NPASS Compound

Structure

NPC50430 OpenBabel07101718192D 31 35 0 0 1 0 0 0 0 0999 V2000 2.2272 -1.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 5.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6065 1.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7405 0.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6065 2.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8744 1.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7405 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0084 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5443 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8963 -0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8744 2.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 4.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0084 2.5608 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4103 4.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5443 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4103 2.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2764 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2079 0.9781 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 3.8745 -1.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 5.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4103 5.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 -0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 2.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1988 1.8917 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 12 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 25 2 0 0 0 0 12 28 1 0 0 0 0 14 18 1 0 0 0 0 14 26 2 0 0 0 0 15 13 1 1 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 19 2 0 0 0 0 17 30 1 0 0 0 0 18 21 2 0 0 0 0 19 21 1 0 0 0 0 20 19 1 6 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 29 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 1 0 0 0 23 30 1 6 0 0 0 23 31 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.15
Volume:	421.318
LogP:	3.739
LogD:	3.083
LogS:	-5.506
# Rotatable Bonds:	4
TPSA:	80.29
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	4.076
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	3.916201239917427e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	76.4798355102539%
Volume Distribution (VD):	0.966
Pgp-substrate:	15.09130859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.596
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.842
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.525
CYP2D6-substrate:	0.409
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	2.573
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.764
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.23
Rat Oral Acute Toxicity:	0.77
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.117
Carcinogencity:	0.342
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC50430

Natural Product ID:	NPC50430
*Common Name:**	YRLRQNVYUYVRRD-RLTFZFDCSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Purpurin
Standard InCHIKey:	YRLRQNVYUYVRRD-RLTFZFDCSA-N
Standard InCHI:	InChI=1S/C24H24O7/c1-12(25)28-22-20-19-17(30-23(20)31-24(22,2)3)11-16(27-4)18-14(26)10-15(29-21(18)19)13-8-6-5-7-9-13/h5-9,11,15,20,22-23H,10H2,1-4H3/t15-,20+,22+,23-/m0/s1
SMILES:	COc1cc2O[C@@H]3[C@H](c2c2c1C(=O)C[C@H](O2)c1ccccc1)[C@H](C(O3)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516163
PubChem CID:	44559427
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

*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
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10814365]
NPO22730	Indigofera spicata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23895019]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26476665]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322358]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22730	Indigofera spicata	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	5

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	5.6	uM	PMID[487771]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50700.0	nM	PMID[487771]
NPT2	Others	Unspecified		Ratio	>	9.0	n.a.	PMID[487771]
NPT2	Others	Unspecified		Ratio	=	376.7	n.a.	PMID[487772]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	63900.0	nM	PMID[487772]
NPT2	Others	Unspecified		CD	>	10.0	uM	PMID[487773]
NPT2	Others	Unspecified		CD	=	0.2	uM	PMID[487772]

☑ 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 NPC50430 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	412
0.1-0.2	1509
0.2-0.3	3198
0.3-0.4	7656
0.4-0.5	10957
0.5-0.6	4649
0.6-0.7	5804
0.7-0.8	6893
0.8-0.85	1469
0.85-0.9	144
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9803	High Similarity	NPC43971
0.9803	High Similarity	NPC19554
0.9803	High Similarity	NPC74749
0.9487	High Similarity	NPC91288
0.9241	High Similarity	NPC471286
0.9226	High Similarity	NPC470625
0.9177	High Similarity	NPC93215
0.9177	High Similarity	NPC310603
0.9103	High Similarity	NPC476652
0.9103	High Similarity	NPC155063
0.9103	High Similarity	NPC211482
0.9085	High Similarity	NPC164299
0.9073	High Similarity	NPC294365
0.8994	High Similarity	NPC34376
0.8981	High Similarity	NPC17521
0.8947	High Similarity	NPC171656
0.8875	High Similarity	NPC92589
0.8868	High Similarity	NPC470607
0.8868	High Similarity	NPC43761
0.8861	High Similarity	NPC109967
0.8861	High Similarity	NPC78554
0.8861	High Similarity	NPC127406
0.8861	High Similarity	NPC469936
0.8861	High Similarity	NPC129053
0.8861	High Similarity	NPC321372
0.8861	High Similarity	NPC474609
0.8861	High Similarity	NPC475797
0.8861	High Similarity	NPC474738
0.8846	High Similarity	NPC470380
0.8846	High Similarity	NPC318424
0.8846	High Similarity	NPC472636
0.882	High Similarity	NPC125991
0.8805	High Similarity	NPC43638
0.8805	High Similarity	NPC23817
0.8805	High Similarity	NPC470606
0.8805	High Similarity	NPC258644
0.8797	High Similarity	NPC108937
0.8797	High Similarity	NPC279218
0.879	High Similarity	NPC473996
0.878	High Similarity	NPC473202
0.8765	High Similarity	NPC183672
0.875	High Similarity	NPC113055
0.875	High Similarity	NPC308265
0.8742	High Similarity	NPC265480
0.8742	High Similarity	NPC149368
0.8742	High Similarity	NPC11566
0.8742	High Similarity	NPC45165
0.8742	High Similarity	NPC301897
0.8734	High Similarity	NPC106625
0.8733	High Similarity	NPC259685
0.8727	High Similarity	NPC120220
0.8726	High Similarity	NPC290671
0.8726	High Similarity	NPC471675
0.8726	High Similarity	NPC472580
0.8726	High Similarity	NPC23253
0.872	High Similarity	NPC320789
0.8712	High Similarity	NPC72016
0.871	High Similarity	NPC282335
0.871	High Similarity	NPC218300
0.8706	High Similarity	NPC106700
0.8704	High Similarity	NPC131745
0.8704	High Similarity	NPC259834
0.8704	High Similarity	NPC44947
0.8704	High Similarity	NPC478199
0.8696	High Similarity	NPC271479
0.8696	High Similarity	NPC200708
0.8696	High Similarity	NPC472320
0.8688	High Similarity	NPC117478
0.8688	High Similarity	NPC122809
0.8688	High Similarity	NPC161650
0.8688	High Similarity	NPC310206
0.8684	High Similarity	NPC470856
0.8679	High Similarity	NPC469934
0.8679	High Similarity	NPC470605
0.8679	High Similarity	NPC470603
0.8679	High Similarity	NPC470604
0.8679	High Similarity	NPC99233
0.8675	High Similarity	NPC472584
0.8675	High Similarity	NPC475825
0.8675	High Similarity	NPC223375
0.8671	High Similarity	NPC327269
0.8671	High Similarity	NPC31627
0.8671	High Similarity	NPC476238
0.8671	High Similarity	NPC121001
0.8671	High Similarity	NPC477957
0.8671	High Similarity	NPC259182
0.8671	High Similarity	NPC68882
0.8667	High Similarity	NPC477165
0.8662	High Similarity	NPC180351
0.8662	High Similarity	NPC472421
0.8654	High Similarity	NPC476342
0.865	High Similarity	NPC66087
0.865	High Similarity	NPC124155
0.865	High Similarity	NPC179198
0.865	High Similarity	NPC257566
0.865	High Similarity	NPC278419
0.8642	High Similarity	NPC47923
0.8634	High Similarity	NPC264932
0.8634	High Similarity	NPC40583
0.8634	High Similarity	NPC311574
0.8634	High Similarity	NPC104677
0.8634	High Similarity	NPC73511
0.8631	High Similarity	NPC324220
0.8631	High Similarity	NPC312630
0.8631	High Similarity	NPC325176
0.8625	High Similarity	NPC206378
0.8618	High Similarity	NPC473209
0.8616	High Similarity	NPC87304
0.8616	High Similarity	NPC168805
0.8616	High Similarity	NPC268950
0.8616	High Similarity	NPC108706
0.8616	High Similarity	NPC121910
0.8616	High Similarity	NPC211158
0.8616	High Similarity	NPC78021
0.8614	High Similarity	NPC298778
0.8614	High Similarity	NPC477572
0.8614	High Similarity	NPC76047
0.8614	High Similarity	NPC477573
0.8614	High Similarity	NPC477571
0.8608	High Similarity	NPC474772
0.8608	High Similarity	NPC244577
0.8608	High Similarity	NPC471677
0.8608	High Similarity	NPC209142
0.8608	High Similarity	NPC263384
0.8608	High Similarity	NPC309512
0.8608	High Similarity	NPC472420
0.8608	High Similarity	NPC78835
0.8608	High Similarity	NPC474744
0.8608	High Similarity	NPC316960
0.8608	High Similarity	NPC472422
0.8608	High Similarity	NPC472423
0.8608	High Similarity	NPC295650
0.8608	High Similarity	NPC204561
0.8608	High Similarity	NPC471676
0.8608	High Similarity	NPC317715
0.8608	High Similarity	NPC312549
0.8608	High Similarity	NPC148945
0.8608	High Similarity	NPC190217
0.8606	High Similarity	NPC476459
0.8605	High Similarity	NPC294863
0.8605	High Similarity	NPC282636
0.86	High Similarity	NPC99854
0.8599	High Similarity	NPC104236
0.8599	High Similarity	NPC164205
0.8599	High Similarity	NPC473016
0.8598	High Similarity	NPC294722
0.8598	High Similarity	NPC475979
0.859	High Similarity	NPC471285
0.859	High Similarity	NPC243154
0.859	High Similarity	NPC308200
0.8589	High Similarity	NPC414831
0.8589	High Similarity	NPC190450
0.8589	High Similarity	NPC18284
0.8589	High Similarity	NPC150164
0.8589	High Similarity	NPC302741
0.8589	High Similarity	NPC273021
0.8581	High Similarity	NPC131568
0.8581	High Similarity	NPC271288
0.8581	High Similarity	NPC131579
0.8581	High Similarity	NPC87486
0.8581	High Similarity	NPC124780
0.858	High Similarity	NPC298093
0.858	High Similarity	NPC321478
0.858	High Similarity	NPC172687
0.858	High Similarity	NPC306978
0.8571	High Similarity	NPC156457
0.8571	High Similarity	NPC469601
0.8571	High Similarity	NPC313163
0.8571	High Similarity	NPC161749
0.8571	High Similarity	NPC210048
0.8571	High Similarity	NPC197896
0.8571	High Similarity	NPC6985
0.8571	High Similarity	NPC147145
0.8571	High Similarity	NPC474345
0.8571	High Similarity	NPC66804
0.8571	High Similarity	NPC258035
0.8562	High Similarity	NPC97052
0.8562	High Similarity	NPC169248
0.8562	High Similarity	NPC27408
0.8562	High Similarity	NPC95090
0.8562	High Similarity	NPC26195
0.8562	High Similarity	NPC39351
0.8562	High Similarity	NPC472409
0.8562	High Similarity	NPC72649
0.8553	High Similarity	NPC40033
0.8553	High Similarity	NPC210597
0.8553	High Similarity	NPC256141
0.8553	High Similarity	NPC475790
0.8553	High Similarity	NPC259767
0.8553	High Similarity	NPC217149
0.8553	High Similarity	NPC288534
0.8553	High Similarity	NPC285623
0.8553	High Similarity	NPC88484
0.8553	High Similarity	NPC216035
0.8545	High Similarity	NPC178851
0.8544	High Similarity	NPC474735
0.8544	High Similarity	NPC476185
0.8544	High Similarity	NPC29777
0.8544	High Similarity	NPC471115
0.8544	High Similarity	NPC106025

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 NPC50430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	847
0.2-0.3	1694
0.3-0.4	2621
0.4-0.5	2030
0.5-0.6	1058
0.6-0.7	372
0.7-0.8	155
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8616	High Similarity	NPD7096	Clinical (unspecified phase)
0.858	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD7075	Discontinued
0.8443	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD2796	Approved
0.8402	Intermediate Similarity	NPD6559	Discontinued
0.8385	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.828	Intermediate Similarity	NPD6799	Approved
0.8274	Intermediate Similarity	NPD3818	Discontinued
0.8272	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7411	Suspended
0.8239	Intermediate Similarity	NPD920	Approved
0.8228	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6599	Discontinued
0.8199	Intermediate Similarity	NPD4380	Phase 2
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8141	Intermediate Similarity	NPD1243	Approved
0.8129	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7054	Approved
0.8113	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD3817	Phase 2
0.8101	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD1934	Approved
0.8077	Intermediate Similarity	NPD1549	Phase 2
0.807	Intermediate Similarity	NPD7472	Approved
0.8035	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6797	Phase 2
0.7977	Intermediate Similarity	NPD7251	Discontinued
0.7964	Intermediate Similarity	NPD919	Approved
0.7941	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7808	Phase 3
0.7904	Intermediate Similarity	NPD3749	Approved
0.7888	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD3748	Approved
0.787	Intermediate Similarity	NPD7199	Phase 2
0.7844	Intermediate Similarity	NPD7768	Phase 2
0.7844	Intermediate Similarity	NPD4965	Approved
0.7844	Intermediate Similarity	NPD4966	Approved
0.7844	Intermediate Similarity	NPD4967	Phase 2
0.7806	Intermediate Similarity	NPD1933	Approved
0.7803	Intermediate Similarity	NPD5844	Phase 1
0.7799	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD5403	Approved
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5401	Approved
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7771	Intermediate Similarity	NPD2799	Discontinued
0.7771	Intermediate Similarity	NPD1510	Phase 2
0.7765	Intermediate Similarity	NPD6959	Discontinued
0.7751	Intermediate Similarity	NPD6234	Discontinued
0.7738	Intermediate Similarity	NPD3882	Suspended
0.7738	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6166	Phase 2
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD2801	Approved
0.7725	Intermediate Similarity	NPD8455	Phase 2
0.7719	Intermediate Similarity	NPD6232	Discontinued
0.7697	Intermediate Similarity	NPD7458	Discontinued
0.7688	Intermediate Similarity	NPD2800	Approved
0.7684	Intermediate Similarity	NPD8313	Approved
0.7684	Intermediate Similarity	NPD8312	Approved
0.7679	Intermediate Similarity	NPD5402	Approved
0.7665	Intermediate Similarity	NPD37	Approved
0.7661	Intermediate Similarity	NPD1247	Approved
0.7644	Intermediate Similarity	NPD7228	Approved
0.764	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD3750	Approved
0.7628	Intermediate Similarity	NPD1240	Approved
0.7625	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1511	Approved
0.7607	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6832	Phase 2
0.7572	Intermediate Similarity	NPD3926	Phase 2
0.7532	Intermediate Similarity	NPD1607	Approved
0.7531	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7240	Approved
0.7468	Intermediate Similarity	NPD2798	Approved
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7443	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7435	Intermediate Similarity	NPD7584	Approved
0.7429	Intermediate Similarity	NPD2403	Approved
0.7416	Intermediate Similarity	NPD5953	Discontinued
0.7414	Intermediate Similarity	NPD7229	Phase 3
0.7414	Intermediate Similarity	NPD3787	Discontinued
0.7407	Intermediate Similarity	NPD5006	Approved
0.7407	Intermediate Similarity	NPD5005	Approved
0.7403	Intermediate Similarity	NPD3266	Approved
0.7403	Intermediate Similarity	NPD3267	Approved
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7396	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD7435	Discontinued
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7358	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5124	Phase 1
0.7358	Intermediate Similarity	NPD6355	Discontinued
0.7349	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3751	Discontinued
0.7341	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5711	Approved
0.7314	Intermediate Similarity	NPD5710	Approved
0.7302	Intermediate Similarity	NPD6779	Approved
0.7302	Intermediate Similarity	NPD6782	Approved
0.7302	Intermediate Similarity	NPD6777	Approved
0.7302	Intermediate Similarity	NPD6776	Approved
0.7302	Intermediate Similarity	NPD6780	Approved
0.7302	Intermediate Similarity	NPD6778	Approved
0.7302	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD4420	Approved
0.7282	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7783	Phase 2
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7685	Pre-registration
0.7273	Intermediate Similarity	NPD3887	Approved
0.7268	Intermediate Similarity	NPD8151	Discontinued
0.7259	Intermediate Similarity	NPD7930	Approved
0.7256	Intermediate Similarity	NPD2654	Approved
0.7254	Intermediate Similarity	NPD7583	Approved
0.7239	Intermediate Similarity	NPD2344	Approved
0.7239	Intermediate Similarity	NPD6004	Phase 3
0.7239	Intermediate Similarity	NPD6005	Phase 3
0.7239	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6002	Phase 3
0.7237	Intermediate Similarity	NPD17	Approved
0.7232	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4360	Phase 2
0.7219	Intermediate Similarity	NPD4363	Phase 3
0.7216	Intermediate Similarity	NPD6808	Phase 2
0.7216	Intermediate Similarity	NPD7585	Approved
0.7209	Intermediate Similarity	NPD1465	Phase 2
0.7205	Intermediate Similarity	NPD6651	Approved
0.7193	Intermediate Similarity	NPD5889	Approved
0.7193	Intermediate Similarity	NPD5890	Approved
0.7189	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4307	Phase 2
0.7188	Intermediate Similarity	NPD7698	Approved
0.7188	Intermediate Similarity	NPD7696	Phase 3
0.7188	Intermediate Similarity	NPD7697	Approved
0.7179	Intermediate Similarity	NPD2797	Approved
0.7178	Intermediate Similarity	NPD6099	Approved
0.7178	Intermediate Similarity	NPD6100	Approved
0.7176	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6798	Discontinued
0.716	Intermediate Similarity	NPD7097	Phase 1
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7874	Approved
0.7135	Intermediate Similarity	NPD6585	Discontinued
0.7134	Intermediate Similarity	NPD1019	Discontinued
0.7118	Intermediate Similarity	NPD1653	Approved
0.7097	Intermediate Similarity	NPD1608	Approved
0.7091	Intermediate Similarity	NPD2424	Discontinued
0.709	Intermediate Similarity	NPD4361	Phase 2
0.709	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5242	Approved
0.7073	Intermediate Similarity	NPD2438	Suspended
0.707	Intermediate Similarity	NPD1203	Approved
0.7069	Intermediate Similarity	NPD5353	Approved
0.7066	Intermediate Similarity	NPD2309	Approved
0.7063	Intermediate Similarity	NPD1296	Phase 2
0.7062	Intermediate Similarity	NPD8320	Phase 1
0.7062	Intermediate Similarity	NPD8319	Approved
0.7048	Intermediate Similarity	NPD1652	Phase 2
0.7047	Intermediate Similarity	NPD6823	Phase 2
0.7041	Intermediate Similarity	NPD7701	Phase 2
0.7037	Intermediate Similarity	NPD6535	Approved
0.7037	Intermediate Similarity	NPD6534	Approved
0.7032	Intermediate Similarity	NPD1610	Phase 2
0.703	Intermediate Similarity	NPD2353	Approved
0.703	Intermediate Similarity	NPD1471	Phase 3
0.703	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5058	Phase 3

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