NPASS Compound

Structure

NPC3381 OpenBabel07101719522D 40 45 0 0 1 0 0 0 0 0999 V2000 7.1527 3.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 5.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3691 4.7475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6259 4.0783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 4.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7707 5.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7052 6.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4836 4.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 4.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7926 5.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 3.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8363 4.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1235 6.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4180 5.0565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.3743 5.4723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4325 7.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4399 4.8486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7270 6.0075 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 5.9190 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 17 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 6 31 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 10 2 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 30 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 15 37 1 0 0 0 0 16 33 2 0 0 0 0 16 38 1 0 0 0 0 17 20 2 0 0 0 0 18 2 1 6 0 0 0 18 21 1 0 0 0 0 19 14 1 6 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 1 0 0 0 22 30 1 1 0 0 0 23 31 1 1 0 0 0 24 18 1 6 0 0 0 24 39 1 0 0 0 0 25 31 1 0 0 0 0 25 34 2 0 0 0 0 26 32 1 1 0 0 0 26 35 1 0 0 0 0 27 32 1 1 0 0 0 27 40 1 0 0 0 0 28 36 2 0 0 0 0 28 39 1 0 0 0 0 29 37 1 0 0 0 0 29 38 1 0 0 0 0 30 5 1 1 0 0 0 31 32 1 1 0 0 0 32 40 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.3
Volume:	567.829
LogP:	4.518
LogD:	3.753
LogS:	-4.808
# Rotatable Bonds:	7
TPSA:	108.5
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.192
Synthetic Accessibility Score:	6.051
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.014
MDCK Permeability:	3.5299191949889064e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	79.77127838134766%
Volume Distribution (VD):	1.401
Pgp-substrate:	6.351837635040283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.611
CYP2C19-inhibitor:	0.363
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.864
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	13.061
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.128
Human Hepatotoxicity (H-HT):	0.338
Drug-inuced Liver Injury (DILI):	0.573
AMES Toxicity:	0.669
Rat Oral Acute Toxicity:	0.458
Maximum Recommended Daily Dose:	0.695
Skin Sensitization:	0.825
Carcinogencity:	0.907
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC3381

Natural Product ID:	NPC3381
*Common Name:**	VJBIVFCLNSFNTO-KDKZKVEXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VJBIVFCLNSFNTO-KDKZKVEXSA-N
Standard InCHI:	InChI=1S/C32H44O8/c1-17-13-24(39-28(36)20(17)15-37-29(3,4)38-16-33)18(2)21-7-8-22-19-14-27-32(40-27)26(35)10-9-25(34)31(32,6)23(19)11-12-30(21,22)5/h9-10,16,18-19,21-24,26-27,35H,7-8,11-15H2,1-6H3/t18-,19-,21+,22-,23-,24+,26-,27+,30+,31-,32+/m0/s1
SMILES:	CC1=C(COC(C)(C)OC=O)C(=O)O[C@H](C1)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H]4[C@@]5([C@H](C=CC(=O)[C@]5(C)[C@H]3CC[C@]12C)O)O4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047408
PubChem CID:	66572430
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO20281	Withania aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22705001]
NPO20281	Withania aristata	Species	Solanaceae	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	8
Others	1

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	40000.0	nM	PMID[464366]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[464366]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	37300.0	nM	PMID[464366]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	26900.0	nM	PMID[464366]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	18300.0	nM	PMID[464366]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	27800.0	nM	PMID[464366]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	18500.0	nM	PMID[464366]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	1.0	n.a.	PMID[464366]

☑ 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 NPC3381 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	246
0.1-0.2	1407
0.2-0.3	4071
0.3-0.4	8106
0.4-0.5	12530
0.5-0.6	7426
0.6-0.7	6226
0.7-0.8	2475
0.8-0.85	147
0.85-0.9	42
0.9-0.95	20
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9391	High Similarity	NPC473274
0.9386	High Similarity	NPC286528
0.9386	High Similarity	NPC20302
0.9386	High Similarity	NPC140055
0.9386	High Similarity	NPC167606
0.9339	High Similarity	NPC231240
0.9304	High Similarity	NPC50774
0.9304	High Similarity	NPC709
0.9262	High Similarity	NPC316915
0.9231	High Similarity	NPC473256
0.9231	High Similarity	NPC470878
0.9224	High Similarity	NPC264954
0.9217	High Similarity	NPC312824
0.9217	High Similarity	NPC470493
0.9217	High Similarity	NPC470492
0.9217	High Similarity	NPC183580
0.9174	High Similarity	NPC473593
0.9153	High Similarity	NPC470265
0.9153	High Similarity	NPC23786
0.9145	High Similarity	NPC474370
0.9123	High Similarity	NPC122056
0.9068	High Similarity	NPC67569
0.9043	High Similarity	NPC67259
0.9043	High Similarity	NPC147912
0.9016	High Similarity	NPC476966
0.9	High Similarity	NPC470494
0.8992	High Similarity	NPC88326
0.8992	High Similarity	NPC153700
0.8917	High Similarity	NPC469789
0.8898	High Similarity	NPC473270
0.8843	High Similarity	NPC8369
0.8843	High Similarity	NPC8374
0.8814	High Similarity	NPC186525
0.8803	High Similarity	NPC270929
0.877	High Similarity	NPC473635
0.877	High Similarity	NPC293112
0.876	High Similarity	NPC11895
0.8729	High Similarity	NPC243065
0.8699	High Similarity	NPC42399
0.8689	High Similarity	NPC81736
0.8689	High Similarity	NPC172154
0.8678	High Similarity	NPC170538
0.8655	High Similarity	NPC329736
0.8629	High Similarity	NPC245094
0.8629	High Similarity	NPC473620
0.8621	High Similarity	NPC474315
0.8583	High Similarity	NPC61520
0.856	High Similarity	NPC471407
0.8559	High Similarity	NPC284915
0.8547	High Similarity	NPC191620
0.8537	High Similarity	NPC241456
0.8537	High Similarity	NPC32868
0.8537	High Similarity	NPC318135
0.8534	High Similarity	NPC29133
0.8492	Intermediate Similarity	NPC173347
0.8487	Intermediate Similarity	NPC64318
0.8462	Intermediate Similarity	NPC470961
0.8455	Intermediate Similarity	NPC204812
0.8448	Intermediate Similarity	NPC475065
0.8443	Intermediate Similarity	NPC129434
0.8435	Intermediate Similarity	NPC91034
0.843	Intermediate Similarity	NPC475520
0.8425	Intermediate Similarity	NPC471855
0.8417	Intermediate Similarity	NPC476965
0.8417	Intermediate Similarity	NPC470959
0.84	Intermediate Similarity	NPC287423
0.84	Intermediate Similarity	NPC298841
0.839	Intermediate Similarity	NPC69291
0.8376	Intermediate Similarity	NPC37116
0.8376	Intermediate Similarity	NPC473627
0.8374	Intermediate Similarity	NPC269642
0.8362	Intermediate Similarity	NPC475418
0.8362	Intermediate Similarity	NPC473482
0.8362	Intermediate Similarity	NPC318363
0.8347	Intermediate Similarity	NPC473617
0.8347	Intermediate Similarity	NPC45475
0.8347	Intermediate Similarity	NPC257457
0.8347	Intermediate Similarity	NPC311554
0.8347	Intermediate Similarity	NPC473828
0.8333	Intermediate Similarity	NPC311534
0.8293	Intermediate Similarity	NPC476204
0.8293	Intermediate Similarity	NPC46570
0.8293	Intermediate Similarity	NPC202051
0.8293	Intermediate Similarity	NPC4021
0.8293	Intermediate Similarity	NPC159456
0.8293	Intermediate Similarity	NPC170084
0.8279	Intermediate Similarity	NPC232258
0.8279	Intermediate Similarity	NPC477071
0.8279	Intermediate Similarity	NPC476960
0.8279	Intermediate Similarity	NPC475834
0.8279	Intermediate Similarity	NPC474179
0.8276	Intermediate Similarity	NPC473284
0.8276	Intermediate Similarity	NPC329048
0.8276	Intermediate Similarity	NPC330011
0.8264	Intermediate Similarity	NPC471854
0.8254	Intermediate Similarity	NPC156797
0.825	Intermediate Similarity	NPC220293
0.8235	Intermediate Similarity	NPC236217
0.8226	Intermediate Similarity	NPC107493
0.8211	Intermediate Similarity	NPC476961
0.8211	Intermediate Similarity	NPC251226
0.8211	Intermediate Similarity	NPC48692
0.8211	Intermediate Similarity	NPC268530
0.8211	Intermediate Similarity	NPC154491
0.8211	Intermediate Similarity	NPC470312
0.8203	Intermediate Similarity	NPC196921
0.8203	Intermediate Similarity	NPC220757
0.8197	Intermediate Similarity	NPC475913
0.8197	Intermediate Similarity	NPC473720
0.8197	Intermediate Similarity	NPC291564
0.8197	Intermediate Similarity	NPC239293
0.8182	Intermediate Similarity	NPC470075
0.816	Intermediate Similarity	NPC41129
0.816	Intermediate Similarity	NPC120724
0.8151	Intermediate Similarity	NPC470960
0.8145	Intermediate Similarity	NPC204731
0.814	Intermediate Similarity	NPC473679
0.814	Intermediate Similarity	NPC322904
0.814	Intermediate Similarity	NPC183816
0.814	Intermediate Similarity	NPC324933
0.814	Intermediate Similarity	NPC319719
0.814	Intermediate Similarity	NPC196874
0.814	Intermediate Similarity	NPC233223
0.814	Intermediate Similarity	NPC475177
0.814	Intermediate Similarity	NPC475444
0.8136	Intermediate Similarity	NPC284828
0.8136	Intermediate Similarity	NPC472216
0.8136	Intermediate Similarity	NPC173905
0.8136	Intermediate Similarity	NPC5475
0.813	Intermediate Similarity	NPC475041
0.813	Intermediate Similarity	NPC42673
0.8125	Intermediate Similarity	NPC35109
0.8125	Intermediate Similarity	NPC231529
0.8125	Intermediate Similarity	NPC470880
0.8115	Intermediate Similarity	NPC239273
0.8115	Intermediate Similarity	NPC55296
0.8115	Intermediate Similarity	NPC474483
0.811	Intermediate Similarity	NPC473253
0.8099	Intermediate Similarity	NPC74727
0.8099	Intermediate Similarity	NPC475163
0.8095	Intermediate Similarity	NPC470922
0.8092	Intermediate Similarity	NPC158350
0.8083	Intermediate Similarity	NPC476163
0.8083	Intermediate Similarity	NPC100267
0.8083	Intermediate Similarity	NPC475524
0.808	Intermediate Similarity	NPC28532
0.8077	Intermediate Similarity	NPC469673
0.8065	Intermediate Similarity	NPC241192
0.8065	Intermediate Similarity	NPC281840
0.8065	Intermediate Similarity	NPC476150
0.8065	Intermediate Similarity	NPC476127
0.8065	Intermediate Similarity	NPC476962
0.8062	Intermediate Similarity	NPC222951
0.8062	Intermediate Similarity	NPC43589
0.8062	Intermediate Similarity	NPC311178
0.8062	Intermediate Similarity	NPC300655
0.8051	Intermediate Similarity	NPC220155
0.8049	Intermediate Similarity	NPC234522
0.8047	Intermediate Similarity	NPC472269
0.8047	Intermediate Similarity	NPC112492
0.8047	Intermediate Similarity	NPC23020
0.8047	Intermediate Similarity	NPC472268
0.8047	Intermediate Similarity	NPC472270
0.8045	Intermediate Similarity	NPC75616
0.8033	Intermediate Similarity	NPC207637
0.8033	Intermediate Similarity	NPC44170
0.8033	Intermediate Similarity	NPC148458
0.8033	Intermediate Similarity	NPC268954
0.8031	Intermediate Similarity	NPC174367
0.8031	Intermediate Similarity	NPC203702
0.8031	Intermediate Similarity	NPC120994
0.8031	Intermediate Similarity	NPC47113
0.803	Intermediate Similarity	NPC289700
0.803	Intermediate Similarity	NPC62172
0.8017	Intermediate Similarity	NPC255017
0.8017	Intermediate Similarity	NPC473283
0.8017	Intermediate Similarity	NPC329345
0.8017	Intermediate Similarity	NPC475050
0.8017	Intermediate Similarity	NPC264153
0.8017	Intermediate Similarity	NPC475526
0.8017	Intermediate Similarity	NPC72151
0.8017	Intermediate Similarity	NPC25909
0.8016	Intermediate Similarity	NPC6193
0.8015	Intermediate Similarity	NPC476823
0.8	Intermediate Similarity	NPC470418
0.8	Intermediate Similarity	NPC34963
0.8	Intermediate Similarity	NPC476897
0.8	Intermediate Similarity	NPC155529
0.7984	Intermediate Similarity	NPC5292
0.7984	Intermediate Similarity	NPC70542
0.7984	Intermediate Similarity	NPC10823
0.7984	Intermediate Similarity	NPC473636
0.7984	Intermediate Similarity	NPC469751
0.7984	Intermediate Similarity	NPC230513
0.7984	Intermediate Similarity	NPC471360
0.7984	Intermediate Similarity	NPC471358
0.7984	Intermediate Similarity	NPC471352
0.7984	Intermediate Similarity	NPC469755
0.7984	Intermediate Similarity	NPC471361
0.7984	Intermediate Similarity	NPC180079

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 NPC3381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1570
0.2-0.3	3622
0.3-0.4	2472
0.4-0.5	739
0.5-0.6	269
0.6-0.7	179
0.7-0.8	76
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9386	High Similarity	NPD7115	Discovery
0.7984	Intermediate Similarity	NPD7319	Approved
0.7891	Intermediate Similarity	NPD7507	Approved
0.7826	Intermediate Similarity	NPD4225	Approved
0.7787	Intermediate Similarity	NPD6882	Approved
0.7787	Intermediate Similarity	NPD8297	Approved
0.7769	Intermediate Similarity	NPD7736	Approved
0.7717	Intermediate Similarity	NPD7503	Approved
0.7603	Intermediate Similarity	NPD6686	Approved
0.7578	Intermediate Similarity	NPD8513	Phase 3
0.7578	Intermediate Similarity	NPD8033	Approved
0.7561	Intermediate Similarity	NPD6649	Approved
0.7561	Intermediate Similarity	NPD6650	Approved
0.7538	Intermediate Similarity	NPD7492	Approved
0.7519	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD8294	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD8377	Approved
0.7481	Intermediate Similarity	NPD6616	Approved
0.748	Intermediate Similarity	NPD7328	Approved
0.748	Intermediate Similarity	NPD7327	Approved
0.7462	Intermediate Similarity	NPD8328	Phase 3
0.7459	Intermediate Similarity	NPD6899	Approved
0.7459	Intermediate Similarity	NPD6881	Approved
0.7442	Intermediate Similarity	NPD8517	Approved
0.7442	Intermediate Similarity	NPD8380	Approved
0.7442	Intermediate Similarity	NPD8335	Approved
0.7442	Intermediate Similarity	NPD8516	Approved
0.7442	Intermediate Similarity	NPD8515	Approved
0.7442	Intermediate Similarity	NPD8379	Approved
0.7442	Intermediate Similarity	NPD8296	Approved
0.7442	Intermediate Similarity	NPD8378	Approved
0.7424	Intermediate Similarity	NPD7078	Approved
0.7424	Intermediate Similarity	NPD8293	Discontinued
0.7422	Intermediate Similarity	NPD7516	Approved
0.7419	Intermediate Similarity	NPD8130	Phase 1
0.7398	Intermediate Similarity	NPD6372	Approved
0.7398	Intermediate Similarity	NPD6373	Approved
0.7377	Intermediate Similarity	NPD5697	Approved
0.7377	Intermediate Similarity	NPD6412	Phase 2
0.7339	Intermediate Similarity	NPD7290	Approved
0.7339	Intermediate Similarity	NPD7102	Approved
0.7339	Intermediate Similarity	NPD6883	Approved
0.7311	Intermediate Similarity	NPD7639	Approved
0.7311	Intermediate Similarity	NPD7640	Approved
0.7308	Intermediate Similarity	NPD6016	Approved
0.7308	Intermediate Similarity	NPD6015	Approved
0.7302	Intermediate Similarity	NPD8133	Approved
0.7295	Intermediate Similarity	NPD5739	Approved
0.7295	Intermediate Similarity	NPD6675	Approved
0.7295	Intermediate Similarity	NPD6402	Approved
0.7295	Intermediate Similarity	NPD7128	Approved
0.728	Intermediate Similarity	NPD6869	Approved
0.728	Intermediate Similarity	NPD6617	Approved
0.728	Intermediate Similarity	NPD6847	Approved
0.7266	Intermediate Similarity	NPD6009	Approved
0.7258	Intermediate Similarity	NPD6013	Approved
0.7258	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6012	Approved
0.7258	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6014	Approved
0.7252	Intermediate Similarity	NPD5988	Approved
0.7241	Intermediate Similarity	NPD6399	Phase 3
0.7231	Intermediate Similarity	NPD6059	Approved
0.7227	Intermediate Similarity	NPD7638	Approved
0.72	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5211	Phase 2
0.7179	Intermediate Similarity	NPD7748	Approved
0.7177	Intermediate Similarity	NPD7320	Approved
0.7177	Intermediate Similarity	NPD6011	Approved
0.7165	Intermediate Similarity	NPD4632	Approved
0.7155	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD7902	Approved
0.7132	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5701	Approved
0.7073	Intermediate Similarity	NPD5141	Approved
0.7069	Intermediate Similarity	NPD5785	Approved
0.7063	Intermediate Similarity	NPD6371	Approved
0.7063	Intermediate Similarity	NPD4634	Approved
0.7025	Intermediate Similarity	NPD5285	Approved
0.7025	Intermediate Similarity	NPD5286	Approved
0.7025	Intermediate Similarity	NPD4696	Approved
0.7018	Intermediate Similarity	NPD3618	Phase 1
0.7016	Intermediate Similarity	NPD6008	Approved
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7008	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5328	Approved
0.6975	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5696	Approved
0.694	Remote Similarity	NPD7604	Phase 2
0.6917	Remote Similarity	NPD4697	Phase 3
0.6917	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5221	Approved
0.6917	Remote Similarity	NPD5222	Approved
0.6912	Remote Similarity	NPD8074	Phase 3
0.6911	Remote Similarity	NPD5224	Approved
0.6911	Remote Similarity	NPD5225	Approved
0.6911	Remote Similarity	NPD5226	Approved
0.6911	Remote Similarity	NPD4633	Approved
0.6905	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7101	Approved
0.6894	Remote Similarity	NPD7100	Approved
0.6891	Remote Similarity	NPD7900	Approved
0.6891	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8034	Phase 2
0.6864	Remote Similarity	NPD8035	Phase 2
0.686	Remote Similarity	NPD4755	Approved
0.686	Remote Similarity	NPD5173	Approved
0.6855	Remote Similarity	NPD5175	Approved
0.6855	Remote Similarity	NPD5174	Approved
0.6842	Remote Similarity	NPD4786	Approved
0.6833	Remote Similarity	NPD4629	Approved
0.6833	Remote Similarity	NPD5695	Phase 3
0.6833	Remote Similarity	NPD5210	Approved
0.6829	Remote Similarity	NPD5223	Approved
0.6829	Remote Similarity	NPD5344	Discontinued
0.6818	Remote Similarity	NPD6335	Approved
0.6807	Remote Similarity	NPD4202	Approved
0.6794	Remote Similarity	NPD6868	Approved
0.6794	Remote Similarity	NPD6274	Approved
0.6791	Remote Similarity	NPD5983	Phase 2
0.6783	Remote Similarity	NPD1694	Approved
0.6774	Remote Similarity	NPD7632	Discontinued
0.6772	Remote Similarity	NPD4730	Approved
0.6772	Remote Similarity	NPD4729	Approved
0.6752	Remote Similarity	NPD6672	Approved
0.6752	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5737	Approved
0.6748	Remote Similarity	NPD4700	Approved
0.6742	Remote Similarity	NPD6317	Approved
0.6739	Remote Similarity	NPD6033	Approved
0.6724	Remote Similarity	NPD7334	Approved
0.6724	Remote Similarity	NPD6684	Approved
0.6724	Remote Similarity	NPD6409	Approved
0.6724	Remote Similarity	NPD7521	Approved
0.6724	Remote Similarity	NPD5330	Approved
0.6724	Remote Similarity	NPD7146	Approved
0.6723	Remote Similarity	NPD7637	Suspended
0.6723	Remote Similarity	NPD5693	Phase 1
0.6715	Remote Similarity	NPD6336	Discontinued
0.6695	Remote Similarity	NPD4753	Phase 2
0.6693	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6053	Discontinued
0.6692	Remote Similarity	NPD6313	Approved
0.6692	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD3573	Approved
0.6639	Remote Similarity	NPD6698	Approved
0.6639	Remote Similarity	NPD46	Approved
0.6638	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5363	Approved
0.6614	Remote Similarity	NPD4767	Approved
0.6614	Remote Similarity	NPD4768	Approved
0.6612	Remote Similarity	NPD6001	Approved
0.661	Remote Similarity	NPD6903	Approved
0.6583	Remote Similarity	NPD6411	Approved
0.6583	Remote Similarity	NPD5281	Approved
0.6583	Remote Similarity	NPD5284	Approved
0.6569	Remote Similarity	NPD6067	Discontinued
0.6557	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6904	Approved
0.6555	Remote Similarity	NPD6673	Approved
0.6555	Remote Similarity	NPD6080	Approved
0.6552	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3665	Phase 1
0.6552	Remote Similarity	NPD3666	Approved
0.6552	Remote Similarity	NPD3133	Approved
0.6544	Remote Similarity	NPD6908	Approved
0.6544	Remote Similarity	NPD6909	Approved
0.6529	Remote Similarity	NPD5778	Approved
0.6529	Remote Similarity	NPD5779	Approved
0.6525	Remote Similarity	NPD5956	Approved
0.6524	Remote Similarity	NPD7799	Discontinued
0.6522	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5128	Approved
0.65	Remote Similarity	NPD7838	Discovery
0.6489	Remote Similarity	NPD5216	Approved
0.6489	Remote Similarity	NPD5217	Approved
0.6489	Remote Similarity	NPD5215	Approved
0.648	Remote Similarity	NPD6648	Approved
0.6479	Remote Similarity	NPD7260	Phase 2
0.6457	Remote Similarity	NPD4754	Approved
0.6449	Remote Similarity	NPD7642	Approved
0.6423	Remote Similarity	NPD6921	Approved
0.6417	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6101	Approved
0.6417	Remote Similarity	NPD6051	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