NPASS Compound

Structure

CID29727 OpenBabel06191715352D 38 42 0 0 1 0 0 0 0 0999 V2000 0.4273 -3.2718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9736 3.2676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7993 -1.6298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0514 2.2163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7840 3.0689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1144 2.2617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5127 -0.1602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7162 -2.4106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1826 -2.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3179 0.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5399 1.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4243 -1.2854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7840 -2.4106 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7679 1.4147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3753 -1.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7840 -0.1602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7840 1.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9899 -1.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3753 -0.8193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7162 -0.1602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7162 1.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9899 -0.8193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1823 0.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1826 -0.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 -0.8193 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3015 0.7720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 -1.7515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9486 1.2898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4494 1.3243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4426 -2.4910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5533 2.3944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3179 2.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1823 2.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0466 0.6471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0577 0.4661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8764 -2.0395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8764 -0.5313 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 13 1 0 0 0 0 2 14 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 34 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 35 1 0 0 0 0 12 36 1 0 0 0 0 12 37 1 0 0 0 0 13 27 1 6 0 0 0 14 28 1 6 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 32 1 0 0 0 0 18 22 2 0 0 0 0 18 36 1 0 0 0 0 19 20 1 0 0 0 0 19 24 2 0 0 0 0 20 23 2 0 0 0 0 21 23 1 0 0 0 0 21 33 1 0 0 0 0 22 24 1 0 0 0 0 22 37 1 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 25 27 1 1 0 0 0 25 38 1 0 0 0 0 26 28 1 0 0 0 0 26 29 2 0 0 0 0 26 38 1 0 0 0 0 27 3 1 1 0 0 0 27 30 1 0 0 0 0 28 4 1 1 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.22
Volume:	519.509
LogP:	3.821
LogD:	2.952
LogS:	-4.651
# Rotatable Bonds:	3
TPSA:	122.14
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	5.747
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:	-4.817
MDCK Permeability:	2.6849311325349845e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	79.16891479492188%
Volume Distribution (VD):	0.847
Pgp-substrate:	8.458150863647461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.117
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.282
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.129
CYP2D6-substrate:	0.394
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.753

ADMET: Excretion

Clearance (CL):	4.756
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.209
Human Hepatotoxicity (H-HT):	0.291
Drug-inuced Liver Injury (DILI):	0.692
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.486
Skin Sensitization:	0.095
Carcinogencity:	0.431
Eye Corrosion:	0.003
Eye Irritation:	0.329
Respiratory Toxicity:	0.604

Download Data

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

Natural Product: NPC29727

Natural Product ID:	NPC29727
*Common Name:**	VLLFEMVDMFTBHG-KMIFWYFFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VLLFEMVDMFTBHG-KMIFWYFFSA-N
Standard InCHI:	InChI=1S/C28H34O10/c1-13-8-15-9-18-22(37-12-36-18)24-19(15)20-16(10-17(32-5)21(33-6)23(20)34-7)25(27(13,3)30)38-26(29)28(4,31)14(2)11-35-24/h9-10,13-14,25,30-31H,8,11-12H2,1-7H3/t13-,14+,25-,27-,28+/m0/s1
SMILES:	C[C@H]1Cc2cc3c(c4c2-c2c(cc(c(c2OC)OC)OC)[C@@H]([C@@]1(C)O)OC(=O)[C@@](C)([C@H](C)CO4)O)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386340
PubChem CID:	5317799
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
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	Stems	Luoji Mountain Village, Xichang County, Sicuan Province, China	2011-Sep	PMID[23738539]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29191	Schisandra neglecta	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	185700.0	nM	PMID[483179]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	9800.0	nM	PMID[483179]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	18.9	n.a.	PMID[483179]

☑ 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 NPC29727 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	1431
0.2-0.3	3645
0.3-0.4	8774
0.4-0.5	10043
0.5-0.6	4299
0.6-0.7	7377
0.7-0.8	6184
0.8-0.85	469
0.85-0.9	104
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9671	High Similarity	NPC63061
0.947	High Similarity	NPC473425
0.9404	High Similarity	NPC217708
0.9404	High Similarity	NPC297271
0.9404	High Similarity	NPC16791
0.9404	High Similarity	NPC77237
0.9404	High Similarity	NPC474606
0.9404	High Similarity	NPC53669
0.9404	High Similarity	NPC308739
0.9404	High Similarity	NPC126405
0.94	High Similarity	NPC224472
0.9338	High Similarity	NPC471154
0.9324	High Similarity	NPC321696
0.9324	High Similarity	NPC321958
0.9281	High Similarity	NPC238834
0.9272	High Similarity	NPC475756
0.9257	High Similarity	NPC327651
0.9257	High Similarity	NPC318286
0.9221	High Similarity	NPC473323
0.9216	High Similarity	NPC198461
0.92	High Similarity	NPC325720
0.92	High Similarity	NPC316676
0.9189	High Similarity	NPC326144
0.9161	High Similarity	NPC475592
0.9156	High Similarity	NPC476065
0.915	High Similarity	NPC24562
0.9122	High Similarity	NPC76415
0.9122	High Similarity	NPC218510
0.9079	High Similarity	NPC316989
0.9079	High Similarity	NPC473989
0.9073	High Similarity	NPC477375
0.9073	High Similarity	NPC327352
0.9073	High Similarity	NPC252281
0.9073	High Similarity	NPC198129
0.9073	High Similarity	NPC477879
0.902	High Similarity	NPC303519
0.9013	High Similarity	NPC477374
0.9013	High Similarity	NPC477376
0.9013	High Similarity	NPC322426
0.9007	High Similarity	NPC295297
0.8968	High Similarity	NPC312763
0.8889	High Similarity	NPC85141
0.8882	High Similarity	NPC320471
0.8882	High Similarity	NPC137352
0.8882	High Similarity	NPC118162
0.8882	High Similarity	NPC183083
0.8882	High Similarity	NPC83049
0.8867	High Similarity	NPC324962
0.8861	High Similarity	NPC241600
0.8861	High Similarity	NPC230531
0.8861	High Similarity	NPC215400
0.8861	High Similarity	NPC173726
0.8851	High Similarity	NPC201404
0.8851	High Similarity	NPC53722
0.8851	High Similarity	NPC290714
0.8846	High Similarity	NPC178195
0.8846	High Similarity	NPC348849
0.8839	High Similarity	NPC302610
0.8831	High Similarity	NPC470916
0.8831	High Similarity	NPC477381
0.882	High Similarity	NPC222531
0.8816	High Similarity	NPC474054
0.8808	High Similarity	NPC87883
0.8808	High Similarity	NPC73467
0.8808	High Similarity	NPC121661
0.88	High Similarity	NPC103637
0.88	High Similarity	NPC230538
0.88	High Similarity	NPC229172
0.88	High Similarity	NPC36531
0.8784	High Similarity	NPC865
0.8782	High Similarity	NPC149735
0.8782	High Similarity	NPC477377
0.8774	High Similarity	NPC477379
0.8766	High Similarity	NPC474393
0.8766	High Similarity	NPC474347
0.875	High Similarity	NPC166506
0.875	High Similarity	NPC475868
0.875	High Similarity	NPC197352
0.875	High Similarity	NPC110763
0.875	High Similarity	NPC189239
0.8734	High Similarity	NPC477380
0.8718	High Similarity	NPC477378
0.8718	High Similarity	NPC475229
0.8712	High Similarity	NPC79322
0.871	High Similarity	NPC24425
0.8701	High Similarity	NPC304821
0.8693	High Similarity	NPC252286
0.8693	High Similarity	NPC154971
0.8688	High Similarity	NPC119910
0.8684	High Similarity	NPC239254
0.8684	High Similarity	NPC172171
0.8679	High Similarity	NPC19947
0.8679	High Similarity	NPC207584
0.8679	High Similarity	NPC477885
0.8675	High Similarity	NPC133934
0.8675	High Similarity	NPC287124
0.8675	High Similarity	NPC184684
0.8675	High Similarity	NPC184641
0.8671	High Similarity	NPC117154
0.8662	High Similarity	NPC245948
0.8662	High Similarity	NPC474514
0.8659	High Similarity	NPC88557
0.8634	High Similarity	NPC152424
0.8634	High Similarity	NPC100465
0.8634	High Similarity	NPC115624
0.8627	High Similarity	NPC477702
0.8625	High Similarity	NPC325122
0.8616	High Similarity	NPC237946
0.8616	High Similarity	NPC32373
0.8616	High Similarity	NPC163635
0.8606	High Similarity	NPC477883
0.8598	High Similarity	NPC311912
0.8591	High Similarity	NPC143895
0.859	High Similarity	NPC229882
0.859	High Similarity	NPC158635
0.8581	High Similarity	NPC145722
0.8581	High Similarity	NPC270751
0.8581	High Similarity	NPC256776
0.8581	High Similarity	NPC185680
0.8571	High Similarity	NPC96593
0.8571	High Similarity	NPC212890
0.8571	High Similarity	NPC91634
0.8571	High Similarity	NPC268718
0.8571	High Similarity	NPC150943
0.8562	High Similarity	NPC163527
0.8562	High Similarity	NPC166884
0.8562	High Similarity	NPC141569
0.8562	High Similarity	NPC18211
0.8562	High Similarity	NPC143092
0.8562	High Similarity	NPC181168
0.8562	High Similarity	NPC115281
0.8562	High Similarity	NPC477701
0.8535	High Similarity	NPC13985
0.8535	High Similarity	NPC210642
0.8526	High Similarity	NPC174512
0.8526	High Similarity	NPC477695
0.8526	High Similarity	NPC474965
0.8526	High Similarity	NPC477698
0.8526	High Similarity	NPC668
0.8526	High Similarity	NPC293757
0.8519	High Similarity	NPC319749
0.8519	High Similarity	NPC288149
0.8503	High Similarity	NPC477881
0.85	High Similarity	NPC228357
0.8491	Intermediate Similarity	NPC273578
0.8491	Intermediate Similarity	NPC473736
0.8491	Intermediate Similarity	NPC136757
0.8485	Intermediate Similarity	NPC471180
0.8481	Intermediate Similarity	NPC56184
0.8481	Intermediate Similarity	NPC477699
0.8477	Intermediate Similarity	NPC471183
0.8476	Intermediate Similarity	NPC474647
0.8471	Intermediate Similarity	NPC472709
0.8471	Intermediate Similarity	NPC472710
0.8471	Intermediate Similarity	NPC149505
0.8467	Intermediate Similarity	NPC11453
0.8467	Intermediate Similarity	NPC32189
0.8466	Intermediate Similarity	NPC280778
0.8466	Intermediate Similarity	NPC469512
0.8446	Intermediate Similarity	NPC102256
0.8443	Intermediate Similarity	NPC471181
0.8442	Intermediate Similarity	NPC474036
0.8438	Intermediate Similarity	NPC38699
0.8431	Intermediate Similarity	NPC40237
0.8431	Intermediate Similarity	NPC151423
0.8428	Intermediate Similarity	NPC299706
0.8428	Intermediate Similarity	NPC115466
0.8428	Intermediate Similarity	NPC61604
0.8428	Intermediate Similarity	NPC475141
0.8428	Intermediate Similarity	NPC178574
0.8428	Intermediate Similarity	NPC65591
0.8428	Intermediate Similarity	NPC245615
0.8424	Intermediate Similarity	NPC306475
0.8421	Intermediate Similarity	NPC226547
0.8421	Intermediate Similarity	NPC103448
0.8421	Intermediate Similarity	NPC216434
0.8418	Intermediate Similarity	NPC477700
0.8418	Intermediate Similarity	NPC164082
0.8415	Intermediate Similarity	NPC469475
0.8415	Intermediate Similarity	NPC475865
0.8415	Intermediate Similarity	NPC14294
0.8415	Intermediate Similarity	NPC116759
0.8415	Intermediate Similarity	NPC469518
0.8408	Intermediate Similarity	NPC216223
0.8408	Intermediate Similarity	NPC145569
0.8405	Intermediate Similarity	NPC191352
0.8405	Intermediate Similarity	NPC258322
0.84	Intermediate Similarity	NPC236522
0.8397	Intermediate Similarity	NPC39657
0.8395	Intermediate Similarity	NPC328122
0.8393	Intermediate Similarity	NPC474568
0.8387	Intermediate Similarity	NPC180953
0.8387	Intermediate Similarity	NPC307466
0.8378	Intermediate Similarity	NPC141493
0.8378	Intermediate Similarity	NPC184928
0.8377	Intermediate Similarity	NPC470811
0.8377	Intermediate Similarity	NPC81638
0.8377	Intermediate Similarity	NPC477696
0.8377	Intermediate Similarity	NPC477697
0.8375	Intermediate Similarity	NPC30009

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 NPC29727 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	896
0.2-0.3	1946
0.3-0.4	2692
0.4-0.5	1768
0.5-0.6	929
0.6-0.7	524
0.7-0.8	98
0.8-0.85	1
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8662	High Similarity	NPD37	Approved
0.8642	High Similarity	NPD7184	Clinical (unspecified phase)
0.8625	High Similarity	NPD6234	Discontinued
0.8616	High Similarity	NPD4967	Phase 2
0.8616	High Similarity	NPD4966	Approved
0.8616	High Similarity	NPD4965	Approved
0.8519	High Similarity	NPD7199	Phase 2
0.8373	Intermediate Similarity	NPD7228	Approved
0.8176	Intermediate Similarity	NPD7240	Approved
0.7836	Intermediate Similarity	NPD3818	Discontinued
0.7792	Intermediate Similarity	NPD6355	Discontinued
0.7785	Intermediate Similarity	NPD6674	Discontinued
0.7784	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.773	Intermediate Similarity	NPD1653	Approved
0.7727	Intermediate Similarity	NPD4060	Phase 1
0.7725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3787	Discontinued
0.7703	Intermediate Similarity	NPD3705	Approved
0.7658	Intermediate Similarity	NPD5762	Approved
0.7658	Intermediate Similarity	NPD5763	Approved
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7644	Intermediate Similarity	NPD7074	Phase 3
0.7627	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3882	Suspended
0.7614	Intermediate Similarity	NPD7808	Phase 3
0.7613	Intermediate Similarity	NPD1613	Approved
0.7613	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1465	Phase 2
0.7602	Intermediate Similarity	NPD7229	Phase 3
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5844	Phase 1
0.7586	Intermediate Similarity	NPD7054	Approved
0.7572	Intermediate Similarity	NPD7473	Discontinued
0.7561	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7251	Discontinued
0.7543	Intermediate Similarity	NPD7472	Approved
0.7532	Intermediate Similarity	NPD7095	Approved
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7097	Phase 1
0.7458	Intermediate Similarity	NPD6559	Discontinued
0.744	Intermediate Similarity	NPD1934	Approved
0.7429	Intermediate Similarity	NPD3751	Discontinued
0.7414	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6166	Phase 2
0.7414	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7819	Suspended
0.7394	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5494	Approved
0.7372	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD7075	Discontinued
0.7354	Intermediate Similarity	NPD7680	Approved
0.7329	Intermediate Similarity	NPD7266	Discontinued
0.7301	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4110	Phase 3
0.7294	Intermediate Similarity	NPD2801	Approved
0.7294	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7296	Approved
0.7273	Intermediate Similarity	NPD6799	Approved
0.7267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7257	Intermediate Similarity	NPD3926	Phase 2
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7251	Intermediate Similarity	NPD5402	Approved
0.7244	Intermediate Similarity	NPD4908	Phase 1
0.7241	Intermediate Similarity	NPD8127	Discontinued
0.7225	Intermediate Similarity	NPD919	Approved
0.7219	Intermediate Similarity	NPD6599	Discontinued
0.7215	Intermediate Similarity	NPD6233	Phase 2
0.7213	Intermediate Similarity	NPD6841	Approved
0.7213	Intermediate Similarity	NPD6842	Approved
0.7213	Intermediate Similarity	NPD6843	Phase 3
0.7197	Intermediate Similarity	NPD4625	Phase 3
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3018	Phase 2
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6801	Discontinued
0.7126	Intermediate Similarity	NPD2532	Approved
0.7126	Intermediate Similarity	NPD2534	Approved
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2533	Approved
0.7124	Intermediate Similarity	NPD1610	Phase 2
0.7124	Intermediate Similarity	NPD1091	Approved
0.7091	Intermediate Similarity	NPD3750	Approved
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD1512	Approved
0.7083	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6653	Approved
0.7073	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2438	Suspended
0.7055	Intermediate Similarity	NPD6032	Approved
0.7052	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1247	Approved
0.7044	Intermediate Similarity	NPD7985	Registered
0.7044	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5403	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.7032	Intermediate Similarity	NPD2983	Phase 2
0.7032	Intermediate Similarity	NPD4749	Approved
0.7032	Intermediate Similarity	NPD2982	Phase 2
0.703	Intermediate Similarity	NPD1652	Phase 2
0.703	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5401	Approved
0.7024	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD5058	Phase 3
0.7	Intermediate Similarity	NPD4062	Phase 3
0.6994	Remote Similarity	NPD3748	Approved
0.6994	Remote Similarity	NPD7033	Discontinued
0.6988	Remote Similarity	NPD4628	Phase 3
0.6988	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5283	Phase 1
0.6971	Remote Similarity	NPD3749	Approved
0.697	Remote Similarity	NPD2424	Discontinued
0.697	Remote Similarity	NPD5958	Discontinued
0.6968	Remote Similarity	NPD1608	Approved
0.6968	Remote Similarity	NPD2981	Phase 2
0.6964	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD4140	Approved
0.6949	Remote Similarity	NPD6959	Discontinued
0.6937	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1357	Approved
0.6923	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7028	Phase 2
0.6914	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD230	Phase 1
0.6909	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6004	Phase 3
0.6909	Remote Similarity	NPD6005	Phase 3
0.6909	Remote Similarity	NPD1375	Discontinued
0.6909	Remote Similarity	NPD6002	Phase 3
0.6903	Remote Similarity	NPD422	Phase 1
0.6899	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3892	Phase 2
0.6879	Remote Similarity	NPD1283	Approved
0.6867	Remote Similarity	NPD4534	Discontinued
0.6864	Remote Similarity	NPD4357	Discontinued
0.6863	Remote Similarity	NPD1548	Phase 1
0.6857	Remote Similarity	NPD5353	Approved
0.6857	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5006	Approved
0.6856	Remote Similarity	NPD5005	Approved
0.6852	Remote Similarity	NPD3620	Phase 2
0.6852	Remote Similarity	NPD2979	Phase 3
0.6852	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2797	Approved
0.6821	Remote Similarity	NPD4380	Phase 2
0.6821	Remote Similarity	NPD7435	Discontinued
0.6818	Remote Similarity	NPD5585	Approved
0.6818	Remote Similarity	NPD8151	Discontinued
0.6815	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.681	Remote Similarity	NPD447	Suspended
0.681	Remote Similarity	NPD1933	Approved
0.681	Remote Similarity	NPD5735	Approved
0.68	Remote Similarity	NPD7827	Phase 1
0.6798	Remote Similarity	NPD4666	Phase 3
0.6795	Remote Similarity	NPD1611	Approved
0.6782	Remote Similarity	NPD5089	Approved
0.6782	Remote Similarity	NPD7411	Suspended
0.6782	Remote Similarity	NPD5090	Approved
0.6778	Remote Similarity	NPD5242	Approved
0.6776	Remote Similarity	NPD7157	Approved
0.6774	Remote Similarity	NPD17	Approved
0.6774	Remote Similarity	NPD1778	Approved
0.6772	Remote Similarity	NPD6696	Suspended
0.6771	Remote Similarity	NPD2973	Approved
0.6771	Remote Similarity	NPD2974	Approved
0.6771	Remote Similarity	NPD2975	Approved
0.6766	Remote Similarity	NPD2897	Discontinued
0.6763	Remote Similarity	NPD4005	Discontinued
0.6763	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4580	Approved
0.675	Remote Similarity	NPD7783	Phase 2
0.675	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4477	Approved
0.6747	Remote Similarity	NPD4476	Approved
0.6747	Remote Similarity	NPD2796	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