NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.05
Volume:	206.86
LogP:	3.012
LogD:	3.161
LogS:	-4.844
# Rotatable Bonds:	0
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	1.608
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.76
MDCK Permeability:	2.3562686692457646e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.294
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	92.16091918945312%
Volume Distribution (VD):	0.389
Pgp-substrate:	5.260498523712158%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.564
CYP2C19-inhibitor:	0.796
CYP2C19-substrate:	0.318
CYP2C9-inhibitor:	0.406
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.116
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	1.716
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.169
Human Hepatotoxicity (H-HT):	0.529
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.18
Rat Oral Acute Toxicity:	0.218
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.894
Carcinogencity:	0.85
Eye Corrosion:	0.4
Eye Irritation:	0.993
Respiratory Toxicity:	0.43

Download Data

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

Natural Product: NPC107846

Natural Product ID:	NPC107846
*Common Name:**	Benzo[C]Chromen-6-One
IUPAC Name:	benzo[c]chromen-6-one
Synonyms:	Benzo[C]Chromen-6-One
Standard InCHIKey:	TVKNXKLYVUVOCV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O2/c14-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)15-13/h1-8H
SMILES:	O=c1oc2ccccc2c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL6355
PubChem CID:	16173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s11306-014-0728-9]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/sdata.2014.29]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11171227]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12576668]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	seed	n.a.	PMID[25891114]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	Database[MetaboLights]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO882	Trogopterus xanthipes	Species	Sciuridae	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	1

Activity Type	# Activity
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1567	Protein Complex	DNA gyrase	Escherichia coli K-12	IC50	>	500.0	ug.mL-1	PMID[547074]

☑ 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 NPC107846 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	690
0.1-0.2	2437
0.2-0.3	5631
0.3-0.4	12107
0.4-0.5	4979
0.5-0.6	6861
0.6-0.7	7712
0.7-0.8	2142
0.8-0.85	103
0.85-0.9	30
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8843	High Similarity	NPC35744
0.8803	High Similarity	NPC233238
0.8797	High Similarity	NPC254994
0.8629	High Similarity	NPC314329
0.8618	High Similarity	NPC246214
0.8607	High Similarity	NPC32298
0.8595	High Similarity	NPC470860
0.8537	High Similarity	NPC54243
0.8525	High Similarity	NPC45104
0.8478	Intermediate Similarity	NPC131766
0.8409	Intermediate Similarity	NPC287533
0.8359	Intermediate Similarity	NPC165556
0.8321	Intermediate Similarity	NPC109778
0.832	Intermediate Similarity	NPC230951
0.8309	Intermediate Similarity	NPC476191
0.8281	Intermediate Similarity	NPC89630
0.8244	Intermediate Similarity	NPC238309
0.824	Intermediate Similarity	NPC201284
0.824	Intermediate Similarity	NPC264976
0.8235	Intermediate Similarity	NPC103001
0.8231	Intermediate Similarity	NPC161322
0.8231	Intermediate Similarity	NPC37512
0.8226	Intermediate Similarity	NPC469954
0.8214	Intermediate Similarity	NPC32470
0.8203	Intermediate Similarity	NPC93730
0.8201	Intermediate Similarity	NPC472840
0.8195	Intermediate Similarity	NPC183103
0.8182	Intermediate Similarity	NPC473271
0.8182	Intermediate Similarity	NPC79496
0.8182	Intermediate Similarity	NPC2989
0.8168	Intermediate Similarity	NPC2401
0.8156	Intermediate Similarity	NPC267509
0.8154	Intermediate Similarity	NPC177925
0.8154	Intermediate Similarity	NPC237868
0.814	Intermediate Similarity	NPC193805
0.8136	Intermediate Similarity	NPC139891
0.8134	Intermediate Similarity	NPC470406
0.8125	Intermediate Similarity	NPC311219
0.8116	Intermediate Similarity	NPC136095
0.8106	Intermediate Similarity	NPC473019
0.8106	Intermediate Similarity	NPC66246
0.8106	Intermediate Similarity	NPC170546
0.808	Intermediate Similarity	NPC217423
0.8077	Intermediate Similarity	NPC2771
0.8077	Intermediate Similarity	NPC88403
0.8065	Intermediate Similarity	NPC220540
0.8065	Intermediate Similarity	NPC188907
0.8062	Intermediate Similarity	NPC11799
0.8062	Intermediate Similarity	NPC141252
0.8051	Intermediate Similarity	NPC114594
0.8045	Intermediate Similarity	NPC183348
0.8045	Intermediate Similarity	NPC278787
0.8045	Intermediate Similarity	NPC327457
0.8045	Intermediate Similarity	NPC86774
0.8045	Intermediate Similarity	NPC282230
0.8033	Intermediate Similarity	NPC23332
0.8031	Intermediate Similarity	NPC474874
0.803	Intermediate Similarity	NPC125887
0.8029	Intermediate Similarity	NPC471542
0.8017	Intermediate Similarity	NPC259554
0.8016	Intermediate Similarity	NPC206007
0.8015	Intermediate Similarity	NPC474737
0.8015	Intermediate Similarity	NPC66705
0.8015	Intermediate Similarity	NPC470844
0.8015	Intermediate Similarity	NPC298900
0.8014	Intermediate Similarity	NPC308006
0.8	Intermediate Similarity	NPC24075
0.8	Intermediate Similarity	NPC470163
0.8	Intermediate Similarity	NPC470162
0.8	Intermediate Similarity	NPC316062
0.8	Intermediate Similarity	NPC189773
0.7985	Intermediate Similarity	NPC470977
0.7985	Intermediate Similarity	NPC15083
0.7985	Intermediate Similarity	NPC141549
0.7985	Intermediate Similarity	NPC196979
0.7985	Intermediate Similarity	NPC470976
0.7985	Intermediate Similarity	NPC279596
0.7984	Intermediate Similarity	NPC69403
0.7984	Intermediate Similarity	NPC291189
0.7984	Intermediate Similarity	NPC46634
0.7984	Intermediate Similarity	NPC252004
0.7983	Intermediate Similarity	NPC209632
0.7956	Intermediate Similarity	NPC9985
0.7956	Intermediate Similarity	NPC239495
0.7955	Intermediate Similarity	NPC298884
0.7955	Intermediate Similarity	NPC22783
0.7955	Intermediate Similarity	NPC428300
0.7953	Intermediate Similarity	NPC137710
0.7951	Intermediate Similarity	NPC183648
0.7945	Intermediate Similarity	NPC24232
0.7941	Intermediate Similarity	NPC292998
0.7941	Intermediate Similarity	NPC311339
0.7939	Intermediate Similarity	NPC470858
0.7939	Intermediate Similarity	NPC4164
0.7939	Intermediate Similarity	NPC224657
0.7931	Intermediate Similarity	NPC470107
0.7931	Intermediate Similarity	NPC194379
0.7929	Intermediate Similarity	NPC220106
0.7926	Intermediate Similarity	NPC284424
0.792	Intermediate Similarity	NPC51345
0.791	Intermediate Similarity	NPC228184
0.791	Intermediate Similarity	NPC245395
0.7903	Intermediate Similarity	NPC279916
0.7902	Intermediate Similarity	NPC473927
0.7899	Intermediate Similarity	NPC186647
0.7895	Intermediate Similarity	NPC2596
0.7895	Intermediate Similarity	NPC50583
0.7895	Intermediate Similarity	NPC196034
0.7887	Intermediate Similarity	NPC260152
0.7887	Intermediate Similarity	NPC290038
0.7883	Intermediate Similarity	NPC125269
0.7877	Intermediate Similarity	NPC227166
0.7874	Intermediate Similarity	NPC152159
0.7872	Intermediate Similarity	NPC105648
0.7872	Intermediate Similarity	NPC254010
0.7869	Intermediate Similarity	NPC149545
0.7863	Intermediate Similarity	NPC221798
0.7863	Intermediate Similarity	NPC229113
0.7862	Intermediate Similarity	NPC300983
0.7857	Intermediate Similarity	NPC262635
0.7857	Intermediate Similarity	NPC473209
0.7852	Intermediate Similarity	NPC164295
0.7852	Intermediate Similarity	NPC301717
0.7852	Intermediate Similarity	NPC239134
0.7842	Intermediate Similarity	NPC476480
0.7842	Intermediate Similarity	NPC62735
0.7842	Intermediate Similarity	NPC84585
0.7842	Intermediate Similarity	NPC253616
0.7836	Intermediate Similarity	NPC57552
0.7832	Intermediate Similarity	NPC134621
0.7832	Intermediate Similarity	NPC29577
0.7832	Intermediate Similarity	NPC208584
0.7826	Intermediate Similarity	NPC163029
0.7826	Intermediate Similarity	NPC99854
0.7823	Intermediate Similarity	NPC41326
0.782	Intermediate Similarity	NPC41721
0.782	Intermediate Similarity	NPC293387
0.7817	Intermediate Similarity	NPC313036
0.7812	Intermediate Similarity	NPC61779
0.781	Intermediate Similarity	NPC57601
0.7808	Intermediate Similarity	NPC473466
0.7808	Intermediate Similarity	NPC474660
0.7805	Intermediate Similarity	NPC210089
0.7801	Intermediate Similarity	NPC275734
0.7801	Intermediate Similarity	NPC474037
0.7795	Intermediate Similarity	NPC228318
0.7794	Intermediate Similarity	NPC278556
0.7794	Intermediate Similarity	NPC307289
0.7793	Intermediate Similarity	NPC472839
0.7787	Intermediate Similarity	NPC99846
0.7787	Intermediate Similarity	NPC269023
0.7786	Intermediate Similarity	NPC36414
0.7786	Intermediate Similarity	NPC329225
0.7786	Intermediate Similarity	NPC147686
0.7786	Intermediate Similarity	NPC182646
0.7786	Intermediate Similarity	NPC470407
0.7786	Intermediate Similarity	NPC472888
0.7786	Intermediate Similarity	NPC473988
0.7786	Intermediate Similarity	NPC472460
0.7778	Intermediate Similarity	NPC237208
0.7778	Intermediate Similarity	NPC7569
0.7778	Intermediate Similarity	NPC211565
0.777	Intermediate Similarity	NPC301915
0.777	Intermediate Similarity	NPC268081
0.777	Intermediate Similarity	NPC254741
0.777	Intermediate Similarity	NPC261292
0.7769	Intermediate Similarity	NPC37622
0.7769	Intermediate Similarity	NPC1065
0.7769	Intermediate Similarity	NPC30594
0.7762	Intermediate Similarity	NPC95123
0.7762	Intermediate Similarity	NPC66404
0.776	Intermediate Similarity	NPC53953
0.7754	Intermediate Similarity	NPC172262
0.7752	Intermediate Similarity	NPC168050
0.7752	Intermediate Similarity	NPC233282
0.7752	Intermediate Similarity	NPC470092
0.7744	Intermediate Similarity	NPC474264
0.7744	Intermediate Similarity	NPC475236
0.7742	Intermediate Similarity	NPC212415
0.7742	Intermediate Similarity	NPC57879
0.774	Intermediate Similarity	NPC70764
0.774	Intermediate Similarity	NPC472837
0.774	Intermediate Similarity	NPC474648
0.7737	Intermediate Similarity	NPC472524
0.7737	Intermediate Similarity	NPC101294
0.7737	Intermediate Similarity	NPC66158
0.7737	Intermediate Similarity	NPC473655
0.7734	Intermediate Similarity	NPC171023
0.7734	Intermediate Similarity	NPC293424
0.773	Intermediate Similarity	NPC261234
0.773	Intermediate Similarity	NPC473499
0.773	Intermediate Similarity	NPC316480
0.773	Intermediate Similarity	NPC11566
0.7727	Intermediate Similarity	NPC30216
0.7727	Intermediate Similarity	NPC91475
0.7727	Intermediate Similarity	NPC56332
0.7727	Intermediate Similarity	NPC265910
0.7727	Intermediate Similarity	NPC111088
0.7724	Intermediate Similarity	NPC12305
0.7724	Intermediate Similarity	NPC142863

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 NPC107846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	540
0.1-0.2	987
0.2-0.3	1389
0.3-0.4	2757
0.4-0.5	1972
0.5-0.6	1070
0.6-0.7	321
0.7-0.8	96
0.8-0.85	13
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8629	High Similarity	NPD1547	Clinical (unspecified phase)
0.8504	High Similarity	NPD3266	Approved
0.8504	High Similarity	NPD3267	Approved
0.8359	Intermediate Similarity	NPD1203	Approved
0.8359	Intermediate Similarity	NPD2797	Approved
0.8358	Intermediate Similarity	NPD3748	Approved
0.8333	Intermediate Similarity	NPD4307	Phase 2
0.832	Intermediate Similarity	NPD17	Approved
0.8308	Intermediate Similarity	NPD6832	Phase 2
0.8235	Intermediate Similarity	NPD2346	Discontinued
0.8182	Intermediate Similarity	NPD3268	Approved
0.8182	Intermediate Similarity	NPD2313	Discontinued
0.8136	Intermediate Similarity	NPD9697	Approved
0.8125	Intermediate Similarity	NPD1608	Approved
0.8125	Intermediate Similarity	NPD9717	Approved
0.8088	Intermediate Similarity	NPD4308	Phase 3
0.8058	Intermediate Similarity	NPD3750	Approved
0.8015	Intermediate Similarity	NPD2798	Approved
0.8	Intermediate Similarity	NPD1933	Approved
0.7986	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3972	Approved
0.7956	Intermediate Similarity	NPD2799	Discontinued
0.7907	Intermediate Similarity	NPD1281	Approved
0.7907	Intermediate Similarity	NPD1611	Approved
0.7903	Intermediate Similarity	NPD1241	Discontinued
0.7879	Intermediate Similarity	NPD1019	Discontinued
0.7868	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD3225	Approved
0.7863	Intermediate Similarity	NPD1876	Approved
0.7862	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1243	Approved
0.7852	Intermediate Similarity	NPD3749	Approved
0.7842	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD2344	Approved
0.7823	Intermediate Similarity	NPD5535	Approved
0.7801	Intermediate Similarity	NPD7003	Approved
0.7786	Intermediate Similarity	NPD1549	Phase 2
0.7786	Intermediate Similarity	NPD2897	Discontinued
0.777	Intermediate Similarity	NPD2796	Approved
0.777	Intermediate Similarity	NPD7819	Suspended
0.7742	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD4622	Approved
0.7737	Intermediate Similarity	NPD4618	Approved
0.7727	Intermediate Similarity	NPD1283	Approved
0.7714	Intermediate Similarity	NPD2353	Approved
0.7714	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1471	Phase 3
0.7714	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4628	Phase 3
0.7655	Intermediate Similarity	NPD6273	Approved
0.7651	Intermediate Similarity	NPD1465	Phase 2
0.7647	Intermediate Similarity	NPD3764	Approved
0.7626	Intermediate Similarity	NPD5688	Approved
0.7626	Intermediate Similarity	NPD5689	Approved
0.7622	Intermediate Similarity	NPD2309	Approved
0.7597	Intermediate Similarity	NPD1894	Discontinued
0.7591	Intermediate Similarity	NPD8032	Phase 2
0.7586	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1481	Phase 2
0.7563	Intermediate Similarity	NPD1238	Approved
0.7538	Intermediate Similarity	NPD1651	Approved
0.7536	Intermediate Similarity	NPD1240	Approved
0.7518	Intermediate Similarity	NPD6798	Discontinued
0.7518	Intermediate Similarity	NPD4477	Approved
0.7518	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1551	Phase 2
0.7518	Intermediate Similarity	NPD1296	Phase 2
0.7518	Intermediate Similarity	NPD4476	Approved
0.7518	Intermediate Similarity	NPD411	Approved
0.7517	Intermediate Similarity	NPD6799	Approved
0.7517	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD3887	Approved
0.75	Intermediate Similarity	NPD2354	Approved
0.75	Intermediate Similarity	NPD1535	Discovery
0.7483	Intermediate Similarity	NPD920	Approved
0.7482	Intermediate Similarity	NPD447	Suspended
0.7466	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD9545	Approved
0.745	Intermediate Similarity	NPD6599	Discontinued
0.7447	Intermediate Similarity	NPD1510	Phase 2
0.7442	Intermediate Similarity	NPD9493	Approved
0.7429	Intermediate Similarity	NPD1607	Approved
0.7417	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2979	Phase 3
0.741	Intermediate Similarity	NPD3142	Approved
0.741	Intermediate Similarity	NPD3140	Approved
0.7405	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD5691	Approved
0.7405	Intermediate Similarity	NPD5585	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7381	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD9261	Approved
0.7368	Intermediate Similarity	NPD4288	Approved
0.7357	Intermediate Similarity	NPD6355	Discontinued
0.7347	Intermediate Similarity	NPD5401	Approved
0.7333	Intermediate Similarity	NPD6585	Discontinued
0.7324	Intermediate Similarity	NPD7033	Discontinued
0.7317	Intermediate Similarity	NPD164	Approved
0.7285	Intermediate Similarity	NPD5890	Approved
0.7285	Intermediate Similarity	NPD5889	Approved
0.7279	Intermediate Similarity	NPD1164	Approved
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.726	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7427	Discontinued
0.7248	Intermediate Similarity	NPD5403	Approved
0.7239	Intermediate Similarity	NPD1201	Approved
0.7239	Intermediate Similarity	NPD422	Phase 1
0.7237	Intermediate Similarity	NPD6801	Discontinued
0.7234	Intermediate Similarity	NPD1184	Approved
0.7233	Intermediate Similarity	NPD7177	Discontinued
0.723	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2182	Approved
0.7218	Intermediate Similarity	NPD4626	Approved
0.7218	Intermediate Similarity	NPD1778	Approved
0.7215	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7440	Discontinued
0.7208	Intermediate Similarity	NPD7768	Phase 2
0.7208	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3134	Approved
0.7192	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5049	Phase 3
0.7162	Intermediate Similarity	NPD1511	Approved
0.7153	Intermediate Similarity	NPD2438	Suspended
0.7153	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD6099	Approved
0.7153	Intermediate Similarity	NPD2531	Phase 2
0.7153	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD1202	Approved
0.7143	Intermediate Similarity	NPD9267	Approved
0.7143	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD9264	Approved
0.7143	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9263	Approved
0.7132	Intermediate Similarity	NPD4359	Approved
0.7124	Intermediate Similarity	NPD6280	Approved
0.7124	Intermediate Similarity	NPD6279	Approved
0.7122	Intermediate Similarity	NPD2614	Approved
0.7115	Intermediate Similarity	NPD919	Approved
0.7099	Intermediate Similarity	NPD709	Approved
0.7092	Intermediate Similarity	NPD6233	Phase 2
0.7089	Intermediate Similarity	NPD6808	Phase 2
0.7087	Intermediate Similarity	NPD9266	Approved
0.7087	Intermediate Similarity	NPD74	Approved
0.7071	Intermediate Similarity	NPD7095	Approved
0.7067	Intermediate Similarity	NPD1512	Approved
0.7051	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4060	Phase 1
0.704	Intermediate Similarity	NPD5909	Discontinued
0.7037	Intermediate Similarity	NPD3847	Discontinued
0.7037	Intermediate Similarity	NPD3496	Discontinued
0.7032	Intermediate Similarity	NPD2296	Approved
0.7032	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3817	Phase 2
0.702	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3444	Approved
0.7015	Intermediate Similarity	NPD3443	Approved
0.7015	Intermediate Similarity	NPD3445	Approved
0.7013	Intermediate Similarity	NPD7577	Discontinued
0.7013	Intermediate Similarity	NPD1934	Approved
0.7	Intermediate Similarity	NPD4662	Approved
0.7	Intermediate Similarity	NPD4661	Approved
0.7	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4380	Phase 2
0.6992	Remote Similarity	NPD7644	Approved
0.6985	Remote Similarity	NPD1610	Phase 2
0.6981	Remote Similarity	NPD6232	Discontinued
0.6972	Remote Similarity	NPD4062	Phase 3
0.6968	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5494	Approved
0.695	Remote Similarity	NPD4625	Phase 3
0.6948	Remote Similarity	NPD2366	Approved
0.6943	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD454	Approved
0.6929	Remote Similarity	NPD968	Approved
0.6928	Remote Similarity	NPD2649	Approved
0.6928	Remote Similarity	NPD2651	Approved
0.6923	Remote Similarity	NPD4140	Approved
0.6923	Remote Similarity	NPD5402	Approved
0.6918	Remote Similarity	NPD5406	Approved
0.6918	Remote Similarity	NPD5408	Approved
0.6918	Remote Similarity	NPD6959	Discontinued
0.6918	Remote Similarity	NPD5404	Approved
0.6918	Remote Similarity	NPD5405	Approved
0.6914	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5951	Approved
0.6894	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4287	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