NPASS Compound

Structure

NPC476127 OpenBabel07101718242D 46 51 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 -6.1097 -3.4067 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 -6.7788 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -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 2 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3007 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 1 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 6.0622 1.5000 0.0000 O 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 6.0622 -0.5000 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5575 -1.3363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -1.7976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 31 1 0 0 0 0 3 31 1 0 0 0 0 5 6 1 0 0 0 0 6 19 1 0 0 0 0 7 9 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 32 1 0 0 0 0 10 41 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 33 1 0 0 0 0 13 1 1 1 0 0 0 13 21 1 0 0 0 0 13 42 1 0 0 0 0 14 5 1 1 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 27 1 0 0 0 0 16 32 1 1 0 0 0 17 15 1 1 0 0 0 17 43 1 0 0 0 0 18 12 1 6 0 0 0 18 22 1 0 0 0 0 18 44 1 0 0 0 0 19 31 1 0 0 0 0 19 32 1 6 0 0 0 20 31 1 0 0 0 0 20 45 1 6 0 0 0 21 23 1 0 0 0 0 21 34 1 6 0 0 0 22 24 1 0 0 0 0 22 35 1 1 0 0 0 23 25 1 0 0 0 0 23 36 1 1 0 0 0 24 26 1 0 0 0 0 24 37 1 6 0 0 0 25 29 1 0 0 0 0 25 38 1 1 0 0 0 26 30 1 0 0 0 0 26 46 1 1 0 0 0 27 39 2 0 0 0 0 27 41 1 0 0 0 0 28 40 1 0 0 0 0 28 43 1 0 0 0 0 29 42 1 0 0 0 0 29 46 1 6 0 0 0 30 44 1 0 0 0 0 30 45 1 6 0 0 0 32 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	658.32
Volume:	628.479
LogP:	1.764
LogD:	2.049
LogS:	-2.842
# Rotatable Bonds:	6
TPSA:	221.13
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.192
Synthetic Accessibility Score:	5.596
Fsp3:	0.875
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:	-6.28
MDCK Permeability:	7.660865230718628e-05
Pgp-inhibitor:	0.091
Pgp-substrate:	0.634
Human Intestinal Absorption (HIA):	0.853
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	90.44542694091797%
Volume Distribution (VD):	0.266
Pgp-substrate:	10.517012596130371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.208
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	0.682
Half-life (T1/2):	0.713

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.249
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.282
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC476127

Natural Product ID:	NPC476127
*Common Name:**	Alpindenoside C
IUPAC Name:	4-[(2R,4aR,6aR,8S,10aR,10bR)-8-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-7,7,10a-trimethyl-2,4,4a,5,6,6a,8,9,10,10b-decahydro-1H-benzo[f]isochromen-2-yl]-2H-furan-5-one
Synonyms:	Alpindenoside C
Standard InCHIKey:	RPQCAISSRKTLEA-BOWDQLTHSA-N
Standard InCHI:	InChI=1S/C32H50O14/c1-13-21(34)23(36)25(38)29(42-13)46-26-24(37)22(35)18(12-33)44-30(26)45-20-7-9-32(4)16-11-17(15-8-10-41-27(15)39)43-28(40)14(16)5-6-19(32)31(20,2)3/h8,13-14,16-26,28-30,33-38,40H,5-7,9-12H2,1-4H3/t13-,14+,16+,17+,18+,19-,20-,21-,22+,23+,24-,25+,26+,28?,29-,30-,32+/m0/s1
SMILES:	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4(C(C3(C)C)CCC5C4CC(OC5O)C6=CCOC6=O)C)CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL538421
PubChem CID:	45270726
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO594	Alpinia densespicata	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555124]
NPO594	Alpinia densespicata	Species	Staphylinidae	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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	38000.0	nM	PMID[517493]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	80.0	%	PMID[517493]
NPT1	Others	Radical scavenging activity		ED50	>	200.0	ug ml-1	PMID[517493]

☑ 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 NPC476127 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	277
0.1-0.2	1653
0.2-0.3	4543
0.3-0.4	7985
0.4-0.5	12276
0.5-0.6	7986
0.6-0.7	4666
0.7-0.8	2182
0.8-0.85	462
0.85-0.9	534
0.9-0.95	130
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476150
0.9727	High Similarity	NPC474483
0.9558	High Similarity	NPC170084
0.9558	High Similarity	NPC476204
0.9153	High Similarity	NPC470516
0.913	High Similarity	NPC470312
0.9083	High Similarity	NPC311178
0.9083	High Similarity	NPC43589
0.9083	High Similarity	NPC300655
0.9083	High Similarity	NPC222951
0.9076	High Similarity	NPC23020
0.9076	High Similarity	NPC472268
0.9076	High Similarity	NPC112492
0.9076	High Similarity	NPC472270
0.9076	High Similarity	NPC472269
0.9008	High Similarity	NPC319719
0.9008	High Similarity	NPC183816
0.9008	High Similarity	NPC475177
0.9008	High Similarity	NPC473679
0.9008	High Similarity	NPC322904
0.9008	High Similarity	NPC233223
0.9008	High Similarity	NPC324933
0.9008	High Similarity	NPC196874
0.9008	High Similarity	NPC475444
0.9	High Similarity	NPC392
0.9	High Similarity	NPC177524
0.9	High Similarity	NPC219900
0.8957	High Similarity	NPC471548
0.8947	High Similarity	NPC44170
0.8917	High Similarity	NPC45606
0.8917	High Similarity	NPC220838
0.8908	High Similarity	NPC297950
0.887	High Similarity	NPC473405
0.8862	High Similarity	NPC329636
0.886	High Similarity	NPC475486
0.886	High Similarity	NPC164389
0.8852	High Similarity	NPC476776
0.885	High Similarity	NPC1046
0.885	High Similarity	NPC80843
0.8843	High Similarity	NPC470518
0.8843	High Similarity	NPC88311
0.8843	High Similarity	NPC47995
0.8843	High Similarity	NPC252289
0.8843	High Similarity	NPC477196
0.8843	High Similarity	NPC115656
0.8843	High Similarity	NPC273878
0.8843	High Similarity	NPC269484
0.8843	High Similarity	NPC11577
0.8843	High Similarity	NPC107536
0.8843	High Similarity	NPC97918
0.8843	High Similarity	NPC252657
0.8843	High Similarity	NPC280029
0.8843	High Similarity	NPC141600
0.8843	High Similarity	NPC305793
0.8843	High Similarity	NPC1314
0.8843	High Similarity	NPC244296
0.8843	High Similarity	NPC472267
0.8843	High Similarity	NPC476966
0.8843	High Similarity	NPC9470
0.8843	High Similarity	NPC82380
0.8843	High Similarity	NPC265841
0.8833	High Similarity	NPC240070
0.8833	High Similarity	NPC329784
0.8793	High Similarity	NPC105800
0.8793	High Similarity	NPC470515
0.8793	High Similarity	NPC232237
0.879	High Similarity	NPC194716
0.8783	High Similarity	NPC268954
0.8783	High Similarity	NPC288205
0.8783	High Similarity	NPC37134
0.8783	High Similarity	NPC26626
0.8783	High Similarity	NPC291903
0.8783	High Similarity	NPC305267
0.8783	High Similarity	NPC51465
0.8783	High Similarity	NPC476992
0.8783	High Similarity	NPC75287
0.878	High Similarity	NPC476779
0.878	High Similarity	NPC116075
0.878	High Similarity	NPC316915
0.878	High Similarity	NPC247190
0.878	High Similarity	NPC146857
0.878	High Similarity	NPC469749
0.878	High Similarity	NPC32793
0.8772	High Similarity	NPC475208
0.8772	High Similarity	NPC238935
0.8772	High Similarity	NPC264153
0.877	High Similarity	NPC271610
0.877	High Similarity	NPC477197
0.877	High Similarity	NPC25998
0.877	High Similarity	NPC476775
0.877	High Similarity	NPC476780
0.877	High Similarity	NPC478155
0.877	High Similarity	NPC476774
0.8761	High Similarity	NPC31839
0.8761	High Similarity	NPC164419
0.876	High Similarity	NPC477194
0.876	High Similarity	NPC245094
0.876	High Similarity	NPC477193
0.876	High Similarity	NPC477192
0.876	High Similarity	NPC477191
0.875	High Similarity	NPC476759
0.872	High Similarity	NPC329675
0.8718	High Similarity	NPC470517
0.8718	High Similarity	NPC470914
0.8718	High Similarity	NPC470911
0.8718	High Similarity	NPC122971
0.8718	High Similarity	NPC470915
0.8718	High Similarity	NPC207738
0.871	High Similarity	NPC476777
0.871	High Similarity	NPC476778
0.8707	High Similarity	NPC104137
0.8707	High Similarity	NPC473824
0.8707	High Similarity	NPC286457
0.8707	High Similarity	NPC33012
0.8707	High Similarity	NPC309223
0.8707	High Similarity	NPC475209
0.8707	High Similarity	NPC69811
0.8707	High Similarity	NPC123522
0.8707	High Similarity	NPC475514
0.8707	High Similarity	NPC470876
0.8707	High Similarity	NPC475119
0.8707	High Similarity	NPC8524
0.8707	High Similarity	NPC102505
0.8707	High Similarity	NPC191827
0.8707	High Similarity	NPC300419
0.8707	High Similarity	NPC323359
0.8707	High Similarity	NPC473452
0.8707	High Similarity	NPC471547
0.8707	High Similarity	NPC220160
0.8707	High Similarity	NPC85154
0.8699	High Similarity	NPC231240
0.8699	High Similarity	NPC178264
0.8699	High Similarity	NPC478150
0.8699	High Similarity	NPC277212
0.8699	High Similarity	NPC473918
0.8699	High Similarity	NPC71391
0.8699	High Similarity	NPC192765
0.8699	High Similarity	NPC30279
0.8699	High Similarity	NPC478153
0.8699	High Similarity	NPC46823
0.8699	High Similarity	NPC312650
0.8699	High Similarity	NPC478154
0.8699	High Similarity	NPC477195
0.8699	High Similarity	NPC478152
0.8696	High Similarity	NPC110861
0.8689	High Similarity	NPC477079
0.8689	High Similarity	NPC470912
0.8689	High Similarity	NPC477076
0.8689	High Similarity	NPC188234
0.8689	High Similarity	NPC477077
0.8689	High Similarity	NPC140092
0.8689	High Similarity	NPC276838
0.8689	High Similarity	NPC232785
0.8689	High Similarity	NPC470913
0.8689	High Similarity	NPC125077
0.8689	High Similarity	NPC329986
0.8684	High Similarity	NPC473373
0.8684	High Similarity	NPC257468
0.8684	High Similarity	NPC469946
0.8684	High Similarity	NPC276093
0.8684	High Similarity	NPC101744
0.8684	High Similarity	NPC475504
0.8684	High Similarity	NPC109079
0.8684	High Similarity	NPC102439
0.8684	High Similarity	NPC139044
0.8684	High Similarity	NPC48249
0.8684	High Similarity	NPC292677
0.8684	High Similarity	NPC471383
0.8684	High Similarity	NPC471967
0.8684	High Similarity	NPC104400
0.8684	High Similarity	NPC10320
0.8684	High Similarity	NPC79718
0.8684	High Similarity	NPC324875
0.8684	High Similarity	NPC104071
0.8684	High Similarity	NPC475516
0.8678	High Similarity	NPC117702
0.8678	High Similarity	NPC146456
0.8678	High Similarity	NPC471357
0.8678	High Similarity	NPC469757
0.8673	High Similarity	NPC78046
0.8673	High Similarity	NPC270667
0.8673	High Similarity	NPC474589
0.8673	High Similarity	NPC164194
0.8673	High Similarity	NPC279554
0.8673	High Similarity	NPC90856
0.8673	High Similarity	NPC269095
0.8673	High Similarity	NPC242611
0.8673	High Similarity	NPC29069
0.8673	High Similarity	NPC475296
0.8673	High Similarity	NPC127056
0.8673	High Similarity	NPC476766
0.8673	High Similarity	NPC59804
0.8673	High Similarity	NPC136877
0.8673	High Similarity	NPC56713
0.8673	High Similarity	NPC174679
0.8667	High Similarity	NPC318135
0.8661	High Similarity	NPC473483
0.8644	High Similarity	NPC135369
0.8644	High Similarity	NPC153673
0.8644	High Similarity	NPC37860

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 NPC476127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	1855
0.2-0.3	3719
0.3-0.4	2172
0.4-0.5	673
0.5-0.6	323
0.6-0.7	115
0.7-0.8	21
0.8-0.85	7
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD6686	Approved
0.8644	High Similarity	NPD8294	Approved
0.8644	High Similarity	NPD8377	Approved
0.8571	High Similarity	NPD8379	Approved
0.8571	High Similarity	NPD8335	Approved
0.8571	High Similarity	NPD8380	Approved
0.8571	High Similarity	NPD8378	Approved
0.8571	High Similarity	NPD8296	Approved
0.8537	High Similarity	NPD7319	Approved
0.8448	Intermediate Similarity	NPD8133	Approved
0.8443	Intermediate Similarity	NPD7507	Approved
0.843	Intermediate Similarity	NPD8328	Phase 3
0.8417	Intermediate Similarity	NPD8033	Approved
0.8167	Intermediate Similarity	NPD7327	Approved
0.8167	Intermediate Similarity	NPD7328	Approved
0.8115	Intermediate Similarity	NPD8515	Approved
0.8115	Intermediate Similarity	NPD8513	Phase 3
0.8115	Intermediate Similarity	NPD8516	Approved
0.8115	Intermediate Similarity	NPD8517	Approved
0.8103	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD7516	Approved
0.8083	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD7503	Approved
0.7931	Intermediate Similarity	NPD6412	Phase 2
0.7734	Intermediate Similarity	NPD7736	Approved
0.7647	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7115	Discovery
0.7632	Intermediate Similarity	NPD4225	Approved
0.7632	Intermediate Similarity	NPD7638	Approved
0.7565	Intermediate Similarity	NPD7640	Approved
0.7565	Intermediate Similarity	NPD7639	Approved
0.7521	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD8293	Discontinued
0.748	Intermediate Similarity	NPD6370	Approved
0.7438	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7492	Approved
0.7323	Intermediate Similarity	NPD6054	Approved
0.7323	Intermediate Similarity	NPD6319	Approved
0.7308	Intermediate Similarity	NPD6616	Approved
0.7281	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7078	Approved
0.7241	Intermediate Similarity	NPD7902	Approved
0.719	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6059	Approved
0.7177	Intermediate Similarity	NPD6882	Approved
0.7177	Intermediate Similarity	NPD8297	Approved
0.7168	Intermediate Similarity	NPD6698	Approved
0.7168	Intermediate Similarity	NPD46	Approved
0.7132	Intermediate Similarity	NPD6016	Approved
0.7132	Intermediate Similarity	NPD6015	Approved
0.7121	Intermediate Similarity	NPD8074	Phase 3
0.7105	Intermediate Similarity	NPD7515	Phase 2
0.7087	Intermediate Similarity	NPD6009	Approved
0.7077	Intermediate Similarity	NPD5988	Approved
0.7034	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7632	Discontinued
0.6984	Remote Similarity	NPD4632	Approved
0.6983	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7900	Approved
0.6911	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7829	Approved
0.6894	Remote Similarity	NPD7830	Approved
0.6894	Remote Similarity	NPD6067	Discontinued
0.688	Remote Similarity	NPD6371	Approved
0.6855	Remote Similarity	NPD6881	Approved
0.6855	Remote Similarity	NPD6899	Approved
0.6829	Remote Similarity	NPD7128	Approved
0.6829	Remote Similarity	NPD5739	Approved
0.6829	Remote Similarity	NPD6675	Approved
0.6829	Remote Similarity	NPD6402	Approved
0.6828	Remote Similarity	NPD7625	Phase 1
0.6825	Remote Similarity	NPD8130	Phase 1
0.6825	Remote Similarity	NPD6650	Approved
0.6825	Remote Similarity	NPD6649	Approved
0.68	Remote Similarity	NPD6373	Approved
0.68	Remote Similarity	NPD6372	Approved
0.6777	Remote Similarity	NPD5344	Discontinued
0.6774	Remote Similarity	NPD5697	Approved
0.6746	Remote Similarity	NPD6883	Approved
0.6746	Remote Similarity	NPD4634	Approved
0.6746	Remote Similarity	NPD7102	Approved
0.6746	Remote Similarity	NPD7290	Approved
0.6742	Remote Similarity	NPD6921	Approved
0.6724	Remote Similarity	NPD7838	Discovery
0.672	Remote Similarity	NPD7320	Approved
0.6693	Remote Similarity	NPD6847	Approved
0.6693	Remote Similarity	NPD6617	Approved
0.6693	Remote Similarity	NPD6869	Approved
0.6691	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6642	Remote Similarity	NPD7604	Phase 2
0.664	Remote Similarity	NPD5701	Approved
0.6617	Remote Similarity	NPD5983	Phase 2
0.661	Remote Similarity	NPD8171	Discontinued
0.661	Remote Similarity	NPD6399	Phase 3
0.6594	Remote Similarity	NPD8392	Approved
0.6594	Remote Similarity	NPD8391	Approved
0.6594	Remote Similarity	NPD8390	Approved
0.6587	Remote Similarity	NPD6011	Approved
0.6569	Remote Similarity	NPD8337	Approved
0.6569	Remote Similarity	NPD8336	Approved
0.6549	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8451	Approved
0.6544	Remote Similarity	NPD6336	Discontinued
0.6529	Remote Similarity	NPD6084	Phase 2
0.6529	Remote Similarity	NPD6083	Phase 2
0.6525	Remote Similarity	NPD6079	Approved
0.6525	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD3618	Phase 1
0.6512	Remote Similarity	NPD6053	Discontinued
0.6496	Remote Similarity	NPD5328	Approved
0.6496	Remote Similarity	NPD8448	Approved
0.6491	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6466	Remote Similarity	NPD3573	Approved
0.6452	Remote Similarity	NPD5211	Phase 2
0.6444	Remote Similarity	NPD8080	Discontinued
0.6439	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD1694	Approved
0.6434	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7260	Phase 2
0.6429	Remote Similarity	NPD6008	Approved
0.6423	Remote Similarity	NPD5285	Approved
0.6423	Remote Similarity	NPD6648	Approved
0.6423	Remote Similarity	NPD5286	Approved
0.6423	Remote Similarity	NPD4696	Approved
0.641	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD7642	Approved
0.6393	Remote Similarity	NPD4755	Approved
0.6387	Remote Similarity	NPD7637	Suspended
0.6383	Remote Similarity	NPD8338	Approved
0.638	Remote Similarity	NPD7799	Discontinued
0.6379	Remote Similarity	NPD7521	Approved
0.6379	Remote Similarity	NPD6409	Approved
0.6379	Remote Similarity	NPD7334	Approved
0.6379	Remote Similarity	NPD7146	Approved
0.6379	Remote Similarity	NPD5330	Approved
0.6379	Remote Similarity	NPD6684	Approved
0.637	Remote Similarity	NPD8444	Approved
0.6364	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6274	Approved
0.6357	Remote Similarity	NPD6914	Discontinued
0.6357	Remote Similarity	NPD5956	Approved
0.6356	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6101	Approved
0.635	Remote Similarity	NPD8340	Approved
0.635	Remote Similarity	NPD8342	Approved
0.635	Remote Similarity	NPD8341	Approved
0.635	Remote Similarity	NPD8299	Approved
0.6349	Remote Similarity	NPD5141	Approved
0.6343	Remote Similarity	NPD7100	Approved
0.6343	Remote Similarity	NPD7101	Approved
0.6333	Remote Similarity	NPD4202	Approved
0.632	Remote Similarity	NPD5224	Approved
0.632	Remote Similarity	NPD5226	Approved
0.632	Remote Similarity	NPD4633	Approved
0.632	Remote Similarity	NPD5225	Approved
0.6311	Remote Similarity	NPD7839	Suspended
0.6311	Remote Similarity	NPD5221	Approved
0.6311	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5222	Approved
0.6303	Remote Similarity	NPD5785	Approved
0.6294	Remote Similarity	NPD8415	Approved
0.629	Remote Similarity	NPD4700	Approved
0.6271	Remote Similarity	NPD6672	Approved
0.6271	Remote Similarity	NPD5737	Approved
0.6271	Remote Similarity	NPD6903	Approved
0.627	Remote Similarity	NPD5174	Approved
0.627	Remote Similarity	NPD5175	Approved
0.6269	Remote Similarity	NPD6335	Approved
0.6268	Remote Similarity	NPD8449	Approved
0.626	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6868	Approved
0.624	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5695	Phase 3
0.6224	Remote Similarity	NPD8450	Suspended
0.621	Remote Similarity	NPD5696	Approved
0.6207	Remote Similarity	NPD4786	Approved
0.6207	Remote Similarity	NPD3666	Approved
0.6207	Remote Similarity	NPD3665	Phase 1
0.6207	Remote Similarity	NPD3133	Approved
0.6202	Remote Similarity	NPD4730	Approved
0.6202	Remote Similarity	NPD4729	Approved
0.6195	Remote Similarity	NPD7645	Phase 2
0.6194	Remote Similarity	NPD6317	Approved
0.6179	Remote Similarity	NPD4697	Phase 3

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