NPASS Compound

Structure

NPC11561 OpenBabel07101719142D 25 27 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 1.7321 -1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 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 1.7321 2.0000 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 2.5981 0.5000 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 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.14
Volume:	357.536
LogP:	4.683
LogD:	3.94
LogS:	-5.102
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	2.639
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.82
MDCK Permeability:	1.3042626051174011e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	101.15632629394531%
Volume Distribution (VD):	0.502
Pgp-substrate:	0.6075172424316406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.646
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.206
CYP2C9-inhibitor:	0.907
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.889
CYP2D6-substrate:	0.704
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	3.119
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.773
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.605
Maximum Recommended Daily Dose:	0.452
Skin Sensitization:	0.601
Carcinogencity:	0.886
Eye Corrosion:	0.003
Eye Irritation:	0.661
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC11561

Natural Product ID:	NPC11561
*Common Name:**	Pongachalconel
IUPAC Name:	(E)-1-(5-hydroxy-7-methoxy-2,2-dimethylchromen-6-yl)-3-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	VLSXHSGQICXETC-MDZDMXLPSA-N
Standard InCHI:	InChI=1S/C21H20O4/c1-21(2)12-11-15-17(25-21)13-18(24-3)19(20(15)23)16(22)10-9-14-7-5-4-6-8-14/h4-13,23H,1-3H3/b10-9+
SMILES:	COc1cc2OC(C)(C)C=Cc2c(c1C(=O)/C=C/c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3401055
PubChem CID:	11056805
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25630222]
NPO19856	Millettia pulchra	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
Others	3

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	2.14	n.a.	PMID[487798]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	83.0	%	PMID[487798]
NPT35	Others	n.a.		Retention_time	=	131.0	min	PMID[487798]

☑ 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 NPC11561 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	1558
0.2-0.3	4003
0.3-0.4	10428
0.4-0.5	7794
0.5-0.6	3585
0.6-0.7	5713
0.7-0.8	5143
0.8-0.85	2050
0.85-0.9	1248
0.9-0.95	598
0.95-1	203

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC226636
0.9926	High Similarity	NPC156590
0.9926	High Similarity	NPC103362
0.9926	High Similarity	NPC64908
0.9926	High Similarity	NPC118840
0.9926	High Similarity	NPC110969
0.9926	High Similarity	NPC205006
0.9926	High Similarity	NPC147688
0.9855	High Similarity	NPC311741
0.9855	High Similarity	NPC234629
0.9853	High Similarity	NPC475680
0.9853	High Similarity	NPC159275
0.9853	High Similarity	NPC305355
0.9853	High Similarity	NPC172986
0.9853	High Similarity	NPC261227
0.9853	High Similarity	NPC241100
0.9853	High Similarity	NPC150522
0.9853	High Similarity	NPC235239
0.9853	High Similarity	NPC270883
0.9783	High Similarity	NPC106985
0.9783	High Similarity	NPC166138
0.9783	High Similarity	NPC38219
0.9783	High Similarity	NPC18585
0.9781	High Similarity	NPC282300
0.9779	High Similarity	NPC78913
0.9779	High Similarity	NPC217186
0.9779	High Similarity	NPC220062
0.9779	High Similarity	NPC96565
0.9779	High Similarity	NPC301217
0.9779	High Similarity	NPC303633
0.9779	High Similarity	NPC216978
0.9779	High Similarity	NPC18260
0.9779	High Similarity	NPC55018
0.9779	High Similarity	NPC53181
0.9714	High Similarity	NPC97716
0.9714	High Similarity	NPC23728
0.9714	High Similarity	NPC237635
0.9714	High Similarity	NPC104406
0.9714	High Similarity	NPC110303
0.9714	High Similarity	NPC24673
0.9714	High Similarity	NPC201731
0.9714	High Similarity	NPC79469
0.9712	High Similarity	NPC469953
0.9712	High Similarity	NPC209040
0.971	High Similarity	NPC214236
0.971	High Similarity	NPC144499
0.971	High Similarity	NPC59739
0.971	High Similarity	NPC62840
0.971	High Similarity	NPC293852
0.971	High Similarity	NPC217083
0.971	High Similarity	NPC78803
0.971	High Similarity	NPC299080
0.9708	High Similarity	NPC69769
0.9706	High Similarity	NPC201395
0.9645	High Similarity	NPC132592
0.9645	High Similarity	NPC266572
0.9645	High Similarity	NPC160821
0.9645	High Similarity	NPC6511
0.9643	High Similarity	NPC176229
0.9643	High Similarity	NPC475052
0.9643	High Similarity	NPC312973
0.9643	High Similarity	NPC88964
0.9643	High Similarity	NPC470647
0.9643	High Similarity	NPC54577
0.9643	High Similarity	NPC246948
0.9643	High Similarity	NPC111786
0.9643	High Similarity	NPC477955
0.9643	High Similarity	NPC142405
0.9643	High Similarity	NPC195621
0.9643	High Similarity	NPC267375
0.9643	High Similarity	NPC301276
0.9643	High Similarity	NPC124729
0.9643	High Similarity	NPC20488
0.9643	High Similarity	NPC67805
0.9643	High Similarity	NPC83357
0.9643	High Similarity	NPC214774
0.964	High Similarity	NPC221432
0.964	High Similarity	NPC143896
0.964	High Similarity	NPC175504
0.964	High Similarity	NPC219915
0.964	High Similarity	NPC310130
0.964	High Similarity	NPC75049
0.964	High Similarity	NPC316816
0.964	High Similarity	NPC39329
0.964	High Similarity	NPC257097
0.964	High Similarity	NPC91560
0.964	High Similarity	NPC214166
0.964	High Similarity	NPC68104
0.964	High Similarity	NPC150408
0.964	High Similarity	NPC478086
0.964	High Similarity	NPC169591
0.964	High Similarity	NPC164980
0.964	High Similarity	NPC149026
0.9638	High Similarity	NPC3188
0.9635	High Similarity	NPC23257
0.9632	High Similarity	NPC250266
0.9632	High Similarity	NPC266597
0.9632	High Similarity	NPC317119
0.9574	High Similarity	NPC473077
0.9574	High Similarity	NPC283234
0.9574	High Similarity	NPC296998
0.9571	High Similarity	NPC216538
0.9571	High Similarity	NPC257236
0.9571	High Similarity	NPC236766
0.9571	High Similarity	NPC273538
0.9571	High Similarity	NPC319752
0.9571	High Similarity	NPC473013
0.9571	High Similarity	NPC473015
0.9571	High Similarity	NPC131579
0.9571	High Similarity	NPC278175
0.9571	High Similarity	NPC131568
0.9571	High Similarity	NPC197252
0.9568	High Similarity	NPC148757
0.9568	High Similarity	NPC37496
0.9568	High Similarity	NPC125855
0.9568	High Similarity	NPC265040
0.9568	High Similarity	NPC296917
0.9568	High Similarity	NPC1089
0.9568	High Similarity	NPC194432
0.9568	High Similarity	NPC76338
0.9568	High Similarity	NPC306829
0.9568	High Similarity	NPC182852
0.9568	High Similarity	NPC166934
0.9568	High Similarity	NPC32739
0.9568	High Similarity	NPC177354
0.9568	High Similarity	NPC228504
0.9568	High Similarity	NPC107572
0.9568	High Similarity	NPC200694
0.9568	High Similarity	NPC166482
0.9568	High Similarity	NPC147145
0.9568	High Similarity	NPC223500
0.9568	High Similarity	NPC227579
0.9568	High Similarity	NPC64915
0.9568	High Similarity	NPC161506
0.9568	High Similarity	NPC328164
0.9568	High Similarity	NPC167624
0.9568	High Similarity	NPC78
0.9568	High Similarity	NPC324436
0.9568	High Similarity	NPC220998
0.9568	High Similarity	NPC66515
0.9568	High Similarity	NPC324134
0.9568	High Similarity	NPC10937
0.9568	High Similarity	NPC40833
0.9568	High Similarity	NPC76372
0.9565	High Similarity	NPC471587
0.9565	High Similarity	NPC259166
0.9565	High Similarity	NPC219917
0.9565	High Similarity	NPC213659
0.9565	High Similarity	NPC144118
0.9565	High Similarity	NPC204985
0.9565	High Similarity	NPC80962
0.9565	High Similarity	NPC48624
0.9565	High Similarity	NPC326109
0.9565	High Similarity	NPC215311
0.9565	High Similarity	NPC172250
0.9562	High Similarity	NPC470669
0.9562	High Similarity	NPC131130
0.9562	High Similarity	NPC248995
0.9562	High Similarity	NPC124269
0.9562	High Similarity	NPC470668
0.9562	High Similarity	NPC21350
0.9562	High Similarity	NPC254168
0.9562	High Similarity	NPC272844
0.9559	High Similarity	NPC98115
0.9559	High Similarity	NPC473887
0.9559	High Similarity	NPC1486
0.9559	High Similarity	NPC174999
0.9559	High Similarity	NPC186838
0.9559	High Similarity	NPC29353
0.9559	High Similarity	NPC194281
0.9559	High Similarity	NPC477242
0.9559	High Similarity	NPC127447
0.9559	High Similarity	NPC274109
0.9559	High Similarity	NPC477244
0.9559	High Similarity	NPC66349
0.9559	High Similarity	NPC124784
0.9559	High Similarity	NPC161196
0.9559	High Similarity	NPC477243
0.9559	High Similarity	NPC231772
0.9559	High Similarity	NPC249606
0.9559	High Similarity	NPC12165
0.9559	High Similarity	NPC150399
0.9559	High Similarity	NPC41461
0.9559	High Similarity	NPC25287
0.9559	High Similarity	NPC168105
0.9559	High Similarity	NPC13408
0.9559	High Similarity	NPC47815
0.9559	High Similarity	NPC234133
0.951	High Similarity	NPC61258
0.951	High Similarity	NPC188403
0.9507	High Similarity	NPC244407
0.9507	High Similarity	NPC296869
0.9507	High Similarity	NPC321623
0.9507	High Similarity	NPC189087
0.9507	High Similarity	NPC168085
0.9507	High Similarity	NPC161191
0.9504	High Similarity	NPC285630
0.9504	High Similarity	NPC5820
0.9504	High Similarity	NPC178343
0.9504	High Similarity	NPC476088

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 NPC11561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	951
0.2-0.3	1477
0.3-0.4	2572
0.4-0.5	1944
0.5-0.6	1190
0.6-0.7	454
0.7-0.8	159
0.8-0.85	43
0.85-0.9	16
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9571	High Similarity	NPD7410	Clinical (unspecified phase)
0.9571	High Similarity	NPD4378	Clinical (unspecified phase)
0.9281	High Similarity	NPD1549	Phase 2
0.9209	High Similarity	NPD1550	Clinical (unspecified phase)
0.9209	High Similarity	NPD1552	Clinical (unspecified phase)
0.9203	High Similarity	NPD1510	Phase 2
0.9191	High Similarity	NPD1240	Approved
0.9137	High Similarity	NPD2796	Approved
0.9058	High Similarity	NPD1607	Approved
0.9048	High Similarity	NPD7411	Suspended
0.898	High Similarity	NPD4380	Phase 2
0.8926	High Similarity	NPD2393	Clinical (unspecified phase)
0.8874	High Similarity	NPD7075	Discontinued
0.8867	High Similarity	NPD8443	Clinical (unspecified phase)
0.8859	High Similarity	NPD6801	Discontinued
0.88	High Similarity	NPD7819	Suspended
0.88	High Similarity	NPD7096	Clinical (unspecified phase)
0.8699	High Similarity	NPD6799	Approved
0.8699	High Similarity	NPD1511	Approved
0.8681	High Similarity	NPD7421	Clinical (unspecified phase)
0.8675	High Similarity	NPD2801	Approved
0.8627	High Similarity	NPD4381	Clinical (unspecified phase)
0.8621	High Similarity	NPD3750	Approved
0.8609	High Similarity	NPD1934	Approved
0.8581	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD7768	Phase 2
0.8535	High Similarity	NPD7852	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD6599	Discontinued
0.8442	Intermediate Similarity	NPD3882	Suspended
0.8425	Intermediate Similarity	NPD1243	Approved
0.8425	Intermediate Similarity	NPD2800	Approved
0.8392	Intermediate Similarity	NPD6651	Approved
0.8387	Intermediate Similarity	NPD3749	Approved
0.8375	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD2935	Discontinued
0.8345	Intermediate Similarity	NPD1551	Phase 2
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8278	Intermediate Similarity	NPD920	Approved
0.8278	Intermediate Similarity	NPD5403	Approved
0.8276	Intermediate Similarity	NPD2799	Discontinued
0.8276	Intermediate Similarity	NPD3748	Approved
0.8258	Intermediate Similarity	NPD3817	Phase 2
0.8255	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2313	Discontinued
0.8199	Intermediate Similarity	NPD3818	Discontinued
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5494	Approved
0.8163	Intermediate Similarity	NPD2344	Approved
0.816	Intermediate Similarity	NPD5953	Discontinued
0.8148	Intermediate Similarity	NPD7286	Phase 2
0.8146	Intermediate Similarity	NPD5401	Approved
0.8146	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1203	Approved
0.8121	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8037	Intermediate Similarity	NPD7054	Approved
0.8027	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD7033	Discontinued
0.8026	Intermediate Similarity	NPD2532	Approved
0.8026	Intermediate Similarity	NPD2534	Approved
0.8026	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD6559	Discontinued
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7988	Intermediate Similarity	NPD7472	Approved
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3268	Approved
0.7986	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD6100	Approved
0.7973	Intermediate Similarity	NPD6099	Approved
0.7972	Intermediate Similarity	NPD6832	Phase 2
0.7958	Intermediate Similarity	NPD2798	Approved
0.7956	Intermediate Similarity	NPD1548	Phase 1
0.7947	Intermediate Similarity	NPD2309	Approved
0.7939	Intermediate Similarity	NPD6797	Phase 2
0.7935	Intermediate Similarity	NPD3226	Approved
0.7929	Intermediate Similarity	NPD9717	Approved
0.7911	Intermediate Similarity	NPD5402	Approved
0.7905	Intermediate Similarity	NPD4308	Phase 3
0.7892	Intermediate Similarity	NPD7251	Discontinued
0.7887	Intermediate Similarity	NPD2797	Approved
0.7881	Intermediate Similarity	NPD4628	Phase 3
0.7881	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD943	Approved
0.7875	Intermediate Similarity	NPD919	Approved
0.7857	Intermediate Similarity	NPD422	Phase 1
0.7847	Intermediate Similarity	NPD4908	Phase 1
0.7844	Intermediate Similarity	NPD7808	Phase 3
0.7823	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD5124	Phase 1
0.7818	Intermediate Similarity	NPD5844	Phase 1
0.78	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD1247	Approved
0.7738	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1610	Phase 2
0.7727	Intermediate Similarity	NPD7390	Discontinued
0.7714	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4363	Phase 3
0.7701	Intermediate Similarity	NPD4360	Phase 2
0.7697	Intermediate Similarity	NPD2654	Approved
0.7692	Intermediate Similarity	NPD3225	Approved
0.7683	Intermediate Similarity	NPD3926	Phase 2
0.7676	Intermediate Similarity	NPD3972	Approved
0.7671	Intermediate Similarity	NPD4625	Phase 3
0.7665	Intermediate Similarity	NPD1729	Discontinued
0.7657	Intermediate Similarity	NPD4361	Phase 2
0.7657	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3267	Approved
0.7639	Intermediate Similarity	NPD3266	Approved
0.7635	Intermediate Similarity	NPD4307	Phase 2
0.761	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1933	Approved
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4288	Approved
0.7571	Intermediate Similarity	NPD9545	Approved
0.7554	Intermediate Similarity	NPD9493	Approved
0.7547	Intermediate Similarity	NPD6585	Discontinued
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD5889	Approved
0.75	Intermediate Similarity	NPD5890	Approved
0.75	Intermediate Similarity	NPD1296	Phase 2
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7467	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1241	Discontinued
0.7432	Intermediate Similarity	NPD7584	Approved
0.7431	Intermediate Similarity	NPD1608	Approved
0.7419	Intermediate Similarity	NPD7003	Approved
0.741	Intermediate Similarity	NPD5710	Approved
0.741	Intermediate Similarity	NPD5711	Approved
0.7405	Intermediate Similarity	NPD5049	Phase 3
0.7397	Intermediate Similarity	NPD1164	Approved
0.7397	Intermediate Similarity	NPD1470	Approved
0.7389	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5406	Approved
0.7386	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5405	Approved
0.7386	Intermediate Similarity	NPD5404	Approved
0.7386	Intermediate Similarity	NPD5408	Approved
0.7383	Intermediate Similarity	NPD411	Approved
0.7383	Intermediate Similarity	NPD6798	Discontinued
0.7379	Intermediate Similarity	NPD4749	Approved
0.7375	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2354	Approved
0.7371	Intermediate Similarity	NPD4287	Approved
0.7368	Intermediate Similarity	NPD6104	Discontinued
0.7365	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2296	Approved
0.7361	Intermediate Similarity	NPD1201	Approved
0.7351	Intermediate Similarity	NPD447	Suspended
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7347	Intermediate Similarity	NPD1019	Discontinued
0.7342	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1471	Phase 3
0.7338	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7297	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1613	Approved
0.7285	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3887	Approved
0.7239	Intermediate Similarity	NPD7577	Discontinued
0.7239	Intermediate Similarity	NPD6844	Discontinued
0.7235	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3751	Discontinued
0.7233	Intermediate Similarity	NPD4661	Approved
0.7233	Intermediate Similarity	NPD4662	Approved
0.7226	Intermediate Similarity	NPD2353	Approved
0.7226	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD17	Approved
0.7219	Intermediate Similarity	NPD2403	Approved
0.7211	Intermediate Similarity	NPD1876	Approved
0.7208	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5761	Phase 2
0.7195	Intermediate Similarity	NPD5760	Phase 2
0.7192	Intermediate Similarity	NPD1481	Phase 2
0.7184	Intermediate Similarity	NPD8313	Approved
0.7184	Intermediate Similarity	NPD8312	Approved
0.7179	Intermediate Similarity	NPD2424	Discontinued
0.7171	Intermediate Similarity	NPD3142	Approved
0.7171	Intermediate Similarity	NPD3140	Approved
0.717	Intermediate Similarity	NPD7212	Phase 2
0.717	Intermediate Similarity	NPD7213	Phase 3
0.7169	Intermediate Similarity	NPD6971	Discontinued
0.7161	Intermediate Similarity	NPD4477	Approved
0.7161	Intermediate Similarity	NPD4476	Approved
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7199	Phase 2

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