NPASS Compound

Structure

NPC222039 OpenBabel07101718312D 46 49 0 0 0 0 0 0 0 0999 V2000 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 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 -5.1962 -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 -0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 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 -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 -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 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 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 -6.0622 -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 -2.5981 -4.5000 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 -1.7321 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -10.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -5.0000 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 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 1 45 1 0 0 0 0 2 46 1 0 0 0 0 3 9 1 0 0 0 0 3 23 2 0 0 0 0 4 10 2 0 0 0 0 4 23 1 0 0 0 0 5 11 1 0 0 0 0 5 24 2 0 0 0 0 6 12 2 0 0 0 0 6 24 1 0 0 0 0 7 13 2 0 0 0 0 7 25 1 0 0 0 0 8 14 2 0 0 0 0 8 26 1 0 0 0 0 9 27 2 0 0 0 0 10 27 1 0 0 0 0 11 28 2 0 0 0 0 12 28 1 0 0 0 0 13 31 1 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 37 1 0 0 0 0 18 38 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 26 1 0 0 0 0 20 30 2 0 0 0 0 21 25 2 0 0 0 0 21 33 1 0 0 0 0 22 26 2 0 0 0 0 22 34 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 30 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 33 2 0 0 0 0 31 41 1 0 0 0 0 32 34 2 0 0 0 0 32 42 1 0 0 0 0 33 45 1 0 0 0 0 34 46 1 0 0 0 0 35 37 2 3 0 0 0 35 43 1 0 0 0 0 36 38 2 3 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.25
Volume:	647.118
LogP:	3.319
LogD:	4.026
LogS:	-4.245
# Rotatable Bonds:	15
TPSA:	158.24
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.147
Synthetic Accessibility Score:	4.018
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.082
MDCK Permeability:	1.4726009794685524e-05
Pgp-inhibitor:	0.731
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	98.37328338623047%
Volume Distribution (VD):	0.414
Pgp-substrate:	1.1452997922897339%

ADMET: Metabolism

CYP1A2-inhibitor:	0.289
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.601
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.822
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.913
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	14.223
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.764
AMES Toxicity:	0.438
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.481
Skin Sensitization:	0.816
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.159
Respiratory Toxicity:	0.222

Download Data

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

Natural Product: NPC222039

Natural Product ID:	NPC222039
*Common Name:**	Hyoscyamide
IUPAC Name:	(2Z,3Z)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-N,N'-bis[2-(4-hydroxyphenyl)ethyl]butanediamide
Synonyms:	Hyoscyamide
Standard InCHIKey:	FGAVHWSCPSBSMG-NAZWXXJZSA-N
Standard InCHI:	InChI=1S/C36H36N2O8/c1-45-33-21-25(7-13-31(33)41)19-29(35(43)37-17-15-23-3-9-27(39)10-4-23)30(20-26-8-14-32(42)34(22-26)46-2)36(44)38-18-16-24-5-11-28(40)12-6-24/h3-14,19-22,39-42H,15-18H2,1-2H3,(H,37,43)(H,38,44)/b29-19-,30-20-
SMILES:	COc1cc(ccc1O)/C=C(/C(=C/c1ccc(c(c1)OC)O)/C(=NCCc1ccc(cc1)O)O)C(=NCCc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448491
PubChem CID:	5323554
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11858758]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18781	Hyoscyamus niger	Species	Solanaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	100000.0	nM	PMID[481480]

☑ 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 NPC222039 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	219
0.1-0.2	1454
0.2-0.3	7672
0.3-0.4	11010
0.4-0.5	5510
0.5-0.6	9676
0.6-0.7	5611
0.7-0.8	1472
0.8-0.85	43
0.85-0.9	23
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100478
0.9214	High Similarity	NPC5462
0.9041	High Similarity	NPC107602
0.903	High Similarity	NPC52029
0.903	High Similarity	NPC35961
0.903	High Similarity	NPC195749
0.8963	High Similarity	NPC114102
0.8955	High Similarity	NPC155838
0.8897	High Similarity	NPC214869
0.8881	High Similarity	NPC186898
0.8881	High Similarity	NPC251571
0.8836	High Similarity	NPC127402
0.8742	High Similarity	NPC179250
0.8742	High Similarity	NPC50380
0.8693	High Similarity	NPC90984
0.863	High Similarity	NPC470935
0.863	High Similarity	NPC471032
0.8603	High Similarity	NPC153990
0.8582	High Similarity	NPC204848
0.8582	High Similarity	NPC160607
0.8582	High Similarity	NPC312770
0.8582	High Similarity	NPC14600
0.8582	High Similarity	NPC41473
0.8529	High Similarity	NPC301713
0.8521	High Similarity	NPC296898
0.8521	High Similarity	NPC299583
0.8429	Intermediate Similarity	NPC285078
0.8429	Intermediate Similarity	NPC313737
0.8429	Intermediate Similarity	NPC6854
0.8357	Intermediate Similarity	NPC130595
0.8357	Intermediate Similarity	NPC93882
0.8333	Intermediate Similarity	NPC52475
0.8333	Intermediate Similarity	NPC477838
0.8333	Intermediate Similarity	NPC477837
0.8311	Intermediate Similarity	NPC115144
0.8311	Intermediate Similarity	NPC277857
0.8286	Intermediate Similarity	NPC308885
0.8286	Intermediate Similarity	NPC255550
0.8278	Intermediate Similarity	NPC18614
0.8278	Intermediate Similarity	NPC275027
0.8261	Intermediate Similarity	NPC304630
0.8261	Intermediate Similarity	NPC17837
0.8239	Intermediate Similarity	NPC218530
0.8134	Intermediate Similarity	NPC122009
0.8074	Intermediate Similarity	NPC43275
0.8074	Intermediate Similarity	NPC268572
0.8069	Intermediate Similarity	NPC254610
0.806	Intermediate Similarity	NPC283468
0.8027	Intermediate Similarity	NPC110699
0.8027	Intermediate Similarity	NPC106055
0.8013	Intermediate Similarity	NPC153644
0.8	Intermediate Similarity	NPC470626
0.8	Intermediate Similarity	NPC134431
0.8	Intermediate Similarity	NPC156854
0.7973	Intermediate Similarity	NPC470372
0.7961	Intermediate Similarity	NPC182119
0.7958	Intermediate Similarity	NPC210655
0.7956	Intermediate Similarity	NPC284078
0.7956	Intermediate Similarity	NPC83279
0.7926	Intermediate Similarity	NPC293619
0.7914	Intermediate Similarity	NPC13020
0.7914	Intermediate Similarity	NPC140359
0.7905	Intermediate Similarity	NPC472091
0.7905	Intermediate Similarity	NPC472092
0.7905	Intermediate Similarity	NPC472090
0.7901	Intermediate Similarity	NPC225130
0.7883	Intermediate Similarity	NPC56214
0.7883	Intermediate Similarity	NPC117780
0.7883	Intermediate Similarity	NPC227217
0.7883	Intermediate Similarity	NPC165133
0.7883	Intermediate Similarity	NPC95614
0.7883	Intermediate Similarity	NPC242885
0.7883	Intermediate Similarity	NPC232316
0.7875	Intermediate Similarity	NPC317272
0.7875	Intermediate Similarity	NPC256012
0.7875	Intermediate Similarity	NPC250846
0.7875	Intermediate Similarity	NPC240841
0.7875	Intermediate Similarity	NPC268503
0.7875	Intermediate Similarity	NPC42549
0.7853	Intermediate Similarity	NPC469979
0.7842	Intermediate Similarity	NPC85488
0.7838	Intermediate Similarity	NPC260842
0.7832	Intermediate Similarity	NPC470706
0.7826	Intermediate Similarity	NPC207613
0.7823	Intermediate Similarity	NPC193528
0.7817	Intermediate Similarity	NPC291449
0.7817	Intermediate Similarity	NPC41331
0.7815	Intermediate Similarity	NPC238216
0.7815	Intermediate Similarity	NPC84684
0.7815	Intermediate Similarity	NPC185388
0.7815	Intermediate Similarity	NPC208994
0.781	Intermediate Similarity	NPC310338
0.781	Intermediate Similarity	NPC281298
0.7808	Intermediate Similarity	NPC141023
0.7805	Intermediate Similarity	NPC473462
0.7805	Intermediate Similarity	NPC126128
0.7805	Intermediate Similarity	NPC207819
0.7805	Intermediate Similarity	NPC110454
0.7805	Intermediate Similarity	NPC298981
0.7801	Intermediate Similarity	NPC29008
0.7801	Intermediate Similarity	NPC228771
0.7801	Intermediate Similarity	NPC266705
0.78	Intermediate Similarity	NPC472088
0.78	Intermediate Similarity	NPC472087
0.7792	Intermediate Similarity	NPC478189
0.7786	Intermediate Similarity	NPC280704
0.777	Intermediate Similarity	NPC184651
0.777	Intermediate Similarity	NPC262156
0.777	Intermediate Similarity	NPC160380
0.777	Intermediate Similarity	NPC113865
0.777	Intermediate Similarity	NPC343720
0.777	Intermediate Similarity	NPC38996
0.777	Intermediate Similarity	NPC473853
0.777	Intermediate Similarity	NPC54872
0.777	Intermediate Similarity	NPC324571
0.777	Intermediate Similarity	NPC470212
0.777	Intermediate Similarity	NPC312675
0.7763	Intermediate Similarity	NPC473909
0.7763	Intermediate Similarity	NPC143120
0.7763	Intermediate Similarity	NPC274960
0.7762	Intermediate Similarity	NPC307050
0.7762	Intermediate Similarity	NPC277458
0.7758	Intermediate Similarity	NPC290534
0.7758	Intermediate Similarity	NPC32064
0.7754	Intermediate Similarity	NPC263835
0.7751	Intermediate Similarity	NPC124626
0.7746	Intermediate Similarity	NPC251466
0.7746	Intermediate Similarity	NPC156944
0.7744	Intermediate Similarity	NPC226001
0.7733	Intermediate Similarity	NPC472089
0.773	Intermediate Similarity	NPC476751
0.7714	Intermediate Similarity	NPC471314
0.7714	Intermediate Similarity	NPC471315
0.7708	Intermediate Similarity	NPC83062
0.7703	Intermediate Similarity	NPC77861
0.7703	Intermediate Similarity	NPC120852
0.7698	Intermediate Similarity	NPC189844
0.7698	Intermediate Similarity	NPC109083
0.7698	Intermediate Similarity	NPC224814
0.7698	Intermediate Similarity	NPC269843
0.7698	Intermediate Similarity	NPC60962
0.7698	Intermediate Similarity	NPC14007
0.7692	Intermediate Similarity	NPC191302
0.7692	Intermediate Similarity	NPC99798
0.7692	Intermediate Similarity	NPC157740
0.7683	Intermediate Similarity	NPC475215
0.7683	Intermediate Similarity	NPC108434
0.7676	Intermediate Similarity	NPC71105
0.7676	Intermediate Similarity	NPC29477
0.7676	Intermediate Similarity	NPC207541
0.7676	Intermediate Similarity	NPC152186
0.7676	Intermediate Similarity	NPC182147
0.7676	Intermediate Similarity	NPC170583
0.7676	Intermediate Similarity	NPC9067
0.7676	Intermediate Similarity	NPC246133
0.7671	Intermediate Similarity	NPC303144
0.7671	Intermediate Similarity	NPC189482
0.7671	Intermediate Similarity	NPC73656
0.7671	Intermediate Similarity	NPC474134
0.7671	Intermediate Similarity	NPC131128
0.7669	Intermediate Similarity	NPC66573
0.7667	Intermediate Similarity	NPC262189
0.7667	Intermediate Similarity	NPC22317
0.7665	Intermediate Similarity	NPC214188
0.7665	Intermediate Similarity	NPC301941
0.7665	Intermediate Similarity	NPC74618
0.7664	Intermediate Similarity	NPC86947
0.7662	Intermediate Similarity	NPC476571
0.7662	Intermediate Similarity	NPC428
0.7662	Intermediate Similarity	NPC135538
0.7662	Intermediate Similarity	NPC147390
0.7662	Intermediate Similarity	NPC246587
0.7662	Intermediate Similarity	NPC24233
0.7662	Intermediate Similarity	NPC262297
0.766	Intermediate Similarity	NPC31344
0.766	Intermediate Similarity	NPC317769
0.766	Intermediate Similarity	NPC471693
0.7655	Intermediate Similarity	NPC329595
0.7655	Intermediate Similarity	NPC326599
0.7651	Intermediate Similarity	NPC474390
0.7647	Intermediate Similarity	NPC470951
0.7643	Intermediate Similarity	NPC56635
0.7639	Intermediate Similarity	NPC246974
0.7639	Intermediate Similarity	NPC474178
0.7639	Intermediate Similarity	NPC245826
0.7639	Intermediate Similarity	NPC147247
0.7639	Intermediate Similarity	NPC252307
0.7635	Intermediate Similarity	NPC93783
0.7633	Intermediate Similarity	NPC49172
0.7626	Intermediate Similarity	NPC471308
0.7626	Intermediate Similarity	NPC160120
0.7626	Intermediate Similarity	NPC289330
0.7626	Intermediate Similarity	NPC53596
0.7626	Intermediate Similarity	NPC17388
0.7622	Intermediate Similarity	NPC276014
0.7622	Intermediate Similarity	NPC178284
0.7622	Intermediate Similarity	NPC191037
0.7622	Intermediate Similarity	NPC58607
0.7616	Intermediate Similarity	NPC318805
0.7616	Intermediate Similarity	NPC41122

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 NPC222039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	731
0.2-0.3	1178
0.3-0.4	2124
0.4-0.5	2579
0.5-0.6	1581
0.6-0.7	707
0.7-0.8	98
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8357	Intermediate Similarity	NPD2674	Phase 3
0.8286	Intermediate Similarity	NPD3145	Approved
0.8286	Intermediate Similarity	NPD3144	Approved
0.7947	Intermediate Similarity	NPD4123	Phase 3
0.7935	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2922	Phase 1
0.78	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6331	Phase 2
0.7778	Intermediate Similarity	NPD5718	Phase 2
0.7714	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4675	Approved
0.7692	Intermediate Similarity	NPD4678	Approved
0.7667	Intermediate Similarity	NPD7153	Discontinued
0.766	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3060	Approved
0.7612	Intermediate Similarity	NPD228	Approved
0.7551	Intermediate Similarity	NPD1558	Phase 1
0.7551	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1669	Approved
0.7533	Intermediate Similarity	NPD2161	Phase 2
0.7517	Intermediate Similarity	NPD6896	Approved
0.7517	Intermediate Similarity	NPD6895	Approved
0.7516	Intermediate Similarity	NPD5241	Discontinued
0.7516	Intermediate Similarity	NPD4005	Discontinued
0.75	Intermediate Similarity	NPD2122	Discontinued
0.75	Intermediate Similarity	NPD6584	Phase 3
0.7484	Intermediate Similarity	NPD4739	Approved
0.7483	Intermediate Similarity	NPD7477	Discontinued
0.7466	Intermediate Similarity	NPD3027	Phase 3
0.7438	Intermediate Similarity	NPD5773	Approved
0.7438	Intermediate Similarity	NPD5772	Approved
0.7436	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7526	Approved
0.7436	Intermediate Similarity	NPD52	Approved
0.7423	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5111	Phase 2
0.7415	Intermediate Similarity	NPD5109	Approved
0.7415	Intermediate Similarity	NPD5110	Phase 2
0.7407	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7833	Phase 2
0.7407	Intermediate Similarity	NPD7831	Phase 2
0.7386	Intermediate Similarity	NPD4162	Approved
0.7386	Intermediate Similarity	NPD5177	Phase 3
0.7372	Intermediate Similarity	NPD5283	Phase 1
0.7368	Intermediate Similarity	NPD8053	Approved
0.7368	Intermediate Similarity	NPD8054	Approved
0.7361	Intermediate Similarity	NPD5310	Approved
0.7361	Intermediate Similarity	NPD5311	Approved
0.7346	Intermediate Similarity	NPD7773	Phase 2
0.7329	Intermediate Similarity	NPD2978	Approved
0.7329	Intermediate Similarity	NPD2977	Approved
0.7308	Intermediate Similarity	NPD4357	Discontinued
0.7301	Intermediate Similarity	NPD5604	Discontinued
0.7292	Intermediate Similarity	NPD6583	Phase 3
0.7292	Intermediate Similarity	NPD6582	Phase 2
0.729	Intermediate Similarity	NPD2219	Phase 1
0.726	Intermediate Similarity	NPD7451	Discontinued
0.7255	Intermediate Similarity	NPD1375	Discontinued
0.7254	Intermediate Similarity	NPD2668	Approved
0.7254	Intermediate Similarity	NPD2667	Approved
0.7237	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2233	Approved
0.7222	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2230	Approved
0.7222	Intermediate Similarity	NPD2232	Approved
0.7219	Intermediate Similarity	NPD5314	Approved
0.7208	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7438	Suspended
0.7192	Intermediate Similarity	NPD3055	Approved
0.7192	Intermediate Similarity	NPD3053	Approved
0.7186	Intermediate Similarity	NPD4083	Discontinued
0.7161	Intermediate Similarity	NPD4236	Phase 3
0.7161	Intermediate Similarity	NPD4237	Approved
0.716	Intermediate Similarity	NPD5722	Discontinued
0.7143	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7124	Phase 2
0.7134	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD839	Approved
0.7133	Intermediate Similarity	NPD840	Approved
0.7123	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7037	Approved
0.7097	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4993	Discontinued
0.7086	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3061	Approved
0.7086	Intermediate Similarity	NPD3620	Phase 2
0.7086	Intermediate Similarity	NPD3062	Approved
0.7086	Intermediate Similarity	NPD3059	Approved
0.7081	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3022	Approved
0.708	Intermediate Similarity	NPD3021	Approved
0.7067	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD9379	Approved
0.705	Intermediate Similarity	NPD9377	Approved
0.7047	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4584	Approved
0.7044	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5536	Phase 2
0.7027	Intermediate Similarity	NPD7905	Discontinued
0.7013	Intermediate Similarity	NPD4108	Discontinued
0.7	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4055	Discovery
0.6988	Remote Similarity	NPD8070	Approved
0.6986	Remote Similarity	NPD2231	Phase 2
0.6986	Remote Similarity	NPD2235	Phase 2
0.698	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1613	Approved
0.6964	Remote Similarity	NPD7802	Discontinued
0.6962	Remote Similarity	NPD3692	Discontinued
0.6962	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8251	Approved
0.6959	Remote Similarity	NPD8099	Discontinued
0.6959	Remote Similarity	NPD8252	Approved
0.6957	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7906	Approved
0.6944	Remote Similarity	NPD4093	Discontinued
0.6944	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2983	Phase 2
0.6939	Remote Similarity	NPD2982	Phase 2
0.6937	Remote Similarity	NPD7447	Phase 1
0.6933	Remote Similarity	NPD6502	Phase 2
0.6929	Remote Similarity	NPD7843	Approved
0.6923	Remote Similarity	NPD3656	Approved
0.6923	Remote Similarity	NPD4010	Discontinued
0.6923	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8156	Discontinued
0.6914	Remote Similarity	NPD3686	Approved
0.6914	Remote Similarity	NPD3687	Approved
0.6909	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9384	Approved
0.6897	Remote Similarity	NPD9381	Approved
0.689	Remote Similarity	NPD6072	Discontinued
0.689	Remote Similarity	NPD3778	Approved
0.689	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7110	Phase 1
0.6887	Remote Similarity	NPD1024	Discontinued
0.6883	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2157	Approved
0.6883	Remote Similarity	NPD4097	Suspended
0.6883	Remote Similarity	NPD2653	Approved
0.6879	Remote Similarity	NPD2808	Discontinued
0.6875	Remote Similarity	NPD6581	Approved
0.6875	Remote Similarity	NPD6580	Approved
0.6871	Remote Similarity	NPD2981	Phase 2
0.6867	Remote Similarity	NPD1712	Approved
0.6863	Remote Similarity	NPD2238	Phase 2
0.686	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7131	Phase 3
0.6852	Remote Similarity	NPD6031	Approved
0.6852	Remote Similarity	NPD6030	Approved
0.6848	Remote Similarity	NPD5720	Discontinued
0.6848	Remote Similarity	NPD7298	Approved
0.6842	Remote Similarity	NPD27	Approved
0.6842	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2489	Approved
0.6839	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6111	Discontinued
0.6832	Remote Similarity	NPD7019	Approved
0.6832	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7020	Approved
0.6832	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3985	Discontinued
0.6828	Remote Similarity	NPD1357	Approved
0.6826	Remote Similarity	NPD6788	Approved
0.6824	Remote Similarity	NPD9622	Approved
0.6816	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7266	Discontinued
0.681	Remote Similarity	NPD2883	Discontinued
0.6809	Remote Similarity	NPD821	Approved
0.6805	Remote Similarity	NPD6746	Phase 2
0.68	Remote Similarity	NPD9619	Approved
0.68	Remote Similarity	NPD9620	Approved
0.68	Remote Similarity	NPD9621	Approved
0.6797	Remote Similarity	NPD3530	Approved
0.6797	Remote Similarity	NPD3532	Approved
0.6797	Remote Similarity	NPD3531	Approved
0.6797	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6386	Approved
0.6788	Remote Similarity	NPD6385	Approved
0.6788	Remote Similarity	NPD6873	Phase 2
0.6783	Remote Similarity	NPD7157	Approved
0.6783	Remote Similarity	NPD709	Approved
0.6779	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7095	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