NPASS Compound

Structure

CID191352 OpenBabel06191715572D 37 42 0 0 1 0 0 0 0 0999 V2000 -1.6148 -5.7475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8064 -4.5559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0333 -0.3725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5687 -0.9078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2093 -2.3560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4520 -1.7750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0847 -3.3024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5701 -2.1402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2028 -3.6677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2950 -4.8656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2067 -4.6679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7268 -1.7345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5022 -3.7134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7722 0.5611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2495 -4.8656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9245 -4.1907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4455 -3.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3800 -4.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2495 -2.5611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0333 -4.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2495 -0.9078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3800 -3.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2950 -2.5611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9245 -3.2361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0333 -3.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2950 -0.9078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2067 -2.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1823 -1.7345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5637 -3.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4391 -4.3983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2067 -0.8497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0914 -1.7345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9411 -4.4856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5445 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9411 -2.9411 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 -2.8064 -2.8708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 13 33 1 0 0 0 0 13 35 1 0 0 0 0 14 34 1 0 0 0 0 14 36 1 0 0 0 0 15 1 1 6 0 0 0 15 16 1 0 0 0 0 16 2 1 6 0 0 0 16 24 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 20 33 1 0 0 0 0 21 26 2 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 27 2 0 0 0 0 23 28 2 0 0 0 0 24 37 1 1 0 0 0 25 27 1 0 0 0 0 25 35 1 0 0 0 0 26 28 1 0 0 0 0 26 36 1 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 29 30 2 0 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.18
Volume:	502.759
LogP:	5.279
LogD:	4.322
LogS:	-6.386
# Rotatable Bonds:	5
TPSA:	81.68
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	3.91
Fsp3:	0.345
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	4.046974936500192e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	94.16593170166016%
Volume Distribution (VD):	0.718
Pgp-substrate:	1.2917441129684448%

ADMET: Metabolism

CYP1A2-inhibitor:	0.185
CYP1A2-substrate:	0.476
CYP2C19-inhibitor:	0.984
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.958
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.369
CYP2D6-substrate:	0.667
CYP3A4-inhibitor:	0.968
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	11.422
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.208
Skin Sensitization:	0.235
Carcinogencity:	0.86
Eye Corrosion:	0.003
Eye Irritation:	0.363
Respiratory Toxicity:	0.394

Download Data

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

Natural Product: NPC191352

Natural Product ID:	NPC191352
*Common Name:**	Interiotherin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MBGKPRSARHEFAG-CCHLGUQTSA-N
Standard InCHI:	InChI=1S/C29H28O8/c1-15-10-18-11-20-25(35-13-33-20)27(31-3)22(18)23-19(12-21-26(28(23)32-4)36-14-34-21)24(16(15)2)37-29(30)17-8-6-5-7-9-17/h5-9,11-12,15-16,24H,10,13-14H2,1-4H3/t15-,16-,24+/m0/s1
SMILES:	COc1c2OCOc2cc2c1c1c(C[C@@H]([C@@H]([C@H]2OC(=O)c2ccccc2)C)C)cc2c(c1OC)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484669
PubChem CID:	21125391
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
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350139]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8946749]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14102	Kadsura interior	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]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14102	Kadsura interior	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
IC50	1
Others	6

Activity Type	# Activity
Cell Line	2
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	EC50	=	3.1	ug.mL-1	PMID[542193]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[542194]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	41.0	ug.mL-1	PMID[542193]
NPT27	Others	Unspecified		TI	=	13.2	n.a.	PMID[542193]
NPT2	Others	Unspecified		Activity	=	18.3	%	PMID[542194]
NPT2	Others	Unspecified		Activity	=	60.1	%	PMID[542194]
NPT2	Others	Unspecified		Activity	=	85.7	%	PMID[542194]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[542194]

☑ 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 NPC191352 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	430
0.1-0.2	1550
0.2-0.3	3452
0.3-0.4	8696
0.4-0.5	10039
0.5-0.6	3508
0.6-0.7	6147
0.7-0.8	8154
0.8-0.85	560
0.85-0.9	119
0.9-0.95	33
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC258322
0.974	High Similarity	NPC319749
0.9682	High Similarity	NPC79322
0.9677	High Similarity	NPC280778
0.9554	High Similarity	NPC477884
0.9494	High Similarity	NPC320471
0.9494	High Similarity	NPC83049
0.9494	High Similarity	NPC118162
0.9477	High Similarity	NPC348849
0.9477	High Similarity	NPC178195
0.9434	High Similarity	NPC311912
0.9375	High Similarity	NPC88557
0.9359	High Similarity	NPC325122
0.9286	High Similarity	NPC477377
0.9281	High Similarity	NPC303519
0.9276	High Similarity	NPC85141
0.9236	High Similarity	NPC474043
0.9231	High Similarity	NPC477380
0.9221	High Similarity	NPC477378
0.9221	High Similarity	NPC475229
0.9202	High Similarity	NPC477881
0.9182	High Similarity	NPC61141
0.9172	High Similarity	NPC477885
0.9108	High Similarity	NPC115123
0.9108	High Similarity	NPC239113
0.9097	High Similarity	NPC104353
0.9091	High Similarity	NPC316989
0.9085	High Similarity	NPC198129
0.9085	High Similarity	NPC477375
0.9085	High Similarity	NPC327352
0.9085	High Similarity	NPC252281
0.908	High Similarity	NPC477883
0.9045	High Similarity	NPC234730
0.9036	High Similarity	NPC477880
0.9036	High Similarity	NPC477882
0.9032	High Similarity	NPC210642
0.9032	High Similarity	NPC13985
0.9026	High Similarity	NPC477376
0.9026	High Similarity	NPC322426
0.9026	High Similarity	NPC477374
0.9012	High Similarity	NPC174734
0.9012	High Similarity	NPC474042
0.9006	High Similarity	NPC475865
0.8994	High Similarity	NPC125713
0.8981	High Similarity	NPC198461
0.8981	High Similarity	NPC273578
0.8981	High Similarity	NPC312763
0.8974	High Similarity	NPC220577
0.8968	High Similarity	NPC149505
0.8954	High Similarity	NPC321958
0.8954	High Similarity	NPC321696
0.8944	High Similarity	NPC473445
0.8944	High Similarity	NPC42797
0.8944	High Similarity	NPC249070
0.8938	High Similarity	NPC474770
0.8938	High Similarity	NPC78944
0.8931	High Similarity	NPC19600
0.8909	High Similarity	NPC469506
0.8902	High Similarity	NPC117911
0.8896	High Similarity	NPC471923
0.8889	High Similarity	NPC291977
0.8889	High Similarity	NPC327651
0.8889	High Similarity	NPC318286
0.8882	High Similarity	NPC209411
0.8882	High Similarity	NPC76415
0.8882	High Similarity	NPC239890
0.8882	High Similarity	NPC218510
0.8875	High Similarity	NPC230531
0.8875	High Similarity	NPC215400
0.8875	High Similarity	NPC328122
0.8868	High Similarity	NPC301897
0.8868	High Similarity	NPC473900
0.8855	High Similarity	NPC474568
0.8841	High Similarity	NPC473531
0.8841	High Similarity	NPC475453
0.8827	High Similarity	NPC22130
0.8827	High Similarity	NPC116838
0.8824	High Similarity	NPC475000
0.8824	High Similarity	NPC326144
0.882	High Similarity	NPC96593
0.8812	High Similarity	NPC207584
0.8812	High Similarity	NPC19947
0.8797	High Similarity	NPC53669
0.8797	High Similarity	NPC77237
0.8797	High Similarity	NPC474514
0.8797	High Similarity	NPC217708
0.8797	High Similarity	NPC297271
0.8797	High Similarity	NPC308739
0.8797	High Similarity	NPC24562
0.8797	High Similarity	NPC16791
0.8797	High Similarity	NPC126405
0.8795	High Similarity	NPC178737
0.8774	High Similarity	NPC304687
0.8774	High Similarity	NPC80230
0.8774	High Similarity	NPC101755
0.8774	High Similarity	NPC104024
0.8774	High Similarity	NPC65574
0.8766	High Similarity	NPC474158
0.8765	High Similarity	NPC15212
0.8765	High Similarity	NPC288149
0.875	High Similarity	NPC32373
0.875	High Similarity	NPC237946
0.875	High Similarity	NPC196771
0.8742	High Similarity	NPC54179
0.8727	High Similarity	NPC471180
0.8726	High Similarity	NPC473989
0.8718	High Similarity	NPC262804
0.8718	High Similarity	NPC40654
0.871	High Similarity	NPC193779
0.871	High Similarity	NPC87295
0.8701	High Similarity	NPC474036
0.8693	High Similarity	NPC40237
0.8693	High Similarity	NPC176586
0.8693	High Similarity	NPC210354
0.8693	High Similarity	NPC151423
0.8688	High Similarity	NPC238834
0.8688	High Similarity	NPC476065
0.8683	High Similarity	NPC471921
0.8683	High Similarity	NPC292712
0.8683	High Similarity	NPC473697
0.8683	High Similarity	NPC474075
0.8683	High Similarity	NPC471922
0.8683	High Similarity	NPC129930
0.8683	High Similarity	NPC471920
0.8683	High Similarity	NPC312006
0.8683	High Similarity	NPC20114
0.8683	High Similarity	NPC114550
0.8679	High Similarity	NPC308555
0.8671	High Similarity	NPC224472
0.8662	High Similarity	NPC127827
0.8662	High Similarity	NPC177476
0.8662	High Similarity	NPC262455
0.8636	High Similarity	NPC474288
0.8634	High Similarity	NPC473323
0.8631	High Similarity	NPC184624
0.8616	High Similarity	NPC118332
0.8614	High Similarity	NPC42230
0.8608	High Similarity	NPC475722
0.8606	High Similarity	NPC475953
0.8599	High Similarity	NPC325720
0.8599	High Similarity	NPC316676
0.8598	High Similarity	NPC198796
0.8589	High Similarity	NPC119910
0.8589	High Similarity	NPC268718
0.8589	High Similarity	NPC91634
0.8589	High Similarity	NPC150943
0.8581	High Similarity	NPC92693
0.8581	High Similarity	NPC218841
0.8581	High Similarity	NPC18211
0.8581	High Similarity	NPC191158
0.8581	High Similarity	NPC143092
0.8581	High Similarity	NPC177644
0.858	High Similarity	NPC181168
0.858	High Similarity	NPC475592
0.858	High Similarity	NPC163527
0.858	High Similarity	NPC115281
0.8571	High Similarity	NPC117154
0.8571	High Similarity	NPC254163
0.8571	High Similarity	NPC471181
0.8562	High Similarity	NPC245948
0.8562	High Similarity	NPC474606
0.8553	High Similarity	NPC475756
0.8545	High Similarity	NPC469475
0.8545	High Similarity	NPC469518
0.8537	High Similarity	NPC152424
0.8537	High Similarity	NPC100465
0.8519	High Similarity	NPC261484
0.8509	High Similarity	NPC473425
0.8503	High Similarity	NPC474948
0.85	High Similarity	NPC56184
0.85	High Similarity	NPC476434
0.85	High Similarity	NPC471154
0.8494	Intermediate Similarity	NPC222531
0.8494	Intermediate Similarity	NPC474647
0.8487	Intermediate Similarity	NPC32189
0.8487	Intermediate Similarity	NPC11453
0.8481	Intermediate Similarity	NPC304821
0.848	Intermediate Similarity	NPC35266
0.8476	Intermediate Similarity	NPC470637
0.8471	Intermediate Similarity	NPC193377
0.8466	Intermediate Similarity	NPC474990
0.8462	Intermediate Similarity	NPC38438
0.8447	Intermediate Similarity	NPC68882
0.8447	Intermediate Similarity	NPC475141
0.8442	Intermediate Similarity	NPC216434
0.8442	Intermediate Similarity	NPC103448
0.8438	Intermediate Similarity	NPC477700
0.8438	Intermediate Similarity	NPC32079
0.8438	Intermediate Similarity	NPC474975
0.8434	Intermediate Similarity	NPC14294
0.8434	Intermediate Similarity	NPC116759
0.8431	Intermediate Similarity	NPC865
0.843	Intermediate Similarity	NPC161609
0.843	Intermediate Similarity	NPC275690
0.8428	Intermediate Similarity	NPC477698
0.8428	Intermediate Similarity	NPC24193
0.8424	Intermediate Similarity	NPC115624
0.8421	Intermediate Similarity	NPC473713
0.8421	Intermediate Similarity	NPC472723
0.8418	Intermediate Similarity	NPC24257

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 NPC191352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	934
0.2-0.3	1619
0.3-0.4	2706
0.4-0.5	1891
0.5-0.6	1017
0.6-0.7	475
0.7-0.8	141
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD6980	Clinical (unspecified phase)
0.875	High Similarity	NPD4967	Phase 2
0.875	High Similarity	NPD4966	Approved
0.875	High Similarity	NPD4965	Approved
0.8642	High Similarity	NPD6234	Discontinued
0.8562	High Similarity	NPD37	Approved
0.8537	High Similarity	NPD7199	Phase 2
0.8434	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7228	Approved
0.8235	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6232	Discontinued
0.8118	Intermediate Similarity	NPD7473	Discontinued
0.8092	Intermediate Similarity	NPD7240	Approved
0.8072	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3818	Discontinued
0.8036	Intermediate Similarity	NPD5494	Approved
0.7904	Intermediate Similarity	NPD3817	Phase 2
0.7886	Intermediate Similarity	NPD6559	Discontinued
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3748	Approved
0.7771	Intermediate Similarity	NPD7074	Phase 3
0.7738	Intermediate Similarity	NPD1465	Phase 2
0.7738	Intermediate Similarity	NPD7819	Suspended
0.7714	Intermediate Similarity	NPD7054	Approved
0.7701	Intermediate Similarity	NPD5005	Approved
0.7701	Intermediate Similarity	NPD5006	Approved
0.7688	Intermediate Similarity	NPD3926	Phase 2
0.768	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1934	Approved
0.767	Intermediate Similarity	NPD7472	Approved
0.7661	Intermediate Similarity	NPD919	Approved
0.7644	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6166	Phase 2
0.764	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1933	Approved
0.7581	Intermediate Similarity	NPD4420	Approved
0.7556	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3750	Approved
0.7544	Intermediate Similarity	NPD3882	Suspended
0.7542	Intermediate Similarity	NPD7808	Phase 3
0.7529	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6797	Phase 2
0.7528	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD3705	Approved
0.7486	Intermediate Similarity	NPD5242	Approved
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7474	Intermediate Similarity	NPD7680	Approved
0.7447	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7768	Phase 2
0.744	Intermediate Similarity	NPD1653	Approved
0.7429	Intermediate Similarity	NPD7229	Phase 3
0.7427	Intermediate Similarity	NPD2801	Approved
0.7427	Intermediate Similarity	NPD8455	Phase 2
0.7427	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7411	Suspended
0.741	Intermediate Similarity	NPD6799	Approved
0.7407	Intermediate Similarity	NPD2438	Suspended
0.7403	Intermediate Similarity	NPD8312	Approved
0.7403	Intermediate Similarity	NPD8313	Approved
0.7399	Intermediate Similarity	NPD3749	Approved
0.7399	Intermediate Similarity	NPD7075	Discontinued
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5353	Approved
0.7384	Intermediate Similarity	NPD5402	Approved
0.7371	Intermediate Similarity	NPD8127	Discontinued
0.7371	Intermediate Similarity	NPD1247	Approved
0.7371	Intermediate Similarity	NPD6959	Discontinued
0.7368	Intermediate Similarity	NPD6801	Discontinued
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD2532	Approved
0.7353	Intermediate Similarity	NPD6599	Discontinued
0.7353	Intermediate Similarity	NPD4380	Phase 2
0.7312	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3764	Approved
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7283	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5403	Approved
0.7278	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5401	Approved
0.7247	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7003	Approved
0.7229	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6273	Approved
0.7209	Intermediate Similarity	NPD6385	Approved
0.7209	Intermediate Similarity	NPD6386	Approved
0.7205	Intermediate Similarity	NPD2979	Phase 3
0.7202	Intermediate Similarity	NPD1511	Approved
0.7195	Intermediate Similarity	NPD2935	Discontinued
0.7194	Intermediate Similarity	NPD8151	Discontinued
0.7188	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD1243	Approved
0.7167	Intermediate Similarity	NPD3751	Discontinued
0.716	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7151	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7134	Intermediate Similarity	NPD1510	Phase 2
0.7126	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3027	Phase 3
0.7118	Intermediate Similarity	NPD1512	Approved
0.7118	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1549	Phase 2
0.7097	Intermediate Similarity	NPD8434	Phase 2
0.7093	Intermediate Similarity	NPD3226	Approved
0.7083	Intermediate Similarity	NPD6190	Approved
0.7081	Intermediate Similarity	NPD6798	Discontinued
0.7066	Intermediate Similarity	NPD6674	Discontinued
0.7059	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.7055	Intermediate Similarity	NPD447	Suspended
0.7051	Intermediate Similarity	NPD1281	Approved
0.7048	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2798	Approved
0.7025	Intermediate Similarity	NPD1876	Approved
0.7024	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4110	Phase 3
0.7024	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3018	Phase 2
0.6994	Remote Similarity	NPD1240	Approved
0.6994	Remote Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4288	Approved
0.6988	Remote Similarity	NPD1551	Phase 2
0.6982	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7549	Discontinued
0.6957	Remote Similarity	NPD4908	Phase 1
0.6949	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5536	Phase 2
0.6946	Remote Similarity	NPD2346	Discontinued
0.6939	Remote Similarity	NPD7435	Discontinued
0.6933	Remote Similarity	NPD6233	Phase 2
0.6928	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD17	Approved
0.6919	Remote Similarity	NPD7038	Approved
0.6919	Remote Similarity	NPD7039	Approved
0.6919	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1283	Approved
0.6914	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6873	Phase 2
0.691	Remote Similarity	NPD6971	Discontinued
0.6909	Remote Similarity	NPD1607	Approved
0.6908	Remote Similarity	NPD5283	Phase 1
0.6899	Remote Similarity	NPD2981	Phase 2
0.689	Remote Similarity	NPD4307	Phase 2
0.6886	Remote Similarity	NPD5405	Approved
0.6886	Remote Similarity	NPD5406	Approved
0.6886	Remote Similarity	NPD5408	Approved
0.6886	Remote Similarity	NPD5404	Approved
0.6886	Remote Similarity	NPD2531	Phase 2
0.6875	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD3266	Approved
0.6875	Remote Similarity	NPD3267	Approved
0.6872	Remote Similarity	NPD6778	Approved
0.6872	Remote Similarity	NPD6779	Approved
0.6872	Remote Similarity	NPD6781	Approved
0.6872	Remote Similarity	NPD6776	Approved
0.6872	Remote Similarity	NPD6780	Approved
0.6872	Remote Similarity	NPD6782	Approved
0.6872	Remote Similarity	NPD6777	Approved
0.6871	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7783	Phase 2
0.6866	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5691	Approved
0.6855	Remote Similarity	NPD2983	Phase 2
0.6855	Remote Similarity	NPD2982	Phase 2
0.6852	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5710	Approved
0.6851	Remote Similarity	NPD5711	Approved
0.6847	Remote Similarity	NPD7930	Approved
0.6842	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6746	Phase 2
0.6829	Remote Similarity	NPD8032	Phase 2
0.6818	Remote Similarity	NPD7870	Phase 2
0.6818	Remote Similarity	NPD7871	Phase 2
0.6818	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2897	Discontinued
0.6802	Remote Similarity	NPD6823	Phase 2
0.6802	Remote Similarity	NPD7390	Discontinued
0.6798	Remote Similarity	NPD5978	Approved
0.6798	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5977	Approved
0.6793	Remote Similarity	NPD7177	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