NPASS Compound

Structure

NPC63061 OpenBabel07101719252D 37 41 0 0 1 0 0 0 0 0999 V2000 0.9999 4.2164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9524 -0.6871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6090 4.2164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9804 -0.6233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1370 -0.4137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9678 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5569 -1.8752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2956 2.7300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1759 1.5828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7849 1.5828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3020 -2.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0812 -0.6114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6512 3.3745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2120 -1.2185 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2602 3.3745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2956 1.8187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9046 1.8187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0208 0.7025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4118 0.7025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6512 1.1742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2602 1.1742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9046 2.7300 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3764 0.0581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7673 0.0581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4961 0.2939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8870 0.2939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4441 1.0364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8904 0.2836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1324 -2.5009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3092 0.7497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9011 0.4666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6123 -0.8223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7928 -0.9949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2238 0.2887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1811 -0.7540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4495 1.9708 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 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 16 2 0 0 0 0 9 19 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 29 1 0 0 0 0 12 34 1 0 0 0 0 12 35 1 0 0 0 0 13 1 1 1 0 0 0 13 15 1 0 0 0 0 14 2 1 1 0 0 0 14 28 1 0 0 0 0 15 3 1 1 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 19 24 2 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 25 2 0 0 0 0 22 17 1 1 0 0 0 22 36 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 0 0 0 0 25 33 1 0 0 0 0 26 37 1 0 0 0 0 27 28 1 0 0 0 0 27 30 2 0 0 0 0 27 36 1 0 0 0 0 28 4 1 1 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.22
Volume:	510.719
LogP:	4.047
LogD:	3.597
LogS:	-5.675
# Rotatable Bonds:	5
TPSA:	101.91
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	5.737
Fsp3:	0.536
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:	-4.863
MDCK Permeability:	2.3792603315087035e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	79.2312240600586%
Volume Distribution (VD):	0.951
Pgp-substrate:	8.893600463867188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.552
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.489
CYP2C9-substrate:	0.785
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.543
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	4.968
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.744
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.148
Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.063
Carcinogencity:	0.548
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC63061

Natural Product ID:	NPC63061
*Common Name:**	Arisanschinin M
IUPAC Name:	n.a.
Synonyms:	Arisanschinin M
Standard InCHIKey:	GHEBHJULQBRZNT-RKZUNUFISA-N
Standard InCHI:	InChI=1S/C28H34O9/c1-13-8-16-9-19-24(35-12-34-19)26-20(16)21-17(10-18(31-5)23(32-6)25(21)33-7)22(15(13)3)36-27(30)28(4,37-26)14(2)11-29/h9-10,13-15,22,29H,8,11-12H2,1-7H3/t13-,14+,15-,22+,28+/m0/s1
SMILES:	COc1c(OC)cc2c(c1OC)c1c3C[C@@H]([C@@H]([C@H]2OC(=O)[C@@](Oc1c1c(c3)OCO1)(C)[C@@H](CO)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2313593
PubChem CID:	71521607
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	4.87	%	PMID[502187]

☑ 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 NPC63061 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	347
0.1-0.2	1469
0.2-0.3	3666
0.3-0.4	8868
0.4-0.5	10102
0.5-0.6	4414
0.6-0.7	7954
0.7-0.8	5460
0.8-0.85	329
0.85-0.9	77
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9671	High Similarity	NPC29727
0.9412	High Similarity	NPC473425
0.9167	High Similarity	NPC473323
0.9145	High Similarity	NPC325720
0.9145	High Similarity	NPC316676
0.9139	High Similarity	NPC321696
0.9139	High Similarity	NPC321958
0.9097	High Similarity	NPC126405
0.9097	High Similarity	NPC16791
0.9097	High Similarity	NPC24562
0.9097	High Similarity	NPC53669
0.9097	High Similarity	NPC308739
0.9097	High Similarity	NPC297271
0.9097	High Similarity	NPC474606
0.9097	High Similarity	NPC77237
0.9097	High Similarity	NPC217708
0.9091	High Similarity	NPC224472
0.9073	High Similarity	NPC318286
0.9073	High Similarity	NPC327651
0.9032	High Similarity	NPC471154
0.9026	High Similarity	NPC473989
0.902	High Similarity	NPC477879
0.9007	High Similarity	NPC326144
0.8981	High Similarity	NPC238834
0.8968	High Similarity	NPC475756
0.894	High Similarity	NPC218510
0.894	High Similarity	NPC76415
0.8917	High Similarity	NPC312763
0.8917	High Similarity	NPC198461
0.8903	High Similarity	NPC316989
0.8896	High Similarity	NPC252281
0.8896	High Similarity	NPC477375
0.8896	High Similarity	NPC198129
0.8896	High Similarity	NPC327352
0.8868	High Similarity	NPC475592
0.8861	High Similarity	NPC476065
0.8846	High Similarity	NPC303519
0.8839	High Similarity	NPC477376
0.8839	High Similarity	NPC477374
0.8839	High Similarity	NPC322426
0.8816	High Similarity	NPC324962
0.8782	High Similarity	NPC477381
0.875	High Similarity	NPC229172
0.875	High Similarity	NPC36531
0.875	High Similarity	NPC230538
0.875	High Similarity	NPC103637
0.8726	High Similarity	NPC477379
0.8718	High Similarity	NPC85141
0.871	High Similarity	NPC295297
0.871	High Similarity	NPC137352
0.871	High Similarity	NPC183083
0.8701	High Similarity	NPC475868
0.8696	High Similarity	NPC241600
0.8696	High Similarity	NPC173726
0.8679	High Similarity	NPC178195
0.8679	High Similarity	NPC348849
0.8675	High Similarity	NPC290714
0.8675	High Similarity	NPC201404
0.8675	High Similarity	NPC53722
0.8671	High Similarity	NPC302610
0.8659	High Similarity	NPC222531
0.8654	High Similarity	NPC304821
0.8645	High Similarity	NPC474054
0.8642	High Similarity	NPC119910
0.8636	High Similarity	NPC239254
0.8636	High Similarity	NPC172171
0.8634	High Similarity	NPC19947
0.8634	High Similarity	NPC207584
0.8627	High Similarity	NPC287124
0.8625	High Similarity	NPC117154
0.8616	High Similarity	NPC245948
0.8616	High Similarity	NPC149735
0.8616	High Similarity	NPC477377
0.8609	High Similarity	NPC865
0.8606	High Similarity	NPC320471
0.8606	High Similarity	NPC83049
0.8606	High Similarity	NPC118162
0.8581	High Similarity	NPC197352
0.8581	High Similarity	NPC189239
0.8581	High Similarity	NPC110763
0.8581	High Similarity	NPC166506
0.858	High Similarity	NPC230531
0.858	High Similarity	NPC215400
0.8571	High Similarity	NPC32373
0.8571	High Similarity	NPC237946
0.8571	High Similarity	NPC477380
0.8553	High Similarity	NPC477378
0.8553	High Similarity	NPC475229
0.8544	High Similarity	NPC470916
0.8528	High Similarity	NPC96593
0.8519	High Similarity	NPC477885
0.8516	High Similarity	NPC87883
0.8516	High Similarity	NPC477701
0.8516	High Similarity	NPC73467
0.8516	High Similarity	NPC166884
0.8516	High Similarity	NPC141569
0.8516	High Similarity	NPC121661
0.85	High Similarity	NPC474514
0.8481	Intermediate Similarity	NPC474347
0.8481	Intermediate Similarity	NPC474393
0.8481	Intermediate Similarity	NPC477698
0.8476	Intermediate Similarity	NPC152424
0.8476	Intermediate Similarity	NPC100465
0.8476	Intermediate Similarity	NPC288149
0.8476	Intermediate Similarity	NPC115624
0.8466	Intermediate Similarity	NPC325122
0.8457	Intermediate Similarity	NPC163635
0.8452	Intermediate Similarity	NPC477883
0.8443	Intermediate Similarity	NPC79322
0.8443	Intermediate Similarity	NPC471180
0.8438	Intermediate Similarity	NPC56184
0.8434	Intermediate Similarity	NPC474647
0.8428	Intermediate Similarity	NPC229882
0.8428	Intermediate Similarity	NPC24425
0.8428	Intermediate Similarity	NPC158635
0.8421	Intermediate Similarity	NPC143895
0.8418	Intermediate Similarity	NPC270751
0.8415	Intermediate Similarity	NPC91634
0.8415	Intermediate Similarity	NPC268718
0.8415	Intermediate Similarity	NPC150943
0.8411	Intermediate Similarity	NPC256776
0.8411	Intermediate Similarity	NPC185680
0.8411	Intermediate Similarity	NPC145722
0.8408	Intermediate Similarity	NPC154971
0.8408	Intermediate Similarity	NPC252286
0.8408	Intermediate Similarity	NPC212890
0.8397	Intermediate Similarity	NPC143092
0.8397	Intermediate Similarity	NPC18211
0.8395	Intermediate Similarity	NPC38699
0.8393	Intermediate Similarity	NPC88557
0.8387	Intermediate Similarity	NPC133934
0.8387	Intermediate Similarity	NPC184641
0.8387	Intermediate Similarity	NPC184684
0.8377	Intermediate Similarity	NPC226547
0.8375	Intermediate Similarity	NPC164082
0.8375	Intermediate Similarity	NPC210642
0.8375	Intermediate Similarity	NPC13985
0.8373	Intermediate Similarity	NPC475865
0.8364	Intermediate Similarity	NPC319749
0.8355	Intermediate Similarity	NPC236522
0.8353	Intermediate Similarity	NPC474568
0.8353	Intermediate Similarity	NPC477881
0.8344	Intermediate Similarity	NPC477702
0.8344	Intermediate Similarity	NPC228357
0.8333	Intermediate Similarity	NPC136757
0.8333	Intermediate Similarity	NPC42230
0.8333	Intermediate Similarity	NPC273578
0.8333	Intermediate Similarity	NPC311912
0.8323	Intermediate Similarity	NPC475953
0.8313	Intermediate Similarity	NPC472709
0.8313	Intermediate Similarity	NPC149505
0.8313	Intermediate Similarity	NPC472710
0.8313	Intermediate Similarity	NPC249070
0.8313	Intermediate Similarity	NPC280778
0.8303	Intermediate Similarity	NPC474770
0.8301	Intermediate Similarity	NPC32189
0.8301	Intermediate Similarity	NPC11453
0.8294	Intermediate Similarity	NPC471181
0.8293	Intermediate Similarity	NPC115281
0.8293	Intermediate Similarity	NPC181168
0.8293	Intermediate Similarity	NPC163527
0.828	Intermediate Similarity	NPC474036
0.8278	Intermediate Similarity	NPC102256
0.8274	Intermediate Similarity	NPC306475
0.8272	Intermediate Similarity	NPC299706
0.8272	Intermediate Similarity	NPC178574
0.8272	Intermediate Similarity	NPC115466
0.8272	Intermediate Similarity	NPC61604
0.8272	Intermediate Similarity	NPC245615
0.8272	Intermediate Similarity	NPC65591
0.8269	Intermediate Similarity	NPC40237
0.8269	Intermediate Similarity	NPC151423
0.8263	Intermediate Similarity	NPC469475
0.8263	Intermediate Similarity	NPC469518
0.8263	Intermediate Similarity	NPC116759
0.8263	Intermediate Similarity	NPC14294
0.8258	Intermediate Similarity	NPC46591
0.8258	Intermediate Similarity	NPC103448
0.8258	Intermediate Similarity	NPC216434
0.8253	Intermediate Similarity	NPC191352
0.8253	Intermediate Similarity	NPC258322
0.825	Intermediate Similarity	NPC293757
0.825	Intermediate Similarity	NPC474965
0.825	Intermediate Similarity	NPC668
0.825	Intermediate Similarity	NPC477695
0.825	Intermediate Similarity	NPC174512
0.8247	Intermediate Similarity	NPC283949
0.8242	Intermediate Similarity	NPC328122
0.8239	Intermediate Similarity	NPC39657
0.8235	Intermediate Similarity	NPC150534
0.8228	Intermediate Similarity	NPC180953
0.8225	Intermediate Similarity	NPC185498
0.8225	Intermediate Similarity	NPC474948
0.8224	Intermediate Similarity	NPC196937
0.8221	Intermediate Similarity	NPC473736
0.8214	Intermediate Similarity	NPC477884
0.8212	Intermediate Similarity	NPC184928
0.8212	Intermediate Similarity	NPC141493
0.821	Intermediate Similarity	NPC477699
0.8208	Intermediate Similarity	NPC477882

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 NPC63061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	917
0.2-0.3	1995
0.3-0.4	2698
0.4-0.5	1738
0.5-0.6	919
0.6-0.7	505
0.7-0.8	82
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8616	High Similarity	NPD37	Approved
0.8571	High Similarity	NPD4965	Approved
0.8571	High Similarity	NPD4967	Phase 2
0.8571	High Similarity	NPD4966	Approved
0.8485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7199	Phase 2
0.8354	Intermediate Similarity	NPD6234	Discontinued
0.8225	Intermediate Similarity	NPD7228	Approved
0.8035	Intermediate Similarity	NPD7240	Approved
0.7701	Intermediate Similarity	NPD3818	Discontinued
0.7684	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3787	Discontinued
0.7643	Intermediate Similarity	NPD6355	Discontinued
0.764	Intermediate Similarity	NPD6674	Discontinued
0.7633	Intermediate Similarity	NPD3817	Phase 2
0.7625	Intermediate Similarity	NPD5763	Approved
0.7625	Intermediate Similarity	NPD5762	Approved
0.759	Intermediate Similarity	NPD1653	Approved
0.7584	Intermediate Similarity	NPD7808	Phase 3
0.758	Intermediate Similarity	NPD4060	Phase 1
0.7557	Intermediate Similarity	NPD5844	Phase 1
0.7556	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3705	Approved
0.7528	Intermediate Similarity	NPD7251	Discontinued
0.7514	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3882	Suspended
0.7472	Intermediate Similarity	NPD6797	Phase 2
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7054	Approved
0.7452	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7473	Discontinued
0.7425	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7472	Approved
0.7403	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD3751	Discontinued
0.7394	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7095	Approved
0.7371	Intermediate Similarity	NPD6232	Discontinued
0.7368	Intermediate Similarity	NPD8455	Phase 2
0.7368	Intermediate Similarity	NPD1465	Phase 2
0.7349	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7329	Intermediate Similarity	NPD7097	Phase 1
0.7288	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6166	Phase 2
0.7288	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5494	Approved
0.7241	Intermediate Similarity	NPD7075	Discontinued
0.7241	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7680	Approved
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7225	Intermediate Similarity	NPD5402	Approved
0.7216	Intermediate Similarity	NPD8127	Discontinued
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1934	Approved
0.72	Intermediate Similarity	NPD919	Approved
0.7195	Intermediate Similarity	NPD7266	Discontinued
0.7169	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4110	Phase 3
0.7166	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.7126	Intermediate Similarity	NPD6190	Approved
0.711	Intermediate Similarity	NPD6801	Discontinued
0.7107	Intermediate Similarity	NPD4908	Phase 1
0.7101	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6842	Approved
0.7097	Intermediate Similarity	NPD6841	Approved
0.7097	Intermediate Similarity	NPD6843	Phase 3
0.7093	Intermediate Similarity	NPD6599	Discontinued
0.7081	Intermediate Similarity	NPD6233	Phase 2
0.7074	Intermediate Similarity	NPD7296	Approved
0.7069	Intermediate Similarity	NPD2801	Approved
0.7069	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4625	Phase 3
0.7052	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3018	Phase 2
0.703	Intermediate Similarity	NPD6099	Approved
0.703	Intermediate Similarity	NPD6100	Approved
0.7029	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1247	Approved
0.7019	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD2533	Approved
0.7	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD2532	Approved
0.6994	Remote Similarity	NPD5124	Phase 1
0.6994	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1091	Approved
0.6987	Remote Similarity	NPD1610	Phase 2
0.6973	Remote Similarity	NPD8313	Approved
0.6973	Remote Similarity	NPD8312	Approved
0.697	Remote Similarity	NPD7033	Discontinued
0.6968	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3750	Approved
0.6959	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6653	Approved
0.6946	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2861	Phase 2
0.6936	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4140	Approved
0.6928	Remote Similarity	NPD6032	Approved
0.6928	Remote Similarity	NPD2438	Suspended
0.6919	Remote Similarity	NPD7549	Discontinued
0.6914	Remote Similarity	NPD7985	Registered
0.6905	Remote Similarity	NPD1652	Phase 2
0.6905	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1357	Approved
0.6901	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2983	Phase 2
0.6899	Remote Similarity	NPD2982	Phase 2
0.6899	Remote Similarity	NPD4749	Approved
0.6886	Remote Similarity	NPD6005	Phase 3
0.6886	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6004	Phase 3
0.6886	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6002	Phase 3
0.6882	Remote Similarity	NPD5058	Phase 3
0.6875	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4062	Phase 3
0.6867	Remote Similarity	NPD3748	Approved
0.6864	Remote Similarity	NPD4628	Phase 3
0.6864	Remote Similarity	NPD3892	Phase 2
0.6864	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1512	Approved
0.6854	Remote Similarity	NPD3749	Approved
0.6845	Remote Similarity	NPD2424	Discontinued
0.6845	Remote Similarity	NPD5958	Discontinued
0.6842	Remote Similarity	NPD5283	Phase 1
0.6835	Remote Similarity	NPD2981	Phase 2
0.6835	Remote Similarity	NPD1608	Approved
0.6833	Remote Similarity	NPD6959	Discontinued
0.6816	Remote Similarity	NPD5709	Phase 3
0.681	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7435	Discontinued
0.68	Remote Similarity	NPD7028	Phase 2
0.6798	Remote Similarity	NPD7768	Phase 2
0.6786	Remote Similarity	NPD1375	Discontinued
0.678	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4666	Phase 3
0.6772	Remote Similarity	NPD422	Phase 1
0.6761	Remote Similarity	NPD5089	Approved
0.6761	Remote Similarity	NPD5090	Approved
0.6753	Remote Similarity	NPD2975	Approved
0.6753	Remote Similarity	NPD2974	Approved
0.6753	Remote Similarity	NPD2973	Approved
0.6751	Remote Similarity	NPD5005	Approved
0.6751	Remote Similarity	NPD5006	Approved
0.675	Remote Similarity	NPD1283	Approved
0.6746	Remote Similarity	NPD2897	Discontinued
0.6746	Remote Similarity	NPD4534	Discontinued
0.6744	Remote Similarity	NPD4357	Discontinued
0.6744	Remote Similarity	NPD1511	Approved
0.6743	Remote Similarity	NPD4005	Discontinued
0.6743	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5353	Approved
0.6735	Remote Similarity	NPD4580	Approved
0.6731	Remote Similarity	NPD1548	Phase 1
0.6727	Remote Similarity	NPD2979	Phase 3
0.6727	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD3620	Phase 2
0.6716	Remote Similarity	NPD8151	Discontinued
0.6708	Remote Similarity	NPD2797	Approved
0.6705	Remote Similarity	NPD4380	Phase 2
0.6688	Remote Similarity	NPD5585	Approved
0.6687	Remote Similarity	NPD230	Phase 1
0.6687	Remote Similarity	NPD1933	Approved
0.6687	Remote Similarity	NPD5735	Approved
0.6687	Remote Similarity	NPD447	Suspended
0.6686	Remote Similarity	NPD3687	Approved
0.6686	Remote Similarity	NPD3686	Approved
0.6686	Remote Similarity	NPD6666	Approved
0.6686	Remote Similarity	NPD6667	Approved
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD5242	Approved
0.665	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7783	Phase 2
0.6648	Remote Similarity	NPD2563	Approved
0.6648	Remote Similarity	NPD2560	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