NPASS Compound

Structure

NPC91497 OpenBabel07101719252D 43 47 0 0 1 0 0 0 0 0999 V2000 -7.8986 -3.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 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 -5.4041 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3986 -4.8147 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 -6.8986 -3.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3986 -3.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 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 -1.7321 -5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8053 -2.1691 0.0000 C 0 0 2 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 -2.5981 -4.5000 0.0000 C 0 0 2 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 -2.5981 -3.5000 0.0000 C 0 0 2 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 -1.7321 -3.0000 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 -3.4641 0.0000 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 -6.8986 -5.6808 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 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7835 -1.9612 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 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -1.7321 0.0000 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 1 13 2 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 6 7 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 31 1 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 32 1 0 0 0 0 12 33 1 0 0 0 0 14 2 1 1 0 0 0 14 21 1 0 0 0 0 14 40 1 0 0 0 0 15 6 1 6 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 13 1 6 0 0 0 16 22 1 0 0 0 0 17 31 1 6 0 0 0 18 12 1 6 0 0 0 18 23 1 0 0 0 0 18 41 1 0 0 0 0 19 30 1 0 0 0 0 19 31 1 1 0 0 0 20 30 1 0 0 0 0 20 42 1 1 0 0 0 21 24 1 0 0 0 0 21 34 1 6 0 0 0 22 35 1 6 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 1 0 0 0 25 27 1 0 0 0 0 25 38 1 6 0 0 0 26 28 1 0 0 0 0 26 39 1 1 0 0 0 27 29 1 0 0 0 0 27 43 1 1 0 0 0 28 40 1 0 0 0 0 28 43 1 6 0 0 0 29 41 1 0 0 0 0 29 42 1 6 0 0 0 31 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.35
Volume:	604.796
LogP:	1.611
LogD:	1.929
LogS:	-2.753
# Rotatable Bonds:	7
TPSA:	198.76
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.134
Synthetic Accessibility Score:	5.471
Fsp3:	0.935
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:	-5.955
MDCK Permeability:	8.286819502245635e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.818
20% Bioavailability (F20%):	0.251
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	67.52925872802734%
Volume Distribution (VD):	0.471
Pgp-substrate:	21.9552001953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.42
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	0.78
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.119
Skin Sensitization:	0.435
Carcinogencity:	0.012
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC91497

Natural Product ID:	NPC91497
*Common Name:**	Noralpindenoside A
IUPAC Name:	(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,3aR,5aR,7S,9aR,9bR)-3-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-6,6,9a-trimethyl-2,3,3a,4,5,5a,7,8,9,9b-decahydro-1H-cyclopenta[a]naphthalen-7-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms:	Noralpindenoside A
Standard InCHIKey:	QHYMJEOZZXVMGS-DUZGSJEVSA-N
Standard InCHI:	InChI=1S/C31H52O12/c1-13(11-32)16-10-17-15(22(16)35)6-7-19-30(3,4)20(8-9-31(17,19)5)42-29-27(25(38)23(36)18(12-33)41-29)43-28-26(39)24(37)21(34)14(2)40-28/h14-29,32-39H,1,6-12H2,2-5H3/t14-,15+,16+,17+,18+,19-,20-,21-,22+,23+,24+,25-,26+,27+,28-,29-,31+/m0/s1
SMILES:	C=C(CO)[C@H]1C[C@@H]2[C@@H](CC[C@H]3C(C)(C)[C@H](CC[C@]23C)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)[C@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL538422
PubChem CID:	44178751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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	=	31800.0	nM	PMID[569903]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	80.0	%	PMID[569903]
NPT1	Others	Radical scavenging activity		ED50	>	200.0	ug ml-1	PMID[569903]

☑ 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 NPC91497 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	271
0.1-0.2	2292
0.2-0.3	6847
0.3-0.4	13390
0.4-0.5	8636
0.5-0.6	5069
0.6-0.7	3707
0.7-0.8	1845
0.8-0.85	483
0.85-0.9	141
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC76486
0.9474	High Similarity	NPC470168
0.9368	High Similarity	NPC471247
0.9184	High Similarity	NPC475521
0.9149	High Similarity	NPC473348
0.914	High Similarity	NPC296620
0.9091	High Similarity	NPC242748
0.9082	High Similarity	NPC473198
0.9072	High Similarity	NPC31346
0.9053	High Similarity	NPC472989
0.9	High Similarity	NPC473469
0.9	High Similarity	NPC470169
0.9	High Similarity	NPC470170
0.899	High Similarity	NPC75608
0.8947	High Similarity	NPC30477
0.8911	High Similarity	NPC7213
0.8911	High Similarity	NPC475634
0.8911	High Similarity	NPC476513
0.89	High Similarity	NPC472900
0.89	High Similarity	NPC473923
0.89	High Similarity	NPC472899
0.89	High Similarity	NPC165405
0.89	High Similarity	NPC473476
0.89	High Similarity	NPC472898
0.8878	High Similarity	NPC144486
0.8866	High Similarity	NPC469725
0.883	High Similarity	NPC469738
0.8824	High Similarity	NPC474573
0.8812	High Similarity	NPC231340
0.8812	High Similarity	NPC470166
0.8812	High Similarity	NPC54619
0.88	High Similarity	NPC470885
0.88	High Similarity	NPC187400
0.88	High Similarity	NPC476361
0.88	High Similarity	NPC221562
0.88	High Similarity	NPC476360
0.8788	High Similarity	NPC312553
0.8788	High Similarity	NPC159036
0.8788	High Similarity	NPC136816
0.8788	High Similarity	NPC288694
0.8776	High Similarity	NPC7341
0.8776	High Similarity	NPC473200
0.8738	High Similarity	NPC141433
0.8725	High Similarity	NPC476540
0.8725	High Similarity	NPC472897
0.8725	High Similarity	NPC476541
0.8725	High Similarity	NPC49032
0.8725	High Similarity	NPC125324
0.8725	High Similarity	NPC476538
0.8725	High Similarity	NPC51172
0.8725	High Similarity	NPC472896
0.8725	High Similarity	NPC476539
0.8713	High Similarity	NPC474569
0.8713	High Similarity	NPC181845
0.87	High Similarity	NPC211879
0.87	High Similarity	NPC8039
0.87	High Similarity	NPC157659
0.87	High Similarity	NPC120123
0.87	High Similarity	NPC31907
0.87	High Similarity	NPC245280
0.87	High Similarity	NPC189852
0.87	High Similarity	NPC155010
0.87	High Similarity	NPC16573
0.87	High Similarity	NPC473020
0.87	High Similarity	NPC471467
0.87	High Similarity	NPC286969
0.87	High Similarity	NPC472252
0.87	High Similarity	NPC114874
0.87	High Similarity	NPC131479
0.87	High Similarity	NPC16520
0.8687	High Similarity	NPC129372
0.8687	High Similarity	NPC4831
0.8687	High Similarity	NPC160734
0.8687	High Similarity	NPC472023
0.8687	High Similarity	NPC309425
0.8687	High Similarity	NPC47566
0.8687	High Similarity	NPC470434
0.8687	High Similarity	NPC88000
0.8673	High Similarity	NPC234287
0.8673	High Similarity	NPC280825
0.8667	High Similarity	NPC51154
0.8667	High Similarity	NPC307642
0.8654	High Similarity	NPC13190
0.8654	High Similarity	NPC114188
0.8654	High Similarity	NPC197231
0.8641	High Similarity	NPC477027
0.8641	High Similarity	NPC151134
0.8641	High Similarity	NPC306131
0.8641	High Similarity	NPC477026
0.8641	High Similarity	NPC70204
0.8641	High Similarity	NPC475670
0.8632	High Similarity	NPC48463
0.8627	High Similarity	NPC226642
0.8627	High Similarity	NPC14704
0.8627	High Similarity	NPC230507
0.8627	High Similarity	NPC283829
0.8627	High Similarity	NPC305423
0.8627	High Similarity	NPC161676
0.8627	High Similarity	NPC113044
0.8627	High Similarity	NPC190395
0.8627	High Similarity	NPC94272
0.8627	High Similarity	NPC470432
0.8614	High Similarity	NPC165033
0.8614	High Similarity	NPC93352
0.8614	High Similarity	NPC475365
0.8614	High Similarity	NPC312774
0.8614	High Similarity	NPC273879
0.86	High Similarity	NPC31085
0.86	High Similarity	NPC272015
0.8586	High Similarity	NPC469942
0.8586	High Similarity	NPC471242
0.8586	High Similarity	NPC64348
0.8571	High Similarity	NPC473890
0.8571	High Similarity	NPC216595
0.8571	High Similarity	NPC243728
0.8571	High Similarity	NPC112274
0.8571	High Similarity	NPC473567
0.8571	High Similarity	NPC19888
0.8558	High Similarity	NPC470867
0.8557	High Similarity	NPC476894
0.8544	High Similarity	NPC98696
0.8544	High Similarity	NPC295980
0.8529	High Similarity	NPC208594
0.8529	High Similarity	NPC152584
0.8529	High Similarity	NPC309448
0.8529	High Similarity	NPC69737
0.8529	High Similarity	NPC269627
0.8529	High Similarity	NPC160816
0.8529	High Similarity	NPC194842
0.8529	High Similarity	NPC208477
0.8529	High Similarity	NPC127801
0.8529	High Similarity	NPC26798
0.8526	High Similarity	NPC65550
0.8515	High Similarity	NPC213190
0.8515	High Similarity	NPC475701
0.8511	High Similarity	NPC281004
0.85	High Similarity	NPC471112
0.8491	Intermediate Similarity	NPC476693
0.8485	Intermediate Similarity	NPC476895
0.8485	Intermediate Similarity	NPC158088
0.8485	Intermediate Similarity	NPC157739
0.8476	Intermediate Similarity	NPC472987
0.8476	Intermediate Similarity	NPC475247
0.8476	Intermediate Similarity	NPC294129
0.8476	Intermediate Similarity	NPC476547
0.8476	Intermediate Similarity	NPC473021
0.8469	Intermediate Similarity	NPC90583
0.8469	Intermediate Similarity	NPC207617
0.8462	Intermediate Similarity	NPC477809
0.8462	Intermediate Similarity	NPC470433
0.8462	Intermediate Similarity	NPC84956
0.8462	Intermediate Similarity	NPC302057
0.8462	Intermediate Similarity	NPC102016
0.8462	Intermediate Similarity	NPC300557
0.8462	Intermediate Similarity	NPC244086
0.8462	Intermediate Similarity	NPC22779
0.8462	Intermediate Similarity	NPC476835
0.8462	Intermediate Similarity	NPC224098
0.8462	Intermediate Similarity	NPC14630
0.8462	Intermediate Similarity	NPC171073
0.8462	Intermediate Similarity	NPC73243
0.8462	Intermediate Similarity	NPC249265
0.8462	Intermediate Similarity	NPC150372
0.8462	Intermediate Similarity	NPC208383
0.8462	Intermediate Similarity	NPC250089
0.8462	Intermediate Similarity	NPC309278
0.8462	Intermediate Similarity	NPC95051
0.8462	Intermediate Similarity	NPC157530
0.8462	Intermediate Similarity	NPC46190
0.8462	Intermediate Similarity	NPC232054
0.8462	Intermediate Similarity	NPC6806
0.8462	Intermediate Similarity	NPC42482
0.8462	Intermediate Similarity	NPC475550
0.8462	Intermediate Similarity	NPC194207
0.8462	Intermediate Similarity	NPC472901
0.8462	Intermediate Similarity	NPC475333
0.8462	Intermediate Similarity	NPC40440
0.8462	Intermediate Similarity	NPC218571
0.8462	Intermediate Similarity	NPC248746
0.8454	Intermediate Similarity	NPC72817
0.8454	Intermediate Similarity	NPC477927
0.8447	Intermediate Similarity	NPC14946
0.8447	Intermediate Similarity	NPC33053
0.8447	Intermediate Similarity	NPC181467
0.8447	Intermediate Similarity	NPC208650
0.8447	Intermediate Similarity	NPC234160
0.8447	Intermediate Similarity	NPC476594
0.8447	Intermediate Similarity	NPC63368
0.8438	Intermediate Similarity	NPC473830
0.8438	Intermediate Similarity	NPC204881
0.8431	Intermediate Similarity	NPC474464
0.8421	Intermediate Similarity	NPC102725
0.8421	Intermediate Similarity	NPC473472
0.8416	Intermediate Similarity	NPC177701
0.8416	Intermediate Similarity	NPC52585
0.8416	Intermediate Similarity	NPC68630
0.8416	Intermediate Similarity	NPC228049
0.8411	Intermediate Similarity	NPC477810
0.8411	Intermediate Similarity	NPC11548
0.84	Intermediate Similarity	NPC317019

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 NPC91497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	2556
0.2-0.3	4130
0.3-0.4	1410
0.4-0.5	410
0.5-0.6	261
0.6-0.7	114
0.7-0.8	12
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8163	Intermediate Similarity	NPD8171	Discontinued
0.8125	Intermediate Similarity	NPD8033	Approved
0.8036	Intermediate Similarity	NPD8294	Approved
0.8036	Intermediate Similarity	NPD8377	Approved
0.8018	Intermediate Similarity	NPD7328	Approved
0.8018	Intermediate Similarity	NPD7327	Approved
0.7982	Intermediate Similarity	NPD8133	Approved
0.7965	Intermediate Similarity	NPD8380	Approved
0.7965	Intermediate Similarity	NPD8379	Approved
0.7965	Intermediate Similarity	NPD8296	Approved
0.7965	Intermediate Similarity	NPD8335	Approved
0.7965	Intermediate Similarity	NPD8378	Approved
0.7946	Intermediate Similarity	NPD7516	Approved
0.7757	Intermediate Similarity	NPD6412	Phase 2
0.7652	Intermediate Similarity	NPD7503	Approved
0.7542	Intermediate Similarity	NPD7507	Approved
0.7474	Intermediate Similarity	NPD6928	Phase 2
0.7407	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7524	Approved
0.7054	Intermediate Similarity	NPD6686	Approved
0.704	Intermediate Similarity	NPD8449	Approved
0.7009	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6370	Approved
0.6984	Remote Similarity	NPD8450	Suspended
0.6939	Remote Similarity	NPD7525	Registered
0.69	Remote Similarity	NPD6695	Phase 3
0.6881	Remote Similarity	NPD7639	Approved
0.6881	Remote Similarity	NPD7640	Approved
0.6855	Remote Similarity	NPD7736	Approved
0.6833	Remote Similarity	NPD6054	Approved
0.6833	Remote Similarity	NPD6059	Approved
0.6803	Remote Similarity	NPD8328	Phase 3
0.6796	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7638	Approved
0.6774	Remote Similarity	NPD8293	Discontinued
0.6701	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8035	Phase 2
0.6698	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD1811	Approved
0.6667	Remote Similarity	NPD1810	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6882	Approved
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6635	Remote Similarity	NPD7750	Discontinued
0.6613	Remote Similarity	NPD7492	Approved
0.6602	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6930	Phase 2
0.66	Remote Similarity	NPD6931	Approved
0.6598	Remote Similarity	NPD7339	Approved
0.6598	Remote Similarity	NPD6942	Approved
0.6596	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5988	Approved
0.6583	Remote Similarity	NPD6009	Approved
0.656	Remote Similarity	NPD6616	Approved
0.6557	Remote Similarity	NPD6319	Approved
0.6525	Remote Similarity	NPD8297	Approved
0.6514	Remote Similarity	NPD7991	Discontinued
0.6508	Remote Similarity	NPD7078	Approved
0.6504	Remote Similarity	NPD8516	Approved
0.6504	Remote Similarity	NPD8513	Phase 3
0.6504	Remote Similarity	NPD8515	Approved
0.6504	Remote Similarity	NPD8517	Approved
0.65	Remote Similarity	NPD7645	Phase 2
0.6496	Remote Similarity	NPD7625	Phase 1
0.6471	Remote Similarity	NPD4632	Approved
0.6465	Remote Similarity	NPD6925	Approved
0.6465	Remote Similarity	NPD5776	Phase 2
0.646	Remote Similarity	NPD7632	Discontinued
0.6446	Remote Similarity	NPD7115	Discovery
0.6435	Remote Similarity	NPD7128	Approved
0.6435	Remote Similarity	NPD6402	Approved
0.6435	Remote Similarity	NPD5739	Approved
0.6435	Remote Similarity	NPD6675	Approved
0.641	Remote Similarity	NPD6372	Approved
0.641	Remote Similarity	NPD6373	Approved
0.64	Remote Similarity	NPD7145	Approved
0.6389	Remote Similarity	NPD7087	Discontinued
0.6372	Remote Similarity	NPD4159	Approved
0.6364	Remote Similarity	NPD6933	Approved
0.6354	Remote Similarity	NPD2254	Approved
0.6354	Remote Similarity	NPD2686	Approved
0.6354	Remote Similarity	NPD2687	Approved
0.6339	Remote Similarity	NPD4225	Approved
0.633	Remote Similarity	NPD6399	Phase 3
0.6328	Remote Similarity	NPD6033	Approved
0.6325	Remote Similarity	NPD6899	Approved
0.6325	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6881	Approved
0.6325	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD5211	Phase 2
0.6303	Remote Similarity	NPD6650	Approved
0.6303	Remote Similarity	NPD6649	Approved
0.6286	Remote Similarity	NPD6893	Approved
0.6275	Remote Similarity	NPD7514	Phase 3
0.6275	Remote Similarity	NPD4748	Discontinued
0.625	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD3669	Approved
0.6239	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD7637	Suspended
0.6239	Remote Similarity	NPD5697	Approved
0.623	Remote Similarity	NPD6940	Discontinued
0.6218	Remote Similarity	NPD7290	Approved
0.6218	Remote Similarity	NPD6883	Approved
0.6218	Remote Similarity	NPD7102	Approved
0.6218	Remote Similarity	NPD4634	Approved
0.6214	Remote Similarity	NPD6902	Approved
0.6207	Remote Similarity	NPD5141	Approved
0.619	Remote Similarity	NPD4786	Approved
0.6186	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4202	Approved
0.6167	Remote Similarity	NPD6617	Approved
0.6167	Remote Similarity	NPD6869	Approved
0.6167	Remote Similarity	NPD6847	Approved
0.6167	Remote Similarity	NPD8130	Phase 1
0.6167	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6926	Approved
0.6162	Remote Similarity	NPD4785	Approved
0.6162	Remote Similarity	NPD4784	Approved
0.6162	Remote Similarity	NPD6924	Approved
0.6154	Remote Similarity	NPD6008	Approved
0.6142	Remote Similarity	NPD7604	Phase 2
0.614	Remote Similarity	NPD4700	Approved
0.614	Remote Similarity	NPD5285	Approved
0.614	Remote Similarity	NPD4696	Approved
0.614	Remote Similarity	NPD5286	Approved
0.6139	Remote Similarity	NPD6932	Approved
0.6134	Remote Similarity	NPD6014	Approved
0.6134	Remote Similarity	NPD6012	Approved
0.6134	Remote Similarity	NPD6013	Approved
0.6134	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4243	Approved
0.6117	Remote Similarity	NPD7332	Phase 2
0.6111	Remote Similarity	NPD5983	Phase 2
0.6106	Remote Similarity	NPD6084	Phase 2
0.6106	Remote Similarity	NPD6083	Phase 2
0.6095	Remote Similarity	NPD4788	Approved
0.6087	Remote Similarity	NPD5344	Discontinued
0.6078	Remote Similarity	NPD6118	Approved
0.6078	Remote Similarity	NPD6114	Approved
0.6078	Remote Similarity	NPD6697	Approved
0.6078	Remote Similarity	NPD6115	Approved
0.6058	Remote Similarity	NPD6898	Phase 1
0.6055	Remote Similarity	NPD6051	Approved
0.6055	Remote Similarity	NPD5328	Approved
0.605	Remote Similarity	NPD6011	Approved
0.605	Remote Similarity	NPD8174	Phase 2
0.6047	Remote Similarity	NPD6336	Discontinued
0.6034	Remote Similarity	NPD5224	Approved
0.6034	Remote Similarity	NPD5226	Approved
0.6034	Remote Similarity	NPD4633	Approved
0.6034	Remote Similarity	NPD5225	Approved
0.6033	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4787	Phase 1
0.6019	Remote Similarity	NPD6683	Phase 2
0.6017	Remote Similarity	NPD4767	Approved
0.6017	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD3168	Discontinued
0.5983	Remote Similarity	NPD5174	Approved
0.5983	Remote Similarity	NPD5175	Approved
0.598	Remote Similarity	NPD6116	Phase 1
0.5962	Remote Similarity	NPD7509	Discontinued
0.596	Remote Similarity	NPD7150	Approved
0.596	Remote Similarity	NPD7151	Approved
0.596	Remote Similarity	NPD7152	Approved
0.595	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5223	Approved
0.5946	Remote Similarity	NPD6079	Approved
0.5926	Remote Similarity	NPD3618	Phase 1
0.5918	Remote Similarity	NPD6923	Approved
0.5918	Remote Similarity	NPD6922	Approved
0.5917	Remote Similarity	NPD4730	Approved
0.5917	Remote Similarity	NPD4729	Approved
0.5913	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4753	Phase 2
0.5895	Remote Similarity	NPD371	Approved
0.5888	Remote Similarity	NPD3666	Approved
0.5888	Remote Similarity	NPD3133	Approved
0.5888	Remote Similarity	NPD3665	Phase 1
0.5882	Remote Similarity	NPD6117	Approved
0.5882	Remote Similarity	NPD6640	Phase 3
0.5878	Remote Similarity	NPD8074	Phase 3
0.5865	Remote Similarity	NPD5956	Approved
0.5859	Remote Similarity	NPD7143	Approved
0.5859	Remote Similarity	NPD7144	Approved
0.5859	Remote Similarity	NPD6921	Approved
0.5854	Remote Similarity	NPD6053	Discontinued
0.5847	Remote Similarity	NPD4754	Approved
0.5841	Remote Similarity	NPD7748	Approved
0.584	Remote Similarity	NPD6274	Approved
0.5827	Remote Similarity	NPD7100	Approved
0.5827	Remote Similarity	NPD7101	Approved
0.5826	Remote Similarity	NPD7902	Approved
0.582	Remote Similarity	NPD5249	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