NPASS Compound

Structure

CID156953 OpenBabel06191715522D 23 25 0 0 0 0 0 0 0 0999 V2000 1.7321 2.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 23 1 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	2.825
LogD:	2.67
LogS:	-3.535
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	2.303
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:	-4.715
MDCK Permeability:	1.6568768842262216e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	93.81884002685547%
Volume Distribution (VD):	0.471
Pgp-substrate:	6.528829097747803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.891
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.689
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.522
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.76
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	8.828
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.712
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.656
Skin Sensitization:	0.659
Carcinogencity:	0.136
Eye Corrosion:	0.006
Eye Irritation:	0.815
Respiratory Toxicity:	0.246

Download Data

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

Natural Product: NPC156953

Natural Product ID:	NPC156953
*Common Name:**	7,2'-Dihydroxy-4',5'-Dimethoxyisoflavone
IUPAC Name:	7-hydroxy-3-(2-hydroxy-4,5-dimethoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	UYOJEKMKWXYOEQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-21-15-6-11(13(19)7-16(15)22-2)12-8-23-14-5-9(18)3-4-10(14)17(12)20/h3-8,18-19H,1-2H3
SMILES:	COc1cc(c2coc3cc(ccc3c2=O)O)c(cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL430186
PubChem CID:	5316763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-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
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	stem	n.a.	PMID[17077549]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	stems	n.a.	n.a.	PMID[17158054]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19829679]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[21087019]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22314230]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23521110]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834167]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22420	Lignum dalbergiae odoriferae rosewood	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100000.0	nM	PMID[561407]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	72000.0	nM	PMID[561407]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	48000.0	nM	PMID[561407]

☑ 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 NPC156953 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	458
0.1-0.2	1933
0.2-0.3	4735
0.3-0.4	11321
0.4-0.5	6273
0.5-0.6	3773
0.6-0.7	5148
0.7-0.8	4958
0.8-0.85	2146
0.85-0.9	1202
0.9-0.95	655
0.95-1	95

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC262623
0.9862	High Similarity	NPC209487
0.9862	High Similarity	NPC269451
0.9862	High Similarity	NPC181209
0.9862	High Similarity	NPC121522
0.9862	High Similarity	NPC131266
0.9862	High Similarity	NPC216769
0.9862	High Similarity	NPC35763
0.9862	High Similarity	NPC245382
0.9862	High Similarity	NPC100263
0.9862	High Similarity	NPC291802
0.9862	High Similarity	NPC100971
0.9861	High Similarity	NPC239363
0.9795	High Similarity	NPC124714
0.9793	High Similarity	NPC45291
0.9793	High Similarity	NPC19980
0.9728	High Similarity	NPC39184
0.9724	High Similarity	NPC10467
0.972	High Similarity	NPC12377
0.966	High Similarity	NPC280937
0.966	High Similarity	NPC250557
0.9655	High Similarity	NPC69430
0.9655	High Similarity	NPC40290
0.9655	High Similarity	NPC142876
0.9655	High Similarity	NPC195763
0.9655	High Similarity	NPC264550
0.9655	High Similarity	NPC264289
0.9655	High Similarity	NPC200060
0.9655	High Similarity	NPC139293
0.9655	High Similarity	NPC333691
0.9653	High Similarity	NPC93034
0.9653	High Similarity	NPC119660
0.9595	High Similarity	NPC134287
0.9595	High Similarity	NPC130589
0.9589	High Similarity	NPC306821
0.9586	High Similarity	NPC80710
0.9586	High Similarity	NPC183655
0.9586	High Similarity	NPC254702
0.9586	High Similarity	NPC287395
0.9586	High Similarity	NPC203747
0.9586	High Similarity	NPC139364
0.9586	High Similarity	NPC218490
0.9586	High Similarity	NPC194653
0.9583	High Similarity	NPC120924
0.9583	High Similarity	NPC216314
0.9583	High Similarity	NPC195919
0.9533	High Similarity	NPC62518
0.9533	High Similarity	NPC215375
0.9527	High Similarity	NPC472915
0.9524	High Similarity	NPC226973
0.9524	High Similarity	NPC117579
0.9524	High Similarity	NPC208043
0.9524	High Similarity	NPC308451
0.9524	High Similarity	NPC149614
0.9521	High Similarity	NPC92722
0.9521	High Similarity	NPC102003
0.9517	High Similarity	NPC125449
0.9517	High Similarity	NPC188074
0.9467	High Similarity	NPC99597
0.9467	High Similarity	NPC167595
0.9467	High Similarity	NPC210084
0.9467	High Similarity	NPC78103
0.9467	High Similarity	NPC181960
0.9467	High Similarity	NPC476981
0.9463	High Similarity	NPC213622
0.9463	High Similarity	NPC37392
0.9463	High Similarity	NPC20830
0.9463	High Similarity	NPC472909
0.9463	High Similarity	NPC256612
0.9463	High Similarity	NPC2928
0.9459	High Similarity	NPC241498
0.9459	High Similarity	NPC120163
0.9459	High Similarity	NPC83508
0.9459	High Similarity	NPC275836
0.9459	High Similarity	NPC301123
0.9459	High Similarity	NPC301323
0.9459	High Similarity	NPC212678
0.9459	High Similarity	NPC293183
0.9459	High Similarity	NPC162313
0.9459	High Similarity	NPC131624
0.9459	High Similarity	NPC57030
0.9459	High Similarity	NPC25270
0.9459	High Similarity	NPC222830
0.9459	High Similarity	NPC156222
0.9459	High Similarity	NPC239128
0.9459	High Similarity	NPC256283
0.9459	High Similarity	NPC187498
0.9459	High Similarity	NPC71334
0.9459	High Similarity	NPC198826
0.9459	High Similarity	NPC188203
0.9459	High Similarity	NPC100887
0.9459	High Similarity	NPC275722
0.9456	High Similarity	NPC179183
0.9452	High Similarity	NPC15329
0.9452	High Similarity	NPC131451
0.9448	High Similarity	NPC226987
0.9448	High Similarity	NPC143903
0.9444	High Similarity	NPC182842
0.9408	High Similarity	NPC295009
0.9408	High Similarity	NPC260640
0.94	High Similarity	NPC235165
0.94	High Similarity	NPC472916
0.94	High Similarity	NPC255106
0.9396	High Similarity	NPC271779
0.9396	High Similarity	NPC274327
0.9396	High Similarity	NPC183878
0.9396	High Similarity	NPC231018
0.9396	High Similarity	NPC86485
0.9396	High Similarity	NPC176775
0.9396	High Similarity	NPC88645
0.9396	High Similarity	NPC167091
0.9396	High Similarity	NPC292214
0.9396	High Similarity	NPC206238
0.9396	High Similarity	NPC47781
0.9396	High Similarity	NPC255350
0.9396	High Similarity	NPC69394
0.9396	High Similarity	NPC145379
0.9396	High Similarity	NPC22519
0.9396	High Similarity	NPC160951
0.9392	High Similarity	NPC256406
0.9388	High Similarity	NPC328119
0.9384	High Similarity	NPC12200
0.9375	High Similarity	NPC119663
0.9342	High Similarity	NPC225624
0.9342	High Similarity	NPC285973
0.9342	High Similarity	NPC476980
0.9338	High Similarity	NPC472910
0.9338	High Similarity	NPC470402
0.9338	High Similarity	NPC48208
0.9338	High Similarity	NPC222814
0.9338	High Similarity	NPC474208
0.9338	High Similarity	NPC474836
0.9338	High Similarity	NPC472914
0.9338	High Similarity	NPC96167
0.9338	High Similarity	NPC245758
0.9338	High Similarity	NPC156057
0.9338	High Similarity	NPC162869
0.9338	High Similarity	NPC472911
0.9338	High Similarity	NPC472913
0.9338	High Similarity	NPC475267
0.9333	High Similarity	NPC208197
0.9333	High Similarity	NPC92659
0.9333	High Similarity	NPC44079
0.9333	High Similarity	NPC255807
0.9333	High Similarity	NPC31018
0.9333	High Similarity	NPC167815
0.9333	High Similarity	NPC26227
0.9333	High Similarity	NPC189960
0.9333	High Similarity	NPC32557
0.9333	High Similarity	NPC128863
0.9333	High Similarity	NPC227325
0.9333	High Similarity	NPC163780
0.9333	High Similarity	NPC50715
0.9333	High Similarity	NPC2476
0.9333	High Similarity	NPC196439
0.9333	High Similarity	NPC201136
0.9333	High Similarity	NPC4455
0.9333	High Similarity	NPC280339
0.9333	High Similarity	NPC138360
0.9333	High Similarity	NPC183597
0.9333	High Similarity	NPC201451
0.9333	High Similarity	NPC146165
0.9329	High Similarity	NPC120537
0.9329	High Similarity	NPC39732
0.9329	High Similarity	NPC161277
0.9329	High Similarity	NPC142540
0.9329	High Similarity	NPC199100
0.9329	High Similarity	NPC60972
0.9329	High Similarity	NPC101996
0.9329	High Similarity	NPC474993
0.9329	High Similarity	NPC180234
0.9329	High Similarity	NPC39007
0.9324	High Similarity	NPC45873
0.9324	High Similarity	NPC184136
0.932	High Similarity	NPC195202
0.9315	High Similarity	NPC165389
0.931	High Similarity	NPC38065
0.931	High Similarity	NPC142165
0.931	High Similarity	NPC242893
0.9306	High Similarity	NPC185607
0.9281	High Similarity	NPC308992
0.9281	High Similarity	NPC258331
0.9276	High Similarity	NPC152904
0.9272	High Similarity	NPC245546
0.9272	High Similarity	NPC43243
0.9272	High Similarity	NPC247017
0.9272	High Similarity	NPC178854
0.9272	High Similarity	NPC266960
0.9272	High Similarity	NPC49824
0.9272	High Similarity	NPC98661
0.9267	High Similarity	NPC75279
0.9267	High Similarity	NPC250822
0.9267	High Similarity	NPC276409
0.9262	High Similarity	NPC31363
0.9262	High Similarity	NPC251110
0.9262	High Similarity	NPC171010
0.9257	High Similarity	NPC183950
0.9257	High Similarity	NPC259713
0.9257	High Similarity	NPC171916
0.9257	High Similarity	NPC137062

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 NPC156953 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	988
0.2-0.3	1831
0.3-0.4	2637
0.4-0.5	1761
0.5-0.6	969
0.6-0.7	362
0.7-0.8	116
0.8-0.85	36
0.85-0.9	15
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9396	High Similarity	NPD2801	Approved
0.92	High Similarity	NPD1934	Approved
0.9021	High Similarity	NPD1510	Phase 2
0.8919	High Similarity	NPD1511	Approved
0.8896	High Similarity	NPD3882	Suspended
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.88	High Similarity	NPD1512	Approved
0.875	High Similarity	NPD3818	Discontinued
0.8741	High Similarity	NPD1240	Approved
0.8726	High Similarity	NPD5494	Approved
0.871	High Similarity	NPD3817	Phase 2
0.8693	High Similarity	NPD4380	Phase 2
0.8625	High Similarity	NPD6168	Clinical (unspecified phase)
0.8625	High Similarity	NPD6167	Clinical (unspecified phase)
0.8625	High Similarity	NPD6166	Phase 2
0.8621	High Similarity	NPD1607	Approved
0.8616	High Similarity	NPD6232	Discontinued
0.8609	High Similarity	NPD4378	Clinical (unspecified phase)
0.8581	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD7473	Discontinued
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD943	Approved
0.8466	Intermediate Similarity	NPD7054	Approved
0.8446	Intermediate Similarity	NPD2796	Approved
0.8438	Intermediate Similarity	NPD1247	Approved
0.8418	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7472	Approved
0.8415	Intermediate Similarity	NPD7074	Phase 3
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8263	Intermediate Similarity	NPD7808	Phase 3
0.8253	Intermediate Similarity	NPD6797	Phase 2
0.825	Intermediate Similarity	NPD7075	Discontinued
0.8247	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8239	Intermediate Similarity	NPD5402	Approved
0.8212	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7251	Discontinued
0.8182	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.8105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD919	Approved
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.8054	Intermediate Similarity	NPD230	Phase 1
0.805	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3926	Phase 2
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD3750	Approved
0.7933	Intermediate Similarity	NPD447	Suspended
0.7929	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3027	Phase 3
0.7898	Intermediate Similarity	NPD2532	Approved
0.7898	Intermediate Similarity	NPD2533	Approved
0.7898	Intermediate Similarity	NPD2534	Approved
0.7895	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD9494	Approved
0.7879	Intermediate Similarity	NPD6959	Discontinued
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.7806	Intermediate Similarity	NPD2800	Approved
0.7805	Intermediate Similarity	NPD3749	Approved
0.7799	Intermediate Similarity	NPD920	Approved
0.7799	Intermediate Similarity	NPD5403	Approved
0.7785	Intermediate Similarity	NPD5401	Approved
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1613	Approved
0.7744	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2344	Approved
0.7673	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD37	Approved
0.7662	Intermediate Similarity	NPD3748	Approved
0.7651	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6651	Approved
0.7619	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6190	Approved
0.7593	Intermediate Similarity	NPD3226	Approved
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2798	Approved
0.7582	Intermediate Similarity	NPD1933	Approved
0.7582	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1243	Approved
0.7574	Intermediate Similarity	NPD5242	Approved
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.7544	Intermediate Similarity	NPD3751	Discontinued
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD1653	Approved
0.753	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD4965	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2309	Approved
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7436	Intermediate Similarity	NPD2799	Discontinued
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7429	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1203	Approved
0.74	Intermediate Similarity	NPD1470	Approved
0.7397	Intermediate Similarity	NPD9268	Approved
0.7394	Intermediate Similarity	NPD6386	Approved
0.7394	Intermediate Similarity	NPD6385	Approved
0.7391	Intermediate Similarity	NPD4357	Discontinued
0.7389	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD6100	Approved
0.7379	Intermediate Similarity	NPD5536	Phase 2
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5353	Approved
0.7355	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6844	Discontinued
0.7329	Intermediate Similarity	NPD1548	Phase 1
0.731	Intermediate Similarity	NPD3787	Discontinued
0.731	Intermediate Similarity	NPD5710	Approved
0.731	Intermediate Similarity	NPD5711	Approved
0.7303	Intermediate Similarity	NPD3018	Phase 2
0.7297	Intermediate Similarity	NPD6782	Approved
0.7297	Intermediate Similarity	NPD6776	Approved
0.7297	Intermediate Similarity	NPD6779	Approved
0.7297	Intermediate Similarity	NPD6778	Approved
0.7297	Intermediate Similarity	NPD6781	Approved
0.7297	Intermediate Similarity	NPD6777	Approved
0.7297	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD7458	Discontinued
0.7255	Intermediate Similarity	NPD6832	Phase 2
0.7255	Intermediate Similarity	NPD4908	Phase 1
0.725	Intermediate Similarity	NPD2654	Approved
0.7248	Intermediate Similarity	NPD1201	Approved
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7241	Intermediate Similarity	NPD7228	Approved
0.7239	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7033	Discontinued
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD9545	Approved
0.7205	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD3972	Approved
0.7192	Intermediate Similarity	NPD9493	Approved
0.7181	Intermediate Similarity	NPD7697	Approved
0.7181	Intermediate Similarity	NPD7698	Approved
0.7181	Intermediate Similarity	NPD7435	Discontinued
0.7181	Intermediate Similarity	NPD7696	Phase 3
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7167	Intermediate Similarity	NPD8150	Discontinued
0.7161	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3764	Approved
0.7161	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD2983	Phase 2
0.7152	Intermediate Similarity	NPD2982	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7133	Intermediate Similarity	NPD422	Phase 1
0.712	Intermediate Similarity	NPD4360	Phase 2
0.712	Intermediate Similarity	NPD4363	Phase 3
0.7107	Intermediate Similarity	NPD2899	Discontinued
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.7086	Intermediate Similarity	NPD1608	Approved
0.7086	Intermediate Similarity	NPD2981	Phase 2
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7078	Intermediate Similarity	NPD2861	Phase 2
0.7063	Intermediate Similarity	NPD5406	Approved
0.7063	Intermediate Similarity	NPD5408	Approved
0.7063	Intermediate Similarity	NPD5404	Approved
0.7063	Intermediate Similarity	NPD5405	Approved
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD4288	Approved
0.7051	Intermediate Similarity	NPD411	Approved
0.7037	Intermediate Similarity	NPD6823	Phase 2
0.7031	Intermediate Similarity	NPD7701	Phase 2
0.703	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2403	Approved
0.7027	Intermediate Similarity	NPD6534	Approved
0.7027	Intermediate Similarity	NPD6535	Approved
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD1876	Approved
0.6993	Remote Similarity	NPD3225	Approved
0.6989	Remote Similarity	NPD4362	Clinical (unspecified phase)

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