NPASS Compound

Structure

CID324598 OpenBabel06191716172D 35 40 0 0 1 0 0 0 0 0999 V2000 4.2636 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2638 2.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0034 4.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4917 3.8132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8159 2.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7235 0.9951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8774 -0.5066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0604 -0.2000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5399 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 -0.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 1.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5394 3.4207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6930 2.9324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 -1.4654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2367 1.4168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6928 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8467 1.4665 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8466 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0268 1.9908 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5399 1.4665 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3860 2.9319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0268 2.9674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5151 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3863 1.9548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5151 3.8132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 1.9553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8461 0.4885 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2519 3.4320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0892 -0.3021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8169 1.4168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 3.8132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 33 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 18 17 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 31 1 0 0 0 0 22 17 1 1 0 0 0 22 25 1 0 0 0 0 22 34 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 6 0 0 0 24 27 1 0 0 0 0 24 32 1 6 0 0 0 25 28 1 0 0 0 0 25 35 1 1 0 0 0 26 33 1 1 0 0 0 26 34 1 0 0 0 0 28 35 1 0 0 0 0 29 5 1 6 0 0 0 30 31 1 1 0 0 0 31 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.37
Volume:	525.918
LogP:	6.934
LogD:	5.126
LogS:	-5.238
# Rotatable Bonds:	3
TPSA:	51.22
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	5.099
Fsp3:	0.935
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.83
MDCK Permeability:	1.2880590475106146e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.647

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	95.74080657958984%
Volume Distribution (VD):	1.708
Pgp-substrate:	3.779775619506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.615
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.726

ADMET: Excretion

Clearance (CL):	5.666
Half-life (T1/2):	0.022

ADMET: Toxicity

hERG Blockers:	0.343
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.936
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.448
Carcinogencity:	0.103
Eye Corrosion:	0.035
Eye Irritation:	0.051
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC324598

Natural Product ID:	NPC324598
*Common Name:**	Meliasenin P
IUPAC Name:	(3S,5R,9R,10R,13S,14S,17S)-17-[(2S,3S,5R)-5-[(2S)-3,3-dimethyloxiran-2-yl]-2-methoxyoxolan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	Meliasenin P
Standard InCHIKey:	GAXWPVGTBQUYCI-HGVUNVDQSA-N
Standard InCHI:	InChI=1S/C31H50O4/c1-27(2)23-10-9-21-20(29(23,5)14-13-24(27)32)12-16-30(6)19(11-15-31(21,30)7)18-17-22(34-26(18)33-8)25-28(3,4)35-25/h9,18-20,22-26,32H,10-17H2,1-8H3/t18-,19-,20-,22+,23-,24-,25-,26-,29+,30-,31+/m0/s1
SMILES:	CC1(C(CCC2(C1CC=C3C2CCC4(C3(CCC4C5CC(OC5OC)C6C(O6)(C)C)C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641924
PubChem CID:	50900243
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	48.7	ug.mL-1	PMID[569919]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6.4	ug.mL-1	PMID[569919]

☑ 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 NPC324598 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	235
0.1-0.2	1778
0.2-0.3	6281
0.3-0.4	14325
0.4-0.5	8006
0.5-0.6	5445
0.6-0.7	4943
0.7-0.8	1540
0.8-0.85	114
0.85-0.9	25
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC216260
0.9677	High Similarity	NPC5358
0.9184	High Similarity	NPC31430
0.9184	High Similarity	NPC85593
0.9082	High Similarity	NPC213190
0.89	High Similarity	NPC26798
0.8889	High Similarity	NPC471887
0.8889	High Similarity	NPC471888
0.8889	High Similarity	NPC471886
0.8889	High Similarity	NPC471885
0.8889	High Similarity	NPC475701
0.8878	High Similarity	NPC309425
0.8878	High Similarity	NPC129372
0.8878	High Similarity	NPC88000
0.8878	High Similarity	NPC160734
0.8878	High Similarity	NPC472023
0.8878	High Similarity	NPC47566
0.8878	High Similarity	NPC4831
0.8866	High Similarity	NPC280825
0.8866	High Similarity	NPC234287
0.8824	High Similarity	NPC476835
0.8812	High Similarity	NPC226642
0.88	High Similarity	NPC474464
0.88	High Similarity	NPC187400
0.88	High Similarity	NPC470885
0.88	High Similarity	NPC471111
0.88	High Similarity	NPC221562
0.8788	High Similarity	NPC300399
0.8788	High Similarity	NPC471482
0.8788	High Similarity	NPC37207
0.8788	High Similarity	NPC136816
0.8776	High Similarity	NPC7341
0.8776	High Similarity	NPC473200
0.8763	High Similarity	NPC243728
0.8763	High Similarity	NPC473890
0.8738	High Similarity	NPC103627
0.8738	High Similarity	NPC170974
0.8738	High Similarity	NPC191439
0.8738	High Similarity	NPC101450
0.8725	High Similarity	NPC220427
0.8713	High Similarity	NPC474015
0.87	High Similarity	NPC245280
0.87	High Similarity	NPC211879
0.87	High Similarity	NPC8039
0.87	High Similarity	NPC157659
0.87	High Similarity	NPC31907
0.87	High Similarity	NPC189852
0.87	High Similarity	NPC155010
0.87	High Similarity	NPC473020
0.87	High Similarity	NPC16520
0.87	High Similarity	NPC471450
0.87	High Similarity	NPC286969
0.87	High Similarity	NPC472252
0.87	High Similarity	NPC114874
0.87	High Similarity	NPC131479
0.87	High Similarity	NPC120123
0.8687	High Similarity	NPC474022
0.8673	High Similarity	NPC158088
0.8673	High Similarity	NPC309493
0.866	High Similarity	NPC207617
0.8654	High Similarity	NPC65034
0.8654	High Similarity	NPC197231
0.8654	High Similarity	NPC208189
0.8646	High Similarity	NPC305160
0.8641	High Similarity	NPC473318
0.8641	High Similarity	NPC14630
0.8641	High Similarity	NPC472901
0.8641	High Similarity	NPC250089
0.8641	High Similarity	NPC28844
0.8641	High Similarity	NPC473328
0.8641	High Similarity	NPC157530
0.8632	High Similarity	NPC210268
0.8627	High Similarity	NPC190395
0.8617	High Similarity	NPC473058
0.8614	High Similarity	NPC470059
0.8614	High Similarity	NPC165033
0.8614	High Similarity	NPC470060
0.8614	High Similarity	NPC470062
0.8614	High Similarity	NPC470061
0.8614	High Similarity	NPC470043
0.8614	High Similarity	NPC475365
0.8614	High Similarity	NPC470058
0.8614	High Similarity	NPC470057
0.8614	High Similarity	NPC121566
0.8614	High Similarity	NPC273879
0.8614	High Similarity	NPC75608
0.8614	High Similarity	NPC100955
0.8614	High Similarity	NPC470064
0.86	High Similarity	NPC312553
0.86	High Similarity	NPC288694
0.86	High Similarity	NPC22634
0.86	High Similarity	NPC159036
0.86	High Similarity	NPC471889
0.8586	High Similarity	NPC282669
0.8571	High Similarity	NPC177818
0.8571	High Similarity	NPC231797
0.8571	High Similarity	NPC19888
0.8558	High Similarity	NPC65155
0.8544	High Similarity	NPC476541
0.8544	High Similarity	NPC476538
0.8544	High Similarity	NPC476539
0.8544	High Similarity	NPC476540
0.8542	High Similarity	NPC98193
0.8529	High Similarity	NPC472899
0.8529	High Similarity	NPC473199
0.8529	High Similarity	NPC63023
0.8529	High Similarity	NPC208594
0.8529	High Similarity	NPC152584
0.8529	High Similarity	NPC309448
0.8529	High Similarity	NPC472900
0.8529	High Similarity	NPC472898
0.8529	High Similarity	NPC269627
0.8529	High Similarity	NPC95243
0.8529	High Similarity	NPC181845
0.8529	High Similarity	NPC160816
0.8529	High Similarity	NPC194842
0.8529	High Similarity	NPC208477
0.8529	High Similarity	NPC127801
0.8529	High Similarity	NPC242748
0.8529	High Similarity	NPC69737
0.8526	High Similarity	NPC159876
0.8515	High Similarity	NPC16573
0.8515	High Similarity	NPC473198
0.8505	High Similarity	NPC212660
0.85	High Similarity	NPC476896
0.85	High Similarity	NPC267510
0.85	High Similarity	NPC470434
0.8495	Intermediate Similarity	NPC125399
0.8491	Intermediate Similarity	NPC471173
0.8491	Intermediate Similarity	NPC476671
0.8491	Intermediate Similarity	NPC471627
0.8485	Intermediate Similarity	NPC275865
0.8476	Intermediate Similarity	NPC472987
0.8476	Intermediate Similarity	NPC473021
0.8469	Intermediate Similarity	NPC90583
0.8469	Intermediate Similarity	NPC472989
0.8462	Intermediate Similarity	NPC302057
0.8462	Intermediate Similarity	NPC306131
0.8462	Intermediate Similarity	NPC128133
0.8462	Intermediate Similarity	NPC477027
0.8462	Intermediate Similarity	NPC42482
0.8462	Intermediate Similarity	NPC477026
0.8462	Intermediate Similarity	NPC40440
0.8462	Intermediate Similarity	NPC475670
0.8462	Intermediate Similarity	NPC70204
0.8454	Intermediate Similarity	NPC72817
0.8454	Intermediate Similarity	NPC477927
0.8447	Intermediate Similarity	NPC305423
0.8447	Intermediate Similarity	NPC14946
0.8447	Intermediate Similarity	NPC230507
0.8447	Intermediate Similarity	NPC161676
0.8447	Intermediate Similarity	NPC33053
0.8447	Intermediate Similarity	NPC208650
0.8447	Intermediate Similarity	NPC470432
0.8447	Intermediate Similarity	NPC113044
0.8447	Intermediate Similarity	NPC283829
0.8447	Intermediate Similarity	NPC181467
0.8447	Intermediate Similarity	NPC231340
0.8447	Intermediate Similarity	NPC14704
0.8447	Intermediate Similarity	NPC63368
0.8431	Intermediate Similarity	NPC93352
0.8416	Intermediate Similarity	NPC154452
0.8416	Intermediate Similarity	NPC272015
0.8411	Intermediate Similarity	NPC477810
0.84	Intermediate Similarity	NPC469942
0.8365	Intermediate Similarity	NPC180183
0.8365	Intermediate Similarity	NPC6931
0.8365	Intermediate Similarity	NPC38217
0.8365	Intermediate Similarity	NPC159005
0.8365	Intermediate Similarity	NPC472988
0.8365	Intermediate Similarity	NPC98696
0.8365	Intermediate Similarity	NPC246124
0.8365	Intermediate Similarity	NPC7213
0.8351	Intermediate Similarity	NPC242419
0.8351	Intermediate Similarity	NPC235126
0.835	Intermediate Similarity	NPC473923
0.835	Intermediate Similarity	NPC470055
0.835	Intermediate Similarity	NPC473476
0.835	Intermediate Similarity	NPC474569
0.835	Intermediate Similarity	NPC470056
0.8333	Intermediate Similarity	NPC302471
0.8318	Intermediate Similarity	NPC144068
0.8318	Intermediate Similarity	NPC476693
0.8317	Intermediate Similarity	NPC285231
0.8317	Intermediate Similarity	NPC176406
0.8317	Intermediate Similarity	NPC21568
0.8317	Intermediate Similarity	NPC121072
0.8317	Intermediate Similarity	NPC21064
0.8302	Intermediate Similarity	NPC477028
0.8302	Intermediate Similarity	NPC477032
0.8302	Intermediate Similarity	NPC475247
0.8302	Intermediate Similarity	NPC294129
0.8302	Intermediate Similarity	NPC13190
0.8302	Intermediate Similarity	NPC124677
0.8302	Intermediate Similarity	NPC476547
0.83	Intermediate Similarity	NPC476895
0.8286	Intermediate Similarity	NPC248746
0.8286	Intermediate Similarity	NPC51925
0.8286	Intermediate Similarity	NPC22779
0.8286	Intermediate Similarity	NPC46190

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 NPC324598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1989
0.2-0.3	4396
0.3-0.4	1736
0.4-0.5	419
0.5-0.6	199
0.6-0.7	179
0.7-0.8	34
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7895	Intermediate Similarity	NPD6370	Approved
0.7857	Intermediate Similarity	NPD7328	Approved
0.7857	Intermediate Similarity	NPD7327	Approved
0.7849	Intermediate Similarity	NPD7525	Registered
0.7788	Intermediate Similarity	NPD7516	Approved
0.7757	Intermediate Similarity	NPD6412	Phase 2
0.7719	Intermediate Similarity	NPD6054	Approved
0.7719	Intermediate Similarity	NPD6059	Approved
0.7719	Intermediate Similarity	NPD8294	Approved
0.7719	Intermediate Similarity	NPD8377	Approved
0.7652	Intermediate Similarity	NPD8296	Approved
0.7652	Intermediate Similarity	NPD8380	Approved
0.7652	Intermediate Similarity	NPD8335	Approved
0.7652	Intermediate Similarity	NPD8379	Approved
0.7652	Intermediate Similarity	NPD8378	Approved
0.7652	Intermediate Similarity	NPD8033	Approved
0.7627	Intermediate Similarity	NPD8293	Discontinued
0.7563	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.7458	Intermediate Similarity	NPD7492	Approved
0.7436	Intermediate Similarity	NPD5988	Approved
0.7395	Intermediate Similarity	NPD6616	Approved
0.7395	Intermediate Similarity	NPD7507	Approved
0.7373	Intermediate Similarity	NPD6067	Discontinued
0.7347	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7078	Approved
0.7312	Intermediate Similarity	NPD7339	Approved
0.7312	Intermediate Similarity	NPD6942	Approved
0.73	Intermediate Similarity	NPD7524	Approved
0.7282	Intermediate Similarity	NPD8171	Discontinued
0.7245	Intermediate Similarity	NPD6695	Phase 3
0.7213	Intermediate Similarity	NPD7319	Approved
0.7188	Intermediate Similarity	NPD7645	Phase 2
0.7182	Intermediate Similarity	NPD6008	Approved
0.7155	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6033	Approved
0.7113	Intermediate Similarity	NPD6928	Phase 2
0.7105	Intermediate Similarity	NPD6882	Approved
0.7103	Intermediate Similarity	NPD7638	Approved
0.7054	Intermediate Similarity	NPD6686	Approved
0.7054	Intermediate Similarity	NPD7320	Approved
0.7053	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8133	Approved
0.7037	Intermediate Similarity	NPD7640	Approved
0.7037	Intermediate Similarity	NPD7639	Approved
0.7027	Intermediate Similarity	NPD5739	Approved
0.7027	Intermediate Similarity	NPD6402	Approved
0.7027	Intermediate Similarity	NPD7128	Approved
0.7027	Intermediate Similarity	NPD6675	Approved
0.6961	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7750	Discontinued
0.6957	Remote Similarity	NPD8297	Approved
0.6952	Remote Similarity	NPD6399	Phase 3
0.6939	Remote Similarity	NPD6931	Approved
0.6939	Remote Similarity	NPD6930	Phase 2
0.6923	Remote Similarity	NPD3168	Discontinued
0.6905	Remote Similarity	NPD8449	Approved
0.6903	Remote Similarity	NPD6881	Approved
0.6903	Remote Similarity	NPD6899	Approved
0.6897	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD6933	Approved
0.6864	Remote Similarity	NPD7115	Discovery
0.6852	Remote Similarity	NPD4755	Approved
0.685	Remote Similarity	NPD8450	Suspended
0.6842	Remote Similarity	NPD6373	Approved
0.6842	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6926	Approved
0.6842	Remote Similarity	NPD6372	Approved
0.6842	Remote Similarity	NPD6924	Approved
0.6837	Remote Similarity	NPD6929	Approved
0.6833	Remote Similarity	NPD6319	Approved
0.6832	Remote Similarity	NPD4786	Approved
0.6827	Remote Similarity	NPD5328	Approved
0.6814	Remote Similarity	NPD5701	Approved
0.6814	Remote Similarity	NPD5697	Approved
0.6809	Remote Similarity	NPD4243	Approved
0.6804	Remote Similarity	NPD6932	Approved
0.6803	Remote Similarity	NPD8328	Phase 3
0.6803	Remote Similarity	NPD7604	Phase 2
0.6792	Remote Similarity	NPD4202	Approved
0.6783	Remote Similarity	NPD7102	Approved
0.6783	Remote Similarity	NPD7290	Approved
0.6783	Remote Similarity	NPD6883	Approved
0.6727	Remote Similarity	NPD4696	Approved
0.6727	Remote Similarity	NPD4700	Approved
0.6727	Remote Similarity	NPD5286	Approved
0.6727	Remote Similarity	NPD5285	Approved
0.6724	Remote Similarity	NPD6847	Approved
0.6724	Remote Similarity	NPD8130	Phase 1
0.6724	Remote Similarity	NPD6869	Approved
0.6724	Remote Similarity	NPD6650	Approved
0.6724	Remote Similarity	NPD6617	Approved
0.6724	Remote Similarity	NPD6649	Approved
0.6723	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3618	Phase 1
0.6698	Remote Similarity	NPD7087	Discontinued
0.6698	Remote Similarity	NPD6079	Approved
0.6697	Remote Similarity	NPD6084	Phase 2
0.6697	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD6014	Approved
0.6696	Remote Similarity	NPD6012	Approved
0.6696	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6683	Phase 2
0.6667	Remote Similarity	NPD4784	Approved
0.6639	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD4634	Approved
0.6638	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3667	Approved
0.6633	Remote Similarity	NPD6925	Approved
0.6633	Remote Similarity	NPD5776	Phase 2
0.6614	Remote Similarity	NPD5956	Approved
0.6609	Remote Similarity	NPD6011	Approved
0.6607	Remote Similarity	NPD5211	Phase 2
0.6607	Remote Similarity	NPD5225	Approved
0.6607	Remote Similarity	NPD5226	Approved
0.6607	Remote Similarity	NPD5224	Approved
0.6607	Remote Similarity	NPD4633	Approved
0.6602	Remote Similarity	NPD6893	Approved
0.66	Remote Similarity	NPD7514	Phase 3
0.66	Remote Similarity	NPD4748	Discontinued
0.66	Remote Similarity	NPD7509	Discontinued
0.6596	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7145	Approved
0.656	Remote Similarity	NPD6336	Discontinued
0.6549	Remote Similarity	NPD5175	Approved
0.6549	Remote Similarity	NPD5174	Approved
0.6542	Remote Similarity	NPD8034	Phase 2
0.6542	Remote Similarity	NPD8035	Phase 2
0.6535	Remote Similarity	NPD6902	Approved
0.6518	Remote Similarity	NPD5223	Approved
0.6518	Remote Similarity	NPD5344	Discontinued
0.6509	Remote Similarity	NPD6051	Approved
0.6509	Remote Similarity	NPD4753	Phase 2
0.6495	Remote Similarity	NPD1810	Approved
0.6495	Remote Similarity	NPD1811	Approved
0.6491	Remote Similarity	NPD5141	Approved
0.6486	Remote Similarity	NPD4225	Approved
0.646	Remote Similarity	NPD7632	Discontinued
0.6458	Remote Similarity	NPD7150	Approved
0.6458	Remote Similarity	NPD7151	Approved
0.6458	Remote Similarity	NPD7152	Approved
0.6455	Remote Similarity	NPD4697	Phase 3
0.6455	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5221	Approved
0.6455	Remote Similarity	NPD5222	Approved
0.6442	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7332	Phase 2
0.6435	Remote Similarity	NPD4768	Approved
0.6435	Remote Similarity	NPD5357	Phase 1
0.6435	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD5275	Approved
0.6429	Remote Similarity	NPD4190	Phase 3
0.6422	Remote Similarity	NPD7748	Approved
0.6421	Remote Similarity	NPD6922	Approved
0.6421	Remote Similarity	NPD6923	Approved
0.6404	Remote Similarity	NPD4754	Approved
0.6396	Remote Similarity	NPD5173	Approved
0.6396	Remote Similarity	NPD7902	Approved
0.6389	Remote Similarity	NPD7637	Suspended
0.6389	Remote Similarity	NPD7515	Phase 2
0.6379	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6898	Phase 1
0.6371	Remote Similarity	NPD8516	Approved
0.6371	Remote Similarity	NPD8513	Phase 3
0.6371	Remote Similarity	NPD8517	Approved
0.6371	Remote Similarity	NPD8515	Approved
0.6364	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6354	Remote Similarity	NPD7143	Approved
0.6354	Remote Similarity	NPD7144	Approved
0.6346	Remote Similarity	NPD3133	Approved
0.6346	Remote Similarity	NPD3666	Approved
0.6346	Remote Similarity	NPD3665	Phase 1
0.6341	Remote Similarity	NPD7100	Approved
0.6341	Remote Similarity	NPD7101	Approved
0.6339	Remote Similarity	NPD5696	Approved
0.6337	Remote Similarity	NPD4195	Approved
0.6325	Remote Similarity	NPD4729	Approved
0.6325	Remote Similarity	NPD5128	Approved
0.6325	Remote Similarity	NPD4730	Approved
0.6283	Remote Similarity	NPD6648	Approved
0.6273	Remote Similarity	NPD6001	Approved
0.6262	Remote Similarity	NPD6903	Approved
0.6262	Remote Similarity	NPD6672	Approved
0.6262	Remote Similarity	NPD5737	Approved
0.626	Remote Similarity	NPD6335	Approved
0.6259	Remote Similarity	NPD7625	Phase 1
0.625	Remote Similarity	NPD6053	Discontinued
0.624	Remote Similarity	NPD6909	Approved
0.624	Remote Similarity	NPD6908	Approved
0.624	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6409	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