NPASS Compound

Structure

NPC221809 OpenBabel07101718232D 32 36 0 0 1 0 0 0 0 0999 V2000 2.7886 -2.8840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5628 1.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1304 -2.8840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3021 1.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7886 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0730 0.8326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3291 1.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9983 1.1333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3291 -2.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3605 -0.4116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9983 -0.4410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6168 -0.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3021 -2.0414 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0763 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6168 -2.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0730 -0.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2858 -0.7123 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3021 -0.3561 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 -1.1988 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3605 -1.9859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7886 -1.1988 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3291 -0.3561 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5628 -0.3561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5898 -2.0414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0598 -2.9113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5702 0.3461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1033 0.4865 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 -0.1304 -1.1988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2858 -1.6852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 5 1 0 0 0 0 4 7 1 0 0 0 0 5 19 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 22 1 0 0 0 0 8 28 1 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 11 17 2 0 0 0 0 11 28 1 0 0 0 0 12 22 1 0 0 0 0 12 30 1 0 0 0 0 13 29 1 0 0 0 0 14 23 1 6 0 0 0 15 25 2 0 0 0 0 15 29 1 0 0 0 0 16 26 2 0 0 0 0 16 31 1 0 0 0 0 18 17 1 6 0 0 0 18 32 1 0 0 0 0 19 23 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 6 0 0 0 20 31 1 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 21 32 1 0 0 0 0 22 24 1 1 0 0 0 22 30 1 0 0 0 0 23 10 1 1 0 0 0 24 13 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.19
Volume:	438.017
LogP:	2.264
LogD:	1.685
LogS:	-4.314
# Rotatable Bonds:	6
TPSA:	104.57
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	5.596
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.272
MDCK Permeability:	3.950820610043593e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.566
30% Bioavailability (F30%):	0.626

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.876
Plasma Protein Binding (PPB):	84.54082489013672%
Volume Distribution (VD):	1.675
Pgp-substrate:	14.584946632385254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.604
CYP2C19-substrate:	0.18
CYP2C9-inhibitor:	0.575
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	3.948
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.495
Drug-inuced Liver Injury (DILI):	0.872
AMES Toxicity:	0.858
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.268
Carcinogencity:	0.462
Eye Corrosion:	0.007
Eye Irritation:	0.276
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC221809

Natural Product ID:	NPC221809
*Common Name:**	Montanin C
IUPAC Name:	n.a.
Synonyms:	Montanin C
Standard InCHIKey:	AFRNHJDBERWLNW-AUBWASTASA-N
Standard InCHI:	InChI=1S/C24H30O8/c1-14-9-20(31-16(3)26)24(13-29-15(2)25)19(5-4-7-22(24)12-30-22)23(14)10-18(32-21(23)27)17-6-8-28-11-17/h6,8,11,14,18-20H,4-5,7,9-10,12-13H2,1-3H3/t14-,18-,19-,20+,22+,23-,24+/m1/s1
SMILES:	C[C@@H]1C[C@@H]([C@]2(COC(=O)C)[C@H](CCC[C@@]32CO3)[C@]21C[C@H](c1ccoc1)OC2=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507606
PubChem CID:	13944860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO32760	teucrium bicolor	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809611]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	66.4	ppm	PMID[515693]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Inhibition	=	25.03	%	PMID[515694]

☑ 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 NPC221809 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	390
0.1-0.2	1410
0.2-0.3	3023
0.3-0.4	5952
0.4-0.5	11271
0.5-0.6	9970
0.6-0.7	9169
0.7-0.8	1029
0.8-0.85	313
0.85-0.9	142
0.9-0.95	25
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC18135
0.9384	High Similarity	NPC75906
0.932	High Similarity	NPC57998
0.931	High Similarity	NPC195325
0.9296	High Similarity	NPC223415
0.9262	High Similarity	NPC299038
0.9257	High Similarity	NPC469850
0.9247	High Similarity	NPC476122
0.9247	High Similarity	NPC156189
0.9231	High Similarity	NPC251865
0.9195	High Similarity	NPC126723
0.9178	High Similarity	NPC470791
0.9178	High Similarity	NPC470790
0.9172	High Similarity	NPC470941
0.9161	High Similarity	NPC470741
0.9155	High Similarity	NPC20500
0.9145	High Similarity	NPC469846
0.9139	High Similarity	NPC305016
0.9133	High Similarity	NPC286722
0.9122	High Similarity	NPC476201
0.9122	High Similarity	NPC268905
0.9116	High Similarity	NPC469335
0.9116	High Similarity	NPC477404
0.9116	High Similarity	NPC196864
0.9116	High Similarity	NPC159927
0.911	High Similarity	NPC19747
0.9073	High Similarity	NPC475295
0.9073	High Similarity	NPC473473
0.9067	High Similarity	NPC209364
0.9067	High Similarity	NPC107646
0.906	High Similarity	NPC282445
0.9048	High Similarity	NPC472654
0.9013	High Similarity	NPC191828
0.9013	High Similarity	NPC475381
0.9013	High Similarity	NPC472653
0.9007	High Similarity	NPC470742
0.9007	High Similarity	NPC187149
0.9	High Similarity	NPC476262
0.9	High Similarity	NPC214541
0.9	High Similarity	NPC44675
0.8993	High Similarity	NPC469503
0.8973	High Similarity	NPC346
0.8968	High Similarity	NPC476850
0.8968	High Similarity	NPC472651
0.8968	High Similarity	NPC476861
0.8961	High Similarity	NPC123088
0.8958	High Similarity	NPC121158
0.8954	High Similarity	NPC472668
0.8954	High Similarity	NPC470939
0.8947	High Similarity	NPC474932
0.8947	High Similarity	NPC237155
0.8947	High Similarity	NPC475967
0.8944	High Similarity	NPC476943
0.894	High Similarity	NPC263265
0.894	High Similarity	NPC60973
0.8912	High Similarity	NPC250228
0.891	High Similarity	NPC271235
0.891	High Similarity	NPC472652
0.8896	High Similarity	NPC134254
0.8896	High Similarity	NPC476197
0.8896	High Similarity	NPC419
0.8896	High Similarity	NPC39986
0.8896	High Similarity	NPC471168
0.8896	High Similarity	NPC302369
0.8896	High Similarity	NPC472669
0.8889	High Similarity	NPC335761
0.8889	High Similarity	NPC25255
0.8882	High Similarity	NPC261597
0.8882	High Similarity	NPC249021
0.8882	High Similarity	NPC472772
0.8882	High Similarity	NPC36655
0.8882	High Similarity	NPC167142
0.8874	High Similarity	NPC469336
0.8873	High Similarity	NPC310830
0.8865	High Similarity	NPC92941
0.8844	High Similarity	NPC62799
0.8844	High Similarity	NPC262198
0.8839	High Similarity	NPC476857
0.8839	High Similarity	NPC476858
0.8839	High Similarity	NPC476856
0.8839	High Similarity	NPC476860
0.8836	High Similarity	NPC84479
0.8836	High Similarity	NPC476944
0.8836	High Similarity	NPC86935
0.8831	High Similarity	NPC117986
0.8831	High Similarity	NPC193798
0.8831	High Similarity	NPC471167
0.8831	High Similarity	NPC471166
0.8831	High Similarity	NPC197596
0.8831	High Similarity	NPC5079
0.8824	High Similarity	NPC475226
0.8816	High Similarity	NPC204663
0.8808	High Similarity	NPC30222
0.8808	High Similarity	NPC178932
0.8808	High Similarity	NPC114880
0.8792	High Similarity	NPC211625
0.8784	High Similarity	NPC255414
0.8782	High Similarity	NPC23387
0.8782	High Similarity	NPC472141
0.8774	High Similarity	NPC234660
0.8774	High Similarity	NPC51568
0.8767	High Similarity	NPC267632
0.8767	High Similarity	NPC205071
0.8758	High Similarity	NPC195131
0.8758	High Similarity	NPC472283
0.8758	High Similarity	NPC472776
0.8758	High Similarity	NPC472777
0.8758	High Similarity	NPC472778
0.875	High Similarity	NPC35000
0.875	High Similarity	NPC264943
0.8742	High Similarity	NPC182427
0.8742	High Similarity	NPC476940
0.8742	High Similarity	NPC308205
0.8742	High Similarity	NPC29695
0.8742	High Similarity	NPC476939
0.8742	High Similarity	NPC322546
0.8733	High Similarity	NPC476936
0.8726	High Similarity	NPC173516
0.8726	High Similarity	NPC472282
0.8726	High Similarity	NPC473766
0.8726	High Similarity	NPC476853
0.8726	High Similarity	NPC473753
0.8718	High Similarity	NPC271657
0.871	High Similarity	NPC149896
0.871	High Similarity	NPC329938
0.871	High Similarity	NPC82851
0.871	High Similarity	NPC200782
0.871	High Similarity	NPC18347
0.871	High Similarity	NPC472771
0.8701	High Similarity	NPC307383
0.8693	High Similarity	NPC104736
0.869	High Similarity	NPC67003
0.8681	High Similarity	NPC220094
0.8675	High Similarity	NPC116717
0.8671	High Similarity	NPC471397
0.8671	High Similarity	NPC160651
0.8671	High Similarity	NPC46896
0.8667	High Similarity	NPC471001
0.8667	High Similarity	NPC125182
0.8667	High Similarity	NPC69647
0.8654	High Similarity	NPC663
0.8654	High Similarity	NPC469338
0.8654	High Similarity	NPC292389
0.8654	High Similarity	NPC472139
0.8654	High Similarity	NPC224394
0.8654	High Similarity	NPC477405
0.8654	High Similarity	NPC165218
0.8654	High Similarity	NPC472773
0.8649	High Similarity	NPC41182
0.8645	High Similarity	NPC470789
0.8639	High Similarity	NPC243577
0.8636	High Similarity	NPC45101
0.8636	High Similarity	NPC470118
0.8636	High Similarity	NPC304692
0.8625	High Similarity	NPC469848
0.8621	High Similarity	NPC90953
0.8616	High Similarity	NPC82602
0.8611	High Similarity	NPC310043
0.8599	High Similarity	NPC276735
0.8599	High Similarity	NPC469849
0.8599	High Similarity	NPC276551
0.8599	High Similarity	NPC470182
0.8599	High Similarity	NPC470940
0.859	High Similarity	NPC188649
0.859	High Similarity	NPC472767
0.859	High Similarity	NPC69028
0.859	High Similarity	NPC6326
0.859	High Similarity	NPC96443
0.859	High Similarity	NPC290400
0.8582	High Similarity	NPC298190
0.8581	High Similarity	NPC142113
0.8581	High Similarity	NPC477403
0.8581	High Similarity	NPC474611
0.8571	High Similarity	NPC41880
0.8571	High Similarity	NPC473152
0.8562	High Similarity	NPC56197
0.8562	High Similarity	NPC159232
0.8553	High Similarity	NPC240214
0.8552	High Similarity	NPC236532
0.8544	High Similarity	NPC214600
0.8544	High Similarity	NPC478178
0.8544	High Similarity	NPC470875
0.8542	High Similarity	NPC214572
0.8542	High Similarity	NPC146872
0.8535	High Similarity	NPC88841
0.8535	High Similarity	NPC285567
0.8535	High Similarity	NPC288602
0.8533	High Similarity	NPC216755
0.8533	High Similarity	NPC471174
0.8526	High Similarity	NPC477402
0.8523	High Similarity	NPC5676
0.8516	High Similarity	NPC475066
0.8516	High Similarity	NPC214495
0.8516	High Similarity	NPC470119
0.8516	High Similarity	NPC469847
0.8514	High Similarity	NPC476946
0.8511	High Similarity	NPC21460
0.85	High Similarity	NPC302392
0.85	High Similarity	NPC470995
0.8497	Intermediate Similarity	NPC471002

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 NPC221809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	943
0.2-0.3	2110
0.3-0.4	2690
0.4-0.5	1950
0.5-0.6	860
0.6-0.7	261
0.7-0.8	12
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8627	High Similarity	NPD5760	Phase 2
0.8627	High Similarity	NPD5761	Phase 2
0.795	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD8434	Phase 2
0.7658	Intermediate Similarity	NPD920	Approved
0.7532	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6764	Approved
0.7442	Intermediate Similarity	NPD6765	Approved
0.7405	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD7819	Suspended
0.7308	Intermediate Similarity	NPD1471	Phase 3
0.7308	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD6785	Approved
0.7273	Intermediate Similarity	NPD6784	Approved
0.7262	Intermediate Similarity	NPD5494	Approved
0.7244	Intermediate Similarity	NPD2796	Approved
0.7219	Intermediate Similarity	NPD6832	Phase 2
0.7215	Intermediate Similarity	NPD1243	Approved
0.7205	Intermediate Similarity	NPD2532	Approved
0.7205	Intermediate Similarity	NPD2533	Approved
0.7205	Intermediate Similarity	NPD2534	Approved
0.7202	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD6559	Discontinued
0.7134	Intermediate Similarity	NPD3226	Approved
0.711	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2799	Discontinued
0.7066	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6273	Approved
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7041	Intermediate Similarity	NPD7075	Discontinued
0.7037	Intermediate Similarity	NPD6799	Approved
0.7025	Intermediate Similarity	NPD1551	Phase 2
0.7018	Intermediate Similarity	NPD1247	Approved
0.7006	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2346	Discontinued
0.6962	Remote Similarity	NPD3748	Approved
0.6959	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3926	Phase 2
0.6923	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3817	Phase 2
0.6918	Remote Similarity	NPD2935	Discontinued
0.6894	Remote Similarity	NPD2800	Approved
0.689	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4967	Phase 2
0.6882	Remote Similarity	NPD4966	Approved
0.6882	Remote Similarity	NPD4965	Approved
0.6879	Remote Similarity	NPD6808	Phase 2
0.6879	Remote Similarity	NPD6232	Discontinued
0.6875	Remote Similarity	NPD2344	Approved
0.6875	Remote Similarity	NPD5844	Phase 1
0.6864	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7473	Discontinued
0.6855	Remote Similarity	NPD7033	Discontinued
0.6832	Remote Similarity	NPD1549	Phase 2
0.6826	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5402	Approved
0.6821	Remote Similarity	NPD3972	Approved
0.6821	Remote Similarity	NPD8127	Discontinued
0.6821	Remote Similarity	NPD1608	Approved
0.6821	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD3818	Discontinued
0.6815	Remote Similarity	NPD4307	Phase 2
0.6807	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6234	Discontinued
0.6802	Remote Similarity	NPD8404	Phase 2
0.68	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2313	Discontinued
0.6788	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4380	Phase 2
0.6784	Remote Similarity	NPD7768	Phase 2
0.6784	Remote Similarity	NPD3882	Suspended
0.6779	Remote Similarity	NPD5585	Approved
0.677	Remote Similarity	NPD6004	Phase 3
0.677	Remote Similarity	NPD6005	Phase 3
0.677	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6002	Phase 3
0.677	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1019	Discontinued
0.6752	Remote Similarity	NPD8032	Phase 2
0.6748	Remote Similarity	NPD3750	Approved
0.6747	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2979	Phase 3
0.6708	Remote Similarity	NPD6100	Approved
0.6708	Remote Similarity	NPD6099	Approved
0.6708	Remote Similarity	NPD2438	Suspended
0.6707	Remote Similarity	NPD2309	Approved
0.6707	Remote Similarity	NPD5403	Approved
0.6706	Remote Similarity	NPD37	Approved
0.6706	Remote Similarity	NPD1934	Approved
0.6703	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3266	Approved
0.6688	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3267	Approved
0.6688	Remote Similarity	NPD3764	Approved
0.6687	Remote Similarity	NPD5401	Approved
0.6686	Remote Similarity	NPD5711	Approved
0.6686	Remote Similarity	NPD5710	Approved
0.6686	Remote Similarity	NPD7229	Phase 3
0.6685	Remote Similarity	NPD8312	Approved
0.6685	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD8285	Discontinued
0.6646	Remote Similarity	NPD4308	Phase 3
0.6646	Remote Similarity	NPD1510	Phase 2
0.6646	Remote Similarity	NPD7003	Approved
0.6645	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7799	Discontinued
0.6629	Remote Similarity	NPD7199	Phase 2
0.6628	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7458	Discontinued
0.6625	Remote Similarity	NPD1607	Approved
0.6611	Remote Similarity	NPD5953	Discontinued
0.6608	Remote Similarity	NPD6279	Approved
0.6608	Remote Similarity	NPD6280	Approved
0.6606	Remote Similarity	NPD3887	Approved
0.6604	Remote Similarity	NPD1240	Approved
0.6601	Remote Similarity	NPD9717	Approved
0.6582	Remote Similarity	NPD3268	Approved
0.6581	Remote Similarity	NPD1203	Approved
0.6581	Remote Similarity	NPD2797	Approved
0.6575	Remote Similarity	NPD7685	Pre-registration
0.657	Remote Similarity	NPD2801	Approved
0.6568	Remote Similarity	NPD7239	Suspended
0.6562	Remote Similarity	NPD6355	Discontinued
0.6562	Remote Similarity	NPD1933	Approved
0.6562	Remote Similarity	NPD447	Suspended
0.6558	Remote Similarity	NPD4359	Approved
0.6554	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4110	Phase 3
0.6545	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2798	Approved
0.6538	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1281	Approved
0.6536	Remote Similarity	NPD3751	Discontinued
0.6536	Remote Similarity	NPD7228	Approved
0.6527	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6166	Phase 2
0.6517	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD1876	Approved
0.6513	Remote Similarity	NPD1778	Approved
0.6513	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7286	Phase 2
0.65	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4140	Approved
0.6497	Remote Similarity	NPD3787	Discontinued
0.6486	Remote Similarity	NPD8150	Discontinued
0.6478	Remote Similarity	NPD411	Approved
0.6474	Remote Similarity	NPD1465	Phase 2
0.6464	Remote Similarity	NPD7074	Phase 3
0.6461	Remote Similarity	NPD5242	Approved
0.6458	Remote Similarity	NPD4107	Approved
0.6453	Remote Similarity	NPD6385	Approved
0.6453	Remote Similarity	NPD6386	Approved
0.6453	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5691	Approved
0.6444	Remote Similarity	NPD7177	Discontinued
0.6438	Remote Similarity	NPD4870	Approved
0.6437	Remote Similarity	NPD5353	Approved
0.6429	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1511	Approved
0.6425	Remote Similarity	NPD2403	Approved
0.642	Remote Similarity	NPD6651	Approved
0.6417	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1283	Approved
0.6409	Remote Similarity	NPD7054	Approved
0.6404	Remote Similarity	NPD7315	Approved
0.6402	Remote Similarity	NPD2531	Phase 2
0.6393	Remote Similarity	NPD7240	Approved
0.6382	Remote Similarity	NPD9545	Approved
0.638	Remote Similarity	NPD7097	Phase 1
0.6378	Remote Similarity	NPD8407	Phase 2
0.6376	Remote Similarity	NPD1241	Discontinued
0.6374	Remote Similarity	NPD7472	Approved
0.6369	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2353	Approved
0.6364	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5762	Approved
0.6364	Remote Similarity	NPD5763	Approved
0.6359	Remote Similarity	NPD7435	Discontinued
0.6359	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7497	Discontinued
0.6358	Remote Similarity	NPD5890	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