NPASS Compound

Structure

NPC472583 OpenBabel07101718292D 26 29 0 0 1 0 0 0 0 0999 V2000 -1.1248 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 25 1 0 0 0 0 10 14 1 0 0 0 0 11 21 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 15 26 1 0 0 0 0 16 25 1 0 0 0 0 17 22 2 0 0 0 0 18 19 1 0 0 0 0 18 23 1 6 0 0 0 19 20 1 0 0 0 0 19 24 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	351.9
LogP:	2.964
LogD:	2.386
LogS:	-3.816
# Rotatable Bonds:	1
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	3.38
Fsp3:	0.25
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:	-4.884
MDCK Permeability:	9.880309335130733e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	95.4596176147461%
Volume Distribution (VD):	0.566
Pgp-substrate:	3.243502140045166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.606
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.264
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.428
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.464
CYP2D6-substrate:	0.534
CYP3A4-inhibitor:	0.241
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	4.259
Half-life (T1/2):	0.394

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.394
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.432
Maximum Recommended Daily Dose:	0.712
Skin Sensitization:	0.302
Carcinogencity:	0.291
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.168

Download Data

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

Natural Product: NPC472583

Natural Product ID:	NPC472583
*Common Name:**	HRRWPOOLLFZIQU-MOPGFXCFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HRRWPOOLLFZIQU-MOPGFXCFSA-N
Standard InCHI:	InChI=1S/C20H18O6/c1-20(2)19(24)18(23)13-7-10(3-6-15(13)26-20)14-9-25-16-8-11(21)4-5-12(16)17(14)22/h3-9,18-19,21,23-24H,1-2H3/t18-,19+/m1/s1
SMILES:	CC1(C(C(C2=C(O1)C=CC(=C2)C3=COC4=C(C3=O)C=CC(=C4)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577248
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0003530] Pyranoisoflavonoids

*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
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18359631]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25710081]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3069958]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[8759164]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[550582]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[550582]

☑ 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 NPC472583 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	403
0.1-0.2	1612
0.2-0.3	3686
0.3-0.4	9177
0.4-0.5	9423
0.5-0.6	3787
0.6-0.7	5511
0.7-0.8	4603
0.8-0.85	2245
0.85-0.9	1870
0.9-0.95	341
0.95-1	39

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC7989
1.0	High Similarity	NPC223701
0.9864	High Similarity	NPC469405
0.9863	High Similarity	NPC471676
0.9863	High Similarity	NPC472422
0.9863	High Similarity	NPC244577
0.9863	High Similarity	NPC263384
0.9863	High Similarity	NPC472420
0.9797	High Similarity	NPC304207
0.9797	High Similarity	NPC48579
0.9797	High Similarity	NPC207809
0.9797	High Similarity	NPC477958
0.9797	High Similarity	NPC217706
0.9797	High Similarity	NPC470681
0.9797	High Similarity	NPC259710
0.9796	High Similarity	NPC150123
0.9796	High Similarity	NPC161881
0.9796	High Similarity	NPC10807
0.9796	High Similarity	NPC475790
0.9796	High Similarity	NPC56232
0.9796	High Similarity	NPC244583
0.973	High Similarity	NPC180301
0.973	High Similarity	NPC248793
0.9728	High Similarity	NPC209846
0.9728	High Similarity	NPC474021
0.9728	High Similarity	NPC471677
0.9728	High Similarity	NPC289774
0.9728	High Similarity	NPC477897
0.9728	High Similarity	NPC474023
0.9728	High Similarity	NPC328740
0.9664	High Similarity	NPC111341
0.9664	High Similarity	NPC304745
0.9664	High Similarity	NPC477530
0.9662	High Similarity	NPC35567
0.9662	High Similarity	NPC473996
0.9662	High Similarity	NPC476238
0.9662	High Similarity	NPC243171
0.9662	High Similarity	NPC327269
0.9662	High Similarity	NPC285623
0.9662	High Similarity	NPC171651
0.9662	High Similarity	NPC31627
0.966	High Similarity	NPC124478
0.966	High Similarity	NPC177308
0.96	High Similarity	NPC208152
0.96	High Similarity	NPC78492
0.9597	High Similarity	NPC293286
0.9597	High Similarity	NPC236756
0.9597	High Similarity	NPC326592
0.9597	High Similarity	NPC112701
0.9597	High Similarity	NPC311579
0.9597	High Similarity	NPC109594
0.9597	High Similarity	NPC268193
0.9595	High Similarity	NPC262038
0.9595	High Similarity	NPC278476
0.9595	High Similarity	NPC474772
0.9595	High Similarity	NPC472423
0.9595	High Similarity	NPC254412
0.9595	High Similarity	NPC474744
0.9595	High Similarity	NPC319910
0.9595	High Similarity	NPC472636
0.9595	High Similarity	NPC472580
0.9595	High Similarity	NPC262039
0.9595	High Similarity	NPC471675
0.9592	High Similarity	NPC472628
0.9592	High Similarity	NPC89442
0.9592	High Similarity	NPC5173
0.9589	High Similarity	NPC296998
0.9589	High Similarity	NPC23728
0.9589	High Similarity	NPC51070
0.9589	High Similarity	NPC472627
0.9589	High Similarity	NPC110303
0.9589	High Similarity	NPC85773
0.9589	High Similarity	NPC473077
0.9589	High Similarity	NPC222298
0.9539	High Similarity	NPC471976
0.9539	High Similarity	NPC475784
0.9533	High Similarity	NPC476169
0.953	High Similarity	NPC216035
0.953	High Similarity	NPC477957
0.953	High Similarity	NPC138288
0.953	High Similarity	NPC256141
0.953	High Similarity	NPC217149
0.9527	High Similarity	NPC472421
0.9527	High Similarity	NPC472633
0.9527	High Similarity	NPC105136
0.9527	High Similarity	NPC61258
0.9524	High Similarity	NPC132592
0.9524	High Similarity	NPC10097
0.9524	High Similarity	NPC160821
0.9524	High Similarity	NPC6511
0.9521	High Similarity	NPC472629
0.9521	High Similarity	NPC195621
0.9521	High Similarity	NPC54577
0.9521	High Similarity	NPC83357
0.9521	High Similarity	NPC176229
0.9521	High Similarity	NPC214774
0.9521	High Similarity	NPC301276
0.9521	High Similarity	NPC142405
0.9521	High Similarity	NPC88964
0.9521	High Similarity	NPC267375
0.9521	High Similarity	NPC20488
0.9521	High Similarity	NPC312973
0.9521	High Similarity	NPC475052
0.9521	High Similarity	NPC67805
0.9521	High Similarity	NPC246948
0.9521	High Similarity	NPC474302
0.9521	High Similarity	NPC111786
0.9521	High Similarity	NPC316769
0.9521	High Similarity	NPC470647
0.9477	High Similarity	NPC3629
0.9477	High Similarity	NPC474038
0.947	High Similarity	NPC215917
0.947	High Similarity	NPC20530
0.947	High Similarity	NPC10754
0.9467	High Similarity	NPC88983
0.9467	High Similarity	NPC20907
0.9467	High Similarity	NPC244250
0.9459	High Similarity	NPC139966
0.9459	High Similarity	NPC307052
0.9456	High Similarity	NPC237635
0.9456	High Similarity	NPC470670
0.9456	High Similarity	NPC79469
0.9456	High Similarity	NPC473133
0.9456	High Similarity	NPC104406
0.9456	High Similarity	NPC47388
0.9456	High Similarity	NPC24673
0.9456	High Similarity	NPC201731
0.9456	High Similarity	NPC97716
0.9456	High Similarity	NPC283234
0.9456	High Similarity	NPC91902
0.9452	High Similarity	NPC209040
0.9452	High Similarity	NPC224714
0.9452	High Similarity	NPC124780
0.9452	High Similarity	NPC87486
0.9452	High Similarity	NPC470890
0.9416	High Similarity	NPC474033
0.9416	High Similarity	NPC474034
0.9412	High Similarity	NPC192686
0.9412	High Similarity	NPC119209
0.9412	High Similarity	NPC118256
0.9408	High Similarity	NPC284820
0.9408	High Similarity	NPC473272
0.94	High Similarity	NPC210597
0.9396	High Similarity	NPC180351
0.9396	High Similarity	NPC471115
0.9396	High Similarity	NPC29777
0.9392	High Similarity	NPC266572
0.9392	High Similarity	NPC161191
0.9392	High Similarity	NPC296869
0.9392	High Similarity	NPC168085
0.9384	High Similarity	NPC91560
0.9384	High Similarity	NPC221432
0.9384	High Similarity	NPC214166
0.9384	High Similarity	NPC38219
0.9384	High Similarity	NPC75049
0.9384	High Similarity	NPC18585
0.9384	High Similarity	NPC117836
0.9384	High Similarity	NPC51887
0.9384	High Similarity	NPC143896
0.9384	High Similarity	NPC164980
0.9384	High Similarity	NPC149026
0.9384	High Similarity	NPC169591
0.9384	High Similarity	NPC316816
0.9384	High Similarity	NPC257097
0.9384	High Similarity	NPC219915
0.9384	High Similarity	NPC175504
0.9384	High Similarity	NPC310130
0.9384	High Similarity	NPC106985
0.9384	High Similarity	NPC68104
0.9384	High Similarity	NPC166138
0.9384	High Similarity	NPC475705
0.9384	High Similarity	NPC39329
0.9384	High Similarity	NPC478086
0.9384	High Similarity	NPC476178
0.9384	High Similarity	NPC150408
0.9355	High Similarity	NPC472625
0.9355	High Similarity	NPC183672
0.9351	High Similarity	NPC472632
0.9351	High Similarity	NPC97812
0.9351	High Similarity	NPC26326
0.9346	High Similarity	NPC117418
0.9346	High Similarity	NPC73511
0.9346	High Similarity	NPC473990
0.9346	High Similarity	NPC53545
0.9342	High Similarity	NPC471787
0.9338	High Similarity	NPC203080
0.9338	High Similarity	NPC100134
0.9338	High Similarity	NPC209760
0.9333	High Similarity	NPC471229
0.9329	High Similarity	NPC473016
0.9329	High Similarity	NPC317492
0.9324	High Similarity	NPC44721
0.9324	High Similarity	NPC211466
0.9324	High Similarity	NPC14875
0.9324	High Similarity	NPC202494
0.9324	High Similarity	NPC176869
0.9324	High Similarity	NPC122828
0.9324	High Similarity	NPC40086
0.9324	High Similarity	NPC3779
0.9324	High Similarity	NPC476182

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 NPC472583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	895
0.2-0.3	1676
0.3-0.4	2619
0.4-0.5	1935
0.5-0.6	1073
0.6-0.7	378
0.7-0.8	138
0.8-0.85	37
0.85-0.9	22
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.966	High Similarity	NPD4380	Phase 2
0.9281	High Similarity	NPD4381	Clinical (unspecified phase)
0.9211	High Similarity	NPD2393	Clinical (unspecified phase)
0.9189	High Similarity	NPD4378	Clinical (unspecified phase)
0.9156	High Similarity	NPD7075	Discontinued
0.9085	High Similarity	NPD7096	Clinical (unspecified phase)
0.906	High Similarity	NPD7410	Clinical (unspecified phase)
0.9041	High Similarity	NPD1549	Phase 2
0.902	High Similarity	NPD1934	Approved
0.902	High Similarity	NPD6801	Discontinued
0.9	High Similarity	NPD7804	Clinical (unspecified phase)
0.8973	High Similarity	NPD1552	Clinical (unspecified phase)
0.8973	High Similarity	NPD1550	Clinical (unspecified phase)
0.8904	High Similarity	NPD2796	Approved
0.8903	High Similarity	NPD8443	Clinical (unspecified phase)
0.8836	High Similarity	NPD1510	Phase 2
0.8831	High Similarity	NPD7411	Suspended
0.8812	High Similarity	NPD6168	Clinical (unspecified phase)
0.8812	High Similarity	NPD6167	Clinical (unspecified phase)
0.8812	High Similarity	NPD6166	Phase 2
0.8718	High Similarity	NPD2801	Approved
0.865	High Similarity	NPD7054	Approved
0.8618	High Similarity	NPD1511	Approved
0.8618	High Similarity	NPD6799	Approved
0.8599	High Similarity	NPD7819	Suspended
0.8598	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD7074	Phase 3
0.8589	High Similarity	NPD3818	Discontinued
0.8571	High Similarity	NPD5403	Approved
0.8562	High Similarity	NPD5494	Approved
0.8562	High Similarity	NPD1240	Approved
0.8545	High Similarity	NPD6797	Phase 2
0.8509	High Similarity	NPD6959	Discontinued
0.8506	High Similarity	NPD1512	Approved
0.8494	Intermediate Similarity	NPD6559	Discontinued
0.8494	Intermediate Similarity	NPD7251	Discontinued
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8491	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1607	Approved
0.8443	Intermediate Similarity	NPD7808	Phase 3
0.8442	Intermediate Similarity	NPD5401	Approved
0.8428	Intermediate Similarity	NPD3817	Phase 2
0.8428	Intermediate Similarity	NPD5402	Approved
0.8408	Intermediate Similarity	NPD6599	Discontinued
0.8375	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8301	Intermediate Similarity	NPD3750	Approved
0.8235	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD3749	Approved
0.8182	Intermediate Similarity	NPD4628	Phase 3
0.8117	Intermediate Similarity	NPD2800	Approved
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD920	Approved
0.8039	Intermediate Similarity	NPD1551	Phase 2
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8012	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD1243	Approved
0.7978	Intermediate Similarity	NPD7584	Approved
0.7978	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD3748	Approved
0.7966	Intermediate Similarity	NPD4360	Phase 2
0.7966	Intermediate Similarity	NPD4363	Phase 3
0.7962	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2313	Discontinued
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5124	Phase 1
0.7895	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5953	Discontinued
0.7882	Intermediate Similarity	NPD7286	Phase 2
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD7033	Discontinued
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7844	Intermediate Similarity	NPD1247	Approved
0.7843	Intermediate Similarity	NPD6651	Approved
0.7831	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3751	Discontinued
0.7808	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1465	Phase 2
0.78	Intermediate Similarity	NPD4908	Phase 1
0.7759	Intermediate Similarity	NPD8312	Approved
0.7759	Intermediate Similarity	NPD8313	Approved
0.7756	Intermediate Similarity	NPD2344	Approved
0.7712	Intermediate Similarity	NPD943	Approved
0.7707	Intermediate Similarity	NPD2424	Discontinued
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.7669	Intermediate Similarity	NPD3226	Approved
0.765	Intermediate Similarity	NPD6782	Approved
0.765	Intermediate Similarity	NPD6777	Approved
0.765	Intermediate Similarity	NPD6781	Approved
0.765	Intermediate Similarity	NPD6776	Approved
0.765	Intermediate Similarity	NPD6778	Approved
0.765	Intermediate Similarity	NPD6779	Approved
0.765	Intermediate Similarity	NPD6780	Approved
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.7628	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1203	Approved
0.759	Intermediate Similarity	NPD8455	Phase 2
0.7586	Intermediate Similarity	NPD3823	Discontinued
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.7576	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7566	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6832	Phase 2
0.7562	Intermediate Similarity	NPD2309	Approved
0.7561	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7458	Discontinued
0.7553	Intermediate Similarity	NPD7585	Approved
0.755	Intermediate Similarity	NPD2798	Approved
0.7547	Intermediate Similarity	NPD1652	Phase 2
0.7544	Intermediate Similarity	NPD3926	Phase 2
0.7534	Intermediate Similarity	NPD1548	Phase 1
0.7531	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6844	Discontinued
0.7528	Intermediate Similarity	NPD8150	Discontinued
0.7528	Intermediate Similarity	NPD8434	Phase 2
0.7527	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4361	Phase 2
0.7527	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7583	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD6798	Discontinued
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD230	Phase 1
0.7436	Intermediate Similarity	NPD1933	Approved
0.7433	Intermediate Similarity	NPD7697	Approved
0.7433	Intermediate Similarity	NPD7698	Approved
0.7433	Intermediate Similarity	NPD7696	Phase 3
0.7423	Intermediate Similarity	NPD4662	Approved
0.7423	Intermediate Similarity	NPD4661	Approved
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7403	Intermediate Similarity	NPD4625	Phase 3
0.74	Intermediate Similarity	NPD9717	Approved
0.7399	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7871	Phase 2
0.7394	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD1653	Approved
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.738	Intermediate Similarity	NPD6823	Phase 2
0.7377	Intermediate Similarity	NPD6534	Approved
0.7377	Intermediate Similarity	NPD6535	Approved
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7701	Phase 2
0.7368	Intermediate Similarity	NPD2797	Approved
0.7365	Intermediate Similarity	NPD5889	Approved
0.7365	Intermediate Similarity	NPD5890	Approved
0.7346	Intermediate Similarity	NPD6190	Approved
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7344	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7783	Phase 2
0.7337	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD422	Phase 1
0.733	Intermediate Similarity	NPD1729	Discontinued
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.7325	Intermediate Similarity	NPD6355	Discontinued
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD447	Suspended
0.7308	Intermediate Similarity	NPD6233	Phase 2
0.7305	Intermediate Similarity	NPD6585	Discontinued
0.7303	Intermediate Similarity	NPD3225	Approved
0.7292	Intermediate Similarity	NPD7874	Approved
0.7292	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5761	Phase 2
0.7278	Intermediate Similarity	NPD5760	Phase 2
0.7273	Intermediate Similarity	NPD5049	Phase 3
0.7261	Intermediate Similarity	NPD4307	Phase 2
0.7258	Intermediate Similarity	NPD7699	Phase 2
0.7258	Intermediate Similarity	NPD7700	Phase 2
0.7254	Intermediate Similarity	NPD7801	Approved
0.7253	Intermediate Similarity	NPD4287	Approved
0.7244	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2354	Approved
0.7239	Intermediate Similarity	NPD3887	Approved
0.7238	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4536	Approved
0.7233	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4538	Approved
0.7222	Intermediate Similarity	NPD2654	Approved
0.7222	Intermediate Similarity	NPD5698	Clinical (unspecified phase)

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