NPASS Compound

Structure

NPC20216 OpenBabel07101719252D 32 34 0 0 0 0 0 0 0 0999 V2000 1.3017 -4.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6928 -4.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8650 0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4255 -0.6768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8678 -3.6039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -2.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -3.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 1.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9944 -1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 2.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -3.4010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -1.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 3.0990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 3.0990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 1.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 -1.5777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 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 6 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 30 1 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 7 19 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 18 30 1 0 0 0 0 19 27 2 0 0 0 0 19 28 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 32 1 0 0 0 0 22 31 1 0 0 0 0 23 31 1 0 0 0 0 24 29 2 0 0 0 0 24 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.15
Volume:	441.948
LogP:	4.363
LogD:	2.522
LogS:	-4.062
# Rotatable Bonds:	5
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	3.494
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.844
MDCK Permeability:	1.4412603377422784e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.451
Human Intestinal Absorption (HIA):	0.128
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	95.9304428100586%
Volume Distribution (VD):	0.519
Pgp-substrate:	7.783052921295166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.16
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.759
CYP2C9-substrate:	0.168
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	2.616
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.79
AMES Toxicity:	0.135
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.804
Carcinogencity:	0.445
Eye Corrosion:	0.003
Eye Irritation:	0.259
Respiratory Toxicity:	0.762

Download Data

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

Natural Product: NPC20216

Natural Product ID:	NPC20216
*Common Name:**	Auranticin A
IUPAC Name:	(E)-3-[1-[(E)-but-2-en-2-yl]-9-hydroxy-10-(hydroxymethyl)-3-methoxy-4-methyl-6-oxobenzo[b][1,4]benzodioxepin-7-yl]but-2-enoic acid
Synonyms:
Standard InCHIKey:	NTOXIMPFEPXTTB-GNXRPPCSSA-N
Standard InCHI:	InChI=1S/C24H24O8/c1-6-11(2)15-9-18(30-5)13(4)21-23(15)31-22-16(10-25)17(26)8-14(12(3)7-19(27)28)20(22)24(29)32-21/h6-9,25-26H,10H2,1-5H3,(H,27,28)/p-1/b11-6+,12-7+
SMILES:	C/C=C(C)/c1cc(c(C)c2c1Oc1c(CO)c(cc(/C(=C/C(=O)O)/C)c1C(=O)O2)[O-])OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472092
PubChem CID:	6439369
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO23973	Preussia aurantiaca	Species	Tettigoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1904475]
NPO23973	Preussia aurantiaca	Species	Tettigoniidae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[502444]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	5.0	ug.mL-1	PMID[502444]

☑ 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 NPC20216 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	388
0.1-0.2	1686
0.2-0.3	3977
0.3-0.4	9359
0.4-0.5	8955
0.5-0.6	3526
0.6-0.7	5051
0.7-0.8	6546
0.8-0.85	2598
0.85-0.9	536
0.9-0.95	60
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC112981
0.9872	High Similarity	NPC156082
0.9811	High Similarity	NPC17219
0.9688	High Similarity	NPC246716
0.9686	High Similarity	NPC292788
0.9686	High Similarity	NPC272485
0.9625	High Similarity	NPC26568
0.9568	High Similarity	NPC181523
0.9565	High Similarity	NPC1827
0.9565	High Similarity	NPC10576
0.9565	High Similarity	NPC239440
0.9565	High Similarity	NPC20543
0.9509	High Similarity	NPC139350
0.9423	High Similarity	NPC471800
0.939	High Similarity	NPC289147
0.9383	High Similarity	NPC99613
0.9383	High Similarity	NPC49487
0.9375	High Similarity	NPC474350
0.9375	High Similarity	NPC300984
0.9367	High Similarity	NPC238381
0.9367	High Similarity	NPC168616
0.9367	High Similarity	NPC83763
0.9337	High Similarity	NPC329161
0.9337	High Similarity	NPC240887
0.9337	High Similarity	NPC113446
0.9337	High Similarity	NPC470091
0.9325	High Similarity	NPC124470
0.9325	High Similarity	NPC109827
0.9317	High Similarity	NPC267153
0.9313	High Similarity	NPC93739
0.9295	High Similarity	NPC273483
0.9268	High Similarity	NPC158226
0.9259	High Similarity	NPC29160
0.9255	High Similarity	NPC284007
0.925	High Similarity	NPC303565
0.9202	High Similarity	NPC234331
0.9198	High Similarity	NPC8070
0.9187	High Similarity	NPC143050
0.9146	High Similarity	NPC165979
0.9146	High Similarity	NPC163130
0.9136	High Similarity	NPC197168
0.9136	High Similarity	NPC234004
0.913	High Similarity	NPC66288
0.9119	High Similarity	NPC54928
0.9119	High Similarity	NPC472456
0.9108	High Similarity	NPC133856
0.9103	High Similarity	NPC291049
0.9103	High Similarity	NPC233267
0.908	High Similarity	NPC25361
0.9074	High Similarity	NPC108767
0.9074	High Similarity	NPC8300
0.9068	High Similarity	NPC475886
0.9068	High Similarity	NPC200594
0.9068	High Similarity	NPC47623
0.9068	High Similarity	NPC474287
0.9062	High Similarity	NPC165977
0.9062	High Similarity	NPC217677
0.9057	High Similarity	NPC149618
0.9057	High Similarity	NPC89625
0.9051	High Similarity	NPC289968
0.9038	High Similarity	NPC105415
0.9024	High Similarity	NPC472452
0.9018	High Similarity	NPC270837
0.9018	High Similarity	NPC7483
0.9018	High Similarity	NPC236132
0.9012	High Similarity	NPC474187
0.9012	High Similarity	NPC475883
0.9012	High Similarity	NPC474186
0.9012	High Similarity	NPC474351
0.9006	High Similarity	NPC45846
0.9	High Similarity	NPC146211
0.8994	High Similarity	NPC475895
0.897	High Similarity	NPC474024
0.8963	High Similarity	NPC85057
0.8963	High Similarity	NPC130920
0.8957	High Similarity	NPC294965
0.8957	High Similarity	NPC144843
0.8951	High Similarity	NPC56085
0.8951	High Similarity	NPC14353
0.8951	High Similarity	NPC228785
0.8931	High Similarity	NPC199773
0.8924	High Similarity	NPC225129
0.8924	High Similarity	NPC213382
0.8924	High Similarity	NPC164527
0.8896	High Similarity	NPC40491
0.8896	High Similarity	NPC278052
0.8896	High Similarity	NPC349525
0.8896	High Similarity	NPC103201
0.8896	High Similarity	NPC61010
0.8896	High Similarity	NPC473106
0.8889	High Similarity	NPC85121
0.8889	High Similarity	NPC100123
0.8868	High Similarity	NPC204350
0.8861	High Similarity	NPC285527
0.8861	High Similarity	NPC106334
0.8855	High Similarity	NPC6588
0.8855	High Similarity	NPC477154
0.8855	High Similarity	NPC117854
0.8848	High Similarity	NPC326520
0.8846	High Similarity	NPC134621
0.8841	High Similarity	NPC229632
0.8834	High Similarity	NPC320359
0.8834	High Similarity	NPC36217
0.8834	High Similarity	NPC119224
0.8834	High Similarity	NPC292415
0.8834	High Similarity	NPC299436
0.8827	High Similarity	NPC300727
0.8827	High Similarity	NPC241904
0.8827	High Similarity	NPC108456
0.8827	High Similarity	NPC223787
0.882	High Similarity	NPC82592
0.882	High Similarity	NPC16082
0.882	High Similarity	NPC20541
0.8817	High Similarity	NPC470454
0.8817	High Similarity	NPC199533
0.8812	High Similarity	NPC175978
0.8812	High Similarity	NPC217447
0.881	High Similarity	NPC475669
0.8795	High Similarity	NPC37870
0.8795	High Similarity	NPC43319
0.8795	High Similarity	NPC30027
0.8795	High Similarity	NPC272502
0.8795	High Similarity	NPC170245
0.879	High Similarity	NPC163846
0.879	High Similarity	NPC225173
0.879	High Similarity	NPC237208
0.8788	High Similarity	NPC477689
0.8788	High Similarity	NPC41301
0.8788	High Similarity	NPC152659
0.8788	High Similarity	NPC474240
0.8788	High Similarity	NPC220313
0.8788	High Similarity	NPC236521
0.8788	High Similarity	NPC248638
0.8788	High Similarity	NPC470459
0.8782	High Similarity	NPC66404
0.8782	High Similarity	NPC95123
0.878	High Similarity	NPC266314
0.8773	High Similarity	NPC329091
0.8773	High Similarity	NPC476242
0.8765	High Similarity	NPC274730
0.8765	High Similarity	NPC227062
0.8765	High Similarity	NPC142339
0.8758	High Similarity	NPC280937
0.8758	High Similarity	NPC281477
0.8758	High Similarity	NPC298802
0.8758	High Similarity	NPC135522
0.875	High Similarity	NPC298778
0.8743	High Similarity	NPC218226
0.8742	High Similarity	NPC328119
0.8735	High Similarity	NPC475888
0.8735	High Similarity	NPC275780
0.8735	High Similarity	NPC303174
0.8735	High Similarity	NPC239752
0.8735	High Similarity	NPC470457
0.8735	High Similarity	NPC472450
0.8734	High Similarity	NPC125801
0.8727	High Similarity	NPC201800
0.8727	High Similarity	NPC52204
0.8727	High Similarity	NPC211107
0.8727	High Similarity	NPC470694
0.8727	High Similarity	NPC25152
0.8726	High Similarity	NPC29577
0.872	High Similarity	NPC470326
0.872	High Similarity	NPC84571
0.872	High Similarity	NPC321399
0.872	High Similarity	NPC472630
0.872	High Similarity	NPC472631
0.872	High Similarity	NPC472055
0.8713	High Similarity	NPC207467
0.8712	High Similarity	NPC36852
0.8712	High Similarity	NPC84935
0.8712	High Similarity	NPC78103
0.8712	High Similarity	NPC236796
0.8712	High Similarity	NPC472598
0.8712	High Similarity	NPC469584
0.8712	High Similarity	NPC474055
0.8712	High Similarity	NPC78225
0.8712	High Similarity	NPC476981
0.8712	High Similarity	NPC190020
0.8712	High Similarity	NPC181960
0.8712	High Similarity	NPC77679
0.8712	High Similarity	NPC262286
0.8704	High Similarity	NPC226025
0.8704	High Similarity	NPC470327
0.8704	High Similarity	NPC37392
0.8704	High Similarity	NPC477503
0.8704	High Similarity	NPC286052
0.8704	High Similarity	NPC472909
0.8704	High Similarity	NPC45849
0.8704	High Similarity	NPC200761
0.8701	High Similarity	NPC214901
0.8698	High Similarity	NPC260263
0.8696	High Similarity	NPC471982
0.8696	High Similarity	NPC475116
0.869	High Similarity	NPC476637
0.869	High Similarity	NPC476279
0.869	High Similarity	NPC188079
0.8688	High Similarity	NPC202595
0.8688	High Similarity	NPC119929
0.8688	High Similarity	NPC60413

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 NPC20216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	991
0.2-0.3	1911
0.3-0.4	2596
0.4-0.5	1716
0.5-0.6	969
0.6-0.7	427
0.7-0.8	160
0.8-0.85	25
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.903	High Similarity	NPD5844	Phase 1
0.8957	High Similarity	NPD6232	Discontinued
0.8795	High Similarity	NPD7473	Discontinued
0.8528	High Similarity	NPD2801	Approved
0.8528	High Similarity	NPD2393	Clinical (unspecified phase)
0.8528	High Similarity	NPD7819	Suspended
0.8491	Intermediate Similarity	NPD2532	Approved
0.8491	Intermediate Similarity	NPD2533	Approved
0.8491	Intermediate Similarity	NPD2534	Approved
0.8476	Intermediate Similarity	NPD3817	Phase 2
0.8466	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD1465	Phase 2
0.8294	Intermediate Similarity	NPD6166	Phase 2
0.8294	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5494	Approved
0.8263	Intermediate Similarity	NPD7075	Discontinued
0.8228	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD7074	Phase 3
0.8204	Intermediate Similarity	NPD3882	Suspended
0.8198	Intermediate Similarity	NPD3818	Discontinued
0.815	Intermediate Similarity	NPD7054	Approved
0.8148	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6801	Discontinued
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.8121	Intermediate Similarity	NPD4380	Phase 2
0.8103	Intermediate Similarity	NPD7472	Approved
0.8101	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD2935	Discontinued
0.8086	Intermediate Similarity	NPD1511	Approved
0.8084	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8061	Intermediate Similarity	NPD3226	Approved
0.8024	Intermediate Similarity	NPD37	Approved
0.8011	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD919	Approved
0.7988	Intermediate Similarity	NPD4967	Phase 2
0.7988	Intermediate Similarity	NPD4966	Approved
0.7988	Intermediate Similarity	NPD1512	Approved
0.7988	Intermediate Similarity	NPD4965	Approved
0.7975	Intermediate Similarity	NPD6799	Approved
0.7966	Intermediate Similarity	NPD7808	Phase 3
0.7955	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6797	Phase 2
0.7941	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD5402	Approved
0.7912	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7251	Discontinued
0.7907	Intermediate Similarity	NPD7199	Phase 2
0.7901	Intermediate Similarity	NPD4628	Phase 3
0.7895	Intermediate Similarity	NPD6234	Discontinued
0.7882	Intermediate Similarity	NPD7768	Phase 2
0.7875	Intermediate Similarity	NPD1551	Phase 2
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD5710	Approved
0.7861	Intermediate Similarity	NPD5711	Approved
0.7841	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1247	Approved
0.7799	Intermediate Similarity	NPD1607	Approved
0.7791	Intermediate Similarity	NPD3750	Approved
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7736	Intermediate Similarity	NPD447	Suspended
0.7733	Intermediate Similarity	NPD3749	Approved
0.7716	Intermediate Similarity	NPD2346	Discontinued
0.7714	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1510	Phase 2
0.7702	Intermediate Similarity	NPD2799	Discontinued
0.7684	Intermediate Similarity	NPD7228	Approved
0.7673	Intermediate Similarity	NPD1240	Approved
0.7658	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2796	Approved
0.7651	Intermediate Similarity	NPD7390	Discontinued
0.7625	Intermediate Similarity	NPD230	Phase 1
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7622	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2800	Approved
0.7622	Intermediate Similarity	NPD1243	Approved
0.7619	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD920	Approved
0.7614	Intermediate Similarity	NPD3926	Phase 2
0.7593	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7783	Phase 2
0.7576	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1653	Approved
0.7556	Intermediate Similarity	NPD5953	Discontinued
0.7547	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7485	Intermediate Similarity	NPD3748	Approved
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7286	Phase 2
0.744	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6100	Approved
0.7439	Intermediate Similarity	NPD6099	Approved
0.7435	Intermediate Similarity	NPD6779	Approved
0.7435	Intermediate Similarity	NPD6780	Approved
0.7435	Intermediate Similarity	NPD6781	Approved
0.7435	Intermediate Similarity	NPD6777	Approved
0.7435	Intermediate Similarity	NPD6782	Approved
0.7435	Intermediate Similarity	NPD6778	Approved
0.7435	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD6832	Phase 2
0.7405	Intermediate Similarity	NPD8434	Phase 2
0.7401	Intermediate Similarity	NPD8127	Discontinued
0.7396	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3027	Phase 3
0.7362	Intermediate Similarity	NPD6651	Approved
0.736	Intermediate Similarity	NPD7229	Phase 3
0.7346	Intermediate Similarity	NPD1613	Approved
0.7346	Intermediate Similarity	NPD943	Approved
0.7346	Intermediate Similarity	NPD4060	Phase 1
0.7346	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1203	Approved
0.7333	Intermediate Similarity	NPD5405	Approved
0.7333	Intermediate Similarity	NPD5406	Approved
0.7333	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD5404	Approved
0.7322	Intermediate Similarity	NPD7240	Approved
0.7321	Intermediate Similarity	NPD6190	Approved
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7698	Approved
0.7318	Intermediate Similarity	NPD5242	Approved
0.7301	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1933	Approved
0.7293	Intermediate Similarity	NPD3751	Discontinued
0.7283	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7870	Phase 2
0.7282	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7874	Approved
0.7267	Intermediate Similarity	NPD4625	Phase 3
0.7263	Intermediate Similarity	NPD3787	Discontinued
0.7251	Intermediate Similarity	NPD6273	Approved
0.7251	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4476	Approved
0.7229	Intermediate Similarity	NPD2438	Suspended
0.7229	Intermediate Similarity	NPD4477	Approved
0.7225	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD411	Approved
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7205	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7177	Discontinued
0.7188	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6823	Phase 2
0.7173	Intermediate Similarity	NPD6534	Approved
0.7173	Intermediate Similarity	NPD6535	Approved
0.7172	Intermediate Similarity	NPD7701	Phase 2
0.717	Intermediate Similarity	NPD1283	Approved
0.7169	Intermediate Similarity	NPD7033	Discontinued
0.7169	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD7003	Approved
0.7152	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD1608	Approved
0.7135	Intermediate Similarity	NPD7038	Approved
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD7039	Approved
0.7134	Intermediate Similarity	NPD2979	Phase 3
0.7125	Intermediate Similarity	NPD2797	Approved
0.7119	Intermediate Similarity	NPD5353	Approved
0.7117	Intermediate Similarity	NPD3268	Approved
0.7117	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7097	Intermediate Similarity	NPD7549	Discontinued
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1611	Approved
0.7089	Intermediate Similarity	NPD422	Phase 1
0.7083	Intermediate Similarity	NPD2344	Approved
0.707	Intermediate Similarity	NPD4626	Approved
0.7065	Intermediate Similarity	NPD7801	Approved
0.7062	Intermediate Similarity	NPD7699	Phase 2
0.7062	Intermediate Similarity	NPD7700	Phase 2
0.7062	Intermediate Similarity	NPD8455	Phase 2
0.7059	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6386	Approved
0.7045	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6385	Approved
0.7022	Intermediate Similarity	NPD4288	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