NPASS Compound

Structure

NPC177141 OpenBabel07101718292D 35 38 0 0 1 0 0 0 0 0999 V2000 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -4.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4106 -5.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5417 -4.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7633 -5.8212 0.0000 C 0 0 0 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 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5636 -3.8305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0724 -6.7722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 -5.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2109 -3.2953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 3 20 1 0 0 0 0 6 34 1 0 0 0 0 7 12 1 0 0 0 0 7 18 2 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 28 1 0 0 0 0 19 2 1 1 0 0 0 19 24 1 0 0 0 0 19 27 1 0 0 0 0 20 31 2 0 0 0 0 20 35 1 0 0 0 0 21 29 1 0 0 0 0 22 32 2 0 0 0 0 23 9 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 1 0 0 0 25 30 1 1 0 0 0 26 29 1 1 0 0 0 27 12 1 6 0 0 0 27 35 1 0 0 0 0 28 33 2 0 0 0 0 28 34 1 0 0 0 0 29 4 1 1 0 0 0 30 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.3
Volume:	521.343
LogP:	5.533
LogD:	4.447
LogS:	-4.837
# Rotatable Bonds:	8
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.264
Synthetic Accessibility Score:	4.843
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.672
MDCK Permeability:	3.7787132896482944e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.871
30% Bioavailability (F30%):	0.54

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	87.47406005859375%
Volume Distribution (VD):	1.773
Pgp-substrate:	4.844778060913086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.162
CYP1A2-substrate:	0.219
CYP2C19-inhibitor:	0.837
CYP2C19-substrate:	0.611
CYP2C9-inhibitor:	0.858
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.673
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.688

ADMET: Excretion

Clearance (CL):	8.385
Half-life (T1/2):	0.333

ADMET: Toxicity

hERG Blockers:	0.389
Human Hepatotoxicity (H-HT):	0.539
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.869
Maximum Recommended Daily Dose:	0.88
Skin Sensitization:	0.981
Carcinogencity:	0.737
Eye Corrosion:	0.529
Eye Irritation:	0.094
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC177141

Natural Product ID:	NPC177141
*Common Name:**	Methyl (22R,24E)-22-Acetoxy-3-Oxocholesta-1,4,24-Trien-26-Oate
IUPAC Name:	methyl (E,5R,6S)-5-acetyloxy-6-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoate
Synonyms:
Standard InCHIKey:	CJXWFEZBFQONFN-YZOWWEOWSA-N
Standard InCHI:	InChI=1S/C30H42O5/c1-18(28(33)34-6)7-12-27(35-20(3)31)19(2)24-10-11-25-23-9-8-21-17-22(32)13-15-29(21,4)26(23)14-16-30(24,25)5/h7,13,15,17,19,23-27H,8-12,14,16H2,1-6H3/b18-7+/t19-,23-,24+,25-,26-,27+,29-,30+/m0/s1
SMILES:	COC(=O)/C(=C/C[C@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)C)OC(=O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480110
PubChem CID:	11340649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols 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
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[16038562]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	18400.0	nM	PMID[464226]

☑ 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 NPC177141 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	195
0.1-0.2	1089
0.2-0.3	4524
0.3-0.4	13419
0.4-0.5	8888
0.5-0.6	7186
0.6-0.7	5353
0.7-0.8	1880
0.8-0.85	140
0.85-0.9	20
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9647	High Similarity	NPC273199
0.9432	High Similarity	NPC281134
0.9	High Similarity	NPC33473
0.8925	High Similarity	NPC310981
0.8795	High Similarity	NPC190211
0.871	High Similarity	NPC98868
0.8681	High Similarity	NPC120351
0.8681	High Similarity	NPC471994
0.8681	High Similarity	NPC166143
0.8675	High Similarity	NPC105197
0.8667	High Similarity	NPC177641
0.8571	High Similarity	NPC44083
0.8571	High Similarity	NPC153987
0.8571	High Similarity	NPC38232
0.8556	High Similarity	NPC302280
0.8523	High Similarity	NPC286153
0.8488	Intermediate Similarity	NPC471218
0.8469	Intermediate Similarity	NPC475294
0.8462	Intermediate Similarity	NPC234335
0.8462	Intermediate Similarity	NPC218301
0.8454	Intermediate Similarity	NPC189616
0.8444	Intermediate Similarity	NPC474844
0.8444	Intermediate Similarity	NPC146554
0.8434	Intermediate Similarity	NPC474463
0.8409	Intermediate Similarity	NPC189311
0.8409	Intermediate Similarity	NPC474013
0.8404	Intermediate Similarity	NPC202705
0.8404	Intermediate Similarity	NPC110937
0.8391	Intermediate Similarity	NPC470046
0.8391	Intermediate Similarity	NPC470047
0.8387	Intermediate Similarity	NPC474909
0.837	Intermediate Similarity	NPC229976
0.8351	Intermediate Similarity	NPC297617
0.8333	Intermediate Similarity	NPC473879
0.8333	Intermediate Similarity	NPC168319
0.8333	Intermediate Similarity	NPC194028
0.8316	Intermediate Similarity	NPC176845
0.8316	Intermediate Similarity	NPC252295
0.8315	Intermediate Similarity	NPC470050
0.8315	Intermediate Similarity	NPC470051
0.8315	Intermediate Similarity	NPC195640
0.8315	Intermediate Similarity	NPC220478
0.8315	Intermediate Similarity	NPC264127
0.8298	Intermediate Similarity	NPC111684
0.8298	Intermediate Similarity	NPC58052
0.8295	Intermediate Similarity	NPC33913
0.8283	Intermediate Similarity	NPC91034
0.828	Intermediate Similarity	NPC304968
0.828	Intermediate Similarity	NPC128488
0.8276	Intermediate Similarity	NPC100297
0.8261	Intermediate Similarity	NPC190442
0.8242	Intermediate Similarity	NPC472240
0.8242	Intermediate Similarity	NPC262858
0.8242	Intermediate Similarity	NPC285982
0.8242	Intermediate Similarity	NPC284561
0.8229	Intermediate Similarity	NPC227865
0.8211	Intermediate Similarity	NPC2049
0.8211	Intermediate Similarity	NPC151488
0.8211	Intermediate Similarity	NPC253826
0.8211	Intermediate Similarity	NPC38530
0.8211	Intermediate Similarity	NPC141401
0.8211	Intermediate Similarity	NPC84335
0.8202	Intermediate Similarity	NPC323765
0.82	Intermediate Similarity	NPC220155
0.8191	Intermediate Similarity	NPC171395
0.8191	Intermediate Similarity	NPC293052
0.8182	Intermediate Similarity	NPC127790
0.8182	Intermediate Similarity	NPC193198
0.8182	Intermediate Similarity	NPC12283
0.8182	Intermediate Similarity	NPC474193
0.8172	Intermediate Similarity	NPC79117
0.8163	Intermediate Similarity	NPC470954
0.8152	Intermediate Similarity	NPC469595
0.8152	Intermediate Similarity	NPC475965
0.8152	Intermediate Similarity	NPC220454
0.8152	Intermediate Similarity	NPC212679
0.8152	Intermediate Similarity	NPC474842
0.8144	Intermediate Similarity	NPC99411
0.8144	Intermediate Similarity	NPC298233
0.8137	Intermediate Similarity	NPC474315
0.8132	Intermediate Similarity	NPC97884
0.8132	Intermediate Similarity	NPC226863
0.8132	Intermediate Similarity	NPC215831
0.8132	Intermediate Similarity	NPC472220
0.8125	Intermediate Similarity	NPC57079
0.8125	Intermediate Similarity	NPC218107
0.8125	Intermediate Similarity	NPC108368
0.8125	Intermediate Similarity	NPC92275
0.8111	Intermediate Similarity	NPC474970
0.8105	Intermediate Similarity	NPC190713
0.8105	Intermediate Similarity	NPC322063
0.8105	Intermediate Similarity	NPC307164
0.809	Intermediate Similarity	NPC472265
0.809	Intermediate Similarity	NPC318515
0.809	Intermediate Similarity	NPC96055
0.8085	Intermediate Similarity	NPC477129
0.8085	Intermediate Similarity	NPC201725
0.8085	Intermediate Similarity	NPC119562
0.8085	Intermediate Similarity	NPC477130
0.8085	Intermediate Similarity	NPC294266
0.8085	Intermediate Similarity	NPC476186
0.8085	Intermediate Similarity	NPC279410
0.8068	Intermediate Similarity	NPC321289
0.8068	Intermediate Similarity	NPC200513
0.8068	Intermediate Similarity	NPC327969
0.8061	Intermediate Similarity	NPC308351
0.8061	Intermediate Similarity	NPC475320
0.8061	Intermediate Similarity	NPC471993
0.8061	Intermediate Similarity	NPC155332
0.8061	Intermediate Similarity	NPC271266
0.8061	Intermediate Similarity	NPC32577
0.8061	Intermediate Similarity	NPC114540
0.8058	Intermediate Similarity	NPC475524
0.8058	Intermediate Similarity	NPC100267
0.8046	Intermediate Similarity	NPC233332
0.8043	Intermediate Similarity	NPC473647
0.8043	Intermediate Similarity	NPC262043
0.8043	Intermediate Similarity	NPC73995
0.8043	Intermediate Similarity	NPC5509
0.8043	Intermediate Similarity	NPC293044
0.8041	Intermediate Similarity	NPC201406
0.8041	Intermediate Similarity	NPC290802
0.8041	Intermediate Similarity	NPC470906
0.8039	Intermediate Similarity	NPC37116
0.8039	Intermediate Similarity	NPC473627
0.8023	Intermediate Similarity	NPC184737
0.8022	Intermediate Similarity	NPC477228
0.8021	Intermediate Similarity	NPC108078
0.8021	Intermediate Similarity	NPC99726
0.8021	Intermediate Similarity	NPC292133
0.8	Intermediate Similarity	NPC472442
0.8	Intermediate Similarity	NPC266570
0.8	Intermediate Similarity	NPC470048
0.8	Intermediate Similarity	NPC189863
0.8	Intermediate Similarity	NPC29447
0.8	Intermediate Similarity	NPC476174
0.8	Intermediate Similarity	NPC470223
0.7981	Intermediate Similarity	NPC122056
0.798	Intermediate Similarity	NPC112009
0.798	Intermediate Similarity	NPC180204
0.7979	Intermediate Similarity	NPC152778
0.7979	Intermediate Similarity	NPC476304
0.7979	Intermediate Similarity	NPC205034
0.7979	Intermediate Similarity	NPC475657
0.7979	Intermediate Similarity	NPC162615
0.7979	Intermediate Similarity	NPC214697
0.7979	Intermediate Similarity	NPC474736
0.7978	Intermediate Similarity	NPC22611
0.7978	Intermediate Similarity	NPC477124
0.7978	Intermediate Similarity	NPC472440
0.7978	Intermediate Similarity	NPC474976
0.7978	Intermediate Similarity	NPC474790
0.7961	Intermediate Similarity	NPC470960
0.7959	Intermediate Similarity	NPC224720
0.7959	Intermediate Similarity	NPC476240
0.7959	Intermediate Similarity	NPC476223
0.7957	Intermediate Similarity	NPC310479
0.7957	Intermediate Similarity	NPC159748
0.7957	Intermediate Similarity	NPC182136
0.7957	Intermediate Similarity	NPC161638
0.7957	Intermediate Similarity	NPC469372
0.7957	Intermediate Similarity	NPC101651
0.7957	Intermediate Similarity	NPC221111
0.7957	Intermediate Similarity	NPC280149
0.7957	Intermediate Similarity	NPC78973
0.7957	Intermediate Similarity	NPC8062
0.7955	Intermediate Similarity	NPC25554
0.7955	Intermediate Similarity	NPC474683
0.7955	Intermediate Similarity	NPC474752
0.7955	Intermediate Similarity	NPC82986
0.7955	Intermediate Similarity	NPC474759
0.7955	Intermediate Similarity	NPC474731
0.7955	Intermediate Similarity	NPC7505
0.7938	Intermediate Similarity	NPC166745
0.7938	Intermediate Similarity	NPC235464
0.7938	Intermediate Similarity	NPC197386
0.7935	Intermediate Similarity	NPC28227
0.7935	Intermediate Similarity	NPC93411
0.7935	Intermediate Similarity	NPC470613
0.7935	Intermediate Similarity	NPC477128
0.7935	Intermediate Similarity	NPC472302
0.7935	Intermediate Similarity	NPC470612
0.7931	Intermediate Similarity	NPC242767
0.7921	Intermediate Similarity	NPC476958
0.7917	Intermediate Similarity	NPC328371
0.7917	Intermediate Similarity	NPC472941
0.7917	Intermediate Similarity	NPC456
0.7917	Intermediate Similarity	NPC16967
0.7917	Intermediate Similarity	NPC88009
0.7912	Intermediate Similarity	NPC472863
0.7907	Intermediate Similarity	NPC189206
0.7905	Intermediate Similarity	NPC67259
0.7905	Intermediate Similarity	NPC147912
0.79	Intermediate Similarity	NPC472868
0.79	Intermediate Similarity	NPC235889
0.79	Intermediate Similarity	NPC272632
0.79	Intermediate Similarity	NPC165969
0.7895	Intermediate Similarity	NPC104925
0.7895	Intermediate Similarity	NPC470697
0.7895	Intermediate Similarity	NPC476415

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 NPC177141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1208
0.2-0.3	3952
0.3-0.4	2626
0.4-0.5	722
0.5-0.6	186
0.6-0.7	185
0.7-0.8	97
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8444	Intermediate Similarity	NPD6051	Approved
0.8333	Intermediate Similarity	NPD5737	Approved
0.8333	Intermediate Similarity	NPD6672	Approved
0.8315	Intermediate Similarity	NPD6409	Approved
0.8315	Intermediate Similarity	NPD7146	Approved
0.8315	Intermediate Similarity	NPD5330	Approved
0.8315	Intermediate Similarity	NPD7334	Approved
0.8315	Intermediate Similarity	NPD6684	Approved
0.8315	Intermediate Similarity	NPD7521	Approved
0.8132	Intermediate Similarity	NPD6903	Approved
0.8132	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD5693	Phase 1
0.7979	Intermediate Similarity	NPD6399	Phase 3
0.7938	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD7639	Approved
0.7857	Intermediate Similarity	NPD7640	Approved
0.7849	Intermediate Similarity	NPD6673	Approved
0.7849	Intermediate Similarity	NPD6080	Approved
0.7849	Intermediate Similarity	NPD6904	Approved
0.7802	Intermediate Similarity	NPD1694	Approved
0.7757	Intermediate Similarity	NPD7115	Discovery
0.7653	Intermediate Similarity	NPD6083	Phase 2
0.7653	Intermediate Similarity	NPD6084	Phase 2
0.7629	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5208	Approved
0.7528	Intermediate Similarity	NPD4195	Approved
0.7527	Intermediate Similarity	NPD6098	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD6050	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD5694	Approved
0.7449	Intermediate Similarity	NPD5695	Phase 3
0.7404	Intermediate Similarity	NPD5697	Approved
0.74	Intermediate Similarity	NPD5696	Approved
0.74	Intermediate Similarity	NPD4225	Approved
0.7396	Intermediate Similarity	NPD5692	Phase 3
0.7396	Intermediate Similarity	NPD5207	Approved
0.7358	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD7102	Approved
0.7358	Intermediate Similarity	NPD7290	Approved
0.7347	Intermediate Similarity	NPD7748	Approved
0.7347	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6011	Approved
0.732	Intermediate Similarity	NPD7637	Suspended
0.7312	Intermediate Similarity	NPD3133	Approved
0.7312	Intermediate Similarity	NPD3665	Phase 1
0.7312	Intermediate Similarity	NPD3666	Approved
0.7312	Intermediate Similarity	NPD3668	Phase 3
0.7308	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD6008	Approved
0.7308	Intermediate Similarity	NPD7128	Approved
0.7308	Intermediate Similarity	NPD6402	Approved
0.7308	Intermediate Similarity	NPD5739	Approved
0.7292	Intermediate Similarity	NPD5328	Approved
0.729	Intermediate Similarity	NPD6869	Approved
0.729	Intermediate Similarity	NPD6650	Approved
0.729	Intermediate Similarity	NPD6649	Approved
0.729	Intermediate Similarity	NPD6617	Approved
0.729	Intermediate Similarity	NPD6847	Approved
0.729	Intermediate Similarity	NPD8130	Phase 1
0.7283	Intermediate Similarity	NPD3667	Approved
0.7273	Intermediate Similarity	NPD6942	Approved
0.7273	Intermediate Similarity	NPD7339	Approved
0.7264	Intermediate Similarity	NPD6012	Approved
0.7264	Intermediate Similarity	NPD6014	Approved
0.7264	Intermediate Similarity	NPD6013	Approved
0.7263	Intermediate Similarity	NPD3573	Approved
0.7222	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6882	Approved
0.7216	Intermediate Similarity	NPD5785	Approved
0.72	Intermediate Similarity	NPD5222	Approved
0.72	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5221	Approved
0.7184	Intermediate Similarity	NPD7632	Discontinued
0.7172	Intermediate Similarity	NPD6001	Approved
0.717	Intermediate Similarity	NPD7320	Approved
0.7158	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.7129	Intermediate Similarity	NPD7902	Approved
0.7129	Intermediate Similarity	NPD5173	Approved
0.7113	Intermediate Similarity	NPD4753	Phase 2
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD6373	Approved
0.71	Intermediate Similarity	NPD4629	Approved
0.71	Intermediate Similarity	NPD5210	Approved
0.7097	Intermediate Similarity	NPD4221	Approved
0.7097	Intermediate Similarity	NPD4223	Phase 3
0.7097	Intermediate Similarity	NPD5209	Approved
0.7075	Intermediate Similarity	NPD6614	Approved
0.7075	Intermediate Similarity	NPD5701	Approved
0.7053	Intermediate Similarity	NPD5329	Approved
0.7027	Intermediate Similarity	NPD6868	Approved
0.7019	Intermediate Similarity	NPD5211	Phase 2
0.7018	Intermediate Similarity	NPD7503	Approved
0.7011	Intermediate Similarity	NPD4691	Approved
0.7011	Intermediate Similarity	NPD4747	Approved
0.7009	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5286	Approved
0.699	Remote Similarity	NPD5285	Approved
0.699	Remote Similarity	NPD4696	Approved
0.6979	Remote Similarity	NPD5279	Phase 3
0.6979	Remote Similarity	NPD5690	Phase 2
0.6972	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4058	Approved
0.6966	Remote Similarity	NPD4784	Approved
0.6966	Remote Similarity	NPD4785	Approved
0.6952	Remote Similarity	NPD6052	Approved
0.6947	Remote Similarity	NPD4197	Approved
0.6947	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5654	Approved
0.6923	Remote Similarity	NPD5223	Approved
0.6909	Remote Similarity	NPD6053	Discontinued
0.6903	Remote Similarity	NPD6335	Approved
0.69	Remote Similarity	NPD4202	Approved
0.6897	Remote Similarity	NPD4137	Phase 3
0.6889	Remote Similarity	NPD8039	Approved
0.6887	Remote Similarity	NPD5141	Approved
0.6882	Remote Similarity	NPD7525	Registered
0.6882	Remote Similarity	NPD4695	Discontinued
0.6863	Remote Similarity	NPD4697	Phase 3
0.6857	Remote Similarity	NPD4633	Approved
0.6857	Remote Similarity	NPD5226	Approved
0.6857	Remote Similarity	NPD5225	Approved
0.6857	Remote Similarity	NPD5224	Approved
0.6848	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4632	Approved
0.6842	Remote Similarity	NPD7100	Approved
0.6842	Remote Similarity	NPD7101	Approved
0.6842	Remote Similarity	NPD6695	Phase 3
0.6814	Remote Similarity	NPD6317	Approved
0.6804	Remote Similarity	NPD4138	Approved
0.6804	Remote Similarity	NPD5205	Approved
0.6804	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4688	Approved
0.6804	Remote Similarity	NPD4689	Approved
0.6804	Remote Similarity	NPD4623	Approved
0.6804	Remote Similarity	NPD4519	Discontinued
0.6804	Remote Similarity	NPD4690	Approved
0.6804	Remote Similarity	NPD4693	Phase 3
0.68	Remote Similarity	NPD8035	Phase 2
0.68	Remote Similarity	NPD8034	Phase 2
0.6796	Remote Similarity	NPD5959	Approved
0.6796	Remote Similarity	NPD4755	Approved
0.6792	Remote Similarity	NPD5174	Approved
0.6792	Remote Similarity	NPD5175	Approved
0.6778	Remote Similarity	NPD4687	Approved
0.6778	Remote Similarity	NPD6926	Approved
0.6778	Remote Similarity	NPD5733	Approved
0.6778	Remote Similarity	NPD6924	Approved
0.6771	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD7327	Approved
0.6754	Remote Similarity	NPD6314	Approved
0.6754	Remote Similarity	NPD7328	Approved
0.6754	Remote Similarity	NPD6313	Approved
0.6742	Remote Similarity	NPD4243	Approved
0.6735	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6274	Approved
0.6724	Remote Similarity	NPD8033	Approved
0.6706	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5363	Approved
0.6701	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7732	Phase 3
0.6696	Remote Similarity	NPD7094	Approved
0.6696	Remote Similarity	NPD6858	Approved
0.6696	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6638	Remote Similarity	NPD8377	Approved
0.6638	Remote Similarity	NPD8294	Approved
0.6638	Remote Similarity	NPD6319	Approved
0.6634	Remote Similarity	NPD6411	Approved
0.6633	Remote Similarity	NPD5280	Approved
0.6633	Remote Similarity	NPD4694	Approved
0.663	Remote Similarity	NPD6933	Approved
0.6629	Remote Similarity	NPD7144	Approved
0.6629	Remote Similarity	NPD7143	Approved
0.6628	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7604	Phase 2
0.6606	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6929	Approved
0.6581	Remote Similarity	NPD8379	Approved
0.6581	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8335	Approved
0.6581	Remote Similarity	NPD5983	Phase 2
0.6581	Remote Similarity	NPD8378	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