NPASS Compound

Structure

NPC242692 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7023 4.4680 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 3.0574 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3641 5.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0769 4.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 5.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7242 4.2601 0.0000 C 0 0 1 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 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -0.8660 1.5000 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0550 5.0032 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 7 32 1 0 0 0 0 8 32 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 29 1 0 0 0 0 16 25 1 0 0 0 0 16 30 1 0 0 0 0 17 28 1 0 0 0 0 18 3 1 1 0 0 0 18 21 1 0 0 0 0 18 32 1 0 0 0 0 19 33 2 0 0 0 0 19 36 1 0 0 0 0 20 10 1 6 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 29 1 1 0 0 0 22 29 1 0 0 0 0 23 30 1 1 0 0 0 24 27 1 0 0 0 0 24 30 1 1 0 0 0 25 26 1 0 0 0 0 25 34 1 1 0 0 0 26 27 1 0 0 0 0 26 31 1 1 0 0 0 27 36 1 1 0 0 0 28 31 2 3 0 0 0 28 35 1 0 0 0 0 29 5 1 1 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.36
Volume:	539.819
LogP:	3.722
LogD:	3.846
LogS:	-4.286
# Rotatable Bonds:	7
TPSA:	78.87
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	5.102
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
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:	-4.749
MDCK Permeability:	1.7069944078684784e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.665
Human Intestinal Absorption (HIA):	0.629
20% Bioavailability (F20%):	0.106
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	74.49574279785156%
Volume Distribution (VD):	1.342
Pgp-substrate:	14.652225494384766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.294
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.283
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.802
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.572

ADMET: Excretion

Clearance (CL):	4.479
Half-life (T1/2):	0.474

ADMET: Toxicity

hERG Blockers:	0.358
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.281
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.817
Maximum Recommended Daily Dose:	0.171
Skin Sensitization:	0.183
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC242692

Natural Product ID:	NPC242692
*Common Name:**	[(2S,3S,4R,5R,8R,9S,10R,13R,17S)-17-[(1S)-1-(Dimethylamino)Ethyl]-2-Hydroxy-10,13-Dimethyl-3-[[(E)-2-Methylbut-2-Enoyl]Amino]-2,3,4,5,6,7,8,9,11,12,16,17-Dodecahydro-1H-Cyclopenta[A]Phenanthren-4-Yl] Acetate
IUPAC Name:	[(2S,3S,4R,5R,8R,9S,10R,13R,17S)-17-[(1S)-1-(dimethylamino)ethyl]-2-hydroxy-10,13-dimethyl-3-[[(E)-2-methylbut-2-enoyl]amino]-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate
Synonyms:
Standard InCHIKey:	MRIVWKAJWKKYCM-WSURCRKTSA-N
Standard InCHI:	InChI=1S/C30H48N2O4/c1-9-17(2)28(35)31-26-25(34)16-30(6)23-14-15-29(5)21(18(3)32(7)8)12-13-22(29)20(23)10-11-24(30)27(26)36-19(4)33/h9,13,18,20-21,23-27,34H,10-12,14-16H2,1-8H3,(H,31,35)/b17-9+/t18-,20-,21+,23-,24-,25-,26-,27+,29+,30+/m0/s1
SMILES:	C/C=C(/C(=N[C@H]1[C@@H](O)C[C@]2([C@H]([C@H]1OC(=O)C)CC[C@@H]1[C@@H]2CC[C@]2(C1=CC[C@@H]2[C@@H](N(C)C)C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL343054
PubChem CID:	11113852
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003060] 16-oxosteroids

*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
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27888	Sarcococca saligna	Species	Buxaceae	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	3
Ki	2

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	IC50	=	61300.0	nM	PMID[484405]
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	Ki	=	134000.0	nM	PMID[484405]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	38360.0	nM	PMID[484405]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	Ki	=	26300.0	nM	PMID[484405]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	61659.5	nM	PMID[484406]

☑ 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 NPC242692 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	102
0.1-0.2	669
0.2-0.3	3165
0.3-0.4	18187
0.4-0.5	11521
0.5-0.6	7447
0.6-0.7	1582
0.7-0.8	15
0.8-0.85	2
0.85-0.9	2
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC472458
0.9375	High Similarity	NPC165396
0.9316	High Similarity	NPC237286
0.9099	High Similarity	NPC472359
0.8938	High Similarity	NPC469968
0.8938	High Similarity	NPC80834
0.8407	Intermediate Similarity	NPC36497
0.8407	Intermediate Similarity	NPC55462
0.8205	Intermediate Similarity	NPC66862
0.8142	Intermediate Similarity	NPC471083
0.7982	Intermediate Similarity	NPC247060
0.7966	Intermediate Similarity	NPC72753
0.7826	Intermediate Similarity	NPC50815
0.7746	Intermediate Similarity	NPC275839
0.7563	Intermediate Similarity	NPC25340
0.7458	Intermediate Similarity	NPC474583
0.7398	Intermediate Similarity	NPC56796
0.7391	Intermediate Similarity	NPC476903
0.7236	Intermediate Similarity	NPC472313
0.719	Intermediate Similarity	NPC258130
0.719	Intermediate Similarity	NPC86906
0.7188	Intermediate Similarity	NPC35037
0.7177	Intermediate Similarity	NPC474459
0.7167	Intermediate Similarity	NPC90538
0.712	Intermediate Similarity	NPC474452
0.7119	Intermediate Similarity	NPC325229
0.7119	Intermediate Similarity	NPC275086
0.7094	Intermediate Similarity	NPC54248
0.7094	Intermediate Similarity	NPC276103
0.7069	Intermediate Similarity	NPC474922
0.7063	Intermediate Similarity	NPC478137
0.7034	Intermediate Similarity	NPC4834
0.7034	Intermediate Similarity	NPC51499
0.7034	Intermediate Similarity	NPC140300
0.7025	Intermediate Similarity	NPC187302
0.7025	Intermediate Similarity	NPC97487
0.7025	Intermediate Similarity	NPC241879
0.7025	Intermediate Similarity	NPC196471
0.7025	Intermediate Similarity	NPC189588
0.7025	Intermediate Similarity	NPC10232
0.7023	Intermediate Similarity	NPC469943
0.7016	Intermediate Similarity	NPC218602
0.6985	Remote Similarity	NPC90814
0.6985	Remote Similarity	NPC189393
0.6975	Remote Similarity	NPC300179
0.6975	Remote Similarity	NPC119036
0.6975	Remote Similarity	NPC102426
0.6975	Remote Similarity	NPC218107
0.6967	Remote Similarity	NPC119329
0.6957	Remote Similarity	NPC53890
0.6957	Remote Similarity	NPC219937
0.6957	Remote Similarity	NPC123252
0.6957	Remote Similarity	NPC194485
0.6917	Remote Similarity	NPC251680
0.6905	Remote Similarity	NPC79238
0.6903	Remote Similarity	NPC166458
0.6897	Remote Similarity	NPC234335
0.6894	Remote Similarity	NPC478138
0.6887	Remote Similarity	NPC217801
0.6885	Remote Similarity	NPC45365
0.6885	Remote Similarity	NPC293299
0.6885	Remote Similarity	NPC473523
0.6885	Remote Similarity	NPC222153
0.6875	Remote Similarity	NPC102048
0.6875	Remote Similarity	NPC299963
0.6875	Remote Similarity	NPC470540
0.6861	Remote Similarity	NPC475472
0.686	Remote Similarity	NPC25177
0.686	Remote Similarity	NPC235920
0.686	Remote Similarity	NPC475617
0.686	Remote Similarity	NPC96784
0.686	Remote Similarity	NPC295110
0.686	Remote Similarity	NPC268829
0.686	Remote Similarity	NPC222875
0.686	Remote Similarity	NPC289670
0.686	Remote Similarity	NPC247701
0.685	Remote Similarity	NPC477291
0.6846	Remote Similarity	NPC471118
0.6846	Remote Similarity	NPC471121
0.6846	Remote Similarity	NPC9714
0.6838	Remote Similarity	NPC26046
0.6833	Remote Similarity	NPC470066
0.6833	Remote Similarity	NPC470067
0.6833	Remote Similarity	NPC470068
0.6829	Remote Similarity	NPC473543
0.6818	Remote Similarity	NPC476504
0.6814	Remote Similarity	NPC152684
0.6812	Remote Similarity	NPC73829
0.6812	Remote Similarity	NPC119794
0.681	Remote Similarity	NPC10274
0.6807	Remote Similarity	NPC253115
0.6807	Remote Similarity	NPC471903
0.6807	Remote Similarity	NPC304899
0.6803	Remote Similarity	NPC226509
0.6803	Remote Similarity	NPC476471
0.6803	Remote Similarity	NPC475344
0.68	Remote Similarity	NPC159367
0.68	Remote Similarity	NPC472218
0.68	Remote Similarity	NPC472219
0.68	Remote Similarity	NPC472217
0.6797	Remote Similarity	NPC235460
0.6786	Remote Similarity	NPC243902
0.6783	Remote Similarity	NPC160304
0.6777	Remote Similarity	NPC275686
0.6777	Remote Similarity	NPC471041
0.6774	Remote Similarity	NPC470055
0.6774	Remote Similarity	NPC119855
0.6774	Remote Similarity	NPC470056
0.6774	Remote Similarity	NPC220217
0.677	Remote Similarity	NPC203005
0.6769	Remote Similarity	NPC471117
0.6769	Remote Similarity	NPC471120
0.6763	Remote Similarity	NPC76999
0.6754	Remote Similarity	NPC270957
0.6754	Remote Similarity	NPC321340
0.6754	Remote Similarity	NPC171698
0.6754	Remote Similarity	NPC119633
0.6754	Remote Similarity	NPC474970
0.6752	Remote Similarity	NPC219516
0.6752	Remote Similarity	NPC130840
0.675	Remote Similarity	NPC240650
0.6748	Remote Similarity	NPC474124
0.6748	Remote Similarity	NPC160583
0.6748	Remote Similarity	NPC45897
0.6746	Remote Similarity	NPC475030
0.6738	Remote Similarity	NPC132847
0.6724	Remote Similarity	NPC16265
0.6723	Remote Similarity	NPC276110
0.6723	Remote Similarity	NPC241047
0.6723	Remote Similarity	NPC279974
0.6721	Remote Similarity	NPC470054
0.672	Remote Similarity	NPC169375
0.672	Remote Similarity	NPC475781
0.672	Remote Similarity	NPC471205
0.6714	Remote Similarity	NPC75318
0.6714	Remote Similarity	NPC280941
0.6714	Remote Similarity	NPC235772
0.6696	Remote Similarity	NPC166857
0.6696	Remote Similarity	NPC472504
0.6695	Remote Similarity	NPC476304
0.6695	Remote Similarity	NPC38232
0.6695	Remote Similarity	NPC93027
0.6694	Remote Similarity	NPC247233
0.6691	Remote Similarity	NPC204556
0.6689	Remote Similarity	NPC36463
0.6689	Remote Similarity	NPC298005
0.6667	Remote Similarity	NPC292718
0.6667	Remote Similarity	NPC306797
0.6667	Remote Similarity	NPC75810
0.6667	Remote Similarity	NPC111834
0.6667	Remote Similarity	NPC289140
0.6667	Remote Similarity	NPC164424
0.6667	Remote Similarity	NPC114743
0.6667	Remote Similarity	NPC476503
0.6667	Remote Similarity	NPC78973
0.6667	Remote Similarity	NPC470053
0.6667	Remote Similarity	NPC145899
0.6667	Remote Similarity	NPC209816
0.6667	Remote Similarity	NPC169270
0.6667	Remote Similarity	NPC152718
0.6667	Remote Similarity	NPC88009
0.6667	Remote Similarity	NPC195366
0.6642	Remote Similarity	NPC476957
0.664	Remote Similarity	NPC186668
0.6639	Remote Similarity	NPC3359
0.6639	Remote Similarity	NPC477972
0.6639	Remote Similarity	NPC105490
0.6639	Remote Similarity	NPC20113
0.6639	Remote Similarity	NPC477971
0.6639	Remote Similarity	NPC208358
0.6639	Remote Similarity	NPC38855
0.6639	Remote Similarity	NPC161527
0.6639	Remote Similarity	NPC476186
0.6639	Remote Similarity	NPC228251
0.6639	Remote Similarity	NPC243985
0.6639	Remote Similarity	NPC119562
0.6639	Remote Similarity	NPC219285
0.6639	Remote Similarity	NPC280710
0.6639	Remote Similarity	NPC279410
0.6639	Remote Similarity	NPC477968
0.6639	Remote Similarity	NPC144202
0.6638	Remote Similarity	NPC34754
0.6614	Remote Similarity	NPC257082
0.6613	Remote Similarity	NPC478057
0.6613	Remote Similarity	NPC472821
0.6612	Remote Similarity	NPC475033
0.6612	Remote Similarity	NPC475032
0.6612	Remote Similarity	NPC476879
0.6612	Remote Similarity	NPC210337
0.6612	Remote Similarity	NPC476893
0.6612	Remote Similarity	NPC476878
0.661	Remote Similarity	NPC110923
0.661	Remote Similarity	NPC249034
0.661	Remote Similarity	NPC74296
0.661	Remote Similarity	NPC41239
0.661	Remote Similarity	NPC329842
0.6609	Remote Similarity	NPC6391
0.6609	Remote Similarity	NPC168231
0.6599	Remote Similarity	NPC473922
0.6597	Remote Similarity	NPC172365

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 NPC242692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	86
0.1-0.2	374
0.2-0.3	2468
0.3-0.4	4107
0.4-0.5	1670
0.5-0.6	401
0.6-0.7	44
0.7-0.8	0
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
0.6917	Remote Similarity	NPD7640	Approved
0.6917	Remote Similarity	NPD7639	Approved
0.6833	Remote Similarity	NPD7638	Approved
0.6822	Remote Similarity	NPD7754	Approved
0.6822	Remote Similarity	NPD7755	Approved
0.678	Remote Similarity	NPD5771	Approved
0.6777	Remote Similarity	NPD8418	Phase 2
0.6667	Remote Similarity	NPD8298	Phase 2
0.6587	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6908	Approved
0.6567	Remote Similarity	NPD6909	Approved
0.6547	Remote Similarity	NPD6914	Discontinued
0.6508	Remote Similarity	NPD6640	Phase 3
0.6462	Remote Similarity	NPD8077	Approved
0.6462	Remote Similarity	NPD8078	Approved
0.6434	Remote Similarity	NPD6421	Discontinued
0.64	Remote Similarity	NPD7632	Discontinued
0.6378	Remote Similarity	NPD7333	Discontinued
0.6378	Remote Similarity	NPD5357	Phase 1
0.6343	Remote Similarity	NPD7327	Approved
0.6343	Remote Similarity	NPD7328	Approved
0.6333	Remote Similarity	NPD7637	Suspended
0.6296	Remote Similarity	NPD7516	Approved
0.6281	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8174	Phase 2
0.626	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6920	Discontinued
0.6233	Remote Similarity	NPD6334	Approved
0.6233	Remote Similarity	NPD6333	Approved
0.6228	Remote Similarity	NPD7525	Registered
0.6225	Remote Similarity	NPD7625	Phase 1
0.622	Remote Similarity	NPD7987	Approved
0.622	Remote Similarity	NPD7912	Approved
0.622	Remote Similarity	NPD7986	Approved
0.622	Remote Similarity	NPD7911	Approved
0.6207	Remote Similarity	NPD6695	Phase 3
0.6204	Remote Similarity	NPD8378	Approved
0.6204	Remote Similarity	NPD8296	Approved
0.6204	Remote Similarity	NPD8380	Approved
0.6204	Remote Similarity	NPD8335	Approved
0.6204	Remote Similarity	NPD8379	Approved
0.6184	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6420	Discontinued
0.6154	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8377	Approved
0.6131	Remote Similarity	NPD8294	Approved
0.6124	Remote Similarity	NPD8040	Discontinued
0.6111	Remote Similarity	NPD6404	Discontinued
0.6098	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6921	Approved
0.6087	Remote Similarity	NPD8033	Approved
0.6077	Remote Similarity	NPD7989	Approved
0.6077	Remote Similarity	NPD7990	Approved
0.6032	Remote Similarity	NPD4225	Approved
0.6031	Remote Similarity	NPD6415	Discontinued
0.6026	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD7645	Phase 2
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD8338	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD6929	Approved
0.5986	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7748	Approved
0.5968	Remote Similarity	NPD5707	Approved
0.5966	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6931	Approved
0.5948	Remote Similarity	NPD6930	Phase 2
0.5948	Remote Similarity	NPD7332	Phase 2
0.5944	Remote Similarity	NPD8337	Approved
0.5944	Remote Similarity	NPD8336	Approved
0.5935	Remote Similarity	NPD8034	Phase 2
0.5935	Remote Similarity	NPD8035	Phase 2
0.5935	Remote Similarity	NPD7515	Phase 2
0.5915	Remote Similarity	NPD7507	Approved
0.5912	Remote Similarity	NPD7115	Discovery
0.5909	Remote Similarity	NPD6881	Approved
0.5909	Remote Similarity	NPD6899	Approved
0.5909	Remote Similarity	NPD7320	Approved
0.5903	Remote Similarity	NPD7319	Approved
0.5902	Remote Similarity	NPD6051	Approved
0.589	Remote Similarity	NPD8449	Approved
0.5887	Remote Similarity	NPD7122	Discontinued
0.5887	Remote Similarity	NPD7604	Phase 2
0.5878	Remote Similarity	NPD4211	Phase 1
0.5868	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6413	Approved
0.5865	Remote Similarity	NPD6373	Approved
0.5865	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6372	Approved
0.5857	Remote Similarity	NPD7503	Approved
0.585	Remote Similarity	NPD8450	Suspended
0.5833	Remote Similarity	NPD5701	Approved
0.5833	Remote Similarity	NPD5697	Approved
0.5827	Remote Similarity	NPD7920	Phase 3
0.5827	Remote Similarity	NPD6083	Phase 2
0.5827	Remote Similarity	NPD7902	Approved
0.5827	Remote Similarity	NPD6084	Phase 2
0.5827	Remote Similarity	NPD7919	Phase 3
0.5826	Remote Similarity	NPD5776	Phase 2
0.5826	Remote Similarity	NPD6925	Approved
0.5821	Remote Similarity	NPD7102	Approved
0.5821	Remote Similarity	NPD6883	Approved
0.5821	Remote Similarity	NPD7290	Approved
0.5814	Remote Similarity	NPD5344	Discontinued
0.5812	Remote Similarity	NPD7514	Phase 3
0.5811	Remote Similarity	NPD8415	Approved
0.5806	Remote Similarity	NPD7087	Discontinued
0.5794	Remote Similarity	NPD7991	Discontinued
0.5789	Remote Similarity	NPD7339	Approved
0.5789	Remote Similarity	NPD6686	Approved
0.5789	Remote Similarity	NPD6942	Approved
0.5785	Remote Similarity	NPD8308	Discontinued
0.5781	Remote Similarity	NPD8088	Phase 1
0.5778	Remote Similarity	NPD6869	Approved
0.5778	Remote Similarity	NPD6847	Approved
0.5778	Remote Similarity	NPD6650	Approved
0.5778	Remote Similarity	NPD6617	Approved
0.5778	Remote Similarity	NPD6649	Approved
0.5778	Remote Similarity	NPD8130	Phase 1
0.5776	Remote Similarity	NPD7145	Approved
0.5772	Remote Similarity	NPD5328	Approved
0.5763	Remote Similarity	NPD6902	Approved
0.5763	Remote Similarity	NPD6898	Phase 1
0.575	Remote Similarity	NPD4786	Approved
0.5746	Remote Similarity	NPD6012	Approved
0.5746	Remote Similarity	NPD6013	Approved
0.5746	Remote Similarity	NPD6014	Approved
0.5735	Remote Similarity	NPD6882	Approved
0.5735	Remote Similarity	NPD7336	Phase 2
0.5735	Remote Similarity	NPD7335	Phase 2
0.5735	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD8297	Approved
0.5734	Remote Similarity	NPD8299	Approved
0.5734	Remote Similarity	NPD8340	Approved
0.5734	Remote Similarity	NPD8342	Approved
0.5734	Remote Similarity	NPD8341	Approved
0.5726	Remote Similarity	NPD3168	Discontinued
0.5726	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6700	Approved
0.5714	Remote Similarity	NPD7522	Discontinued
0.5714	Remote Similarity	NPD7260	Phase 2
0.5704	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6893	Approved
0.5694	Remote Similarity	NPD8273	Phase 1
0.5693	Remote Similarity	NPD4632	Approved
0.569	Remote Similarity	NPD8143	Approved
0.569	Remote Similarity	NPD8144	Approved
0.568	Remote Similarity	NPD6079	Approved
0.5676	Remote Similarity	NPD6845	Suspended
0.5674	Remote Similarity	NPD6319	Approved
0.5672	Remote Similarity	NPD6011	Approved
0.5662	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD3618	Phase 1
0.5655	Remote Similarity	NPD8074	Phase 3
0.5649	Remote Similarity	NPD5211	Phase 2
0.5649	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5646	Remote Similarity	NPD8392	Approved
0.5646	Remote Similarity	NPD8391	Approved
0.5646	Remote Similarity	NPD8390	Approved
0.5641	Remote Similarity	NPD6114	Approved
0.5641	Remote Similarity	NPD6697	Approved
0.5641	Remote Similarity	NPD6115	Approved
0.5641	Remote Similarity	NPD6118	Approved
0.5639	Remote Similarity	NPD6008	Approved
0.5635	Remote Similarity	NPD5779	Approved
0.5635	Remote Similarity	NPD5778	Approved
0.5625	Remote Similarity	NPD7492	Approved
0.5616	Remote Similarity	NPD7736	Approved
0.5615	Remote Similarity	NPD6648	Approved
0.5603	Remote Similarity	NPD7518	Approved
0.5603	Remote Similarity	NPD7519	Approved
0.5603	Remote Similarity	NPD7517	Approved
0.5603	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8522	Clinical (unspecified phase)

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