NPASS Compound

Structure

CID161196 OpenBabel06191715532D 28 30 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 6.0622 3.5000 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 3.4641 -1.0000 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 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 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 5.1962 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 5.1962 3.0000 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 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 23 1 0 0 0 0 2 23 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 25 1 0 0 0 0 19 28 1 0 0 0 0 20 21 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.16
Volume:	400.918
LogP:	4.591
LogD:	4.573
LogS:	-5.91
# Rotatable Bonds:	6
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.411
Synthetic Accessibility Score:	2.913
Fsp3:	0.261
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:	1.7900407328852452e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	100.00965881347656%
Volume Distribution (VD):	0.369
Pgp-substrate:	3.194020986557007%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.779
CYP2D6-inhibitor:	0.946
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.701

ADMET: Excretion

Clearance (CL):	5.46
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.186
Skin Sensitization:	0.479
Carcinogencity:	0.892
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC161196

Natural Product ID:	NPC161196
*Common Name:**	7,2',6'-Trimethoxy-6'',6''-Dimethylpyrano-(3',4':2'',3'')-Chalcone
IUPAC Name:	(Z)-1-(5,7-dimethoxy-2,2-dimethylchromen-6-yl)-3-methoxy-3-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	KLIBVTLWIJEYNK-AQTBWJFISA-N
Standard InCHI:	InChI=1S/C23H24O5/c1-23(2)12-11-16-19(28-23)14-20(26-4)21(22(16)27-5)17(24)13-18(25-3)15-9-7-6-8-10-15/h6-14H,1-5H3/b18-13-
SMILES:	CO/C(=CC(=O)c1c(OC)cc2c(c1OC)C=CC(O2)(C)C)/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508495
PubChem CID:	10452362
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	1.2	ug ml-1	PMID[495820]
NPT27	Others	Unspecified		IC50	=	9.6	ug.mL-1	PMID[495820]
NPT2	Others	Unspecified		Ratio	=	8.0	n.a.	PMID[495820]

☑ 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 NPC161196 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	437
0.1-0.2	1645
0.2-0.3	4450
0.3-0.4	11639
0.4-0.5	6414
0.5-0.6	4164
0.6-0.7	6241
0.7-0.8	4774
0.8-0.85	1664
0.85-0.9	885
0.9-0.95	368
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC17848
0.9771	High Similarity	NPC46869
0.9701	High Similarity	NPC150522
0.9692	High Similarity	NPC473655
0.9692	High Similarity	NPC101294
0.963	High Similarity	NPC103362
0.9627	High Similarity	NPC11566
0.9624	High Similarity	NPC157855
0.9624	High Similarity	NPC259685
0.9615	High Similarity	NPC278556
0.9559	High Similarity	NPC226636
0.9559	High Similarity	NPC11561
0.9556	High Similarity	NPC159275
0.9556	High Similarity	NPC472409
0.9556	High Similarity	NPC241100
0.9549	High Similarity	NPC254741
0.9542	High Similarity	NPC229646
0.9489	High Similarity	NPC59522
0.9485	High Similarity	NPC118840
0.9485	High Similarity	NPC64908
0.9485	High Similarity	NPC147688
0.9485	High Similarity	NPC282300
0.9485	High Similarity	NPC52576
0.9485	High Similarity	NPC110969
0.9485	High Similarity	NPC205006
0.9485	High Similarity	NPC156590
0.9481	High Similarity	NPC96565
0.9481	High Similarity	NPC216978
0.9481	High Similarity	NPC301217
0.9481	High Similarity	NPC303633
0.9481	High Similarity	NPC53181
0.9481	High Similarity	NPC217186
0.9481	High Similarity	NPC18260
0.9481	High Similarity	NPC55018
0.9481	High Similarity	NPC220062
0.9481	High Similarity	NPC78913
0.9474	High Similarity	NPC99854
0.947	High Similarity	NPC292998
0.9466	High Similarity	NPC284424
0.942	High Similarity	NPC234629
0.942	High Similarity	NPC311741
0.942	High Similarity	NPC179970
0.9416	High Similarity	NPC78803
0.9416	High Similarity	NPC59739
0.9416	High Similarity	NPC214236
0.9416	High Similarity	NPC62840
0.9416	High Similarity	NPC217083
0.9416	High Similarity	NPC299080
0.9416	High Similarity	NPC293852
0.9416	High Similarity	NPC147145
0.9412	High Similarity	NPC172986
0.9412	High Similarity	NPC305355
0.9412	High Similarity	NPC235239
0.9412	High Similarity	NPC261227
0.9412	High Similarity	NPC475680
0.9412	High Similarity	NPC270883
0.9407	High Similarity	NPC201395
0.9403	High Similarity	NPC72452
0.9403	High Similarity	NPC61546
0.9398	High Similarity	NPC125269
0.9353	High Similarity	NPC88964
0.9353	High Similarity	NPC470647
0.9353	High Similarity	NPC312973
0.9353	High Similarity	NPC176229
0.9353	High Similarity	NPC301276
0.9353	High Similarity	NPC142405
0.9353	High Similarity	NPC54577
0.9353	High Similarity	NPC67805
0.9353	High Similarity	NPC475052
0.9353	High Similarity	NPC83357
0.9353	High Similarity	NPC246948
0.9353	High Similarity	NPC111786
0.9353	High Similarity	NPC20488
0.9353	High Similarity	NPC195621
0.9353	High Similarity	NPC267375
0.9353	High Similarity	NPC124729
0.9353	High Similarity	NPC214774
0.9348	High Similarity	NPC214166
0.9348	High Similarity	NPC18585
0.9348	High Similarity	NPC38219
0.9348	High Similarity	NPC478086
0.9348	High Similarity	NPC219915
0.9348	High Similarity	NPC106985
0.9348	High Similarity	NPC316816
0.9348	High Similarity	NPC166138
0.9348	High Similarity	NPC17262
0.9343	High Similarity	NPC22467
0.9338	High Similarity	NPC473209
0.9338	High Similarity	NPC23257
0.9333	High Similarity	NPC253616
0.9323	High Similarity	NPC223354
0.9308	High Similarity	NPC473907
0.9286	High Similarity	NPC97716
0.9286	High Similarity	NPC23728
0.9286	High Similarity	NPC283234
0.9286	High Similarity	NPC296998
0.9286	High Similarity	NPC201731
0.9286	High Similarity	NPC24673
0.9286	High Similarity	NPC237635
0.9286	High Similarity	NPC110303
0.9286	High Similarity	NPC104406
0.9286	High Similarity	NPC473077
0.9286	High Similarity	NPC79469
0.9281	High Similarity	NPC273538
0.9281	High Similarity	NPC469953
0.9281	High Similarity	NPC216538
0.9281	High Similarity	NPC319752
0.9281	High Similarity	NPC131568
0.9281	High Similarity	NPC209040
0.9281	High Similarity	NPC131579
0.9275	High Similarity	NPC167624
0.9275	High Similarity	NPC107572
0.9275	High Similarity	NPC227579
0.9275	High Similarity	NPC324134
0.9275	High Similarity	NPC223500
0.9275	High Similarity	NPC166934
0.9275	High Similarity	NPC144499
0.9275	High Similarity	NPC1089
0.9275	High Similarity	NPC37496
0.9275	High Similarity	NPC76338
0.9275	High Similarity	NPC40833
0.9275	High Similarity	NPC324436
0.9275	High Similarity	NPC32739
0.9275	High Similarity	NPC265040
0.9275	High Similarity	NPC328164
0.9275	High Similarity	NPC10937
0.9275	High Similarity	NPC306829
0.9275	High Similarity	NPC194432
0.9275	High Similarity	NPC200694
0.9275	High Similarity	NPC76372
0.9275	High Similarity	NPC161506
0.9275	High Similarity	NPC148757
0.9275	High Similarity	NPC125855
0.9275	High Similarity	NPC296917
0.9275	High Similarity	NPC66515
0.9275	High Similarity	NPC228504
0.9275	High Similarity	NPC78
0.9275	High Similarity	NPC182852
0.9275	High Similarity	NPC166482
0.9275	High Similarity	NPC220998
0.9275	High Similarity	NPC177354
0.9275	High Similarity	NPC64915
0.927	High Similarity	NPC471587
0.927	High Similarity	NPC171094
0.927	High Similarity	NPC69769
0.9265	High Similarity	NPC248995
0.9265	High Similarity	NPC272844
0.9265	High Similarity	NPC470669
0.9265	High Similarity	NPC276905
0.9265	High Similarity	NPC254168
0.9265	High Similarity	NPC470668
0.9265	High Similarity	NPC131130
0.9259	High Similarity	NPC268081
0.9259	High Similarity	NPC47815
0.9259	High Similarity	NPC174999
0.9259	High Similarity	NPC473887
0.9259	High Similarity	NPC13408
0.9259	High Similarity	NPC127447
0.9259	High Similarity	NPC29353
0.9259	High Similarity	NPC194281
0.9259	High Similarity	NPC124784
0.9259	High Similarity	NPC234133
0.9259	High Similarity	NPC231772
0.9248	High Similarity	NPC182428
0.9237	High Similarity	NPC211120
0.9237	High Similarity	NPC473894
0.9231	High Similarity	NPC41721
0.9231	High Similarity	NPC475496
0.9231	High Similarity	NPC49852
0.922	High Similarity	NPC160821
0.922	High Similarity	NPC6511
0.922	High Similarity	NPC132592
0.922	High Similarity	NPC244407
0.922	High Similarity	NPC296869
0.922	High Similarity	NPC161191
0.922	High Similarity	NPC321623
0.922	High Similarity	NPC266572
0.922	High Similarity	NPC189087
0.9214	High Similarity	NPC178343
0.9214	High Similarity	NPC285630
0.9214	High Similarity	NPC474161
0.9214	High Similarity	NPC477955
0.9214	High Similarity	NPC5820
0.9214	High Similarity	NPC306488
0.9214	High Similarity	NPC476088
0.9214	High Similarity	NPC127059
0.9209	High Similarity	NPC75049
0.9209	High Similarity	NPC24821
0.9209	High Similarity	NPC107177
0.9209	High Similarity	NPC68104
0.9209	High Similarity	NPC169591
0.9209	High Similarity	NPC185276
0.9209	High Similarity	NPC293053
0.9209	High Similarity	NPC223812
0.9209	High Similarity	NPC164980
0.9209	High Similarity	NPC149026
0.9209	High Similarity	NPC77794
0.9209	High Similarity	NPC85162
0.9209	High Similarity	NPC81697
0.9209	High Similarity	NPC39329

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 NPC161196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	966
0.2-0.3	1505
0.3-0.4	2692
0.4-0.5	1850
0.5-0.6	1133
0.6-0.7	445
0.7-0.8	137
0.8-0.85	27
0.85-0.9	14
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9403	High Similarity	NPD2796	Approved
0.9281	High Similarity	NPD4378	Clinical (unspecified phase)
0.9143	High Similarity	NPD7410	Clinical (unspecified phase)
0.8913	High Similarity	NPD1550	Clinical (unspecified phase)
0.8913	High Similarity	NPD1552	Clinical (unspecified phase)
0.8849	High Similarity	NPD1549	Phase 2
0.8768	High Similarity	NPD1510	Phase 2
0.8767	High Similarity	NPD7411	Suspended
0.875	High Similarity	NPD1240	Approved
0.8707	High Similarity	NPD6801	Discontinued
0.8671	High Similarity	NPD6799	Approved
0.8652	High Similarity	NPD1243	Approved
0.8649	High Similarity	NPD2393	Clinical (unspecified phase)
0.8649	High Similarity	NPD7096	Clinical (unspecified phase)
0.8649	High Similarity	NPD7819	Suspended
0.8623	High Similarity	NPD1607	Approved
0.8591	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD4380	Phase 2
0.85	High Similarity	NPD3748	Approved
0.8493	Intermediate Similarity	NPD920	Approved
0.8477	Intermediate Similarity	NPD7075	Discontinued
0.8472	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD6599	Discontinued
0.8414	Intermediate Similarity	NPD1511	Approved
0.84	Intermediate Similarity	NPD2801	Approved
0.8392	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD5494	Approved
0.8356	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1512	Approved
0.8235	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD3750	Approved
0.8188	Intermediate Similarity	NPD6832	Phase 2
0.817	Intermediate Similarity	NPD7768	Phase 2
0.8153	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2800	Approved
0.8121	Intermediate Similarity	NPD5403	Approved
0.8113	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD2799	Discontinued
0.8108	Intermediate Similarity	NPD5401	Approved
0.8099	Intermediate Similarity	NPD6651	Approved
0.8077	Intermediate Similarity	NPD6959	Discontinued
0.8071	Intermediate Similarity	NPD2313	Discontinued
0.8069	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD919	Approved
0.8052	Intermediate Similarity	NPD3882	Suspended
0.8014	Intermediate Similarity	NPD2654	Approved
0.8	Intermediate Similarity	NPD3749	Approved
0.7971	Intermediate Similarity	NPD3267	Approved
0.7971	Intermediate Similarity	NPD3266	Approved
0.7962	Intermediate Similarity	NPD1247	Approved
0.7931	Intermediate Similarity	NPD2935	Discontinued
0.7931	Intermediate Similarity	NPD1551	Phase 2
0.7925	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6166	Phase 2
0.7925	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2798	Approved
0.7914	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD3972	Approved
0.7862	Intermediate Similarity	NPD3926	Phase 2
0.7862	Intermediate Similarity	NPD7033	Discontinued
0.7832	Intermediate Similarity	NPD4307	Phase 2
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7817	Intermediate Similarity	NPD3268	Approved
0.7817	Intermediate Similarity	NPD1296	Phase 2
0.7799	Intermediate Similarity	NPD6232	Discontinued
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7778	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD1933	Approved
0.7764	Intermediate Similarity	NPD7473	Discontinued
0.7763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5402	Approved
0.7755	Intermediate Similarity	NPD2344	Approved
0.7748	Intermediate Similarity	NPD2533	Approved
0.7748	Intermediate Similarity	NPD2532	Approved
0.7748	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD7074	Phase 3
0.773	Intermediate Similarity	NPD7472	Approved
0.7727	Intermediate Similarity	NPD6585	Discontinued
0.7718	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2797	Approved
0.7714	Intermediate Similarity	NPD1203	Approved
0.7692	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD6099	Approved
0.7683	Intermediate Similarity	NPD6797	Phase 2
0.7677	Intermediate Similarity	NPD5890	Approved
0.7677	Intermediate Similarity	NPD5889	Approved
0.7669	Intermediate Similarity	NPD1241	Discontinued
0.7662	Intermediate Similarity	NPD3226	Approved
0.7655	Intermediate Similarity	NPD5124	Phase 1
0.7655	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1548	Phase 1
0.7636	Intermediate Similarity	NPD6559	Discontinued
0.7636	Intermediate Similarity	NPD7251	Discontinued
0.7635	Intermediate Similarity	NPD2346	Discontinued
0.7626	Intermediate Similarity	NPD9717	Approved
0.7619	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4308	Phase 3
0.76	Intermediate Similarity	NPD4628	Phase 3
0.7595	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7808	Phase 3
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7554	Intermediate Similarity	NPD422	Phase 1
0.7552	Intermediate Similarity	NPD4908	Phase 1
0.755	Intermediate Similarity	NPD2309	Approved
0.7536	Intermediate Similarity	NPD17	Approved
0.7535	Intermediate Similarity	NPD1019	Discontinued
0.7518	Intermediate Similarity	NPD3225	Approved
0.7517	Intermediate Similarity	NPD1471	Phase 3
0.7485	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2403	Approved
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD943	Approved
0.7457	Intermediate Similarity	NPD4360	Phase 2
0.7457	Intermediate Similarity	NPD4363	Phase 3
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7390	Discontinued
0.7434	Intermediate Similarity	NPD3887	Approved
0.7431	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1610	Phase 2
0.7421	Intermediate Similarity	NPD4288	Approved
0.7414	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4361	Phase 2
0.74	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2353	Approved
0.7394	Intermediate Similarity	NPD1876	Approved
0.7394	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4625	Phase 3
0.7376	Intermediate Similarity	NPD1608	Approved
0.7371	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3140	Approved
0.7347	Intermediate Similarity	NPD3142	Approved
0.7338	Intermediate Similarity	NPD1651	Approved
0.7333	Intermediate Similarity	NPD5535	Approved
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.732	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1729	Discontinued
0.7296	Intermediate Similarity	NPD6279	Approved
0.7296	Intermediate Similarity	NPD6280	Approved
0.7256	Intermediate Similarity	NPD7229	Phase 3
0.7244	Intermediate Similarity	NPD5049	Phase 3
0.7219	Intermediate Similarity	NPD6104	Discontinued
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7208	Intermediate Similarity	NPD2354	Approved
0.7179	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4661	Approved
0.7171	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5710	Approved
0.7152	Intermediate Similarity	NPD6808	Phase 2
0.7152	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD7003	Approved
0.7124	Intermediate Similarity	NPD2424	Discontinued
0.7122	Intermediate Similarity	NPD9493	Approved
0.7115	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4477	Approved
0.7105	Intermediate Similarity	NPD4476	Approved
0.7104	Intermediate Similarity	NPD7584	Approved
0.7095	Intermediate Similarity	NPD411	Approved
0.7095	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD7199	Phase 2
0.7083	Intermediate Similarity	NPD4749	Approved
0.7081	Intermediate Similarity	NPD6844	Discontinued
0.7078	Intermediate Similarity	NPD1652	Phase 2
0.7075	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6355	Discontinued
0.7067	Intermediate Similarity	NPD447	Suspended
0.7063	Intermediate Similarity	NPD1281	Approved
0.7063	Intermediate Similarity	NPD1201	Approved
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3787	Discontinued
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4287	Approved
0.7021	Intermediate Similarity	NPD1894	Discontinued
0.7012	Intermediate Similarity	NPD6971	Discontinued
0.7007	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5242	Approved
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD2296	Approved
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD5408	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data