NPASS Compound

Structure

NPC229442 OpenBabel07101719122D 24 26 0 0 0 0 0 0 0 0999 V2000 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 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 -0.0000 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 1.5000 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 -1.7321 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 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 -5.1962 3.0000 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 -3.4641 3.0000 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 11 2 0 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 12 16 2 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	328.501
LogP:	3.105
LogD:	3.071
LogS:	-3.314
# Rotatable Bonds:	4
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.897
Synthetic Accessibility Score:	2.954
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	1.7180220311274752e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	92.98250579833984%
Volume Distribution (VD):	0.783
Pgp-substrate:	11.223992347717285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.851
CYP2C19-substrate:	0.445
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.424
CYP2D6-substrate:	0.777
CYP3A4-inhibitor:	0.65
CYP3A4-substrate:	0.83

ADMET: Excretion

Clearance (CL):	9.452
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.065
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.731
Skin Sensitization:	0.946
Carcinogencity:	0.149
Eye Corrosion:	0.003
Eye Irritation:	0.787
Respiratory Toxicity:	0.573

Download Data

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

Natural Product: NPC229442

Natural Product ID:	NPC229442
*Common Name:**	Lespeflorin E1
IUPAC Name:	3-(4-hydroxy-2,3-dimethoxyphenyl)-8-methoxy-2H-chromen-7-ol
Synonyms:	Lespeflorin E1
Standard InCHIKey:	KQIIEUWMLQSINE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-21-16-12(5-7-14(20)18(16)23-3)11-8-10-4-6-13(19)17(22-2)15(10)24-9-11/h4-8,19-20H,9H2,1-3H3
SMILES:	COc1c(ccc(c1OC)O)C1=Cc2ccc(c(c2OC1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560441
PubChem CID:	25243078
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002603] 8-O-methylated isoflavonoids

*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
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	4290.0	nM	PMID[487748]

☑ 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 NPC229442 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	413
0.1-0.2	1739
0.2-0.3	5607
0.3-0.4	13019
0.4-0.5	4120
0.5-0.6	4070
0.6-0.7	5995
0.7-0.8	5669
0.8-0.85	1118
0.85-0.9	576
0.9-0.95	300
0.95-1	71

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168059
0.9762	High Similarity	NPC91291
0.969	High Similarity	NPC470356
0.969	High Similarity	NPC474206
0.969	High Similarity	NPC112246
0.969	High Similarity	NPC94750
0.969	High Similarity	NPC112939
0.969	High Similarity	NPC121812
0.9615	High Similarity	NPC265433
0.9615	High Similarity	NPC227503
0.9615	High Similarity	NPC270456
0.9615	High Similarity	NPC16435
0.9615	High Similarity	NPC162659
0.9615	High Similarity	NPC248727
0.9615	High Similarity	NPC306441
0.9615	High Similarity	NPC230734
0.9615	High Similarity	NPC474639
0.9612	High Similarity	NPC106215
0.9612	High Similarity	NPC317380
0.9609	High Similarity	NPC202762
0.9609	High Similarity	NPC86655
0.9609	High Similarity	NPC127624
0.9542	High Similarity	NPC276490
0.9542	High Similarity	NPC103976
0.9542	High Similarity	NPC474282
0.9542	High Similarity	NPC326797
0.9542	High Similarity	NPC211549
0.9542	High Similarity	NPC107551
0.9542	High Similarity	NPC176051
0.9542	High Similarity	NPC102904
0.9538	High Similarity	NPC234333
0.9538	High Similarity	NPC472337
0.9538	High Similarity	NPC151224
0.9538	High Similarity	NPC260898
0.9538	High Similarity	NPC61946
0.9538	High Similarity	NPC47398
0.9535	High Similarity	NPC36661
0.9535	High Similarity	NPC11060
0.9535	High Similarity	NPC475840
0.9531	High Similarity	NPC472597
0.9524	High Similarity	NPC210355
0.947	High Similarity	NPC245207
0.947	High Similarity	NPC25966
0.947	High Similarity	NPC70682
0.947	High Similarity	NPC127218
0.947	High Similarity	NPC319647
0.947	High Similarity	NPC260741
0.9466	High Similarity	NPC269091
0.9466	High Similarity	NPC472334
0.9466	High Similarity	NPC302701
0.9466	High Similarity	NPC472336
0.9462	High Similarity	NPC170694
0.9457	High Similarity	NPC16208
0.9457	High Similarity	NPC7903
0.9457	High Similarity	NPC160991
0.9457	High Similarity	NPC184447
0.9457	High Similarity	NPC35932
0.9453	High Similarity	NPC214860
0.9453	High Similarity	NPC472338
0.9444	High Similarity	NPC18924
0.9444	High Similarity	NPC223136
0.9444	High Similarity	NPC28730
0.9444	High Similarity	NPC214406
0.9444	High Similarity	NPC78974
0.9444	High Similarity	NPC103823
0.9444	High Similarity	NPC44748
0.9403	High Similarity	NPC2613
0.9403	High Similarity	NPC204347
0.9403	High Similarity	NPC59841
0.9403	High Similarity	NPC475891
0.9398	High Similarity	NPC184797
0.9398	High Similarity	NPC22317
0.9398	High Similarity	NPC309124
0.9389	High Similarity	NPC195022
0.9389	High Similarity	NPC473413
0.9389	High Similarity	NPC164787
0.9385	High Similarity	NPC263064
0.9375	High Similarity	NPC470258
0.9375	High Similarity	NPC10225
0.9375	High Similarity	NPC218856
0.9375	High Similarity	NPC226788
0.9375	High Similarity	NPC273295
0.9375	High Similarity	NPC285339
0.9375	High Similarity	NPC45824
0.9375	High Similarity	NPC222004
0.9375	High Similarity	NPC190629
0.9375	High Similarity	NPC210623
0.9375	High Similarity	NPC3439
0.9375	High Similarity	NPC202582
0.9375	High Similarity	NPC58164
0.937	High Similarity	NPC82679
0.937	High Similarity	NPC74817
0.937	High Similarity	NPC324112
0.937	High Similarity	NPC236791
0.937	High Similarity	NPC169474
0.937	High Similarity	NPC293054
0.937	High Similarity	NPC246620
0.937	High Similarity	NPC282000
0.937	High Similarity	NPC159968
0.937	High Similarity	NPC124452
0.9365	High Similarity	NPC60885
0.9365	High Similarity	NPC299584
0.9365	High Similarity	NPC82483
0.9365	High Similarity	NPC234400
0.9365	High Similarity	NPC265483
0.9328	High Similarity	NPC35216
0.9328	High Similarity	NPC471389
0.9323	High Similarity	NPC236306
0.9323	High Similarity	NPC232164
0.9323	High Similarity	NPC473739
0.9318	High Similarity	NPC173660
0.9318	High Similarity	NPC470802
0.9318	High Similarity	NPC234952
0.9313	High Similarity	NPC310854
0.9308	High Similarity	NPC219876
0.9308	High Similarity	NPC126029
0.9308	High Similarity	NPC61477
0.9308	High Similarity	NPC201587
0.9308	High Similarity	NPC470752
0.9308	High Similarity	NPC253105
0.9308	High Similarity	NPC185604
0.9308	High Similarity	NPC15658
0.9308	High Similarity	NPC78770
0.9308	High Similarity	NPC261619
0.9302	High Similarity	NPC311680
0.9302	High Similarity	NPC299221
0.9302	High Similarity	NPC234488
0.9302	High Similarity	NPC51840
0.9302	High Similarity	NPC474481
0.9297	High Similarity	NPC226331
0.9297	High Similarity	NPC46274
0.9286	High Similarity	NPC228972
0.9286	High Similarity	NPC122792
0.9259	High Similarity	NPC107161
0.9254	High Similarity	NPC160283
0.9254	High Similarity	NPC254759
0.9254	High Similarity	NPC259519
0.9242	High Similarity	NPC134968
0.9231	High Similarity	NPC268342
0.9231	High Similarity	NPC469613
0.9231	High Similarity	NPC268266
0.9231	High Similarity	NPC309787
0.9231	High Similarity	NPC470095
0.9231	High Similarity	NPC469625
0.9231	High Similarity	NPC42760
0.9231	High Similarity	NPC470096
0.9231	High Similarity	NPC220825
0.9231	High Similarity	NPC30043
0.9225	High Similarity	NPC469951
0.9225	High Similarity	NPC469963
0.9225	High Similarity	NPC170844
0.9225	High Similarity	NPC5851
0.9225	High Similarity	NPC476968
0.9225	High Similarity	NPC86030
0.9225	High Similarity	NPC212015
0.9219	High Similarity	NPC474119
0.9219	High Similarity	NPC118787
0.9219	High Similarity	NPC216836
0.9219	High Similarity	NPC470699
0.9219	High Similarity	NPC147821
0.9219	High Similarity	NPC111247
0.9219	High Similarity	NPC163332
0.9219	High Similarity	NPC5447
0.9219	High Similarity	NPC183181
0.9219	High Similarity	NPC292056
0.9219	High Similarity	NPC319625
0.9219	High Similarity	NPC250432
0.9219	High Similarity	NPC41706
0.9213	High Similarity	NPC298757
0.9213	High Similarity	NPC57490
0.9213	High Similarity	NPC251855
0.9213	High Similarity	NPC116907
0.9213	High Similarity	NPC221077
0.9213	High Similarity	NPC193544
0.9213	High Similarity	NPC472093
0.9213	High Similarity	NPC117214
0.9213	High Similarity	NPC475169
0.9213	High Similarity	NPC208950
0.9213	High Similarity	NPC233410
0.9213	High Similarity	NPC105925
0.9213	High Similarity	NPC203133
0.9213	High Similarity	NPC17943
0.9206	High Similarity	NPC95168
0.9191	High Similarity	NPC81638
0.9185	High Similarity	NPC87725
0.9185	High Similarity	NPC263261
0.9185	High Similarity	NPC247291
0.9179	High Similarity	NPC292882
0.9179	High Similarity	NPC32630
0.9179	High Similarity	NPC22517
0.9179	High Similarity	NPC471388
0.9167	High Similarity	NPC256307
0.9167	High Similarity	NPC66840
0.9167	High Similarity	NPC478085
0.916	High Similarity	NPC6451
0.9154	High Similarity	NPC126836
0.9154	High Similarity	NPC469612
0.9154	High Similarity	NPC220935
0.9154	High Similarity	NPC469614
0.9147	High Similarity	NPC28765

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 NPC229442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	923
0.2-0.3	1940
0.3-0.4	2706
0.4-0.5	1528
0.5-0.6	861
0.6-0.7	648
0.7-0.8	161
0.8-0.85	11
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9308	High Similarity	NPD1612	Clinical (unspecified phase)
0.9308	High Similarity	NPD1613	Approved
0.9297	High Similarity	NPD1529	Clinical (unspecified phase)
0.9225	High Similarity	NPD3027	Phase 3
0.9219	High Similarity	NPD1530	Clinical (unspecified phase)
0.873	High Similarity	NPD1548	Phase 1
0.8571	High Similarity	NPD4908	Phase 1
0.8503	High Similarity	NPD2801	Approved
0.8462	Intermediate Similarity	NPD1610	Phase 2
0.8444	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1934	Approved
0.8358	Intermediate Similarity	NPD3018	Phase 2
0.8288	Intermediate Similarity	NPD1653	Approved
0.8264	Intermediate Similarity	NPD1511	Approved
0.8255	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD2983	Phase 2
0.8195	Intermediate Similarity	NPD2982	Phase 2
0.8175	Intermediate Similarity	NPD228	Approved
0.8151	Intermediate Similarity	NPD1512	Approved
0.8146	Intermediate Similarity	NPD3882	Suspended
0.812	Intermediate Similarity	NPD2981	Phase 2
0.8102	Intermediate Similarity	NPD4625	Phase 3
0.8088	Intermediate Similarity	NPD2861	Phase 2
0.8079	Intermediate Similarity	NPD3817	Phase 2
0.806	Intermediate Similarity	NPD4749	Approved
0.8026	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6166	Phase 2
0.8013	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7054	Approved
0.7929	Intermediate Similarity	NPD1558	Phase 1
0.7926	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7472	Approved
0.7914	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3818	Discontinued
0.791	Intermediate Similarity	NPD422	Phase 1
0.7907	Intermediate Similarity	NPD5283	Phase 1
0.7815	Intermediate Similarity	NPD4675	Approved
0.7815	Intermediate Similarity	NPD4678	Approved
0.7812	Intermediate Similarity	NPD7074	Phase 3
0.7806	Intermediate Similarity	NPD6234	Discontinued
0.7801	Intermediate Similarity	NPD4060	Phase 1
0.7778	Intermediate Similarity	NPD1091	Approved
0.7764	Intermediate Similarity	NPD6797	Phase 2
0.774	Intermediate Similarity	NPD1652	Phase 2
0.774	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3540	Phase 1
0.7718	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7447	Phase 1
0.7716	Intermediate Similarity	NPD7251	Discontinued
0.7707	Intermediate Similarity	NPD7199	Phase 2
0.7669	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7808	Phase 3
0.7656	Intermediate Similarity	NPD2684	Approved
0.7655	Intermediate Similarity	NPD3539	Phase 1
0.7652	Intermediate Similarity	NPD6671	Approved
0.7651	Intermediate Similarity	NPD7213	Phase 3
0.7651	Intermediate Similarity	NPD7212	Phase 2
0.7647	Intermediate Similarity	NPD3705	Approved
0.7635	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6674	Discontinued
0.761	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD8651	Approved
0.7603	Intermediate Similarity	NPD7266	Discontinued
0.7597	Intermediate Similarity	NPD3021	Approved
0.7597	Intermediate Similarity	NPD37	Approved
0.7597	Intermediate Similarity	NPD3022	Approved
0.7582	Intermediate Similarity	NPD4380	Phase 2
0.7578	Intermediate Similarity	NPD290	Approved
0.7564	Intermediate Similarity	NPD4967	Phase 2
0.7564	Intermediate Similarity	NPD4965	Approved
0.7564	Intermediate Similarity	NPD4966	Approved
0.7557	Intermediate Similarity	NPD7843	Approved
0.7552	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3620	Phase 2
0.755	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1465	Phase 2
0.7531	Intermediate Similarity	NPD5844	Phase 1
0.7519	Intermediate Similarity	NPD7157	Approved
0.7517	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4538	Approved
0.7517	Intermediate Similarity	NPD4536	Approved
0.7516	Intermediate Similarity	NPD4005	Discontinued
0.7516	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6584	Phase 3
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4123	Phase 3
0.7483	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7228	Approved
0.7466	Intermediate Similarity	NPD1510	Phase 2
0.7455	Intermediate Similarity	NPD7549	Discontinued
0.745	Intermediate Similarity	NPD3750	Approved
0.7439	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6232	Discontinued
0.7432	Intermediate Similarity	NPD1549	Phase 2
0.7421	Intermediate Similarity	NPD5494	Approved
0.7417	Intermediate Similarity	NPD4357	Discontinued
0.7417	Intermediate Similarity	NPD6799	Approved
0.7415	Intermediate Similarity	NPD2796	Approved
0.7415	Intermediate Similarity	NPD6100	Approved
0.7415	Intermediate Similarity	NPD6099	Approved
0.7413	Intermediate Similarity	NPD6798	Discontinued
0.741	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5536	Phase 2
0.7405	Intermediate Similarity	NPD7075	Discontinued
0.7405	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2677	Approved
0.7394	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5402	Approved
0.7383	Intermediate Similarity	NPD3060	Approved
0.7383	Intermediate Similarity	NPD5177	Phase 3
0.7381	Intermediate Similarity	NPD1242	Phase 1
0.7379	Intermediate Similarity	NPD4340	Discontinued
0.7379	Intermediate Similarity	NPD230	Phase 1
0.7372	Intermediate Similarity	NPD6516	Phase 2
0.7372	Intermediate Similarity	NPD5846	Approved
0.7365	Intermediate Similarity	NPD8054	Approved
0.7365	Intermediate Similarity	NPD8053	Approved
0.7361	Intermediate Similarity	NPD6233	Phase 2
0.7347	Intermediate Similarity	NPD5588	Approved
0.7347	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5960	Phase 3
0.7347	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7095	Approved
0.7333	Intermediate Similarity	NPD6331	Phase 2
0.7333	Intermediate Similarity	NPD3892	Phase 2
0.7325	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD940	Approved
0.7323	Intermediate Similarity	NPD846	Approved
0.7319	Intermediate Similarity	NPD3496	Discontinued
0.7303	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7473	Discontinued
0.7299	Intermediate Similarity	NPD1357	Approved
0.7286	Intermediate Similarity	NPD6583	Phase 3
0.7286	Intermediate Similarity	NPD6582	Phase 2
0.7285	Intermediate Similarity	NPD2219	Phase 1
0.7285	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD4162	Approved
0.7267	Intermediate Similarity	NPD4237	Approved
0.7267	Intermediate Similarity	NPD4236	Phase 3
0.7261	Intermediate Similarity	NPD6801	Discontinued
0.726	Intermediate Similarity	NPD6355	Discontinued
0.7255	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1375	Discontinued
0.7241	Intermediate Similarity	NPD2674	Phase 3
0.7237	Intermediate Similarity	NPD7124	Phase 2
0.7237	Intermediate Similarity	NPD5058	Phase 3
0.7234	Intermediate Similarity	NPD3225	Approved
0.723	Intermediate Similarity	NPD7033	Discontinued
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7819	Suspended
0.7212	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4750	Phase 3
0.7192	Intermediate Similarity	NPD1240	Approved
0.719	Intermediate Similarity	NPD1774	Approved
0.7188	Intermediate Similarity	NPD291	Approved
0.7186	Intermediate Similarity	NPD6559	Discontinued
0.7183	Intermediate Similarity	NPD2797	Approved
0.7181	Intermediate Similarity	NPD1551	Phase 2
0.717	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5535	Approved
0.7161	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6599	Discontinued
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD5763	Approved
0.7125	Intermediate Similarity	NPD7768	Phase 2
0.7123	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1778	Approved
0.7117	Intermediate Similarity	NPD3787	Discontinued
0.7115	Intermediate Similarity	NPD3687	Approved
0.7115	Intermediate Similarity	NPD3686	Approved
0.7114	Intermediate Similarity	NPD3748	Approved
0.7113	Intermediate Similarity	NPD2922	Phase 1
0.7113	Intermediate Similarity	NPD6696	Suspended
0.7107	Intermediate Similarity	NPD2977	Approved
0.7107	Intermediate Similarity	NPD2978	Approved
0.7105	Intermediate Similarity	NPD4628	Phase 3
0.7105	Intermediate Similarity	NPD4110	Phase 3
0.7105	Intermediate Similarity	NPD7466	Approved
0.7105	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1607	Approved
0.7092	Intermediate Similarity	NPD2235	Phase 2
0.7092	Intermediate Similarity	NPD2231	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