NPASS Compound

Structure

NPC473790 OpenBabel07101719252D 42 48 0 0 1 0 0 0 0 0999 V2000 -2.1865 -3.7871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2069 -3.7871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8832 2.8075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9036 2.8075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8832 0.8484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3730 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0262 2.5300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8746 2.0402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5451 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2418 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -1.4694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5451 1.4694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6967 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2418 1.4694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5451 -2.4490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5451 -1.4694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8484 0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6967 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6967 -2.9388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0262 1.5504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5451 0.4898 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8484 0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6967 -0.9796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0901 1.9592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 -2.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 0.4898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 -0.9796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0520 1.4480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4247 0.6555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 32 1 0 0 0 0 10 34 1 0 0 0 0 12 13 1 0 0 0 0 12 20 2 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 33 1 0 0 0 0 17 34 1 0 0 0 0 18 21 1 0 0 0 0 18 29 1 0 0 0 0 19 39 1 0 0 0 0 20 21 1 0 0 0 0 20 35 1 0 0 0 0 21 36 1 6 0 0 0 22 30 1 0 0 0 0 22 33 1 1 0 0 0 23 33 1 1 0 0 0 23 34 1 0 0 0 0 24 30 1 0 0 0 0 24 37 1 1 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 25 38 1 1 0 0 0 26 36 1 6 0 0 0 26 40 1 0 0 0 0 27 28 1 0 0 0 0 27 35 1 6 0 0 0 27 41 1 0 0 0 0 28 36 1 6 0 0 0 28 42 1 0 0 0 0 31 39 1 0 0 0 0 31 40 1 0 0 0 0 32 41 1 0 0 0 0 32 42 1 0 0 0 0 33 9 1 1 0 0 0 34 35 1 6 0 0 0 35 11 1 6 0 0 0 36 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.42
Volume:	621.422
LogP:	6.588
LogD:	4.766
LogS:	-5.807
# Rotatable Bonds:	0
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	6.026
Fsp3:	0.944
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.227
MDCK Permeability:	1.9927694665966555e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.09
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.634
Plasma Protein Binding (PPB):	86.7632827758789%
Volume Distribution (VD):	1.417
Pgp-substrate:	9.489933967590332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.148
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.195
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.303
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	7.949
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.138
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC473790

Natural Product ID:	NPC473790
*Common Name:**	PTKMWQFUPJEOER-UTAJMZNMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PTKMWQFUPJEOER-UTAJMZNMSA-N
Standard InCHI:	InChI=1S/C36H58O6/c1-29(2)18-21-20-12-13-23-33(9)16-15-24(37)30(3,4)22(33)14-17-34(23,10)35(20,11)27-28(42-32(7,8)41-27)36(21)19-39-31(5,6)40-26(36)25(29)38/h12,21-28,37-38H,13-19H2,1-11H3/t21-,22-,23+,24-,25-,26-,27-,28+,33-,34+,35-,36+/m0/s1
SMILES:	O[C@H]1[C@@H]2OC(C)(C)OC[C@@]32[C@@H]2OC(O[C@@H]2[C@@]2(C(=CC[C@H]4[C@@]2(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O)[C@@H]3CC1(C)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451943
PubChem CID:	44559566
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
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783160]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[542549]

☑ 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 NPC473790 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	242
0.1-0.2	1857
0.2-0.3	5785
0.3-0.4	13249
0.4-0.5	9918
0.5-0.6	5282
0.6-0.7	3522
0.7-0.8	1954
0.8-0.85	602
0.85-0.9	227
0.9-0.95	58
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9072	High Similarity	NPC117714
0.9072	High Similarity	NPC263756
0.899	High Similarity	NPC148603
0.898	High Similarity	NPC76497
0.898	High Similarity	NPC256133
0.898	High Similarity	NPC30289
0.898	High Similarity	NPC213674
0.8969	High Similarity	NPC282669
0.89	High Similarity	NPC173859
0.89	High Similarity	NPC470512
0.8889	High Similarity	NPC99627
0.8889	High Similarity	NPC123796
0.8889	High Similarity	NPC473129
0.8889	High Similarity	NPC16573
0.8889	High Similarity	NPC162354
0.8889	High Similarity	NPC473124
0.8889	High Similarity	NPC473123
0.8866	High Similarity	NPC280825
0.8866	High Similarity	NPC234287
0.8842	High Similarity	NPC477927
0.8842	High Similarity	NPC72817
0.8842	High Similarity	NPC305160
0.8812	High Similarity	NPC78034
0.88	High Similarity	NPC473734
0.88	High Similarity	NPC203354
0.88	High Similarity	NPC471434
0.88	High Similarity	NPC470885
0.88	High Similarity	NPC187400
0.88	High Similarity	NPC109792
0.88	High Similarity	NPC273879
0.88	High Similarity	NPC57065
0.88	High Similarity	NPC54521
0.88	High Similarity	NPC110656
0.88	High Similarity	NPC473127
0.88	High Similarity	NPC165033
0.88	High Similarity	NPC221562
0.88	High Similarity	NPC173583
0.88	High Similarity	NPC471435
0.88	High Similarity	NPC230948
0.8788	High Similarity	NPC312553
0.8788	High Similarity	NPC159036
0.8788	High Similarity	NPC136816
0.8788	High Similarity	NPC288694
0.8776	High Similarity	NPC7341
0.8776	High Similarity	NPC473200
0.8763	High Similarity	NPC243728
0.8763	High Similarity	NPC473890
0.8725	High Similarity	NPC80210
0.8725	High Similarity	NPC38376
0.8713	High Similarity	NPC242748
0.8713	High Similarity	NPC138057
0.87	High Similarity	NPC211879
0.87	High Similarity	NPC8039
0.87	High Similarity	NPC473198
0.87	High Similarity	NPC157659
0.87	High Similarity	NPC120123
0.87	High Similarity	NPC31907
0.87	High Similarity	NPC245280
0.87	High Similarity	NPC189852
0.87	High Similarity	NPC475701
0.87	High Similarity	NPC155010
0.87	High Similarity	NPC213190
0.87	High Similarity	NPC473020
0.87	High Similarity	NPC114874
0.87	High Similarity	NPC286969
0.87	High Similarity	NPC472252
0.87	High Similarity	NPC131479
0.87	High Similarity	NPC16520
0.8696	High Similarity	NPC237344
0.8687	High Similarity	NPC129372
0.8687	High Similarity	NPC4831
0.8687	High Similarity	NPC160734
0.8687	High Similarity	NPC472023
0.8687	High Similarity	NPC476132
0.8687	High Similarity	NPC309425
0.8687	High Similarity	NPC47566
0.8687	High Similarity	NPC88000
0.8673	High Similarity	NPC477876
0.8673	High Similarity	NPC158088
0.8673	High Similarity	NPC477875
0.8667	High Similarity	NPC144068
0.8641	High Similarity	NPC221110
0.8641	High Similarity	NPC180459
0.8641	High Similarity	NPC285253
0.8641	High Similarity	NPC195116
0.8627	High Similarity	NPC257964
0.8627	High Similarity	NPC181467
0.8627	High Similarity	NPC281939
0.8627	High Similarity	NPC473469
0.8627	High Similarity	NPC190395
0.8614	High Similarity	NPC474464
0.8614	High Similarity	NPC75608
0.86	High Similarity	NPC272015
0.8586	High Similarity	NPC474571
0.8586	High Similarity	NPC476195
0.8586	High Similarity	NPC254567
0.8586	High Similarity	NPC64348
0.8571	High Similarity	NPC116794
0.8558	High Similarity	NPC7870
0.8558	High Similarity	NPC199457
0.8558	High Similarity	NPC75747
0.8558	High Similarity	NPC110139
0.8558	High Similarity	NPC274507
0.8558	High Similarity	NPC68419
0.8558	High Similarity	NPC102914
0.8558	High Similarity	NPC108709
0.8544	High Similarity	NPC7213
0.8544	High Similarity	NPC476541
0.8544	High Similarity	NPC476538
0.8544	High Similarity	NPC476539
0.8544	High Similarity	NPC220427
0.8544	High Similarity	NPC476540
0.8544	High Similarity	NPC126147
0.8544	High Similarity	NPC180183
0.8544	High Similarity	NPC246124
0.8529	High Similarity	NPC269627
0.8529	High Similarity	NPC472899
0.8529	High Similarity	NPC474015
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	NPC473923
0.8529	High Similarity	NPC473476
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	NPC69737
0.8526	High Similarity	NPC159876
0.85	High Similarity	NPC96784
0.85	High Similarity	NPC235920
0.85	High Similarity	NPC470054
0.85	High Similarity	NPC267510
0.85	High Similarity	NPC470434
0.8491	Intermediate Similarity	NPC269315
0.8491	Intermediate Similarity	NPC271138
0.8485	Intermediate Similarity	NPC476895
0.8485	Intermediate Similarity	NPC477928
0.8485	Intermediate Similarity	NPC5358
0.8485	Intermediate Similarity	NPC216260
0.8478	Intermediate Similarity	NPC238992
0.8478	Intermediate Similarity	NPC319238
0.8476	Intermediate Similarity	NPC114188
0.8476	Intermediate Similarity	NPC157474
0.8476	Intermediate Similarity	NPC179434
0.8476	Intermediate Similarity	NPC297208
0.8476	Intermediate Similarity	NPC108748
0.8476	Intermediate Similarity	NPC30397
0.8476	Intermediate Similarity	NPC191763
0.8476	Intermediate Similarity	NPC110494
0.8476	Intermediate Similarity	NPC476547
0.8476	Intermediate Similarity	NPC211798
0.8476	Intermediate Similarity	NPC197231
0.8476	Intermediate Similarity	NPC473481
0.8476	Intermediate Similarity	NPC235841
0.8469	Intermediate Similarity	NPC207617
0.8462	Intermediate Similarity	NPC302057
0.8462	Intermediate Similarity	NPC306131
0.8462	Intermediate Similarity	NPC43976
0.8462	Intermediate Similarity	NPC51925
0.8462	Intermediate Similarity	NPC14630
0.8462	Intermediate Similarity	NPC237503
0.8462	Intermediate Similarity	NPC154085
0.8462	Intermediate Similarity	NPC250089
0.8462	Intermediate Similarity	NPC157530
0.8462	Intermediate Similarity	NPC477027
0.8462	Intermediate Similarity	NPC296761
0.8462	Intermediate Similarity	NPC204407
0.8462	Intermediate Similarity	NPC167383
0.8462	Intermediate Similarity	NPC57362
0.8462	Intermediate Similarity	NPC306746
0.8462	Intermediate Similarity	NPC477026
0.8462	Intermediate Similarity	NPC125361
0.8462	Intermediate Similarity	NPC127853
0.8462	Intermediate Similarity	NPC475670
0.8462	Intermediate Similarity	NPC70204
0.8447	Intermediate Similarity	NPC305423
0.8447	Intermediate Similarity	NPC14946
0.8447	Intermediate Similarity	NPC230507
0.8447	Intermediate Similarity	NPC161676
0.8447	Intermediate Similarity	NPC208650
0.8447	Intermediate Similarity	NPC283849
0.8447	Intermediate Similarity	NPC234160
0.8447	Intermediate Similarity	NPC470432
0.8447	Intermediate Similarity	NPC226642
0.8447	Intermediate Similarity	NPC113044
0.8447	Intermediate Similarity	NPC283829
0.8447	Intermediate Similarity	NPC231340
0.8447	Intermediate Similarity	NPC14704
0.8447	Intermediate Similarity	NPC63368
0.844	Intermediate Similarity	NPC470914
0.8431	Intermediate Similarity	NPC475365
0.8431	Intermediate Similarity	NPC471111
0.8431	Intermediate Similarity	NPC312774
0.8431	Intermediate Similarity	NPC93352
0.8421	Intermediate Similarity	NPC477917
0.8421	Intermediate Similarity	NPC473058

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 NPC473790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	2007
0.2-0.3	4222
0.3-0.4	1835
0.4-0.5	484
0.5-0.6	242
0.6-0.7	128
0.7-0.8	17
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7935	Intermediate Similarity	NPD7645	Phase 2
0.7778	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD8033	Approved
0.7611	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6412	Phase 2
0.7565	Intermediate Similarity	NPD8377	Approved
0.7565	Intermediate Similarity	NPD8294	Approved
0.7521	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7478	Intermediate Similarity	NPD7516	Approved
0.7391	Intermediate Similarity	NPD7328	Approved
0.7391	Intermediate Similarity	NPD7327	Approved
0.7292	Intermediate Similarity	NPD7525	Registered
0.7282	Intermediate Similarity	NPD8171	Discontinued
0.7212	Intermediate Similarity	NPD7748	Approved
0.7203	Intermediate Similarity	NPD7503	Approved
0.7193	Intermediate Similarity	NPD8133	Approved
0.717	Intermediate Similarity	NPD7902	Approved
0.7129	Intermediate Similarity	NPD7524	Approved
0.7054	Intermediate Similarity	NPD6686	Approved
0.7019	Intermediate Similarity	NPD7515	Phase 2
0.6992	Remote Similarity	NPD7736	Approved
0.6975	Remote Similarity	NPD6059	Approved
0.6975	Remote Similarity	NPD6054	Approved
0.6967	Remote Similarity	NPD7507	Approved
0.6947	Remote Similarity	NPD6942	Approved
0.6947	Remote Similarity	NPD7339	Approved
0.6944	Remote Similarity	NPD7638	Approved
0.6939	Remote Similarity	NPD6928	Phase 2
0.6905	Remote Similarity	NPD8449	Approved
0.6887	Remote Similarity	NPD7900	Approved
0.6887	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7639	Approved
0.6881	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6370	Approved
0.685	Remote Similarity	NPD8450	Suspended
0.6832	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7319	Approved
0.6789	Remote Similarity	NPD4225	Approved
0.6777	Remote Similarity	NPD8513	Phase 3
0.6777	Remote Similarity	NPD6016	Approved
0.6777	Remote Similarity	NPD8516	Approved
0.6777	Remote Similarity	NPD6015	Approved
0.6777	Remote Similarity	NPD8517	Approved
0.6777	Remote Similarity	NPD8515	Approved
0.6774	Remote Similarity	NPD8293	Discontinued
0.6762	Remote Similarity	NPD3168	Discontinued
0.6748	Remote Similarity	NPD7492	Approved
0.6733	Remote Similarity	NPD6695	Phase 3
0.6721	Remote Similarity	NPD5988	Approved
0.6698	Remote Similarity	NPD8035	Phase 2
0.6698	Remote Similarity	NPD8034	Phase 2
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6067	Discontinued
0.664	Remote Similarity	NPD7078	Approved
0.6637	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6399	Phase 3
0.6635	Remote Similarity	NPD7750	Discontinued
0.6583	Remote Similarity	NPD6009	Approved
0.6581	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6933	Approved
0.6525	Remote Similarity	NPD6882	Approved
0.6525	Remote Similarity	NPD8297	Approved
0.6518	Remote Similarity	NPD5344	Discontinued
0.6505	Remote Similarity	NPD4786	Approved
0.65	Remote Similarity	NPD6929	Approved
0.6476	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4632	Approved
0.6471	Remote Similarity	NPD3667	Approved
0.6466	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6033	Approved
0.6446	Remote Similarity	NPD7115	Discovery
0.6442	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6930	Phase 2
0.6436	Remote Similarity	NPD6931	Approved
0.6435	Remote Similarity	NPD6402	Approved
0.6435	Remote Similarity	NPD5739	Approved
0.6435	Remote Similarity	NPD7128	Approved
0.6435	Remote Similarity	NPD6675	Approved
0.6423	Remote Similarity	NPD6319	Approved
0.6381	Remote Similarity	NPD3618	Phase 1
0.6372	Remote Similarity	NPD4159	Approved
0.6356	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5328	Approved
0.6327	Remote Similarity	NPD6924	Approved
0.6327	Remote Similarity	NPD6926	Approved
0.6325	Remote Similarity	NPD6881	Approved
0.6325	Remote Similarity	NPD7320	Approved
0.6325	Remote Similarity	NPD6899	Approved
0.6316	Remote Similarity	NPD7632	Discontinued
0.6303	Remote Similarity	NPD8130	Phase 1
0.63	Remote Similarity	NPD5776	Phase 2
0.63	Remote Similarity	NPD6925	Approved
0.63	Remote Similarity	NPD6932	Approved
0.6293	Remote Similarity	NPD6008	Approved
0.6293	Remote Similarity	NPD5357	Phase 1
0.6275	Remote Similarity	NPD7509	Discontinued
0.6271	Remote Similarity	NPD6373	Approved
0.6271	Remote Similarity	NPD6372	Approved
0.6263	Remote Similarity	NPD8264	Approved
0.625	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4755	Approved
0.6239	Remote Similarity	NPD6079	Approved
0.6239	Remote Similarity	NPD7087	Discontinued
0.6239	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD6411	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD7145	Approved
0.6218	Remote Similarity	NPD4634	Approved
0.6218	Remote Similarity	NPD7290	Approved
0.6218	Remote Similarity	NPD6883	Approved
0.6218	Remote Similarity	NPD7102	Approved
0.6216	Remote Similarity	NPD7991	Discontinued
0.619	Remote Similarity	NPD5126	Approved
0.619	Remote Similarity	NPD5125	Phase 3
0.6186	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4202	Approved
0.6176	Remote Similarity	NPD6683	Phase 2
0.6167	Remote Similarity	NPD6650	Approved
0.6167	Remote Similarity	NPD6617	Approved
0.6167	Remote Similarity	NPD6649	Approved
0.6167	Remote Similarity	NPD6869	Approved
0.6167	Remote Similarity	NPD6847	Approved
0.6162	Remote Similarity	NPD1810	Approved
0.6162	Remote Similarity	NPD4785	Approved
0.6162	Remote Similarity	NPD4784	Approved
0.6162	Remote Similarity	NPD1811	Approved
0.6143	Remote Similarity	NPD7625	Phase 1
0.6142	Remote Similarity	NPD7604	Phase 2
0.614	Remote Similarity	NPD4700	Approved
0.614	Remote Similarity	NPD6648	Approved
0.614	Remote Similarity	NPD5285	Approved
0.614	Remote Similarity	NPD4696	Approved
0.614	Remote Similarity	NPD5286	Approved
0.6134	Remote Similarity	NPD6014	Approved
0.6134	Remote Similarity	NPD6012	Approved
0.6134	Remote Similarity	NPD6013	Approved
0.6132	Remote Similarity	NPD6893	Approved
0.6122	Remote Similarity	NPD4243	Approved
0.6122	Remote Similarity	NPD7151	Approved
0.6122	Remote Similarity	NPD7152	Approved
0.6122	Remote Similarity	NPD7150	Approved
0.6117	Remote Similarity	NPD4748	Discontinued
0.6117	Remote Similarity	NPD7514	Phase 3
0.6117	Remote Similarity	NPD7332	Phase 2
0.6111	Remote Similarity	NPD5983	Phase 2
0.6111	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6084	Phase 2
0.6106	Remote Similarity	NPD6083	Phase 2
0.6102	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7637	Suspended
0.6082	Remote Similarity	NPD6923	Approved
0.6082	Remote Similarity	NPD6922	Approved
0.6064	Remote Similarity	NPD371	Approved
0.6058	Remote Similarity	NPD6902	Approved
0.6058	Remote Similarity	NPD6898	Phase 1
0.6055	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6101	Approved
0.6053	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6011	Approved
0.6047	Remote Similarity	NPD6336	Discontinued
0.6038	Remote Similarity	NPD3668	Phase 3
0.6038	Remote Similarity	NPD3665	Phase 1
0.6038	Remote Similarity	NPD3666	Approved
0.6038	Remote Similarity	NPD3133	Approved
0.6034	Remote Similarity	NPD5224	Approved
0.6034	Remote Similarity	NPD5211	Phase 2
0.6034	Remote Similarity	NPD5226	Approved
0.6034	Remote Similarity	NPD4633	Approved
0.6034	Remote Similarity	NPD5225	Approved
0.6033	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7143	Approved
0.602	Remote Similarity	NPD7144	Approved
0.6018	Remote Similarity	NPD5222	Approved
0.6018	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5221	Approved
0.6018	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD7838	Discovery
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD46	Approved
0.5985	Remote Similarity	NPD5956	Approved
0.5983	Remote Similarity	NPD5174	Approved
0.5983	Remote Similarity	NPD5175	Approved
0.5965	Remote Similarity	NPD5173	Approved
0.5948	Remote Similarity	NPD5223	Approved
0.5932	Remote Similarity	NPD5141	Approved
0.5926	Remote Similarity	NPD7521	Approved
0.5926	Remote Similarity	NPD7146	Approved
0.5926	Remote Similarity	NPD6409	Approved
0.5926	Remote Similarity	NPD6684	Approved
0.5926	Remote Similarity	NPD7334	Approved
0.5926	Remote Similarity	NPD5330	Approved
0.5914	Remote Similarity	NPD1145	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