NPASS Compound

Structure

CID106791 OpenBabel06191715452D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.4601 3.6251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4872 1.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3522 3.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2250 0.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2304 3.0988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1254 0.5332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1109 2.5905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 2.2524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7364 0.0947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7801 -0.1335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3750 1.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7140 2.8115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3444 0.5207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3300 2.5779 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3372 1.5492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0217 3.0797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6960 0.2584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1923 0.8106 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1182 1.5617 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -2.8916 -0.0965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1635 4.1828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3214 -0.6613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3038 0.8476 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 0.7160 2.9954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 6 1 0 0 0 0 4 13 2 0 0 0 0 5 7 1 0 0 0 0 6 19 1 0 0 0 0 7 19 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 24 1 0 0 0 0 10 18 1 0 0 0 0 10 20 1 0 0 0 0 11 18 1 6 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 14 5 1 6 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 6 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	780.28
Volume:	740.222
LogP:	0.577
LogD:	-0.114
LogS:	-2.808
# Rotatable Bonds:	15
TPSA:	291.82
# H-Bond Aceptor:	18
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.07
Synthetic Accessibility Score:	5.191
Fsp3:	0.568
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.715
MDCK Permeability:	2.4033099180087447e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.985
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	87.6307373046875%
Volume Distribution (VD):	0.183
Pgp-substrate:	14.199974060058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.27
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.108
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	1.909
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.649
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.605
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.949
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC106791

Natural Product ID:	NPC106791
*Common Name:**	BCJMNZRQJAVDLD-CQRYIUNCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BCJMNZRQJAVDLD-CQRYIUNCSA-N
Standard InCHI:	InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1
SMILES:	C/C=C1/C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496894
PubChem CID:	5281743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO7054	Dysphania ambrosioides	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7054	Dysphania ambrosioides	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17735	Acinetobacter genospecies	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25257	Menispermum fenestratum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25564	Ficus erecta	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15878	Dysidea incrustans	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7054	Dysphania ambrosioides	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28452	Rhododendron linearifolium	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18149	Linum paniculatum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21868	Rodgersia sambucifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22569	Micromonospora chersina	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24828	Pteraster tesselatus	Species	Pterasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25503	Anticarsia gemmatalis	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23012	Schizogyne glaberrima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20767	Hydnum imbricatum	Species	Hydnaceae	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	2
Potency	17

Activity Type	# Activity
Individual Protein	13
Organism	4
Others	1
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	22387.2	nM	PMID[523206]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	39810.7	nM	PMID[523207]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	50118.7	nM	PMID[523208]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[523208]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[523208]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	29934.9	nM	PMID[523206]
NPT1417	Individual Protein	Transcriptional regulator ERG	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[523208]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[523208]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	11885.6	nM	PMID[523207]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	8199.5	nM	PMID[523208]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	13335.9	nM	PMID[523207]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[523206]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[523207]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[523206]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[523208]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[523207]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[523209]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[523209]

☑ 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 NPC106791 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	113
0.1-0.2	784
0.2-0.3	4419
0.3-0.4	18104
0.4-0.5	12796
0.5-0.6	5418
0.6-0.7	1024
0.7-0.8	18
0.8-0.85	4
0.85-0.9	7
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201889
0.963	High Similarity	NPC130124
0.963	High Similarity	NPC193471
0.9286	High Similarity	NPC284656
0.9266	High Similarity	NPC47857
0.9266	High Similarity	NPC168758
0.9266	High Similarity	NPC181510
0.9091	High Similarity	NPC316984
0.9091	High Similarity	NPC30911
0.9043	High Similarity	NPC23963
0.8947	High Similarity	NPC235625
0.8889	High Similarity	NPC64168
0.8796	High Similarity	NPC173690
0.8796	High Similarity	NPC6271
0.8796	High Similarity	NPC279833
0.8796	High Similarity	NPC80439
0.8509	High Similarity	NPC275100
0.8348	Intermediate Similarity	NPC474497
0.8333	Intermediate Similarity	NPC196073
0.8333	Intermediate Similarity	NPC195435
0.8	Intermediate Similarity	NPC200412
0.8	Intermediate Similarity	NPC120599
0.8	Intermediate Similarity	NPC156336
0.7304	Intermediate Similarity	NPC471144
0.7258	Intermediate Similarity	NPC30196
0.7236	Intermediate Similarity	NPC469597
0.7203	Intermediate Similarity	NPC475871
0.7203	Intermediate Similarity	NPC475945
0.72	Intermediate Similarity	NPC6531
0.7165	Intermediate Similarity	NPC230849
0.7154	Intermediate Similarity	NPC261750
0.7154	Intermediate Similarity	NPC1111
0.7143	Intermediate Similarity	NPC316401
0.7132	Intermediate Similarity	NPC318445
0.7132	Intermediate Similarity	NPC316133
0.7119	Intermediate Similarity	NPC474747
0.7073	Intermediate Similarity	NPC474411
0.7073	Intermediate Similarity	NPC474431
0.7049	Intermediate Similarity	NPC38154
0.7045	Intermediate Similarity	NPC471086
0.7034	Intermediate Similarity	NPC474742
0.7023	Intermediate Similarity	NPC474371
0.7016	Intermediate Similarity	NPC60432
0.7	Intermediate Similarity	NPC474741
0.6975	Remote Similarity	NPC149371
0.697	Remote Similarity	NPC314282
0.6967	Remote Similarity	NPC474099
0.6963	Remote Similarity	NPC133089
0.6949	Remote Similarity	NPC475949
0.6947	Remote Similarity	NPC326386
0.6947	Remote Similarity	NPC477985
0.6947	Remote Similarity	NPC471087
0.694	Remote Similarity	NPC477988
0.6917	Remote Similarity	NPC472755
0.6917	Remote Similarity	NPC474827
0.6917	Remote Similarity	NPC68001
0.6917	Remote Similarity	NPC474828
0.6917	Remote Similarity	NPC199831
0.6912	Remote Similarity	NPC120420
0.6897	Remote Similarity	NPC471142
0.6891	Remote Similarity	NPC185141
0.6891	Remote Similarity	NPC46998
0.6891	Remote Similarity	NPC110443
0.6891	Remote Similarity	NPC47880
0.6891	Remote Similarity	NPC472753
0.6891	Remote Similarity	NPC133907
0.6891	Remote Similarity	NPC128733
0.6889	Remote Similarity	NPC120335
0.6885	Remote Similarity	NPC477513
0.687	Remote Similarity	NPC81419
0.687	Remote Similarity	NPC475912
0.687	Remote Similarity	NPC179746
0.6864	Remote Similarity	NPC473326
0.6861	Remote Similarity	NPC99864
0.686	Remote Similarity	NPC100487
0.686	Remote Similarity	NPC203659
0.6842	Remote Similarity	NPC473619
0.6842	Remote Similarity	NPC204556
0.6838	Remote Similarity	NPC477921
0.6833	Remote Similarity	NPC473289
0.6833	Remote Similarity	NPC472754
0.6818	Remote Similarity	NPC313342
0.6818	Remote Similarity	NPC313333
0.6818	Remote Similarity	NPC314512
0.6818	Remote Similarity	NPC314451
0.6807	Remote Similarity	NPC288876
0.6797	Remote Similarity	NPC65045
0.6783	Remote Similarity	NPC184463
0.6783	Remote Similarity	NPC30515
0.6783	Remote Similarity	NPC12172
0.6783	Remote Similarity	NPC473321
0.6783	Remote Similarity	NPC208886
0.678	Remote Similarity	NPC476344
0.6777	Remote Similarity	NPC110989
0.6777	Remote Similarity	NPC475873
0.6769	Remote Similarity	NPC11379
0.6767	Remote Similarity	NPC329401
0.6767	Remote Similarity	NPC477987
0.6752	Remote Similarity	NPC36954
0.6752	Remote Similarity	NPC477922
0.6752	Remote Similarity	NPC14961
0.6752	Remote Similarity	NPC150041
0.6752	Remote Similarity	NPC270013
0.675	Remote Similarity	NPC474339
0.675	Remote Similarity	NPC201718
0.675	Remote Similarity	NPC164598
0.675	Remote Similarity	NPC476270
0.6748	Remote Similarity	NPC26617
0.6748	Remote Similarity	NPC474285
0.6748	Remote Similarity	NPC254538
0.6748	Remote Similarity	NPC271562
0.6742	Remote Similarity	NPC477989
0.6742	Remote Similarity	NPC323168
0.6742	Remote Similarity	NPC477990
0.6742	Remote Similarity	NPC314629
0.6742	Remote Similarity	NPC293550
0.6742	Remote Similarity	NPC111162
0.6741	Remote Similarity	NPC315387
0.6741	Remote Similarity	NPC316205
0.6724	Remote Similarity	NPC212486
0.6724	Remote Similarity	NPC476300
0.672	Remote Similarity	NPC469603
0.6718	Remote Similarity	NPC475383
0.6718	Remote Similarity	NPC156379
0.6696	Remote Similarity	NPC51004
0.6696	Remote Similarity	NPC474761
0.6696	Remote Similarity	NPC476004
0.6695	Remote Similarity	NPC17585
0.6695	Remote Similarity	NPC476009
0.6695	Remote Similarity	NPC473859
0.6694	Remote Similarity	NPC225353
0.6694	Remote Similarity	NPC471148
0.6694	Remote Similarity	NPC474244
0.6692	Remote Similarity	NPC241050
0.6691	Remote Similarity	NPC215507
0.6691	Remote Similarity	NPC307165
0.6667	Remote Similarity	NPC475832
0.6667	Remote Similarity	NPC81386
0.6667	Remote Similarity	NPC474035
0.6667	Remote Similarity	NPC469632
0.6667	Remote Similarity	NPC475642
0.6667	Remote Similarity	NPC243998
0.6667	Remote Similarity	NPC202672
0.6667	Remote Similarity	NPC475927
0.6642	Remote Similarity	NPC309525
0.6641	Remote Similarity	NPC103391
0.6641	Remote Similarity	NPC472536
0.6639	Remote Similarity	NPC52820
0.6637	Remote Similarity	NPC469861
0.6637	Remote Similarity	NPC469860
0.6637	Remote Similarity	NPC130436
0.6619	Remote Similarity	NPC471256
0.6615	Remote Similarity	NPC174463
0.6612	Remote Similarity	NPC188785
0.661	Remote Similarity	NPC475659
0.661	Remote Similarity	NPC475900
0.6609	Remote Similarity	NPC295312
0.6609	Remote Similarity	NPC307411
0.6593	Remote Similarity	NPC476951
0.6591	Remote Similarity	NPC470000
0.6587	Remote Similarity	NPC5103
0.6585	Remote Similarity	NPC472756
0.6583	Remote Similarity	NPC187268
0.6583	Remote Similarity	NPC208233
0.6581	Remote Similarity	NPC469645
0.6581	Remote Similarity	NPC273579
0.6581	Remote Similarity	NPC469692
0.6581	Remote Similarity	NPC295204
0.6581	Remote Similarity	NPC288240
0.6581	Remote Similarity	NPC162205
0.6579	Remote Similarity	NPC52533
0.6571	Remote Similarity	NPC243902
0.6565	Remote Similarity	NPC471261
0.656	Remote Similarity	NPC70235
0.656	Remote Similarity	NPC475960
0.6557	Remote Similarity	NPC86077
0.6557	Remote Similarity	NPC320019
0.6557	Remote Similarity	NPC324017
0.6555	Remote Similarity	NPC158416
0.6555	Remote Similarity	NPC476315
0.6555	Remote Similarity	NPC470883
0.6555	Remote Similarity	NPC39859
0.6555	Remote Similarity	NPC76862
0.6552	Remote Similarity	NPC473448
0.6549	Remote Similarity	NPC21469
0.6544	Remote Similarity	NPC173173
0.6538	Remote Similarity	NPC471145
0.6538	Remote Similarity	NPC471146
0.6535	Remote Similarity	NPC58281
0.6532	Remote Similarity	NPC223450
0.6529	Remote Similarity	NPC477512
0.6525	Remote Similarity	NPC476267
0.6525	Remote Similarity	NPC140543
0.6525	Remote Similarity	NPC121825
0.6525	Remote Similarity	NPC473316
0.6525	Remote Similarity	NPC473330
0.6522	Remote Similarity	NPC90814
0.6522	Remote Similarity	NPC189393
0.6522	Remote Similarity	NPC473715
0.6522	Remote Similarity	NPC89001

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 NPC106791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	92
0.1-0.2	683
0.2-0.3	3149
0.3-0.4	3703
0.4-0.5	1191
0.5-0.6	298
0.6-0.7	33
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD2204	Approved
0.7132	Intermediate Similarity	NPD7642	Approved
0.7054	Intermediate Similarity	NPD8080	Discontinued
0.7023	Intermediate Similarity	NPD8451	Approved
0.6977	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8448	Approved
0.6934	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD8415	Approved
0.6818	Remote Similarity	NPD8341	Approved
0.6818	Remote Similarity	NPD8299	Approved
0.6818	Remote Similarity	NPD8342	Approved
0.6818	Remote Similarity	NPD8340	Approved
0.6815	Remote Similarity	NPD8392	Approved
0.6815	Remote Similarity	NPD8390	Approved
0.6815	Remote Similarity	NPD8391	Approved
0.6748	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7641	Discontinued
0.6642	Remote Similarity	NPD8273	Phase 1
0.6493	Remote Similarity	NPD7830	Approved
0.6493	Remote Similarity	NPD7829	Approved
0.6475	Remote Similarity	NPD6845	Suspended
0.6463	Remote Similarity	NPD2575	Approved
0.6458	Remote Similarity	NPD8384	Approved
0.6308	Remote Similarity	NPD1376	Discontinued
0.6286	Remote Similarity	NPD7260	Phase 2
0.6234	Remote Similarity	NPD8414	Discontinued
0.6222	Remote Similarity	NPD8444	Approved
0.6202	Remote Similarity	NPD6371	Approved
0.6202	Remote Similarity	NPD6421	Discontinued
0.6198	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD8337	Approved
0.6187	Remote Similarity	NPD8336	Approved
0.6134	Remote Similarity	NPD46	Approved
0.6134	Remote Similarity	NPD6698	Approved
0.6127	Remote Similarity	NPD2613	Approved
0.6111	Remote Similarity	NPD3615	Approved
0.6111	Remote Similarity	NPD4745	Approved
0.6111	Remote Similarity	NPD3614	Approved
0.6111	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3088	Approved
0.6111	Remote Similarity	NPD2566	Approved
0.6111	Remote Similarity	NPD2571	Approved
0.6111	Remote Similarity	NPD3089	Approved
0.6111	Remote Similarity	NPD4746	Phase 3
0.6111	Remote Similarity	NPD2574	Discontinued
0.6111	Remote Similarity	NPD3087	Approved
0.6111	Remote Similarity	NPD2573	Approved
0.6111	Remote Similarity	NPD3616	Approved
0.6111	Remote Similarity	NPD2570	Approved
0.6111	Remote Similarity	NPD3090	Approved
0.6103	Remote Similarity	NPD6921	Approved
0.6083	Remote Similarity	NPD7983	Approved
0.6078	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD4684	Phase 3
0.6027	Remote Similarity	NPD4686	Approved
0.6027	Remote Similarity	NPD4685	Phase 3
0.6016	Remote Similarity	NPD4228	Discovery
0.6014	Remote Similarity	NPD8338	Approved
0.6	Remote Similarity	NPD7838	Discovery
0.5985	Remote Similarity	NPD6909	Approved
0.5985	Remote Similarity	NPD6908	Approved
0.5984	Remote Similarity	NPD8275	Approved
0.5984	Remote Similarity	NPD8276	Approved
0.5969	Remote Similarity	NPD8140	Approved
0.5944	Remote Similarity	NPD3661	Approved
0.5944	Remote Similarity	NPD3663	Approved
0.5944	Remote Similarity	NPD3662	Phase 3
0.5944	Remote Similarity	NPD3664	Approved
0.5923	Remote Similarity	NPD6686	Approved
0.592	Remote Similarity	NPD4225	Approved
0.5918	Remote Similarity	NPD6333	Approved
0.5918	Remote Similarity	NPD6334	Approved
0.5906	Remote Similarity	NPD8086	Approved
0.5906	Remote Similarity	NPD8084	Approved
0.5906	Remote Similarity	NPD8083	Approved
0.5906	Remote Similarity	NPD8082	Approved
0.5906	Remote Similarity	NPD8138	Approved
0.5906	Remote Similarity	NPD8139	Approved
0.5906	Remote Similarity	NPD8085	Approved
0.5891	Remote Similarity	NPD4211	Phase 1
0.5891	Remote Similarity	NPD8393	Approved
0.5887	Remote Similarity	NPD8074	Phase 3
0.5882	Remote Similarity	NPD1773	Discontinued
0.5854	Remote Similarity	NPD5282	Discontinued
0.5847	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD8307	Discontinued
0.5814	Remote Similarity	NPD8081	Approved
0.5804	Remote Similarity	NPD376	Approved
0.5804	Remote Similarity	NPD11	Approved
0.5789	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1719	Phase 1
0.5764	Remote Similarity	NPD6914	Discontinued
0.5746	Remote Similarity	NPD6053	Discontinued
0.5736	Remote Similarity	NPD1407	Approved
0.5726	Remote Similarity	NPD883	Phase 2
0.5726	Remote Similarity	NPD882	Phase 2
0.5725	Remote Similarity	NPD3159	Discontinued
0.5725	Remote Similarity	NPD2495	Phase 3
0.5724	Remote Similarity	NPD5204	Approved
0.5714	Remote Similarity	NPD6420	Discontinued
0.5714	Remote Similarity	NPD4621	Approved
0.5714	Remote Similarity	NPD4619	Approved
0.5714	Remote Similarity	NPD8087	Discontinued
0.5703	Remote Similarity	NPD5344	Discontinued
0.5694	Remote Similarity	NPD2159	Approved
0.5694	Remote Similarity	NPD2627	Approved
0.5694	Remote Similarity	NPD2625	Approved
0.5694	Remote Similarity	NPD2628	Approved
0.5694	Remote Similarity	NPD2160	Approved
0.5694	Remote Similarity	NPD7319	Approved
0.5694	Remote Similarity	NPD2626	Approved
0.5693	Remote Similarity	NPD7505	Discontinued
0.5683	Remote Similarity	NPD6319	Approved
0.5683	Remote Similarity	NPD2645	Approved
0.5678	Remote Similarity	NPD6110	Phase 1
0.5667	Remote Similarity	NPD4249	Approved
0.5664	Remote Similarity	NPD1452	Discontinued
0.5659	Remote Similarity	NPD8301	Approved
0.5659	Remote Similarity	NPD8300	Approved
0.5656	Remote Similarity	NPD1695	Approved
0.5649	Remote Similarity	NPD777	Phase 3
0.5645	Remote Similarity	NPD5779	Approved
0.5645	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD5778	Approved
0.5643	Remote Similarity	NPD8513	Phase 3
0.5643	Remote Similarity	NPD8515	Approved
0.5643	Remote Similarity	NPD8268	Approved
0.5643	Remote Similarity	NPD8269	Approved
0.5643	Remote Similarity	NPD8516	Approved
0.5643	Remote Similarity	NPD8266	Approved
0.5643	Remote Similarity	NPD8267	Approved
0.5643	Remote Similarity	NPD8517	Approved
0.5639	Remote Similarity	NPD8305	Approved
0.5639	Remote Similarity	NPD8306	Approved
0.5638	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD4217	Approved
0.5634	Remote Similarity	NPD2610	Approved
0.5634	Remote Similarity	NPD2608	Approved
0.5634	Remote Similarity	NPD3131	Approved
0.5634	Remote Similarity	NPD3132	Approved
0.5634	Remote Similarity	NPD4216	Approved
0.5634	Remote Similarity	NPD4218	Approved
0.5634	Remote Similarity	NPD4215	Approved
0.5634	Remote Similarity	NPD2612	Approved
0.5634	Remote Similarity	NPD2609	Approved
0.5634	Remote Similarity	NPD7492	Approved
0.5634	Remote Similarity	NPD2611	Approved
0.562	Remote Similarity	NPD4251	Approved
0.562	Remote Similarity	NPD4250	Approved
0.5616	Remote Similarity	NPD2101	Approved
0.5603	Remote Similarity	NPD7623	Phase 3
0.5603	Remote Similarity	NPD7624	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