NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.05
Volume:	265.186
LogP:	2.555
LogD:	2.555
LogS:	-3.477
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.333
Fsp3:	0.0
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:	-4.726
MDCK Permeability:	8.664170309202746e-06
Pgp-inhibitor:	0.014
Pgp-substrate:	0.716
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.85
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	96.9086685180664%
Volume Distribution (VD):	0.433
Pgp-substrate:	2.1847329139709473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.611
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.433
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.899
CYP2D6-substrate:	0.849
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	8.817
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.702
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.461
Skin Sensitization:	0.92
Carcinogencity:	0.42
Eye Corrosion:	0.017
Eye Irritation:	0.96
Respiratory Toxicity:	0.094

Download Data

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

Natural Product: NPC235428

Natural Product ID:	NPC235428
*Common Name:**	3-(2,4-Dihydroxyphenyl)-7-Hydroxychromen-4-One
IUPAC Name:	3-(2,4-dihydroxyphenyl)-7-hydroxychromen-4-one
Synonyms:
Standard InCHIKey:	ZCTNPCRBEWXCGP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O5/c16-8-1-3-10(13(18)5-8)12-7-20-14-6-9(17)2-4-11(14)15(12)19/h1-7,16-18H
SMILES:	Oc1ccc(c(c1)O)c1coc2c(c1=O)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL6694
PubChem CID:	5280520
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
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662101]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10262	Crotalaria assamica	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
IC50	6

Activity Type	# Activity
Individual Protein	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3102	Individual Protein	Beta-glucuronidase	Rattus norvegicus	IC50	>	30000.0	nM	PMID[451028]
NPT3103	Individual Protein	Lysozyme C	Rattus norvegicus	IC50	=	26300.0	nM	PMID[451028]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	=	25100.0	nM	PMID[451028]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	30000.0	nM	PMID[451028]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	30000.0	nM	PMID[451028]

☑ 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 NPC235428 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	493
0.1-0.2	1980
0.2-0.3	4673
0.3-0.4	11339
0.4-0.5	6424
0.5-0.6	4135
0.6-0.7	5719
0.7-0.8	4260
0.8-0.85	2031
0.85-0.9	1309
0.9-0.95	280
0.95-1	54

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC87545
0.9923	High Similarity	NPC234560
0.9923	High Similarity	NPC39426
0.9848	High Similarity	NPC55162
0.9848	High Similarity	NPC309154
0.9848	High Similarity	NPC279668
0.9848	High Similarity	NPC278323
0.9848	High Similarity	NPC90665
0.9848	High Similarity	NPC12175
0.9773	High Similarity	NPC209560
0.9773	High Similarity	NPC212767
0.9773	High Similarity	NPC162680
0.9773	High Similarity	NPC294409
0.9773	High Similarity	NPC181124
0.9773	High Similarity	NPC303644
0.9773	High Similarity	NPC7013
0.9773	High Similarity	NPC116632
0.9701	High Similarity	NPC101366
0.9697	High Similarity	NPC193792
0.963	High Similarity	NPC55832
0.963	High Similarity	NPC52789
0.963	High Similarity	NPC26051
0.963	High Similarity	NPC268204
0.9627	High Similarity	NPC295384
0.9556	High Similarity	NPC215311
0.9556	High Similarity	NPC204985
0.9556	High Similarity	NPC172250
0.9556	High Similarity	NPC253822
0.9556	High Similarity	NPC259166
0.9556	High Similarity	NPC219917
0.9556	High Similarity	NPC213659
0.9556	High Similarity	NPC48624
0.9556	High Similarity	NPC80962
0.9556	High Similarity	NPC326109
0.9556	High Similarity	NPC144118
0.9485	High Similarity	NPC469404
0.9481	High Similarity	NPC283429
0.9466	High Similarity	NPC313618
0.9462	High Similarity	NPC185497
0.942	High Similarity	NPC476055
0.9407	High Similarity	NPC329225
0.9407	High Similarity	NPC147686
0.9407	High Similarity	NPC472460
0.9398	High Similarity	NPC172262
0.9398	High Similarity	NPC286336
0.9394	High Similarity	NPC87231
0.9394	High Similarity	NPC257756
0.9394	High Similarity	NPC129132
0.9394	High Similarity	NPC205468
0.9394	High Similarity	NPC182428
0.9394	High Similarity	NPC212631
0.9385	High Similarity	NPC60558
0.9348	High Similarity	NPC51887
0.9348	High Similarity	NPC117836
0.9348	High Similarity	NPC242893
0.9348	High Similarity	NPC475705
0.9348	High Similarity	NPC38065
0.9348	High Similarity	NPC476178
0.9338	High Similarity	NPC201541
0.9338	High Similarity	NPC261234
0.9338	High Similarity	NPC477956
0.9338	High Similarity	NPC469523
0.9338	High Similarity	NPC316480
0.9333	High Similarity	NPC296490
0.9333	High Similarity	NPC275055
0.9333	High Similarity	NPC32441
0.9333	High Similarity	NPC84585
0.9333	High Similarity	NPC476480
0.9333	High Similarity	NPC295261
0.9333	High Similarity	NPC13768
0.9333	High Similarity	NPC250266
0.9333	High Similarity	NPC472419
0.9333	High Similarity	NPC107586
0.9333	High Similarity	NPC287246
0.9333	High Similarity	NPC12296
0.9333	High Similarity	NPC243083
0.9333	High Similarity	NPC266597
0.9333	High Similarity	NPC79943
0.9333	High Similarity	NPC290291
0.9333	High Similarity	NPC228661
0.9328	High Similarity	NPC239495
0.9328	High Similarity	NPC9985
0.9323	High Similarity	NPC28753
0.9323	High Similarity	NPC213216
0.9323	High Similarity	NPC20560
0.9323	High Similarity	NPC274121
0.9323	High Similarity	NPC263670
0.9323	High Similarity	NPC294593
0.9323	High Similarity	NPC223354
0.9323	High Similarity	NPC18877
0.9323	High Similarity	NPC242294
0.9323	High Similarity	NPC312318
0.9323	High Similarity	NPC337373
0.9323	High Similarity	NPC204960
0.9323	High Similarity	NPC56031
0.9323	High Similarity	NPC57601
0.9323	High Similarity	NPC192304
0.9323	High Similarity	NPC82225
0.9323	High Similarity	NPC78540
0.9323	High Similarity	NPC139813
0.9323	High Similarity	NPC50898
0.9323	High Similarity	NPC188646
0.9323	High Similarity	NPC159623
0.9323	High Similarity	NPC175098
0.9323	High Similarity	NPC144051
0.9323	High Similarity	NPC472365
0.9318	High Similarity	NPC64359
0.9318	High Similarity	NPC308037
0.9318	High Similarity	NPC262359
0.9286	High Similarity	NPC188074
0.9286	High Similarity	NPC125449
0.9281	High Similarity	NPC184649
0.9281	High Similarity	NPC303185
0.9281	High Similarity	NPC311741
0.9281	High Similarity	NPC234629
0.9275	High Similarity	NPC202981
0.9265	High Similarity	NPC188947
0.9265	High Similarity	NPC21350
0.9265	High Similarity	NPC99333
0.9265	High Similarity	NPC124269
0.9265	High Similarity	NPC280284
0.9265	High Similarity	NPC118813
0.9259	High Similarity	NPC47815
0.9259	High Similarity	NPC194281
0.9259	High Similarity	NPC150399
0.9259	High Similarity	NPC168105
0.9259	High Similarity	NPC213603
0.9259	High Similarity	NPC473887
0.9259	High Similarity	NPC231772
0.9259	High Similarity	NPC274109
0.9259	High Similarity	NPC186838
0.9259	High Similarity	NPC473391
0.9259	High Similarity	NPC66349
0.9259	High Similarity	NPC472364
0.9259	High Similarity	NPC98115
0.9259	High Similarity	NPC249606
0.9259	High Similarity	NPC29353
0.9259	High Similarity	NPC234133
0.9259	High Similarity	NPC12165
0.9259	High Similarity	NPC477242
0.9259	High Similarity	NPC124784
0.9259	High Similarity	NPC477244
0.9259	High Similarity	NPC41461
0.9259	High Similarity	NPC477243
0.9259	High Similarity	NPC25287
0.9259	High Similarity	NPC127447
0.9259	High Similarity	NPC1486
0.922	High Similarity	NPC218490
0.922	High Similarity	NPC266572
0.9214	High Similarity	NPC299011
0.9214	High Similarity	NPC12377
0.9209	High Similarity	NPC113770
0.9203	High Similarity	NPC3188
0.9203	High Similarity	NPC321980
0.9203	High Similarity	NPC470087
0.9203	High Similarity	NPC470089
0.9203	High Similarity	NPC110969
0.9203	High Similarity	NPC49108
0.9197	High Similarity	NPC49242
0.9197	High Similarity	NPC78913
0.9197	High Similarity	NPC329203
0.9197	High Similarity	NPC150648
0.9197	High Similarity	NPC18260
0.9197	High Similarity	NPC470211
0.9197	High Similarity	NPC274784
0.9197	High Similarity	NPC225153
0.9197	High Similarity	NPC20709
0.9197	High Similarity	NPC310135
0.9197	High Similarity	NPC265871
0.9197	High Similarity	NPC222342
0.9191	High Similarity	NPC153979
0.9191	High Similarity	NPC299379
0.9191	High Similarity	NPC188879
0.9191	High Similarity	NPC317119
0.9185	High Similarity	NPC13575
0.9185	High Similarity	NPC156092
0.9185	High Similarity	NPC131039
0.9173	High Similarity	NPC475009
0.9173	High Similarity	NPC112192
0.9173	High Similarity	NPC309717
0.9173	High Similarity	NPC164236
0.9173	High Similarity	NPC128348
0.9173	High Similarity	NPC66384
0.9173	High Similarity	NPC475008
0.9173	High Similarity	NPC189106
0.9173	High Similarity	NPC113006
0.9173	High Similarity	NPC186097
0.9173	High Similarity	NPC65060
0.9167	High Similarity	NPC247779
0.916	High Similarity	NPC186098
0.916	High Similarity	NPC80694
0.9155	High Similarity	NPC40290
0.9155	High Similarity	NPC264550
0.9155	High Similarity	NPC264289
0.9155	High Similarity	NPC195763
0.9155	High Similarity	NPC200060
0.9155	High Similarity	NPC142876
0.9155	High Similarity	NPC139293
0.9155	High Similarity	NPC317492
0.9155	High Similarity	NPC333691

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 NPC235428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	465
0.1-0.2	979
0.2-0.3	1655
0.3-0.4	2686
0.4-0.5	1810
0.5-0.6	1071
0.6-0.7	317
0.7-0.8	103
0.8-0.85	42
0.85-0.9	17
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9923	High Similarity	NPD1510	Phase 2
0.9466	High Similarity	NPD1240	Approved
0.9407	High Similarity	NPD1549	Phase 2
0.9333	High Similarity	NPD1552	Clinical (unspecified phase)
0.9333	High Similarity	NPD1550	Clinical (unspecified phase)
0.9323	High Similarity	NPD1607	Approved
0.9007	High Similarity	NPD4378	Clinical (unspecified phase)
0.8978	High Similarity	NPD2796	Approved
0.8958	High Similarity	NPD4380	Phase 2
0.8803	High Similarity	NPD1511	Approved
0.8741	High Similarity	NPD7410	Clinical (unspecified phase)
0.8681	High Similarity	NPD1512	Approved
0.86	High Similarity	NPD4381	Clinical (unspecified phase)
0.8592	High Similarity	NPD3750	Approved
0.8592	High Similarity	NPD1878	Clinical (unspecified phase)
0.8582	High Similarity	NPD970	Clinical (unspecified phase)
0.8581	High Similarity	NPD1934	Approved
0.8571	High Similarity	NPD1551	Phase 2
0.8523	High Similarity	NPD2801	Approved
0.8523	High Similarity	NPD2393	Clinical (unspecified phase)
0.8514	High Similarity	NPD7411	Suspended
0.8478	Intermediate Similarity	NPD943	Approved
0.8477	Intermediate Similarity	NPD7075	Discontinued
0.8467	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD6799	Approved
0.8411	Intermediate Similarity	NPD3882	Suspended
0.84	Intermediate Similarity	NPD7819	Suspended
0.84	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.828	Intermediate Similarity	NPD3818	Discontinued
0.8243	Intermediate Similarity	NPD920	Approved
0.8239	Intermediate Similarity	NPD3748	Approved
0.8239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD2935	Discontinued
0.817	Intermediate Similarity	NPD7768	Phase 2
0.8153	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2800	Approved
0.8138	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1243	Approved
0.8125	Intermediate Similarity	NPD2344	Approved
0.8121	Intermediate Similarity	NPD5403	Approved
0.8108	Intermediate Similarity	NPD5401	Approved
0.8105	Intermediate Similarity	NPD3817	Phase 2
0.8102	Intermediate Similarity	NPD1203	Approved
0.8099	Intermediate Similarity	NPD6651	Approved
0.8074	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD2313	Discontinued
0.8052	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1548	Phase 1
0.8043	Intermediate Similarity	NPD2798	Approved
0.8038	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6166	Phase 2
0.8025	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD2532	Approved
0.7987	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD5402	Approved
0.7962	Intermediate Similarity	NPD6959	Discontinued
0.7941	Intermediate Similarity	NPD1610	Phase 2
0.7905	Intermediate Similarity	NPD2309	Approved
0.7901	Intermediate Similarity	NPD5953	Discontinued
0.7898	Intermediate Similarity	NPD5494	Approved
0.7888	Intermediate Similarity	NPD7054	Approved
0.7862	Intermediate Similarity	NPD2799	Discontinued
0.7842	Intermediate Similarity	NPD1470	Approved
0.784	Intermediate Similarity	NPD7472	Approved
0.784	Intermediate Similarity	NPD7074	Phase 3
0.7805	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD9545	Approved
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7761	Intermediate Similarity	NPD9493	Approved
0.7754	Intermediate Similarity	NPD9717	Approved
0.7744	Intermediate Similarity	NPD7251	Discontinued
0.774	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1247	Approved
0.7722	Intermediate Similarity	NPD919	Approved
0.7718	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD7808	Phase 3
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7692	Intermediate Similarity	NPD3764	Approved
0.7681	Intermediate Similarity	NPD422	Phase 1
0.7681	Intermediate Similarity	NPD1201	Approved
0.7676	Intermediate Similarity	NPD4908	Phase 1
0.7676	Intermediate Similarity	NPD6832	Phase 2
0.7662	Intermediate Similarity	NPD3226	Approved
0.7651	Intermediate Similarity	NPD2654	Approved
0.7647	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6559	Discontinued
0.7626	Intermediate Similarity	NPD3972	Approved
0.7619	Intermediate Similarity	NPD7033	Discontinued
0.7619	Intermediate Similarity	NPD4308	Phase 3
0.7589	Intermediate Similarity	NPD1164	Approved
0.7576	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3268	Approved
0.7569	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6099	Approved
0.7568	Intermediate Similarity	NPD6100	Approved
0.7566	Intermediate Similarity	NPD7390	Discontinued
0.7532	Intermediate Similarity	NPD4288	Approved
0.7531	Intermediate Similarity	NPD3926	Phase 2
0.7518	Intermediate Similarity	NPD3225	Approved
0.7517	Intermediate Similarity	NPD2346	Discontinued
0.7483	Intermediate Similarity	NPD9494	Approved
0.7466	Intermediate Similarity	NPD1613	Approved
0.7466	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD2797	Approved
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.7448	Intermediate Similarity	NPD1296	Phase 2
0.7436	Intermediate Similarity	NPD7458	Discontinued
0.7431	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD447	Suspended
0.7407	Intermediate Similarity	NPD1241	Discontinued
0.7394	Intermediate Similarity	NPD1876	Approved
0.7376	Intermediate Similarity	NPD1608	Approved
0.7372	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5711	Approved
0.7362	Intermediate Similarity	NPD5710	Approved
0.7361	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4360	Phase 2
0.7356	Intermediate Similarity	NPD4363	Phase 3
0.7347	Intermediate Similarity	NPD4307	Phase 2
0.7343	Intermediate Similarity	NPD3267	Approved
0.7343	Intermediate Similarity	NPD3266	Approved
0.7333	Intermediate Similarity	NPD5405	Approved
0.7333	Intermediate Similarity	NPD5406	Approved
0.7333	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD5404	Approved
0.7329	Intermediate Similarity	NPD411	Approved
0.7326	Intermediate Similarity	NPD4287	Approved
0.7314	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4361	Phase 2
0.7312	Intermediate Similarity	NPD2296	Approved
0.7305	Intermediate Similarity	NPD1729	Discontinued
0.7297	Intermediate Similarity	NPD1933	Approved
0.7293	Intermediate Similarity	NPD9266	Approved
0.7293	Intermediate Similarity	NPD74	Approved
0.7292	Intermediate Similarity	NPD1019	Discontinued
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3751	Discontinued
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7273	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3027	Phase 3
0.7255	Intermediate Similarity	NPD7003	Approved
0.7254	Intermediate Similarity	NPD9269	Phase 2
0.7241	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9264	Approved
0.7218	Intermediate Similarity	NPD9267	Approved
0.7218	Intermediate Similarity	NPD9263	Approved
0.7214	Intermediate Similarity	NPD9268	Approved
0.7188	Intermediate Similarity	NPD6844	Discontinued
0.7181	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5124	Phase 1
0.7171	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD17	Approved
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.7118	Intermediate Similarity	NPD6104	Discontinued
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6190	Approved
0.7095	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6280	Approved
0.7081	Intermediate Similarity	NPD6279	Approved
0.7081	Intermediate Similarity	NPD37	Approved
0.7066	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1535	Discovery
0.7048	Intermediate Similarity	NPD3787	Discontinued
0.7048	Intermediate Similarity	NPD7229	Phase 3
0.7035	Intermediate Similarity	NPD8312	Approved
0.7035	Intermediate Similarity	NPD8313	Approved
0.7034	Intermediate Similarity	NPD1283	Approved
0.7029	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4625	Phase 3
0.7021	Intermediate Similarity	NPD1894	Discontinued
0.7019	Intermediate Similarity	NPD5890	Approved
0.7019	Intermediate Similarity	NPD5889	Approved
0.7011	Intermediate Similarity	NPD7584	Approved
0.7007	Intermediate Similarity	NPD2861	Phase 2
0.7006	Intermediate Similarity	NPD5242	Approved
0.6988	Remote Similarity	NPD7199	Phase 2
0.6987	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2354	Approved
0.6982	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD9281	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