NPASS Compound

Structure

NPC40290 OpenBabel07101719512D 22 24 0 0 0 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 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 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 22 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 14 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	2.397
LogD:	2.361
LogS:	-3.497
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	2.488
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	9.763347406988032e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.629
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.60204315185547%
Volume Distribution (VD):	0.388
Pgp-substrate:	4.2448835372924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.77
CYP2C19-inhibitor:	0.5
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.776
CYP2D6-substrate:	0.668
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	6.869
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.734
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.919
Carcinogencity:	0.285
Eye Corrosion:	0.008
Eye Irritation:	0.941
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC40290

Natural Product ID:	NPC40290
*Common Name:**	3-(2,4-Dihydroxy-3-Methoxyphenyl)-7-Hydroxychromen-4-One
IUPAC Name:	3-(2,4-dihydroxy-3-methoxyphenyl)-7-hydroxychromen-4-one
Synonyms:
Standard InCHIKey:	IELIPFOSZBGSTN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-21-16-12(18)5-4-9(15(16)20)11-7-22-13-6-8(17)2-3-10(13)14(11)19/h2-7,17-18,20H,1H3
SMILES:	COc1c(ccc(c2coc3cc(ccc3c2=O)O)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076305
PubChem CID:	14077823
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002605] 3'-O-methylated isoflavonoids [CHEMONTID:0002690] 3'-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
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
GI50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	37000.0	nM	PMID[497380]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	68000.0	nM	PMID[497380]

☑ 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 NPC40290 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	494
0.1-0.2	2000
0.2-0.3	4917
0.3-0.4	11344
0.4-0.5	6055
0.5-0.6	3762
0.6-0.7	5096
0.7-0.8	4953
0.8-0.85	2133
0.85-0.9	1215
0.9-0.95	607
0.95-1	121

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC264289
1.0	High Similarity	NPC200060
1.0	High Similarity	NPC139293
1.0	High Similarity	NPC69430
1.0	High Similarity	NPC195763
1.0	High Similarity	NPC333691
1.0	High Similarity	NPC264550
1.0	High Similarity	NPC142876
0.993	High Similarity	NPC194653
0.993	High Similarity	NPC254702
0.993	High Similarity	NPC139364
0.993	High Similarity	NPC203747
0.993	High Similarity	NPC80710
0.9859	High Similarity	NPC125449
0.9859	High Similarity	NPC188074
0.9793	High Similarity	NPC131266
0.9793	High Similarity	NPC291802
0.9793	High Similarity	NPC209487
0.9793	High Similarity	NPC121522
0.9793	High Similarity	NPC216769
0.9793	High Similarity	NPC245382
0.9793	High Similarity	NPC269451
0.9793	High Similarity	NPC100263
0.9793	High Similarity	NPC100971
0.9793	High Similarity	NPC35763
0.9793	High Similarity	NPC181209
0.9789	High Similarity	NPC12377
0.9726	High Similarity	NPC124714
0.9724	High Similarity	NPC256406
0.9724	High Similarity	NPC19980
0.9724	High Similarity	NPC45291
0.966	High Similarity	NPC39184
0.9655	High Similarity	NPC156953
0.9655	High Similarity	NPC10467
0.9648	High Similarity	NPC142165
0.9648	High Similarity	NPC38065
0.9648	High Similarity	NPC242893
0.9592	High Similarity	NPC250557
0.9589	High Similarity	NPC31363
0.9589	High Similarity	NPC262623
0.9586	High Similarity	NPC171916
0.9586	High Similarity	NPC38545
0.9577	High Similarity	NPC287722
0.9577	High Similarity	NPC254659
0.9527	High Similarity	NPC130589
0.9527	High Similarity	NPC134287
0.9524	High Similarity	NPC257648
0.9524	High Similarity	NPC60972
0.9524	High Similarity	NPC39732
0.9524	High Similarity	NPC477231
0.9521	High Similarity	NPC29231
0.9521	High Similarity	NPC239363
0.9521	High Similarity	NPC85131
0.9521	High Similarity	NPC472279
0.9517	High Similarity	NPC238279
0.9517	High Similarity	NPC166036
0.9517	High Similarity	NPC218490
0.9517	High Similarity	NPC203077
0.9517	High Similarity	NPC287395
0.9517	High Similarity	NPC183655
0.951	High Similarity	NPC207732
0.9507	High Similarity	NPC301178
0.9507	High Similarity	NPC284556
0.9507	High Similarity	NPC312256
0.9463	High Similarity	NPC472455
0.9459	High Similarity	NPC469550
0.9452	High Similarity	NPC183950
0.9452	High Similarity	NPC102003
0.9452	High Similarity	NPC137062
0.9452	High Similarity	NPC92722
0.9452	High Similarity	NPC223579
0.9452	High Similarity	NPC287101
0.9452	High Similarity	NPC52005
0.9448	High Similarity	NPC168803
0.9441	High Similarity	NPC471417
0.9441	High Similarity	NPC119663
0.9437	High Similarity	NPC110419
0.94	High Similarity	NPC210084
0.94	High Similarity	NPC99597
0.94	High Similarity	NPC299520
0.94	High Similarity	NPC129684
0.94	High Similarity	NPC78103
0.9396	High Similarity	NPC213622
0.9396	High Similarity	NPC234255
0.9396	High Similarity	NPC256612
0.9396	High Similarity	NPC20830
0.9396	High Similarity	NPC230149
0.9396	High Similarity	NPC472280
0.9396	High Similarity	NPC168247
0.9396	High Similarity	NPC152951
0.9396	High Similarity	NPC117992
0.9396	High Similarity	NPC57674
0.9396	High Similarity	NPC2928
0.9392	High Similarity	NPC324233
0.9392	High Similarity	NPC474993
0.9392	High Similarity	NPC301323
0.9392	High Similarity	NPC239128
0.9392	High Similarity	NPC25270
0.9392	High Similarity	NPC71334
0.9392	High Similarity	NPC472912
0.9392	High Similarity	NPC55205
0.9392	High Similarity	NPC100887
0.9392	High Similarity	NPC256283
0.9392	High Similarity	NPC187498
0.9392	High Similarity	NPC188203
0.9392	High Similarity	NPC156222
0.9392	High Similarity	NPC131624
0.9392	High Similarity	NPC241498
0.9392	High Similarity	NPC162313
0.9392	High Similarity	NPC302950
0.9392	High Similarity	NPC120163
0.9392	High Similarity	NPC260979
0.9392	High Similarity	NPC236637
0.9392	High Similarity	NPC293183
0.9392	High Similarity	NPC275836
0.9392	High Similarity	NPC222830
0.9392	High Similarity	NPC275722
0.9392	High Similarity	NPC323626
0.9392	High Similarity	NPC219582
0.9392	High Similarity	NPC198826
0.9392	High Similarity	NPC57030
0.9392	High Similarity	NPC212678
0.9392	High Similarity	NPC83508
0.9384	High Similarity	NPC272721
0.9384	High Similarity	NPC131451
0.9384	High Similarity	NPC474903
0.9384	High Similarity	NPC196277
0.9384	High Similarity	NPC15329
0.9384	High Similarity	NPC120464
0.9384	High Similarity	NPC43669
0.9379	High Similarity	NPC143903
0.9379	High Similarity	NPC226987
0.9371	High Similarity	NPC185607
0.9366	High Similarity	NPC50823
0.9342	High Similarity	NPC260640
0.9342	High Similarity	NPC295009
0.9338	High Similarity	NPC204879
0.9338	High Similarity	NPC184755
0.9338	High Similarity	NPC55738
0.9338	High Similarity	NPC74178
0.9333	High Similarity	NPC472916
0.9333	High Similarity	NPC133970
0.9333	High Similarity	NPC6633
0.9333	High Similarity	NPC5322
0.9333	High Similarity	NPC474638
0.9333	High Similarity	NPC255106
0.9333	High Similarity	NPC235165
0.9333	High Similarity	NPC265511
0.9329	High Similarity	NPC176775
0.9329	High Similarity	NPC206238
0.9329	High Similarity	NPC69394
0.9329	High Similarity	NPC273462
0.9329	High Similarity	NPC292214
0.9329	High Similarity	NPC47781
0.9329	High Similarity	NPC255350
0.9329	High Similarity	NPC145379
0.9329	High Similarity	NPC22519
0.9329	High Similarity	NPC160951
0.9329	High Similarity	NPC18727
0.9329	High Similarity	NPC33051
0.9329	High Similarity	NPC271779
0.9329	High Similarity	NPC167091
0.9329	High Similarity	NPC274327
0.9329	High Similarity	NPC227337
0.9329	High Similarity	NPC49402
0.9329	High Similarity	NPC70433
0.9329	High Similarity	NPC88645
0.9329	High Similarity	NPC280937
0.9329	High Similarity	NPC183878
0.9329	High Similarity	NPC231018
0.9324	High Similarity	NPC252933
0.9324	High Similarity	NPC54394
0.9324	High Similarity	NPC200740
0.9324	High Similarity	NPC125062
0.932	High Similarity	NPC105512
0.932	High Similarity	NPC177298
0.932	High Similarity	NPC48479
0.9315	High Similarity	NPC93034
0.9315	High Similarity	NPC95864
0.9315	High Similarity	NPC119660
0.9315	High Similarity	NPC12200
0.9315	High Similarity	NPC108406
0.9315	High Similarity	NPC77378
0.931	High Similarity	NPC157133
0.9296	High Similarity	NPC90665
0.9296	High Similarity	NPC55162
0.9296	High Similarity	NPC12175
0.9296	High Similarity	NPC309154
0.9296	High Similarity	NPC278323
0.9296	High Similarity	NPC279668
0.9276	High Similarity	NPC285973
0.9276	High Similarity	NPC474960
0.9276	High Similarity	NPC225624
0.9276	High Similarity	NPC476980
0.9272	High Similarity	NPC218313
0.9272	High Similarity	NPC475267
0.9272	High Similarity	NPC222814
0.9272	High Similarity	NPC472910
0.9272	High Similarity	NPC474836
0.9272	High Similarity	NPC48208

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 NPC40290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	471
0.1-0.2	986
0.2-0.3	1903
0.3-0.4	2608
0.4-0.5	1725
0.5-0.6	939
0.6-0.7	360
0.7-0.8	101
0.8-0.85	36
0.85-0.9	12
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9392	High Similarity	NPD1934	Approved
0.9329	High Similarity	NPD2801	Approved
0.9205	High Similarity	NPD3882	Suspended
0.911	High Similarity	NPD1511	Approved
0.9085	High Similarity	NPD1510	Phase 2
0.9073	High Similarity	NPD2393	Clinical (unspecified phase)
0.8986	High Similarity	NPD1512	Approved
0.8924	High Similarity	NPD3818	Discontinued
0.8803	High Similarity	NPD943	Approved
0.8803	High Similarity	NPD1240	Approved
0.8797	High Similarity	NPD6166	Phase 2
0.8797	High Similarity	NPD6167	Clinical (unspecified phase)
0.8797	High Similarity	NPD6168	Clinical (unspecified phase)
0.8766	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD4380	Phase 2
0.8681	High Similarity	NPD1607	Approved
0.8639	High Similarity	NPD1549	Phase 2
0.8634	High Similarity	NPD7054	Approved
0.859	High Similarity	NPD4868	Clinical (unspecified phase)
0.858	High Similarity	NPD7472	Approved
0.858	High Similarity	NPD7074	Phase 3
0.8571	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1550	Clinical (unspecified phase)
0.8553	High Similarity	NPD6232	Discontinued
0.8543	High Similarity	NPD4378	Clinical (unspecified phase)
0.8509	High Similarity	NPD7473	Discontinued
0.8503	High Similarity	NPD2796	Approved
0.8428	Intermediate Similarity	NPD5494	Approved
0.8424	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7075	Discontinued
0.8418	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6797	Phase 2
0.8364	Intermediate Similarity	NPD7251	Discontinued
0.8355	Intermediate Similarity	NPD6799	Approved
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7808	Phase 3
0.8301	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD230	Phase 1
0.8228	Intermediate Similarity	NPD1465	Phase 2
0.8228	Intermediate Similarity	NPD7819	Suspended
0.8194	Intermediate Similarity	NPD9494	Approved
0.8194	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8148	Intermediate Similarity	NPD1247	Approved
0.8137	Intermediate Similarity	NPD919	Approved
0.8101	Intermediate Similarity	NPD7411	Suspended
0.8084	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD3027	Phase 3
0.8067	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5402	Approved
0.8049	Intermediate Similarity	NPD3926	Phase 2
0.8039	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.7964	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5844	Phase 1
0.7962	Intermediate Similarity	NPD5403	Approved
0.7949	Intermediate Similarity	NPD5401	Approved
0.7947	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1613	Approved
0.7919	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.7891	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD447	Suspended
0.7853	Intermediate Similarity	NPD3749	Approved
0.7834	Intermediate Similarity	NPD2532	Approved
0.7834	Intermediate Similarity	NPD2534	Approved
0.7834	Intermediate Similarity	NPD2533	Approved
0.7824	Intermediate Similarity	NPD6559	Discontinued
0.7823	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6959	Discontinued
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2800	Approved
0.7736	Intermediate Similarity	NPD920	Approved
0.7727	Intermediate Similarity	NPD2344	Approved
0.7714	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7697	Intermediate Similarity	NPD6651	Approved
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7667	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6190	Approved
0.7635	Intermediate Similarity	NPD2798	Approved
0.7632	Intermediate Similarity	NPD1933	Approved
0.7628	Intermediate Similarity	NPD1243	Approved
0.7624	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD37	Approved
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7603	Intermediate Similarity	NPD9269	Phase 2
0.7595	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5953	Discontinued
0.755	Intermediate Similarity	NPD2313	Discontinued
0.7543	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2309	Approved
0.7531	Intermediate Similarity	NPD3226	Approved
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5242	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7471	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD4967	Phase 2
0.747	Intermediate Similarity	NPD4965	Approved
0.7469	Intermediate Similarity	NPD1653	Approved
0.745	Intermediate Similarity	NPD1470	Approved
0.745	Intermediate Similarity	NPD1203	Approved
0.7442	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD7390	Discontinued
0.7438	Intermediate Similarity	NPD4357	Discontinued
0.7436	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD6100	Approved
0.7431	Intermediate Similarity	NPD5536	Phase 2
0.743	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2346	Discontinued
0.7384	Intermediate Similarity	NPD7228	Approved
0.7379	Intermediate Similarity	NPD1548	Phase 1
0.7351	Intermediate Similarity	NPD3018	Phase 2
0.7333	Intermediate Similarity	NPD6385	Approved
0.7333	Intermediate Similarity	NPD6386	Approved
0.7329	Intermediate Similarity	NPD9268	Approved
0.7317	Intermediate Similarity	NPD7458	Discontinued
0.7305	Intermediate Similarity	NPD5353	Approved
0.7303	Intermediate Similarity	NPD4908	Phase 1
0.7303	Intermediate Similarity	NPD6832	Phase 2
0.7297	Intermediate Similarity	NPD1201	Approved
0.7297	Intermediate Similarity	NPD1610	Phase 2
0.7296	Intermediate Similarity	NPD2654	Approved
0.729	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.7261	Intermediate Similarity	NPD7033	Discontinued
0.726	Intermediate Similarity	NPD9545	Approved
0.7254	Intermediate Similarity	NPD228	Approved
0.7251	Intermediate Similarity	NPD5711	Approved
0.7251	Intermediate Similarity	NPD5710	Approved
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.725	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3972	Approved
0.7248	Intermediate Similarity	NPD9717	Approved
0.7241	Intermediate Similarity	NPD9493	Approved
0.7208	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD3764	Approved
0.7208	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD2982	Phase 2
0.7181	Intermediate Similarity	NPD422	Phase 1
0.7151	Intermediate Similarity	NPD6778	Approved
0.7151	Intermediate Similarity	NPD6781	Approved
0.7151	Intermediate Similarity	NPD6782	Approved
0.7151	Intermediate Similarity	NPD6780	Approved
0.7151	Intermediate Similarity	NPD6779	Approved
0.7151	Intermediate Similarity	NPD6777	Approved
0.7151	Intermediate Similarity	NPD6776	Approved
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7133	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD8151	Discontinued
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.7107	Intermediate Similarity	NPD5408	Approved
0.7107	Intermediate Similarity	NPD5405	Approved
0.7107	Intermediate Similarity	NPD5404	Approved
0.7107	Intermediate Similarity	NPD5406	Approved
0.7105	Intermediate Similarity	NPD2797	Approved
0.7101	Intermediate Similarity	NPD4288	Approved
0.7097	Intermediate Similarity	NPD6798	Discontinued
0.7097	Intermediate Similarity	NPD411	Approved
0.7083	Intermediate Similarity	NPD6844	Discontinued
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4363	Phase 3
0.7065	Intermediate Similarity	NPD4360	Phase 2
0.7063	Intermediate Similarity	NPD7266	Discontinued
0.7056	Intermediate Similarity	NPD2899	Discontinued
0.7039	Intermediate Similarity	NPD1876	Approved
0.7039	Intermediate Similarity	NPD3225	Approved
0.7037	Intermediate Similarity	NPD7435	Discontinued
0.7037	Intermediate Similarity	NPD8166	Discontinued
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7027	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4361	Phase 2
0.7016	Intermediate Similarity	NPD7584	Approved
0.7007	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3455	Phase 2
0.7006	Intermediate Similarity	NPD4307	Phase 2
0.7006	Intermediate Similarity	NPD824	Approved
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2296	Approved
0.7	Intermediate Similarity	NPD5978	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