NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	332.27
Volume:	387.546
LogP:	6.266
LogD:	1.932
LogS:	-2.707
# Rotatable Bonds:	6
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	4.412
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.619
MDCK Permeability:	9.323566700913943e-06
Pgp-inhibitor:	0.096
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.609

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.562
Plasma Protein Binding (PPB):	99.16299438476562%
Volume Distribution (VD):	2.583
Pgp-substrate:	3.7716314792633057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.409
CYP2C9-substrate:	0.736
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.22
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	14.058
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.868
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.538
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.351
Carcinogencity:	0.025
Eye Corrosion:	0.941
Eye Irritation:	0.561
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC60558

Natural Product ID:	NPC60558
*Common Name:**	7-Hydroxychromone
IUPAC Name:	7-hydroxychromen-4-one
Synonyms:	7-Hydroxychromone
Standard InCHIKey:	WVJCRTSTRGRJJT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H6O3/c10-6-1-2-7-8(11)3-4-12-9(7)5-6/h1-5,10H
SMILES:	Oc1ccc2c(c1)occc2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL58827
PubChem CID:	5409279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5140	Dipteryx odorata	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	2
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	>	10.0	ug ml-1	PMID[523647]
NPT711	Individual Protein	Aldose reductase	Bos taurus	IC50	=	137000.0	nM	PMID[523646]
NPT711	Individual Protein	Aldose reductase	Bos taurus	IC50	=	114000.0	nM	PMID[523646]
NPT711	Individual Protein	Aldose reductase	Bos taurus	Ratio	=	1.0	n.a.	PMID[523646]

☑ 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 NPC60558 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	473
0.1-0.2	2215
0.2-0.3	5826
0.3-0.4	12215
0.4-0.5	4640
0.5-0.6	4709
0.6-0.7	5829
0.7-0.8	4256
0.8-0.85	1693
0.85-0.9	680
0.9-0.95	157
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC185497
0.9603	High Similarity	NPC65060
0.9597	High Similarity	NPC186098
0.9597	High Similarity	NPC80694
0.9457	High Similarity	NPC39426
0.9457	High Similarity	NPC234560
0.9449	High Similarity	NPC308037
0.9449	High Similarity	NPC64359
0.9449	High Similarity	NPC313618
0.9385	High Similarity	NPC87545
0.9385	High Similarity	NPC235428
0.9375	High Similarity	NPC129132
0.9375	High Similarity	NPC87231
0.9375	High Similarity	NPC257756
0.9375	High Similarity	NPC212631
0.9375	High Similarity	NPC205468
0.9365	High Similarity	NPC78662
0.9365	High Similarity	NPC8005
0.936	High Similarity	NPC128428
0.936	High Similarity	NPC305518
0.9313	High Similarity	NPC162680
0.9313	High Similarity	NPC181124
0.9313	High Similarity	NPC116632
0.9313	High Similarity	NPC212767
0.9313	High Similarity	NPC303644
0.9313	High Similarity	NPC7013
0.9313	High Similarity	NPC209560
0.9313	High Similarity	NPC294409
0.9302	High Similarity	NPC472365
0.9302	High Similarity	NPC263670
0.9302	High Similarity	NPC139813
0.9302	High Similarity	NPC242294
0.9302	High Similarity	NPC312318
0.9302	High Similarity	NPC56031
0.9302	High Similarity	NPC57601
0.9302	High Similarity	NPC192304
0.9302	High Similarity	NPC188646
0.9302	High Similarity	NPC337373
0.9302	High Similarity	NPC175098
0.9302	High Similarity	NPC223457
0.9297	High Similarity	NPC262359
0.9297	High Similarity	NPC31872
0.9297	High Similarity	NPC473584
0.9297	High Similarity	NPC475589
0.9242	High Similarity	NPC12175
0.9242	High Similarity	NPC278323
0.9242	High Similarity	NPC309154
0.9242	High Similarity	NPC55162
0.9242	High Similarity	NPC279668
0.9242	High Similarity	NPC90665
0.9237	High Similarity	NPC240593
0.9237	High Similarity	NPC193792
0.9231	High Similarity	NPC164136
0.9231	High Similarity	NPC286336
0.9231	High Similarity	NPC172262
0.9225	High Similarity	NPC25937
0.9219	High Similarity	NPC5515
0.9219	High Similarity	NPC270369
0.9219	High Similarity	NPC250057
0.9213	High Similarity	NPC212379
0.9213	High Similarity	NPC69235
0.9173	High Similarity	NPC49242
0.9173	High Similarity	NPC295384
0.9167	High Similarity	NPC476480
0.9167	High Similarity	NPC84585
0.9167	High Similarity	NPC250266
0.9167	High Similarity	NPC266597
0.9167	High Similarity	NPC290291
0.9167	High Similarity	NPC188879
0.9167	High Similarity	NPC275055
0.916	High Similarity	NPC151113
0.916	High Similarity	NPC60667
0.9154	High Similarity	NPC274121
0.9154	High Similarity	NPC144051
0.9154	High Similarity	NPC28753
0.9154	High Similarity	NPC20560
0.9154	High Similarity	NPC213216
0.9154	High Similarity	NPC50898
0.9154	High Similarity	NPC18877
0.9154	High Similarity	NPC294593
0.9154	High Similarity	NPC159623
0.9154	High Similarity	NPC82225
0.9154	High Similarity	NPC204960
0.9154	High Similarity	NPC78540
0.9141	High Similarity	NPC247779
0.9141	High Similarity	NPC42292
0.9141	High Similarity	NPC307732
0.9104	High Similarity	NPC101366
0.9104	High Similarity	NPC80962
0.9104	High Similarity	NPC172250
0.9104	High Similarity	NPC215311
0.9104	High Similarity	NPC144118
0.9104	High Similarity	NPC326109
0.9104	High Similarity	NPC219917
0.9104	High Similarity	NPC48624
0.9104	High Similarity	NPC204985
0.9104	High Similarity	NPC213659
0.9104	High Similarity	NPC259166
0.9098	High Similarity	NPC280284
0.9098	High Similarity	NPC99333
0.9098	High Similarity	NPC188947
0.9098	High Similarity	NPC472460
0.9098	High Similarity	NPC329225
0.9098	High Similarity	NPC124269
0.9098	High Similarity	NPC25427
0.9098	High Similarity	NPC147686
0.9091	High Similarity	NPC186838
0.9091	High Similarity	NPC472367
0.9091	High Similarity	NPC41461
0.9091	High Similarity	NPC477244
0.9091	High Similarity	NPC25287
0.9091	High Similarity	NPC98115
0.9091	High Similarity	NPC29353
0.9091	High Similarity	NPC222633
0.9091	High Similarity	NPC477242
0.9091	High Similarity	NPC124784
0.9091	High Similarity	NPC249606
0.9091	High Similarity	NPC477243
0.9091	High Similarity	NPC150399
0.9091	High Similarity	NPC234133
0.9091	High Similarity	NPC12165
0.9091	High Similarity	NPC473391
0.9091	High Similarity	NPC472364
0.9091	High Similarity	NPC127447
0.9091	High Similarity	NPC194281
0.9091	High Similarity	NPC1486
0.9091	High Similarity	NPC476333
0.9091	High Similarity	NPC47815
0.9091	High Similarity	NPC231772
0.9091	High Similarity	NPC274109
0.9091	High Similarity	NPC168105
0.9091	High Similarity	NPC473887
0.9091	High Similarity	NPC66349
0.9084	High Similarity	NPC125920
0.9077	High Similarity	NPC10971
0.9077	High Similarity	NPC203817
0.9062	High Similarity	NPC230818
0.9048	High Similarity	NPC65041
0.9037	High Similarity	NPC52789
0.9037	High Similarity	NPC26051
0.9037	High Similarity	NPC268204
0.9037	High Similarity	NPC469404
0.9037	High Similarity	NPC55832
0.903	High Similarity	NPC470211
0.903	High Similarity	NPC23257
0.903	High Similarity	NPC261234
0.903	High Similarity	NPC283429
0.903	High Similarity	NPC201541
0.903	High Similarity	NPC469523
0.903	High Similarity	NPC473076
0.9023	High Similarity	NPC472419
0.9023	High Similarity	NPC296490
0.9023	High Similarity	NPC295261
0.9023	High Similarity	NPC79943
0.9023	High Similarity	NPC107586
0.9023	High Similarity	NPC160972
0.9023	High Similarity	NPC12296
0.9023	High Similarity	NPC243083
0.9023	High Similarity	NPC153979
0.9023	High Similarity	NPC228661
0.9023	High Similarity	NPC13768
0.9023	High Similarity	NPC317119
0.9023	High Similarity	NPC287246
0.9023	High Similarity	NPC32441
0.9023	High Similarity	NPC299379
0.9015	High Similarity	NPC13575
0.9015	High Similarity	NPC156092
0.9015	High Similarity	NPC9985
0.9015	High Similarity	NPC131039
0.9015	High Similarity	NPC239495
0.9008	High Similarity	NPC108113
0.9008	High Similarity	NPC93756
0.9	High Similarity	NPC164236
0.9	High Similarity	NPC112192
0.9	High Similarity	NPC128348
0.9	High Similarity	NPC66384
0.9	High Similarity	NPC475009
0.9	High Similarity	NPC113006
0.9	High Similarity	NPC186097
0.9	High Similarity	NPC475008
0.9	High Similarity	NPC309717
0.9	High Similarity	NPC189106
0.8992	High Similarity	NPC84772
0.8984	High Similarity	NPC293453
0.8968	High Similarity	NPC255073
0.8963	High Similarity	NPC281207
0.8963	High Similarity	NPC269652
0.8963	High Similarity	NPC253822
0.8963	High Similarity	NPC471587
0.8955	High Similarity	NPC471620
0.8955	High Similarity	NPC21350
0.8955	High Similarity	NPC118813
0.8955	High Similarity	NPC472368
0.8947	High Similarity	NPC187432
0.8947	High Similarity	NPC213603
0.8947	High Similarity	NPC281917
0.8947	High Similarity	NPC116775
0.8947	High Similarity	NPC174999
0.8947	High Similarity	NPC13408
0.8947	High Similarity	NPC187826

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 NPC60558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	469
0.1-0.2	1025
0.2-0.3	1761
0.3-0.4	2728
0.4-0.5	1716
0.5-0.6	1019
0.6-0.7	279
0.7-0.8	105
0.8-0.85	36
0.85-0.9	8
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9457	High Similarity	NPD1510	Phase 2
0.9449	High Similarity	NPD1240	Approved
0.9302	High Similarity	NPD1607	Approved
0.9098	High Similarity	NPD1549	Phase 2
0.9023	High Similarity	NPD1552	Clinical (unspecified phase)
0.9023	High Similarity	NPD1550	Clinical (unspecified phase)
0.8676	High Similarity	NPD970	Clinical (unspecified phase)
0.8667	High Similarity	NPD2796	Approved
0.8571	High Similarity	NPD4378	Clinical (unspecified phase)
0.8551	High Similarity	NPD1878	Clinical (unspecified phase)
0.8531	High Similarity	NPD4380	Phase 2
0.85	High Similarity	NPD1511	Approved
0.844	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD1551	Phase 2
0.838	Intermediate Similarity	NPD1512	Approved
0.8369	Intermediate Similarity	NPD6799	Approved
0.8298	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD7411	Suspended
0.8188	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD6651	Approved
0.8163	Intermediate Similarity	NPD1934	Approved
0.8156	Intermediate Similarity	NPD3750	Approved
0.8125	Intermediate Similarity	NPD9545	Approved
0.8121	Intermediate Similarity	NPD3882	Suspended
0.811	Intermediate Similarity	NPD9493	Approved
0.8108	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD2801	Approved
0.8085	Intermediate Similarity	NPD1243	Approved
0.8067	Intermediate Similarity	NPD7075	Discontinued
0.8054	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1203	Approved
0.8041	Intermediate Similarity	NPD6801	Discontinued
0.8029	Intermediate Similarity	NPD943	Approved
0.8027	Intermediate Similarity	NPD6599	Discontinued
0.8015	Intermediate Similarity	NPD422	Phase 1
0.8015	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7984	Intermediate Similarity	NPD1548	Phase 1
0.7958	Intermediate Similarity	NPD2800	Approved
0.7955	Intermediate Similarity	NPD9717	Approved
0.7945	Intermediate Similarity	NPD5403	Approved
0.7945	Intermediate Similarity	NPD920	Approved
0.7931	Intermediate Similarity	NPD5401	Approved
0.7879	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD2935	Discontinued
0.7832	Intermediate Similarity	NPD2654	Approved
0.7832	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3749	Approved
0.7817	Intermediate Similarity	NPD2344	Approved
0.7815	Intermediate Similarity	NPD3817	Phase 2
0.7808	Intermediate Similarity	NPD2533	Approved
0.7808	Intermediate Similarity	NPD2532	Approved
0.7808	Intermediate Similarity	NPD2534	Approved
0.7801	Intermediate Similarity	NPD3748	Approved
0.7771	Intermediate Similarity	NPD3818	Discontinued
0.7763	Intermediate Similarity	NPD7768	Phase 2
0.776	Intermediate Similarity	NPD9266	Approved
0.776	Intermediate Similarity	NPD74	Approved
0.7756	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1241	Discontinued
0.7721	Intermediate Similarity	NPD2798	Approved
0.7714	Intermediate Similarity	NPD230	Phase 1
0.768	Intermediate Similarity	NPD9267	Approved
0.768	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD9264	Approved
0.768	Intermediate Similarity	NPD9263	Approved
0.7676	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6166	Phase 2
0.7612	Intermediate Similarity	NPD1610	Phase 2
0.761	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7054	Approved
0.7609	Intermediate Similarity	NPD6832	Phase 2
0.7603	Intermediate Similarity	NPD2309	Approved
0.7582	Intermediate Similarity	NPD5402	Approved
0.7564	Intermediate Similarity	NPD6959	Discontinued
0.7562	Intermediate Similarity	NPD7472	Approved
0.7557	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3972	Approved
0.7548	Intermediate Similarity	NPD919	Approved
0.7536	Intermediate Similarity	NPD9494	Approved
0.7532	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6797	Phase 2
0.7516	Intermediate Similarity	NPD5953	Discontinued
0.7516	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD7473	Discontinued
0.7469	Intermediate Similarity	NPD7251	Discontinued
0.7464	Intermediate Similarity	NPD1019	Discontinued
0.7453	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD1247	Approved
0.7431	Intermediate Similarity	NPD2799	Discontinued
0.7423	Intermediate Similarity	NPD7808	Phase 3
0.7423	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD1164	Approved
0.7389	Intermediate Similarity	NPD5494	Approved
0.7379	Intermediate Similarity	NPD6100	Approved
0.7379	Intermediate Similarity	NPD6099	Approved
0.736	Intermediate Similarity	NPD9261	Approved
0.7353	Intermediate Similarity	NPD1201	Approved
0.7346	Intermediate Similarity	NPD1729	Discontinued
0.7343	Intermediate Similarity	NPD447	Suspended
0.7319	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD7033	Discontinued
0.7299	Intermediate Similarity	NPD9269	Phase 2
0.729	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD9281	Approved
0.7266	Intermediate Similarity	NPD2797	Approved
0.7266	Intermediate Similarity	NPD1470	Approved
0.7259	Intermediate Similarity	NPD9268	Approved
0.7256	Intermediate Similarity	NPD6559	Discontinued
0.7254	Intermediate Similarity	NPD3268	Approved
0.7237	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1876	Approved
0.7192	Intermediate Similarity	NPD4308	Phase 3
0.7188	Intermediate Similarity	NPD5711	Approved
0.7188	Intermediate Similarity	NPD5710	Approved
0.7181	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1608	Approved
0.7153	Intermediate Similarity	NPD3140	Approved
0.7153	Intermediate Similarity	NPD3142	Approved
0.7152	Intermediate Similarity	NPD7390	Discontinued
0.7152	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD846	Approved
0.7143	Intermediate Similarity	NPD940	Approved
0.7134	Intermediate Similarity	NPD4288	Approved
0.7133	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3764	Approved
0.7132	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5124	Phase 1
0.7103	Intermediate Similarity	NPD1933	Approved
0.7103	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD520	Approved
0.7073	Intermediate Similarity	NPD5844	Phase 1
0.7059	Intermediate Similarity	NPD1894	Discontinued
0.705	Intermediate Similarity	NPD1481	Phase 2
0.7034	Intermediate Similarity	NPD1613	Approved
0.7034	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7458	Discontinued
0.7025	Intermediate Similarity	NPD2296	Approved
0.7021	Intermediate Similarity	NPD3267	Approved
0.7021	Intermediate Similarity	NPD3266	Approved
0.7011	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1652	Phase 2
0.6994	Remote Similarity	NPD4363	Phase 3
0.6994	Remote Similarity	NPD4360	Phase 2
0.6993	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2346	Discontinued
0.6978	Remote Similarity	NPD1535	Discovery
0.6977	Remote Similarity	NPD9697	Approved
0.6957	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD1778	Approved
0.6954	Remote Similarity	NPD4361	Phase 2
0.6954	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7003	Approved
0.6944	Remote Similarity	NPD3027	Phase 3
0.6923	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4307	Phase 2
0.6913	Remote Similarity	NPD5406	Approved
0.6913	Remote Similarity	NPD5408	Approved
0.6913	Remote Similarity	NPD5405	Approved
0.6913	Remote Similarity	NPD5404	Approved
0.6909	Remote Similarity	NPD3751	Discontinued
0.689	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4661	Approved
0.6883	Remote Similarity	NPD4662	Approved
0.6879	Remote Similarity	NPD4749	Approved
0.6879	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1471	Phase 3
0.686	Remote Similarity	NPD4287	Approved
0.6859	Remote Similarity	NPD1653	Approved
0.6853	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1283	Approved
0.6818	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1242	Phase 1
0.6797	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2354	Approved
0.6794	Remote Similarity	NPD968	Approved
0.6794	Remote Similarity	NPD3134	Approved
0.6792	Remote Similarity	NPD6279	Approved
0.6792	Remote Similarity	NPD6844	Discontinued
0.6792	Remote Similarity	NPD6280	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