NPASS Compound

Structure

CID110969 OpenBabel06191715462D 25 27 0 0 0 0 0 0 0 0999 V2000 -5.1962 -3.0000 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 -3.4641 1.0000 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 -3.4641 -2.0000 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 2.5981 -0.5000 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 3.4641 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 0.8660 -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 -4.3301 -3.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 0.0000 -2.0000 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 0.8660 -0.5000 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 4.3301 1.5000 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 -3.4641 -0.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 13 2 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 20 2 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 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:	5.344
LogD:	3.427
LogS:	-4.284
# Rotatable Bonds:	4
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	2.415
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:	-4.714
MDCK Permeability:	1.4035418644198216e-05
Pgp-inhibitor:	0.406
Pgp-substrate:	0.472
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.769
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	93.40277862548828%
Volume Distribution (VD):	0.804
Pgp-substrate:	6.571397304534912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.576
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.667
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	7.498
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.645
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.142
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.807
Skin Sensitization:	0.672
Carcinogencity:	0.162
Eye Corrosion:	0.003
Eye Irritation:	0.737
Respiratory Toxicity:	0.43

Download Data

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

Natural Product: NPC110969

Natural Product ID:	NPC110969
*Common Name:**	Bavachinin
IUPAC Name:	2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Bavachinin
Standard InCHIKey:	BVTZAHKRSBADDO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O4/c1-13(2)4-5-15-10-17-18(23)11-20(14-6-8-16(22)9-7-14)25-21(17)12-19(15)24-3/h4,6-12,22H,5H2,1-3H3
SMILES:	CC(=CCc1cc2c(=O)cc(c3ccc(cc3)O)oc2cc1OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458053
PubChem CID:	44584224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003503] 6-prenylated flavones

*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]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20663508]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24507928]
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]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544566]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1470	Fructus psoraleae corylifoliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28809	Cullen corylifolium	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	4
Ki	1

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[536095]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[536095]
NPT2	Others	Unspecified		IC50	=	3200.0	nM	PMID[536093]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Ki	=	175.5	nM	PMID[536094]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	IC50	=	488.8	nM	PMID[536094]

☑ 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 NPC110969 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	390
0.1-0.2	1732
0.2-0.3	4536
0.3-0.4	11727
0.4-0.5	6208
0.5-0.6	4156
0.6-0.7	5829
0.7-0.8	4238
0.8-0.85	1705
0.85-0.9	1433
0.9-0.95	654
0.95-1	89

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC226636
0.9926	High Similarity	NPC159275
0.9926	High Similarity	NPC172986
0.9926	High Similarity	NPC270883
0.9926	High Similarity	NPC241100
0.9926	High Similarity	NPC11561
0.9926	High Similarity	NPC261227
0.9853	High Similarity	NPC282300
0.9853	High Similarity	NPC156590
0.9853	High Similarity	NPC205006
0.9853	High Similarity	NPC118840
0.9853	High Similarity	NPC147688
0.9853	High Similarity	NPC103362
0.9853	High Similarity	NPC64908
0.9852	High Similarity	NPC301217
0.9852	High Similarity	NPC303633
0.9852	High Similarity	NPC96565
0.9852	High Similarity	NPC55018
0.9852	High Similarity	NPC216978
0.9852	High Similarity	NPC18260
0.9852	High Similarity	NPC217186
0.9852	High Similarity	NPC220062
0.9852	High Similarity	NPC53181
0.9852	High Similarity	NPC78913
0.9783	High Similarity	NPC234629
0.9783	High Similarity	NPC311741
0.9779	High Similarity	NPC475680
0.9779	High Similarity	NPC69769
0.9779	High Similarity	NPC305355
0.9779	High Similarity	NPC235239
0.9779	High Similarity	NPC150522
0.9778	High Similarity	NPC201395
0.971	High Similarity	NPC39329
0.971	High Similarity	NPC68104
0.971	High Similarity	NPC257097
0.971	High Similarity	NPC143896
0.971	High Similarity	NPC150408
0.971	High Similarity	NPC164980
0.971	High Similarity	NPC106985
0.971	High Similarity	NPC38219
0.971	High Similarity	NPC18585
0.971	High Similarity	NPC169591
0.971	High Similarity	NPC149026
0.971	High Similarity	NPC221432
0.971	High Similarity	NPC166138
0.971	High Similarity	NPC175504
0.971	High Similarity	NPC310130
0.971	High Similarity	NPC91560
0.971	High Similarity	NPC75049
0.9708	High Similarity	NPC3188
0.9704	High Similarity	NPC266597
0.9704	High Similarity	NPC250266
0.9643	High Similarity	NPC104406
0.9643	High Similarity	NPC79469
0.9643	High Similarity	NPC201731
0.9643	High Similarity	NPC110303
0.9643	High Similarity	NPC97716
0.9643	High Similarity	NPC23728
0.9643	High Similarity	NPC237635
0.9643	High Similarity	NPC24673
0.964	High Similarity	NPC319752
0.964	High Similarity	NPC473015
0.964	High Similarity	NPC216538
0.964	High Similarity	NPC197252
0.964	High Similarity	NPC273538
0.964	High Similarity	NPC469953
0.964	High Similarity	NPC209040
0.964	High Similarity	NPC473013
0.964	High Similarity	NPC236766
0.9638	High Similarity	NPC182852
0.9638	High Similarity	NPC32739
0.9638	High Similarity	NPC227579
0.9638	High Similarity	NPC66515
0.9638	High Similarity	NPC214236
0.9638	High Similarity	NPC78
0.9638	High Similarity	NPC166482
0.9638	High Similarity	NPC148757
0.9638	High Similarity	NPC324134
0.9638	High Similarity	NPC296917
0.9638	High Similarity	NPC78803
0.9638	High Similarity	NPC107572
0.9638	High Similarity	NPC59739
0.9638	High Similarity	NPC76372
0.9638	High Similarity	NPC62840
0.9638	High Similarity	NPC37496
0.9638	High Similarity	NPC166934
0.9638	High Similarity	NPC306829
0.9638	High Similarity	NPC194432
0.9638	High Similarity	NPC144499
0.9638	High Similarity	NPC220998
0.9638	High Similarity	NPC324436
0.9638	High Similarity	NPC76338
0.9638	High Similarity	NPC293852
0.9638	High Similarity	NPC125855
0.9638	High Similarity	NPC167624
0.9638	High Similarity	NPC217083
0.9638	High Similarity	NPC10937
0.9638	High Similarity	NPC228504
0.9638	High Similarity	NPC200694
0.9638	High Similarity	NPC40833
0.9638	High Similarity	NPC161506
0.9638	High Similarity	NPC265040
0.9638	High Similarity	NPC223500
0.9638	High Similarity	NPC1089
0.9638	High Similarity	NPC328164
0.9638	High Similarity	NPC64915
0.9638	High Similarity	NPC299080
0.9638	High Similarity	NPC177354
0.9635	High Similarity	NPC326109
0.9635	High Similarity	NPC48624
0.9635	High Similarity	NPC259166
0.9635	High Similarity	NPC144118
0.9635	High Similarity	NPC219917
0.9635	High Similarity	NPC215311
0.9635	High Similarity	NPC204985
0.9635	High Similarity	NPC213659
0.9635	High Similarity	NPC80962
0.9635	High Similarity	NPC172250
0.9632	High Similarity	NPC124269
0.963	High Similarity	NPC168105
0.963	High Similarity	NPC66349
0.963	High Similarity	NPC29353
0.963	High Similarity	NPC98115
0.963	High Similarity	NPC477244
0.963	High Similarity	NPC47815
0.963	High Similarity	NPC186838
0.963	High Similarity	NPC13408
0.963	High Similarity	NPC477243
0.963	High Similarity	NPC194281
0.963	High Similarity	NPC234133
0.963	High Similarity	NPC124784
0.963	High Similarity	NPC249606
0.963	High Similarity	NPC1486
0.963	High Similarity	NPC473887
0.963	High Similarity	NPC150399
0.963	High Similarity	NPC25287
0.963	High Similarity	NPC231772
0.963	High Similarity	NPC12165
0.963	High Similarity	NPC174999
0.963	High Similarity	NPC477242
0.963	High Similarity	NPC41461
0.963	High Similarity	NPC127447
0.963	High Similarity	NPC274109
0.9574	High Similarity	NPC6511
0.9574	High Similarity	NPC160821
0.9574	High Similarity	NPC168085
0.9574	High Similarity	NPC132592
0.9574	High Similarity	NPC266572
0.9571	High Similarity	NPC475052
0.9571	High Similarity	NPC312973
0.9571	High Similarity	NPC267375
0.9571	High Similarity	NPC88964
0.9571	High Similarity	NPC301276
0.9571	High Similarity	NPC306488
0.9571	High Similarity	NPC246948
0.9571	High Similarity	NPC111786
0.9571	High Similarity	NPC67805
0.9571	High Similarity	NPC470647
0.9571	High Similarity	NPC178343
0.9571	High Similarity	NPC474161
0.9571	High Similarity	NPC195621
0.9571	High Similarity	NPC54577
0.9571	High Similarity	NPC83357
0.9571	High Similarity	NPC5820
0.9571	High Similarity	NPC124729
0.9571	High Similarity	NPC142405
0.9571	High Similarity	NPC214774
0.9571	High Similarity	NPC176229
0.9571	High Similarity	NPC477955
0.9571	High Similarity	NPC20488
0.9571	High Similarity	NPC476088
0.9568	High Similarity	NPC9117
0.9568	High Similarity	NPC278249
0.9568	High Similarity	NPC478086
0.9568	High Similarity	NPC316816
0.9568	High Similarity	NPC223812
0.9568	High Similarity	NPC190637
0.9568	High Similarity	NPC185276
0.9568	High Similarity	NPC214166
0.9568	High Similarity	NPC107177
0.9568	High Similarity	NPC158874
0.9568	High Similarity	NPC219915
0.9568	High Similarity	NPC77794
0.9568	High Similarity	NPC81697
0.9568	High Similarity	NPC125894
0.9568	High Similarity	NPC212932
0.9568	High Similarity	NPC293053
0.9568	High Similarity	NPC24821
0.9568	High Similarity	NPC85162
0.9568	High Similarity	NPC11700
0.9565	High Similarity	NPC55832
0.9565	High Similarity	NPC469404
0.9565	High Similarity	NPC110038
0.9565	High Similarity	NPC268204
0.9565	High Similarity	NPC258630
0.9565	High Similarity	NPC52789
0.9565	High Similarity	NPC17170
0.9565	High Similarity	NPC96408
0.9565	High Similarity	NPC4743
0.9565	High Similarity	NPC156190

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 NPC110969 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	981
0.2-0.3	1464
0.3-0.4	2697
0.4-0.5	1876
0.5-0.6	1201
0.6-0.7	368
0.7-0.8	121
0.8-0.85	37
0.85-0.9	25
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.964	High Similarity	NPD4378	Clinical (unspecified phase)
0.95	High Similarity	NPD7410	Clinical (unspecified phase)
0.9348	High Similarity	NPD1549	Phase 2
0.9275	High Similarity	NPD1550	Clinical (unspecified phase)
0.9275	High Similarity	NPD1552	Clinical (unspecified phase)
0.927	High Similarity	NPD1510	Phase 2
0.9259	High Similarity	NPD1240	Approved
0.9203	High Similarity	NPD2796	Approved
0.9124	High Similarity	NPD1607	Approved
0.911	High Similarity	NPD7411	Suspended
0.9041	High Similarity	NPD4380	Phase 2
0.8986	High Similarity	NPD2393	Clinical (unspecified phase)
0.8933	High Similarity	NPD7075	Discontinued
0.8926	High Similarity	NPD8443	Clinical (unspecified phase)
0.8919	High Similarity	NPD6801	Discontinued
0.8859	High Similarity	NPD7819	Suspended
0.8859	High Similarity	NPD7096	Clinical (unspecified phase)
0.8759	High Similarity	NPD1511	Approved
0.8759	High Similarity	NPD6799	Approved
0.8741	High Similarity	NPD7421	Clinical (unspecified phase)
0.8733	High Similarity	NPD2801	Approved
0.8684	High Similarity	NPD4381	Clinical (unspecified phase)
0.8681	High Similarity	NPD3750	Approved
0.8667	High Similarity	NPD1934	Approved
0.8639	High Similarity	NPD1512	Approved
0.8618	High Similarity	NPD7768	Phase 2
0.859	High Similarity	NPD7852	Clinical (unspecified phase)
0.8533	High Similarity	NPD6599	Discontinued
0.8497	Intermediate Similarity	NPD3882	Suspended
0.8483	Intermediate Similarity	NPD2800	Approved
0.8483	Intermediate Similarity	NPD1243	Approved
0.8451	Intermediate Similarity	NPD6651	Approved
0.8429	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1551	Phase 2
0.8403	Intermediate Similarity	NPD2935	Discontinued
0.8397	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD920	Approved
0.8333	Intermediate Similarity	NPD2799	Discontinued
0.8333	Intermediate Similarity	NPD3748	Approved
0.8333	Intermediate Similarity	NPD5403	Approved
0.8323	Intermediate Similarity	NPD3749	Approved
0.8312	Intermediate Similarity	NPD3817	Phase 2
0.8311	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD2313	Discontinued
0.825	Intermediate Similarity	NPD3818	Discontinued
0.8239	Intermediate Similarity	NPD6166	Phase 2
0.8239	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD2344	Approved
0.8217	Intermediate Similarity	NPD5494	Approved
0.821	Intermediate Similarity	NPD5953	Discontinued
0.8201	Intermediate Similarity	NPD1203	Approved
0.82	Intermediate Similarity	NPD5401	Approved
0.82	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7286	Phase 2
0.8176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6232	Discontinued
0.8086	Intermediate Similarity	NPD7054	Approved
0.8082	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2534	Approved
0.8079	Intermediate Similarity	NPD2533	Approved
0.8079	Intermediate Similarity	NPD2532	Approved
0.8075	Intermediate Similarity	NPD7473	Discontinued
0.8049	Intermediate Similarity	NPD6559	Discontinued
0.8043	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD3268	Approved
0.8037	Intermediate Similarity	NPD7472	Approved
0.8037	Intermediate Similarity	NPD7074	Phase 3
0.8028	Intermediate Similarity	NPD6832	Phase 2
0.8025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.8014	Intermediate Similarity	NPD2798	Approved
0.8	Intermediate Similarity	NPD2309	Approved
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD3226	Approved
0.7986	Intermediate Similarity	NPD9717	Approved
0.7962	Intermediate Similarity	NPD5402	Approved
0.7959	Intermediate Similarity	NPD7033	Discontinued
0.7943	Intermediate Similarity	NPD2797	Approved
0.7939	Intermediate Similarity	NPD7251	Discontinued
0.7933	Intermediate Similarity	NPD4628	Phase 3
0.7931	Intermediate Similarity	NPD943	Approved
0.7925	Intermediate Similarity	NPD919	Approved
0.7914	Intermediate Similarity	NPD422	Phase 1
0.7905	Intermediate Similarity	NPD6099	Approved
0.7905	Intermediate Similarity	NPD6100	Approved
0.7902	Intermediate Similarity	NPD4908	Phase 1
0.7892	Intermediate Similarity	NPD7808	Phase 3
0.7866	Intermediate Similarity	NPD5844	Phase 1
0.7852	Intermediate Similarity	NPD2346	Discontinued
0.7838	Intermediate Similarity	NPD4308	Phase 3
0.7826	Intermediate Similarity	NPD1247	Approved
0.7815	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1610	Phase 2
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7390	Discontinued
0.7759	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5124	Phase 1
0.7755	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2654	Approved
0.7746	Intermediate Similarity	NPD4363	Phase 3
0.7746	Intermediate Similarity	NPD4360	Phase 2
0.7746	Intermediate Similarity	NPD3225	Approved
0.773	Intermediate Similarity	NPD3972	Approved
0.773	Intermediate Similarity	NPD3926	Phase 2
0.7711	Intermediate Similarity	NPD1729	Discontinued
0.7701	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4361	Phase 2
0.7692	Intermediate Similarity	NPD3267	Approved
0.7692	Intermediate Similarity	NPD3266	Approved
0.7658	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1933	Approved
0.7628	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD9545	Approved
0.7625	Intermediate Similarity	NPD4288	Approved
0.7609	Intermediate Similarity	NPD9493	Approved
0.7603	Intermediate Similarity	NPD4625	Phase 3
0.7568	Intermediate Similarity	NPD4307	Phase 2
0.7562	Intermediate Similarity	NPD1465	Phase 2
0.756	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1296	Phase 2
0.7547	Intermediate Similarity	NPD5889	Approved
0.7547	Intermediate Similarity	NPD5890	Approved
0.7532	Intermediate Similarity	NPD7458	Discontinued
0.7518	Intermediate Similarity	NPD1241	Discontinued
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6585	Discontinued
0.7483	Intermediate Similarity	NPD1608	Approved
0.7468	Intermediate Similarity	NPD7003	Approved
0.7455	Intermediate Similarity	NPD5710	Approved
0.7455	Intermediate Similarity	NPD5711	Approved
0.7448	Intermediate Similarity	NPD1470	Approved
0.7448	Intermediate Similarity	NPD1164	Approved
0.7434	Intermediate Similarity	NPD5406	Approved
0.7434	Intermediate Similarity	NPD5405	Approved
0.7434	Intermediate Similarity	NPD5408	Approved
0.7434	Intermediate Similarity	NPD5404	Approved
0.7432	Intermediate Similarity	NPD3764	Approved
0.7432	Intermediate Similarity	NPD411	Approved
0.7432	Intermediate Similarity	NPD6798	Discontinued
0.743	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1201	Approved
0.7412	Intermediate Similarity	NPD6104	Discontinued
0.7407	Intermediate Similarity	NPD2296	Approved
0.74	Intermediate Similarity	NPD447	Suspended
0.74	Intermediate Similarity	NPD230	Phase 1
0.7397	Intermediate Similarity	NPD1019	Discontinued
0.7389	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1471	Phase 3
0.7386	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7584	Approved
0.7365	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7229	Phase 3
0.7347	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5049	Phase 3
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.733	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4287	Approved
0.731	Intermediate Similarity	NPD4749	Approved
0.7308	Intermediate Similarity	NPD2354	Approved
0.7284	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4662	Approved
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4661	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.726	Intermediate Similarity	NPD1876	Approved
0.7255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1481	Phase 2
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7219	Intermediate Similarity	NPD3142	Approved
0.7219	Intermediate Similarity	NPD3140	Approved
0.7215	Intermediate Similarity	NPD7213	Phase 3
0.7215	Intermediate Similarity	NPD7212	Phase 2
0.7212	Intermediate Similarity	NPD6971	Discontinued
0.7208	Intermediate Similarity	NPD4477	Approved
0.7208	Intermediate Similarity	NPD4476	Approved
0.72	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3887	Approved
0.7186	Intermediate Similarity	NPD7199	Phase 2
0.7181	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1652	Phase 2
0.7178	Intermediate Similarity	NPD6279	Approved
0.7178	Intermediate Similarity	NPD7577	Discontinued
0.7178	Intermediate Similarity	NPD6280	Approved
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.7176	Intermediate Similarity	NPD7177	Discontinued
0.7172	Intermediate Similarity	NPD1535	Discovery
0.7171	Intermediate Similarity	NPD6355	Discontinued

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