NPASS Compound

Structure

CID101366 OpenBabel06191715442D 22 24 0 0 0 0 0 0 0 0999 V2000 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -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 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 2.5981 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 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 -2.5981 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 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 -0.0000 -0.0000 0.0000 C 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 -2.5981 1.5000 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 9 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 2 0 0 0 0 6 13 2 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	3.24
LogD:	2.59
LogS:	-3.346
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	2.381
Fsp3:	0.118
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:	-4.836
MDCK Permeability:	1.680144305282738e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.919
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	98.48841094970703%
Volume Distribution (VD):	0.385
Pgp-substrate:	2.3418474197387695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.896
CYP2C19-inhibitor:	0.808
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.821
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.755
CYP2D6-substrate:	0.762
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	5.433
Half-life (T1/2):	0.675

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.663
AMES Toxicity:	0.174
Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.198
Skin Sensitization:	0.846
Carcinogencity:	0.24
Eye Corrosion:	0.018
Eye Irritation:	0.94
Respiratory Toxicity:	0.163

Download Data

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

Natural Product: NPC101366

Natural Product ID:	NPC101366
*Common Name:**	2'-O-Methylabronisoflavone
IUPAC Name:	5,7-dihydroxy-3-(2-methoxyphenyl)-6-methylchromen-4-one
Synonyms:	2'-O-Methylabronisoflavone
Standard InCHIKey:	MNTFQBBYPKFUJE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-9-12(18)7-14-15(16(9)19)17(20)11(8-22-14)10-5-3-4-6-13(10)21-2/h3-8,18-19H,1-2H3
SMILES:	Cc1c(cc2c(c1O)c(=O)c(co2)c1ccccc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496643
PubChem CID:	5482494
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
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277746]
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[16792408]
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23914900]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Organism	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	25.0	ug.mL-1	PMID[448930]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	16.0	ug.mL-1	PMID[448930]
NPT548	Tissue	Ileum	Cavia porcellus	Emax	=	36.8	%	PMID[448931]

☑ 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 NPC101366 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	421
0.1-0.2	1824
0.2-0.3	4193
0.3-0.4	10634
0.4-0.5	7592
0.5-0.6	3907
0.6-0.7	5603
0.7-0.8	4390
0.8-0.85	1942
0.85-0.9	1647
0.9-0.95	454
0.95-1	90

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC52789
0.9926	High Similarity	NPC26051
0.9926	High Similarity	NPC55832
0.9926	High Similarity	NPC268204
0.9925	High Similarity	NPC295384
0.9852	High Similarity	NPC219917
0.9852	High Similarity	NPC213659
0.9852	High Similarity	NPC48624
0.9852	High Similarity	NPC204985
0.9852	High Similarity	NPC259166
0.9852	High Similarity	NPC253822
0.9852	High Similarity	NPC80962
0.9852	High Similarity	NPC172250
0.9852	High Similarity	NPC326109
0.9852	High Similarity	NPC144118
0.9852	High Similarity	NPC215311
0.9851	High Similarity	NPC12175
0.9851	High Similarity	NPC90665
0.9851	High Similarity	NPC309154
0.9851	High Similarity	NPC55162
0.9851	High Similarity	NPC279668
0.9851	High Similarity	NPC278323
0.9779	High Similarity	NPC469404
0.9778	High Similarity	NPC283429
0.9776	High Similarity	NPC181124
0.9776	High Similarity	NPC209560
0.9776	High Similarity	NPC162680
0.9776	High Similarity	NPC7013
0.9776	High Similarity	NPC294409
0.9776	High Similarity	NPC303644
0.9776	High Similarity	NPC116632
0.971	High Similarity	NPC476055
0.9701	High Similarity	NPC235428
0.9701	High Similarity	NPC87545
0.9638	High Similarity	NPC476178
0.9638	High Similarity	NPC51887
0.9638	High Similarity	NPC117836
0.9638	High Similarity	NPC475705
0.9632	High Similarity	NPC477956
0.963	High Similarity	NPC472419
0.9627	High Similarity	NPC39426
0.9627	High Similarity	NPC234560
0.9568	High Similarity	NPC234629
0.9568	High Similarity	NPC311741
0.9559	High Similarity	NPC21350
0.9556	High Similarity	NPC98115
0.9556	High Similarity	NPC1486
0.9556	High Similarity	NPC186838
0.9556	High Similarity	NPC477242
0.9556	High Similarity	NPC168105
0.9556	High Similarity	NPC66349
0.9556	High Similarity	NPC274109
0.9556	High Similarity	NPC477244
0.9556	High Similarity	NPC477243
0.9556	High Similarity	NPC12165
0.9556	High Similarity	NPC150399
0.9556	High Similarity	NPC41461
0.9556	High Similarity	NPC25287
0.9556	High Similarity	NPC249606
0.9504	High Similarity	NPC266572
0.9493	High Similarity	NPC470087
0.9493	High Similarity	NPC321980
0.9493	High Similarity	NPC110969
0.9493	High Similarity	NPC470089
0.9493	High Similarity	NPC3188
0.9489	High Similarity	NPC470211
0.9489	High Similarity	NPC18260
0.9489	High Similarity	NPC78913
0.9485	High Similarity	NPC317119
0.9485	High Similarity	NPC153979
0.9485	High Similarity	NPC212767
0.9481	High Similarity	NPC131039
0.9481	High Similarity	NPC156092
0.9481	High Similarity	NPC13575
0.9437	High Similarity	NPC317492
0.9433	High Similarity	NPC237635
0.9433	High Similarity	NPC104406
0.9433	High Similarity	NPC97716
0.9433	High Similarity	NPC222298
0.9433	High Similarity	NPC201731
0.9433	High Similarity	NPC79469
0.9433	High Similarity	NPC24673
0.9433	High Similarity	NPC51070
0.9424	High Similarity	NPC226636
0.9424	High Similarity	NPC11561
0.942	High Similarity	NPC159275
0.942	High Similarity	NPC172986
0.942	High Similarity	NPC270883
0.942	High Similarity	NPC261227
0.942	High Similarity	NPC241100
0.942	High Similarity	NPC11056
0.9416	High Similarity	NPC471620
0.9416	High Similarity	NPC251681
0.9416	High Similarity	NPC243528
0.9416	High Similarity	NPC201395
0.9412	High Similarity	NPC193792
0.9407	High Similarity	NPC103842
0.9407	High Similarity	NPC286336
0.9403	High Similarity	NPC212631
0.9403	High Similarity	NPC205468
0.9403	High Similarity	NPC129132
0.9403	High Similarity	NPC257756
0.9403	High Similarity	NPC87231
0.9403	High Similarity	NPC182428
0.9366	High Similarity	NPC168085
0.9366	High Similarity	NPC6511
0.9366	High Similarity	NPC39195
0.9357	High Similarity	NPC169591
0.9357	High Similarity	NPC39329
0.9357	High Similarity	NPC149026
0.9357	High Similarity	NPC257097
0.9357	High Similarity	NPC310130
0.9357	High Similarity	NPC150408
0.9357	High Similarity	NPC106985
0.9357	High Similarity	NPC68104
0.9357	High Similarity	NPC166138
0.9357	High Similarity	NPC301751
0.9357	High Similarity	NPC18585
0.9357	High Similarity	NPC91560
0.9357	High Similarity	NPC143896
0.9357	High Similarity	NPC75049
0.9357	High Similarity	NPC221432
0.9357	High Similarity	NPC164980
0.9357	High Similarity	NPC175504
0.9357	High Similarity	NPC245482
0.9353	High Similarity	NPC4743
0.9353	High Similarity	NPC213322
0.9353	High Similarity	NPC147688
0.9353	High Similarity	NPC103362
0.9353	High Similarity	NPC205006
0.9353	High Similarity	NPC118840
0.9353	High Similarity	NPC312391
0.9353	High Similarity	NPC64908
0.9353	High Similarity	NPC282300
0.9353	High Similarity	NPC156590
0.9353	High Similarity	NPC324386
0.9348	High Similarity	NPC472366
0.9348	High Similarity	NPC96565
0.9348	High Similarity	NPC301217
0.9348	High Similarity	NPC220062
0.9348	High Similarity	NPC216978
0.9348	High Similarity	NPC303633
0.9348	High Similarity	NPC217186
0.9348	High Similarity	NPC53181
0.9348	High Similarity	NPC55018
0.9343	High Similarity	NPC266597
0.9343	High Similarity	NPC228661
0.9343	High Similarity	NPC250266
0.9333	High Similarity	NPC56031
0.9333	High Similarity	NPC192304
0.9333	High Similarity	NPC139813
0.9333	High Similarity	NPC159623
0.9333	High Similarity	NPC337373
0.9333	High Similarity	NPC188646
0.9333	High Similarity	NPC175098
0.9333	High Similarity	NPC82225
0.9333	High Similarity	NPC472365
0.9333	High Similarity	NPC27643
0.9333	High Similarity	NPC28753
0.9333	High Similarity	NPC20560
0.9333	High Similarity	NPC144051
0.9333	High Similarity	NPC263670
0.9333	High Similarity	NPC294593
0.9333	High Similarity	NPC242294
0.9333	High Similarity	NPC18877
0.9333	High Similarity	NPC223354
0.9333	High Similarity	NPC312318
0.9333	High Similarity	NPC204960
0.9328	High Similarity	NPC313618
0.9328	High Similarity	NPC64359
0.9328	High Similarity	NPC308037
0.9328	High Similarity	NPC262359
0.9301	High Similarity	NPC38545
0.9301	High Similarity	NPC171916
0.9296	High Similarity	NPC473077
0.9296	High Similarity	NPC23728
0.9296	High Similarity	NPC308200
0.9296	High Similarity	NPC296998
0.9296	High Similarity	NPC110303
0.9291	High Similarity	NPC319752
0.9291	High Similarity	NPC236766
0.9291	High Similarity	NPC473013
0.9291	High Similarity	NPC197252
0.9291	High Similarity	NPC473015
0.9291	High Similarity	NPC209040
0.9291	High Similarity	NPC273538
0.9291	High Similarity	NPC224714
0.9291	High Similarity	NPC184649
0.9291	High Similarity	NPC271288
0.9291	High Similarity	NPC216538
0.9291	High Similarity	NPC303185
0.9286	High Similarity	NPC32739
0.9286	High Similarity	NPC473042
0.9286	High Similarity	NPC306829
0.9286	High Similarity	NPC78
0.9286	High Similarity	NPC66515
0.9286	High Similarity	NPC166482
0.9286	High Similarity	NPC194432
0.9286	High Similarity	NPC265040
0.9286	High Similarity	NPC202981

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 NPC101366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	974
0.2-0.3	1581
0.3-0.4	2633
0.4-0.5	1902
0.5-0.6	1116
0.6-0.7	356
0.7-0.8	111
0.8-0.85	41
0.85-0.9	26
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9627	High Similarity	NPD1510	Phase 2
0.9328	High Similarity	NPD1240	Approved
0.9291	High Similarity	NPD4378	Clinical (unspecified phase)
0.9191	High Similarity	NPD1607	Approved
0.9137	High Similarity	NPD1549	Phase 2
0.9103	High Similarity	NPD4380	Phase 2
0.9065	High Similarity	NPD1550	Clinical (unspecified phase)
0.9065	High Similarity	NPD1552	Clinical (unspecified phase)
0.9021	High Similarity	NPD7410	Clinical (unspecified phase)
0.8993	High Similarity	NPD2796	Approved
0.8792	High Similarity	NPD2393	Clinical (unspecified phase)
0.8784	High Similarity	NPD7411	Suspended
0.8742	High Similarity	NPD7075	Discontinued
0.8733	High Similarity	NPD8443	Clinical (unspecified phase)
0.8667	High Similarity	NPD7819	Suspended
0.8667	High Similarity	NPD7096	Clinical (unspecified phase)
0.8611	High Similarity	NPD1878	Clinical (unspecified phase)
0.86	High Similarity	NPD6801	Discontinued
0.86	High Similarity	NPD1934	Approved
0.8562	High Similarity	NPD1511	Approved
0.8543	High Similarity	NPD2801	Approved
0.8497	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD3750	Approved
0.8472	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD2935	Discontinued
0.8446	Intermediate Similarity	NPD1512	Approved
0.8435	Intermediate Similarity	NPD6799	Approved
0.8431	Intermediate Similarity	NPD7768	Phase 2
0.8431	Intermediate Similarity	NPD3882	Suspended
0.8414	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD2800	Approved
0.8408	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD920	Approved
0.838	Intermediate Similarity	NPD6651	Approved
0.8333	Intermediate Similarity	NPD1551	Phase 2
0.8288	Intermediate Similarity	NPD1243	Approved
0.828	Intermediate Similarity	NPD6232	Discontinued
0.8258	Intermediate Similarity	NPD3749	Approved
0.8255	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2533	Approved
0.8255	Intermediate Similarity	NPD2534	Approved
0.8255	Intermediate Similarity	NPD2532	Approved
0.825	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD943	Approved
0.8239	Intermediate Similarity	NPD7473	Discontinued
0.8227	Intermediate Similarity	NPD2313	Discontinued
0.8224	Intermediate Similarity	NPD6599	Discontinued
0.8217	Intermediate Similarity	NPD6959	Discontinued
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8153	Intermediate Similarity	NPD5494	Approved
0.8151	Intermediate Similarity	NPD2344	Approved
0.8148	Intermediate Similarity	NPD5953	Discontinued
0.8138	Intermediate Similarity	NPD2799	Discontinued
0.8138	Intermediate Similarity	NPD3748	Approved
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD2798	Approved
0.8063	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6166	Phase 2
0.8063	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD7286	Phase 2
0.8013	Intermediate Similarity	NPD5401	Approved
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2309	Approved
0.7922	Intermediate Similarity	NPD3226	Approved
0.7914	Intermediate Similarity	NPD7054	Approved
0.7898	Intermediate Similarity	NPD5402	Approved
0.7879	Intermediate Similarity	NPD6559	Discontinued
0.7875	Intermediate Similarity	NPD1247	Approved
0.7872	Intermediate Similarity	NPD1203	Approved
0.7866	Intermediate Similarity	NPD7472	Approved
0.7866	Intermediate Similarity	NPD7074	Phase 3
0.7862	Intermediate Similarity	NPD919	Approved
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7390	Discontinued
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.781	Intermediate Similarity	NPD1548	Phase 1
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD1470	Approved
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1610	Phase 2
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7708	Intermediate Similarity	NPD6832	Phase 2
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7692	Intermediate Similarity	NPD7458	Discontinued
0.7687	Intermediate Similarity	NPD230	Phase 1
0.7682	Intermediate Similarity	NPD2654	Approved
0.7681	Intermediate Similarity	NPD9545	Approved
0.7677	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD9493	Approved
0.766	Intermediate Similarity	NPD9717	Approved
0.766	Intermediate Similarity	NPD3972	Approved
0.7651	Intermediate Similarity	NPD7033	Discontinued
0.7651	Intermediate Similarity	NPD4308	Phase 3
0.7622	Intermediate Similarity	NPD1164	Approved
0.7607	Intermediate Similarity	NPD5710	Approved
0.7607	Intermediate Similarity	NPD5711	Approved
0.7603	Intermediate Similarity	NPD3764	Approved
0.7603	Intermediate Similarity	NPD3268	Approved
0.76	Intermediate Similarity	NPD6100	Approved
0.76	Intermediate Similarity	NPD6099	Approved
0.7589	Intermediate Similarity	NPD1201	Approved
0.7589	Intermediate Similarity	NPD422	Phase 1
0.7586	Intermediate Similarity	NPD4360	Phase 2
0.7586	Intermediate Similarity	NPD4363	Phase 3
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.7543	Intermediate Similarity	NPD4361	Phase 2
0.7543	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7003	Approved
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5404	Approved
0.7483	Intermediate Similarity	NPD5408	Approved
0.7483	Intermediate Similarity	NPD5406	Approved
0.7483	Intermediate Similarity	NPD5405	Approved
0.7471	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4288	Approved
0.745	Intermediate Similarity	NPD5124	Phase 1
0.745	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1729	Discontinued
0.7434	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3225	Approved
0.7431	Intermediate Similarity	NPD1876	Approved
0.7397	Intermediate Similarity	NPD9494	Approved
0.7383	Intermediate Similarity	NPD4307	Phase 2
0.7379	Intermediate Similarity	NPD3267	Approved
0.7379	Intermediate Similarity	NPD3266	Approved
0.7374	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2296	Approved
0.7333	Intermediate Similarity	NPD1933	Approved
0.7333	Intermediate Similarity	NPD447	Suspended
0.732	Intermediate Similarity	NPD1471	Phase 3
0.7319	Intermediate Similarity	NPD1241	Discontinued
0.7297	Intermediate Similarity	NPD4625	Phase 3
0.7297	Intermediate Similarity	NPD3027	Phase 3
0.7292	Intermediate Similarity	NPD1608	Approved
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7267	Intermediate Similarity	NPD5889	Approved
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5890	Approved
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4287	Approved
0.7254	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD411	Approved
0.7248	Intermediate Similarity	NPD1296	Phase 2
0.723	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7584	Approved
0.7222	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD6844	Discontinued
0.7219	Intermediate Similarity	NPD3751	Discontinued
0.7219	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1019	Discontinued
0.7192	Intermediate Similarity	NPD1283	Approved
0.7182	Intermediate Similarity	NPD6777	Approved
0.7182	Intermediate Similarity	NPD6781	Approved
0.7182	Intermediate Similarity	NPD6778	Approved
0.7182	Intermediate Similarity	NPD6776	Approved
0.7182	Intermediate Similarity	NPD6780	Approved
0.7182	Intermediate Similarity	NPD6782	Approved
0.7182	Intermediate Similarity	NPD6779	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7163	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6104	Discontinued
0.7134	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD1651	Approved
0.7123	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6280	Approved
0.7117	Intermediate Similarity	NPD6279	Approved
0.7108	Intermediate Similarity	NPD6234	Discontinued
0.7107	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6585	Discontinued
0.7091	Intermediate Similarity	NPD4966	Approved
0.7091	Intermediate Similarity	NPD4967	Phase 2
0.7091	Intermediate Similarity	NPD4965	Approved
0.7083	Intermediate Similarity	NPD17	Approved
0.708	Intermediate Similarity	NPD74	Approved
0.708	Intermediate Similarity	NPD9266	Approved
0.7073	Intermediate Similarity	NPD5761	Phase 2

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