NPASS Compound

Structure

NPC472584 OpenBabel07101718292D 27 31 0 0 1 0 0 0 0 0999 V2000 6.8390 3.3284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8444 3.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 3.0898 1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 0.5181 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 4.6722 2.1361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6232 1.8271 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 6.4322 2.4149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3631 3.0872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3458 2.0081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6232 0.8271 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 4 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 21 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 27 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 6 0 0 0 17 25 1 0 0 0 0 18 20 1 1 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.09
Volume:	352.134
LogP:	2.895
LogD:	2.654
LogS:	-4.493
# Rotatable Bonds:	1
TPSA:	113.27
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	3.78
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:	-5.044
MDCK Permeability:	4.480447751120664e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	81.2653579711914%
Volume Distribution (VD):	0.964
Pgp-substrate:	14.312371253967285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.558
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.574
CYP2D6-substrate:	0.307
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	4.351
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.883
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.319
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.199
Carcinogencity:	0.211
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC472584

Natural Product ID:	NPC472584
*Common Name:**	ZJBOZZWXWWQLRJ-WMZOPIPTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZJBOZZWXWWQLRJ-WMZOPIPTSA-N
Standard InCHI:	InChI=1S/C20H16O7/c1-20(2,24)18-16(22)11-6-10-13(7-14(11)26-18)25-17-9-4-3-8(21)5-12(9)27-19(23)15(10)17/h3-7,16,18,21-22,24H,1-2H3/t16-,18-/m0/s1
SMILES:	Oc1ccc2c(c1)oc(=O)c1c2oc2c1cc1c(c2)O[C@@H]([C@H]1O)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577249
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000354] Coumestans

*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	3

Activity Type	# Activity
Cell Line	2
Others	1

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[479211]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[479211]
NPT2	Others	Unspecified		IC50	=	119000.0	nM	PMID[479211]

☑ 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 NPC472584 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	374
0.1-0.2	1603
0.2-0.3	3553
0.3-0.4	8330
0.4-0.5	10322
0.5-0.6	4330
0.6-0.7	5670
0.7-0.8	4578
0.8-0.85	3068
0.85-0.9	755
0.9-0.95	111
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC120220
0.9448	High Similarity	NPC320789
0.9448	High Similarity	NPC476459
0.9437	High Similarity	NPC260296
0.9437	High Similarity	NPC115432
0.9383	High Similarity	NPC155640
0.9375	High Similarity	NPC244750
0.9259	High Similarity	NPC45124
0.9259	High Similarity	NPC74854
0.9259	High Similarity	NPC30655
0.9255	High Similarity	NPC40583
0.9207	High Similarity	NPC259007
0.9207	High Similarity	NPC204088
0.9207	High Similarity	NPC329215
0.9198	High Similarity	NPC304839
0.9198	High Similarity	NPC220582
0.9157	High Similarity	NPC53252
0.9152	High Similarity	NPC53640
0.9152	High Similarity	NPC323137
0.9146	High Similarity	NPC472581
0.9141	High Similarity	NPC14822
0.9141	High Similarity	NPC92589
0.9136	High Similarity	NPC476350
0.9136	High Similarity	NPC476349
0.9125	High Similarity	NPC1477
0.9125	High Similarity	NPC213608
0.9107	High Similarity	NPC261471
0.908	High Similarity	NPC239270
0.908	High Similarity	NPC95472
0.908	High Similarity	NPC49009
0.908	High Similarity	NPC303210
0.908	High Similarity	NPC169
0.9074	High Similarity	NPC260902
0.9074	High Similarity	NPC296957
0.9074	High Similarity	NPC65504
0.9068	High Similarity	NPC108937
0.9068	High Similarity	NPC279218
0.9062	High Similarity	NPC5871
0.9062	High Similarity	NPC41326
0.9062	High Similarity	NPC473996
0.9012	High Similarity	NPC475797
0.9012	High Similarity	NPC474609
0.9012	High Similarity	NPC129053
0.9012	High Similarity	NPC247677
0.9012	High Similarity	NPC474738
0.9012	High Similarity	NPC78554
0.9012	High Similarity	NPC469936
0.9012	High Similarity	NPC321372
0.9012	High Similarity	NPC160015
0.9012	High Similarity	NPC109967
0.9	High Similarity	NPC471676
0.9	High Similarity	NPC472423
0.9	High Similarity	NPC164384
0.9	High Similarity	NPC472580
0.9	High Similarity	NPC474744
0.9	High Similarity	NPC312630
0.9	High Similarity	NPC472636
0.9	High Similarity	NPC472422
0.9	High Similarity	NPC244577
0.9	High Similarity	NPC474772
0.9	High Similarity	NPC263384
0.9	High Similarity	NPC324220
0.9	High Similarity	NPC472420
0.8994	High Similarity	NPC37606
0.8988	High Similarity	NPC218533
0.8988	High Similarity	NPC78830
0.897	High Similarity	NPC219861
0.8957	High Similarity	NPC269495
0.8944	High Similarity	NPC477957
0.8944	High Similarity	NPC31627
0.8944	High Similarity	NPC285623
0.8944	High Similarity	NPC476238
0.8944	High Similarity	NPC327269
0.8944	High Similarity	NPC256141
0.8938	High Similarity	NPC472421
0.8922	High Similarity	NPC119589
0.8916	High Similarity	NPC471286
0.8916	High Similarity	NPC91288
0.8916	High Similarity	NPC109180
0.8916	High Similarity	NPC38591
0.8909	High Similarity	NPC97812
0.8896	High Similarity	NPC470625
0.8896	High Similarity	NPC13879
0.8896	High Similarity	NPC471787
0.8889	High Similarity	NPC472583
0.8889	High Similarity	NPC122365
0.8889	High Similarity	NPC7989
0.8889	High Similarity	NPC469405
0.8889	High Similarity	NPC223701
0.8882	High Similarity	NPC471677
0.8882	High Similarity	NPC471675
0.8875	High Similarity	NPC296030
0.8875	High Similarity	NPC226644
0.8875	High Similarity	NPC37226
0.8875	High Similarity	NPC39929
0.8869	High Similarity	NPC86477
0.8862	High Similarity	NPC136641
0.8862	High Similarity	NPC300053
0.8844	High Similarity	NPC97523
0.8834	High Similarity	NPC474542
0.8834	High Similarity	NPC477958
0.8834	High Similarity	NPC469934
0.8827	High Similarity	NPC171651
0.8827	High Similarity	NPC475790
0.8827	High Similarity	NPC67654
0.8827	High Similarity	NPC35567
0.8827	High Similarity	NPC243171
0.8827	High Similarity	NPC210597
0.882	High Similarity	NPC180351
0.8812	High Similarity	NPC135325
0.881	High Similarity	NPC277480
0.8802	High Similarity	NPC124038
0.878	High Similarity	NPC208152
0.878	High Similarity	NPC78492
0.8779	High Similarity	NPC325176
0.8773	High Similarity	NPC293286
0.8773	High Similarity	NPC209760
0.8773	High Similarity	NPC472462
0.8773	High Similarity	NPC100134
0.8772	High Similarity	NPC310794
0.8765	High Similarity	NPC254412
0.8765	High Similarity	NPC290671
0.8765	High Similarity	NPC474021
0.8765	High Similarity	NPC131866
0.8765	High Similarity	NPC262038
0.8765	High Similarity	NPC262039
0.8765	High Similarity	NPC278476
0.8765	High Similarity	NPC156244
0.8765	High Similarity	NPC474023
0.8765	High Similarity	NPC170169
0.8765	High Similarity	NPC471229
0.8765	High Similarity	NPC319910
0.8758	High Similarity	NPC221868
0.8758	High Similarity	NPC472628
0.8758	High Similarity	NPC37208
0.8758	High Similarity	NPC89442
0.8758	High Similarity	NPC317492
0.8757	High Similarity	NPC247973
0.875	High Similarity	NPC14875
0.875	High Similarity	NPC130581
0.875	High Similarity	NPC472627
0.875	High Similarity	NPC37183
0.875	High Similarity	NPC12148
0.8743	High Similarity	NPC93215
0.8735	High Similarity	NPC471976
0.8735	High Similarity	NPC306978
0.8727	High Similarity	NPC268360
0.8727	High Similarity	NPC270044
0.872	High Similarity	NPC48579
0.872	High Similarity	NPC198490
0.872	High Similarity	NPC217706
0.872	High Similarity	NPC476169
0.872	High Similarity	NPC148938
0.872	High Similarity	NPC470681
0.872	High Similarity	NPC207809
0.872	High Similarity	NPC259710
0.872	High Similarity	NPC477530
0.872	High Similarity	NPC471116
0.872	High Similarity	NPC304207
0.8712	High Similarity	NPC150123
0.8712	High Similarity	NPC10807
0.8712	High Similarity	NPC216035
0.8712	High Similarity	NPC244583
0.8712	High Similarity	NPC161881
0.8712	High Similarity	NPC138288
0.8712	High Similarity	NPC56232
0.8712	High Similarity	NPC217149
0.8704	High Similarity	NPC267117
0.8704	High Similarity	NPC470908
0.8704	High Similarity	NPC474735
0.8704	High Similarity	NPC78335
0.8704	High Similarity	NPC105136
0.8704	High Similarity	NPC230713
0.8698	High Similarity	NPC82330
0.8696	High Similarity	NPC168085
0.8696	High Similarity	NPC39195
0.8696	High Similarity	NPC272194
0.8688	High Similarity	NPC210826
0.8688	High Similarity	NPC51641
0.8688	High Similarity	NPC316769
0.8688	High Similarity	NPC300267
0.8688	High Similarity	NPC472629
0.8683	High Similarity	NPC472346
0.8683	High Similarity	NPC3629
0.8675	High Similarity	NPC50430
0.8667	High Similarity	NPC215917
0.8667	High Similarity	NPC10754
0.8667	High Similarity	NPC20530
0.8659	High Similarity	NPC20907
0.8659	High Similarity	NPC183874
0.8659	High Similarity	NPC203080
0.8659	High Similarity	NPC244250
0.8659	High Similarity	NPC248793
0.8659	High Similarity	NPC180301
0.8659	High Similarity	NPC235333
0.865	High Similarity	NPC209846
0.865	High Similarity	NPC317715
0.865	High Similarity	NPC289774
0.865	High Similarity	NPC312549
0.865	High Similarity	NPC78835

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 NPC472584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	884
0.2-0.3	1749
0.3-0.4	2612
0.4-0.5	2025
0.5-0.6	1023
0.6-0.7	331
0.7-0.8	128
0.8-0.85	46
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD3749	Approved
0.8727	High Similarity	NPD7075	Discontinued
0.8663	High Similarity	NPD6559	Discontinued
0.8659	High Similarity	NPD7096	Clinical (unspecified phase)
0.8589	High Similarity	NPD4380	Phase 2
0.8485	Intermediate Similarity	NPD6801	Discontinued
0.8434	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7411	Suspended
0.8405	Intermediate Similarity	NPD920	Approved
0.8393	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD5844	Phase 1
0.8274	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD1934	Approved
0.825	Intermediate Similarity	NPD1549	Phase 2
0.8225	Intermediate Similarity	NPD7768	Phase 2
0.8225	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6799	Approved
0.8218	Intermediate Similarity	NPD3818	Discontinued
0.8199	Intermediate Similarity	NPD1243	Approved
0.8198	Intermediate Similarity	NPD6232	Discontinued
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5494	Approved
0.8187	Intermediate Similarity	NPD2344	Approved
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7473	Discontinued
0.816	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6599	Discontinued
0.8118	Intermediate Similarity	NPD3882	Suspended
0.8103	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD6166	Phase 2
0.8103	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD6959	Discontinued
0.8023	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD2801	Approved
0.7988	Intermediate Similarity	NPD2309	Approved
0.7975	Intermediate Similarity	NPD2800	Approved
0.7975	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5403	Approved
0.7953	Intermediate Similarity	NPD3817	Phase 2
0.7953	Intermediate Similarity	NPD5402	Approved
0.7952	Intermediate Similarity	NPD2532	Approved
0.7952	Intermediate Similarity	NPD2533	Approved
0.7952	Intermediate Similarity	NPD2534	Approved
0.795	Intermediate Similarity	NPD1510	Phase 2
0.7943	Intermediate Similarity	NPD3926	Phase 2
0.7927	Intermediate Similarity	NPD4628	Phase 3
0.7921	Intermediate Similarity	NPD7074	Phase 3
0.7912	Intermediate Similarity	NPD8434	Phase 2
0.7889	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7054	Approved
0.7853	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5401	Approved
0.7838	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7472	Approved
0.7818	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD1240	Approved
0.7809	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7784	Intermediate Similarity	NPD1511	Approved
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD5953	Discontinued
0.7765	Intermediate Similarity	NPD3226	Approved
0.7735	Intermediate Similarity	NPD7251	Discontinued
0.773	Intermediate Similarity	NPD4287	Approved
0.773	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD1247	Approved
0.7716	Intermediate Similarity	NPD1607	Approved
0.7711	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7808	Phase 3
0.7692	Intermediate Similarity	NPD1512	Approved
0.7683	Intermediate Similarity	NPD2935	Discontinued
0.7683	Intermediate Similarity	NPD1551	Phase 2
0.7667	Intermediate Similarity	NPD7286	Phase 2
0.765	Intermediate Similarity	NPD8313	Approved
0.765	Intermediate Similarity	NPD8312	Approved
0.7611	Intermediate Similarity	NPD3751	Discontinued
0.7596	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6808	Phase 2
0.7579	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2313	Discontinued
0.754	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2346	Discontinued
0.7529	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7199	Phase 2
0.7515	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD7033	Discontinued
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.7486	Intermediate Similarity	NPD7229	Phase 3
0.7486	Intermediate Similarity	NPD5711	Approved
0.7486	Intermediate Similarity	NPD5710	Approved
0.7486	Intermediate Similarity	NPD8455	Phase 2
0.7473	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD2296	Approved
0.7442	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5124	Phase 1
0.7439	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7783	Phase 2
0.7436	Intermediate Similarity	NPD7435	Discontinued
0.7418	Intermediate Similarity	NPD7228	Approved
0.7416	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3787	Discontinued
0.7386	Intermediate Similarity	NPD5761	Phase 2
0.7386	Intermediate Similarity	NPD5760	Phase 2
0.7375	Intermediate Similarity	NPD1203	Approved
0.7371	Intermediate Similarity	NPD6778	Approved
0.7371	Intermediate Similarity	NPD6779	Approved
0.7371	Intermediate Similarity	NPD6782	Approved
0.7371	Intermediate Similarity	NPD6777	Approved
0.7371	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6780	Approved
0.7371	Intermediate Similarity	NPD6776	Approved
0.7371	Intermediate Similarity	NPD6781	Approved
0.7362	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3764	Approved
0.7348	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6832	Phase 2
0.734	Intermediate Similarity	NPD8150	Discontinued
0.733	Intermediate Similarity	NPD6280	Approved
0.733	Intermediate Similarity	NPD6279	Approved
0.733	Intermediate Similarity	NPD37	Approved
0.7323	Intermediate Similarity	NPD7584	Approved
0.7305	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4360	Phase 2
0.7292	Intermediate Similarity	NPD4363	Phase 3
0.7289	Intermediate Similarity	NPD6651	Approved
0.7278	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7458	Discontinued
0.7256	Intermediate Similarity	NPD6798	Discontinued
0.7256	Intermediate Similarity	NPD3268	Approved
0.7239	Intermediate Similarity	NPD4908	Phase 1
0.7235	Intermediate Similarity	NPD1652	Phase 2
0.7229	Intermediate Similarity	NPD230	Phase 1
0.7229	Intermediate Similarity	NPD6355	Discontinued
0.7229	Intermediate Similarity	NPD447	Suspended
0.7222	Intermediate Similarity	NPD7870	Phase 2
0.7222	Intermediate Similarity	NPD7871	Phase 2
0.7219	Intermediate Similarity	NPD6005	Phase 3
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD6004	Phase 3
0.7219	Intermediate Similarity	NPD6002	Phase 3
0.7219	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7874	Approved
0.7214	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4308	Phase 3
0.72	Intermediate Similarity	NPD7585	Approved
0.7188	Intermediate Similarity	NPD9717	Approved
0.7172	Intermediate Similarity	NPD7697	Approved
0.7172	Intermediate Similarity	NPD7698	Approved
0.7172	Intermediate Similarity	NPD7696	Phase 3
0.7169	Intermediate Similarity	NPD943	Approved
0.7169	Intermediate Similarity	NPD1613	Approved
0.7169	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7390	Discontinued
0.7166	Intermediate Similarity	NPD7685	Pre-registration
0.7165	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4361	Phase 2
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.7151	Intermediate Similarity	NPD6190	Approved
0.715	Intermediate Similarity	NPD7583	Approved
0.7126	Intermediate Similarity	NPD1933	Approved
0.7126	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7701	Phase 2
0.7113	Intermediate Similarity	NPD6534	Approved
0.7113	Intermediate Similarity	NPD6535	Approved
0.7108	Intermediate Similarity	NPD6233	Phase 2
0.7107	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1653	Approved
0.7093	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD6273	Approved
0.7074	Intermediate Similarity	NPD6764	Approved
0.7074	Intermediate Similarity	NPD7240	Approved
0.7074	Intermediate Similarity	NPD6765	Approved
0.7073	Intermediate Similarity	NPD7930	Approved
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD1729	Discontinued
0.7059	Intermediate Similarity	NPD5408	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