NPASS Compound

Structure

CID229600 OpenBabel06191716022D 38 41 0 0 1 0 0 0 0 0999 V2000 -7.3902 0.8146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 -5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4948 1.8092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4767 0.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 -4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6858 2.3970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6677 0.9957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9632 2.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0497 2.1713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2226 1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7722 1.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -3.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2406 2.7591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -3.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 -1.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0570 -2.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7891 -2.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0570 -5.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3452 3.7536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 1.9456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3271 2.3523 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 1.7891 -3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 28 1 0 0 0 0 14 18 1 0 0 0 0 14 34 1 0 0 0 0 15 27 1 0 0 0 0 15 35 1 0 0 0 0 16 27 1 0 0 0 0 16 36 1 0 0 0 0 19 13 1 6 0 0 0 19 21 1 0 0 0 0 19 37 1 0 0 0 0 20 29 2 0 0 0 0 20 35 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 38 1 6 0 0 0 24 26 1 0 0 0 0 24 27 1 6 0 0 0 24 32 1 0 0 0 0 25 34 1 6 0 0 0 25 37 1 0 0 0 0 26 36 1 0 0 0 0 26 38 1 1 0 0 0 27 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.19
Volume:	516.923
LogP:	1.506
LogD:	1.469
LogS:	-3.667
# Rotatable Bonds:	11
TPSA:	164.37
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	4.334
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
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:	-5.519
MDCK Permeability:	1.2937127394252457e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.799
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	89.2401351928711%
Volume Distribution (VD):	0.447
Pgp-substrate:	8.330886840820312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	1.063
Half-life (T1/2):	0.726

ADMET: Toxicity

hERG Blockers:	0.16
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.451
AMES Toxicity:	0.502
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.663
Carcinogencity:	0.236
Eye Corrosion:	0.003
Eye Irritation:	0.101
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC229600

Natural Product ID:	NPC229600
*Common Name:**	Visartiside E
IUPAC Name:	[(3S,4R,5S)-5-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (E)-3-phenylprop-2-enoate
Synonyms:	Visartiside E
Standard InCHIKey:	MHNSACWVEAXCGK-JVYJMAPHSA-N
Standard InCHI:	InChI=1S/C27H32O11/c28-13-19-21(30)23(22(31)25(37-19)34-14-18-9-5-2-6-10-18)38-26-24(32)27(33,16-36-26)15-35-20(29)12-11-17-7-3-1-4-8-17/h1-12,19,21-26,28,30-33H,13-16H2/b12-11+/t19-,21-,22-,23+,24+,25-,26+,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OCc2ccccc2)[C@@H]([C@H]([C@@H]1O)O[C@@H]1OC[C@]([C@H]1O)(O)COC(=O)/C=C/c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1082561
PubChem CID:	46184806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(02)00231-5]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12377236]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121165]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO539	Picea vulgaris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14062	Oophaga speciosa	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16561	Viscum articulatum	Species	Viscaceae	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	=	39600.0	nM	PMID[506167]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	88.1	%	PMID[506167]
NPT1	Others	Radical scavenging activity		ED50	>	100.0	uM	PMID[506167]

☑ 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 NPC229600 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	234
0.1-0.2	1003
0.2-0.3	2595
0.3-0.4	7267
0.4-0.5	11688
0.5-0.6	14004
0.6-0.7	4791
0.7-0.8	1028
0.8-0.85	73
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9027	High Similarity	NPC264784
0.9027	High Similarity	NPC43584
0.896	High Similarity	NPC478255
0.8943	High Similarity	NPC148026
0.8871	High Similarity	NPC225307
0.8862	High Similarity	NPC114096
0.885	High Similarity	NPC184633
0.8793	High Similarity	NPC474641
0.8783	High Similarity	NPC470825
0.8772	High Similarity	NPC474148
0.8772	High Similarity	NPC276061
0.872	High Similarity	NPC301857
0.8696	High Similarity	NPC30563
0.8661	High Similarity	NPC138777
0.8661	High Similarity	NPC225384
0.8661	High Similarity	NPC246869
0.864	High Similarity	NPC288416
0.8584	High Similarity	NPC37714
0.8584	High Similarity	NPC152384
0.8527	High Similarity	NPC28637
0.8516	High Similarity	NPC235294
0.8516	High Similarity	NPC46137
0.8496	Intermediate Similarity	NPC148060
0.8492	Intermediate Similarity	NPC471882
0.8492	Intermediate Similarity	NPC471881
0.8492	Intermediate Similarity	NPC156692
0.8492	Intermediate Similarity	NPC45224
0.8492	Intermediate Similarity	NPC106677
0.8492	Intermediate Similarity	NPC173150
0.8492	Intermediate Similarity	NPC35288
0.8485	Intermediate Similarity	NPC328273
0.8485	Intermediate Similarity	NPC171134
0.8485	Intermediate Similarity	NPC321638
0.8485	Intermediate Similarity	NPC321184
0.848	Intermediate Similarity	NPC83218
0.848	Intermediate Similarity	NPC126991
0.8413	Intermediate Similarity	NPC61181
0.8413	Intermediate Similarity	NPC471157
0.8413	Intermediate Similarity	NPC252114
0.84	Intermediate Similarity	NPC57607
0.84	Intermediate Similarity	NPC145287
0.839	Intermediate Similarity	NPC265002
0.8387	Intermediate Similarity	NPC52097
0.837	Intermediate Similarity	NPC478250
0.8346	Intermediate Similarity	NPC103533
0.8333	Intermediate Similarity	NPC47286
0.8306	Intermediate Similarity	NPC11724
0.8305	Intermediate Similarity	NPC185840
0.8305	Intermediate Similarity	NPC234376
0.8268	Intermediate Similarity	NPC276047
0.8268	Intermediate Similarity	NPC267733
0.8258	Intermediate Similarity	NPC263829
0.8246	Intermediate Similarity	NPC469527
0.824	Intermediate Similarity	NPC141970
0.824	Intermediate Similarity	NPC140561
0.8235	Intermediate Similarity	NPC105005
0.8235	Intermediate Similarity	NPC40305
0.8226	Intermediate Similarity	NPC476872
0.8217	Intermediate Similarity	NPC11025
0.8203	Intermediate Similarity	NPC471025
0.8203	Intermediate Similarity	NPC175333
0.8197	Intermediate Similarity	NPC216605
0.8197	Intermediate Similarity	NPC266389
0.8197	Intermediate Similarity	NPC122245
0.8195	Intermediate Similarity	NPC166180
0.8195	Intermediate Similarity	NPC471345
0.8182	Intermediate Similarity	NPC34293
0.8182	Intermediate Similarity	NPC886
0.8182	Intermediate Similarity	NPC287597
0.8175	Intermediate Similarity	NPC296954
0.8175	Intermediate Similarity	NPC300894
0.8175	Intermediate Similarity	NPC141455
0.8175	Intermediate Similarity	NPC110063
0.8175	Intermediate Similarity	NPC232454
0.8175	Intermediate Similarity	NPC196063
0.8175	Intermediate Similarity	NPC178449
0.8175	Intermediate Similarity	NPC470907
0.8168	Intermediate Similarity	NPC473924
0.814	Intermediate Similarity	NPC146540
0.814	Intermediate Similarity	NPC471024
0.8134	Intermediate Similarity	NPC78363
0.8134	Intermediate Similarity	NPC260425
0.812	Intermediate Similarity	NPC277788
0.811	Intermediate Similarity	NPC244454
0.811	Intermediate Similarity	NPC87153
0.811	Intermediate Similarity	NPC162925
0.8106	Intermediate Similarity	NPC254398
0.8099	Intermediate Similarity	NPC29607
0.8095	Intermediate Similarity	NPC471067
0.8092	Intermediate Similarity	NPC219677
0.8092	Intermediate Similarity	NPC281798
0.8092	Intermediate Similarity	NPC254819
0.8088	Intermediate Similarity	NPC134405
0.8088	Intermediate Similarity	NPC476385
0.8088	Intermediate Similarity	NPC476442
0.8088	Intermediate Similarity	NPC215512
0.8077	Intermediate Similarity	NPC295970
0.8077	Intermediate Similarity	NPC253595
0.8077	Intermediate Similarity	NPC27712
0.8074	Intermediate Similarity	NPC472350
0.8074	Intermediate Similarity	NPC476383
0.8074	Intermediate Similarity	NPC205195
0.8074	Intermediate Similarity	NPC81515
0.8074	Intermediate Similarity	NPC64141
0.8074	Intermediate Similarity	NPC68092
0.8074	Intermediate Similarity	NPC197316
0.8074	Intermediate Similarity	NPC89105
0.8071	Intermediate Similarity	NPC469448
0.8058	Intermediate Similarity	NPC229505
0.8047	Intermediate Similarity	NPC476033
0.8047	Intermediate Similarity	NPC77651
0.8047	Intermediate Similarity	NPC28069
0.8045	Intermediate Similarity	NPC471883
0.8034	Intermediate Similarity	NPC472315
0.8034	Intermediate Similarity	NPC475203
0.8034	Intermediate Similarity	NPC474376
0.8034	Intermediate Similarity	NPC472316
0.8029	Intermediate Similarity	NPC222433
0.8029	Intermediate Similarity	NPC265648
0.8017	Intermediate Similarity	NPC120217
0.8015	Intermediate Similarity	NPC17567
0.7986	Intermediate Similarity	NPC216819
0.7986	Intermediate Similarity	NPC262182
0.7986	Intermediate Similarity	NPC83743
0.7986	Intermediate Similarity	NPC287615
0.7985	Intermediate Similarity	NPC476870
0.7984	Intermediate Similarity	NPC63404
0.7984	Intermediate Similarity	NPC198918
0.7984	Intermediate Similarity	NPC10121
0.7984	Intermediate Similarity	NPC231888
0.7984	Intermediate Similarity	NPC124878
0.7984	Intermediate Similarity	NPC204214
0.7984	Intermediate Similarity	NPC92283
0.7984	Intermediate Similarity	NPC290276
0.7984	Intermediate Similarity	NPC35338
0.7984	Intermediate Similarity	NPC10883
0.7971	Intermediate Similarity	NPC302286
0.7971	Intermediate Similarity	NPC237872
0.7971	Intermediate Similarity	NPC471139
0.7971	Intermediate Similarity	NPC116104
0.7971	Intermediate Similarity	NPC88754
0.7971	Intermediate Similarity	NPC263397
0.7958	Intermediate Similarity	NPC188393
0.7958	Intermediate Similarity	NPC470934
0.7956	Intermediate Similarity	NPC476377
0.7956	Intermediate Similarity	NPC186406
0.7956	Intermediate Similarity	NPC47471
0.7941	Intermediate Similarity	NPC49597
0.7939	Intermediate Similarity	NPC477293
0.7939	Intermediate Similarity	NPC477294
0.7939	Intermediate Similarity	NPC229784
0.7937	Intermediate Similarity	NPC476445
0.7937	Intermediate Similarity	NPC476448
0.7937	Intermediate Similarity	NPC469703
0.7937	Intermediate Similarity	NPC469704
0.7937	Intermediate Similarity	NPC160854
0.7937	Intermediate Similarity	NPC201402
0.7937	Intermediate Similarity	NPC469548
0.7923	Intermediate Similarity	NPC231627
0.7923	Intermediate Similarity	NPC469687
0.7923	Intermediate Similarity	NPC230331
0.7914	Intermediate Similarity	NPC471028
0.791	Intermediate Similarity	NPC169398
0.7907	Intermediate Similarity	NPC470510
0.7907	Intermediate Similarity	NPC79608
0.7899	Intermediate Similarity	NPC140502
0.7899	Intermediate Similarity	NPC65833
0.7899	Intermediate Similarity	NPC145319
0.7899	Intermediate Similarity	NPC31081
0.7899	Intermediate Similarity	NPC245219
0.7895	Intermediate Similarity	NPC473285
0.7895	Intermediate Similarity	NPC262826
0.7891	Intermediate Similarity	NPC470815
0.7891	Intermediate Similarity	NPC138798
0.7883	Intermediate Similarity	NPC475530
0.7883	Intermediate Similarity	NPC473799
0.7881	Intermediate Similarity	NPC136962
0.7881	Intermediate Similarity	NPC37115
0.7879	Intermediate Similarity	NPC289415
0.7879	Intermediate Similarity	NPC319995
0.7874	Intermediate Similarity	NPC469686
0.7868	Intermediate Similarity	NPC476376
0.7868	Intermediate Similarity	NPC475195
0.7863	Intermediate Similarity	NPC232880
0.7863	Intermediate Similarity	NPC280616
0.7863	Intermediate Similarity	NPC242913
0.7863	Intermediate Similarity	NPC237182
0.7863	Intermediate Similarity	NPC226101
0.7863	Intermediate Similarity	NPC171831
0.7857	Intermediate Similarity	NPC282409
0.7857	Intermediate Similarity	NPC138915
0.7857	Intermediate Similarity	NPC476382
0.7857	Intermediate Similarity	NPC34587
0.7857	Intermediate Similarity	NPC100998
0.7857	Intermediate Similarity	NPC469702
0.7857	Intermediate Similarity	NPC252292
0.7857	Intermediate Similarity	NPC34927
0.7847	Intermediate Similarity	NPC34066
0.7847	Intermediate Similarity	NPC469422
0.7842	Intermediate Similarity	NPC476380

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 NPC229600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	658
0.2-0.3	1340
0.3-0.4	3148
0.4-0.5	2501
0.5-0.6	1125
0.6-0.7	179
0.7-0.8	8
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8305	Intermediate Similarity	NPD969	Suspended
0.8145	Intermediate Similarity	NPD5126	Approved
0.8145	Intermediate Similarity	NPD5125	Phase 3
0.8074	Intermediate Similarity	NPD7266	Discontinued
0.763	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1091	Approved
0.731	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4198	Discontinued
0.7162	Intermediate Similarity	NPD1653	Approved
0.7103	Intermediate Similarity	NPD6190	Approved
0.7092	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD689	Discontinued
0.7039	Intermediate Similarity	NPD8455	Phase 2
0.7023	Intermediate Similarity	NPD7741	Discontinued
0.7	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1238	Approved
0.6939	Remote Similarity	NPD5058	Phase 3
0.6914	Remote Similarity	NPD7685	Pre-registration
0.6911	Remote Similarity	NPD6647	Phase 2
0.6903	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7799	Discontinued
0.6853	Remote Similarity	NPD7097	Phase 1
0.6832	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4404	Approved
0.68	Remote Similarity	NPD5048	Discontinued
0.6797	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3764	Approved
0.6735	Remote Similarity	NPD1652	Phase 2
0.6719	Remote Similarity	NPD2067	Discontinued
0.6718	Remote Similarity	NPD2629	Approved
0.6718	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7876	Discontinued
0.6713	Remote Similarity	NPD4340	Discontinued
0.6707	Remote Similarity	NPD6559	Discontinued
0.6693	Remote Similarity	NPD1358	Approved
0.669	Remote Similarity	NPD6233	Phase 2
0.669	Remote Similarity	NPD7033	Discontinued
0.6689	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD7228	Approved
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD7798	Approved
0.6645	Remote Similarity	NPD37	Approved
0.6645	Remote Similarity	NPD5403	Approved
0.6644	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2182	Approved
0.664	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8312	Approved
0.6627	Remote Similarity	NPD8313	Approved
0.6624	Remote Similarity	NPD4967	Phase 2
0.6624	Remote Similarity	NPD4965	Approved
0.6624	Remote Similarity	NPD4966	Approved
0.6623	Remote Similarity	NPD5401	Approved
0.6621	Remote Similarity	NPD41	Approved
0.6621	Remote Similarity	NPD5886	Approved
0.6614	Remote Similarity	NPD6685	Approved
0.6597	Remote Similarity	NPD5124	Phase 1
0.6597	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD9495	Approved
0.6581	Remote Similarity	NPD1282	Approved
0.6575	Remote Similarity	NPD5588	Approved
0.6548	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD3225	Approved
0.6544	Remote Similarity	NPD5723	Approved
0.6541	Remote Similarity	NPD6234	Discontinued
0.6536	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7054	Approved
0.6524	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD9545	Approved
0.6516	Remote Similarity	NPD4380	Phase 2
0.651	Remote Similarity	NPD6674	Discontinued
0.6508	Remote Similarity	NPD5765	Approved
0.6506	Remote Similarity	NPD7240	Approved
0.6503	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6798	Discontinued
0.6497	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7236	Approved
0.6489	Remote Similarity	NPD6912	Phase 3
0.6488	Remote Similarity	NPD8407	Phase 2
0.6486	Remote Similarity	NPD5763	Approved
0.6486	Remote Similarity	NPD5762	Approved
0.6485	Remote Similarity	NPD7472	Approved
0.6485	Remote Similarity	NPD7074	Phase 3
0.6484	Remote Similarity	NPD3134	Approved
0.6483	Remote Similarity	NPD6355	Discontinued
0.6483	Remote Similarity	NPD1933	Approved
0.6478	Remote Similarity	NPD7075	Discontinued
0.6467	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2575	Approved
0.646	Remote Similarity	NPD7199	Phase 2
0.6457	Remote Similarity	NPD5909	Discontinued
0.6457	Remote Similarity	NPD1237	Approved
0.6456	Remote Similarity	NPD5402	Approved
0.6453	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3705	Approved
0.6439	Remote Similarity	NPD7843	Approved
0.6438	Remote Similarity	NPD6653	Approved
0.6434	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD290	Approved
0.6434	Remote Similarity	NPD7095	Approved
0.6434	Remote Similarity	NPD6686	Approved
0.6434	Remote Similarity	NPD3027	Phase 3
0.6429	Remote Similarity	NPD5667	Approved
0.6415	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6310	Approved
0.6414	Remote Similarity	NPD1613	Approved
0.6414	Remote Similarity	NPD6309	Approved
0.6414	Remote Similarity	NPD6311	Approved
0.6408	Remote Similarity	NPD5204	Approved
0.6407	Remote Similarity	NPD8368	Discontinued
0.6407	Remote Similarity	NPD7251	Discontinued
0.6395	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4538	Approved
0.6395	Remote Similarity	NPD4536	Approved
0.6393	Remote Similarity	NPD1202	Approved
0.6387	Remote Similarity	NPD7239	Suspended
0.6383	Remote Similarity	NPD2626	Approved
0.6383	Remote Similarity	NPD2625	Approved
0.6383	Remote Similarity	NPD2159	Approved
0.6383	Remote Similarity	NPD2160	Approved
0.6383	Remote Similarity	NPD2627	Approved
0.6383	Remote Similarity	NPD2628	Approved
0.6377	Remote Similarity	NPD4106	Approved
0.6377	Remote Similarity	NPD4135	Approved
0.6377	Remote Similarity	NPD4136	Approved
0.6376	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.637	Remote Similarity	NPD5291	Approved
0.637	Remote Similarity	NPD5292	Approved
0.6369	Remote Similarity	NPD7808	Phase 3
0.6364	Remote Similarity	NPD4617	Approved
0.6364	Remote Similarity	NPD4620	Approved
0.6364	Remote Similarity	NPD6832	Phase 2
0.6364	Remote Similarity	NPD5201	Approved
0.6364	Remote Similarity	NPD5203	Approved
0.6358	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5960	Phase 3
0.635	Remote Similarity	NPD1357	Approved
0.635	Remote Similarity	NPD7503	Approved
0.6347	Remote Similarity	NPD6797	Phase 2
0.6345	Remote Similarity	NPD4062	Phase 3
0.634	Remote Similarity	NPD6799	Approved
0.6338	Remote Similarity	NPD7247	Discontinued
0.6336	Remote Similarity	NPD5236	Approved
0.6336	Remote Similarity	NPD5237	Approved
0.6336	Remote Similarity	NPD5240	Approved
0.6336	Remote Similarity	NPD5235	Approved
0.6336	Remote Similarity	NPD5239	Approved
0.6333	Remote Similarity	NPD2424	Discontinued
0.6331	Remote Similarity	NPD4807	Approved
0.6331	Remote Similarity	NPD4806	Approved
0.6329	Remote Similarity	NPD6801	Discontinued
0.6328	Remote Similarity	NPD164	Approved
0.632	Remote Similarity	NPD5926	Approved
0.6319	Remote Similarity	NPD7008	Discontinued
0.6316	Remote Similarity	NPD5535	Approved
0.6304	Remote Similarity	NPD5305	Approved
0.6304	Remote Similarity	NPD5306	Approved
0.6299	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7157	Approved
0.6294	Remote Similarity	NPD2861	Phase 2
0.6291	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD1894	Discontinued
0.6269	Remote Similarity	NPD6010	Discontinued
0.6268	Remote Similarity	NPD2797	Approved
0.6268	Remote Similarity	NPD6362	Approved
0.6267	Remote Similarity	NPD6005	Phase 3
0.6267	Remote Similarity	NPD6004	Phase 3
0.6267	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6002	Phase 3
0.6267	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3751	Discontinued
0.626	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.626	Remote Similarity	NPD2684	Approved
0.6259	Remote Similarity	NPD3496	Discontinued
0.6259	Remote Similarity	NPD230	Phase 1
0.6258	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7458	Discontinued
0.6241	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD4571	Approved
0.6241	Remote Similarity	NPD4572	Approved
0.6241	Remote Similarity	NPD4573	Approved
0.6232	Remote Similarity	NPD4105	Approved
0.6232	Remote Similarity	NPD4102	Approved
0.6231	Remote Similarity	NPD3526	Approved
0.6231	Remote Similarity	NPD968	Approved
0.6231	Remote Similarity	NPD3524	Approved
0.6221	Remote Similarity	NPD8434	Phase 2
0.6221	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.622	Remote Similarity	NPD2552	Approved
0.622	Remote Similarity	NPD3787	Discontinued
0.622	Remote Similarity	NPD2555	Approved
0.622	Remote Similarity	NPD2553	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data