NPASS Compound

Structure

NPC193792 OpenBabel07101718292D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 1.0000 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 -3.4641 1.0000 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 -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 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 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 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 7 2 0 0 0 0 1 8 1 0 0 0 0 2 7 1 0 0 0 0 2 9 2 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 5 13 2 0 0 0 0 6 11 2 0 0 0 0 6 21 1 0 0 0 0 7 11 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	2.106
LogD:	2.526
LogS:	-3.394
# Rotatable Bonds:	1
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	2.595
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.041
MDCK Permeability:	6.152978585305391e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.402
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	92.1746597290039%
Volume Distribution (VD):	0.752
Pgp-substrate:	4.507850646972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.506
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.854
CYP2D6-substrate:	0.512
CYP3A4-inhibitor:	0.808
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	8.96
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.153
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.302
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.941
Carcinogencity:	0.037
Eye Corrosion:	0.064
Eye Irritation:	0.942
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC193792

Natural Product ID:	NPC193792
*Common Name:**	5,7-Dihydroxy-3',5'-Dihydroxyisoflavone
IUPAC Name:	3-(3,5-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	XCLBJTYTTUIYQL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-8-1-7(2-9(17)3-8)11-6-21-13-5-10(18)4-12(19)14(13)15(11)20/h1-6,16-19H
SMILES:	Oc1cc(O)cc(c1)c1coc2c(c1=O)c(O)cc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079734
PubChem CID:	46879752
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	4
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	GI50	=	133000.0	nM	PMID[525658]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	75000.0	nM	PMID[525658]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	134000.0	nM	PMID[525658]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	65000.0	nM	PMID[525658]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	174000.0	nM	PMID[525658]

☑ 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 NPC193792 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	496
0.1-0.2	2023
0.2-0.3	4872
0.3-0.4	11626
0.4-0.5	5930
0.5-0.6	4131
0.6-0.7	5526
0.7-0.8	4522
0.8-0.85	2160
0.85-0.9	1143
0.9-0.95	239
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC212767
0.9771	High Similarity	NPC234560
0.9771	High Similarity	NPC39426
0.9697	High Similarity	NPC87545
0.9697	High Similarity	NPC235428
0.9624	High Similarity	NPC7013
0.9624	High Similarity	NPC116632
0.9624	High Similarity	NPC303644
0.9624	High Similarity	NPC209560
0.9624	High Similarity	NPC181124
0.9624	High Similarity	NPC294409
0.9624	High Similarity	NPC162680
0.9552	High Similarity	NPC90665
0.9552	High Similarity	NPC278323
0.9552	High Similarity	NPC279668
0.9552	High Similarity	NPC309154
0.9552	High Similarity	NPC55162
0.9552	High Similarity	NPC12175
0.9489	High Similarity	NPC38065
0.9489	High Similarity	NPC242893
0.9481	High Similarity	NPC295384
0.9412	High Similarity	NPC144118
0.9412	High Similarity	NPC80962
0.9412	High Similarity	NPC215311
0.9412	High Similarity	NPC253822
0.9412	High Similarity	NPC326109
0.9412	High Similarity	NPC213659
0.9412	High Similarity	NPC48624
0.9412	High Similarity	NPC204985
0.9412	High Similarity	NPC259166
0.9412	High Similarity	NPC101366
0.9412	High Similarity	NPC182421
0.9412	High Similarity	NPC219917
0.9412	High Similarity	NPC172250
0.9403	High Similarity	NPC473391
0.9403	High Similarity	NPC472364
0.9353	High Similarity	NPC12377
0.9343	High Similarity	NPC268204
0.9343	High Similarity	NPC52789
0.9343	High Similarity	NPC26051
0.9343	High Similarity	NPC469404
0.9343	High Similarity	NPC55832
0.9338	High Similarity	NPC201541
0.9338	High Similarity	NPC283429
0.9338	High Similarity	NPC469523
0.9318	High Similarity	NPC313618
0.9313	High Similarity	NPC185497
0.9286	High Similarity	NPC188074
0.9286	High Similarity	NPC125449
0.9275	High Similarity	NPC73028
0.9265	High Similarity	NPC472460
0.9265	High Similarity	NPC329225
0.9265	High Similarity	NPC147686
0.9254	High Similarity	NPC286336
0.9254	High Similarity	NPC172262
0.9248	High Similarity	NPC87231
0.9248	High Similarity	NPC257756
0.9248	High Similarity	NPC205468
0.9248	High Similarity	NPC182428
0.9248	High Similarity	NPC129132
0.9248	High Similarity	NPC212631
0.9237	High Similarity	NPC60558
0.922	High Similarity	NPC80710
0.922	High Similarity	NPC203077
0.922	High Similarity	NPC194653
0.922	High Similarity	NPC218490
0.922	High Similarity	NPC139364
0.922	High Similarity	NPC254702
0.922	High Similarity	NPC238279
0.922	High Similarity	NPC203747
0.922	High Similarity	NPC166036
0.9209	High Similarity	NPC95751
0.9209	High Similarity	NPC117836
0.9209	High Similarity	NPC51887
0.9209	High Similarity	NPC19896
0.9209	High Similarity	NPC476178
0.9209	High Similarity	NPC475705
0.9203	High Similarity	NPC49108
0.9197	High Similarity	NPC261234
0.9197	High Similarity	NPC316480
0.9197	High Similarity	NPC109232
0.9191	High Similarity	NPC13768
0.9191	High Similarity	NPC275055
0.9191	High Similarity	NPC250266
0.9191	High Similarity	NPC84585
0.9191	High Similarity	NPC32441
0.9191	High Similarity	NPC295261
0.9191	High Similarity	NPC266597
0.9191	High Similarity	NPC290291
0.9191	High Similarity	NPC107586
0.9191	High Similarity	NPC296490
0.9191	High Similarity	NPC79943
0.9191	High Similarity	NPC228661
0.9191	High Similarity	NPC243083
0.9191	High Similarity	NPC287246
0.9191	High Similarity	NPC476480
0.9191	High Similarity	NPC12296
0.9185	High Similarity	NPC239495
0.9185	High Similarity	NPC9985
0.9179	High Similarity	NPC57601
0.9179	High Similarity	NPC144051
0.9179	High Similarity	NPC263670
0.9179	High Similarity	NPC28753
0.9179	High Similarity	NPC213216
0.9179	High Similarity	NPC20560
0.9179	High Similarity	NPC50898
0.9179	High Similarity	NPC188646
0.9179	High Similarity	NPC159623
0.9179	High Similarity	NPC82225
0.9179	High Similarity	NPC294593
0.9179	High Similarity	NPC192304
0.9179	High Similarity	NPC242294
0.9179	High Similarity	NPC56031
0.9179	High Similarity	NPC175098
0.9179	High Similarity	NPC312318
0.9179	High Similarity	NPC139813
0.9179	High Similarity	NPC223354
0.9179	High Similarity	NPC78540
0.9179	High Similarity	NPC337373
0.9179	High Similarity	NPC18877
0.9179	High Similarity	NPC274121
0.9179	High Similarity	NPC204960
0.9179	High Similarity	NPC472365
0.9173	High Similarity	NPC262359
0.9173	High Similarity	NPC308037
0.9173	High Similarity	NPC64359
0.9173	High Similarity	NPC65060
0.9155	High Similarity	NPC474052
0.9155	High Similarity	NPC38545
0.9155	High Similarity	NPC40290
0.9155	High Similarity	NPC264550
0.9155	High Similarity	NPC264289
0.9155	High Similarity	NPC195763
0.9155	High Similarity	NPC200060
0.9155	High Similarity	NPC171916
0.9155	High Similarity	NPC142876
0.9155	High Similarity	NPC139293
0.9155	High Similarity	NPC333691
0.9155	High Similarity	NPC69430
0.9143	High Similarity	NPC476055
0.9137	High Similarity	NPC202981
0.9137	High Similarity	NPC287722
0.9137	High Similarity	NPC310340
0.9137	High Similarity	NPC159855
0.9137	High Similarity	NPC169479
0.913	High Similarity	NPC275734
0.9124	High Similarity	NPC280284
0.9124	High Similarity	NPC21350
0.9124	High Similarity	NPC25427
0.9124	High Similarity	NPC99333
0.9124	High Similarity	NPC118813
0.9124	High Similarity	NPC188947
0.9124	High Similarity	NPC124269
0.9118	High Similarity	NPC194281
0.9118	High Similarity	NPC66349
0.9118	High Similarity	NPC477243
0.9118	High Similarity	NPC98115
0.9118	High Similarity	NPC150399
0.9118	High Similarity	NPC29353
0.9118	High Similarity	NPC477242
0.9118	High Similarity	NPC249606
0.9118	High Similarity	NPC1486
0.9118	High Similarity	NPC124784
0.9118	High Similarity	NPC274109
0.9118	High Similarity	NPC47815
0.9118	High Similarity	NPC12165
0.9118	High Similarity	NPC213603
0.9118	High Similarity	NPC168105
0.9118	High Similarity	NPC473887
0.9118	High Similarity	NPC127447
0.9118	High Similarity	NPC234133
0.9118	High Similarity	NPC477244
0.9118	High Similarity	NPC186838
0.9118	High Similarity	NPC41461
0.9118	High Similarity	NPC25287
0.9118	High Similarity	NPC231772
0.9091	High Similarity	NPC212379
0.9091	High Similarity	NPC239363
0.9091	High Similarity	NPC10467
0.9091	High Similarity	NPC156953
0.9091	High Similarity	NPC85131
0.9091	High Similarity	NPC69235
0.9084	High Similarity	NPC128428
0.9084	High Similarity	NPC305518
0.9078	High Similarity	NPC196114
0.9078	High Similarity	NPC99454
0.9078	High Similarity	NPC187282
0.9078	High Similarity	NPC24136
0.9078	High Similarity	NPC290133
0.9078	High Similarity	NPC130176
0.9071	High Similarity	NPC475201
0.9065	High Similarity	NPC470087
0.9065	High Similarity	NPC94076
0.9065	High Similarity	NPC110969
0.9065	High Similarity	NPC182255
0.9065	High Similarity	NPC321980
0.9065	High Similarity	NPC284556
0.9065	High Similarity	NPC301178
0.9065	High Similarity	NPC470089
0.9065	High Similarity	NPC3188

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 NPC193792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	472
0.1-0.2	1024
0.2-0.3	1752
0.3-0.4	2628
0.4-0.5	1768
0.5-0.6	1019
0.6-0.7	317
0.7-0.8	111
0.8-0.85	41
0.85-0.9	15
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9771	High Similarity	NPD1510	Phase 2
0.9318	High Similarity	NPD1240	Approved
0.9265	High Similarity	NPD1549	Phase 2
0.9191	High Similarity	NPD1552	Clinical (unspecified phase)
0.9191	High Similarity	NPD1550	Clinical (unspecified phase)
0.9179	High Similarity	NPD1607	Approved
0.8936	High Similarity	NPD1511	Approved
0.8873	High Similarity	NPD4378	Clinical (unspecified phase)
0.8849	High Similarity	NPD970	Clinical (unspecified phase)
0.8841	High Similarity	NPD2796	Approved
0.8828	High Similarity	NPD4380	Phase 2
0.8811	High Similarity	NPD1512	Approved
0.8707	High Similarity	NPD1934	Approved
0.8649	High Similarity	NPD2393	Clinical (unspecified phase)
0.8611	High Similarity	NPD7410	Clinical (unspecified phase)
0.8523	High Similarity	NPD2801	Approved
0.8523	High Similarity	NPD7819	Suspended
0.8478	Intermediate Similarity	NPD943	Approved
0.8477	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3750	Approved
0.844	Intermediate Similarity	NPD1551	Phase 2
0.8411	Intermediate Similarity	NPD3882	Suspended
0.8389	Intermediate Similarity	NPD7411	Suspended
0.8369	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD2935	Discontinued
0.8288	Intermediate Similarity	NPD6799	Approved
0.828	Intermediate Similarity	NPD3818	Discontinued
0.8278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD3817	Phase 2
0.8212	Intermediate Similarity	NPD6801	Discontinued
0.8194	Intermediate Similarity	NPD6959	Discontinued
0.817	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6166	Phase 2
0.8138	Intermediate Similarity	NPD1243	Approved
0.8117	Intermediate Similarity	NPD3749	Approved
0.8112	Intermediate Similarity	NPD3748	Approved
0.8108	Intermediate Similarity	NPD2533	Approved
0.8108	Intermediate Similarity	NPD2532	Approved
0.8108	Intermediate Similarity	NPD2534	Approved
0.8099	Intermediate Similarity	NPD6651	Approved
0.8095	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6599	Discontinued
0.8052	Intermediate Similarity	NPD7768	Phase 2
0.8038	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6232	Discontinued
0.8014	Intermediate Similarity	NPD2800	Approved
0.8014	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD920	Approved
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD5401	Approved
0.7987	Intermediate Similarity	NPD5402	Approved
0.7971	Intermediate Similarity	NPD1203	Approved
0.795	Intermediate Similarity	NPD7472	Approved
0.795	Intermediate Similarity	NPD7074	Phase 3
0.7943	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2798	Approved
0.791	Intermediate Similarity	NPD1548	Phase 1
0.7902	Intermediate Similarity	NPD230	Phase 1
0.7901	Intermediate Similarity	NPD6797	Phase 2
0.7898	Intermediate Similarity	NPD5494	Approved
0.7888	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD2344	Approved
0.7853	Intermediate Similarity	NPD7251	Discontinued
0.7842	Intermediate Similarity	NPD1470	Approved
0.7834	Intermediate Similarity	NPD919	Approved
0.7817	Intermediate Similarity	NPD2313	Discontinued
0.781	Intermediate Similarity	NPD1201	Approved
0.781	Intermediate Similarity	NPD1610	Phase 2
0.7808	Intermediate Similarity	NPD6100	Approved
0.7808	Intermediate Similarity	NPD6099	Approved
0.7806	Intermediate Similarity	NPD1465	Phase 2
0.7805	Intermediate Similarity	NPD7808	Phase 3
0.7805	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7390	Discontinued
0.7763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6559	Discontinued
0.774	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1247	Approved
0.7697	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD5953	Discontinued
0.7667	Intermediate Similarity	NPD2309	Approved
0.7662	Intermediate Similarity	NPD3226	Approved
0.7651	Intermediate Similarity	NPD2654	Approved
0.7647	Intermediate Similarity	NPD9545	Approved
0.763	Intermediate Similarity	NPD9493	Approved
0.7626	Intermediate Similarity	NPD9717	Approved
0.7619	Intermediate Similarity	NPD2799	Discontinued
0.7606	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1613	Approved
0.7561	Intermediate Similarity	NPD7286	Phase 2
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7554	Intermediate Similarity	NPD422	Phase 1
0.7552	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4908	Phase 1
0.7552	Intermediate Similarity	NPD6832	Phase 2
0.7534	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3926	Phase 2
0.7517	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7483	Intermediate Similarity	NPD9494	Approved
0.7469	Intermediate Similarity	NPD5711	Approved
0.7469	Intermediate Similarity	NPD5710	Approved
0.7465	Intermediate Similarity	NPD1164	Approved
0.745	Intermediate Similarity	NPD5405	Approved
0.745	Intermediate Similarity	NPD5404	Approved
0.745	Intermediate Similarity	NPD5406	Approved
0.745	Intermediate Similarity	NPD5408	Approved
0.7448	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD411	Approved
0.7448	Intermediate Similarity	NPD3764	Approved
0.7448	Intermediate Similarity	NPD3268	Approved
0.7421	Intermediate Similarity	NPD4288	Approved
0.7415	Intermediate Similarity	NPD447	Suspended
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3225	Approved
0.7379	Intermediate Similarity	NPD3027	Phase 3
0.7376	Intermediate Similarity	NPD9269	Phase 2
0.7372	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD9268	Approved
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1296	Phase 2
0.7325	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD3751	Discontinued
0.7286	Intermediate Similarity	NPD17	Approved
0.7279	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD1876	Approved
0.7257	Intermediate Similarity	NPD4363	Phase 3
0.7257	Intermediate Similarity	NPD4360	Phase 2
0.7241	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4307	Phase 2
0.7222	Intermediate Similarity	NPD3267	Approved
0.7222	Intermediate Similarity	NPD3266	Approved
0.7216	Intermediate Similarity	NPD4361	Phase 2
0.7216	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4749	Approved
0.7202	Intermediate Similarity	NPD1729	Discontinued
0.7188	Intermediate Similarity	NPD6844	Discontinued
0.7188	Intermediate Similarity	NPD37	Approved
0.7181	Intermediate Similarity	NPD1933	Approved
0.7175	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1019	Discontinued
0.7171	Intermediate Similarity	NPD1471	Phase 3
0.7164	Intermediate Similarity	NPD9266	Approved
0.7164	Intermediate Similarity	NPD74	Approved
0.7153	Intermediate Similarity	NPD1283	Approved
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD7003	Approved
0.7126	Intermediate Similarity	NPD4287	Approved
0.7123	Intermediate Similarity	NPD2861	Phase 2
0.7099	Intermediate Similarity	NPD2296	Approved
0.7097	Intermediate Similarity	NPD6190	Approved
0.7095	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1651	Approved
0.7091	Intermediate Similarity	NPD7199	Phase 2
0.709	Intermediate Similarity	NPD9264	Approved
0.709	Intermediate Similarity	NPD9263	Approved
0.709	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9267	Approved
0.7073	Intermediate Similarity	NPD6234	Discontinued
0.7067	Intermediate Similarity	NPD5124	Phase 1
0.7067	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4965	Approved
0.7055	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4967	Phase 2
0.7055	Intermediate Similarity	NPD4966	Approved
0.7048	Intermediate Similarity	NPD3787	Discontinued
0.7048	Intermediate Similarity	NPD7229	Phase 3
0.7044	Intermediate Similarity	NPD1653	Approved
0.7035	Intermediate Similarity	NPD8312	Approved
0.7035	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1242	Phase 1
0.7019	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6104	Discontinued
0.7014	Intermediate Similarity	NPD1481	Phase 2
0.7012	Intermediate Similarity	NPD6971	Discontinued
0.7006	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6798	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data