NPASS Compound

Structure

CID85131 OpenBabel06191715422D 26 28 0 0 0 0 0 0 0 0999 V2000 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -2.5981 -0.5000 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 -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 -0.0000 3.0000 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 -1.7321 1.0000 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 -3.4641 1.0000 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 -2.5981 1.5000 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 3.4641 -2.0000 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 1.7321 1.0000 0.0000 O 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 -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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 4 1 0 0 0 0 3 10 2 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 17 2 0 0 0 0 9 14 2 0 0 0 0 9 26 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	357.82
LogP:	4.201
LogD:	2.74
LogS:	-3.469
# Rotatable Bonds:	3
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	2.905
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.942
MDCK Permeability:	9.244983630196657e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.66
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.2624282836914%
Volume Distribution (VD):	0.605
Pgp-substrate:	4.68583869934082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.925
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.67
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.795
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.875
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	8.534
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.474
AMES Toxicity:	0.131
Rat Oral Acute Toxicity:	0.354
Maximum Recommended Daily Dose:	0.184
Skin Sensitization:	0.946
Carcinogencity:	0.142
Eye Corrosion:	0.004
Eye Irritation:	0.902
Respiratory Toxicity:	0.115

Download Data

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

Natural Product: NPC85131

Natural Product ID:	NPC85131
*Common Name:**	5,7,3',4'-Tetrahydroxy-2'-(3,3-Dimethylallyl)Isoflavone
IUPAC Name:	3-[3,4-dihydroxy-2-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	XIUMMQJDWWYGHD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O6/c1-10(2)3-4-13-12(5-6-15(22)19(13)24)14-9-26-17-8-11(21)7-16(23)18(17)20(14)25/h3,5-9,21-24H,4H2,1-2H3
SMILES:	CC(=CCc1c(ccc(c1O)O)c1coc2cc(cc(c2c1=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491480
PubChem CID:	11610052
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones [CHEMONTID:0003580] 2'-prenylated 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
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	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	4

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	37500.0	nM	PMID[485025]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	12700.0	nM	PMID[485025]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	13000.0	nM	PMID[485025]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	12100.0	nM	PMID[485025]

☑ 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 NPC85131 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	416
0.1-0.2	1806
0.2-0.3	4323
0.3-0.4	11108
0.4-0.5	6886
0.5-0.6	3498
0.6-0.7	5098
0.7-0.8	5198
0.8-0.85	2537
0.85-0.9	1362
0.9-0.95	428
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
0.966	High Similarity	NPC93552
0.9655	High Similarity	NPC38545
0.9655	High Similarity	NPC171916
0.9592	High Similarity	NPC474993
0.9586	High Similarity	NPC80710
0.9586	High Similarity	NPC139364
0.9586	High Similarity	NPC254702
0.9586	High Similarity	NPC203747
0.9586	High Similarity	NPC238279
0.9586	High Similarity	NPC166036
0.9586	High Similarity	NPC194653
0.9586	High Similarity	NPC203077
0.958	High Similarity	NPC38065
0.958	High Similarity	NPC242893
0.9524	High Similarity	NPC256406
0.9521	High Similarity	NPC264550
0.9521	High Similarity	NPC195763
0.9521	High Similarity	NPC40290
0.9521	High Similarity	NPC264289
0.9521	High Similarity	NPC200060
0.9521	High Similarity	NPC142876
0.9521	High Similarity	NPC333691
0.9521	High Similarity	NPC69430
0.9521	High Similarity	NPC139293
0.951	High Similarity	NPC471417
0.947	High Similarity	NPC474960
0.9463	High Similarity	NPC67396
0.9459	High Similarity	NPC323626
0.9459	High Similarity	NPC324233
0.9456	High Similarity	NPC10467
0.9448	High Similarity	NPC12377
0.9441	High Similarity	NPC284556
0.9441	High Similarity	NPC301178
0.94	High Similarity	NPC24640
0.9396	High Similarity	NPC124714
0.9384	High Similarity	NPC125449
0.9384	High Similarity	NPC188074
0.9375	High Similarity	NPC287722
0.9338	High Similarity	NPC472963
0.9333	High Similarity	NPC56786
0.9333	High Similarity	NPC80534
0.9329	High Similarity	NPC131266
0.9329	High Similarity	NPC100971
0.9329	High Similarity	NPC209487
0.9329	High Similarity	NPC291802
0.9329	High Similarity	NPC269451
0.9329	High Similarity	NPC100263
0.9329	High Similarity	NPC216769
0.9329	High Similarity	NPC35763
0.9329	High Similarity	NPC245382
0.9329	High Similarity	NPC121522
0.9329	High Similarity	NPC181209
0.932	High Similarity	NPC218490
0.9306	High Similarity	NPC49108
0.9276	High Similarity	NPC210459
0.9272	High Similarity	NPC282307
0.9272	High Similarity	NPC472907
0.9272	High Similarity	NPC170026
0.9267	High Similarity	NPC107109
0.9267	High Similarity	NPC469550
0.9267	High Similarity	NPC250557
0.9267	High Similarity	NPC472905
0.9262	High Similarity	NPC154345
0.9262	High Similarity	NPC45291
0.9262	High Similarity	NPC19980
0.9262	High Similarity	NPC262623
0.9257	High Similarity	NPC105512
0.9252	High Similarity	NPC108406
0.9252	High Similarity	NPC95864
0.9252	High Similarity	NPC474999
0.9241	High Similarity	NPC119663
0.9241	High Similarity	NPC254659
0.9226	High Similarity	NPC303174
0.9221	High Similarity	NPC472964
0.9216	High Similarity	NPC472902
0.9216	High Similarity	NPC36217
0.9216	High Similarity	NPC321399
0.9211	High Similarity	NPC199463
0.9211	High Similarity	NPC129684
0.9211	High Similarity	NPC299520
0.9211	High Similarity	NPC273843
0.9211	High Similarity	NPC37543
0.9211	High Similarity	NPC178976
0.9205	High Similarity	NPC39184
0.9205	High Similarity	NPC134287
0.9205	High Similarity	NPC130589
0.9205	High Similarity	NPC234255
0.9205	High Similarity	NPC38898
0.92	High Similarity	NPC477231
0.92	High Similarity	NPC472912
0.92	High Similarity	NPC60972
0.92	High Similarity	NPC149889
0.92	High Similarity	NPC312338
0.92	High Similarity	NPC260979
0.92	High Similarity	NPC257648
0.92	High Similarity	NPC39732
0.9195	High Similarity	NPC472279
0.9195	High Similarity	NPC239363
0.9195	High Similarity	NPC88804
0.9195	High Similarity	NPC156953
0.9195	High Similarity	NPC3825
0.9189	High Similarity	NPC3036
0.9189	High Similarity	NPC474903
0.9189	High Similarity	NPC119059
0.9184	High Similarity	NPC138978
0.9178	High Similarity	NPC105213
0.9178	High Similarity	NPC207732
0.9178	High Similarity	NPC142165
0.9172	High Similarity	NPC185607
0.9161	High Similarity	NPC209560
0.9161	High Similarity	NPC162680
0.9161	High Similarity	NPC294409
0.9161	High Similarity	NPC186686
0.9161	High Similarity	NPC181124
0.9161	High Similarity	NPC7013
0.9161	High Similarity	NPC116632
0.9161	High Similarity	NPC303644
0.9161	High Similarity	NPC212767
0.915	High Similarity	NPC74178
0.915	High Similarity	NPC184755
0.915	High Similarity	NPC329091
0.915	High Similarity	NPC85121
0.9145	High Similarity	NPC153512
0.9145	High Similarity	NPC5379
0.9145	High Similarity	NPC227062
0.9145	High Similarity	NPC13779
0.9145	High Similarity	NPC475799
0.9145	High Similarity	NPC472455
0.9145	High Similarity	NPC77807
0.9145	High Similarity	NPC14561
0.9139	High Similarity	NPC192083
0.9139	High Similarity	NPC18727
0.9139	High Similarity	NPC213896
0.9139	High Similarity	NPC89474
0.9133	High Similarity	NPC31363
0.9133	High Similarity	NPC78505
0.9133	High Similarity	NPC260895
0.9128	High Similarity	NPC287101
0.9128	High Similarity	NPC48479
0.9128	High Similarity	NPC52005
0.9128	High Similarity	NPC183950
0.9128	High Similarity	NPC87125
0.9128	High Similarity	NPC177298
0.9128	High Similarity	NPC137062
0.9128	High Similarity	NPC183959
0.9128	High Similarity	NPC1612
0.9128	High Similarity	NPC270465
0.9128	High Similarity	NPC102003
0.9128	High Similarity	NPC223579
0.9128	High Similarity	NPC92722
0.9116	High Similarity	NPC157133
0.9116	High Similarity	NPC70136
0.9103	High Similarity	NPC110419
0.9103	High Similarity	NPC80962
0.9103	High Similarity	NPC172250
0.9103	High Similarity	NPC472904
0.9103	High Similarity	NPC215311
0.9103	High Similarity	NPC144118
0.9103	High Similarity	NPC326109
0.9103	High Similarity	NPC219917
0.9103	High Similarity	NPC48624
0.9103	High Similarity	NPC204985
0.9103	High Similarity	NPC213659
0.9103	High Similarity	NPC259166
0.9097	High Similarity	NPC12175
0.9097	High Similarity	NPC472368
0.9097	High Similarity	NPC309154
0.9097	High Similarity	NPC55162
0.9097	High Similarity	NPC90665
0.9097	High Similarity	NPC279668
0.9097	High Similarity	NPC278323
0.9097	High Similarity	NPC201800
0.9097	High Similarity	NPC329760
0.9091	High Similarity	NPC472367
0.9091	High Similarity	NPC290030
0.9091	High Similarity	NPC328102
0.9091	High Similarity	NPC193792
0.9091	High Similarity	NPC471973
0.9091	High Similarity	NPC28241
0.9091	High Similarity	NPC473391
0.9091	High Similarity	NPC297212
0.9091	High Similarity	NPC472364
0.9091	High Similarity	NPC476333
0.9091	High Similarity	NPC476283
0.9085	High Similarity	NPC300727
0.9085	High Similarity	NPC67876
0.9085	High Similarity	NPC136674
0.9085	High Similarity	NPC78103
0.9085	High Similarity	NPC52889
0.9085	High Similarity	NPC291508
0.9085	High Similarity	NPC241904
0.9085	High Similarity	NPC111969
0.9079	High Similarity	NPC152951
0.9079	High Similarity	NPC256612
0.9079	High Similarity	NPC213622
0.9079	High Similarity	NPC472280
0.9079	High Similarity	NPC168247
0.9079	High Similarity	NPC133392
0.9079	High Similarity	NPC57674
0.9079	High Similarity	NPC321779

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 NPC85131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	975
0.2-0.3	1667
0.3-0.4	2673
0.4-0.5	1818
0.5-0.6	1025
0.6-0.7	420
0.7-0.8	116
0.8-0.85	43
0.85-0.9	16
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9139	High Similarity	NPD2393	Clinical (unspecified phase)
0.9073	High Similarity	NPD1934	Approved
0.9048	High Similarity	NPD1511	Approved
0.9021	High Similarity	NPD1510	Phase 2
0.9013	High Similarity	NPD2801	Approved
0.8926	High Similarity	NPD1512	Approved
0.8896	High Similarity	NPD3882	Suspended
0.8741	High Similarity	NPD1240	Approved
0.8693	High Similarity	NPD4380	Phase 2
0.8645	High Similarity	NPD7819	Suspended
0.8634	High Similarity	NPD3818	Discontinued
0.8625	High Similarity	NPD6167	Clinical (unspecified phase)
0.8625	High Similarity	NPD6166	Phase 2
0.8625	High Similarity	NPD6168	Clinical (unspecified phase)
0.8621	High Similarity	NPD1607	Approved
0.8616	High Similarity	NPD6232	Discontinued
0.8611	High Similarity	NPD943	Approved
0.8609	High Similarity	NPD4378	Clinical (unspecified phase)
0.859	High Similarity	NPD3817	Phase 2
0.8581	High Similarity	NPD1549	Phase 2
0.8581	High Similarity	NPD970	Clinical (unspecified phase)
0.8571	High Similarity	NPD7473	Discontinued
0.8571	High Similarity	NPD2796	Approved
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7054	Approved
0.8418	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7472	Approved
0.8415	Intermediate Similarity	NPD7074	Phase 3
0.8366	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7075	Discontinued
0.8364	Intermediate Similarity	NPD6797	Phase 2
0.8344	Intermediate Similarity	NPD3750	Approved
0.8313	Intermediate Similarity	NPD7251	Discontinued
0.8301	Intermediate Similarity	NPD6799	Approved
0.8291	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5494	Approved
0.8255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6801	Discontinued
0.8217	Intermediate Similarity	NPD6599	Discontinued
0.821	Intermediate Similarity	NPD6959	Discontinued
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8165	Intermediate Similarity	NPD7411	Suspended
0.8155	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7808	Phase 3
0.8133	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5844	Phase 1
0.8129	Intermediate Similarity	NPD2533	Approved
0.8129	Intermediate Similarity	NPD2532	Approved
0.8129	Intermediate Similarity	NPD2534	Approved
0.8079	Intermediate Similarity	NPD2935	Discontinued
0.8054	Intermediate Similarity	NPD230	Phase 1
0.8025	Intermediate Similarity	NPD3749	Approved
0.8025	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3748	Approved
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7768	Phase 2
0.7952	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5403	Approved
0.7905	Intermediate Similarity	NPD3027	Phase 3
0.7901	Intermediate Similarity	NPD5402	Approved
0.7892	Intermediate Similarity	NPD3926	Phase 2
0.7866	Intermediate Similarity	NPD919	Approved
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.7834	Intermediate Similarity	NPD7390	Discontinued
0.7823	Intermediate Similarity	NPD2798	Approved
0.7806	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5401	Approved
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD1247	Approved
0.7771	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD9494	Approved
0.7763	Intermediate Similarity	NPD6651	Approved
0.7758	Intermediate Similarity	NPD6234	Discontinued
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7748	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1613	Approved
0.774	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD2800	Approved
0.768	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2344	Approved
0.7673	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD37	Approved
0.7651	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1470	Approved
0.763	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1201	Approved
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1243	Approved
0.7578	Intermediate Similarity	NPD920	Approved
0.7564	Intermediate Similarity	NPD2346	Discontinued
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3751	Discontinued
0.753	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD4965	Approved
0.7515	Intermediate Similarity	NPD5711	Approved
0.7515	Intermediate Similarity	NPD5710	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7484	Intermediate Similarity	NPD6190	Approved
0.7484	Intermediate Similarity	NPD2309	Approved
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7468	Intermediate Similarity	NPD447	Suspended
0.7453	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7228	Approved
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7432	Intermediate Similarity	NPD3972	Approved
0.7421	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3787	Discontinued
0.74	Intermediate Similarity	NPD1203	Approved
0.7399	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3764	Approved
0.7386	Intermediate Similarity	NPD3268	Approved
0.7386	Intermediate Similarity	NPD2313	Discontinued
0.7378	Intermediate Similarity	NPD7458	Discontinued
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7368	Intermediate Similarity	NPD5242	Approved
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4288	Approved
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.7358	Intermediate Similarity	NPD2654	Approved
0.7355	Intermediate Similarity	NPD1933	Approved
0.7333	Intermediate Similarity	NPD1876	Approved
0.7329	Intermediate Similarity	NPD1548	Phase 1
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.732	Intermediate Similarity	NPD4625	Phase 3
0.7317	Intermediate Similarity	NPD1653	Approved
0.7312	Intermediate Similarity	NPD7003	Approved
0.7312	Intermediate Similarity	NPD8166	Discontinued
0.7297	Intermediate Similarity	NPD6776	Approved
0.7297	Intermediate Similarity	NPD6781	Approved
0.7297	Intermediate Similarity	NPD6777	Approved
0.7297	Intermediate Similarity	NPD6782	Approved
0.7297	Intermediate Similarity	NPD6778	Approved
0.7297	Intermediate Similarity	NPD6779	Approved
0.7297	Intermediate Similarity	NPD6780	Approved
0.7288	Intermediate Similarity	NPD8312	Approved
0.7288	Intermediate Similarity	NPD8313	Approved
0.7285	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8151	Discontinued
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.726	Intermediate Similarity	NPD5536	Phase 2
0.7244	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7213	Intermediate Similarity	NPD4363	Phase 3
0.7213	Intermediate Similarity	NPD4360	Phase 2
0.7211	Intermediate Similarity	NPD9545	Approved
0.7209	Intermediate Similarity	NPD7229	Phase 3
0.72	Intermediate Similarity	NPD1608	Approved
0.72	Intermediate Similarity	NPD9717	Approved
0.7192	Intermediate Similarity	NPD9493	Approved
0.7192	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3018	Phase 2
0.7181	Intermediate Similarity	NPD7435	Discontinued
0.7179	Intermediate Similarity	NPD4060	Phase 1
0.7178	Intermediate Similarity	NPD4357	Discontinued
0.7174	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4361	Phase 2
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7162	Intermediate Similarity	NPD1651	Approved
0.7162	Intermediate Similarity	NPD9268	Approved
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7125	Intermediate Similarity	NPD1471	Phase 3
0.7117	Intermediate Similarity	NPD3300	Phase 2
0.7105	Intermediate Similarity	NPD1283	Approved
0.7091	Intermediate Similarity	NPD6273	Approved
0.709	Intermediate Similarity	NPD7696	Phase 3
0.709	Intermediate Similarity	NPD7697	Approved
0.709	Intermediate Similarity	NPD7698	Approved
0.7088	Intermediate Similarity	NPD4287	Approved
0.7083	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD6385	Approved
0.7079	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5977	Approved
0.7059	Intermediate Similarity	NPD3267	Approved
0.7059	Intermediate Similarity	NPD3266	Approved
0.7059	Intermediate Similarity	NPD1164	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