediate Similarity	NPC85368
0.8402	Intermediate Similarity	NPC42773
0.8402	Intermediate Similarity	NPC169977
0.8402	Intermediate Similarity	NPC45522
0.8402	Intermediate Similarity	NPC21666
0.8397	Intermediate Similarity	NPC271076
0.8397	Intermediate Similarity	NPC23807
0.8395	Intermediate Similarity	NPC307938
0.8395	Intermediate Similarity	NPC261866
0.8395	Intermediate Similarity	NPC323593
0.8395	Intermediate Similarity	NPC203500
0.8393	Intermediate Similarity	NPC235260
0.8393	Intermediate Similarity	NPC254855
0.8393	Intermediate Similarity	NPC155763
0.8393	Intermediate Similarity	NPC156869
0.8393	Intermediate Similarity	NPC95866
0.8393	Intermediate Similarity	NPC67326
0.8393	Intermediate Similarity	NPC29958
0.8393	Intermediate Similarity	NPC285197
0.8393	Intermediate Similarity	NPC255157
0.8393	Intermediate Similarity	NPC67105
0.8393	Intermediate Similarity	NPC136042
0.8393	Intermediate Similarity	NPC259896
0.8393	Intermediate Similarity	NPC20505
0.8393	Intermediate Similarity	NPC8704
0.8393	Intermediate Similarity	NPC287884
0.8383	Intermediate Similarity	NPC84362
0.8383	Intermediate Similarity	NPC317489
0.8383	Intermediate Similarity	NPC45618
0.8383	Intermediate Similarity	NPC275454
0.8383	Intermediate Similarity	NPC160156
0.8383	Intermediate Similarity	NPC295082
0.8383	Intermediate Similarity	NPC173637
0.8383	Intermediate Similarity	NPC127546
0.8383	Intermediate Similarity	NPC223424
0.8383	Intermediate Similarity	NPC58716
0.8383	Intermediate Similarity	NPC146792
0.8383	Intermediate Similarity	NPC92565
0.8383	Intermediate Similarity	NPC52550
0.8382	Intermediate Similarity	NPC231254
0.8373	Intermediate Similarity	NPC240431
0.8373	Intermediate Similarity	NPC19388
0.8373	Intermediate Similarity	NPC280923
0.8373	Intermediate Similarity	NPC55786
0.8372	Intermediate Similarity	NPC170203
0.8372	Intermediate Similarity	NPC315221
0.8372	Intermediate Similarity	NPC6709
0.8366	Intermediate Similarity	NPC472151
0.8364	Intermediate Similarity	NPC216752
0.8364	Intermediate Similarity	NPC77660
0.8364	Intermediate Similarity	NPC189142
0.8363	Intermediate Similarity	NPC37668
0.8363	Intermediate Similarity	NPC253521
0.8363	Intermediate Similarity	NPC470334
0.8363	Intermediate Similarity	NPC113836
0.8363	Intermediate Similarity	NPC35167
0.8354	Intermediate Similarity	NPC187379
0.8354	Intermediate Similarity	NPC136761
0.8354	Intermediate Similarity	NPC470405
0.8354	Intermediate Similarity	NPC471079
0.8354	Intermediate Similarity	NPC304741
0.8354	Intermediate Similarity	NPC328093
0.8353	Intermediate Similarity	NPC43211
0.8353	Intermediate Similarity	NPC34267
0.8353	Intermediate Similarity	NPC264735
0.8353	Intermediate Similarity	NPC115760
0.8353	Intermediate Similarity	NPC214621
0.8353	Intermediate Similarity	NPC210094
0.8353	Intermediate Similarity	NPC223426
0.8353	Intermediate Similarity	NPC81042
0.8353	Intermediate Similarity	NPC108202
0.8353	Intermediate Similarity	NPC237435
0.8353	Intermediate Similarity	NPC135277
0.8353	Intermediate Similarity	NPC253685
0.8353	Intermediate Similarity	NPC49344
0.8353	Intermediate Similarity	NPC470667
0.8353	Intermediate Similarity	NPC101191
0.8353	Intermediate Similarity	NPC477848
0.8344	Intermediate Similarity	NPC77672
0.8344	Intermediate Similarity	NPC108831
0.8344	Intermediate Similarity	NPC197304
0.8344	Intermediate Similarity	NPC474398
0.8344	Intermediate Similarity	NPC6985
0.8344	Intermediate Similarity	NPC182634
0.8344	Intermediate Similarity	NPC474441
0.8344	Intermediate Similarity	NPC54802
0.8344	Intermediate Similarity	NPC78263
0.8344	Intermediate Similarity	NPC177742
0.8344	Intermediate Similarity	NPC474401
0.8344	Intermediate Similarity	NPC476026
0.8344	Intermediate Similarity	NPC135391
0.8344	Intermediate Similarity	NPC133671
0.8343	Intermediate Similarity	NPC3583
0.8343	Intermediate Similarity	NPC134532
0.8343	Intermediate Similarity	NPC203259
0.8343	Intermediate Similarity	NPC155877
0.8343	Intermediate Similarity	NPC175107
0.8343	Intermediate Similarity	NPC267254
0.8343	Intermediate Similarity	NPC471748
0.8343	Intermediate Similarity	NPC271385
0.8343	Intermediate Similarity	NPC30432
0.8343	Intermediate Similarity	NPC245452
0.8343	Intermediate Similarity	NPC76128
0.8343	Intermediate Similarity	NPC176740
0.8343	Intermediate Similarity	NPC60735
0.8343	Intermediate Similarity	NPC259152
0.8343	Intermediate Similarity	NPC26230
0.8343	Intermediate Similarity	NPC190003
0.8343	Intermediate Similarity	NPC5029
0.8343	Intermediate Similarity	NPC301683
0.8343	Intermediate Similarity	NPC471725
0.8343	Intermediate Similarity	NPC111536
0.8343	Intermediate Similarity	NPC33054
0.8333	Intermediate Similarity	NPC112755
0.8333	Intermediate Similarity	NPC225434
0.8333	Intermediate Similarity	NPC226294
0.8333	Intermediate Similarity	NPC270578
0.8333	Intermediate Similarity	NPC219904
0.8333	Intermediate Similarity	NPC105025
0.8333	Intermediate Similarity	NPC52382
0.8333	Intermediate Similarity	NPC138927
0.8333	Intermediate Similarity	NPC217378
0.8333	Intermediate Similarity	NPC45638
0.8333	Intermediate Similarity	NPC120099
0.8333	Intermediate Similarity	NPC471457
0.8333	Intermediate Similarity	NPC58053
0.8333	Intermediate Similarity	NPC472381
0.8333	Intermediate Similarity	NPC259905
0.8333	Intermediate Similarity	NPC170675
0.8333	Intermediate Similarity	NPC227508
0.8333	Intermediate Similarity	NPC223747

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 NPC472156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	861
0.2-0.3	1841
0.3-0.4	2655
0.4-0.5	1878
0.5-0.6	973
0.6-0.7	452
0.7-0.8	126
0.8-0.85	9
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9423	High Similarity	NPD3787	Discontinued
0.9308	High Similarity	NPD3751	Discontinued
0.8353	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6797	Phase 2
0.8294	Intermediate Similarity	NPD7251	Discontinued
0.8263	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD6166	Phase 2
0.8263	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7808	Phase 3
0.8232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7472	Approved
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8118	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5402	Approved
0.8059	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7199	Phase 2
0.7952	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD3817	Phase 2
0.7879	Intermediate Similarity	NPD37	Approved
0.7879	Intermediate Similarity	NPD1934	Approved
0.787	Intermediate Similarity	NPD6959	Discontinued
0.7869	Intermediate Similarity	NPD6776	Approved
0.7869	Intermediate Similarity	NPD6779	Approved
0.7869	Intermediate Similarity	NPD6777	Approved
0.7869	Intermediate Similarity	NPD6778	Approved
0.7869	Intermediate Similarity	NPD6782	Approved
0.7869	Intermediate Similarity	NPD6780	Approved
0.7869	Intermediate Similarity	NPD6781	Approved
0.7866	Intermediate Similarity	NPD4380	Phase 2
0.7849	Intermediate Similarity	NPD7228	Approved
0.7844	Intermediate Similarity	NPD4966	Approved
0.7844	Intermediate Similarity	NPD4965	Approved
0.7844	Intermediate Similarity	NPD4967	Phase 2
0.7831	Intermediate Similarity	NPD8455	Phase 2
0.7831	Intermediate Similarity	NPD2801	Approved
0.7831	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7075	Discontinued
0.7797	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5403	Approved
0.7784	Intermediate Similarity	NPD8313	Approved
0.7784	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6234	Discontinued
0.7742	Intermediate Similarity	NPD7435	Discontinued
0.7738	Intermediate Similarity	NPD3882	Suspended
0.773	Intermediate Similarity	NPD1512	Approved
0.7725	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7819	Suspended
0.7702	Intermediate Similarity	NPD6190	Approved
0.767	Intermediate Similarity	NPD6559	Discontinued
0.7669	Intermediate Similarity	NPD5401	Approved
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6801	Discontinued
0.7654	Intermediate Similarity	NPD8150	Discontinued
0.7647	Intermediate Similarity	NPD7697	Approved
0.7647	Intermediate Similarity	NPD7698	Approved
0.7647	Intermediate Similarity	NPD7696	Phase 3
0.7619	Intermediate Similarity	NPD1465	Phase 2
0.7616	Intermediate Similarity	NPD6232	Discontinued
0.7607	Intermediate Similarity	NPD6799	Approved
0.7607	Intermediate Similarity	NPD1511	Approved
0.7606	Intermediate Similarity	NPD7870	Phase 2
0.7606	Intermediate Similarity	NPD7871	Phase 2
0.7602	Intermediate Similarity	NPD5494	Approved
0.7596	Intermediate Similarity	NPD6534	Approved
0.7596	Intermediate Similarity	NPD6535	Approved
0.7588	Intermediate Similarity	NPD3749	Approved
0.7586	Intermediate Similarity	NPD7473	Discontinued
0.7579	Intermediate Similarity	NPD7701	Phase 2
0.7574	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7240	Approved
0.7562	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8434	Phase 2
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7874	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.7473	Intermediate Similarity	NPD7700	Phase 2
0.7473	Intermediate Similarity	NPD7699	Phase 2
0.7461	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7783	Phase 2
0.7461	Intermediate Similarity	NPD7801	Approved
0.7452	Intermediate Similarity	NPD6233	Phase 2
0.744	Intermediate Similarity	NPD6599	Discontinued
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7429	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1653	Approved
0.7423	Intermediate Similarity	NPD3750	Approved
0.7407	Intermediate Similarity	NPD6823	Phase 2
0.7389	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD1091	Approved
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7349	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7229	Phase 3
0.7284	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7097	Phase 1
0.7261	Intermediate Similarity	NPD4908	Phase 1
0.7261	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6674	Discontinued
0.725	Intermediate Similarity	NPD6355	Discontinued
0.724	Intermediate Similarity	NPD8320	Phase 1
0.724	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD3748	Approved
0.7222	Intermediate Similarity	NPD1510	Phase 2
0.7215	Intermediate Similarity	NPD4625	Phase 3
0.7212	Intermediate Similarity	NPD4628	Phase 3
0.7197	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.7186	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7685	Pre-registration
0.7175	Intermediate Similarity	NPD3926	Phase 2
0.717	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7768	Phase 2
0.7108	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3027	Phase 3
0.7107	Intermediate Similarity	NPD7095	Approved
0.7089	Intermediate Similarity	NPD2861	Phase 2
0.7074	Intermediate Similarity	NPD6212	Phase 3
0.7074	Intermediate Similarity	NPD6213	Phase 3
0.7074	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1247	Approved
0.7048	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2532	Approved
0.7041	Intermediate Similarity	NPD2534	Approved
0.7041	Intermediate Similarity	NPD2533	Approved
0.7032	Intermediate Similarity	NPD1610	Phase 2
0.703	Intermediate Similarity	NPD5762	Approved
0.703	Intermediate Similarity	NPD7266	Discontinued
0.703	Intermediate Similarity	NPD2346	Discontinued
0.703	Intermediate Similarity	NPD5763	Approved
0.7026	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7680	Approved
0.6995	Remote Similarity	NPD2493	Approved
0.6995	Remote Similarity	NPD3452	Approved
0.6995	Remote Similarity	NPD3450	Approved
0.6995	Remote Similarity	NPD2494	Approved
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1608	Approved
0.6982	Remote Similarity	NPD7390	Discontinued
0.6977	Remote Similarity	NPD7458	Discontinued
0.6975	Remote Similarity	NPD1240	Approved
0.697	Remote Similarity	NPD1551	Phase 2
0.6963	Remote Similarity	NPD2973	Approved
0.6963	Remote Similarity	NPD2975	Approved
0.6963	Remote Similarity	NPD2974	Approved
0.6957	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3268	Approved
0.6949	Remote Similarity	NPD919	Approved
0.6943	Remote Similarity	NPD4749	Approved
0.6933	Remote Similarity	NPD1933	Approved
0.6923	Remote Similarity	NPD4002	Approved
0.6923	Remote Similarity	NPD4004	Approved
0.6918	Remote Similarity	NPD5647	Approved
0.6914	Remote Similarity	NPD4062	Phase 3
0.6909	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7584	Approved
0.6899	Remote Similarity	NPD3225	Approved
0.689	Remote Similarity	NPD1607	Approved
0.6888	Remote Similarity	NPD4582	Approved
0.6888	Remote Similarity	NPD4583	Approved
0.6886	Remote Similarity	NPD2424	Discontinued
0.6886	Remote Similarity	NPD2897	Discontinued
0.6883	Remote Similarity	NPD1548	Phase 1
0.6875	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8127	Discontinued
0.6867	Remote Similarity	NPD2935	Discontinued
0.6857	Remote Similarity	NPD6844	Discontinued
0.6856	Remote Similarity	NPD4580	Approved
0.6855	Remote Similarity	NPD2797	Approved
0.6852	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1652	Phase 2
0.6845	Remote Similarity	NPD2800	Approved
0.6829	Remote Similarity	NPD447	Suspended
0.6829	Remote Similarity	NPD5124	Phase 1
0.6829	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5058	Phase 3
0.6795	Remote Similarity	NPD17	Approved
0.6794	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD8059	Phase 3
0.6791	Remote Similarity	NPD7090	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