NPASS Compound

Structure

NPC470850 OpenBabel07101718222D 38 43 0 0 1 0 0 0 0 0999 V2000 -0.8282 -0.8601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4408 -3.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3260 -4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3704 -4.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9908 -1.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5602 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -4.3852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5934 -3.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9927 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0793 -1.8655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1840 -3.0743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5037 -2.6832 0.0000 C 0 0 1 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 1.1203 -4.2510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9437 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0349 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3308 -2.1473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2818 -2.4563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0250 -1.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9927 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1035 -3.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5038 -2.6982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -0.8090 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 4.1350 -3.3833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6712 -5.0856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7527 -1.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8350 -1.5604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6836 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9761 -2.0962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6332 -3.3925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9437 0.5000 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 -3.0498 -3.1601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 26 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 29 2 0 0 0 0 13 34 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 27 1 1 0 0 0 16 11 1 6 0 0 0 16 25 1 0 0 0 0 16 26 1 0 0 0 0 17 28 1 1 0 0 0 17 37 1 0 0 0 0 18 30 2 0 0 0 0 18 35 1 0 0 0 0 19 31 2 0 0 0 0 19 36 1 0 0 0 0 20 32 2 0 0 0 0 20 38 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 6 0 0 0 22 23 1 0 0 0 0 22 35 1 6 0 0 0 23 27 1 1 0 0 0 23 34 1 0 0 0 0 24 33 1 0 0 0 0 24 36 1 0 0 0 0 25 38 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 12 1 1 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.2
Volume:	510.952
LogP:	2.93
LogD:	1.465
LogS:	-3.957
# Rotatable Bonds:	4
TPSA:	145.03
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	6.084
Fsp3:	0.607
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.571
MDCK Permeability:	4.8077406972879544e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.778
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	78.630859375%
Volume Distribution (VD):	0.444
Pgp-substrate:	22.39041519165039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.501
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.48
CYP3A4-substrate:	0.35

ADMET: Excretion

Clearance (CL):	4.055
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.796
Drug-inuced Liver Injury (DILI):	0.683
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.863
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.122
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC470850

Natural Product ID:	NPC470850
*Common Name:**	Munronin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QBKSPXLEBYOGMB-CLHFBQQZSA-N
Standard InCHI:	InChI=1S/C28H32O10/c1-12-21-22(35-18(30)7-8-26(21,5)16-11-20(32)38-25(16,3)4)23(34-13(2)29)27(6)15(10-17-28(12,27)37-17)14-9-19(31)36-24(14)33/h7-9,15-17,21-24,33H,1,10-11H2,2-6H3/t15-,16-,17+,21+,22+,23-,24?,26-,27+,28+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H]2OC(=O)C=C[C@@]([C@@H]2C(=C)[C@@]23[C@]1(C)[C@@H](C[C@H]3O2)C1=CC(=O)OC1O)(C)[C@H]1CC(=O)OC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269412
PubChem CID:	11135190
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	whole plants	Wenshan, Yunnan Province, China	2012-Nov	PMID[25798528]
NPO9173	Munronia henryi	Species	Meliaceae	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	6
Others	12

Activity Type	# Activity
Cell Line	5
Organism	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[535657]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[535657]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[535657]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[535657]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[535657]
NPT785	Organism	Pieris brassicae	Pieris brassicae	mortality	=	10.0	%	PMID[535656]
NPT785	Organism	Pieris brassicae	Pieris brassicae	AFI	=	20.9	%	PMID[535656]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	91.8	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	87.3	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	57.2	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	43.9	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	85.7	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	52.7	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	43.1	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	39.8	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	13.5	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	5.4	%	PMID[535657]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	IC50	=	33.9	ug.mL-1	PMID[535657]

☑ 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 NPC470850 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	272
0.1-0.2	1588
0.2-0.3	4610
0.3-0.4	8736
0.4-0.5	13206
0.5-0.6	7330
0.6-0.7	5548
0.7-0.8	1352
0.8-0.85	43
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC470851
0.9106	High Similarity	NPC104382
0.9076	High Similarity	NPC4548
0.9076	High Similarity	NPC143755
0.906	High Similarity	NPC470793
0.8992	High Similarity	NPC472667
0.8952	High Similarity	NPC175186
0.888	High Similarity	NPC471170
0.8615	High Similarity	NPC246209
0.8595	High Similarity	NPC159928
0.8548	High Similarity	NPC469382
0.8527	High Similarity	NPC471234
0.8504	High Similarity	NPC475371
0.848	Intermediate Similarity	NPC86346
0.848	Intermediate Similarity	NPC469379
0.848	Intermediate Similarity	NPC75856
0.84	Intermediate Similarity	NPC129992
0.8387	Intermediate Similarity	NPC310511
0.8385	Intermediate Similarity	NPC478072
0.8374	Intermediate Similarity	NPC312536
0.8372	Intermediate Similarity	NPC472769
0.8359	Intermediate Similarity	NPC473593
0.8359	Intermediate Similarity	NPC472770
0.8358	Intermediate Similarity	NPC5153
0.8358	Intermediate Similarity	NPC48414
0.8306	Intermediate Similarity	NPC157252
0.8306	Intermediate Similarity	NPC471128
0.8306	Intermediate Similarity	NPC471126
0.8306	Intermediate Similarity	NPC145182
0.8293	Intermediate Similarity	NPC475372
0.8281	Intermediate Similarity	NPC270109
0.8281	Intermediate Similarity	NPC473620
0.8279	Intermediate Similarity	NPC154363
0.8279	Intermediate Similarity	NPC106228
0.8279	Intermediate Similarity	NPC234858
0.8279	Intermediate Similarity	NPC471127
0.8279	Intermediate Similarity	NPC138372
0.8254	Intermediate Similarity	NPC469352
0.824	Intermediate Similarity	NPC52839
0.8235	Intermediate Similarity	NPC471172
0.8226	Intermediate Similarity	NPC9674
0.8226	Intermediate Similarity	NPC156745
0.8226	Intermediate Similarity	NPC19028
0.8226	Intermediate Similarity	NPC236918
0.8226	Intermediate Similarity	NPC469380
0.8217	Intermediate Similarity	NPC471407
0.8217	Intermediate Similarity	NPC231529
0.8211	Intermediate Similarity	NPC473656
0.8211	Intermediate Similarity	NPC10721
0.8203	Intermediate Similarity	NPC42399
0.8203	Intermediate Similarity	NPC287423
0.8197	Intermediate Similarity	NPC216665
0.8189	Intermediate Similarity	NPC145238
0.8175	Intermediate Similarity	NPC48813
0.8175	Intermediate Similarity	NPC162009
0.8175	Intermediate Similarity	NPC194854
0.8175	Intermediate Similarity	NPC257017
0.8168	Intermediate Similarity	NPC88668
0.816	Intermediate Similarity	NPC472759
0.816	Intermediate Similarity	NPC329080
0.816	Intermediate Similarity	NPC151616
0.816	Intermediate Similarity	NPC475885
0.8154	Intermediate Similarity	NPC473838
0.8154	Intermediate Similarity	NPC475389
0.8145	Intermediate Similarity	NPC471125
0.8145	Intermediate Similarity	NPC124676
0.8145	Intermediate Similarity	NPC146280
0.8145	Intermediate Similarity	NPC472397
0.8145	Intermediate Similarity	NPC171905
0.8145	Intermediate Similarity	NPC472758
0.8145	Intermediate Similarity	NPC475913
0.8134	Intermediate Similarity	NPC476558
0.813	Intermediate Similarity	NPC471816
0.8125	Intermediate Similarity	NPC222307
0.8116	Intermediate Similarity	NPC475462
0.8116	Intermediate Similarity	NPC16729
0.8115	Intermediate Similarity	NPC472757
0.811	Intermediate Similarity	NPC473979
0.811	Intermediate Similarity	NPC472399
0.811	Intermediate Similarity	NPC472768
0.811	Intermediate Similarity	NPC27363
0.8095	Intermediate Similarity	NPC470418
0.8092	Intermediate Similarity	NPC93416
0.8092	Intermediate Similarity	NPC475139
0.8092	Intermediate Similarity	NPC231240
0.8092	Intermediate Similarity	NPC180902
0.8092	Intermediate Similarity	NPC471855
0.808	Intermediate Similarity	NPC255081
0.808	Intermediate Similarity	NPC474179
0.808	Intermediate Similarity	NPC275696
0.808	Intermediate Similarity	NPC5991
0.808	Intermediate Similarity	NPC475834
0.808	Intermediate Similarity	NPC471108
0.808	Intermediate Similarity	NPC22628
0.808	Intermediate Similarity	NPC5989
0.8065	Intermediate Similarity	NPC13713
0.8065	Intermediate Similarity	NPC475323
0.8062	Intermediate Similarity	NPC469757
0.8062	Intermediate Similarity	NPC298841
0.8062	Intermediate Similarity	NPC471357
0.8062	Intermediate Similarity	NPC117702
0.8062	Intermediate Similarity	NPC471356
0.8062	Intermediate Similarity	NPC179412
0.8062	Intermediate Similarity	NPC146456
0.8049	Intermediate Similarity	NPC43213
0.8049	Intermediate Similarity	NPC472400
0.8047	Intermediate Similarity	NPC473709
0.8047	Intermediate Similarity	NPC473919
0.8031	Intermediate Similarity	NPC470265
0.8031	Intermediate Similarity	NPC23786
0.8031	Intermediate Similarity	NPC471082
0.8031	Intermediate Similarity	NPC222688
0.803	Intermediate Similarity	NPC298783
0.803	Intermediate Similarity	NPC225385
0.803	Intermediate Similarity	NPC104585
0.803	Intermediate Similarity	NPC157817
0.803	Intermediate Similarity	NPC316915
0.8016	Intermediate Similarity	NPC470312
0.8016	Intermediate Similarity	NPC472004
0.8015	Intermediate Similarity	NPC16569
0.8015	Intermediate Similarity	NPC159338
0.8015	Intermediate Similarity	NPC476852
0.8015	Intermediate Similarity	NPC476862
0.8015	Intermediate Similarity	NPC476863
0.8015	Intermediate Similarity	NPC253456
0.8	Intermediate Similarity	NPC83287
0.8	Intermediate Similarity	NPC476091
0.8	Intermediate Similarity	NPC38948
0.8	Intermediate Similarity	NPC181994
0.8	Intermediate Similarity	NPC476078
0.8	Intermediate Similarity	NPC311534
0.7984	Intermediate Similarity	NPC293112
0.7984	Intermediate Similarity	NPC250556
0.7984	Intermediate Similarity	NPC469750
0.7983	Intermediate Similarity	NPC470980
0.797	Intermediate Similarity	NPC471136
0.797	Intermediate Similarity	NPC100017
0.797	Intermediate Similarity	NPC182266
0.797	Intermediate Similarity	NPC475500
0.797	Intermediate Similarity	NPC471137
0.797	Intermediate Similarity	NPC475154
0.797	Intermediate Similarity	NPC473548
0.797	Intermediate Similarity	NPC223356
0.797	Intermediate Similarity	NPC476823
0.7969	Intermediate Similarity	NPC473802
0.7969	Intermediate Similarity	NPC41129
0.7955	Intermediate Similarity	NPC42670
0.7955	Intermediate Similarity	NPC19124
0.7953	Intermediate Similarity	NPC472401
0.7953	Intermediate Similarity	NPC470878
0.7953	Intermediate Similarity	NPC473256
0.7953	Intermediate Similarity	NPC67569
0.7953	Intermediate Similarity	NPC204731
0.7939	Intermediate Similarity	NPC469755
0.7939	Intermediate Similarity	NPC471359
0.7939	Intermediate Similarity	NPC471361
0.7939	Intermediate Similarity	NPC469754
0.7939	Intermediate Similarity	NPC469751
0.7939	Intermediate Similarity	NPC284406
0.7939	Intermediate Similarity	NPC180079
0.7939	Intermediate Similarity	NPC162495
0.7939	Intermediate Similarity	NPC219085
0.7939	Intermediate Similarity	NPC476966
0.7939	Intermediate Similarity	NPC89514
0.7939	Intermediate Similarity	NPC17896
0.7939	Intermediate Similarity	NPC476851
0.7939	Intermediate Similarity	NPC10823
0.7939	Intermediate Similarity	NPC9499
0.7939	Intermediate Similarity	NPC469753
0.7939	Intermediate Similarity	NPC86159
0.7939	Intermediate Similarity	NPC471352
0.7939	Intermediate Similarity	NPC197707
0.7939	Intermediate Similarity	NPC251866
0.7939	Intermediate Similarity	NPC6108
0.7939	Intermediate Similarity	NPC469752
0.7939	Intermediate Similarity	NPC471360
0.7939	Intermediate Similarity	NPC70542
0.7939	Intermediate Similarity	NPC91
0.7939	Intermediate Similarity	NPC471358
0.7937	Intermediate Similarity	NPC477071
0.7934	Intermediate Similarity	NPC206618
0.7923	Intermediate Similarity	NPC240070
0.7923	Intermediate Similarity	NPC329784
0.7923	Intermediate Similarity	NPC471940
0.792	Intermediate Similarity	NPC34390
0.792	Intermediate Similarity	NPC474418
0.792	Intermediate Similarity	NPC77319
0.792	Intermediate Similarity	NPC87250
0.792	Intermediate Similarity	NPC142066
0.792	Intermediate Similarity	NPC471351
0.792	Intermediate Similarity	NPC290693
0.792	Intermediate Similarity	NPC309034
0.792	Intermediate Similarity	NPC157376
0.792	Intermediate Similarity	NPC244402
0.792	Intermediate Similarity	NPC50305
0.792	Intermediate Similarity	NPC196429
0.792	Intermediate Similarity	NPC99728
0.792	Intermediate Similarity	NPC471354
0.792	Intermediate Similarity	NPC84987
0.792	Intermediate Similarity	NPC152615

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 NPC470850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	1897
0.2-0.3	3825
0.3-0.4	2188
0.4-0.5	581
0.5-0.6	268
0.6-0.7	124
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.808	Intermediate Similarity	NPD7516	Approved
0.8	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD7328	Approved
0.7984	Intermediate Similarity	NPD7507	Approved
0.7939	Intermediate Similarity	NPD7319	Approved
0.7674	Intermediate Similarity	NPD8296	Approved
0.7674	Intermediate Similarity	NPD8380	Approved
0.7674	Intermediate Similarity	NPD8335	Approved
0.7674	Intermediate Similarity	NPD8379	Approved
0.7674	Intermediate Similarity	NPD8033	Approved
0.7674	Intermediate Similarity	NPD8378	Approved
0.7638	Intermediate Similarity	NPD7115	Discovery
0.7597	Intermediate Similarity	NPD8294	Approved
0.7597	Intermediate Similarity	NPD8377	Approved
0.7581	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5344	Discontinued
0.7481	Intermediate Similarity	NPD6370	Approved
0.7463	Intermediate Similarity	NPD7736	Approved
0.7405	Intermediate Similarity	NPD7503	Approved
0.7388	Intermediate Similarity	NPD7078	Approved
0.7368	Intermediate Similarity	NPD7492	Approved
0.7339	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6054	Approved
0.7313	Intermediate Similarity	NPD6616	Approved
0.7302	Intermediate Similarity	NPD6371	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7273	Intermediate Similarity	NPD6648	Approved
0.7273	Intermediate Similarity	NPD7640	Approved
0.7259	Intermediate Similarity	NPD8293	Discontinued
0.7258	Intermediate Similarity	NPD6008	Approved
0.72	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7638	Approved
0.7188	Intermediate Similarity	NPD6882	Approved
0.7188	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD6015	Approved
0.7109	Intermediate Similarity	NPD6649	Approved
0.7109	Intermediate Similarity	NPD6650	Approved
0.7099	Intermediate Similarity	NPD6009	Approved
0.709	Intermediate Similarity	NPD5988	Approved
0.7068	Intermediate Similarity	NPD6319	Approved
0.7068	Intermediate Similarity	NPD6059	Approved
0.7063	Intermediate Similarity	NPD6412	Phase 2
0.7054	Intermediate Similarity	NPD6053	Discontinued
0.7049	Intermediate Similarity	NPD4225	Approved
0.7008	Intermediate Similarity	NPD6881	Approved
0.7008	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.6953	Remote Similarity	NPD6373	Approved
0.6953	Remote Similarity	NPD6372	Approved
0.6929	Remote Similarity	NPD5697	Approved
0.6912	Remote Similarity	NPD7604	Phase 2
0.6899	Remote Similarity	NPD6883	Approved
0.6899	Remote Similarity	NPD7102	Approved
0.6899	Remote Similarity	NPD7290	Approved
0.6891	Remote Similarity	NPD46	Approved
0.6891	Remote Similarity	NPD6698	Approved
0.6889	Remote Similarity	NPD8516	Approved
0.6889	Remote Similarity	NPD8513	Phase 3
0.6889	Remote Similarity	NPD8515	Approved
0.6889	Remote Similarity	NPD8517	Approved
0.6875	Remote Similarity	NPD7320	Approved
0.685	Remote Similarity	NPD7128	Approved
0.685	Remote Similarity	NPD6402	Approved
0.685	Remote Similarity	NPD6675	Approved
0.685	Remote Similarity	NPD5739	Approved
0.6846	Remote Similarity	NPD6847	Approved
0.6846	Remote Similarity	NPD6617	Approved
0.6846	Remote Similarity	NPD6869	Approved
0.6846	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6807	Remote Similarity	NPD1695	Approved
0.6788	Remote Similarity	NPD6067	Discontinued
0.6765	Remote Similarity	NPD5983	Phase 2
0.675	Remote Similarity	NPD5785	Approved
0.6746	Remote Similarity	NPD7632	Discontinued
0.6746	Remote Similarity	NPD5211	Phase 2
0.6744	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6011	Approved
0.6692	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5141	Approved
0.664	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7838	Discovery
0.6596	Remote Similarity	NPD6033	Approved
0.6591	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5285	Approved
0.6587	Remote Similarity	NPD4696	Approved
0.6587	Remote Similarity	NPD5286	Approved
0.656	Remote Similarity	NPD6083	Phase 2
0.656	Remote Similarity	NPD6084	Phase 2
0.6547	Remote Similarity	NPD8328	Phase 3
0.6532	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4634	Approved
0.6513	Remote Similarity	NPD7625	Phase 1
0.6504	Remote Similarity	NPD6399	Phase 3
0.65	Remote Similarity	NPD4251	Approved
0.65	Remote Similarity	NPD4250	Approved
0.6496	Remote Similarity	NPD7101	Approved
0.6496	Remote Similarity	NPD7100	Approved
0.6484	Remote Similarity	NPD5224	Approved
0.6484	Remote Similarity	NPD4633	Approved
0.6484	Remote Similarity	NPD5225	Approved
0.6484	Remote Similarity	NPD5226	Approved
0.6466	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5362	Discontinued
0.6434	Remote Similarity	NPD5175	Approved
0.6434	Remote Similarity	NPD5174	Approved
0.6429	Remote Similarity	NPD4755	Approved
0.6423	Remote Similarity	NPD7637	Suspended
0.6423	Remote Similarity	NPD6335	Approved
0.6417	Remote Similarity	NPD4249	Approved
0.6408	Remote Similarity	NPD8074	Phase 3
0.6406	Remote Similarity	NPD5223	Approved
0.64	Remote Similarity	NPD5695	Phase 3
0.6397	Remote Similarity	NPD6274	Approved
0.6389	Remote Similarity	NPD5956	Approved
0.6378	Remote Similarity	NPD5696	Approved
0.6371	Remote Similarity	NPD4202	Approved
0.6364	Remote Similarity	NPD4730	Approved
0.6364	Remote Similarity	NPD4729	Approved
0.635	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6317	Approved
0.6345	Remote Similarity	NPD7260	Phase 2
0.6333	Remote Similarity	NPD1694	Approved
0.6333	Remote Similarity	NPD5363	Approved
0.6328	Remote Similarity	NPD4700	Approved
0.632	Remote Similarity	NPD6001	Approved
0.631	Remote Similarity	NPD7799	Discontinued
0.6304	Remote Similarity	NPD6313	Approved
0.6304	Remote Similarity	NPD6314	Approved
0.6301	Remote Similarity	NPD8338	Approved
0.629	Remote Similarity	NPD5281	Approved
0.629	Remote Similarity	NPD6079	Approved
0.629	Remote Similarity	NPD5284	Approved
0.6286	Remote Similarity	NPD6921	Approved
0.627	Remote Similarity	NPD5210	Approved
0.627	Remote Similarity	NPD4629	Approved
0.6269	Remote Similarity	NPD5247	Approved
0.6269	Remote Similarity	NPD5251	Approved
0.6269	Remote Similarity	NPD5248	Approved
0.6269	Remote Similarity	NPD5249	Phase 3
0.6269	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7524	Approved
0.6218	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD4768	Approved
0.6212	Remote Similarity	NPD4767	Approved
0.621	Remote Similarity	NPD5207	Approved
0.6198	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD7642	Approved
0.619	Remote Similarity	NPD5282	Discontinued
0.619	Remote Similarity	NPD6845	Suspended
0.6186	Remote Similarity	NPD4822	Approved
0.6186	Remote Similarity	NPD4819	Approved
0.6186	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4821	Approved
0.6186	Remote Similarity	NPD4820	Approved
0.6179	Remote Similarity	NPD6903	Approved
0.6172	Remote Similarity	NPD7902	Approved
0.617	Remote Similarity	NPD6908	Approved
0.617	Remote Similarity	NPD6909	Approved
0.616	Remote Similarity	NPD5693	Phase 1
0.616	Remote Similarity	NPD7983	Approved
0.616	Remote Similarity	NPD8034	Phase 2
0.616	Remote Similarity	NPD8035	Phase 2
0.6148	Remote Similarity	NPD7146	Approved
0.6148	Remote Similarity	NPD3618	Phase 1
0.6148	Remote Similarity	NPD5330	Approved
0.6148	Remote Similarity	NPD6409	Approved
0.6148	Remote Similarity	NPD7334	Approved
0.6148	Remote Similarity	NPD6684	Approved
0.6148	Remote Similarity	NPD7521	Approved
0.6136	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4790	Discontinued
0.6129	Remote Similarity	NPD4753	Phase 2
0.6129	Remote Similarity	NPD5328	Approved
0.6119	Remote Similarity	NPD5128	Approved
0.6116	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5778	Approved
0.6111	Remote Similarity	NPD5779	Approved
0.6103	Remote Similarity	NPD5215	Approved
0.6103	Remote Similarity	NPD5217	Approved
0.6103	Remote Similarity	NPD5216	Approved
0.6094	Remote Similarity	NPD5222	Approved
0.6094	Remote Similarity	NPD5221	Approved
0.6094	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD7829	Approved
0.6084	Remote Similarity	NPD7830	Approved
0.6083	Remote Similarity	NPD4270	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