NPASS Compound

Structure

CID162680 OpenBabel06191715532D 22 24 0 0 0 0 0 0 0 0999 V2000 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 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 -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 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 -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 -3.4641 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 -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 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 -0.0000 -0.0000 0.0000 C 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 5 1 0 0 0 0 3 10 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 15 2 0 0 0 0 9 13 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 17 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	3.127
LogD:	2.812
LogS:	-3.673
# Rotatable Bonds:	3
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	2.165
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.665
MDCK Permeability:	2.516552194720134e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.882
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	93.48739624023438%
Volume Distribution (VD):	0.509
Pgp-substrate:	4.4431257247924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.788
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.871
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.817
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	6.31
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.554
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.335
Skin Sensitization:	0.687
Carcinogencity:	0.174
Eye Corrosion:	0.022
Eye Irritation:	0.944
Respiratory Toxicity:	0.293

Download Data

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

Natural Product: NPC162680

Natural Product ID:	NPC162680
*Common Name:**	4'-Hydroxy-5,7-Dimethoxyisoflavone
IUPAC Name:	3-(4-hydroxyphenyl)-5,7-dimethoxychromen-4-one
Synonyms:
Standard InCHIKey:	YZBVKMUAJDLNMZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-20-12-7-14(21-2)16-15(8-12)22-9-13(17(16)19)10-3-5-11(18)6-4-10/h3-9,18H,1-2H3
SMILES:	COc1cc(OC)cc2c1c(=O)c(co2)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445815
PubChem CID:	12458245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002602] 7-O-methylated isoflavonoids [CHEMONTID:0002689] 7-O-methylisoflavones

*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
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(88)80746-5]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	root barks	n.a.	n.a.	PMID[15689169]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	root bark	Buea, Southwest Province, Cameroon	1997-JUL	PMID[17125223]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22444	Ceramium boydenii	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27459	Balanophora tobiracola	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	60000.0	nM	PMID[553009]

☑ 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 NPC162680 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	402
0.1-0.2	1789
0.2-0.3	4239
0.3-0.4	11028
0.4-0.5	7048
0.5-0.6	3947
0.6-0.7	5861
0.7-0.8	4445
0.8-0.85	1986
0.85-0.9	1475
0.9-0.95	392
0.95-1	85

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC303644
1.0	High Similarity	NPC209560
1.0	High Similarity	NPC7013
1.0	High Similarity	NPC294409
1.0	High Similarity	NPC181124
1.0	High Similarity	NPC116632
0.9924	High Similarity	NPC55162
0.9924	High Similarity	NPC278323
0.9924	High Similarity	NPC279668
0.9924	High Similarity	NPC12175
0.9924	High Similarity	NPC309154
0.9924	High Similarity	NPC90665
0.985	High Similarity	NPC295384
0.9847	High Similarity	NPC39426
0.9847	High Similarity	NPC234560
0.9776	High Similarity	NPC144118
0.9776	High Similarity	NPC219917
0.9776	High Similarity	NPC215311
0.9776	High Similarity	NPC48624
0.9776	High Similarity	NPC80962
0.9776	High Similarity	NPC101366
0.9776	High Similarity	NPC259166
0.9776	High Similarity	NPC326109
0.9776	High Similarity	NPC213659
0.9776	High Similarity	NPC172250
0.9776	High Similarity	NPC204985
0.9773	High Similarity	NPC87545
0.9773	High Similarity	NPC235428
0.9704	High Similarity	NPC26051
0.9704	High Similarity	NPC469404
0.9704	High Similarity	NPC55832
0.9704	High Similarity	NPC268204
0.9704	High Similarity	NPC52789
0.9701	High Similarity	NPC283429
0.9699	High Similarity	NPC212767
0.963	High Similarity	NPC253822
0.9624	High Similarity	NPC193792
0.9621	High Similarity	NPC286336
0.9618	High Similarity	NPC182428
0.9618	High Similarity	NPC212631
0.9618	High Similarity	NPC129132
0.9618	High Similarity	NPC257756
0.9618	High Similarity	NPC205468
0.9618	High Similarity	NPC87231
0.9562	High Similarity	NPC475705
0.9562	High Similarity	NPC476178
0.9562	High Similarity	NPC117836
0.9562	High Similarity	NPC51887
0.9552	High Similarity	NPC250266
0.9552	High Similarity	NPC266597
0.9552	High Similarity	NPC228661
0.9545	High Similarity	NPC294593
0.9545	High Similarity	NPC82225
0.9545	High Similarity	NPC159623
0.9545	High Similarity	NPC188646
0.9545	High Similarity	NPC223354
0.9545	High Similarity	NPC204960
0.9545	High Similarity	NPC312318
0.9545	High Similarity	NPC472365
0.9545	High Similarity	NPC18877
0.9545	High Similarity	NPC337373
0.9545	High Similarity	NPC263670
0.9545	High Similarity	NPC175098
0.9545	High Similarity	NPC56031
0.9545	High Similarity	NPC139813
0.9545	High Similarity	NPC20560
0.9545	High Similarity	NPC144051
0.9545	High Similarity	NPC192304
0.9545	High Similarity	NPC28753
0.9545	High Similarity	NPC242294
0.9542	High Similarity	NPC262359
0.9542	High Similarity	NPC308037
0.9542	High Similarity	NPC313618
0.9542	High Similarity	NPC64359
0.9493	High Similarity	NPC476055
0.9489	High Similarity	NPC202981
0.9481	High Similarity	NPC21350
0.9481	High Similarity	NPC99333
0.9481	High Similarity	NPC188947
0.9481	High Similarity	NPC124269
0.9481	High Similarity	NPC280284
0.9478	High Similarity	NPC29353
0.9478	High Similarity	NPC186838
0.9478	High Similarity	NPC168105
0.9478	High Similarity	NPC124784
0.9478	High Similarity	NPC473391
0.9478	High Similarity	NPC25287
0.9478	High Similarity	NPC66349
0.9478	High Similarity	NPC194281
0.9478	High Similarity	NPC127447
0.9478	High Similarity	NPC472364
0.9478	High Similarity	NPC231772
0.9478	High Similarity	NPC477242
0.9478	High Similarity	NPC473887
0.9478	High Similarity	NPC477244
0.9478	High Similarity	NPC274109
0.9478	High Similarity	NPC1486
0.9478	High Similarity	NPC41461
0.9478	High Similarity	NPC234133
0.9478	High Similarity	NPC249606
0.9478	High Similarity	NPC150399
0.9478	High Similarity	NPC12165
0.9478	High Similarity	NPC47815
0.9478	High Similarity	NPC98115
0.9478	High Similarity	NPC213603
0.9478	High Similarity	NPC477243
0.9424	High Similarity	NPC12377
0.9416	High Similarity	NPC470087
0.9416	High Similarity	NPC321980
0.9416	High Similarity	NPC470089
0.9416	High Similarity	NPC110969
0.9416	High Similarity	NPC3188
0.9412	High Similarity	NPC18260
0.9412	High Similarity	NPC49242
0.9412	High Similarity	NPC261234
0.9412	High Similarity	NPC265871
0.9412	High Similarity	NPC274784
0.9412	High Similarity	NPC150648
0.9412	High Similarity	NPC329203
0.9412	High Similarity	NPC222342
0.9412	High Similarity	NPC78913
0.9412	High Similarity	NPC470211
0.9412	High Similarity	NPC310135
0.9412	High Similarity	NPC477956
0.9412	High Similarity	NPC225153
0.9412	High Similarity	NPC20709
0.9407	High Similarity	NPC290291
0.9407	High Similarity	NPC188879
0.9407	High Similarity	NPC275055
0.9407	High Similarity	NPC472419
0.9407	High Similarity	NPC317119
0.9407	High Similarity	NPC153979
0.9403	High Similarity	NPC13575
0.9403	High Similarity	NPC131039
0.9403	High Similarity	NPC156092
0.9394	High Similarity	NPC164236
0.9394	High Similarity	NPC475008
0.9394	High Similarity	NPC186097
0.9394	High Similarity	NPC475009
0.9394	High Similarity	NPC66384
0.9394	High Similarity	NPC128348
0.9394	High Similarity	NPC189106
0.9394	High Similarity	NPC112192
0.9394	High Similarity	NPC309717
0.9389	High Similarity	NPC185497
0.9389	High Similarity	NPC247779
0.9357	High Similarity	NPC51070
0.9357	High Similarity	NPC237635
0.9357	High Similarity	NPC79469
0.9357	High Similarity	NPC24673
0.9357	High Similarity	NPC97716
0.9357	High Similarity	NPC222298
0.9357	High Similarity	NPC104406
0.9357	High Similarity	NPC201731
0.9353	High Similarity	NPC303185
0.9353	High Similarity	NPC234629
0.9353	High Similarity	NPC184649
0.9353	High Similarity	NPC311741
0.9348	High Similarity	NPC226636
0.9348	High Similarity	NPC11561
0.9343	High Similarity	NPC188243
0.9343	High Similarity	NPC284550
0.9343	High Similarity	NPC270883
0.9343	High Similarity	NPC269652
0.9343	High Similarity	NPC172986
0.9343	High Similarity	NPC265178
0.9343	High Similarity	NPC281207
0.9343	High Similarity	NPC76445
0.9343	High Similarity	NPC261227
0.9343	High Similarity	NPC6407
0.9343	High Similarity	NPC11056
0.9343	High Similarity	NPC129853
0.9343	High Similarity	NPC110228
0.9343	High Similarity	NPC241100
0.9343	High Similarity	NPC159275
0.9338	High Similarity	NPC251681
0.9338	High Similarity	NPC243528
0.9338	High Similarity	NPC25427
0.9338	High Similarity	NPC472460
0.9338	High Similarity	NPC329225
0.9338	High Similarity	NPC201395
0.9338	High Similarity	NPC472368
0.9338	High Similarity	NPC147686
0.9338	High Similarity	NPC471620
0.9338	High Similarity	NPC118813
0.9333	High Similarity	NPC13408
0.9333	High Similarity	NPC472367
0.9333	High Similarity	NPC476333
0.9333	High Similarity	NPC254741
0.9333	High Similarity	NPC240593
0.9328	High Similarity	NPC172262
0.9328	High Similarity	NPC103842
0.9313	High Similarity	NPC60558
0.9291	High Similarity	NPC266572
0.9291	High Similarity	NPC168085
0.9291	High Similarity	NPC139364
0.9291	High Similarity	NPC194653
0.9291	High Similarity	NPC203747
0.9291	High Similarity	NPC254702
0.9291	High Similarity	NPC80710

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 NPC162680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	982
0.2-0.3	1529
0.3-0.4	2616
0.4-0.5	1893
0.5-0.6	1191
0.6-0.7	361
0.7-0.8	118
0.8-0.85	38
0.85-0.9	28
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9847	High Similarity	NPD1510	Phase 2
0.9542	High Similarity	NPD1240	Approved
0.9398	High Similarity	NPD1607	Approved
0.9338	High Similarity	NPD1549	Phase 2
0.9265	High Similarity	NPD1550	Clinical (unspecified phase)
0.9265	High Similarity	NPD1552	Clinical (unspecified phase)
0.9214	High Similarity	NPD4378	Clinical (unspecified phase)
0.9191	High Similarity	NPD2796	Approved
0.9028	High Similarity	NPD4380	Phase 2
0.8944	High Similarity	NPD7410	Clinical (unspecified phase)
0.8776	High Similarity	NPD1934	Approved
0.8741	High Similarity	NPD1511	Approved
0.8716	High Similarity	NPD2393	Clinical (unspecified phase)
0.8707	High Similarity	NPD7411	Suspended
0.8667	High Similarity	NPD4381	Clinical (unspecified phase)
0.8667	High Similarity	NPD7075	Discontinued
0.8662	High Similarity	NPD3750	Approved
0.8662	High Similarity	NPD1878	Clinical (unspecified phase)
0.8658	High Similarity	NPD8443	Clinical (unspecified phase)
0.8652	High Similarity	NPD970	Clinical (unspecified phase)
0.8621	High Similarity	NPD1512	Approved
0.8611	High Similarity	NPD6799	Approved
0.8591	High Similarity	NPD2801	Approved
0.8591	High Similarity	NPD7819	Suspended
0.8591	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD6801	Discontinued
0.8511	High Similarity	NPD1551	Phase 2
0.8477	Intermediate Similarity	NPD3882	Suspended
0.8389	Intermediate Similarity	NPD6599	Discontinued
0.838	Intermediate Similarity	NPD2935	Discontinued
0.8355	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD3748	Approved
0.8301	Intermediate Similarity	NPD3749	Approved
0.8298	Intermediate Similarity	NPD6651	Approved
0.8289	Intermediate Similarity	NPD3817	Phase 2
0.8286	Intermediate Similarity	NPD943	Approved
0.8273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD2798	Approved
0.8228	Intermediate Similarity	NPD3818	Discontinued
0.8217	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6166	Phase 2
0.8217	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD2800	Approved
0.8207	Intermediate Similarity	NPD1243	Approved
0.8194	Intermediate Similarity	NPD2344	Approved
0.8188	Intermediate Similarity	NPD920	Approved
0.8188	Intermediate Similarity	NPD5403	Approved
0.8182	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5401	Approved
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6959	Discontinued
0.8089	Intermediate Similarity	NPD6232	Discontinued
0.8063	Intermediate Similarity	NPD7054	Approved
0.8054	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2532	Approved
0.8054	Intermediate Similarity	NPD2534	Approved
0.8054	Intermediate Similarity	NPD2533	Approved
0.805	Intermediate Similarity	NPD7473	Discontinued
0.8043	Intermediate Similarity	NPD1203	Approved
0.8015	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2313	Discontinued
0.8012	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD1548	Phase 1
0.7975	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2309	Approved
0.7963	Intermediate Similarity	NPD5953	Discontinued
0.7963	Intermediate Similarity	NPD6797	Phase 2
0.7962	Intermediate Similarity	NPD5494	Approved
0.7935	Intermediate Similarity	NPD5402	Approved
0.7931	Intermediate Similarity	NPD2799	Discontinued
0.7914	Intermediate Similarity	NPD7251	Discontinued
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7883	Intermediate Similarity	NPD1610	Phase 2
0.7872	Intermediate Similarity	NPD6832	Phase 2
0.7872	Intermediate Similarity	NPD4908	Phase 1
0.7866	Intermediate Similarity	NPD7808	Phase 3
0.7852	Intermediate Similarity	NPD9545	Approved
0.784	Intermediate Similarity	NPD7286	Phase 2
0.7838	Intermediate Similarity	NPD2654	Approved
0.7836	Intermediate Similarity	NPD9493	Approved
0.7829	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3972	Approved
0.7826	Intermediate Similarity	NPD9717	Approved
0.7808	Intermediate Similarity	NPD4308	Phase 3
0.7808	Intermediate Similarity	NPD7033	Discontinued
0.7805	Intermediate Similarity	NPD6559	Discontinued
0.7785	Intermediate Similarity	NPD919	Approved
0.7762	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD3268	Approved
0.7758	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6099	Approved
0.7755	Intermediate Similarity	NPD6100	Approved
0.7754	Intermediate Similarity	NPD422	Phase 1
0.7748	Intermediate Similarity	NPD7390	Discontinued
0.7727	Intermediate Similarity	NPD3226	Approved
0.7724	Intermediate Similarity	NPD230	Phase 1
0.7688	Intermediate Similarity	NPD1247	Approved
0.766	Intermediate Similarity	NPD2797	Approved
0.766	Intermediate Similarity	NPD1470	Approved
0.7639	Intermediate Similarity	NPD3764	Approved
0.7626	Intermediate Similarity	NPD1201	Approved
0.7622	Intermediate Similarity	NPD5844	Phase 1
0.7613	Intermediate Similarity	NPD7458	Discontinued
0.7603	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4288	Approved
0.7593	Intermediate Similarity	NPD3926	Phase 2
0.7589	Intermediate Similarity	NPD3225	Approved
0.7589	Intermediate Similarity	NPD1876	Approved
0.7584	Intermediate Similarity	NPD2346	Discontinued
0.7568	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3267	Approved
0.7535	Intermediate Similarity	NPD1164	Approved
0.7535	Intermediate Similarity	NPD3266	Approved
0.7534	Intermediate Similarity	NPD4307	Phase 2
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.753	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7483	Intermediate Similarity	NPD1933	Approved
0.7481	Intermediate Similarity	NPD1241	Discontinued
0.7471	Intermediate Similarity	NPD4361	Phase 2
0.7471	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3027	Phase 3
0.7447	Intermediate Similarity	NPD1608	Approved
0.7434	Intermediate Similarity	NPD7003	Approved
0.7431	Intermediate Similarity	NPD9494	Approved
0.7429	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5711	Approved
0.7423	Intermediate Similarity	NPD5710	Approved
0.7415	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1613	Approved
0.7403	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5404	Approved
0.74	Intermediate Similarity	NPD5408	Approved
0.74	Intermediate Similarity	NPD5406	Approved
0.74	Intermediate Similarity	NPD5405	Approved
0.7397	Intermediate Similarity	NPD411	Approved
0.7397	Intermediate Similarity	NPD1296	Phase 2
0.7379	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2296	Approved
0.7365	Intermediate Similarity	NPD447	Suspended
0.7365	Intermediate Similarity	NPD1729	Discontinued
0.7365	Intermediate Similarity	NPD5124	Phase 1
0.7365	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1019	Discontinued
0.7355	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4287	Approved
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7278	Intermediate Similarity	NPD6104	Discontinued
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6844	Discontinued
0.7246	Intermediate Similarity	NPD3751	Discontinued
0.7239	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD9266	Approved
0.7237	Intermediate Similarity	NPD1471	Phase 3
0.7237	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD17	Approved
0.7229	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4625	Phase 3
0.7207	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5890	Approved
0.7188	Intermediate Similarity	NPD5889	Approved
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9267	Approved
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9264	Approved
0.7164	Intermediate Similarity	NPD9263	Approved
0.7163	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2354	Approved
0.7158	Intermediate Similarity	NPD7584	Approved
0.7153	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD6279	Approved
0.7134	Intermediate Similarity	NPD7447	Phase 1
0.7134	Intermediate Similarity	NPD4661	Approved
0.7134	Intermediate Similarity	NPD4662	Approved
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7108	Intermediate Similarity	NPD7229	Phase 3
0.7103	Intermediate Similarity	NPD1283	Approved
0.7092	Intermediate Similarity	NPD1894	Discontinued
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9269	Phase 2
0.7083	Intermediate Similarity	NPD1481	Phase 2
0.7075	Intermediate Similarity	NPD2861	Phase 2
0.7073	Intermediate Similarity	NPD6971	Discontinued
0.707	Intermediate Similarity	NPD7213	Phase 3
0.707	Intermediate Similarity	NPD7212	Phase 2
0.7067	Intermediate Similarity	NPD3140	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