NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	2.77
LogD:	2.642
LogS:	-3.529
# Rotatable Bonds:	1
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	2.064
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.724
MDCK Permeability:	1.5746882127132267e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.28
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.329
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	97.8775863647461%
Volume Distribution (VD):	0.484
Pgp-substrate:	1.916872501373291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.146
CYP2C19-inhibitor:	0.54
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.466
CYP2C9-substrate:	0.801
CYP2D6-inhibitor:	0.898
CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.536
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	6.347
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.629
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.45
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.916
Carcinogencity:	0.606
Eye Corrosion:	0.031
Eye Irritation:	0.969
Respiratory Toxicity:	0.155

Download Data

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

Natural Product: NPC324929

Natural Product ID:	NPC324929
*Common Name:**	3-(3,4-Dihydroxyphenyl)Chromen-4-One
IUPAC Name:	3-(3,4-dihydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	JGEXBQSHBMXCHX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O4/c16-12-6-5-9(7-13(12)17)11-8-19-14-4-2-1-3-10(14)15(11)18/h1-8,16-17H
SMILES:	Oc1ccc(cc1O)c1coc2c(c1=O)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1089054
PubChem CID:	14680579
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2010354]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21879714]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32293887]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1250	Individual Protein	Macrophage migration inhibitory factor	Homo sapiens	IC50	=	38.0	nM	PMID[505609]

☑ 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 NPC324929 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	501
0.1-0.2	2059
0.2-0.3	4826
0.3-0.4	11976
0.4-0.5	5366
0.5-0.6	4082
0.6-0.7	6173
0.7-0.8	5578
0.8-0.85	1497
0.85-0.9	558
0.9-0.95	78
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC38065
0.9416	High Similarity	NPC242893
0.9214	High Similarity	NPC125449
0.9214	High Similarity	NPC188074
0.9149	High Similarity	NPC218490
0.9149	High Similarity	NPC139364
0.9149	High Similarity	NPC194653
0.9149	High Similarity	NPC80710
0.9149	High Similarity	NPC203747
0.9149	High Similarity	NPC254702
0.9085	High Similarity	NPC195763
0.9085	High Similarity	NPC264289
0.9085	High Similarity	NPC40290
0.9085	High Similarity	NPC69430
0.9085	High Similarity	NPC139293
0.9085	High Similarity	NPC200060
0.9085	High Similarity	NPC264550
0.9085	High Similarity	NPC333691
0.9085	High Similarity	NPC38545
0.9085	High Similarity	NPC171916
0.9085	High Similarity	NPC142876
0.9071	High Similarity	NPC73416
0.9071	High Similarity	NPC160777
0.9065	High Similarity	NPC287722
0.9021	High Similarity	NPC85131
0.9021	High Similarity	NPC10467
0.9014	High Similarity	NPC238279
0.9014	High Similarity	NPC166036
0.9014	High Similarity	NPC203077
0.9007	High Similarity	NPC12377
0.8993	High Similarity	NPC284556
0.8993	High Similarity	NPC301178
0.8978	High Similarity	NPC212767
0.8958	High Similarity	NPC256406
0.8955	High Similarity	NPC50763
0.8951	High Similarity	NPC1612
0.8951	High Similarity	NPC105512
0.8951	High Similarity	NPC183959
0.8947	High Similarity	NPC66905
0.8944	High Similarity	NPC95864
0.8936	High Similarity	NPC70136
0.8929	High Similarity	NPC254659
0.8929	High Similarity	NPC471417
0.8905	High Similarity	NPC193792
0.8897	High Similarity	NPC269451
0.8897	High Similarity	NPC245382
0.8897	High Similarity	NPC131266
0.8897	High Similarity	NPC209487
0.8897	High Similarity	NPC216769
0.8897	High Similarity	NPC100263
0.8897	High Similarity	NPC121522
0.8897	High Similarity	NPC323626
0.8897	High Similarity	NPC35763
0.8897	High Similarity	NPC181209
0.8897	High Similarity	NPC100971
0.8897	High Similarity	NPC291802
0.8897	High Similarity	NPC324233
0.8881	High Similarity	NPC119059
0.8881	High Similarity	NPC294852
0.8881	High Similarity	NPC188679
0.8881	High Similarity	NPC321011
0.8881	High Similarity	NPC3036
0.8865	High Similarity	NPC279121
0.8865	High Similarity	NPC142165
0.8836	High Similarity	NPC124714
0.8832	High Similarity	NPC39426
0.8832	High Similarity	NPC234560
0.8828	High Similarity	NPC19980
0.8828	High Similarity	NPC45291
0.8828	High Similarity	NPC118427
0.8811	High Similarity	NPC74881
0.8811	High Similarity	NPC108406
0.8811	High Similarity	NPC168803
0.8811	High Similarity	NPC51443
0.8794	High Similarity	NPC175013
0.8794	High Similarity	NPC46161
0.8794	High Similarity	NPC239608
0.8786	High Similarity	NPC84273
0.8776	High Similarity	NPC39184
0.8768	High Similarity	NPC235428
0.8768	High Similarity	NPC87545
0.8767	High Similarity	NPC164912
0.8759	High Similarity	NPC29231
0.8759	High Similarity	NPC156953
0.875	High Similarity	NPC43669
0.875	High Similarity	NPC12367
0.875	High Similarity	NPC287395
0.875	High Similarity	NPC272721
0.875	High Similarity	NPC183655
0.875	High Similarity	NPC196277
0.875	High Similarity	NPC118726
0.8741	High Similarity	NPC20791
0.8741	High Similarity	NPC179271
0.8722	High Similarity	NPC32163
0.8722	High Similarity	NPC16651
0.8716	High Similarity	NPC282307
0.8716	High Similarity	NPC170026
0.8707	High Similarity	NPC250557
0.8707	High Similarity	NPC141212
0.8707	High Similarity	NPC93552
0.8707	High Similarity	NPC246328
0.8707	High Similarity	NPC469550
0.8707	High Similarity	NPC27532
0.8707	High Similarity	NPC325028
0.8707	High Similarity	NPC256346
0.8705	High Similarity	NPC209560
0.8705	High Similarity	NPC294409
0.8705	High Similarity	NPC181124
0.8705	High Similarity	NPC116632
0.8705	High Similarity	NPC303644
0.8705	High Similarity	NPC7013
0.8705	High Similarity	NPC162680
0.8699	High Similarity	NPC154345
0.8699	High Similarity	NPC260895
0.8699	High Similarity	NPC31363
0.8699	High Similarity	NPC204515
0.8699	High Similarity	NPC302783
0.8699	High Similarity	NPC144283
0.8699	High Similarity	NPC262623
0.8699	High Similarity	NPC473201
0.869	High Similarity	NPC287101
0.869	High Similarity	NPC223579
0.869	High Similarity	NPC270465
0.869	High Similarity	NPC183950
0.869	High Similarity	NPC137062
0.869	High Similarity	NPC87125
0.869	High Similarity	NPC52005
0.8681	High Similarity	NPC77378
0.8681	High Similarity	NPC275772
0.8681	High Similarity	NPC130230
0.8681	High Similarity	NPC239312
0.8662	High Similarity	NPC119663
0.8652	High Similarity	NPC110419
0.8649	High Similarity	NPC234255
0.8649	High Similarity	NPC134287
0.8649	High Similarity	NPC130589
0.8647	High Similarity	NPC474264
0.8643	High Similarity	NPC278323
0.8643	High Similarity	NPC309154
0.8643	High Similarity	NPC90665
0.8643	High Similarity	NPC279668
0.8643	High Similarity	NPC55162
0.8643	High Similarity	NPC12175
0.8643	High Similarity	NPC474784
0.8639	High Similarity	NPC104728
0.8639	High Similarity	NPC302950
0.8639	High Similarity	NPC149889
0.8639	High Similarity	NPC246162
0.8639	High Similarity	NPC312338
0.8639	High Similarity	NPC260979
0.8639	High Similarity	NPC260491
0.8639	High Similarity	NPC257648
0.8639	High Similarity	NPC60972
0.8639	High Similarity	NPC39732
0.8639	High Similarity	NPC35544
0.8639	High Similarity	NPC472912
0.8639	High Similarity	NPC236637
0.8639	High Similarity	NPC36835
0.8639	High Similarity	NPC240476
0.8639	High Similarity	NPC55205
0.8639	High Similarity	NPC219582
0.8639	High Similarity	NPC61506
0.8639	High Similarity	NPC9743
0.8639	High Similarity	NPC474993
0.8639	High Similarity	NPC477231
0.8639	High Similarity	NPC237994
0.863	High Similarity	NPC184136
0.863	High Similarity	NPC3825
0.863	High Similarity	NPC286342
0.863	High Similarity	NPC88804
0.863	High Similarity	NPC45873
0.863	High Similarity	NPC239363
0.863	High Similarity	NPC188871
0.863	High Similarity	NPC62042
0.863	High Similarity	NPC472279
0.863	High Similarity	NPC149127
0.8621	High Similarity	NPC120464
0.8621	High Similarity	NPC276930
0.8621	High Similarity	NPC194856
0.8613	High Similarity	NPC294226
0.8611	High Similarity	NPC143903
0.8611	High Similarity	NPC226987
0.8611	High Similarity	NPC169749
0.8605	High Similarity	NPC201284
0.8601	High Similarity	NPC105213
0.8601	High Similarity	NPC95751
0.8601	High Similarity	NPC207732
0.86	High Similarity	NPC184755
0.86	High Similarity	NPC74178
0.8593	High Similarity	NPC304622
0.8593	High Similarity	NPC261759
0.8592	High Similarity	NPC169214
0.8592	High Similarity	NPC176030
0.8592	High Similarity	NPC229218
0.8592	High Similarity	NPC185607
0.8592	High Similarity	NPC141817
0.8592	High Similarity	NPC312256
0.8592	High Similarity	NPC192597
0.8591	High Similarity	NPC472455
0.8591	High Similarity	NPC474638

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 NPC324929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	485
0.1-0.2	1006
0.2-0.3	1666
0.3-0.4	2664
0.4-0.5	1751
0.5-0.6	1055
0.6-0.7	379
0.7-0.8	115
0.8-0.85	20
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8865	High Similarity	NPD1511	Approved
0.8832	High Similarity	NPD1510	Phase 2
0.8741	High Similarity	NPD1512	Approved
0.8639	High Similarity	NPD1934	Approved
0.8581	High Similarity	NPD2393	Clinical (unspecified phase)
0.854	High Similarity	NPD943	Approved
0.8456	Intermediate Similarity	NPD2801	Approved
0.8444	Intermediate Similarity	NPD9494	Approved
0.8406	Intermediate Similarity	NPD1240	Approved
0.838	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD3882	Suspended
0.831	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD1607	Approved
0.8255	Intermediate Similarity	NPD4380	Phase 2
0.8239	Intermediate Similarity	NPD2935	Discontinued
0.8217	Intermediate Similarity	NPD3818	Discontinued
0.8148	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD2798	Approved
0.8089	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6166	Phase 2
0.8089	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD2344	Approved
0.8041	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD2313	Discontinued
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2796	Approved
0.7937	Intermediate Similarity	NPD7054	Approved
0.7935	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1203	Approved
0.7888	Intermediate Similarity	NPD7472	Approved
0.7888	Intermediate Similarity	NPD7074	Phase 3
0.7877	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6797	Phase 2
0.7838	Intermediate Similarity	NPD2309	Approved
0.7832	Intermediate Similarity	NPD447	Suspended
0.7823	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7075	Discontinued
0.78	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD2799	Discontinued
0.7793	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7251	Discontinued
0.777	Intermediate Similarity	NPD1470	Approved
0.7744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7819	Suspended
0.7742	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1201	Approved
0.7736	Intermediate Similarity	NPD6232	Discontinued
0.7733	Intermediate Similarity	NPD6799	Approved
0.7708	Intermediate Similarity	NPD230	Phase 1
0.7702	Intermediate Similarity	NPD7473	Discontinued
0.7687	Intermediate Similarity	NPD2346	Discontinued
0.7681	Intermediate Similarity	NPD3972	Approved
0.7677	Intermediate Similarity	NPD6801	Discontinued
0.7651	Intermediate Similarity	NPD3750	Approved
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7636	Intermediate Similarity	NPD7808	Phase 3
0.763	Intermediate Similarity	NPD5536	Phase 2
0.7628	Intermediate Similarity	NPD1465	Phase 2
0.7619	Intermediate Similarity	NPD1551	Phase 2
0.7616	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7411	Suspended
0.761	Intermediate Similarity	NPD5494	Approved
0.7597	Intermediate Similarity	NPD7458	Discontinued
0.7586	Intermediate Similarity	NPD1933	Approved
0.758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD228	Approved
0.7556	Intermediate Similarity	NPD9493	Approved
0.7556	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD9717	Approved
0.7551	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6599	Discontinued
0.7547	Intermediate Similarity	NPD919	Approved
0.7533	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1613	Approved
0.7517	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5403	Approved
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5402	Approved
0.7466	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1241	Discontinued
0.7453	Intermediate Similarity	NPD1247	Approved
0.7451	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5401	Approved
0.7447	Intermediate Similarity	NPD1876	Approved
0.7445	Intermediate Similarity	NPD9545	Approved
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7417	Intermediate Similarity	NPD8166	Discontinued
0.7413	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1164	Approved
0.7379	Intermediate Similarity	NPD3268	Approved
0.7379	Intermediate Similarity	NPD411	Approved
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7375	Intermediate Similarity	NPD3749	Approved
0.7368	Intermediate Similarity	NPD6190	Approved
0.7346	Intermediate Similarity	NPD6959	Discontinued
0.7342	Intermediate Similarity	NPD6844	Discontinued
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7324	Intermediate Similarity	NPD1283	Approved
0.732	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3748	Approved
0.7312	Intermediate Similarity	NPD7768	Phase 2
0.731	Intermediate Similarity	NPD3027	Phase 3
0.7305	Intermediate Similarity	NPD1608	Approved
0.7305	Intermediate Similarity	NPD9269	Phase 2
0.7303	Intermediate Similarity	NPD7003	Approved
0.7289	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD2797	Approved
0.7266	Intermediate Similarity	NPD1651	Approved
0.7262	Intermediate Similarity	NPD6559	Discontinued
0.7261	Intermediate Similarity	NPD3455	Phase 2
0.726	Intermediate Similarity	NPD3764	Approved
0.7256	Intermediate Similarity	NPD3926	Phase 2
0.7255	Intermediate Similarity	NPD2354	Approved
0.725	Intermediate Similarity	NPD2296	Approved
0.7244	Intermediate Similarity	NPD920	Approved
0.7237	Intermediate Similarity	NPD1243	Approved
0.723	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD2533	Approved
0.7226	Intermediate Similarity	NPD4661	Approved
0.7226	Intermediate Similarity	NPD2534	Approved
0.7226	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4662	Approved
0.7226	Intermediate Similarity	NPD2532	Approved
0.7206	Intermediate Similarity	NPD5283	Phase 1
0.72	Intermediate Similarity	NPD7033	Discontinued
0.7183	Intermediate Similarity	NPD1481	Phase 2
0.7181	Intermediate Similarity	NPD6651	Approved
0.7164	Intermediate Similarity	NPD3021	Approved
0.7164	Intermediate Similarity	NPD3022	Approved
0.7162	Intermediate Similarity	NPD4307	Phase 2
0.7162	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD7685	Pre-registration
0.7153	Intermediate Similarity	NPD3266	Approved
0.7153	Intermediate Similarity	NPD3267	Approved
0.7152	Intermediate Similarity	NPD824	Approved
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2800	Approved
0.7113	Intermediate Similarity	NPD1281	Approved
0.7113	Intermediate Similarity	NPD1535	Discovery
0.7105	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1019	Discontinued
0.7097	Intermediate Similarity	NPD3300	Phase 2
0.7093	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD17	Approved
0.709	Intermediate Similarity	NPD74	Approved
0.709	Intermediate Similarity	NPD9266	Approved
0.7083	Intermediate Similarity	NPD3225	Approved
0.7071	Intermediate Similarity	NPD1894	Discontinued
0.7071	Intermediate Similarity	NPD1548	Phase 1
0.707	Intermediate Similarity	NPD6273	Approved
0.7063	Intermediate Similarity	NPD6385	Approved
0.7063	Intermediate Similarity	NPD6386	Approved
0.7051	Intermediate Similarity	NPD7390	Discontinued
0.7037	Intermediate Similarity	NPD5978	Approved
0.7037	Intermediate Similarity	NPD5977	Approved
0.7032	Intermediate Similarity	NPD3887	Approved
0.7032	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3751	Discontinued
0.7021	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9268	Approved
0.7019	Intermediate Similarity	NPD6280	Approved
0.7019	Intermediate Similarity	NPD6279	Approved
0.7018	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9264	Approved
0.7015	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9263	Approved
0.7015	Intermediate Similarity	NPD9267	Approved
0.7014	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1610	Phase 2
0.6993	Remote Similarity	NPD2353	Approved
0.6993	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7440	Discontinued
0.6981	Remote Similarity	NPD1653	Approved
0.698	Remote Similarity	NPD6233	Phase 2
0.6977	Remote Similarity	NPD8313	Approved
0.6977	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8312	Approved
0.6972	Remote Similarity	NPD4626	Approved
0.6968	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4110	Phase 3
0.6962	Remote Similarity	NPD5049	Phase 3

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