NPASS Compound

Structure

NPC212453 OpenBabel07101719252D 37 40 0 0 1 0 0 0 0 0999 V2000 5.0694 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3829 -5.9084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6579 -5.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 2.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 2.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4481 0.4035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8714 -3.6470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3300 -3.8235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2843 -4.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0285 -2.8956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7728 -0.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0694 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7728 -1.7649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3796 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5858 -4.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 1 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 -2.0742 -2.6928 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9143 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1464 -2.9942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8416 -6.0849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5401 -5.1570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 32 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 33 2 0 0 0 0 21 36 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 32 1 1 0 0 0 24 28 1 0 0 0 0 24 29 1 1 0 0 0 25 29 1 1 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 36 1 6 0 0 0 27 37 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 1 0 0 0 32 9 1 6 0 0 0 32 34 1 0 0 0 0 35 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.41
Volume:	569.117
LogP:	5.648
LogD:	5.113
LogS:	-5.08
# Rotatable Bonds:	8
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	4.906
Fsp3:	0.969
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.015
MDCK Permeability:	2.616836536617484e-05
Pgp-inhibitor:	0.853
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.745

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	94.5796127319336%
Volume Distribution (VD):	0.993
Pgp-substrate:	2.356285333633423%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.801
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.703
CYP3A4-inhibitor:	0.299
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	3.442
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.879
Carcinogencity:	0.018
Eye Corrosion:	0.996
Eye Irritation:	0.871
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC212453

Natural Product ID:	NPC212453
*Common Name:**	Aglaiabbreviatin F
IUPAC Name:	[(3R,5R,8R,9R,10R,13R,14R,17S)-17-[(2S)-6-hydroperoxy-2-hydroxy-6-methylheptan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:	Aglaiabbreviatin F
Standard InCHIKey:	PCHIVLNSEKZZQK-QFNQZFPKSA-N
Standard InCHI:	InChI=1S/C32H56O5/c1-21(33)36-26-15-18-29(6)24(28(26,4)5)14-20-31(8)25(29)12-11-22-23(13-19-30(22,31)7)32(9,34)17-10-16-27(2,3)37-35/h22-26,34-35H,10-20H2,1-9H3/t22-,23+,24+,25-,26-,29+,30-,31-,32+/m1/s1
SMILES:	CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC[C@@H]2[C@H](CC[C@@]32C)[C@](C)(CCCC(C)(C)OO)O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651319
PubChem CID:	50908450
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
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21087017]
NPO7602	Aglaia abbreviata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21087017]
NPO7602	Aglaia abbreviata	Species	Meliaceae	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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[504202]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	600.0	nM	PMID[504202]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	1400.0	nM	PMID[504202]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	460.0	nM	PMID[504202]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	310.0	nM	PMID[504202]
NPT2	Others	Unspecified		IC50	=	5500	nM	PMID[17253840]

☑ 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 NPC212453 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	355
0.1-0.2	3370
0.2-0.3	13542
0.3-0.4	10838
0.4-0.5	5381
0.5-0.6	4862
0.6-0.7	3445
0.7-0.8	781
0.8-0.85	85
0.85-0.9	32
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9459	High Similarity	NPC220379
0.9211	High Similarity	NPC73515
0.9211	High Similarity	NPC190940
0.92	High Similarity	NPC476176
0.9091	High Similarity	NPC477286
0.9091	High Similarity	NPC286719
0.9067	High Similarity	NPC471045
0.8974	High Similarity	NPC477285
0.8974	High Similarity	NPC111582
0.8919	High Similarity	NPC186851
0.8846	High Similarity	NPC202688
0.8846	High Similarity	NPC60018
0.8846	High Similarity	NPC154043
0.8701	High Similarity	NPC201276
0.8701	High Similarity	NPC80891
0.8701	High Similarity	NPC477287
0.8642	High Similarity	NPC215968
0.8642	High Similarity	NPC103782
0.8642	High Similarity	NPC114378
0.8642	High Similarity	NPC155531
0.8642	High Similarity	NPC477283
0.859	High Similarity	NPC474714
0.859	High Similarity	NPC261616
0.8571	High Similarity	NPC224802
0.8571	High Similarity	NPC80089
0.8571	High Similarity	NPC171426
0.8571	High Similarity	NPC324700
0.8571	High Similarity	NPC34046
0.8533	High Similarity	NPC74639
0.8533	High Similarity	NPC272359
0.8519	High Similarity	NPC266651
0.8514	High Similarity	NPC1340
0.8514	High Similarity	NPC252182
0.8514	High Similarity	NPC470071
0.8514	High Similarity	NPC187471
0.8493	Intermediate Similarity	NPC66407
0.8442	Intermediate Similarity	NPC171658
0.8434	Intermediate Similarity	NPC201607
0.8434	Intermediate Similarity	NPC56777
0.8395	Intermediate Similarity	NPC471044
0.8395	Intermediate Similarity	NPC473336
0.8378	Intermediate Similarity	NPC192192
0.8375	Intermediate Similarity	NPC477284
0.8354	Intermediate Similarity	NPC206735
0.8312	Intermediate Similarity	NPC4209
0.8267	Intermediate Similarity	NPC157422
0.8267	Intermediate Similarity	NPC127094
0.8267	Intermediate Similarity	NPC109457
0.8267	Intermediate Similarity	NPC100586
0.825	Intermediate Similarity	NPC58631
0.8243	Intermediate Similarity	NPC129829
0.8243	Intermediate Similarity	NPC254037
0.8219	Intermediate Similarity	NPC476928
0.8205	Intermediate Similarity	NPC133596
0.8205	Intermediate Similarity	NPC11907
0.8205	Intermediate Similarity	NPC207010
0.8205	Intermediate Similarity	NPC317913
0.8205	Intermediate Similarity	NPC64081
0.8205	Intermediate Similarity	NPC474574
0.8182	Intermediate Similarity	NPC231680
0.8182	Intermediate Similarity	NPC478105
0.8182	Intermediate Similarity	NPC212733
0.8182	Intermediate Similarity	NPC91387
0.8182	Intermediate Similarity	NPC270306
0.8171	Intermediate Similarity	NPC319909
0.8171	Intermediate Similarity	NPC299963
0.8158	Intermediate Similarity	NPC153719
0.8148	Intermediate Similarity	NPC289486
0.8148	Intermediate Similarity	NPC61107
0.8148	Intermediate Similarity	NPC472504
0.8148	Intermediate Similarity	NPC121121
0.814	Intermediate Similarity	NPC473066
0.8133	Intermediate Similarity	NPC63588
0.8133	Intermediate Similarity	NPC282454
0.8133	Intermediate Similarity	NPC232925
0.8133	Intermediate Similarity	NPC251201
0.8052	Intermediate Similarity	NPC167702
0.8052	Intermediate Similarity	NPC472945
0.8052	Intermediate Similarity	NPC304499
0.8052	Intermediate Similarity	NPC472944
0.8052	Intermediate Similarity	NPC280026
0.8049	Intermediate Similarity	NPC473742
0.8049	Intermediate Similarity	NPC5280
0.8026	Intermediate Similarity	NPC131506
0.8026	Intermediate Similarity	NPC195530
0.8026	Intermediate Similarity	NPC473279
0.8026	Intermediate Similarity	NPC469940
0.8026	Intermediate Similarity	NPC157777
0.8025	Intermediate Similarity	NPC12933
0.8023	Intermediate Similarity	NPC10274
0.8	Intermediate Similarity	NPC107919
0.8	Intermediate Similarity	NPC320144
0.8	Intermediate Similarity	NPC477820
0.8	Intermediate Similarity	NPC81074
0.8	Intermediate Similarity	NPC477282
0.7976	Intermediate Similarity	NPC168231
0.7976	Intermediate Similarity	NPC472272
0.7976	Intermediate Similarity	NPC131365
0.7975	Intermediate Similarity	NPC143133
0.7975	Intermediate Similarity	NPC476233
0.7975	Intermediate Similarity	NPC298168
0.7973	Intermediate Similarity	NPC48079
0.7955	Intermediate Similarity	NPC191915
0.7955	Intermediate Similarity	NPC151214
0.7949	Intermediate Similarity	NPC196136
0.7949	Intermediate Similarity	NPC243027
0.7949	Intermediate Similarity	NPC317242
0.7949	Intermediate Similarity	NPC158208
0.7931	Intermediate Similarity	NPC219516
0.7927	Intermediate Similarity	NPC2096
0.7927	Intermediate Similarity	NPC242771
0.7927	Intermediate Similarity	NPC311642
0.7927	Intermediate Similarity	NPC100366
0.7927	Intermediate Similarity	NPC164289
0.7927	Intermediate Similarity	NPC208912
0.7922	Intermediate Similarity	NPC473238
0.7922	Intermediate Similarity	NPC470610
0.7922	Intermediate Similarity	NPC472341
0.7917	Intermediate Similarity	NPC114891
0.7901	Intermediate Similarity	NPC472943
0.7901	Intermediate Similarity	NPC304194
0.7901	Intermediate Similarity	NPC477851
0.7901	Intermediate Similarity	NPC472951
0.7882	Intermediate Similarity	NPC5943
0.7875	Intermediate Similarity	NPC243594
0.7875	Intermediate Similarity	NPC329117
0.7875	Intermediate Similarity	NPC31031
0.7875	Intermediate Similarity	NPC471769
0.7875	Intermediate Similarity	NPC185465
0.7867	Intermediate Similarity	NPC472741
0.7865	Intermediate Similarity	NPC279974
0.7865	Intermediate Similarity	NPC57964
0.7865	Intermediate Similarity	NPC94582
0.7848	Intermediate Similarity	NPC163597
0.7841	Intermediate Similarity	NPC256104
0.7841	Intermediate Similarity	NPC182740
0.7841	Intermediate Similarity	NPC211845
0.7841	Intermediate Similarity	NPC122083
0.7838	Intermediate Similarity	NPC142712
0.7831	Intermediate Similarity	NPC213737
0.7831	Intermediate Similarity	NPC475820
0.7831	Intermediate Similarity	NPC474284
0.7831	Intermediate Similarity	NPC474346
0.7831	Intermediate Similarity	NPC474253
0.7831	Intermediate Similarity	NPC470070
0.7821	Intermediate Similarity	NPC228994
0.7821	Intermediate Similarity	NPC192501
0.7821	Intermediate Similarity	NPC48795
0.7821	Intermediate Similarity	NPC10476
0.7821	Intermediate Similarity	NPC477508
0.7816	Intermediate Similarity	NPC77756
0.7805	Intermediate Similarity	NPC470154
0.7792	Intermediate Similarity	NPC127283
0.7792	Intermediate Similarity	NPC8004
0.7791	Intermediate Similarity	NPC160304
0.7791	Intermediate Similarity	NPC4309
0.7778	Intermediate Similarity	NPC238796
0.7778	Intermediate Similarity	NPC218585
0.7778	Intermediate Similarity	NPC47808
0.7778	Intermediate Similarity	NPC156377
0.7778	Intermediate Similarity	NPC252056
0.7778	Intermediate Similarity	NPC237071
0.7778	Intermediate Similarity	NPC71460
0.7778	Intermediate Similarity	NPC148174
0.7778	Intermediate Similarity	NPC203434
0.7778	Intermediate Similarity	NPC305835
0.7765	Intermediate Similarity	NPC80700
0.7765	Intermediate Similarity	NPC171698
0.7765	Intermediate Similarity	NPC321340
0.7765	Intermediate Similarity	NPC302111
0.7765	Intermediate Similarity	NPC119633
0.7765	Intermediate Similarity	NPC270957
0.7763	Intermediate Similarity	NPC196197
0.7763	Intermediate Similarity	NPC299948
0.7763	Intermediate Similarity	NPC470830
0.7763	Intermediate Similarity	NPC241085
0.775	Intermediate Similarity	NPC302578
0.775	Intermediate Similarity	NPC474404
0.775	Intermediate Similarity	NPC105208
0.775	Intermediate Similarity	NPC185915
0.775	Intermediate Similarity	NPC477227
0.775	Intermediate Similarity	NPC128951
0.775	Intermediate Similarity	NPC192046
0.775	Intermediate Similarity	NPC477918
0.775	Intermediate Similarity	NPC471151
0.7738	Intermediate Similarity	NPC473299
0.7733	Intermediate Similarity	NPC475884
0.7733	Intermediate Similarity	NPC473230
0.7727	Intermediate Similarity	NPC52756
0.7722	Intermediate Similarity	NPC477934
0.7711	Intermediate Similarity	NPC475388
0.7711	Intermediate Similarity	NPC13494
0.7711	Intermediate Similarity	NPC477447
0.7711	Intermediate Similarity	NPC296734
0.7711	Intermediate Similarity	NPC268040
0.7711	Intermediate Similarity	NPC470155
0.7711	Intermediate Similarity	NPC477446
0.7711	Intermediate Similarity	NPC102156
0.7711	Intermediate Similarity	NPC30583
0.7711	Intermediate Similarity	NPC470611

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 NPC212453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	3624
0.2-0.3	3568
0.3-0.4	984
0.4-0.5	262
0.5-0.6	210
0.6-0.7	110
0.7-0.8	25
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD6115	Approved
0.8571	High Similarity	NPD6118	Approved
0.8571	High Similarity	NPD6114	Approved
0.8571	High Similarity	NPD6697	Approved
0.8312	Intermediate Similarity	NPD6117	Approved
0.8205	Intermediate Similarity	NPD6116	Phase 1
0.8052	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8035	Phase 2
0.7528	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD3702	Approved
0.75	Intermediate Similarity	NPD3703	Phase 2
0.747	Intermediate Similarity	NPD6928	Phase 2
0.7436	Intermediate Similarity	NPD4787	Phase 1
0.7403	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5360	Phase 3
0.7342	Intermediate Similarity	NPD6081	Approved
0.7342	Intermediate Similarity	NPD5777	Approved
0.7308	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4224	Phase 2
0.7059	Intermediate Similarity	NPD7525	Registered
0.7053	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD4789	Approved
0.7	Intermediate Similarity	NPD4245	Approved
0.6979	Remote Similarity	NPD8418	Phase 2
0.6979	Remote Similarity	NPD7639	Approved
0.6979	Remote Similarity	NPD7640	Approved
0.6914	Remote Similarity	NPD4758	Discontinued
0.6882	Remote Similarity	NPD8171	Discontinued
0.6875	Remote Similarity	NPD3698	Phase 2
0.6837	Remote Similarity	NPD7632	Discontinued
0.6824	Remote Similarity	NPD5364	Discontinued
0.6795	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6399	Phase 3
0.6632	Remote Similarity	NPD7748	Approved
0.6629	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3669	Approved
0.6628	Remote Similarity	NPD3671	Phase 1
0.6593	Remote Similarity	NPD8308	Discontinued
0.6562	Remote Similarity	NPD7991	Discontinued
0.6535	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6700	Approved
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD7902	Approved
0.6421	Remote Similarity	NPD6702	Approved
0.6421	Remote Similarity	NPD6703	Approved
0.6383	Remote Similarity	NPD6051	Approved
0.6355	Remote Similarity	NPD8133	Approved
0.6353	Remote Similarity	NPD1810	Approved
0.6353	Remote Similarity	NPD1811	Approved
0.6346	Remote Similarity	NPD6881	Approved
0.6346	Remote Similarity	NPD6899	Approved
0.6346	Remote Similarity	NPD7320	Approved
0.6321	Remote Similarity	NPD8130	Phase 1
0.6306	Remote Similarity	NPD8294	Approved
0.6306	Remote Similarity	NPD8377	Approved
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6279	Remote Similarity	NPD6942	Approved
0.6279	Remote Similarity	NPD7339	Approved
0.6273	Remote Similarity	NPD7328	Approved
0.6273	Remote Similarity	NPD7327	Approved
0.6264	Remote Similarity	NPD6695	Phase 3
0.6264	Remote Similarity	NPD4788	Approved
0.6263	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD6084	Phase 2
0.6262	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD8335	Approved
0.625	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD371	Approved
0.6238	Remote Similarity	NPD1700	Approved
0.6226	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD6883	Approved
0.6226	Remote Similarity	NPD7102	Approved
0.6216	Remote Similarity	NPD7516	Approved
0.6211	Remote Similarity	NPD5328	Approved
0.6196	Remote Similarity	NPD4786	Approved
0.6196	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2254	Approved
0.619	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD2686	Approved
0.619	Remote Similarity	NPD2687	Approved
0.618	Remote Similarity	NPD7645	Phase 2
0.617	Remote Similarity	NPD7750	Discontinued
0.6168	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6650	Approved
0.6168	Remote Similarity	NPD6649	Approved
0.6168	Remote Similarity	NPD6869	Approved
0.6168	Remote Similarity	NPD6847	Approved
0.6168	Remote Similarity	NPD6617	Approved
0.6154	Remote Similarity	NPD6008	Approved
0.6145	Remote Similarity	NPD6705	Phase 1
0.6132	Remote Similarity	NPD6013	Approved
0.6132	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD6014	Approved
0.6122	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7900	Approved
0.6111	Remote Similarity	NPD6882	Approved
0.6111	Remote Similarity	NPD4748	Discontinued
0.6105	Remote Similarity	NPD6672	Approved
0.6105	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5737	Approved
0.6095	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6940	Discontinued
0.6082	Remote Similarity	NPD7637	Suspended
0.6082	Remote Similarity	NPD6079	Approved
0.6067	Remote Similarity	NPD4802	Phase 2
0.6067	Remote Similarity	NPD4238	Approved
0.6064	Remote Similarity	NPD7146	Approved
0.6064	Remote Similarity	NPD6684	Approved
0.6064	Remote Similarity	NPD5330	Approved
0.6064	Remote Similarity	NPD7521	Approved
0.6064	Remote Similarity	NPD6409	Approved
0.6064	Remote Similarity	NPD3618	Phase 1
0.6064	Remote Similarity	NPD7334	Approved
0.6061	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5695	Phase 3
0.6055	Remote Similarity	NPD4632	Approved
0.6055	Remote Similarity	NPD8298	Phase 2
0.6044	Remote Similarity	NPD1779	Approved
0.6044	Remote Similarity	NPD1780	Approved
0.604	Remote Similarity	NPD5696	Approved
0.6038	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD6920	Discontinued
0.5981	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3667	Approved
0.5977	Remote Similarity	NPD6926	Approved
0.5977	Remote Similarity	NPD6924	Approved
0.5962	Remote Similarity	NPD7987	Approved
0.5962	Remote Similarity	NPD7911	Approved
0.5962	Remote Similarity	NPD7912	Approved
0.5962	Remote Similarity	NPD7986	Approved
0.5955	Remote Similarity	NPD8143	Approved
0.5955	Remote Similarity	NPD8144	Approved
0.5949	Remote Similarity	NPD3198	Approved
0.5941	Remote Similarity	NPD7920	Phase 3
0.5941	Remote Similarity	NPD4755	Approved
0.5941	Remote Similarity	NPD7919	Phase 3
0.5938	Remote Similarity	NPD6903	Approved
0.5934	Remote Similarity	NPD6931	Approved
0.5934	Remote Similarity	NPD6930	Phase 2
0.5932	Remote Similarity	NPD7736	Approved
0.593	Remote Similarity	NPD4243	Approved
0.5926	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD386	Approved
0.5915	Remote Similarity	NPD388	Approved
0.5897	Remote Similarity	NPD7507	Approved
0.5895	Remote Similarity	NPD6098	Approved
0.5893	Remote Similarity	NPD6009	Approved
0.5893	Remote Similarity	NPD7115	Discovery
0.5882	Remote Similarity	NPD8088	Phase 1
0.5877	Remote Similarity	NPD6319	Approved
0.5876	Remote Similarity	NPD6904	Approved
0.5876	Remote Similarity	NPD6080	Approved
0.5876	Remote Similarity	NPD6673	Approved
0.5862	Remote Similarity	NPD7604	Phase 2
0.5849	Remote Similarity	NPD8040	Discontinued
0.5847	Remote Similarity	NPD8293	Discontinued
0.5843	Remote Similarity	NPD6933	Approved
0.5842	Remote Similarity	NPD5222	Approved
0.5842	Remote Similarity	NPD4697	Phase 3
0.5842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5221	Approved
0.5841	Remote Similarity	NPD6335	Approved
0.5833	Remote Similarity	NPD384	Approved
0.5833	Remote Similarity	NPD385	Approved
0.5826	Remote Similarity	NPD5983	Phase 2
0.5826	Remote Similarity	NPD7503	Approved
0.5825	Remote Similarity	NPD4696	Approved
0.5825	Remote Similarity	NPD5286	Approved
0.5825	Remote Similarity	NPD4700	Approved
0.5825	Remote Similarity	NPD5285	Approved
0.5824	Remote Similarity	NPD6929	Approved
0.5824	Remote Similarity	NPD4195	Approved
0.5812	Remote Similarity	NPD7492	Approved
0.5804	Remote Similarity	NPD7755	Approved
0.5804	Remote Similarity	NPD6274	Approved
0.5804	Remote Similarity	NPD7754	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