NPASS Compound

Structure

NPC262623 OpenBabel07101718202D 24 26 0 0 0 0 0 0 0 0999 V2000 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 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 3.4641 -0.0000 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 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 23 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 24 1 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	2.763
LogD:	2.699
LogS:	-3.779
# Rotatable Bonds:	4
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.792
Synthetic Accessibility Score:	2.207
Fsp3:	0.167
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:	3.9410337194567546e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	83.9389419555664%
Volume Distribution (VD):	0.545
Pgp-substrate:	11.518197059631348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.732
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.275
CYP2C9-inhibitor:	0.448
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.699
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.853
CYP3A4-substrate:	0.381

ADMET: Excretion

Clearance (CL):	8.297
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.388
Skin Sensitization:	0.526
Carcinogencity:	0.086
Eye Corrosion:	0.004
Eye Irritation:	0.364
Respiratory Toxicity:	0.373

Download Data

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

Natural Product: NPC262623

Natural Product ID:	NPC262623
*Common Name:**	7-Hydroxy-2',4',5'-Trimethoxyisoflavone
IUPAC Name:	7-hydroxy-3-(2,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	IXZYJZHCXHSCDY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-21-14-8-17(23-3)16(22-2)7-12(14)13-9-24-15-6-10(19)4-5-11(15)18(13)20/h4-9,19H,1-3H3
SMILES:	COc1cc(OC)c(cc1c1coc2c(c1=O)ccc(c2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455048
PubChem CID:	15337591
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
NPO10426	Eysenhardtia polystachya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644061]
NPO10426	Eysenhardtia polystachya	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[549944]

☑ 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 NPC262623 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	NPC156953
0.9931	High Similarity	NPC239363
0.9863	High Similarity	NPC124714
0.9795	High Similarity	NPC131266
0.9795	High Similarity	NPC291802
0.9795	High Similarity	NPC209487
0.9795	High Similarity	NPC216769
0.9795	High Similarity	NPC245382
0.9795	High Similarity	NPC269451
0.9795	High Similarity	NPC100263
0.9795	High Similarity	NPC100971
0.9795	High Similarity	NPC35763
0.9795	High Similarity	NPC121522
0.9795	High Similarity	NPC181209
0.9728	High Similarity	NPC280937
0.9728	High Similarity	NPC250557
0.9726	High Similarity	NPC19980
0.9726	High Similarity	NPC45291
0.9722	High Similarity	NPC93034
0.9722	High Similarity	NPC119660
0.9662	High Similarity	NPC134287
0.9662	High Similarity	NPC130589
0.9662	High Similarity	NPC39184
0.9658	High Similarity	NPC10467
0.9653	High Similarity	NPC120924
0.9653	High Similarity	NPC216314
0.9653	High Similarity	NPC195919
0.9653	High Similarity	NPC12377
0.9595	High Similarity	NPC472915
0.9592	High Similarity	NPC226973
0.9592	High Similarity	NPC308451
0.9592	High Similarity	NPC208043
0.9589	High Similarity	NPC102003
0.9589	High Similarity	NPC40290
0.9589	High Similarity	NPC264550
0.9589	High Similarity	NPC195763
0.9589	High Similarity	NPC264289
0.9589	High Similarity	NPC142876
0.9589	High Similarity	NPC333691
0.9589	High Similarity	NPC69430
0.9589	High Similarity	NPC200060
0.9589	High Similarity	NPC139293
0.9589	High Similarity	NPC92722
0.9533	High Similarity	NPC78103
0.9533	High Similarity	NPC181960
0.9533	High Similarity	NPC476981
0.953	High Similarity	NPC37392
0.953	High Similarity	NPC256612
0.953	High Similarity	NPC213622
0.953	High Similarity	NPC472909
0.953	High Similarity	NPC20830
0.9524	High Similarity	NPC306821
0.9521	High Similarity	NPC80710
0.9521	High Similarity	NPC183655
0.9521	High Similarity	NPC203747
0.9521	High Similarity	NPC139364
0.9521	High Similarity	NPC254702
0.9521	High Similarity	NPC287395
0.9521	High Similarity	NPC131451
0.9521	High Similarity	NPC15329
0.9521	High Similarity	NPC218490
0.9521	High Similarity	NPC194653
0.9514	High Similarity	NPC182842
0.947	High Similarity	NPC215375
0.947	High Similarity	NPC62518
0.9467	High Similarity	NPC472916
0.9463	High Similarity	NPC47781
0.9463	High Similarity	NPC22519
0.9463	High Similarity	NPC176775
0.9463	High Similarity	NPC160951
0.9463	High Similarity	NPC255350
0.9463	High Similarity	NPC145379
0.9463	High Similarity	NPC69394
0.9463	High Similarity	NPC183878
0.9463	High Similarity	NPC86485
0.9463	High Similarity	NPC231018
0.9463	High Similarity	NPC274327
0.9459	High Similarity	NPC149614
0.9459	High Similarity	NPC256406
0.9459	High Similarity	NPC117579
0.9456	High Similarity	NPC328119
0.9452	High Similarity	NPC125449
0.9452	High Similarity	NPC188074
0.9444	High Similarity	NPC119663
0.9408	High Similarity	NPC476980
0.9404	High Similarity	NPC162869
0.9404	High Similarity	NPC472911
0.9404	High Similarity	NPC245758
0.9404	High Similarity	NPC470402
0.9404	High Similarity	NPC167595
0.9404	High Similarity	NPC156057
0.9404	High Similarity	NPC474208
0.9404	High Similarity	NPC475267
0.9404	High Similarity	NPC210084
0.9404	High Similarity	NPC474836
0.9404	High Similarity	NPC472910
0.9404	High Similarity	NPC222814
0.9404	High Similarity	NPC472913
0.9404	High Similarity	NPC48208
0.9404	High Similarity	NPC472914
0.9404	High Similarity	NPC99597
0.9404	High Similarity	NPC96167
0.94	High Similarity	NPC163780
0.94	High Similarity	NPC138360
0.94	High Similarity	NPC50715
0.94	High Similarity	NPC32557
0.94	High Similarity	NPC189960
0.94	High Similarity	NPC196439
0.94	High Similarity	NPC167815
0.94	High Similarity	NPC4455
0.94	High Similarity	NPC2476
0.94	High Similarity	NPC31018
0.94	High Similarity	NPC280339
0.94	High Similarity	NPC227325
0.94	High Similarity	NPC208197
0.94	High Similarity	NPC255807
0.94	High Similarity	NPC201136
0.94	High Similarity	NPC183597
0.94	High Similarity	NPC128863
0.94	High Similarity	NPC146165
0.94	High Similarity	NPC2928
0.94	High Similarity	NPC92659
0.9396	High Similarity	NPC474993
0.9396	High Similarity	NPC239128
0.9396	High Similarity	NPC25270
0.9396	High Similarity	NPC71334
0.9396	High Similarity	NPC301123
0.9396	High Similarity	NPC100887
0.9396	High Similarity	NPC301323
0.9396	High Similarity	NPC187498
0.9396	High Similarity	NPC156222
0.9396	High Similarity	NPC131624
0.9396	High Similarity	NPC39732
0.9396	High Similarity	NPC83508
0.9396	High Similarity	NPC188203
0.9396	High Similarity	NPC241498
0.9396	High Similarity	NPC162313
0.9396	High Similarity	NPC120163
0.9396	High Similarity	NPC293183
0.9396	High Similarity	NPC275836
0.9396	High Similarity	NPC256283
0.9396	High Similarity	NPC222830
0.9396	High Similarity	NPC275722
0.9396	High Similarity	NPC198826
0.9396	High Similarity	NPC60972
0.9396	High Similarity	NPC57030
0.9396	High Similarity	NPC212678
0.9392	High Similarity	NPC179183
0.9388	High Similarity	NPC195202
0.9384	High Similarity	NPC226987
0.9384	High Similarity	NPC165389
0.9384	High Similarity	NPC143903
0.9375	High Similarity	NPC185607
0.9346	High Similarity	NPC260640
0.9346	High Similarity	NPC295009
0.9346	High Similarity	NPC258331
0.9342	High Similarity	NPC152904
0.9338	High Similarity	NPC255106
0.9338	High Similarity	NPC178854
0.9338	High Similarity	NPC49824
0.9338	High Similarity	NPC235165
0.9333	High Similarity	NPC167091
0.9333	High Similarity	NPC88645
0.9333	High Similarity	NPC250822
0.9333	High Similarity	NPC276409
0.9333	High Similarity	NPC206238
0.9333	High Similarity	NPC292214
0.9333	High Similarity	NPC75279
0.9333	High Similarity	NPC271779
0.9324	High Similarity	NPC38545
0.9324	High Similarity	NPC171916
0.932	High Similarity	NPC12200
0.932	High Similarity	NPC33265
0.932	High Similarity	NPC205522
0.932	High Similarity	NPC62536
0.9306	High Similarity	NPC58229
0.9286	High Similarity	NPC83922
0.9286	High Similarity	NPC472448
0.9286	High Similarity	NPC81679
0.9286	High Similarity	NPC261470
0.9281	High Similarity	NPC225624
0.9281	High Similarity	NPC285973
0.9276	High Similarity	NPC227192
0.9276	High Similarity	NPC262286
0.9276	High Similarity	NPC75215
0.9276	High Similarity	NPC203891
0.9276	High Similarity	NPC110070
0.9276	High Similarity	NPC36852
0.9276	High Similarity	NPC101830
0.9276	High Similarity	NPC189179
0.9276	High Similarity	NPC469584
0.9276	High Similarity	NPC299520
0.9276	High Similarity	NPC129684
0.9276	High Similarity	NPC224137
0.9276	High Similarity	NPC78225
0.9276	High Similarity	NPC93376
0.9272	High Similarity	NPC26227
0.9272	High Similarity	NPC201451
0.9272	High Similarity	NPC44079
0.9267	High Similarity	NPC39007

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 NPC262623 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
0.9463	High Similarity	NPD2801	Approved
0.9139	High Similarity	NPD1934	Approved
0.8961	High Similarity	NPD3882	Suspended
0.8958	High Similarity	NPD1510	Phase 2
0.8954	High Similarity	NPD2393	Clinical (unspecified phase)
0.8859	High Similarity	NPD1511	Approved
0.8812	High Similarity	NPD3818	Discontinued
0.879	High Similarity	NPD5494	Approved
0.8774	High Similarity	NPD3817	Phase 2
0.8758	High Similarity	NPD4380	Phase 2
0.8742	High Similarity	NPD1512	Approved
0.8688	High Similarity	NPD6168	Clinical (unspecified phase)
0.8688	High Similarity	NPD6166	Phase 2
0.8688	High Similarity	NPD6167	Clinical (unspecified phase)
0.8681	High Similarity	NPD1240	Approved
0.8679	High Similarity	NPD6232	Discontinued
0.8675	High Similarity	NPD4378	Clinical (unspecified phase)
0.8634	High Similarity	NPD7473	Discontinued
0.8562	High Similarity	NPD1607	Approved
0.8545	High Similarity	NPD4338	Clinical (unspecified phase)
0.8528	High Similarity	NPD7054	Approved
0.8523	High Similarity	NPD1549	Phase 2
0.8514	High Similarity	NPD2796	Approved
0.8481	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7472	Approved
0.8476	Intermediate Similarity	NPD7074	Phase 3
0.8456	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD943	Approved
0.8389	Intermediate Similarity	NPD2935	Discontinued
0.8385	Intermediate Similarity	NPD1247	Approved
0.8323	Intermediate Similarity	NPD7808	Phase 3
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD6797	Phase 2
0.8312	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD5844	Phase 1
0.8302	Intermediate Similarity	NPD5402	Approved
0.8263	Intermediate Similarity	NPD7251	Discontinued
0.8247	Intermediate Similarity	NPD6799	Approved
0.8239	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7819	Suspended
0.8205	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6801	Discontinued
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7411	Suspended
0.8075	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD3926	Phase 2
0.8052	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6599	Discontinued
0.8037	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD230	Phase 1
0.7988	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3027	Phase 3
0.7962	Intermediate Similarity	NPD2534	Approved
0.7962	Intermediate Similarity	NPD2533	Approved
0.7962	Intermediate Similarity	NPD2532	Approved
0.7939	Intermediate Similarity	NPD6959	Discontinued
0.7935	Intermediate Similarity	NPD3750	Approved
0.7881	Intermediate Similarity	NPD447	Suspended
0.7862	Intermediate Similarity	NPD5403	Approved
0.7843	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD9494	Approved
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.7829	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7768	Phase 2
0.7798	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1551	Phase 2
0.7785	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD3749	Approved
0.7756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2800	Approved
0.775	Intermediate Similarity	NPD920	Approved
0.7736	Intermediate Similarity	NPD5401	Approved
0.773	Intermediate Similarity	NPD37	Approved
0.7712	Intermediate Similarity	NPD6651	Approved
0.7697	Intermediate Similarity	NPD1613	Approved
0.7697	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6190	Approved
0.7651	Intermediate Similarity	NPD2798	Approved
0.764	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5242	Approved
0.7628	Intermediate Similarity	NPD2344	Approved
0.7625	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD3748	Approved
0.7605	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7593	Intermediate Similarity	NPD1653	Approved
0.759	Intermediate Similarity	NPD4966	Approved
0.759	Intermediate Similarity	NPD4965	Approved
0.759	Intermediate Similarity	NPD4967	Phase 2
0.7572	Intermediate Similarity	NPD5953	Discontinued
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.7558	Intermediate Similarity	NPD7286	Phase 2
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD1243	Approved
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6386	Approved
0.7455	Intermediate Similarity	NPD6385	Approved
0.7453	Intermediate Similarity	NPD4357	Discontinued
0.7452	Intermediate Similarity	NPD6100	Approved
0.7452	Intermediate Similarity	NPD6099	Approved
0.7448	Intermediate Similarity	NPD5536	Phase 2
0.7438	Intermediate Similarity	NPD2309	Approved
0.7429	Intermediate Similarity	NPD7685	Pre-registration
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5353	Approved
0.741	Intermediate Similarity	NPD6844	Discontinued
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7383	Intermediate Similarity	NPD9269	Phase 2
0.7368	Intermediate Similarity	NPD5711	Approved
0.7368	Intermediate Similarity	NPD3018	Phase 2
0.7368	Intermediate Similarity	NPD5710	Approved
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7351	Intermediate Similarity	NPD1203	Approved
0.7351	Intermediate Similarity	NPD6777	Approved
0.7351	Intermediate Similarity	NPD6778	Approved
0.7351	Intermediate Similarity	NPD6776	Approved
0.7351	Intermediate Similarity	NPD6782	Approved
0.7351	Intermediate Similarity	NPD1470	Approved
0.7351	Intermediate Similarity	NPD6779	Approved
0.7351	Intermediate Similarity	NPD6781	Approved
0.7351	Intermediate Similarity	NPD6780	Approved
0.7347	Intermediate Similarity	NPD9268	Approved
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.732	Intermediate Similarity	NPD6832	Phase 2
0.732	Intermediate Similarity	NPD4908	Phase 1
0.7315	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2654	Approved
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7228	Approved
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7267	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7697	Approved
0.7234	Intermediate Similarity	NPD7435	Discontinued
0.7234	Intermediate Similarity	NPD7696	Phase 3
0.7234	Intermediate Similarity	NPD7698	Approved
0.7226	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3268	Approved
0.7222	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD2983	Phase 2
0.7219	Intermediate Similarity	NPD2982	Phase 2
0.72	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD1610	Phase 2
0.7196	Intermediate Similarity	NPD7871	Phase 2
0.7196	Intermediate Similarity	NPD7870	Phase 2
0.7191	Intermediate Similarity	NPD7549	Discontinued
0.7189	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4363	Phase 3
0.7174	Intermediate Similarity	NPD4360	Phase 2
0.717	Intermediate Similarity	NPD4308	Phase 3
0.7162	Intermediate Similarity	NPD9545	Approved
0.7157	Intermediate Similarity	NPD2899	Discontinued
0.7152	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD2981	Phase 2
0.7151	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD9493	Approved
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7125	Intermediate Similarity	NPD5405	Approved
0.7125	Intermediate Similarity	NPD5406	Approved
0.7125	Intermediate Similarity	NPD5404	Approved
0.7125	Intermediate Similarity	NPD5408	Approved
0.7124	Intermediate Similarity	NPD2797	Approved
0.7115	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6823	Phase 2
0.7086	Intermediate Similarity	NPD2403	Approved
0.7086	Intermediate Similarity	NPD422	Phase 1
0.7083	Intermediate Similarity	NPD7701	Phase 2
0.7081	Intermediate Similarity	NPD6535	Approved
0.7081	Intermediate Similarity	NPD6534	Approved
0.707	Intermediate Similarity	NPD6233	Phase 2
0.7069	Intermediate Similarity	NPD7229	Phase 3
0.7055	Intermediate Similarity	NPD5283	Phase 1
0.7043	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4361	Phase 2
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1608	Approved
0.7031	Intermediate Similarity	NPD7584	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