NPASS Compound

Structure

CID181250 OpenBabel06191715552D 31 33 0 0 0 0 0 0 0 0999 V2000 3.4641 -5.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 3.4641 1.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 5.1962 -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 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 31 1 0 0 0 0 13 19 2 0 0 0 0 13 24 1 0 0 0 0 14 19 1 0 0 0 0 14 25 1 0 0 0 0 15 20 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 17 23 2 0 0 0 0 18 22 2 0 0 0 0 18 31 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.14
Volume:	421.419
LogP:	2.835
LogD:	2.746
LogS:	-4.096
# Rotatable Bonds:	8
TPSA:	94.82
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	2.472
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.582
MDCK Permeability:	2.5837955035967752e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	65.50538635253906%
Volume Distribution (VD):	0.89
Pgp-substrate:	44.105716705322266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.271
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.342
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.574
CYP3A4-substrate:	0.866

ADMET: Excretion

Clearance (CL):	4.459
Half-life (T1/2):	0.523

ADMET: Toxicity

hERG Blockers:	0.359
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.177
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.102
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC181250

Natural Product ID:	NPC181250
*Common Name:**	3,5,6,7,3',4',5'-Heptamethoxyflavone
IUPAC Name:	3,5,6,7-tetramethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	SHRSLVWLFNSTLK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H24O9/c1-24-13-8-11(9-14(25-2)19(13)27-4)18-22(30-7)17(23)16-12(31-18)10-15(26-3)20(28-5)21(16)29-6/h8-10H,1-7H3
SMILES:	COc1c(OC)cc(cc1OC)c1oc2cc(OC)c(c(c2c(=O)c1OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109440
PubChem CID:	389001
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO33509	byrsonima coccolobifolia	Species	Malpighiaceae	Eukaryota	leaves and stems	cerrado at the Federal University of So Carlos (UFSCar), So Carlos, SP, Brazil	2011-Jul	PMID[24521209]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715.1	Murraya paniculata var. exotica	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715.1	Murraya paniculata var. exotica	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2715	Murraya paniculata	Species	Rutaceae	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	4
Others	7

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1662	Individual Protein	Arginase	Leishmania amazonensis	IC50	=	127900.0	nM	PMID[483551]
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	81.2	%	PMID[483552]
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	93.8	%	PMID[483552]
NPT319	Cell Line	B16	Mus musculus	IC50	>	100000.0	nM	PMID[483552]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	>	100.0	uM	PMID[483552]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	31610.0	nM	PMID[483552]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	GI	=	35.0	%	PMID[483552]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	5800.0	nM	PMID[483552]
NPT2229	Organism	Trypanosoma brucei gambiense	Trypanosoma brucei gambiense	GI	=	72.4	%	PMID[483552]
NPT2229	Organism	Trypanosoma brucei gambiense	Trypanosoma brucei gambiense	GI	=	25.9	%	PMID[483552]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC90	=	10800.0	nM	PMID[483552]

☑ 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 NPC181250 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	529
0.1-0.2	2147
0.2-0.3	5579
0.3-0.4	11688
0.4-0.5	5352
0.5-0.6	4258
0.6-0.7	5618
0.7-0.8	4662
0.8-0.85	1690
0.85-0.9	822
0.9-0.95	307
0.95-1	45

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC201547
0.993	High Similarity	NPC259058
0.986	High Similarity	NPC69752
0.9789	High Similarity	NPC302408
0.9789	High Similarity	NPC283002
0.972	High Similarity	NPC85233
0.9718	High Similarity	NPC165512
0.966	High Similarity	NPC276059
0.966	High Similarity	NPC34725
0.966	High Similarity	NPC241774
0.966	High Similarity	NPC122623
0.9658	High Similarity	NPC134677
0.965	High Similarity	NPC215932
0.965	High Similarity	NPC40818
0.965	High Similarity	NPC310259
0.965	High Similarity	NPC110639
0.965	High Similarity	NPC106461
0.965	High Similarity	NPC14958
0.9595	High Similarity	NPC178854
0.9595	High Similarity	NPC257277
0.9592	High Similarity	NPC246204
0.9583	High Similarity	NPC299923
0.9583	High Similarity	NPC205522
0.953	High Similarity	NPC78302
0.953	High Similarity	NPC235215
0.953	High Similarity	NPC7973
0.953	High Similarity	NPC472438
0.953	High Similarity	NPC29841
0.9527	High Similarity	NPC189960
0.9527	High Similarity	NPC32557
0.951	High Similarity	NPC23955
0.9507	High Similarity	NPC29536
0.9467	High Similarity	NPC7846
0.9467	High Similarity	NPC300943
0.9467	High Similarity	NPC191459
0.9467	High Similarity	NPC288669
0.9467	High Similarity	NPC4481
0.9467	High Similarity	NPC176300
0.9467	High Similarity	NPC253634
0.9467	High Similarity	NPC25495
0.9467	High Similarity	NPC9609
0.9467	High Similarity	NPC261004
0.9467	High Similarity	NPC19687
0.9467	High Similarity	NPC18772
0.9467	High Similarity	NPC115798
0.9467	High Similarity	NPC104459
0.9467	High Similarity	NPC143828
0.9467	High Similarity	NPC152166
0.9467	High Similarity	NPC204854
0.9467	High Similarity	NPC257914
0.9467	High Similarity	NPC18607
0.9467	High Similarity	NPC22472
0.9467	High Similarity	NPC105242
0.9467	High Similarity	NPC238405
0.9467	High Similarity	NPC130894
0.9463	High Similarity	NPC200388
0.9463	High Similarity	NPC474520
0.9463	High Similarity	NPC100916
0.9463	High Similarity	NPC55619
0.9463	High Similarity	NPC268161
0.9459	High Similarity	NPC86485
0.9459	High Similarity	NPC476289
0.9456	High Similarity	NPC76376
0.9456	High Similarity	NPC472535
0.9456	High Similarity	NPC474170
0.9456	High Similarity	NPC474388
0.9444	High Similarity	NPC136278
0.9441	High Similarity	NPC70853
0.9441	High Similarity	NPC9966
0.94	High Similarity	NPC110070
0.94	High Similarity	NPC224137
0.94	High Similarity	NPC176665
0.94	High Similarity	NPC305663
0.94	High Similarity	NPC75215
0.94	High Similarity	NPC287979
0.94	High Similarity	NPC203891
0.94	High Similarity	NPC163524
0.94	High Similarity	NPC227192
0.94	High Similarity	NPC189179
0.94	High Similarity	NPC101830
0.94	High Similarity	NPC93376
0.9392	High Similarity	NPC301123
0.9388	High Similarity	NPC219330
0.9388	High Similarity	NPC177839
0.9384	High Similarity	NPC10304
0.9384	High Similarity	NPC63256
0.9384	High Similarity	NPC261548
0.9375	High Similarity	NPC113089
0.9371	High Similarity	NPC214919
0.9371	High Similarity	NPC124467
0.9338	High Similarity	NPC193842
0.9333	High Similarity	NPC245546
0.9333	High Similarity	NPC98661
0.9333	High Similarity	NPC247017
0.9333	High Similarity	NPC49824
0.9333	High Similarity	NPC43243
0.9333	High Similarity	NPC266960
0.9333	High Similarity	NPC292107
0.9329	High Similarity	NPC58382
0.9329	High Similarity	NPC75279
0.9329	High Similarity	NPC162351
0.9329	High Similarity	NPC276409
0.9329	High Similarity	NPC250822
0.9324	High Similarity	NPC236769
0.9324	High Similarity	NPC226973
0.9324	High Similarity	NPC208043
0.932	High Similarity	NPC238366
0.932	High Similarity	NPC328119
0.9315	High Similarity	NPC117463
0.9276	High Similarity	NPC131557
0.9276	High Similarity	NPC246478
0.9267	High Similarity	NPC196439
0.9267	High Similarity	NPC4455
0.9267	High Similarity	NPC2476
0.9267	High Similarity	NPC138360
0.9267	High Similarity	NPC280339
0.9267	High Similarity	NPC201136
0.9267	High Similarity	NPC208197
0.9267	High Similarity	NPC201451
0.9267	High Similarity	NPC44079
0.9267	High Similarity	NPC146165
0.9267	High Similarity	NPC227325
0.9267	High Similarity	NPC92659
0.9267	High Similarity	NPC183597
0.9267	High Similarity	NPC128863
0.9267	High Similarity	NPC167815
0.9267	High Similarity	NPC214138
0.9267	High Similarity	NPC26227
0.9267	High Similarity	NPC163780
0.9267	High Similarity	NPC50715
0.9262	High Similarity	NPC123886
0.9257	High Similarity	NPC50728
0.9257	High Similarity	NPC166753
0.9257	High Similarity	NPC306821
0.9247	High Similarity	NPC216314
0.9247	High Similarity	NPC120924
0.9247	High Similarity	NPC195919
0.9247	High Similarity	NPC231013
0.9241	High Similarity	NPC182842
0.9221	High Similarity	NPC470459
0.9205	High Similarity	NPC265511
0.9205	High Similarity	NPC303255
0.92	High Similarity	NPC280937
0.92	High Similarity	NPC160951
0.92	High Similarity	NPC231018
0.92	High Similarity	NPC274327
0.92	High Similarity	NPC472408
0.92	High Similarity	NPC270620
0.92	High Similarity	NPC183878
0.92	High Similarity	NPC145379
0.92	High Similarity	NPC179126
0.92	High Similarity	NPC255350
0.92	High Similarity	NPC176775
0.92	High Similarity	NPC69394
0.92	High Similarity	NPC473664
0.92	High Similarity	NPC78326
0.92	High Similarity	NPC186507
0.92	High Similarity	NPC236223
0.92	High Similarity	NPC47781
0.92	High Similarity	NPC22519
0.9195	High Similarity	NPC133953
0.9195	High Similarity	NPC308451
0.9195	High Similarity	NPC28274
0.9195	High Similarity	NPC474663
0.9195	High Similarity	NPC50403
0.9189	High Similarity	NPC159103
0.9184	High Similarity	NPC62536
0.9184	High Similarity	NPC33265
0.9178	High Similarity	NPC471590
0.9167	High Similarity	NPC58229
0.9161	High Similarity	NPC470457
0.9161	High Similarity	NPC280893
0.9139	High Similarity	NPC471746
0.9139	High Similarity	NPC213622
0.9139	High Similarity	NPC20830
0.9139	High Similarity	NPC256612
0.9139	High Similarity	NPC284353
0.9133	High Similarity	NPC162313
0.9133	High Similarity	NPC239128
0.9133	High Similarity	NPC293183
0.9133	High Similarity	NPC166201
0.9133	High Similarity	NPC188203
0.9133	High Similarity	NPC241498
0.9133	High Similarity	NPC83508
0.9133	High Similarity	NPC156222
0.9133	High Similarity	NPC301323
0.9133	High Similarity	NPC279989
0.9133	High Similarity	NPC275836
0.9133	High Similarity	NPC198826
0.9133	High Similarity	NPC275722
0.9133	High Similarity	NPC82325
0.9133	High Similarity	NPC57030
0.9133	High Similarity	NPC222830
0.9133	High Similarity	NPC212678
0.9133	High Similarity	NPC100887
0.9133	High Similarity	NPC292460
0.9133	High Similarity	NPC256283
0.9133	High Similarity	NPC142540
0.9133	High Similarity	NPC120163
0.9133	High Similarity	NPC131624

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 NPC181250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	460
0.1-0.2	1045
0.2-0.3	1921
0.3-0.4	2737
0.4-0.5	1660
0.5-0.6	873
0.6-0.7	316
0.7-0.8	97
0.8-0.85	26
0.85-0.9	12
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9267	High Similarity	NPD3817	Phase 2
0.92	High Similarity	NPD2801	Approved
0.8831	High Similarity	NPD3882	Suspended
0.8782	High Similarity	NPD5494	Approved
0.8733	High Similarity	NPD1512	Approved
0.8726	High Similarity	NPD1247	Approved
0.865	High Similarity	NPD4338	Clinical (unspecified phase)
0.8636	High Similarity	NPD1934	Approved
0.86	High Similarity	NPD1511	Approved
0.8562	High Similarity	NPD6168	Clinical (unspecified phase)
0.8562	High Similarity	NPD6167	Clinical (unspecified phase)
0.8562	High Similarity	NPD6166	Phase 2
0.8543	High Similarity	NPD4378	Clinical (unspecified phase)
0.8526	High Similarity	NPD5402	Approved
0.8503	High Similarity	NPD2796	Approved
0.85	High Similarity	NPD3926	Phase 2
0.8477	Intermediate Similarity	NPD6799	Approved
0.8462	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7808	Phase 3
0.8415	Intermediate Similarity	NPD6797	Phase 2
0.8365	Intermediate Similarity	NPD919	Approved
0.8364	Intermediate Similarity	NPD7251	Discontinued
0.8344	Intermediate Similarity	NPD3818	Discontinued
0.8293	Intermediate Similarity	NPD7054	Approved
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8242	Intermediate Similarity	NPD7472	Approved
0.8228	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8077	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD5403	Approved
0.8065	Intermediate Similarity	NPD5401	Approved
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8038	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD7819	Suspended
0.7964	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1510	Phase 2
0.7908	Intermediate Similarity	NPD1549	Phase 2
0.787	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.78	Intermediate Similarity	NPD1240	Approved
0.7792	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.7764	Intermediate Similarity	NPD7411	Suspended
0.7748	Intermediate Similarity	NPD1933	Approved
0.7742	Intermediate Similarity	NPD1243	Approved
0.7736	Intermediate Similarity	NPD920	Approved
0.773	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3748	Approved
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7697	Intermediate Similarity	NPD1607	Approved
0.7679	Intermediate Similarity	NPD2403	Approved
0.7632	Intermediate Similarity	NPD447	Suspended
0.7619	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD943	Approved
0.756	Intermediate Similarity	NPD3787	Discontinued
0.755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2935	Discontinued
0.7533	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD2800	Approved
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3750	Approved
0.7421	Intermediate Similarity	NPD6190	Approved
0.7414	Intermediate Similarity	NPD6559	Discontinued
0.7412	Intermediate Similarity	NPD5242	Approved
0.741	Intermediate Similarity	NPD5353	Approved
0.7405	Intermediate Similarity	NPD2654	Approved
0.7403	Intermediate Similarity	NPD230	Phase 1
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD2532	Approved
0.7391	Intermediate Similarity	NPD2533	Approved
0.7391	Intermediate Similarity	NPD2534	Approved
0.7372	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3018	Phase 2
0.7333	Intermediate Similarity	NPD6385	Approved
0.7333	Intermediate Similarity	NPD6386	Approved
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1551	Phase 2
0.7321	Intermediate Similarity	NPD3749	Approved
0.732	Intermediate Similarity	NPD2313	Discontinued
0.7317	Intermediate Similarity	NPD3226	Approved
0.731	Intermediate Similarity	NPD5536	Phase 2
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD1471	Phase 3
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD7768	Phase 2
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.7262	Intermediate Similarity	NPD4966	Approved
0.7261	Intermediate Similarity	NPD2799	Discontinued
0.7256	Intermediate Similarity	NPD1653	Approved
0.725	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2981	Phase 2
0.7244	Intermediate Similarity	NPD6651	Approved
0.7243	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD6100	Approved
0.72	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD2982	Phase 2
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7178	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3146	Approved
0.7176	Intermediate Similarity	NPD6234	Discontinued
0.7171	Intermediate Similarity	NPD2798	Approved
0.717	Intermediate Similarity	NPD2346	Discontinued
0.717	Intermediate Similarity	NPD2344	Approved
0.7159	Intermediate Similarity	NPD5953	Discontinued
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7134	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7390	Discontinued
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7105	Intermediate Similarity	NPD3266	Approved
0.7105	Intermediate Similarity	NPD3267	Approved
0.7099	Intermediate Similarity	NPD3887	Approved
0.7097	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2353	Approved
0.7063	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD17	Approved
0.7045	Intermediate Similarity	NPD7286	Phase 2
0.702	Intermediate Similarity	NPD3972	Approved
0.7013	Intermediate Similarity	NPD9494	Approved
0.7006	Intermediate Similarity	NPD4307	Phase 2
0.6994	Remote Similarity	NPD2309	Approved
0.6993	Remote Similarity	NPD1203	Approved
0.6989	Remote Similarity	NPD2163	Approved
0.6987	Remote Similarity	NPD1296	Phase 2
0.6987	Remote Similarity	NPD3268	Approved
0.6977	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6780	Approved
0.6968	Remote Similarity	NPD6777	Approved
0.6968	Remote Similarity	NPD6779	Approved
0.6968	Remote Similarity	NPD6781	Approved
0.6968	Remote Similarity	NPD6776	Approved
0.6968	Remote Similarity	NPD6778	Approved
0.6968	Remote Similarity	NPD6782	Approved
0.6962	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1019	Discontinued
0.6947	Remote Similarity	NPD7435	Discontinued
0.6937	Remote Similarity	NPD7033	Discontinued
0.6933	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7685	Pre-registration
0.6918	Remote Similarity	NPD1241	Discontinued
0.6918	Remote Similarity	NPD5283	Phase 1
0.6913	Remote Similarity	NPD1548	Phase 1
0.6909	Remote Similarity	NPD4357	Discontinued
0.6908	Remote Similarity	NPD9717	Approved
0.6908	Remote Similarity	NPD1608	Approved
0.6894	Remote Similarity	NPD3539	Phase 1
0.6893	Remote Similarity	NPD7228	Approved
0.689	Remote Similarity	NPD2354	Approved
0.6883	Remote Similarity	NPD2797	Approved
0.6867	Remote Similarity	NPD9268	Approved
0.6859	Remote Similarity	NPD4908	Phase 1
0.6859	Remote Similarity	NPD7698	Approved
0.6859	Remote Similarity	NPD7696	Phase 3
0.6859	Remote Similarity	NPD7697	Approved
0.6857	Remote Similarity	NPD5711	Approved
0.6857	Remote Similarity	NPD7229	Phase 3
0.6857	Remote Similarity	NPD5710	Approved
0.6852	Remote Similarity	NPD3540	Phase 1
0.6842	Remote Similarity	NPD422	Phase 1
0.6832	Remote Similarity	NPD4308	Phase 3
0.6831	Remote Similarity	NPD8150	Discontinued
0.6824	Remote Similarity	NPD5090	Approved
0.6824	Remote Similarity	NPD5089	Approved
0.6823	Remote Similarity	NPD7871	Phase 2
0.6823	Remote Similarity	NPD7870	Phase 2
0.6818	Remote Similarity	NPD3225	Approved
0.6815	Remote Similarity	NPD7095	Approved
0.6806	Remote Similarity	NPD5006	Approved
0.6806	Remote Similarity	NPD5005	Approved
0.6802	Remote Similarity	NPD5978	Approved
0.6802	Remote Similarity	NPD4288	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