NPASS Compound

Structure

NPC158874 OpenBabel07101718292D 32 34 0 0 0 0 0 0 0 0999 V2000 -6.0622 -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 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -4.3301 -1.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -2.0000 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 0.8660 -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 0.0000 -2.0000 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 -0.8660 -1.5000 0.0000 C 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 -3.0000 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 0.0000 -3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 31 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 18 2 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 2 0 0 0 0 16 23 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 27 1 0 0 0 0 20 22 2 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 30 2 0 0 0 0 25 26 2 0 0 0 0 25 32 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	458.959
LogP:	6.263
LogD:	3.711
LogS:	-3.207
# Rotatable Bonds:	6
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	3.063
Fsp3:	0.269
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:	-4.874
MDCK Permeability:	1.2861582945333794e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.237
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.788

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	87.57182312011719%
Volume Distribution (VD):	0.919
Pgp-substrate:	10.617414474487305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.801
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.855
CYP2D6-substrate:	0.306
CYP3A4-inhibitor:	0.462
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	8.8
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.873
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.24
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.773
Skin Sensitization:	0.889
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.865
Respiratory Toxicity:	0.231

Download Data

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

Natural Product: NPC158874

Natural Product ID:	NPC158874
*Common Name:**	5,7,4'-Trihydroxy-3',5'-Bis(3-Methyl-2-Buten-1-Yl)-3-Methoxyflavone
IUPAC Name:	5,7-dihydroxy-2-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]-3-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	OABSCYOEXNPPTI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-14(2)6-8-16-10-18(11-17(23(16)29)9-7-15(3)4)25-26(31-5)24(30)22-20(28)12-19(27)13-21(22)32-25/h6-7,10-13,27-29H,8-9H2,1-5H3
SMILES:	CC(=CCc1cc(cc(CC=C(C)C)c1O)c1c(c(=O)c2c(cc(cc2o1)O)O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2037155
PubChem CID:	70683923
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003502] 3'-prenylated flavones

*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
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	169.9	%	PMID[547837]

☑ 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 NPC158874 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	415
0.1-0.2	1703
0.2-0.3	4431
0.3-0.4	10598
0.4-0.5	7575
0.5-0.6	3801
0.6-0.7	5448
0.7-0.8	4149
0.8-0.85	2365
0.85-0.9	1722
0.9-0.95	455
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC306488
0.9856	High Similarity	NPC178343
0.9856	High Similarity	NPC5820
0.9856	High Similarity	NPC470458
0.9784	High Similarity	NPC216538
0.9784	High Similarity	NPC273538
0.9783	High Similarity	NPC200694
0.9716	High Similarity	NPC470460
0.9714	High Similarity	NPC124729
0.9712	High Similarity	NPC293053
0.9712	High Similarity	NPC190637
0.9712	High Similarity	NPC24821
0.9712	High Similarity	NPC212932
0.9712	High Similarity	NPC9117
0.971	High Similarity	NPC90582
0.971	High Similarity	NPC262094
0.9648	High Similarity	NPC470461
0.9643	High Similarity	NPC326500
0.964	High Similarity	NPC473042
0.9638	High Similarity	NPC230285
0.9638	High Similarity	NPC159275
0.9638	High Similarity	NPC184536
0.9638	High Similarity	NPC146679
0.9638	High Similarity	NPC59951
0.9638	High Similarity	NPC241100
0.9638	High Similarity	NPC103342
0.9638	High Similarity	NPC103904
0.9577	High Similarity	NPC296869
0.9577	High Similarity	NPC244407
0.9568	High Similarity	NPC110969
0.9568	High Similarity	NPC282300
0.9568	High Similarity	NPC136840
0.9565	High Similarity	NPC216978
0.9565	High Similarity	NPC241838
0.9565	High Similarity	NPC55018
0.9565	High Similarity	NPC303633
0.9565	High Similarity	NPC143799
0.9565	High Similarity	NPC18260
0.9565	High Similarity	NPC78913
0.9565	High Similarity	NPC217186
0.9565	High Similarity	NPC301217
0.9565	High Similarity	NPC53181
0.9565	High Similarity	NPC220062
0.9565	High Similarity	NPC96565
0.9565	High Similarity	NPC152042
0.9507	High Similarity	NPC14001
0.9507	High Similarity	NPC166757
0.9504	High Similarity	NPC224714
0.95	High Similarity	NPC11561
0.95	High Similarity	NPC226636
0.9496	High Similarity	NPC270883
0.9496	High Similarity	NPC172986
0.9496	High Similarity	NPC281207
0.9496	High Similarity	NPC269652
0.9496	High Similarity	NPC261227
0.9496	High Similarity	NPC150522
0.9493	High Similarity	NPC276905
0.9493	High Similarity	NPC201395
0.9489	High Similarity	NPC174999
0.9444	High Similarity	NPC61258
0.9437	High Similarity	NPC220418
0.9433	High Similarity	NPC470216
0.9429	High Similarity	NPC147688
0.9429	High Similarity	NPC205006
0.9429	High Similarity	NPC17170
0.9429	High Similarity	NPC258630
0.9429	High Similarity	NPC64908
0.9429	High Similarity	NPC156190
0.9429	High Similarity	NPC96408
0.9429	High Similarity	NPC166689
0.9429	High Similarity	NPC279650
0.9429	High Similarity	NPC156590
0.9429	High Similarity	NPC103362
0.9429	High Similarity	NPC118840
0.9384	High Similarity	NPC236756
0.9384	High Similarity	NPC311579
0.9375	High Similarity	NPC269420
0.9371	High Similarity	NPC259632
0.9366	High Similarity	NPC319752
0.9366	High Similarity	NPC470890
0.9366	High Similarity	NPC234629
0.9366	High Similarity	NPC311741
0.9362	High Similarity	NPC161506
0.9362	High Similarity	NPC324436
0.9362	High Similarity	NPC177354
0.9362	High Similarity	NPC78803
0.9362	High Similarity	NPC32739
0.9362	High Similarity	NPC296917
0.9362	High Similarity	NPC66515
0.9362	High Similarity	NPC62840
0.9362	High Similarity	NPC328164
0.9362	High Similarity	NPC194432
0.9362	High Similarity	NPC306829
0.9362	High Similarity	NPC10937
0.9362	High Similarity	NPC148757
0.9362	High Similarity	NPC125855
0.9362	High Similarity	NPC228504
0.9362	High Similarity	NPC324134
0.9362	High Similarity	NPC293852
0.9362	High Similarity	NPC166934
0.9362	High Similarity	NPC182852
0.9362	High Similarity	NPC220998
0.9362	High Similarity	NPC204469
0.9362	High Similarity	NPC37496
0.9362	High Similarity	NPC64915
0.9362	High Similarity	NPC167624
0.9362	High Similarity	NPC107572
0.9362	High Similarity	NPC227579
0.9362	High Similarity	NPC214236
0.9362	High Similarity	NPC40833
0.9362	High Similarity	NPC299080
0.9362	High Similarity	NPC76338
0.9362	High Similarity	NPC223500
0.9362	High Similarity	NPC265040
0.9362	High Similarity	NPC59739
0.9362	High Similarity	NPC1089
0.9362	High Similarity	NPC78
0.9362	High Similarity	NPC166482
0.9362	High Similarity	NPC217083
0.9362	High Similarity	NPC76372
0.9357	High Similarity	NPC69769
0.9357	High Similarity	NPC305355
0.9357	High Similarity	NPC235239
0.9357	High Similarity	NPC475680
0.9353	High Similarity	NPC131130
0.9348	High Similarity	NPC234133
0.9348	High Similarity	NPC187432
0.9348	High Similarity	NPC256042
0.9348	High Similarity	NPC29353
0.9348	High Similarity	NPC124784
0.9348	High Similarity	NPC72452
0.9348	High Similarity	NPC216361
0.9348	High Similarity	NPC194281
0.9348	High Similarity	NPC116775
0.9348	High Similarity	NPC473887
0.9348	High Similarity	NPC127447
0.9348	High Similarity	NPC61546
0.9348	High Similarity	NPC47815
0.9348	High Similarity	NPC13408
0.9348	High Similarity	NPC231772
0.9348	High Similarity	NPC281917
0.9343	High Similarity	NPC125920
0.932	High Similarity	NPC133392
0.9306	High Similarity	NPC168085
0.9301	High Similarity	NPC111786
0.9301	High Similarity	NPC476088
0.9301	High Similarity	NPC187282
0.9301	High Similarity	NPC20488
0.9301	High Similarity	NPC195621
0.9301	High Similarity	NPC472629
0.9301	High Similarity	NPC290133
0.9301	High Similarity	NPC267375
0.9301	High Similarity	NPC176229
0.9301	High Similarity	NPC153758
0.9301	High Similarity	NPC88964
0.9301	High Similarity	NPC214774
0.9301	High Similarity	NPC470647
0.9301	High Similarity	NPC83357
0.9301	High Similarity	NPC142405
0.9301	High Similarity	NPC54577
0.9301	High Similarity	NPC474161
0.9301	High Similarity	NPC312973
0.9301	High Similarity	NPC24136
0.9301	High Similarity	NPC475052
0.9301	High Similarity	NPC67805
0.9301	High Similarity	NPC246948
0.9301	High Similarity	NPC301276
0.9301	High Similarity	NPC329678
0.9296	High Similarity	NPC143896
0.9296	High Similarity	NPC39329
0.9296	High Similarity	NPC149026
0.9296	High Similarity	NPC91560
0.9296	High Similarity	NPC310130
0.9296	High Similarity	NPC278249
0.9296	High Similarity	NPC150408
0.9296	High Similarity	NPC219915
0.9296	High Similarity	NPC221432
0.9296	High Similarity	NPC316816
0.9296	High Similarity	NPC106985
0.9296	High Similarity	NPC68104
0.9296	High Similarity	NPC11700
0.9296	High Similarity	NPC185276
0.9296	High Similarity	NPC107177
0.9296	High Similarity	NPC164980
0.9296	High Similarity	NPC214166
0.9296	High Similarity	NPC478086
0.9296	High Similarity	NPC75049
0.9296	High Similarity	NPC257097
0.9296	High Similarity	NPC169591
0.9296	High Similarity	NPC38219
0.9296	High Similarity	NPC125894
0.9296	High Similarity	NPC18585
0.9296	High Similarity	NPC223812
0.9296	High Similarity	NPC166138
0.9296	High Similarity	NPC175504
0.9296	High Similarity	NPC77794
0.9296	High Similarity	NPC81697
0.9296	High Similarity	NPC85162
0.9291	High Similarity	NPC3188
0.9291	High Similarity	NPC14871

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 NPC158874 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	975
0.2-0.3	1708
0.3-0.4	2670
0.4-0.5	1863
0.5-0.6	1032
0.6-0.7	362
0.7-0.8	107
0.8-0.85	47
0.85-0.9	14
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9784	High Similarity	NPD4378	Clinical (unspecified phase)
0.9097	High Similarity	NPD7410	Clinical (unspecified phase)
0.9007	High Similarity	NPD1550	Clinical (unspecified phase)
0.9007	High Similarity	NPD1552	Clinical (unspecified phase)
0.8944	High Similarity	NPD1549	Phase 2
0.894	High Similarity	NPD7075	Discontinued
0.8926	High Similarity	NPD6801	Discontinued
0.8867	High Similarity	NPD2393	Clinical (unspecified phase)
0.8867	High Similarity	NPD7096	Clinical (unspecified phase)
0.8865	High Similarity	NPD1510	Phase 2
0.8849	High Similarity	NPD1240	Approved
0.8803	High Similarity	NPD2796	Approved
0.8792	High Similarity	NPD4380	Phase 2
0.8776	High Similarity	NPD1512	Approved
0.8767	High Similarity	NPD6799	Approved
0.8733	High Similarity	NPD7411	Suspended
0.8723	High Similarity	NPD1607	Approved
0.8684	High Similarity	NPD8443	Clinical (unspecified phase)
0.8671	High Similarity	NPD7804	Clinical (unspecified phase)
0.8639	High Similarity	NPD1511	Approved
0.8618	High Similarity	NPD2801	Approved
0.8562	High Similarity	NPD3817	Phase 2
0.8553	High Similarity	NPD1934	Approved
0.8543	High Similarity	NPD6599	Discontinued
0.8506	High Similarity	NPD3882	Suspended
0.8497	Intermediate Similarity	NPD7819	Suspended
0.8493	Intermediate Similarity	NPD2800	Approved
0.8452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.8367	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6166	Phase 2
0.8365	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5403	Approved
0.8333	Intermediate Similarity	NPD6651	Approved
0.8311	Intermediate Similarity	NPD3750	Approved
0.8299	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7768	Phase 2
0.825	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1243	Approved
0.8221	Intermediate Similarity	NPD6797	Phase 2
0.8212	Intermediate Similarity	NPD5401	Approved
0.8182	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7251	Discontinued
0.8163	Intermediate Similarity	NPD2935	Discontinued
0.8121	Intermediate Similarity	NPD7808	Phase 3
0.8105	Intermediate Similarity	NPD920	Approved
0.8092	Intermediate Similarity	NPD2534	Approved
0.8092	Intermediate Similarity	NPD2533	Approved
0.8092	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD5402	Approved
0.8056	Intermediate Similarity	NPD2313	Discontinued
0.8041	Intermediate Similarity	NPD1551	Phase 2
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD5494	Approved
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7988	Intermediate Similarity	NPD7054	Approved
0.7987	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7974	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2799	Discontinued
0.7973	Intermediate Similarity	NPD3748	Approved
0.7961	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1247	Approved
0.7939	Intermediate Similarity	NPD7074	Phase 3
0.7939	Intermediate Similarity	NPD7472	Approved
0.7937	Intermediate Similarity	NPD919	Approved
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5953	Discontinued
0.7867	Intermediate Similarity	NPD2344	Approved
0.7852	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6559	Discontinued
0.7832	Intermediate Similarity	NPD1203	Approved
0.7829	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3268	Approved
0.78	Intermediate Similarity	NPD6100	Approved
0.78	Intermediate Similarity	NPD6099	Approved
0.7792	Intermediate Similarity	NPD7390	Discontinued
0.7771	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1548	Phase 1
0.7733	Intermediate Similarity	NPD7033	Discontinued
0.7708	Intermediate Similarity	NPD2797	Approved
0.7679	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD422	Phase 1
0.7671	Intermediate Similarity	NPD4908	Phase 1
0.7671	Intermediate Similarity	NPD6832	Phase 2
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.7662	Intermediate Similarity	NPD2309	Approved
0.7657	Intermediate Similarity	NPD4363	Phase 3
0.7657	Intermediate Similarity	NPD4360	Phase 2
0.7655	Intermediate Similarity	NPD2798	Approved
0.7647	Intermediate Similarity	NPD2654	Approved
0.7636	Intermediate Similarity	NPD3926	Phase 2
0.7632	Intermediate Similarity	NPD2346	Discontinued
0.7622	Intermediate Similarity	NPD9717	Approved
0.7597	Intermediate Similarity	NPD4628	Phase 3
0.7597	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD943	Approved
0.7568	Intermediate Similarity	NPD6798	Discontinued
0.7562	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7533	Intermediate Similarity	NPD5124	Phase 1
0.7533	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3225	Approved
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7485	Intermediate Similarity	NPD2403	Approved
0.747	Intermediate Similarity	NPD5710	Approved
0.747	Intermediate Similarity	NPD5711	Approved
0.7469	Intermediate Similarity	NPD1465	Phase 2
0.7466	Intermediate Similarity	NPD3267	Approved
0.7466	Intermediate Similarity	NPD3266	Approved
0.7443	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1729	Discontinued
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.74	Intermediate Similarity	NPD6233	Phase 2
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7381	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3972	Approved
0.7365	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5049	Phase 3
0.7333	Intermediate Similarity	NPD1296	Phase 2
0.7325	Intermediate Similarity	NPD2354	Approved
0.7317	Intermediate Similarity	NPD4288	Approved
0.7315	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD230	Phase 1
0.7303	Intermediate Similarity	NPD6355	Discontinued
0.7303	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1933	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9545	Approved
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.726	Intermediate Similarity	NPD1608	Approved
0.7254	Intermediate Similarity	NPD9493	Approved
0.7239	Intermediate Similarity	NPD5890	Approved
0.7239	Intermediate Similarity	NPD5889	Approved
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.7237	Intermediate Similarity	NPD1613	Approved
0.7237	Intermediate Similarity	NPD4307	Phase 2
0.7237	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7458	Discontinued
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3887	Approved
0.7211	Intermediate Similarity	NPD4749	Approved
0.7204	Intermediate Similarity	NPD7584	Approved
0.7192	Intermediate Similarity	NPD1201	Approved
0.719	Intermediate Similarity	NPD447	Suspended
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7179	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2353	Approved
0.7178	Intermediate Similarity	NPD6585	Discontinued
0.7163	Intermediate Similarity	NPD1241	Discontinued
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7126	Intermediate Similarity	NPD6104	Discontinued
0.7125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5404	Approved
0.7115	Intermediate Similarity	NPD5406	Approved
0.7115	Intermediate Similarity	NPD5405	Approved
0.7115	Intermediate Similarity	NPD5408	Approved
0.7114	Intermediate Similarity	NPD1164	Approved
0.7114	Intermediate Similarity	NPD1470	Approved
0.7108	Intermediate Similarity	NPD2296	Approved
0.7105	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD411	Approved
0.7105	Intermediate Similarity	NPD3764	Approved
0.7103	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6844	Discontinued
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7078	Intermediate Similarity	NPD4340	Discontinued
0.7075	Intermediate Similarity	NPD1535	Discovery
0.7065	Intermediate Similarity	NPD6776	Approved
0.7065	Intermediate Similarity	NPD6778	Approved
0.7065	Intermediate Similarity	NPD6782	Approved
0.7065	Intermediate Similarity	NPD6781	Approved
0.7065	Intermediate Similarity	NPD6780	Approved
0.7065	Intermediate Similarity	NPD6777	Approved
0.7065	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD4062	Phase 3
0.7055	Intermediate Similarity	NPD17	Approved
0.7045	Intermediate Similarity	NPD8313	Approved
0.7045	Intermediate Similarity	NPD8312	Approved
0.7043	Intermediate Similarity	NPD7435	Discontinued
0.7039	Intermediate Similarity	NPD3027	Phase 3
0.7039	Intermediate Similarity	NPD4287	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