NPASS Compound

Structure

NPC245207 OpenBabel07101719402D 26 28 0 0 1 0 0 0 0 0999 V2000 -1.7321 5.0000 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 2.5981 -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 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 -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 -0.8660 0.5000 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 2 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 3.5000 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 -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 3.0000 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 -4.3301 1.5000 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 26 1 0 0 0 0 10 16 2 0 0 0 0 11 12 1 6 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.14
Volume:	357.224
LogP:	2.671
LogD:	2.935
LogS:	-3.632
# Rotatable Bonds:	5
TPSA:	86.61
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.846
Synthetic Accessibility Score:	3.212
Fsp3:	0.368
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:	-4.883
MDCK Permeability:	1.8586044461699203e-05
Pgp-inhibitor:	0.181
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	87.73686218261719%
Volume Distribution (VD):	0.399
Pgp-substrate:	20.49889373779297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.501
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.45
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.284
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.171
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.658
CYP3A4-substrate:	0.844

ADMET: Excretion

Clearance (CL):	8.485
Half-life (T1/2):	0.65

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.625
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.945
Carcinogencity:	0.171
Eye Corrosion:	0.003
Eye Irritation:	0.738
Respiratory Toxicity:	0.492

Download Data

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

Natural Product: NPC245207

Natural Product ID:	NPC245207
*Common Name:**	(3S)-3',7-Dihydroxy-2',4',5', 8-Tetramethoxyisoflavan
IUPAC Name:	(3S)-3-(3-hydroxy-2,4,5-trimethoxyphenyl)-8-methoxy-3,4-dihydro-2H-chromen-7-ol
Synonyms:
Standard InCHIKey:	WLBRDEZXTKMHFM-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C19H22O7/c1-22-14-8-12(17(23-2)15(21)19(14)25-4)11-7-10-5-6-13(20)18(24-3)16(10)26-9-11/h5-6,8,11,20-21H,7,9H2,1-4H3/t11-/m1/s1
SMILES:	COc1cc([C@H]2COc3c(C2)ccc(c3OC)O)c(c(c1OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478173
PubChem CID:	471695
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO10426	Eysenhardtia polystachya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644061]
NPO10426	Eysenhardtia polystachya	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
ED50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.0	ug ml-1	PMID[575627]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	LC50	>	1000.0	ng/cm2	PMID[575627]

☑ 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 NPC245207 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	445
0.1-0.2	1684
0.2-0.3	4825
0.3-0.4	12812
0.4-0.5	5044
0.5-0.6	4013
0.6-0.7	6309
0.7-0.8	5547
0.8-0.85	1080
0.85-0.9	581
0.9-0.95	298
0.95-1	59

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC319647
1.0	High Similarity	NPC127218
1.0	High Similarity	NPC25966
0.9924	High Similarity	NPC276490
0.985	High Similarity	NPC471389
0.9847	High Similarity	NPC173660
0.9847	High Similarity	NPC265433
0.9847	High Similarity	NPC162659
0.9847	High Similarity	NPC248727
0.9847	High Similarity	NPC270456
0.9776	High Similarity	NPC107161
0.9774	High Similarity	NPC259519
0.9773	High Similarity	NPC107551
0.9773	High Similarity	NPC103976
0.9773	High Similarity	NPC326797
0.9773	High Similarity	NPC474282
0.9773	High Similarity	NPC176051
0.9773	High Similarity	NPC102904
0.9771	High Similarity	NPC195022
0.9701	High Similarity	NPC247291
0.9699	High Similarity	NPC70682
0.9699	High Similarity	NPC471388
0.9699	High Similarity	NPC260741
0.9695	High Similarity	NPC317380
0.9632	High Similarity	NPC280092
0.9632	High Similarity	NPC12641
0.9632	High Similarity	NPC45257
0.9632	High Similarity	NPC93323
0.9627	High Similarity	NPC254759
0.9627	High Similarity	NPC160283
0.9627	High Similarity	NPC27495
0.9627	High Similarity	NPC309124
0.9627	High Similarity	NPC184797
0.9621	High Similarity	NPC112939
0.9621	High Similarity	NPC474206
0.9621	High Similarity	NPC112246
0.9621	High Similarity	NPC121812
0.9621	High Similarity	NPC470356
0.9621	High Similarity	NPC94750
0.9559	High Similarity	NPC85264
0.9559	High Similarity	NPC102044
0.9559	High Similarity	NPC47633
0.9556	High Similarity	NPC35216
0.9552	High Similarity	NPC236306
0.9552	High Similarity	NPC473739
0.9552	High Similarity	NPC292882
0.9552	High Similarity	NPC232164
0.9549	High Similarity	NPC306441
0.9549	High Similarity	NPC472334
0.9549	High Similarity	NPC474639
0.9549	High Similarity	NPC472336
0.9549	High Similarity	NPC16435
0.9549	High Similarity	NPC227503
0.9549	High Similarity	NPC230734
0.9545	High Similarity	NPC106215
0.9542	High Similarity	NPC202762
0.9542	High Similarity	NPC86655
0.9542	High Similarity	NPC127624
0.9542	High Similarity	NPC6451
0.9489	High Similarity	NPC50250
0.9489	High Similarity	NPC63879
0.9485	High Similarity	NPC204347
0.9485	High Similarity	NPC475891
0.9485	High Similarity	NPC2613
0.9485	High Similarity	NPC59841
0.9478	High Similarity	NPC211549
0.9474	High Similarity	NPC151224
0.9474	High Similarity	NPC47398
0.9474	High Similarity	NPC61946
0.9474	High Similarity	NPC260898
0.9474	High Similarity	NPC472337
0.9474	High Similarity	NPC234333
0.947	High Similarity	NPC229442
0.947	High Similarity	NPC168059
0.947	High Similarity	NPC11060
0.9466	High Similarity	NPC474356
0.9466	High Similarity	NPC232275
0.9466	High Similarity	NPC45715
0.9466	High Similarity	NPC12275
0.9424	High Similarity	NPC21776
0.9424	High Similarity	NPC16269
0.942	High Similarity	NPC307466
0.9416	High Similarity	NPC477616
0.9412	High Similarity	NPC311530
0.9403	High Similarity	NPC234952
0.9403	High Similarity	NPC302701
0.9403	High Similarity	NPC269091
0.9398	High Similarity	NPC478085
0.9389	High Similarity	NPC234488
0.9389	High Similarity	NPC299221
0.9389	High Similarity	NPC224157
0.9389	High Similarity	NPC192687
0.9389	High Similarity	NPC311680
0.9389	High Similarity	NPC51840
0.9389	High Similarity	NPC214860
0.9348	High Similarity	NPC473108
0.9328	High Similarity	NPC134968
0.9328	High Similarity	NPC473413
0.9328	High Similarity	NPC164787
0.9323	High Similarity	NPC263064
0.9323	High Similarity	NPC475840
0.9313	High Similarity	NPC58164
0.9313	High Similarity	NPC190144
0.9313	High Similarity	NPC10225
0.9313	High Similarity	NPC45824
0.9286	High Similarity	NPC101376
0.927	High Similarity	NPC87725
0.927	High Similarity	NPC178054
0.927	High Similarity	NPC263261
0.9265	High Similarity	NPC32630
0.9259	High Similarity	NPC470802
0.9254	High Similarity	NPC310854
0.9254	High Similarity	NPC474478
0.9254	High Similarity	NPC170694
0.9248	High Similarity	NPC219876
0.9248	High Similarity	NPC126029
0.9248	High Similarity	NPC15658
0.9248	High Similarity	NPC185604
0.9248	High Similarity	NPC253105
0.9248	High Similarity	NPC78770
0.9248	High Similarity	NPC61477
0.9248	High Similarity	NPC261619
0.9248	High Similarity	NPC201587
0.9242	High Similarity	NPC220935
0.9242	High Similarity	NPC91291
0.9237	High Similarity	NPC226331
0.9237	High Similarity	NPC46274
0.9237	High Similarity	NPC266691
0.922	High Similarity	NPC301961
0.922	High Similarity	NPC175976
0.922	High Similarity	NPC166584
0.9214	High Similarity	NPC211758
0.9214	High Similarity	NPC112251
0.9214	High Similarity	NPC87794
0.9197	High Similarity	NPC22317
0.9197	High Similarity	NPC266197
0.9197	High Similarity	NPC291101
0.9191	High Similarity	NPC25111
0.9191	High Similarity	NPC272157
0.9191	High Similarity	NPC6262
0.9191	High Similarity	NPC90615
0.9191	High Similarity	NPC73535
0.9191	High Similarity	NPC201145
0.9185	High Similarity	NPC201357
0.9185	High Similarity	NPC281521
0.9185	High Similarity	NPC255147
0.9179	High Similarity	NPC158331
0.9173	High Similarity	NPC268266
0.9173	High Similarity	NPC472597
0.9173	High Similarity	NPC220825
0.9173	High Similarity	NPC268342
0.9173	High Similarity	NPC474017
0.9173	High Similarity	NPC42760
0.916	High Similarity	NPC124452
0.916	High Similarity	NPC250432
0.916	High Similarity	NPC82679
0.916	High Similarity	NPC127587
0.916	High Similarity	NPC216836
0.916	High Similarity	NPC5447
0.916	High Similarity	NPC236791
0.916	High Similarity	NPC210355
0.916	High Similarity	NPC324112
0.916	High Similarity	NPC74817
0.916	High Similarity	NPC169474
0.916	High Similarity	NPC293054
0.916	High Similarity	NPC246620
0.916	High Similarity	NPC159968
0.916	High Similarity	NPC282000
0.9155	High Similarity	NPC476969
0.9149	High Similarity	NPC227902
0.9137	High Similarity	NPC81638
0.913	High Similarity	NPC265075
0.9124	High Similarity	NPC184613
0.9124	High Similarity	NPC22517
0.9124	High Similarity	NPC19869
0.9124	High Similarity	NPC29868
0.9124	High Similarity	NPC79622
0.9124	High Similarity	NPC212942
0.9118	High Similarity	NPC476639
0.9118	High Similarity	NPC114155
0.9118	High Similarity	NPC300846
0.9111	High Similarity	NPC287745
0.9104	High Similarity	NPC35932
0.9104	High Similarity	NPC204215
0.9104	High Similarity	NPC175067
0.9104	High Similarity	NPC160991
0.9104	High Similarity	NPC16208
0.9104	High Similarity	NPC470752
0.9104	High Similarity	NPC7903
0.9104	High Similarity	NPC184447
0.9098	High Similarity	NPC126836
0.9098	High Similarity	NPC472338
0.9097	High Similarity	NPC160196
0.9091	High Similarity	NPC31707
0.9091	High Similarity	NPC154866
0.9085	High Similarity	NPC281549
0.9084	High Similarity	NPC214406
0.9084	High Similarity	NPC26879
0.9084	High Similarity	NPC44748
0.9084	High Similarity	NPC76451

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 NPC245207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	912
0.2-0.3	1888
0.3-0.4	2726
0.4-0.5	1565
0.5-0.6	856
0.6-0.7	646
0.7-0.8	150
0.8-0.85	10
0.85-0.9	3
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9248	High Similarity	NPD1613	Approved
0.9248	High Similarity	NPD1612	Clinical (unspecified phase)
0.9237	High Similarity	NPD1529	Clinical (unspecified phase)
0.916	High Similarity	NPD1530	Clinical (unspecified phase)
0.9023	High Similarity	NPD3027	Phase 3
0.8806	High Similarity	NPD4908	Phase 1
0.8702	High Similarity	NPD1610	Phase 2
0.8676	High Similarity	NPD4907	Clinical (unspecified phase)
0.8593	High Similarity	NPD2861	Phase 2
0.84	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD2801	Approved
0.8296	Intermediate Similarity	NPD4749	Approved
0.8258	Intermediate Similarity	NPD1548	Phase 1
0.8255	Intermediate Similarity	NPD1653	Approved
0.8224	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD4625	Phase 3
0.8143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD3018	Phase 2
0.8015	Intermediate Similarity	NPD5283	Phase 1
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6166	Phase 2
0.7987	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD4060	Phase 1
0.7899	Intermediate Similarity	NPD2982	Phase 2
0.7899	Intermediate Similarity	NPD2983	Phase 2
0.7898	Intermediate Similarity	NPD6234	Discontinued
0.7895	Intermediate Similarity	NPD6671	Approved
0.7885	Intermediate Similarity	NPD3882	Suspended
0.7867	Intermediate Similarity	NPD1511	Approved
0.7863	Intermediate Similarity	NPD228	Approved
0.7848	Intermediate Similarity	NPD5494	Approved
0.784	Intermediate Similarity	NPD5844	Phase 1
0.7838	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6674	Discontinued
0.7826	Intermediate Similarity	NPD2981	Phase 2
0.7799	Intermediate Similarity	NPD7199	Phase 2
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7763	Intermediate Similarity	NPD1512	Approved
0.7758	Intermediate Similarity	NPD7549	Discontinued
0.773	Intermediate Similarity	NPD7054	Approved
0.771	Intermediate Similarity	NPD3022	Approved
0.771	Intermediate Similarity	NPD3021	Approved
0.7707	Intermediate Similarity	NPD3817	Phase 2
0.7702	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD37	Approved
0.7683	Intermediate Similarity	NPD7472	Approved
0.7669	Intermediate Similarity	NPD3818	Discontinued
0.7669	Intermediate Similarity	NPD7228	Approved
0.7658	Intermediate Similarity	NPD4965	Approved
0.7658	Intermediate Similarity	NPD4967	Phase 2
0.7658	Intermediate Similarity	NPD4966	Approved
0.7655	Intermediate Similarity	NPD1558	Phase 1
0.7655	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3620	Phase 2
0.7651	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1465	Phase 2
0.7639	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6100	Approved
0.7635	Intermediate Similarity	NPD6099	Approved
0.7626	Intermediate Similarity	NPD1091	Approved
0.7616	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD8651	Approved
0.7584	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7447	Phase 1
0.7568	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4675	Approved
0.7564	Intermediate Similarity	NPD4678	Approved
0.753	Intermediate Similarity	NPD6797	Phase 2
0.7518	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7213	Phase 3
0.7516	Intermediate Similarity	NPD7212	Phase 2
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD4536	Approved
0.75	Intermediate Similarity	NPD4538	Approved
0.75	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7483	Intermediate Similarity	NPD5124	Phase 1
0.7483	Intermediate Similarity	NPD1652	Phase 2
0.7483	Intermediate Similarity	NPD5177	Phase 3
0.7483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD968	Approved
0.7468	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3540	Phase 1
0.7467	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7266	Discontinued
0.7467	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8054	Approved
0.7456	Intermediate Similarity	NPD8053	Approved
0.7452	Intermediate Similarity	NPD4380	Phase 2
0.744	Intermediate Similarity	NPD7808	Phase 3
0.7434	Intermediate Similarity	NPD3892	Phase 2
0.7434	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6232	Discontinued
0.7417	Intermediate Similarity	NPD1549	Phase 2
0.7407	Intermediate Similarity	NPD7843	Approved
0.74	Intermediate Similarity	NPD3539	Phase 1
0.7394	Intermediate Similarity	NPD7473	Discontinued
0.7391	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7075	Discontinued
0.7391	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4005	Discontinued
0.7375	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6355	Discontinued
0.7361	Intermediate Similarity	NPD6584	Phase 3
0.7355	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6233	Phase 2
0.7343	Intermediate Similarity	NPD6696	Suspended
0.7338	Intermediate Similarity	NPD7124	Phase 2
0.7333	Intermediate Similarity	NPD5588	Approved
0.7333	Intermediate Similarity	NPD5960	Phase 3
0.7329	Intermediate Similarity	NPD7095	Approved
0.732	Intermediate Similarity	NPD3750	Approved
0.732	Intermediate Similarity	NPD6331	Phase 2
0.732	Intermediate Similarity	NPD7466	Approved
0.7313	Intermediate Similarity	NPD4750	Phase 3
0.7312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7819	Suspended
0.7305	Intermediate Similarity	NPD3496	Discontinued
0.7296	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD290	Approved
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7278	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2677	Approved
0.7267	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5402	Approved
0.7267	Intermediate Similarity	NPD4663	Approved
0.7248	Intermediate Similarity	NPD5735	Approved
0.7244	Intermediate Similarity	NPD4123	Phase 3
0.7244	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1375	Discontinued
0.7237	Intermediate Similarity	NPD5763	Approved
0.7237	Intermediate Similarity	NPD5762	Approved
0.7234	Intermediate Similarity	NPD6516	Phase 2
0.7234	Intermediate Similarity	NPD5846	Approved
0.7229	Intermediate Similarity	NPD27	Approved
0.7229	Intermediate Similarity	NPD2489	Approved
0.7226	Intermediate Similarity	NPD5058	Phase 3
0.7225	Intermediate Similarity	NPD7906	Approved
0.7219	Intermediate Similarity	NPD1510	Phase 2
0.7212	Intermediate Similarity	NPD3787	Discontinued
0.7209	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4110	Phase 3
0.7208	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5929	Approved
0.7197	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7340	Approved
0.7193	Intermediate Similarity	NPD7311	Approved
0.7193	Intermediate Similarity	NPD7310	Approved
0.7193	Intermediate Similarity	NPD7312	Approved
0.7193	Intermediate Similarity	NPD4577	Approved
0.7193	Intermediate Similarity	NPD7313	Approved
0.7193	Intermediate Similarity	NPD4578	Approved
0.7181	Intermediate Similarity	NPD2238	Phase 2
0.7179	Intermediate Similarity	NPD4357	Discontinued
0.7179	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6799	Approved
0.7176	Intermediate Similarity	NPD940	Approved
0.7176	Intermediate Similarity	NPD7240	Approved
0.7176	Intermediate Similarity	NPD6559	Discontinued
0.7176	Intermediate Similarity	NPD846	Approved
0.7172	Intermediate Similarity	NPD2797	Approved
0.7171	Intermediate Similarity	NPD2935	Discontinued
0.7171	Intermediate Similarity	NPD2796	Approved
0.7169	Intermediate Similarity	NPD2970	Approved
0.7169	Intermediate Similarity	NPD2969	Approved
0.7161	Intermediate Similarity	NPD6190	Approved
0.7153	Intermediate Similarity	NPD6582	Phase 2
0.7153	Intermediate Similarity	NPD6583	Phase 3
0.7152	Intermediate Similarity	NPD6111	Discontinued
0.7152	Intermediate Similarity	NPD6959	Discontinued
0.7151	Intermediate Similarity	NPD7309	Approved
0.7143	Intermediate Similarity	NPD3384	Approved
0.7143	Intermediate Similarity	NPD3382	Approved
0.7143	Intermediate Similarity	NPD3383	Approved
0.7143	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7143	Intermediate Similarity	NPD3060	Approved
0.7133	Intermediate Similarity	NPD230	Phase 1
0.7125	Intermediate Similarity	NPD6599	Discontinued
0.7117	Intermediate Similarity	NPD7768	Phase 2
0.7108	Intermediate Similarity	NPD7229	Phase 3
0.7108	Intermediate Similarity	NPD3051	Approved
0.7101	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1398	Phase 1
0.7101	Intermediate Similarity	NPD8156	Discontinued
0.7099	Intermediate Similarity	NPD1242	Phase 1
0.7097	Intermediate Similarity	NPD4628	Phase 3
0.7089	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1608	Approved
0.7081	Intermediate Similarity	NPD6072	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data