NPASS Compound

Structure

NPC296018 OpenBabel07101719512D 41 45 0 0 1 0 0 0 0 0999 V2000 -3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6472 0.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2460 1.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6527 0.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2350 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8337 2.1521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8283 2.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0649 -0.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1097 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -5.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8185 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2295 1.0295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4270 3.0657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4161 2.8566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 2.5227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4716 -1.2930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 -0.2749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -2.5933 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 -1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 10 2 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 11 1 0 0 0 0 6 16 2 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 17 2 0 0 0 0 9 38 1 0 0 0 0 10 24 1 0 0 0 0 11 26 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 19 2 0 0 0 0 14 30 1 0 0 0 0 15 20 2 0 0 0 0 15 31 1 0 0 0 0 16 20 1 0 0 0 0 16 32 1 0 0 0 0 17 19 1 0 0 0 0 17 39 1 0 0 0 0 18 9 1 6 0 0 0 18 21 1 0 0 0 0 18 40 1 0 0 0 0 19 22 1 0 0 0 0 20 33 1 0 0 0 0 21 23 1 0 0 0 0 21 34 1 1 0 0 0 22 25 1 0 0 0 0 22 35 2 0 0 0 0 23 27 1 0 0 0 0 23 36 1 6 0 0 0 24 25 2 0 0 0 0 24 39 1 0 0 0 0 25 41 1 0 0 0 0 26 37 2 0 0 0 0 26 38 1 0 0 0 0 27 40 1 0 0 0 0 27 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.1
Volume:	524.191
LogP:	2.419
LogD:	1.125
LogS:	-4.838
# Rotatable Bonds:	7
TPSA:	236.81
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.121
Synthetic Accessibility Score:	4.052
Fsp3:	0.185
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.203
MDCK Permeability:	1.0163133083551656e-05
Pgp-inhibitor:	0.2
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.321
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	93.18038177490234%
Volume Distribution (VD):	0.639
Pgp-substrate:	11.378660202026367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.606
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.606
CYP2C9-substrate:	0.453
CYP2D6-inhibitor:	0.357
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.236
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	6.548
Half-life (T1/2):	0.943

ADMET: Toxicity

hERG Blockers:	0.188
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.794
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.95
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.909
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC296018

Natural Product ID:	NPC296018
*Common Name:**	5,7-Dihydroxy-2-(4-Hydroxyphenyl)-4-Oxo-4H-Chromen-3-Yl-5-O-Alpha-L-(3,4,5-Trihydroxybenzoyl)Arabinofuranoside
IUPAC Name:	[(2S,3R,4R,5S)-5-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4-dihydroxyoxolan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	KBPZGUFFGQEGLH-GABSKDJNSA-N
Standard InCHI:	InChI=1S/C27H22O14/c28-12-3-1-10(2-4-12)24-25(22(35)19-14(30)7-13(29)8-17(19)39-24)41-27-23(36)21(34)18(40-27)9-38-26(37)11-5-15(31)20(33)16(32)6-11/h1-8,18,21,23,27-34,36H,9H2/t18-,21-,23+,27-/m0/s1
SMILES:	Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H]([C@@H]([C@H]1O)O)COC(=O)c1cc(O)c(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501025
PubChem CID:	11261607
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5909	Triplaris cumingiana	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730249]
NPO5909	Triplaris cumingiana	Species	Polygonaceae	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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	9.0	ug.mL-1	PMID[490581]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[490581]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[490581]

☑ 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 NPC296018 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	433
0.1-0.2	1845
0.2-0.3	4131
0.3-0.4	9204
0.4-0.5	9022
0.5-0.6	4370
0.6-0.7	5467
0.7-0.8	5290
0.8-0.85	1760
0.85-0.9	856
0.9-0.95	298
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC154741
0.9939	High Similarity	NPC476773
0.9758	High Similarity	NPC144097
0.9758	High Similarity	NPC61904
0.9699	High Similarity	NPC253521
0.9699	High Similarity	NPC37668
0.9699	High Similarity	NPC113836
0.9699	High Similarity	NPC35167
0.9697	High Similarity	NPC34267
0.9697	High Similarity	NPC223426
0.9697	High Similarity	NPC81042
0.9697	High Similarity	NPC214621
0.9634	High Similarity	NPC155763
0.9634	High Similarity	NPC235260
0.9634	High Similarity	NPC20505
0.9581	High Similarity	NPC139571
0.9581	High Similarity	NPC196127
0.9581	High Similarity	NPC217520
0.9581	High Similarity	NPC217387
0.9581	High Similarity	NPC258044
0.9581	High Similarity	NPC293626
0.9581	High Similarity	NPC267680
0.9576	High Similarity	NPC175107
0.9576	High Similarity	NPC190003
0.9573	High Similarity	NPC138927
0.9571	High Similarity	NPC67037
0.9571	High Similarity	NPC255615
0.9527	High Similarity	NPC36138
0.9527	High Similarity	NPC97119
0.9527	High Similarity	NPC135831
0.9527	High Similarity	NPC297503
0.9518	High Similarity	NPC4390
0.9515	High Similarity	NPC244776
0.9515	High Similarity	NPC72249
0.9515	High Similarity	NPC116864
0.9515	High Similarity	NPC149011
0.9515	High Similarity	NPC204937
0.9512	High Similarity	NPC48640
0.9512	High Similarity	NPC149244
0.9509	High Similarity	NPC34531
0.9471	High Similarity	NPC470416
0.9464	High Similarity	NPC477895
0.9461	High Similarity	NPC210094
0.9461	High Similarity	NPC101191
0.9461	High Similarity	NPC237435
0.9461	High Similarity	NPC115760
0.9461	High Similarity	NPC253685
0.9461	High Similarity	NPC49344
0.9461	High Similarity	NPC135277
0.9461	High Similarity	NPC43211
0.9458	High Similarity	NPC245452
0.9458	High Similarity	NPC153755
0.9455	High Similarity	NPC476771
0.9451	High Similarity	NPC274618
0.9451	High Similarity	NPC308404
0.9451	High Similarity	NPC253662
0.9451	High Similarity	NPC88789
0.9451	High Similarity	NPC254306
0.9451	High Similarity	NPC118284
0.9451	High Similarity	NPC145038
0.9451	High Similarity	NPC281131
0.9451	High Similarity	NPC56077
0.9451	High Similarity	NPC179950
0.9451	High Similarity	NPC276222
0.9412	High Similarity	NPC470718
0.9412	High Similarity	NPC162394
0.9412	High Similarity	NPC156785
0.9412	High Similarity	NPC241781
0.9405	High Similarity	NPC472385
0.9405	High Similarity	NPC198324
0.9405	High Similarity	NPC472991
0.9405	High Similarity	NPC472992
0.9401	High Similarity	NPC175230
0.9401	High Similarity	NPC88560
0.9401	High Similarity	NPC172033
0.9401	High Similarity	NPC472993
0.9398	High Similarity	NPC206123
0.9394	High Similarity	NPC127546
0.9394	High Similarity	NPC173637
0.9394	High Similarity	NPC317489
0.9394	High Similarity	NPC84362
0.9394	High Similarity	NPC52550
0.9394	High Similarity	NPC223424
0.939	High Similarity	NPC19388
0.939	High Similarity	NPC240431
0.939	High Similarity	NPC277205
0.939	High Similarity	NPC55786
0.9357	High Similarity	NPC223860
0.9357	High Similarity	NPC21359
0.9357	High Similarity	NPC275977
0.9357	High Similarity	NPC470717
0.9357	High Similarity	NPC25946
0.9357	High Similarity	NPC470720
0.9357	High Similarity	NPC249560
0.9357	High Similarity	NPC460984
0.9357	High Similarity	NPC470713
0.9345	High Similarity	NPC477848
0.9345	High Similarity	NPC264735
0.9341	High Similarity	NPC476772
0.9341	High Similarity	NPC47140
0.9341	High Similarity	NPC67134
0.9337	High Similarity	NPC225434
0.9337	High Similarity	NPC219904
0.9337	High Similarity	NPC120099
0.9337	High Similarity	NPC223747
0.9337	High Similarity	NPC203050
0.9333	High Similarity	NPC21100
0.9333	High Similarity	NPC197285
0.9333	High Similarity	NPC113968
0.9333	High Similarity	NPC277174
0.9333	High Similarity	NPC73855
0.9333	High Similarity	NPC328940
0.9333	High Similarity	NPC135599
0.9329	High Similarity	NPC168822
0.9302	High Similarity	NPC470719
0.9302	High Similarity	NPC104910
0.9302	High Similarity	NPC473554
0.9302	High Similarity	NPC474093
0.9302	High Similarity	NPC295625
0.9302	High Similarity	NPC33083
0.9298	High Similarity	NPC199172
0.9298	High Similarity	NPC35924
0.929	High Similarity	NPC211532
0.929	High Similarity	NPC471669
0.929	High Similarity	NPC89127
0.929	High Similarity	NPC233994
0.929	High Similarity	NPC268533
0.9286	High Similarity	NPC169977
0.9286	High Similarity	NPC45522
0.9286	High Similarity	NPC21666
0.9286	High Similarity	NPC42773
0.9286	High Similarity	NPC24043
0.9286	High Similarity	NPC101026
0.9281	High Similarity	NPC245014
0.9281	High Similarity	NPC254855
0.9281	High Similarity	NPC95866
0.9281	High Similarity	NPC136042
0.9281	High Similarity	NPC29958
0.9281	High Similarity	NPC156869
0.9281	High Similarity	NPC255157
0.9281	High Similarity	NPC67326
0.9281	High Similarity	NPC282987
0.9281	High Similarity	NPC84265
0.9281	High Similarity	NPC259896
0.9277	High Similarity	NPC325555
0.9277	High Similarity	NPC265530
0.9277	High Similarity	NPC160156
0.9277	High Similarity	NPC92565
0.9277	High Similarity	NPC116745
0.9277	High Similarity	NPC226304
0.9273	High Similarity	NPC205824
0.9273	High Similarity	NPC85751
0.9273	High Similarity	NPC129264
0.9273	High Similarity	NPC19240
0.9268	High Similarity	NPC189142
0.9268	High Similarity	NPC77660
0.9249	High Similarity	NPC30011
0.9249	High Similarity	NPC72554
0.9249	High Similarity	NPC475179
0.9249	High Similarity	NPC97817
0.924	High Similarity	NPC469371
0.924	High Similarity	NPC473073
0.924	High Similarity	NPC473071
0.924	High Similarity	NPC222674
0.9235	High Similarity	NPC476620
0.9235	High Similarity	NPC173837
0.9235	High Similarity	NPC476621
0.9235	High Similarity	NPC476623
0.9235	High Similarity	NPC476618
0.9235	High Similarity	NPC476619
0.9235	High Similarity	NPC476622
0.9226	High Similarity	NPC155877
0.9226	High Similarity	NPC33054
0.9226	High Similarity	NPC254540
0.9226	High Similarity	NPC172807
0.9226	High Similarity	NPC471748
0.9226	High Similarity	NPC476405
0.9226	High Similarity	NPC211594
0.9226	High Similarity	NPC203259
0.9226	High Similarity	NPC134532
0.9226	High Similarity	NPC60735
0.9226	High Similarity	NPC471725
0.9226	High Similarity	NPC117260
0.9226	High Similarity	NPC235575
0.9226	High Similarity	NPC26230
0.9226	High Similarity	NPC176740
0.9222	High Similarity	NPC52382
0.9222	High Similarity	NPC270578
0.9212	High Similarity	NPC80068
0.9212	High Similarity	NPC88043
0.9212	High Similarity	NPC191306
0.9212	High Similarity	NPC19709
0.9212	High Similarity	NPC270335
0.9207	High Similarity	NPC282169
0.9186	High Similarity	NPC470445
0.9186	High Similarity	NPC470449
0.9186	High Similarity	NPC470446
0.9186	High Similarity	NPC473072
0.9186	High Similarity	NPC107987
0.9186	High Similarity	NPC470447

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 NPC296018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	913
0.2-0.3	2045
0.3-0.4	2679
0.4-0.5	1814
0.5-0.6	886
0.6-0.7	278
0.7-0.8	120
0.8-0.85	16
0.85-0.9	19
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9461	High Similarity	NPD4338	Clinical (unspecified phase)
0.9394	High Similarity	NPD3818	Discontinued
0.9226	High Similarity	NPD6797	Phase 2
0.9172	High Similarity	NPD7251	Discontinued
0.9006	High Similarity	NPD7808	Phase 3
0.8994	High Similarity	NPD7054	Approved
0.8941	High Similarity	NPD7472	Approved
0.8909	High Similarity	NPD4381	Clinical (unspecified phase)
0.8848	High Similarity	NPD3882	Suspended
0.8848	High Similarity	NPD4868	Clinical (unspecified phase)
0.883	High Similarity	NPD7074	Phase 3
0.8817	High Similarity	NPD6168	Clinical (unspecified phase)
0.8817	High Similarity	NPD6167	Clinical (unspecified phase)
0.8817	High Similarity	NPD6166	Phase 2
0.8788	High Similarity	NPD3817	Phase 2
0.8675	High Similarity	NPD5402	Approved
0.8671	High Similarity	NPD7993	Clinical (unspecified phase)
0.8663	High Similarity	NPD7804	Clinical (unspecified phase)
0.8528	High Similarity	NPD1512	Approved
0.8514	High Similarity	NPD6559	Discontinued
0.8503	High Similarity	NPD2801	Approved
0.8476	Intermediate Similarity	NPD5403	Approved
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8443	Intermediate Similarity	NPD6801	Discontinued
0.8443	Intermediate Similarity	NPD1934	Approved
0.8405	Intermediate Similarity	NPD1511	Approved
0.8393	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD5401	Approved
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8293	Intermediate Similarity	NPD6799	Approved
0.8284	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD7199	Phase 2
0.8095	Intermediate Similarity	NPD1653	Approved
0.8079	Intermediate Similarity	NPD3751	Discontinued
0.8061	Intermediate Similarity	NPD6190	Approved
0.8059	Intermediate Similarity	NPD7411	Suspended
0.8057	Intermediate Similarity	NPD6232	Discontinued
0.8046	Intermediate Similarity	NPD5494	Approved
0.8034	Intermediate Similarity	NPD5844	Phase 1
0.8024	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8313	Approved
0.8011	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD7685	Pre-registration
0.7989	Intermediate Similarity	NPD6234	Discontinued
0.7989	Intermediate Similarity	NPD919	Approved
0.7978	Intermediate Similarity	NPD7228	Approved
0.7965	Intermediate Similarity	NPD1465	Phase 2
0.7955	Intermediate Similarity	NPD3787	Discontinued
0.7931	Intermediate Similarity	NPD3749	Approved
0.7917	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD37	Approved
0.7892	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1549	Phase 2
0.7874	Intermediate Similarity	NPD4967	Phase 2
0.7874	Intermediate Similarity	NPD4966	Approved
0.7874	Intermediate Similarity	NPD4965	Approved
0.7861	Intermediate Similarity	NPD7819	Suspended
0.7857	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD3926	Phase 2
0.7805	Intermediate Similarity	NPD1510	Phase 2
0.7797	Intermediate Similarity	NPD1247	Approved
0.7784	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7435	Discontinued
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2796	Approved
0.7737	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6959	Discontinued
0.7679	Intermediate Similarity	NPD3750	Approved
0.767	Intermediate Similarity	NPD7768	Phase 2
0.7665	Intermediate Similarity	NPD8151	Discontinued
0.7622	Intermediate Similarity	NPD230	Phase 1
0.7617	Intermediate Similarity	NPD6776	Approved
0.7617	Intermediate Similarity	NPD6781	Approved
0.7617	Intermediate Similarity	NPD6780	Approved
0.7617	Intermediate Similarity	NPD6782	Approved
0.7617	Intermediate Similarity	NPD6779	Approved
0.7617	Intermediate Similarity	NPD6778	Approved
0.7617	Intermediate Similarity	NPD6777	Approved
0.7605	Intermediate Similarity	NPD7266	Discontinued
0.7561	Intermediate Similarity	NPD943	Approved
0.756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8455	Phase 2
0.7545	Intermediate Similarity	NPD1551	Phase 2
0.7538	Intermediate Similarity	NPD7874	Approved
0.7538	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7240	Approved
0.7514	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD2533	Approved
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7462	Intermediate Similarity	NPD7870	Phase 2
0.7462	Intermediate Similarity	NPD7871	Phase 2
0.7455	Intermediate Similarity	NPD1613	Approved
0.7455	Intermediate Similarity	NPD1240	Approved
0.7455	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7783	Phase 2
0.7413	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7698	Approved
0.7411	Intermediate Similarity	NPD7697	Approved
0.7411	Intermediate Similarity	NPD7696	Phase 3
0.741	Intermediate Similarity	NPD1933	Approved
0.741	Intermediate Similarity	NPD447	Suspended
0.7399	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7584	Approved
0.7384	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3748	Approved
0.7374	Intermediate Similarity	NPD8320	Phase 1
0.7374	Intermediate Similarity	NPD8319	Approved
0.7365	Intermediate Similarity	NPD1607	Approved
0.7358	Intermediate Similarity	NPD6535	Approved
0.7358	Intermediate Similarity	NPD6534	Approved
0.735	Intermediate Similarity	NPD7701	Phase 2
0.7337	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.733	Intermediate Similarity	NPD3226	Approved
0.7316	Intermediate Similarity	NPD8150	Discontinued
0.731	Intermediate Similarity	NPD1243	Approved
0.7289	Intermediate Similarity	NPD6233	Phase 2
0.7283	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5953	Discontinued
0.726	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7700	Phase 2
0.7245	Intermediate Similarity	NPD7699	Phase 2
0.7241	Intermediate Similarity	NPD7801	Approved
0.7236	Intermediate Similarity	NPD7680	Approved
0.7232	Intermediate Similarity	NPD7458	Discontinued
0.7229	Intermediate Similarity	NPD2313	Discontinued
0.7212	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2800	Approved
0.7208	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2344	Approved
0.719	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6823	Phase 2
0.7178	Intermediate Similarity	NPD7585	Approved
0.7176	Intermediate Similarity	NPD7033	Discontinued
0.7169	Intermediate Similarity	NPD3027	Phase 3
0.7166	Intermediate Similarity	NPD7286	Phase 2
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1203	Approved
0.7129	Intermediate Similarity	NPD7583	Approved
0.7108	Intermediate Similarity	NPD6832	Phase 2
0.7105	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD7229	Phase 3
0.7076	Intermediate Similarity	NPD2799	Discontinued
0.7062	Intermediate Similarity	NPD4287	Approved
0.7055	Intermediate Similarity	NPD9269	Phase 2
0.7031	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2309	Approved
0.7027	Intermediate Similarity	NPD8127	Discontinued
0.7024	Intermediate Similarity	NPD3764	Approved
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2346	Discontinued
0.6989	Remote Similarity	NPD5711	Approved
0.6989	Remote Similarity	NPD5710	Approved
0.6963	Remote Similarity	NPD7038	Approved
0.6963	Remote Similarity	NPD7039	Approved
0.6954	Remote Similarity	NPD6213	Phase 3
0.6954	Remote Similarity	NPD6212	Phase 3
0.6954	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5242	Approved
0.6949	Remote Similarity	NPD7390	Discontinued
0.6946	Remote Similarity	NPD9494	Approved
0.694	Remote Similarity	NPD5353	Approved
0.6931	Remote Similarity	NPD7799	Discontinued
0.6931	Remote Similarity	NPD5005	Approved
0.6931	Remote Similarity	NPD2163	Approved
0.6931	Remote Similarity	NPD5006	Approved
0.6923	Remote Similarity	NPD6844	Discontinued
0.6915	Remote Similarity	NPD2403	Approved
0.6914	Remote Similarity	NPD1652	Phase 2
0.691	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4908	Phase 1
0.689	Remote Similarity	NPD1091	Approved
0.689	Remote Similarity	NPD7930	Approved
0.6886	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6273	Approved
0.6868	Remote Similarity	NPD6386	Approved
0.6868	Remote Similarity	NPD6385	Approved
0.6867	Remote Similarity	NPD3225	Approved
0.6865	Remote Similarity	NPD6971	Discontinued

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