NPASS Compound

Structure

CID211532 OpenBabel06191716002D 41 44 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -6.9282 2.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 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 -1.7321 -0.0000 0.0000 C 0 0 2 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 37 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 38 1 0 0 0 0 11 25 1 0 0 0 0 12 13 2 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 18 1 0 0 0 0 14 39 1 0 0 0 0 15 26 2 0 0 0 0 15 40 1 0 0 0 0 16 9 1 6 0 0 0 16 19 1 0 0 0 0 16 41 1 0 0 0 0 17 30 2 0 0 0 0 17 38 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 19 22 1 0 0 0 0 19 31 1 1 0 0 0 20 23 1 0 0 0 0 20 32 2 0 0 0 0 21 26 1 0 0 0 0 21 33 1 0 0 0 0 22 24 1 0 0 0 0 22 34 1 6 0 0 0 23 25 2 0 0 0 0 23 35 1 0 0 0 0 24 27 1 0 0 0 0 24 36 1 1 0 0 0 25 39 1 0 0 0 0 26 37 1 0 0 0 0 27 40 1 6 0 0 0 27 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.16
Volume:	540.657
LogP:	2.395
LogD:	1.25
LogS:	-4.41
# Rotatable Bonds:	9
TPSA:	225.81
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.147
Synthetic Accessibility Score:	4.288
Fsp3:	0.407
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.988
MDCK Permeability:	2.159287760150619e-05
Pgp-inhibitor:	0.217
Pgp-substrate:	0.709
Human Intestinal Absorption (HIA):	0.284
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.834

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	90.60099029541016%
Volume Distribution (VD):	0.703
Pgp-substrate:	13.26782512664795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.287
CYP2D6-inhibitor:	0.24
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.139
CYP3A4-substrate:	0.029

ADMET: Excretion

Clearance (CL):	5.142
Half-life (T1/2):	0.92

ADMET: Toxicity

hERG Blockers:	0.394
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.811
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.641
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.716
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC211532

Natural Product ID:	NPC211532
*Common Name:**	Patuletin 7-O-(6''-Isovaleryl)Glucoside
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6-methoxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-methylbutanoate
Synonyms:
Standard InCHIKey:	SOEZANHKTWLRIX-BAHLFPRBSA-N
Standard InCHI:	InChI=1S/C27H30O14/c1-10(2)6-17(30)38-9-16-19(31)22(34)24(36)27(41-16)40-15-8-14-18(21(33)26(15)37-3)20(32)23(35)25(39-14)11-4-5-12(28)13(29)7-11/h4-5,7-8,10,16,19,22,24,27-29,31,33-36H,6,9H2,1-3H3/t16-,19-,22+,24-,27-/m1/s1
SMILES:	CC(C)CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc3c(c(=O)c(c(c4ccc(c(c4)O)O)o3)O)c(c2OC)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474868
PubChem CID:	10370955
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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
NPO40994	Inula britannica	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[10650074]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643020]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17782	Inula britannica	Species	Asteraceae	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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11.7	ug.mL-1	PMID[554296]
NPT1	Others	Radical scavenging activity		IC50	=	14.3	ug.mL-1	PMID[554296]

☑ 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 NPC211532 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	413
0.1-0.2	1722
0.2-0.3	3891
0.3-0.4	8817
0.4-0.5	9180
0.5-0.6	4593
0.6-0.7	5113
0.7-0.8	5540
0.8-0.85	1729
0.85-0.9	1159
0.9-0.95	388
0.95-1	152

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233994
0.9939	High Similarity	NPC477848
0.9878	High Similarity	NPC472385
0.9878	High Similarity	NPC198324
0.9817	High Similarity	NPC43211
0.9817	High Similarity	NPC49344
0.9817	High Similarity	NPC264735
0.9817	High Similarity	NPC101191
0.9817	High Similarity	NPC210094
0.9817	High Similarity	NPC115760
0.9817	High Similarity	NPC237435
0.9817	High Similarity	NPC135277
0.9816	High Similarity	NPC211594
0.9816	High Similarity	NPC172807
0.9816	High Similarity	NPC476405
0.9816	High Similarity	NPC254540
0.9816	High Similarity	NPC117260
0.9756	High Similarity	NPC45522
0.9756	High Similarity	NPC169977
0.9756	High Similarity	NPC4390
0.9756	High Similarity	NPC21666
0.9756	High Similarity	NPC42773
0.9756	High Similarity	NPC24043
0.9756	High Similarity	NPC101026
0.9755	High Similarity	NPC84265
0.9755	High Similarity	NPC245014
0.9755	High Similarity	NPC282987
0.9695	High Similarity	NPC175107
0.9695	High Similarity	NPC153755
0.9695	High Similarity	NPC190003
0.9693	High Similarity	NPC201292
0.9693	High Similarity	NPC475942
0.9693	High Similarity	NPC469931
0.9693	High Similarity	NPC186807
0.9693	High Similarity	NPC45638
0.9693	High Similarity	NPC93337
0.9693	High Similarity	NPC226294
0.9693	High Similarity	NPC105025
0.9693	High Similarity	NPC58053
0.9643	High Similarity	NPC470447
0.9643	High Similarity	NPC470445
0.9643	High Similarity	NPC36138
0.9643	High Similarity	NPC470446
0.9643	High Similarity	NPC470449
0.9639	High Similarity	NPC472384
0.9639	High Similarity	NPC268533
0.9639	High Similarity	NPC472382
0.9639	High Similarity	NPC472380
0.9639	High Similarity	NPC169733
0.9634	High Similarity	NPC244776
0.9634	High Similarity	NPC116864
0.9634	High Similarity	NPC155763
0.9634	High Similarity	NPC235260
0.9634	High Similarity	NPC20505
0.9632	High Similarity	NPC58716
0.9632	High Similarity	NPC45618
0.9632	High Similarity	NPC146792
0.9586	High Similarity	NPC470451
0.9586	High Similarity	NPC470416
0.9586	High Similarity	NPC470455
0.9583	High Similarity	NPC222674
0.9581	High Similarity	NPC168584
0.9576	High Similarity	NPC205076
0.9576	High Similarity	NPC307518
0.9576	High Similarity	NPC48773
0.9576	High Similarity	NPC472386
0.9573	High Similarity	NPC138927
0.9573	High Similarity	NPC120099
0.9573	High Similarity	NPC225434
0.9573	High Similarity	NPC219904
0.9573	High Similarity	NPC203050
0.9573	High Similarity	NPC223747
0.9571	High Similarity	NPC197285
0.9571	High Similarity	NPC21100
0.9527	High Similarity	NPC107987
0.9524	High Similarity	NPC110941
0.9524	High Similarity	NPC241423
0.9524	High Similarity	NPC473682
0.9524	High Similarity	NPC126784
0.9524	High Similarity	NPC473571
0.9524	High Similarity	NPC470444
0.9524	High Similarity	NPC470443
0.9521	High Similarity	NPC8573
0.9521	High Similarity	NPC470949
0.9521	High Similarity	NPC472991
0.9521	High Similarity	NPC472992
0.9521	High Similarity	NPC65563
0.9518	High Similarity	NPC204693
0.9515	High Similarity	NPC21190
0.9515	High Similarity	NPC105511
0.9515	High Similarity	NPC224462
0.9515	High Similarity	NPC22195
0.9515	High Similarity	NPC206123
0.9515	High Similarity	NPC183357
0.9512	High Similarity	NPC127546
0.9512	High Similarity	NPC116745
0.9512	High Similarity	NPC173637
0.9512	High Similarity	NPC265530
0.9512	High Similarity	NPC325555
0.9512	High Similarity	NPC84362
0.9512	High Similarity	NPC223424
0.9512	High Similarity	NPC52550
0.9512	High Similarity	NPC226304
0.9512	High Similarity	NPC317489
0.9509	High Similarity	NPC22832
0.9509	High Similarity	NPC277205
0.9509	High Similarity	NPC311830
0.9467	High Similarity	NPC473071
0.9467	High Similarity	NPC473073
0.9464	High Similarity	NPC173837
0.9464	High Similarity	NPC139571
0.9464	High Similarity	NPC217520
0.9464	High Similarity	NPC35167
0.9461	High Similarity	NPC253685
0.9458	High Similarity	NPC3583
0.9458	High Similarity	NPC259152
0.9455	High Similarity	NPC471457
0.9455	High Similarity	NPC472381
0.9455	High Similarity	NPC210042
0.9455	High Similarity	NPC95855
0.9455	High Similarity	NPC170675
0.9455	High Similarity	NPC472383
0.9455	High Similarity	NPC112755
0.9451	High Similarity	NPC274618
0.9451	High Similarity	NPC253662
0.9451	High Similarity	NPC308404
0.9451	High Similarity	NPC277174
0.9451	High Similarity	NPC113968
0.9451	High Similarity	NPC73855
0.9451	High Similarity	NPC88789
0.9451	High Similarity	NPC135599
0.9451	High Similarity	NPC99957
0.9451	High Similarity	NPC181616
0.9451	High Similarity	NPC118284
0.9451	High Similarity	NPC145038
0.9451	High Similarity	NPC179950
0.9451	High Similarity	NPC281131
0.9451	High Similarity	NPC328940
0.9451	High Similarity	NPC56077
0.9451	High Similarity	NPC276222
0.9448	High Similarity	NPC191306
0.9448	High Similarity	NPC270335
0.9448	High Similarity	NPC222936
0.9448	High Similarity	NPC94777
0.9448	High Similarity	NPC88023
0.9448	High Similarity	NPC243930
0.9448	High Similarity	NPC284960
0.9448	High Similarity	NPC19709
0.9448	High Similarity	NPC309025
0.9412	High Similarity	NPC473072
0.9405	High Similarity	NPC61904
0.9405	High Similarity	NPC144097
0.9405	High Similarity	NPC471669
0.9405	High Similarity	NPC89127
0.9401	High Similarity	NPC239549
0.9401	High Similarity	NPC175230
0.9401	High Similarity	NPC236191
0.9401	High Similarity	NPC88560
0.9401	High Similarity	NPC172033
0.9401	High Similarity	NPC472993
0.9401	High Similarity	NPC51774
0.9398	High Similarity	NPC285197
0.9398	High Similarity	NPC34287
0.9398	High Similarity	NPC95866
0.9398	High Similarity	NPC149011
0.9398	High Similarity	NPC44558
0.9398	High Similarity	NPC474434
0.9398	High Similarity	NPC471416
0.9398	High Similarity	NPC204937
0.9398	High Similarity	NPC67105
0.9394	High Similarity	NPC229729
0.9394	High Similarity	NPC93099
0.9394	High Similarity	NPC135345
0.939	High Similarity	NPC55786
0.939	High Similarity	NPC19388
0.939	High Similarity	NPC240431
0.9387	High Similarity	NPC473043
0.9387	High Similarity	NPC77660
0.9387	High Similarity	NPC189142
0.9357	High Similarity	NPC148710
0.9349	High Similarity	NPC476619
0.9349	High Similarity	NPC267680
0.9349	High Similarity	NPC476622
0.9349	High Similarity	NPC113836
0.9349	High Similarity	NPC476618
0.9349	High Similarity	NPC217387
0.9349	High Similarity	NPC476623
0.9349	High Similarity	NPC37668
0.9349	High Similarity	NPC477895
0.9349	High Similarity	NPC476620
0.9349	High Similarity	NPC253521
0.9349	High Similarity	NPC196127
0.9349	High Similarity	NPC258044
0.9349	High Similarity	NPC472387
0.9349	High Similarity	NPC293626
0.9349	High Similarity	NPC476621
0.9345	High Similarity	NPC472607
0.9345	High Similarity	NPC81042
0.9345	High Similarity	NPC473327
0.9345	High Similarity	NPC476472

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 NPC211532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	939
0.2-0.3	1976
0.3-0.4	2612
0.4-0.5	1859
0.5-0.6	904
0.6-0.7	315
0.7-0.8	130
0.8-0.85	26
0.85-0.9	13
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9817	High Similarity	NPD4338	Clinical (unspecified phase)
0.9341	High Similarity	NPD6797	Phase 2
0.9337	High Similarity	NPD7054	Approved
0.9286	High Similarity	NPD7251	Discontinued
0.9281	High Similarity	NPD7472	Approved
0.9231	High Similarity	NPD7808	Phase 3
0.9167	High Similarity	NPD7074	Phase 3
0.9162	High Similarity	NPD3818	Discontinued
0.8957	High Similarity	NPD2801	Approved
0.8929	High Similarity	NPD6167	Clinical (unspecified phase)
0.8929	High Similarity	NPD6166	Phase 2
0.8929	High Similarity	NPD6168	Clinical (unspecified phase)
0.8909	High Similarity	NPD4381	Clinical (unspecified phase)
0.8902	High Similarity	NPD3817	Phase 2
0.878	High Similarity	NPD1934	Approved
0.8772	High Similarity	NPD7804	Clinical (unspecified phase)
0.8675	High Similarity	NPD5402	Approved
0.8623	High Similarity	NPD4868	Clinical (unspecified phase)
0.8623	High Similarity	NPD3882	Suspended
0.8614	High Similarity	NPD2393	Clinical (unspecified phase)
0.8528	High Similarity	NPD1512	Approved
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8457	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD1653	Approved
0.8405	Intermediate Similarity	NPD1511	Approved
0.8363	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8305	Intermediate Similarity	NPD6559	Discontinued
0.8297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5403	Approved
0.8239	Intermediate Similarity	NPD5844	Phase 1
0.8202	Intermediate Similarity	NPD7685	Pre-registration
0.8182	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5401	Approved
0.8125	Intermediate Similarity	NPD7473	Discontinued
0.8122	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7228	Approved
0.807	Intermediate Similarity	NPD1465	Phase 2
0.8057	Intermediate Similarity	NPD6232	Discontinued
0.8011	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7989	Intermediate Similarity	NPD6234	Discontinued
0.7989	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD3751	Discontinued
0.7965	Intermediate Similarity	NPD7819	Suspended
0.7955	Intermediate Similarity	NPD3787	Discontinued
0.7953	Intermediate Similarity	NPD7411	Suspended
0.7929	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD8312	Approved
0.7912	Intermediate Similarity	NPD8313	Approved
0.7907	Intermediate Similarity	NPD37	Approved
0.7895	Intermediate Similarity	NPD6599	Discontinued
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
0.7865	Intermediate Similarity	NPD7435	Discontinued
0.7844	Intermediate Similarity	NPD6190	Approved
0.7801	Intermediate Similarity	NPD6781	Approved
0.7801	Intermediate Similarity	NPD6782	Approved
0.7801	Intermediate Similarity	NPD6778	Approved
0.7801	Intermediate Similarity	NPD6777	Approved
0.7801	Intermediate Similarity	NPD6779	Approved
0.7801	Intermediate Similarity	NPD6780	Approved
0.7801	Intermediate Similarity	NPD6776	Approved
0.7797	Intermediate Similarity	NPD1247	Approved
0.7784	Intermediate Similarity	NPD919	Approved
0.7784	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2796	Approved
0.7711	Intermediate Similarity	NPD7266	Discontinued
0.7706	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6959	Discontinued
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7667	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7874	Approved
0.7626	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD230	Phase 1
0.7622	Intermediate Similarity	NPD1933	Approved
0.7611	Intermediate Similarity	NPD3926	Phase 2
0.7609	Intermediate Similarity	NPD7240	Approved
0.759	Intermediate Similarity	NPD7696	Phase 3
0.759	Intermediate Similarity	NPD7698	Approved
0.759	Intermediate Similarity	NPD7697	Approved
0.7588	Intermediate Similarity	NPD7783	Phase 2
0.7588	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD8151	Discontinued
0.7574	Intermediate Similarity	NPD3750	Approved
0.7561	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1613	Approved
0.7551	Intermediate Similarity	NPD7871	Phase 2
0.7551	Intermediate Similarity	NPD7870	Phase 2
0.7545	Intermediate Similarity	NPD2935	Discontinued
0.7539	Intermediate Similarity	NPD6534	Approved
0.7539	Intermediate Similarity	NPD6535	Approved
0.7528	Intermediate Similarity	NPD3749	Approved
0.7525	Intermediate Similarity	NPD7701	Phase 2
0.7515	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7475	Intermediate Similarity	NPD7584	Approved
0.7472	Intermediate Similarity	NPD7768	Phase 2
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7461	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD1240	Approved
0.7455	Intermediate Similarity	NPD943	Approved
0.744	Intermediate Similarity	NPD1551	Phase 2
0.7439	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7699	Phase 2
0.7423	Intermediate Similarity	NPD7700	Phase 2
0.7399	Intermediate Similarity	NPD2533	Approved
0.7399	Intermediate Similarity	NPD2532	Approved
0.7399	Intermediate Similarity	NPD2534	Approved
0.7378	Intermediate Similarity	NPD3027	Phase 3
0.7374	Intermediate Similarity	NPD8320	Phase 1
0.7374	Intermediate Similarity	NPD8319	Approved
0.7365	Intermediate Similarity	NPD1607	Approved
0.736	Intermediate Similarity	NPD6823	Phase 2
0.7317	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD920	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6233	Phase 2
0.7278	Intermediate Similarity	NPD3748	Approved
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5953	Discontinued
0.7264	Intermediate Similarity	NPD7585	Approved
0.726	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7680	Approved
0.7232	Intermediate Similarity	NPD3226	Approved
0.7232	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD5353	Approved
0.7214	Intermediate Similarity	NPD7583	Approved
0.7207	Intermediate Similarity	NPD6844	Discontinued
0.72	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2799	Discontinued
0.7176	Intermediate Similarity	NPD7033	Discontinued
0.7172	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7286	Phase 2
0.7128	Intermediate Similarity	NPD6213	Phase 3
0.7128	Intermediate Similarity	NPD6212	Phase 3
0.7128	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2313	Discontinued
0.7126	Intermediate Similarity	NPD6798	Discontinued
0.711	Intermediate Similarity	NPD1243	Approved
0.711	Intermediate Similarity	NPD6674	Discontinued
0.711	Intermediate Similarity	NPD1652	Phase 2
0.711	Intermediate Similarity	NPD2800	Approved
0.7108	Intermediate Similarity	NPD6832	Phase 2
0.7105	Intermediate Similarity	NPD7549	Discontinued
0.7105	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD5124	Phase 1
0.7101	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2346	Discontinued
0.7092	Intermediate Similarity	NPD4360	Phase 2
0.7092	Intermediate Similarity	NPD4363	Phase 3
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD9494	Approved
0.7043	Intermediate Similarity	NPD5242	Approved
0.7039	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6100	Approved
0.7035	Intermediate Similarity	NPD6099	Approved
0.7031	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1203	Approved
0.7027	Intermediate Similarity	NPD8127	Discontinued
0.7024	Intermediate Similarity	NPD3268	Approved
0.7015	Intermediate Similarity	NPD5005	Approved
0.7015	Intermediate Similarity	NPD5006	Approved
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1091	Approved
0.6989	Remote Similarity	NPD5711	Approved
0.6989	Remote Similarity	NPD5710	Approved
0.6988	Remote Similarity	NPD2798	Approved
0.6971	Remote Similarity	NPD7930	Approved
0.6961	Remote Similarity	NPD6386	Approved
0.6961	Remote Similarity	NPD6385	Approved
0.6959	Remote Similarity	NPD6651	Approved
0.6951	Remote Similarity	NPD9269	Phase 2
0.6941	Remote Similarity	NPD4060	Phase 1
0.6928	Remote Similarity	NPD2797	Approved
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7097	Phase 1

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