NPASS Compound

Structure

CID157855 OpenBabel06191715532D 23 26 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 6.9282 -1.0000 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 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 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 -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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 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 4.3301 0.5000 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 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 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 18 2 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.11
Volume:	322.893
LogP:	5.114
LogD:	4.303
LogS:	-5.423
# Rotatable Bonds:	1
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	2.542
Fsp3:	0.15
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:	-4.644
MDCK Permeability:	1.5194883417279925e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.543

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	98.66698455810547%
Volume Distribution (VD):	0.58
Pgp-substrate:	2.0848515033721924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.864
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.845
CYP2D6-substrate:	0.766
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	2.856
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.938
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.518
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.641
Skin Sensitization:	0.245
Carcinogencity:	0.916
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC157855

Natural Product ID:	NPC157855
*Common Name:**	2'',2''-Dimethylchromene-[5'',6'':7,8]-Flavone
IUPAC Name:	8,8-dimethyl-2-phenylpyrano[2,3-f]chromen-4-one
Synonyms:
Standard InCHIKey:	RBKWJAHRWPDNPM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O3/c1-20(2)11-10-15-17(23-20)9-8-14-16(21)12-18(22-19(14)15)13-6-4-3-5-7-13/h3-12H,1-2H3
SMILES:	CC1(C)C=Cc2c(ccc3c(=O)cc(c4ccccc4)oc23)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3401058
PubChem CID:	11358607
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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]
NPO21131	Lepista nuda	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21131	Lepista nuda	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21535	Bursera leptophloeos	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21131	Lepista nuda	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23181	Ursinia eckloniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19409	Vespa crabro	Species	Vespidae	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	2

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	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	=	1.6	n.a.	PMID[537089]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	99.0	%	PMID[537089]

☑ 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 NPC157855 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	509
0.1-0.2	1954
0.2-0.3	5326
0.3-0.4	12508
0.4-0.5	4879
0.5-0.6	5022
0.6-0.7	5830
0.7-0.8	3914
0.8-0.85	1729
0.85-0.9	835
0.9-0.95	177
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9774	High Similarity	NPC17848
0.963	High Similarity	NPC472409
0.9624	High Similarity	NPC161196
0.9562	High Similarity	NPC59522
0.9549	High Similarity	NPC46869
0.9493	High Similarity	NPC179970
0.9489	High Similarity	NPC217083
0.9489	High Similarity	NPC299080
0.9489	High Similarity	NPC78803
0.9489	High Similarity	NPC293852
0.9489	High Similarity	NPC59739
0.9489	High Similarity	NPC62840
0.9489	High Similarity	NPC214236
0.9485	High Similarity	NPC305355
0.9485	High Similarity	NPC475680
0.947	High Similarity	NPC229646
0.942	High Similarity	NPC38219
0.9416	High Similarity	NPC52576
0.9416	High Similarity	NPC156590
0.9416	High Similarity	NPC205006
0.9416	High Similarity	NPC103362
0.9416	High Similarity	NPC118840
0.9416	High Similarity	NPC147688
0.9416	High Similarity	NPC64908
0.9412	High Similarity	NPC11566
0.9398	High Similarity	NPC292998
0.9394	High Similarity	NPC284424
0.9357	High Similarity	NPC237635
0.9357	High Similarity	NPC79469
0.9357	High Similarity	NPC24673
0.9357	High Similarity	NPC201731
0.9357	High Similarity	NPC97716
0.9357	High Similarity	NPC104406
0.9348	High Similarity	NPC226636
0.9348	High Similarity	NPC11561
0.9343	High Similarity	NPC270883
0.9343	High Similarity	NPC172986
0.9343	High Similarity	NPC261227
0.9343	High Similarity	NPC150522
0.9343	High Similarity	NPC235239
0.9333	High Similarity	NPC254741
0.9323	High Similarity	NPC473655
0.9323	High Similarity	NPC101294
0.9291	High Similarity	NPC266572
0.9291	High Similarity	NPC6511
0.9281	High Similarity	NPC17262
0.9281	High Similarity	NPC219915
0.9275	High Similarity	NPC110969
0.927	High Similarity	NPC55018
0.927	High Similarity	NPC216978
0.927	High Similarity	NPC96565
0.927	High Similarity	NPC301217
0.927	High Similarity	NPC220062
0.927	High Similarity	NPC303633
0.9265	High Similarity	NPC259685
0.9248	High Similarity	NPC278556
0.922	High Similarity	NPC166757
0.922	High Similarity	NPC110303
0.922	High Similarity	NPC180477
0.922	High Similarity	NPC14001
0.922	High Similarity	NPC23728
0.9214	High Similarity	NPC311741
0.9214	High Similarity	NPC257236
0.9214	High Similarity	NPC234629
0.9214	High Similarity	NPC278175
0.9214	High Similarity	NPC319752
0.9209	High Similarity	NPC147145
0.9209	High Similarity	NPC144499
0.9203	High Similarity	NPC241100
0.9203	High Similarity	NPC159275
0.9203	High Similarity	NPC69769
0.9197	High Similarity	NPC201395
0.9185	High Similarity	NPC125269
0.9161	High Similarity	NPC188403
0.9161	High Similarity	NPC5840
0.9161	High Similarity	NPC189270
0.9155	High Similarity	NPC161191
0.9155	High Similarity	NPC321623
0.9155	High Similarity	NPC160821
0.9155	High Similarity	NPC244407
0.9155	High Similarity	NPC189087
0.9155	High Similarity	NPC132592
0.9149	High Similarity	NPC111786
0.9149	High Similarity	NPC214774
0.9149	High Similarity	NPC220418
0.9149	High Similarity	NPC301276
0.9149	High Similarity	NPC475052
0.9149	High Similarity	NPC83357
0.9149	High Similarity	NPC312973
0.9149	High Similarity	NPC20488
0.9149	High Similarity	NPC474161
0.9149	High Similarity	NPC267375
0.9149	High Similarity	NPC246948
0.9149	High Similarity	NPC54577
0.9149	High Similarity	NPC142405
0.9149	High Similarity	NPC67805
0.9149	High Similarity	NPC176229
0.9149	High Similarity	NPC476088
0.9149	High Similarity	NPC195621
0.9149	High Similarity	NPC470647
0.9149	High Similarity	NPC57470
0.9149	High Similarity	NPC88964
0.9143	High Similarity	NPC18585
0.9143	High Similarity	NPC166138
0.9143	High Similarity	NPC106985
0.9137	High Similarity	NPC282300
0.9137	High Similarity	NPC14871
0.913	High Similarity	NPC78913
0.913	High Similarity	NPC473209
0.913	High Similarity	NPC53181
0.913	High Similarity	NPC18260
0.913	High Similarity	NPC217186
0.9124	High Similarity	NPC253616
0.9124	High Similarity	NPC228661
0.9124	High Similarity	NPC38153
0.9124	High Similarity	NPC103001
0.9118	High Similarity	NPC151113
0.9118	High Similarity	NPC99854
0.9111	High Similarity	NPC223354
0.9091	High Similarity	NPC5173
0.9091	High Similarity	NPC125887
0.9085	High Similarity	NPC282335
0.9085	High Similarity	NPC473077
0.9085	High Similarity	NPC249942
0.9085	High Similarity	NPC297886
0.9085	High Similarity	NPC283234
0.9085	High Similarity	NPC218300
0.9085	High Similarity	NPC296998
0.9078	High Similarity	NPC209040
0.9078	High Similarity	NPC469953
0.9071	High Similarity	NPC200694
0.9065	High Similarity	NPC171094
0.9058	High Similarity	NPC470669
0.9058	High Similarity	NPC470668
0.9051	High Similarity	NPC61546
0.9051	High Similarity	NPC13408
0.9051	High Similarity	NPC268081
0.9051	High Similarity	NPC72452
0.9037	High Similarity	NPC182428
0.9028	High Similarity	NPC471984
0.9028	High Similarity	NPC151973
0.9023	High Similarity	NPC211120
0.9021	High Similarity	NPC161864
0.9021	High Similarity	NPC272194
0.9021	High Similarity	NPC469933
0.9021	High Similarity	NPC296869
0.9021	High Similarity	NPC208303
0.9015	High Similarity	NPC41721
0.9014	High Similarity	NPC124729
0.9014	High Similarity	NPC477955
0.9014	High Similarity	NPC329678
0.9007	High Similarity	NPC11700
0.9007	High Similarity	NPC75049
0.9007	High Similarity	NPC164980
0.9007	High Similarity	NPC190637
0.9007	High Similarity	NPC212932
0.9007	High Similarity	NPC68104
0.9007	High Similarity	NPC169591
0.9007	High Similarity	NPC175504
0.9007	High Similarity	NPC221432
0.9007	High Similarity	NPC478086
0.9007	High Similarity	NPC150408
0.9007	High Similarity	NPC9117
0.9007	High Similarity	NPC149026
0.9007	High Similarity	NPC293053
0.9007	High Similarity	NPC39329
0.9007	High Similarity	NPC214166
0.9007	High Similarity	NPC143896
0.9007	High Similarity	NPC24821
0.9007	High Similarity	NPC310130
0.9007	High Similarity	NPC257097
0.9007	High Similarity	NPC91560
0.9007	High Similarity	NPC316816
0.9	High Similarity	NPC3188
0.9	High Similarity	NPC22467
0.8993	High Similarity	NPC473076
0.8993	High Similarity	NPC23257
0.8993	High Similarity	NPC136095
0.8986	High Similarity	NPC266597
0.8986	High Similarity	NPC317119
0.8986	High Similarity	NPC250266
0.8973	High Similarity	NPC472408
0.8971	High Similarity	NPC57601
0.8958	High Similarity	NPC10027
0.8958	High Similarity	NPC469932
0.8958	High Similarity	NPC221868
0.8958	High Similarity	NPC65775
0.8958	High Similarity	NPC164299
0.8958	High Similarity	NPC37208
0.8958	High Similarity	NPC474052
0.8951	High Similarity	NPC140120
0.8951	High Similarity	NPC471285
0.8947	High Similarity	NPC473907
0.8944	High Similarity	NPC216538
0.8944	High Similarity	NPC131579
0.8944	High Similarity	NPC273538
0.8944	High Similarity	NPC473013
0.8944	High Similarity	NPC326500
0.8944	High Similarity	NPC236766
0.8944	High Similarity	NPC473015

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 NPC157855 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	456
0.1-0.2	1024
0.2-0.3	1456
0.3-0.4	2816
0.4-0.5	1892
0.5-0.6	1037
0.6-0.7	314
0.7-0.8	103
0.8-0.85	42
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD2796	Approved
0.9214	High Similarity	NPD7410	Clinical (unspecified phase)
0.8944	High Similarity	NPD4378	Clinical (unspecified phase)
0.8723	High Similarity	NPD1243	Approved
0.8707	High Similarity	NPD7411	Suspended
0.8686	High Similarity	NPD1240	Approved
0.8652	High Similarity	NPD1549	Phase 2
0.8582	High Similarity	NPD1550	Clinical (unspecified phase)
0.8582	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD3748	Approved
0.8571	High Similarity	NPD1510	Phase 2
0.8561	High Similarity	NPD1607	Approved
0.8523	High Similarity	NPD6801	Discontinued
0.8514	High Similarity	NPD4380	Phase 2
0.8483	Intermediate Similarity	NPD6799	Approved
0.8467	Intermediate Similarity	NPD7819	Suspended
0.8467	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD5494	Approved
0.8311	Intermediate Similarity	NPD920	Approved
0.8301	Intermediate Similarity	NPD7075	Discontinued
0.8299	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD3750	Approved
0.8267	Intermediate Similarity	NPD6599	Discontinued
0.8231	Intermediate Similarity	NPD1511	Approved
0.8207	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD5403	Approved
0.8182	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5401	Approved
0.8148	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1512	Approved
0.8117	Intermediate Similarity	NPD7768	Phase 2
0.8105	Intermediate Similarity	NPD2801	Approved
0.8101	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3749	Approved
0.8056	Intermediate Similarity	NPD2799	Discontinued
0.8052	Intermediate Similarity	NPD3817	Phase 2
0.8039	Intermediate Similarity	NPD1934	Approved
0.8014	Intermediate Similarity	NPD2313	Discontinued
0.8014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6832	Phase 2
0.7986	Intermediate Similarity	NPD2798	Approved
0.7959	Intermediate Similarity	NPD2800	Approved
0.795	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD919	Approved
0.7885	Intermediate Similarity	NPD3882	Suspended
0.7826	Intermediate Similarity	NPD3972	Approved
0.7823	Intermediate Similarity	NPD2344	Approved
0.7821	Intermediate Similarity	NPD5402	Approved
0.7799	Intermediate Similarity	NPD1247	Approved
0.7793	Intermediate Similarity	NPD6651	Approved
0.7792	Intermediate Similarity	NPD6585	Discontinued
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7778	Intermediate Similarity	NPD4307	Phase 2
0.777	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6166	Phase 2
0.7764	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1551	Phase 2
0.7755	Intermediate Similarity	NPD2935	Discontinued
0.7718	Intermediate Similarity	NPD2654	Approved
0.7702	Intermediate Similarity	NPD3926	Phase 2
0.7669	Intermediate Similarity	NPD3818	Discontinued
0.766	Intermediate Similarity	NPD2797	Approved
0.766	Intermediate Similarity	NPD1203	Approved
0.7651	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3268	Approved
0.7639	Intermediate Similarity	NPD1296	Phase 2
0.7636	Intermediate Similarity	NPD5953	Discontinued
0.7635	Intermediate Similarity	NPD6099	Approved
0.7635	Intermediate Similarity	NPD6100	Approved
0.7628	Intermediate Similarity	NPD5890	Approved
0.7628	Intermediate Similarity	NPD5889	Approved
0.7622	Intermediate Similarity	NPD7054	Approved
0.7622	Intermediate Similarity	NPD7286	Phase 2
0.7616	Intermediate Similarity	NPD2309	Approved
0.7613	Intermediate Similarity	NPD3226	Approved
0.7612	Intermediate Similarity	NPD1241	Discontinued
0.7603	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD5124	Phase 1
0.7603	Intermediate Similarity	NPD1933	Approved
0.7597	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3225	Approved
0.7584	Intermediate Similarity	NPD2346	Discontinued
0.7576	Intermediate Similarity	NPD7472	Approved
0.7576	Intermediate Similarity	NPD7074	Phase 3
0.7571	Intermediate Similarity	NPD9717	Approved
0.7568	Intermediate Similarity	NPD7033	Discontinued
0.7568	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4308	Phase 3
0.755	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6232	Discontinued
0.753	Intermediate Similarity	NPD6797	Phase 2
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD422	Phase 1
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7484	Intermediate Similarity	NPD4288	Approved
0.7483	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD17	Approved
0.7468	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD2533	Approved
0.7467	Intermediate Similarity	NPD1471	Phase 3
0.7464	Intermediate Similarity	NPD1548	Phase 1
0.744	Intermediate Similarity	NPD7808	Phase 3
0.7434	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4628	Phase 3
0.7415	Intermediate Similarity	NPD943	Approved
0.7403	Intermediate Similarity	NPD7390	Discontinued
0.7386	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4908	Phase 1
0.7361	Intermediate Similarity	NPD1019	Discontinued
0.7351	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2353	Approved
0.7343	Intermediate Similarity	NPD1876	Approved
0.7337	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7324	Intermediate Similarity	NPD1608	Approved
0.7314	Intermediate Similarity	NPD4360	Phase 2
0.7314	Intermediate Similarity	NPD4363	Phase 3
0.7297	Intermediate Similarity	NPD3140	Approved
0.7297	Intermediate Similarity	NPD3142	Approved
0.7273	Intermediate Similarity	NPD3887	Approved
0.7262	Intermediate Similarity	NPD1729	Discontinued
0.726	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1610	Phase 2
0.725	Intermediate Similarity	NPD6279	Approved
0.725	Intermediate Similarity	NPD6280	Approved
0.7246	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2403	Approved
0.7208	Intermediate Similarity	NPD7003	Approved
0.7205	Intermediate Similarity	NPD1465	Phase 2
0.7197	Intermediate Similarity	NPD5049	Phase 3
0.7188	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4361	Phase 2
0.7175	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7458	Discontinued
0.7163	Intermediate Similarity	NPD1651	Approved
0.7161	Intermediate Similarity	NPD2354	Approved
0.7153	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4661	Approved
0.7134	Intermediate Similarity	NPD4662	Approved
0.7124	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD9545	Approved
0.7086	Intermediate Similarity	NPD4287	Approved
0.708	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6104	Discontinued
0.7071	Intermediate Similarity	NPD9493	Approved
0.7065	Intermediate Similarity	NPD7584	Approved
0.7063	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7055	Intermediate Similarity	NPD2296	Approved
0.7055	Intermediate Similarity	NPD1164	Approved
0.7047	Intermediate Similarity	NPD6798	Discontinued
0.7047	Intermediate Similarity	NPD411	Approved
0.7047	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD6844	Discontinued
0.7037	Intermediate Similarity	NPD7577	Discontinued
0.7034	Intermediate Similarity	NPD4749	Approved
0.7025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD447	Suspended
0.7014	Intermediate Similarity	NPD1201	Approved
0.7006	Intermediate Similarity	NPD7229	Phase 3
0.7006	Intermediate Similarity	NPD6808	Phase 2
0.7006	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6273	Approved
0.6948	Remote Similarity	NPD4476	Approved
0.6948	Remote Similarity	NPD4477	Approved
0.6941	Remote Similarity	NPD3751	Discontinued
0.6939	Remote Similarity	NPD1470	Approved
0.6937	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5710	Approved
0.6905	Remote Similarity	NPD5711	Approved
0.6905	Remote Similarity	NPD3787	Discontinued
0.6897	Remote Similarity	NPD1281	Approved
0.6889	Remote Similarity	NPD9697	Approved
0.6887	Remote Similarity	NPD8032	Phase 2
0.6879	Remote Similarity	NPD7466	Approved
0.6867	Remote Similarity	NPD6971	Discontinued
0.6866	Remote Similarity	NPD9261	Approved
0.6864	Remote Similarity	NPD5242	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