NPASS Compound

Structure

CID259519 OpenBabel06191716062D 26 28 0 0 1 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 -5.0000 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 -2.0000 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 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 -0.0000 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 -2.5981 -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 0.8660 -1.5000 0.0000 C 0 0 1 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 -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 -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 2.5981 -3.5000 0.0000 C 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 12 2 0 0 0 0 5 13 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 8 21 1 0 0 0 0 9 18 2 0 0 0 0 9 19 1 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 26 1 0 0 0 0 13 17 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 1 0 0 0 16 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	371.599
LogP:	4.551
LogD:	3.694
LogS:	-3.806
# Rotatable Bonds:	4
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	3.284
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.917
MDCK Permeability:	1.2057422281941399e-05
Pgp-inhibitor:	0.548
Pgp-substrate:	0.705
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	99.51117706298828%
Volume Distribution (VD):	1.198
Pgp-substrate:	1.6316022872924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.907
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.776
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	16.219
Half-life (T1/2):	0.696

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.611
AMES Toxicity:	0.27
Rat Oral Acute Toxicity:	0.458
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.952
Carcinogencity:	0.156
Eye Corrosion:	0.003
Eye Irritation:	0.904
Respiratory Toxicity:	0.639

Download Data

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

Natural Product: NPC259519

Natural Product ID:	NPC259519
*Common Name:**	Lespecyrtin D1
IUPAC Name:	4-[(3R)-7-hydroxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-6-methoxybenzene-1,3-diol
Synonyms:	Lespecyrtin D1
Standard InCHIKey:	ZEYGPIZPJVPIMO-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-12(2)4-5-13-6-14-7-15(11-26-20(14)10-17(13)22)16-8-21(25-3)19(24)9-18(16)23/h4,6,8-10,15,22-24H,5,7,11H2,1-3H3/t15-/m0/s1
SMILES:	COc1cc([C@@H]2COc3c(C2)cc(c(c3)O)CC=C(C)C)c(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554280
PubChem CID:	25208603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002605] 3'-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
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19102656]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10080	Teucrium betonicum	Species	Lamiaceae	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	=	2100.0	nM	PMID[496918]

☑ 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 NPC259519 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	446
0.1-0.2	1668
0.2-0.3	4563
0.3-0.4	12391
0.4-0.5	5830
0.5-0.6	3944
0.6-0.7	6273
0.7-0.8	5685
0.8-0.85	1041
0.85-0.9	603
0.9-0.95	221
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9778	High Similarity	NPC85264
0.9778	High Similarity	NPC47633
0.9778	High Similarity	NPC102044
0.9774	High Similarity	NPC127218
0.9774	High Similarity	NPC245207
0.9774	High Similarity	NPC25966
0.9774	High Similarity	NPC319647
0.9774	High Similarity	NPC70682
0.9774	High Similarity	NPC260741
0.9706	High Similarity	NPC45257
0.9706	High Similarity	NPC63879
0.9706	High Similarity	NPC12641
0.9706	High Similarity	NPC280092
0.9706	High Similarity	NPC93323
0.9699	High Similarity	NPC276490
0.963	High Similarity	NPC247291
0.963	High Similarity	NPC471389
0.963	High Similarity	NPC35216
0.9624	High Similarity	NPC162659
0.9624	High Similarity	NPC248727
0.9624	High Similarity	NPC173660
0.9624	High Similarity	NPC265433
0.9624	High Similarity	NPC270456
0.9562	High Similarity	NPC50250
0.9559	High Similarity	NPC2613
0.9559	High Similarity	NPC204347
0.9559	High Similarity	NPC475891
0.9559	High Similarity	NPC107161
0.9559	High Similarity	NPC59841
0.9552	High Similarity	NPC176051
0.9552	High Similarity	NPC107551
0.9552	High Similarity	NPC102904
0.9552	High Similarity	NPC103976
0.9552	High Similarity	NPC474282
0.9552	High Similarity	NPC326797
0.9549	High Similarity	NPC195022
0.9496	High Similarity	NPC101376
0.9496	High Similarity	NPC21776
0.9496	High Similarity	NPC16269
0.9481	High Similarity	NPC471388
0.9478	High Similarity	NPC470802
0.9474	High Similarity	NPC317380
0.947	High Similarity	NPC127624
0.942	High Similarity	NPC473108
0.9412	High Similarity	NPC27495
0.9412	High Similarity	NPC184797
0.9412	High Similarity	NPC160283
0.9412	High Similarity	NPC254759
0.9412	High Similarity	NPC309124
0.9403	High Similarity	NPC112246
0.9403	High Similarity	NPC234333
0.9403	High Similarity	NPC47398
0.9403	High Similarity	NPC260898
0.9403	High Similarity	NPC470356
0.9403	High Similarity	NPC474206
0.9403	High Similarity	NPC473413
0.9403	High Similarity	NPC121812
0.9403	High Similarity	NPC112939
0.9403	High Similarity	NPC94750
0.9353	High Similarity	NPC307466
0.9343	High Similarity	NPC311530
0.9343	High Similarity	NPC87725
0.9343	High Similarity	NPC263261
0.9338	High Similarity	NPC32630
0.9338	High Similarity	NPC236306
0.9338	High Similarity	NPC473739
0.9338	High Similarity	NPC292882
0.9338	High Similarity	NPC232164
0.9333	High Similarity	NPC306441
0.9333	High Similarity	NPC16435
0.9333	High Similarity	NPC227503
0.9333	High Similarity	NPC474639
0.9333	High Similarity	NPC230734
0.9333	High Similarity	NPC472336
0.9333	High Similarity	NPC472334
0.9328	High Similarity	NPC106215
0.9323	High Similarity	NPC86655
0.9323	High Similarity	NPC6451
0.9323	High Similarity	NPC202762
0.9318	High Similarity	NPC214860
0.9286	High Similarity	NPC112251
0.9265	High Similarity	NPC211549
0.9259	High Similarity	NPC472337
0.9259	High Similarity	NPC61946
0.9259	High Similarity	NPC151224
0.9254	High Similarity	NPC11060
0.9254	High Similarity	NPC168059
0.9254	High Similarity	NPC229442
0.9248	High Similarity	NPC12275
0.9248	High Similarity	NPC45715
0.9248	High Similarity	NPC232275
0.9248	High Similarity	NPC474356
0.9242	High Similarity	NPC45824
0.9209	High Similarity	NPC477616
0.9203	High Similarity	NPC265075
0.9191	High Similarity	NPC302701
0.9191	High Similarity	NPC234952
0.9191	High Similarity	NPC269091
0.9185	High Similarity	NPC478085
0.9173	High Similarity	NPC51840
0.9173	High Similarity	NPC234488
0.9173	High Similarity	NPC224157
0.9173	High Similarity	NPC192687
0.9173	High Similarity	NPC311680
0.9173	High Similarity	NPC299221
0.9167	High Similarity	NPC28765
0.9167	High Similarity	NPC160196
0.9155	High Similarity	NPC71726
0.9149	High Similarity	NPC233980
0.9149	High Similarity	NPC260397
0.9143	High Similarity	NPC469795
0.913	High Similarity	NPC34431
0.913	High Similarity	NPC165026
0.913	High Similarity	NPC295719
0.913	High Similarity	NPC73505
0.9124	High Similarity	NPC477938
0.9118	High Similarity	NPC256262
0.9118	High Similarity	NPC164787
0.9118	High Similarity	NPC134968
0.9111	High Similarity	NPC475840
0.9111	High Similarity	NPC263064
0.9104	High Similarity	NPC220825
0.9104	High Similarity	NPC268342
0.9104	High Similarity	NPC42760
0.9104	High Similarity	NPC268266
0.9098	High Similarity	NPC58164
0.9098	High Similarity	NPC10225
0.9098	High Similarity	NPC190144
0.9097	High Similarity	NPC2745
0.9091	High Similarity	NPC250432
0.9091	High Similarity	NPC252131
0.9091	High Similarity	NPC211561
0.9091	High Similarity	NPC5447
0.9091	High Similarity	NPC216836
0.9085	High Similarity	NPC474397
0.9078	High Similarity	NPC90645
0.9078	High Similarity	NPC469557
0.9078	High Similarity	NPC472457
0.9065	High Similarity	NPC178054
0.9058	High Similarity	NPC230124
0.9058	High Similarity	NPC19869
0.9058	High Similarity	NPC29868
0.9058	High Similarity	NPC79622
0.9058	High Similarity	NPC6300
0.9058	High Similarity	NPC184613
0.9058	High Similarity	NPC114171
0.9058	High Similarity	NPC212942
0.9051	High Similarity	NPC177160
0.9051	High Similarity	NPC29799
0.9051	High Similarity	NPC209985
0.9051	High Similarity	NPC10737
0.9051	High Similarity	NPC54743
0.9051	High Similarity	NPC263367
0.9051	High Similarity	NPC156502
0.9051	High Similarity	NPC477939
0.9044	High Similarity	NPC310854
0.9044	High Similarity	NPC49603
0.9044	High Similarity	NPC474478
0.9044	High Similarity	NPC170694
0.9044	High Similarity	NPC193026
0.9044	High Similarity	NPC209199
0.9044	High Similarity	NPC187616
0.9041	High Similarity	NPC80918
0.9041	High Similarity	NPC188578
0.9041	High Similarity	NPC159922
0.9037	High Similarity	NPC15658
0.9037	High Similarity	NPC126029
0.9037	High Similarity	NPC78770
0.9037	High Similarity	NPC175067
0.9037	High Similarity	NPC219876
0.9037	High Similarity	NPC253105
0.9037	High Similarity	NPC185604
0.9037	High Similarity	NPC261619
0.9037	High Similarity	NPC204215
0.9037	High Similarity	NPC201587
0.9037	High Similarity	NPC61477
0.9034	High Similarity	NPC157783
0.903	High Similarity	NPC91291
0.903	High Similarity	NPC220935
0.9028	High Similarity	NPC477612
0.9028	High Similarity	NPC472709
0.9028	High Similarity	NPC472710
0.9028	High Similarity	NPC195561
0.9028	High Similarity	NPC158784
0.9023	High Similarity	NPC266691
0.9023	High Similarity	NPC53986
0.9023	High Similarity	NPC226331
0.9023	High Similarity	NPC46274
0.9023	High Similarity	NPC38664
0.9021	High Similarity	NPC175976
0.9021	High Similarity	NPC301961
0.9021	High Similarity	NPC473876
0.9021	High Similarity	NPC166584
0.9015	High Similarity	NPC76451
0.9014	High Similarity	NPC87794
0.9014	High Similarity	NPC226540
0.9014	High Similarity	NPC211758
0.9014	High Similarity	NPC96576
0.9007	High Similarity	NPC473845
0.9	High Similarity	NPC175838

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 NPC259519 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	929
0.2-0.3	1940
0.3-0.4	2733
0.4-0.5	1545
0.5-0.6	832
0.6-0.7	638
0.7-0.8	134
0.8-0.85	10
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD1530	Clinical (unspecified phase)
0.9037	High Similarity	NPD1613	Approved
0.9037	High Similarity	NPD1612	Clinical (unspecified phase)
0.9023	High Similarity	NPD1529	Clinical (unspecified phase)
0.8815	High Similarity	NPD3027	Phase 3
0.875	High Similarity	NPD4907	Clinical (unspecified phase)
0.8603	High Similarity	NPD4908	Phase 1
0.8496	Intermediate Similarity	NPD1610	Phase 2
0.8394	Intermediate Similarity	NPD2861	Phase 2
0.8289	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD4625	Phase 3
0.8235	Intermediate Similarity	NPD4749	Approved
0.8224	Intermediate Similarity	NPD1934	Approved
0.8214	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD2801	Approved
0.8079	Intermediate Similarity	NPD1653	Approved
0.806	Intermediate Similarity	NPD1548	Phase 1
0.8027	Intermediate Similarity	NPD6674	Discontinued
0.7972	Intermediate Similarity	NPD4060	Phase 1
0.7962	Intermediate Similarity	NPD6234	Discontinued
0.7949	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5494	Approved
0.7905	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5844	Phase 1
0.7872	Intermediate Similarity	NPD3018	Phase 2
0.7826	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6166	Phase 2
0.7826	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD5283	Phase 1
0.7756	Intermediate Similarity	NPD37	Approved
0.773	Intermediate Similarity	NPD7228	Approved
0.7724	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3620	Phase 2
0.7722	Intermediate Similarity	NPD4966	Approved
0.7722	Intermediate Similarity	NPD3882	Suspended
0.7722	Intermediate Similarity	NPD4965	Approved
0.7722	Intermediate Similarity	NPD4967	Phase 2
0.7714	Intermediate Similarity	NPD2982	Phase 2
0.7714	Intermediate Similarity	NPD2983	Phase 2
0.7704	Intermediate Similarity	NPD6671	Approved
0.7697	Intermediate Similarity	NPD1511	Approved
0.7676	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD228	Approved
0.766	Intermediate Similarity	NPD8651	Approved
0.7643	Intermediate Similarity	NPD2981	Phase 2
0.764	Intermediate Similarity	NPD7199	Phase 2
0.7636	Intermediate Similarity	NPD7074	Phase 3
0.7605	Intermediate Similarity	NPD7549	Discontinued
0.7597	Intermediate Similarity	NPD1512	Approved
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.7589	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6100	Approved
0.7584	Intermediate Similarity	NPD6099	Approved
0.7576	Intermediate Similarity	NPD7054	Approved
0.7568	Intermediate Similarity	NPD4538	Approved
0.7568	Intermediate Similarity	NPD4536	Approved
0.7568	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5124	Phase 1
0.7547	Intermediate Similarity	NPD3817	Phase 2
0.7546	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6696	Suspended
0.7532	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7472	Approved
0.7519	Intermediate Similarity	NPD3022	Approved
0.7519	Intermediate Similarity	NPD3021	Approved
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6232	Discontinued
0.7484	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1558	Phase 1
0.7466	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7473	Discontinued
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7451	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1091	Approved
0.7447	Intermediate Similarity	NPD3705	Approved
0.7438	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7447	Phase 1
0.7417	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4675	Approved
0.7405	Intermediate Similarity	NPD4678	Approved
0.74	Intermediate Similarity	NPD5588	Approved
0.74	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5960	Phase 3
0.74	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7340	Approved
0.7386	Intermediate Similarity	NPD6331	Phase 2
0.7381	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7375	Intermediate Similarity	NPD7819	Suspended
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7213	Phase 3
0.7355	Intermediate Similarity	NPD7212	Phase 2
0.7342	Intermediate Similarity	NPD4005	Discontinued
0.7337	Intermediate Similarity	NPD7251	Discontinued
0.7324	Intermediate Similarity	NPD422	Phase 1
0.732	Intermediate Similarity	NPD1652	Phase 2
0.732	Intermediate Similarity	NPD5177	Phase 3
0.7319	Intermediate Similarity	NPD7157	Approved
0.7317	Intermediate Similarity	NPD6959	Discontinued
0.7313	Intermediate Similarity	NPD2684	Approved
0.731	Intermediate Similarity	NPD8054	Approved
0.731	Intermediate Similarity	NPD8053	Approved
0.7303	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7266	Discontinued
0.7303	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3540	Phase 1
0.7299	Intermediate Similarity	NPD1398	Phase 1
0.7294	Intermediate Similarity	NPD7808	Phase 3
0.7293	Intermediate Similarity	NPD968	Approved
0.729	Intermediate Similarity	NPD5058	Phase 3
0.7273	Intermediate Similarity	NPD3892	Phase 2
0.7267	Intermediate Similarity	NPD5929	Approved
0.7261	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4750	Phase 3
0.7255	Intermediate Similarity	NPD1549	Phase 2
0.7239	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3539	Phase 1
0.7237	Intermediate Similarity	NPD2935	Discontinued
0.7235	Intermediate Similarity	NPD6559	Discontinued
0.7235	Intermediate Similarity	NPD7240	Approved
0.7233	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7843	Approved
0.7225	Intermediate Similarity	NPD4663	Approved
0.7222	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD5735	Approved
0.7197	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6584	Phase 3
0.719	Intermediate Similarity	NPD5763	Approved
0.719	Intermediate Similarity	NPD5762	Approved
0.7186	Intermediate Similarity	NPD2489	Approved
0.7186	Intermediate Similarity	NPD27	Approved
0.7184	Intermediate Similarity	NPD7906	Approved
0.7181	Intermediate Similarity	NPD6233	Phase 2
0.7179	Intermediate Similarity	NPD7124	Phase 2
0.7178	Intermediate Similarity	NPD7768	Phase 2
0.7169	Intermediate Similarity	NPD7229	Phase 3
0.7168	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7095	Approved
0.7161	Intermediate Similarity	NPD7466	Approved
0.7161	Intermediate Similarity	NPD3750	Approved
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4577	Approved
0.7151	Intermediate Similarity	NPD7313	Approved
0.7151	Intermediate Similarity	NPD7310	Approved
0.7151	Intermediate Similarity	NPD7312	Approved
0.7151	Intermediate Similarity	NPD4578	Approved
0.7151	Intermediate Similarity	NPD7311	Approved
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7143	Intermediate Similarity	NPD6072	Discontinued
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7133	Intermediate Similarity	NPD3496	Discontinued
0.7126	Intermediate Similarity	NPD2969	Approved
0.7126	Intermediate Similarity	NPD2970	Approved
0.7117	Intermediate Similarity	NPD5402	Approved
0.7115	Intermediate Similarity	NPD2677	Approved
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7111	Intermediate Similarity	NPD290	Approved
0.711	Intermediate Similarity	NPD7309	Approved
0.711	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1247	Approved
0.7105	Intermediate Similarity	NPD6111	Discontinued
0.7099	Intermediate Similarity	NPD6801	Discontinued
0.7089	Intermediate Similarity	NPD4123	Phase 3
0.7089	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD230	Phase 1
0.7083	Intermediate Similarity	NPD1611	Approved
0.7078	Intermediate Similarity	NPD1375	Discontinued
0.7066	Intermediate Similarity	NPD3787	Discontinued
0.7066	Intermediate Similarity	NPD3051	Approved
0.7063	Intermediate Similarity	NPD5846	Approved
0.7063	Intermediate Similarity	NPD6516	Phase 2
0.7059	Intermediate Similarity	NPD1510	Phase 2
0.7055	Intermediate Similarity	NPD8455	Phase 2
0.7051	Intermediate Similarity	NPD4535	Phase 3
0.7051	Intermediate Similarity	NPD4110	Phase 3
0.7051	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6090	Discontinued
0.7039	Intermediate Similarity	NPD4097	Suspended
0.7032	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6799	Approved
0.7025	Intermediate Similarity	NPD7041	Phase 2
0.7025	Intermediate Similarity	NPD4357	Discontinued
0.7025	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2238	Phase 2
0.7013	Intermediate Similarity	NPD2796	Approved
0.7007	Intermediate Similarity	NPD2797	Approved
0.7006	Intermediate Similarity	NPD2219	Phase 1
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD7985	Registered

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