NPASS Compound

Structure

NPC470851 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 3 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 0 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 1 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 2 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:	3.081
LogD:	1.467
LogS:	-3.749
# 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:	-5.598
MDCK Permeability:	4.747365164803341e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.709
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	79.50489807128906%
Volume Distribution (VD):	0.464
Pgp-substrate:	19.996204376220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.563
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	3.593
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.731
Drug-inuced Liver Injury (DILI):	0.785
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.188
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC470851

Natural Product ID:	NPC470851
*Common Name:**	Munronin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HEZRGKNYFJXOKF-OEHNLNNJSA-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/h7-9,15-17,19,21-23,31H,1,10-11H2,2-6H3/t15-,16-,17+,19?,21+,22+,23-,26-,27+,28+/m0/s1
SMILES:	CC(=O)OC1C2C(C(=C)C34C1(C(CC3O4)C5=CC(OC5=O)O)C)C(C=CC(=O)O2)(C)C6CC(=O)OC6(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269413
PubChem CID:	11763148
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	5
Others	6

Activity Type	# Activity
Cell Line	5
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	440.0	nM	PMID[490564]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	2300.0	nM	PMID[490564]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1600.0	nM	PMID[490564]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1500.0	nM	PMID[490564]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	860.0	nM	PMID[490564]
NPT785	Organism	Pieris brassicae	Pieris brassicae	mortality	=	20.0	%	PMID[490563]
NPT785	Organism	Pieris brassicae	Pieris brassicae	AFI	=	0.0	%	PMID[490563]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	54.3	%	PMID[490564]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	51.8	%	PMID[490564]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	43.8	%	PMID[490564]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	35.1	%	PMID[490564]

☑ 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 NPC470851 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	278
0.1-0.2	1705
0.2-0.3	4884
0.3-0.4	8608
0.4-0.5	13304
0.5-0.6	7483
0.6-0.7	5191
0.7-0.8	1195
0.8-0.85	34
0.85-0.9	10
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC470850
0.9322	High Similarity	NPC4548
0.9187	High Similarity	NPC175186
0.916	High Similarity	NPC143755
0.9113	High Similarity	NPC471170
0.9076	High Similarity	NPC472667
0.9032	High Similarity	NPC104382
0.8983	High Similarity	NPC470793
0.8629	High Similarity	NPC469382
0.8605	High Similarity	NPC478072
0.8605	High Similarity	NPC471234
0.8594	High Similarity	NPC472769
0.8583	High Similarity	NPC472770
0.856	High Similarity	NPC75856
0.856	High Similarity	NPC86346
0.856	High Similarity	NPC469379
0.8525	High Similarity	NPC159928
0.8468	Intermediate Similarity	NPC310511
0.8433	Intermediate Similarity	NPC5153
0.8433	Intermediate Similarity	NPC48414
0.8409	Intermediate Similarity	NPC246209
0.8387	Intermediate Similarity	NPC151616
0.8361	Intermediate Similarity	NPC138372
0.8361	Intermediate Similarity	NPC106228
0.8359	Intermediate Similarity	NPC473620
0.8333	Intermediate Similarity	NPC472768
0.8309	Intermediate Similarity	NPC471172
0.8306	Intermediate Similarity	NPC19028
0.8306	Intermediate Similarity	NPC469380
0.8306	Intermediate Similarity	NPC9674
0.8295	Intermediate Similarity	NPC231529
0.8295	Intermediate Similarity	NPC475371
0.8281	Intermediate Similarity	NPC42399
0.8281	Intermediate Similarity	NPC287423
0.8248	Intermediate Similarity	NPC48813
0.8248	Intermediate Similarity	NPC194854
0.8244	Intermediate Similarity	NPC88668
0.824	Intermediate Similarity	NPC471128
0.824	Intermediate Similarity	NPC145182
0.824	Intermediate Similarity	NPC471126
0.824	Intermediate Similarity	NPC157252
0.8231	Intermediate Similarity	NPC475389
0.8231	Intermediate Similarity	NPC473838
0.8217	Intermediate Similarity	NPC270109
0.8211	Intermediate Similarity	NPC154363
0.8211	Intermediate Similarity	NPC234858
0.8211	Intermediate Similarity	NPC471127
0.8211	Intermediate Similarity	NPC471816
0.8189	Intermediate Similarity	NPC129992
0.8189	Intermediate Similarity	NPC27363
0.8189	Intermediate Similarity	NPC472399
0.8189	Intermediate Similarity	NPC473979
0.8188	Intermediate Similarity	NPC16729
0.8188	Intermediate Similarity	NPC475462
0.8175	Intermediate Similarity	NPC204731
0.8175	Intermediate Similarity	NPC52839
0.8168	Intermediate Similarity	NPC180902
0.8168	Intermediate Similarity	NPC93416
0.8168	Intermediate Similarity	NPC471855
0.8168	Intermediate Similarity	NPC475139
0.816	Intermediate Similarity	NPC312536
0.816	Intermediate Similarity	NPC236918
0.816	Intermediate Similarity	NPC156745
0.8154	Intermediate Similarity	NPC473593
0.8145	Intermediate Similarity	NPC10721
0.8145	Intermediate Similarity	NPC13713
0.814	Intermediate Similarity	NPC179412
0.814	Intermediate Similarity	NPC146456
0.814	Intermediate Similarity	NPC471356
0.814	Intermediate Similarity	NPC469757
0.814	Intermediate Similarity	NPC117702
0.814	Intermediate Similarity	NPC298841
0.814	Intermediate Similarity	NPC471357
0.813	Intermediate Similarity	NPC90472
0.8125	Intermediate Similarity	NPC473919
0.8125	Intermediate Similarity	NPC473709
0.8125	Intermediate Similarity	NPC145238
0.811	Intermediate Similarity	NPC470419
0.811	Intermediate Similarity	NPC257017
0.811	Intermediate Similarity	NPC222688
0.811	Intermediate Similarity	NPC162009
0.8106	Intermediate Similarity	NPC104585
0.8106	Intermediate Similarity	NPC298783
0.8106	Intermediate Similarity	NPC157817
0.8106	Intermediate Similarity	NPC225385
0.8095	Intermediate Similarity	NPC329080
0.8095	Intermediate Similarity	NPC472004
0.8095	Intermediate Similarity	NPC472759
0.8095	Intermediate Similarity	NPC475885
0.8092	Intermediate Similarity	NPC16569
0.8092	Intermediate Similarity	NPC476852
0.8092	Intermediate Similarity	NPC476862
0.8092	Intermediate Similarity	NPC159338
0.8092	Intermediate Similarity	NPC476863
0.8092	Intermediate Similarity	NPC253456
0.808	Intermediate Similarity	NPC171905
0.808	Intermediate Similarity	NPC124676
0.808	Intermediate Similarity	NPC470420
0.808	Intermediate Similarity	NPC146280
0.808	Intermediate Similarity	NPC472397
0.808	Intermediate Similarity	NPC471125
0.808	Intermediate Similarity	NPC475372
0.808	Intermediate Similarity	NPC472758
0.8077	Intermediate Similarity	NPC476091
0.8077	Intermediate Similarity	NPC476078
0.8077	Intermediate Similarity	NPC311534
0.8074	Intermediate Similarity	NPC476558
0.8062	Intermediate Similarity	NPC293112
0.8062	Intermediate Similarity	NPC222307
0.8062	Intermediate Similarity	NPC250556
0.8062	Intermediate Similarity	NPC469750
0.8049	Intermediate Similarity	NPC472757
0.8047	Intermediate Similarity	NPC469352
0.8047	Intermediate Similarity	NPC473802
0.8045	Intermediate Similarity	NPC471137
0.8045	Intermediate Similarity	NPC473548
0.8045	Intermediate Similarity	NPC223356
0.8045	Intermediate Similarity	NPC471136
0.8045	Intermediate Similarity	NPC475154
0.8045	Intermediate Similarity	NPC475500
0.8045	Intermediate Similarity	NPC100017
0.8045	Intermediate Similarity	NPC182266
0.8031	Intermediate Similarity	NPC472401
0.803	Intermediate Similarity	NPC42670
0.803	Intermediate Similarity	NPC19124
0.8016	Intermediate Similarity	NPC255081
0.8016	Intermediate Similarity	NPC275696
0.8016	Intermediate Similarity	NPC471108
0.8016	Intermediate Similarity	NPC22628
0.8016	Intermediate Similarity	NPC5989
0.8016	Intermediate Similarity	NPC5991
0.8015	Intermediate Similarity	NPC219085
0.8015	Intermediate Similarity	NPC476851
0.8015	Intermediate Similarity	NPC17896
0.8015	Intermediate Similarity	NPC471407
0.8015	Intermediate Similarity	NPC10823
0.8015	Intermediate Similarity	NPC469755
0.8015	Intermediate Similarity	NPC197707
0.8015	Intermediate Similarity	NPC180079
0.8015	Intermediate Similarity	NPC469753
0.8015	Intermediate Similarity	NPC469754
0.8015	Intermediate Similarity	NPC9499
0.8015	Intermediate Similarity	NPC471358
0.8015	Intermediate Similarity	NPC86159
0.8015	Intermediate Similarity	NPC469751
0.8015	Intermediate Similarity	NPC284406
0.8015	Intermediate Similarity	NPC89514
0.8015	Intermediate Similarity	NPC469752
0.8015	Intermediate Similarity	NPC471352
0.8015	Intermediate Similarity	NPC162495
0.8015	Intermediate Similarity	NPC91
0.8015	Intermediate Similarity	NPC471360
0.8015	Intermediate Similarity	NPC6108
0.8015	Intermediate Similarity	NPC471361
0.8015	Intermediate Similarity	NPC251866
0.8015	Intermediate Similarity	NPC70542
0.8015	Intermediate Similarity	NPC471359
0.8	Intermediate Similarity	NPC240070
0.8	Intermediate Similarity	NPC329784
0.8	Intermediate Similarity	NPC471940
0.8	Intermediate Similarity	NPC473656
0.8	Intermediate Similarity	NPC469684
0.7984	Intermediate Similarity	NPC81736
0.7984	Intermediate Similarity	NPC172154
0.7984	Intermediate Similarity	NPC8369
0.7984	Intermediate Similarity	NPC178289
0.7984	Intermediate Similarity	NPC216665
0.7984	Intermediate Similarity	NPC472400
0.7971	Intermediate Similarity	NPC471171
0.797	Intermediate Similarity	NPC477709
0.797	Intermediate Similarity	NPC142756
0.797	Intermediate Similarity	NPC476221
0.7969	Intermediate Similarity	NPC19464
0.7967	Intermediate Similarity	NPC222834
0.7955	Intermediate Similarity	NPC251564
0.7955	Intermediate Similarity	NPC476855
0.7955	Intermediate Similarity	NPC475606
0.7955	Intermediate Similarity	NPC477189
0.7955	Intermediate Similarity	NPC475314
0.7953	Intermediate Similarity	NPC241192
0.7953	Intermediate Similarity	NPC48692
0.7939	Intermediate Similarity	NPC477490
0.7939	Intermediate Similarity	NPC473888
0.7939	Intermediate Similarity	NPC114306
0.7939	Intermediate Similarity	NPC476859
0.7937	Intermediate Similarity	NPC475913
0.7926	Intermediate Similarity	NPC59288
0.7926	Intermediate Similarity	NPC68282
0.7923	Intermediate Similarity	NPC471939
0.7923	Intermediate Similarity	NPC473635
0.7923	Intermediate Similarity	NPC217901
0.792	Intermediate Similarity	NPC266728
0.792	Intermediate Similarity	NPC49492
0.7907	Intermediate Similarity	NPC469789
0.7907	Intermediate Similarity	NPC471392
0.7907	Intermediate Similarity	NPC11895
0.7895	Intermediate Similarity	NPC474508
0.7895	Intermediate Similarity	NPC231240
0.7895	Intermediate Similarity	NPC473485
0.7891	Intermediate Similarity	NPC470418

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 NPC470851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1997
0.2-0.3	3895
0.3-0.4	2047
0.4-0.5	567
0.5-0.6	245
0.6-0.7	133
0.7-0.8	18
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
0.8062	Intermediate Similarity	NPD7507	Approved
0.8015	Intermediate Similarity	NPD7319	Approved
0.7874	Intermediate Similarity	NPD7516	Approved
0.7795	Intermediate Similarity	NPD7327	Approved
0.7795	Intermediate Similarity	NPD7328	Approved
0.7557	Intermediate Similarity	NPD6370	Approved
0.7537	Intermediate Similarity	NPD7736	Approved
0.7481	Intermediate Similarity	NPD8378	Approved
0.7481	Intermediate Similarity	NPD8379	Approved
0.7481	Intermediate Similarity	NPD8335	Approved
0.7481	Intermediate Similarity	NPD8033	Approved
0.7481	Intermediate Similarity	NPD8380	Approved
0.7481	Intermediate Similarity	NPD8296	Approved
0.748	Intermediate Similarity	NPD6008	Approved
0.7463	Intermediate Similarity	NPD7078	Approved
0.7444	Intermediate Similarity	NPD7492	Approved
0.7442	Intermediate Similarity	NPD7115	Discovery
0.7405	Intermediate Similarity	NPD8377	Approved
0.7405	Intermediate Similarity	NPD8294	Approved
0.7405	Intermediate Similarity	NPD6054	Approved
0.7388	Intermediate Similarity	NPD6616	Approved
0.7381	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6686	Approved
0.7333	Intermediate Similarity	NPD8293	Discontinued
0.7302	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD5344	Discontinued
0.728	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6882	Approved
0.7266	Intermediate Similarity	NPD8297	Approved
0.7218	Intermediate Similarity	NPD7503	Approved
0.7218	Intermediate Similarity	NPD6015	Approved
0.7218	Intermediate Similarity	NPD6016	Approved
0.7213	Intermediate Similarity	NPD6648	Approved
0.7188	Intermediate Similarity	NPD6649	Approved
0.7188	Intermediate Similarity	NPD6650	Approved
0.7176	Intermediate Similarity	NPD6009	Approved
0.7164	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7132	Intermediate Similarity	NPD6053	Discontinued
0.7109	Intermediate Similarity	NPD6371	Approved
0.7087	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD6881	Approved
0.7077	Intermediate Similarity	NPD4632	Approved
0.7073	Intermediate Similarity	NPD7639	Approved
0.7073	Intermediate Similarity	NPD7640	Approved
0.7031	Intermediate Similarity	NPD6373	Approved
0.7031	Intermediate Similarity	NPD6372	Approved
0.7008	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5697	Approved
0.6992	Remote Similarity	NPD7638	Approved
0.6985	Remote Similarity	NPD7604	Phase 2
0.6977	Remote Similarity	NPD7102	Approved
0.6977	Remote Similarity	NPD6883	Approved
0.6977	Remote Similarity	NPD7290	Approved
0.6963	Remote Similarity	NPD8515	Approved
0.6963	Remote Similarity	NPD8513	Phase 3
0.6963	Remote Similarity	NPD8516	Approved
0.6963	Remote Similarity	NPD8517	Approved
0.6953	Remote Similarity	NPD7320	Approved
0.6929	Remote Similarity	NPD6402	Approved
0.6929	Remote Similarity	NPD7128	Approved
0.6929	Remote Similarity	NPD5739	Approved
0.6929	Remote Similarity	NPD6675	Approved
0.6923	Remote Similarity	NPD6869	Approved
0.6923	Remote Similarity	NPD6847	Approved
0.6923	Remote Similarity	NPD8130	Phase 1
0.6923	Remote Similarity	NPD6617	Approved
0.6899	Remote Similarity	NPD6013	Approved
0.6899	Remote Similarity	NPD6012	Approved
0.6899	Remote Similarity	NPD6014	Approved
0.6875	Remote Similarity	NPD6412	Phase 2
0.6855	Remote Similarity	NPD4225	Approved
0.6838	Remote Similarity	NPD5983	Phase 2
0.6825	Remote Similarity	NPD5211	Phase 2
0.6822	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8133	Approved
0.6763	Remote Similarity	NPD6336	Discontinued
0.675	Remote Similarity	NPD1695	Approved
0.6746	Remote Similarity	NPD1700	Approved
0.6744	Remote Similarity	NPD5701	Approved
0.6719	Remote Similarity	NPD5141	Approved
0.6694	Remote Similarity	NPD46	Approved
0.6694	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6619	Remote Similarity	NPD6067	Discontinued
0.6619	Remote Similarity	NPD8328	Phase 3
0.6613	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4634	Approved
0.6569	Remote Similarity	NPD7101	Approved
0.6569	Remote Similarity	NPD7100	Approved
0.6562	Remote Similarity	NPD7632	Discontinued
0.6562	Remote Similarity	NPD5224	Approved
0.6562	Remote Similarity	NPD4633	Approved
0.6562	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD5226	Approved
0.6557	Remote Similarity	NPD5785	Approved
0.6541	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5175	Approved
0.6512	Remote Similarity	NPD5174	Approved
0.6508	Remote Similarity	NPD4755	Approved
0.6496	Remote Similarity	NPD6335	Approved
0.6484	Remote Similarity	NPD5223	Approved
0.6479	Remote Similarity	NPD8074	Phase 3
0.6471	Remote Similarity	NPD6274	Approved
0.6457	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4729	Approved
0.6439	Remote Similarity	NPD4730	Approved
0.6423	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7838	Discovery
0.6423	Remote Similarity	NPD6317	Approved
0.6418	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7260	Phase 2
0.6406	Remote Similarity	NPD4700	Approved
0.6378	Remote Similarity	NPD6083	Phase 2
0.6378	Remote Similarity	NPD6084	Phase 2
0.6377	Remote Similarity	NPD6314	Approved
0.6377	Remote Similarity	NPD6313	Approved
0.6371	Remote Similarity	NPD6079	Approved
0.637	Remote Similarity	NPD8338	Approved
0.6369	Remote Similarity	NPD7799	Discontinued
0.6364	Remote Similarity	NPD7625	Phase 1
0.6357	Remote Similarity	NPD6921	Approved
0.6343	Remote Similarity	NPD5249	Phase 3
0.6343	Remote Similarity	NPD5248	Approved
0.6343	Remote Similarity	NPD5247	Approved
0.6343	Remote Similarity	NPD5251	Approved
0.6343	Remote Similarity	NPD5250	Approved
0.632	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD4251	Approved
0.6311	Remote Similarity	NPD4250	Approved
0.6288	Remote Similarity	NPD4768	Approved
0.6288	Remote Similarity	NPD4767	Approved
0.6281	Remote Similarity	NPD1694	Approved
0.627	Remote Similarity	NPD6001	Approved
0.6268	Remote Similarity	NPD7642	Approved
0.6259	Remote Similarity	NPD6845	Suspended
0.625	Remote Similarity	NPD5362	Discontinued
0.6241	Remote Similarity	NPD6908	Approved
0.6241	Remote Similarity	NPD6909	Approved
0.624	Remote Similarity	NPD7983	Approved
0.624	Remote Similarity	NPD7637	Suspended
0.6233	Remote Similarity	NPD5956	Approved
0.623	Remote Similarity	NPD4249	Approved
0.622	Remote Similarity	NPD5695	Phase 3
0.6212	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5328	Approved
0.6202	Remote Similarity	NPD5696	Approved
0.6194	Remote Similarity	NPD5128	Approved
0.619	Remote Similarity	NPD4202	Approved
0.619	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD5778	Approved
0.6176	Remote Similarity	NPD5215	Approved
0.6176	Remote Similarity	NPD5216	Approved
0.6176	Remote Similarity	NPD5217	Approved
0.6172	Remote Similarity	NPD5221	Approved
0.6172	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5222	Approved
0.6167	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.616	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD7830	Approved
0.6154	Remote Similarity	NPD7829	Approved
0.6148	Remote Similarity	NPD5363	Approved
0.6136	Remote Similarity	NPD4754	Approved
0.6129	Remote Similarity	NPD6903	Approved
0.6124	Remote Similarity	NPD5173	Approved
0.6115	Remote Similarity	NPD6868	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6111	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD5693	Phase 1
0.6103	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD5135	Approved
0.6103	Remote Similarity	NPD5169	Approved
0.6098	Remote Similarity	NPD7334	Approved
0.6098	Remote Similarity	NPD5786	Approved
0.6098	Remote Similarity	NPD7521	Approved
0.6098	Remote Similarity	NPD6409	Approved
0.6098	Remote Similarity	NPD5330	Approved
0.6098	Remote Similarity	NPD7146	Approved
0.6098	Remote Similarity	NPD6684	Approved
0.6094	Remote Similarity	NPD4629	Approved
0.6094	Remote Similarity	NPD5210	Approved
0.6066	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5127	Approved
0.6053	Remote Similarity	NPD6333	Approved
0.6053	Remote Similarity	NPD6334	Approved
0.6048	Remote Similarity	NPD7524	Approved
0.6047	Remote Similarity	NPD4697	Phase 3
0.6033	Remote Similarity	NPD6435	Approved
0.6032	Remote Similarity	NPD3168	Discontinued
0.6016	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5282	Discontinued

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