NPASS Compound

Structure

CID214116 OpenBabel06191716002D 24 28 0 0 1 0 0 0 0 0999 V2000 -3.8866 -3.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7972 -1.3797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9203 1.2418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7218 0.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1064 0.7862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7095 -0.1678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4899 -2.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2880 -3.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3750 0.8423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0941 -0.1465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8956 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4851 -2.0025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2836 -1.5415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2908 -0.6102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0964 -2.0056 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8997 -1.5418 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6843 -1.5378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4837 -0.1559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6852 -0.6170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0865 -2.9320 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6998 -2.0095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1139 -1.9969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2920 0.7459 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 20 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 14 18 2 0 0 0 0 15 13 1 6 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 1 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	324.737
LogP:	2.031
LogD:	2.326
LogS:	-2.839
# Rotatable Bonds:	1
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.873
Synthetic Accessibility Score:	3.637
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.818
MDCK Permeability:	3.4516313462518156e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	88.12098693847656%
Volume Distribution (VD):	2.656
Pgp-substrate:	6.508467197418213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.688
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.706
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.594
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	13.732
Half-life (T1/2):	0.093

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.153
AMES Toxicity:	0.561
Rat Oral Acute Toxicity:	0.582
Maximum Recommended Daily Dose:	0.812
Skin Sensitization:	0.141
Carcinogencity:	0.403
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC214116

Natural Product ID:	NPC214116
*Common Name:**	Guatterine
IUPAC Name:	n.a.
Synonyms:	Guatterine
Standard InCHIKey:	IMMQQBXZSPYGID-HOTGVXAUSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-20-8-7-12-13-14(18-19(17(12)22-2)24-9-23-18)10-5-3-4-6-11(10)16(21)15(13)20/h3-6,15-16,21H,7-9H2,1-2H3/t15-,16-/m0/s1
SMILES:	COc1c2OCOc2c2c3c1CCN([C@@H]3[C@H](c1c2cccc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464733
PubChem CID:	10358947
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines [CHEMONTID:0003021] Hydroxy-7-aporphines

*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
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620236]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21816	Calea jamaicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25164	Polyalthia suaveolens	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24593	Campanula pyramidalis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24561	Sesuvium portulacastrum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25009	Cystoseira myrica	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24939	Veronica officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13718	Poria tenuis	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24123	Ramalina scopulorum	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12599.1	Pinus leiophylla var. chihuahuana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28729	Spirostachys africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14893	Streptomyces eurocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24723	Ophiorrhiza bracteata	Species	Rubiaceae	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
ED50	1
Others	3

Activity Type	# Activity
Cell Line	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	107000.0	nM	PMID[514738]
NPT189	Cell Line	Vero	Chlorocebus aethiops	MTC	=	62.0	uM	PMID[514738]
NPT1859	Organism	Human poliovirus 2	Human poliovirus 2	ED50	=	62.0	uM	PMID[514738]
NPT2	Others	Unspecified		Ratio	=	1.7	n.a.	PMID[514738]

☑ 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 NPC214116 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	343
0.1-0.2	1590
0.2-0.3	6728
0.3-0.4	11239
0.4-0.5	6035
0.5-0.6	11331
0.6-0.7	4412
0.7-0.8	730
0.8-0.85	211
0.85-0.9	61
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9651	High Similarity	NPC117717
0.9586	High Similarity	NPC248642
0.9583	High Similarity	NPC126284
0.9529	High Similarity	NPC156576
0.9286	High Similarity	NPC149090
0.9286	High Similarity	NPC19520
0.9133	High Similarity	NPC476575
0.9091	High Similarity	NPC82763
0.9086	High Similarity	NPC57036
0.907	High Similarity	NPC114364
0.907	High Similarity	NPC320223
0.9064	High Similarity	NPC128560
0.9064	High Similarity	NPC229166
0.9064	High Similarity	NPC199465
0.9048	High Similarity	NPC24264
0.9048	High Similarity	NPC476432
0.9034	High Similarity	NPC186546
0.9034	High Similarity	NPC476576
0.9012	High Similarity	NPC112575
0.9	High Similarity	NPC118274
0.9	High Similarity	NPC168753
0.8994	High Similarity	NPC298979
0.8994	High Similarity	NPC247389
0.8988	High Similarity	NPC167546
0.8988	High Similarity	NPC16805
0.8988	High Similarity	NPC225774
0.8988	High Similarity	NPC302527
0.8966	High Similarity	NPC474506
0.8966	High Similarity	NPC32413
0.896	High Similarity	NPC148693
0.896	High Similarity	NPC23219
0.896	High Similarity	NPC118633
0.896	High Similarity	NPC294790
0.8947	High Similarity	NPC239775
0.8935	High Similarity	NPC219341
0.8908	High Similarity	NPC258695
0.8908	High Similarity	NPC267408
0.8908	High Similarity	NPC470879
0.8895	High Similarity	NPC2314
0.8882	High Similarity	NPC210918
0.882	High Similarity	NPC237579
0.881	High Similarity	NPC160298
0.881	High Similarity	NPC232924
0.881	High Similarity	NPC266753
0.881	High Similarity	NPC306902
0.881	High Similarity	NPC477559
0.8807	High Similarity	NPC233718
0.8807	High Similarity	NPC116284
0.88	High Similarity	NPC244554
0.8772	High Similarity	NPC150879
0.8757	High Similarity	NPC135772
0.875	High Similarity	NPC312918
0.875	High Similarity	NPC476574
0.875	High Similarity	NPC155442
0.875	High Similarity	NPC477561
0.8736	High Similarity	NPC477558
0.8693	High Similarity	NPC474507
0.8686	High Similarity	NPC476577
0.8686	High Similarity	NPC173416
0.8686	High Similarity	NPC148709
0.8671	High Similarity	NPC6152
0.8663	High Similarity	NPC205421
0.8663	High Similarity	NPC117188
0.8663	High Similarity	NPC158376
0.8663	High Similarity	NPC12053
0.8663	High Similarity	NPC474931
0.8663	High Similarity	NPC81218
0.8663	High Similarity	NPC145832
0.8663	High Similarity	NPC306555
0.8655	High Similarity	NPC136508
0.8655	High Similarity	NPC212794
0.8655	High Similarity	NPC196447
0.8655	High Similarity	NPC13504
0.8655	High Similarity	NPC306843
0.8655	High Similarity	NPC96603
0.8655	High Similarity	NPC253043
0.8655	High Similarity	NPC78222
0.8655	High Similarity	NPC477563
0.8619	High Similarity	NPC475754
0.8596	High Similarity	NPC275132
0.8596	High Similarity	NPC233650
0.8596	High Similarity	NPC324144
0.858	High Similarity	NPC476572
0.8571	High Similarity	NPC99659
0.8571	High Similarity	NPC325871
0.8563	High Similarity	NPC152212
0.8555	High Similarity	NPC204947
0.8547	High Similarity	NPC134858
0.8523	High Similarity	NPC187678
0.8506	High Similarity	NPC241055
0.85	High Similarity	NPC9867
0.8497	Intermediate Similarity	NPC304659
0.8497	Intermediate Similarity	NPC86144
0.8488	Intermediate Similarity	NPC1229
0.8483	Intermediate Similarity	NPC220961
0.848	Intermediate Similarity	NPC27410
0.848	Intermediate Similarity	NPC166014
0.8457	Intermediate Similarity	NPC75958
0.8448	Intermediate Similarity	NPC210140
0.8439	Intermediate Similarity	NPC169743
0.8439	Intermediate Similarity	NPC168409
0.8409	Intermediate Similarity	NPC477640
0.8409	Intermediate Similarity	NPC470739
0.8409	Intermediate Similarity	NPC225597
0.84	Intermediate Similarity	NPC475686
0.84	Intermediate Similarity	NPC266176
0.84	Intermediate Similarity	NPC158148
0.84	Intermediate Similarity	NPC82533
0.84	Intermediate Similarity	NPC290759
0.84	Intermediate Similarity	NPC58766
0.8393	Intermediate Similarity	NPC326316
0.8393	Intermediate Similarity	NPC81733
0.8391	Intermediate Similarity	NPC13916
0.8391	Intermediate Similarity	NPC264850
0.8382	Intermediate Similarity	NPC189470
0.8372	Intermediate Similarity	NPC119649
0.8372	Intermediate Similarity	NPC235143
0.8372	Intermediate Similarity	NPC205255
0.8372	Intermediate Similarity	NPC230956
0.8372	Intermediate Similarity	NPC271388
0.837	Intermediate Similarity	NPC24260
0.837	Intermediate Similarity	NPC478093
0.8362	Intermediate Similarity	NPC477020
0.8362	Intermediate Similarity	NPC66341
0.8362	Intermediate Similarity	NPC192135
0.8352	Intermediate Similarity	NPC477562
0.8352	Intermediate Similarity	NPC474475
0.8352	Intermediate Similarity	NPC26240
0.8352	Intermediate Similarity	NPC69712
0.8343	Intermediate Similarity	NPC190332
0.8343	Intermediate Similarity	NPC181653
0.8333	Intermediate Similarity	NPC46990
0.8333	Intermediate Similarity	NPC232514
0.8333	Intermediate Similarity	NPC276944
0.8333	Intermediate Similarity	NPC24465
0.8333	Intermediate Similarity	NPC238530
0.8324	Intermediate Similarity	NPC79402
0.8324	Intermediate Similarity	NPC30182
0.8324	Intermediate Similarity	NPC473589
0.8324	Intermediate Similarity	NPC478092
0.8324	Intermediate Similarity	NPC80759
0.8324	Intermediate Similarity	NPC478091
0.8314	Intermediate Similarity	NPC221864
0.8287	Intermediate Similarity	NPC299990
0.8287	Intermediate Similarity	NPC73492
0.8286	Intermediate Similarity	NPC68328
0.828	Intermediate Similarity	NPC162653
0.8276	Intermediate Similarity	NPC320104
0.8249	Intermediate Similarity	NPC311991
0.8246	Intermediate Similarity	NPC216459
0.8246	Intermediate Similarity	NPC41178
0.8246	Intermediate Similarity	NPC138487
0.8246	Intermediate Similarity	NPC244112
0.8242	Intermediate Similarity	NPC302275
0.8239	Intermediate Similarity	NPC100566
0.8229	Intermediate Similarity	NPC180306
0.8222	Intermediate Similarity	NPC15919
0.8218	Intermediate Similarity	NPC60186
0.8214	Intermediate Similarity	NPC475959
0.8208	Intermediate Similarity	NPC111485
0.8207	Intermediate Similarity	NPC474904
0.8202	Intermediate Similarity	NPC231371
0.8198	Intermediate Similarity	NPC146288
0.8197	Intermediate Similarity	NPC16357
0.8197	Intermediate Similarity	NPC302245
0.8197	Intermediate Similarity	NPC95426
0.8192	Intermediate Similarity	NPC204908
0.8192	Intermediate Similarity	NPC83198
0.8182	Intermediate Similarity	NPC35627
0.8182	Intermediate Similarity	NPC476573
0.8182	Intermediate Similarity	NPC81247
0.8167	Intermediate Similarity	NPC474470
0.8167	Intermediate Similarity	NPC241704
0.8167	Intermediate Similarity	NPC237044
0.8152	Intermediate Similarity	NPC65312
0.8152	Intermediate Similarity	NPC139783
0.814	Intermediate Similarity	NPC123323
0.8122	Intermediate Similarity	NPC474325
0.8111	Intermediate Similarity	NPC304675
0.8111	Intermediate Similarity	NPC329969
0.8108	Intermediate Similarity	NPC22115
0.8108	Intermediate Similarity	NPC275680
0.8108	Intermediate Similarity	NPC312531
0.8107	Intermediate Similarity	NPC37144
0.8107	Intermediate Similarity	NPC59907
0.8105	Intermediate Similarity	NPC475654
0.8103	Intermediate Similarity	NPC59028
0.8103	Intermediate Similarity	NPC477080
0.8103	Intermediate Similarity	NPC92191
0.8101	Intermediate Similarity	NPC65403
0.8092	Intermediate Similarity	NPC126519
0.8092	Intermediate Similarity	NPC203784
0.8092	Intermediate Similarity	NPC170503
0.8092	Intermediate Similarity	NPC31311
0.8092	Intermediate Similarity	NPC234392
0.8079	Intermediate Similarity	NPC124657
0.8079	Intermediate Similarity	NPC56887
0.8079	Intermediate Similarity	NPC223077
0.8079	Intermediate Similarity	NPC193853
0.8077	Intermediate Similarity	NPC32154

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 NPC214116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	729
0.2-0.3	1102
0.3-0.4	2289
0.4-0.5	2609
0.5-0.6	1559
0.6-0.7	544
0.7-0.8	115
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8352	Intermediate Similarity	NPD7906	Approved
0.8297	Intermediate Similarity	NPD4663	Approved
0.8286	Intermediate Similarity	NPD3051	Approved
0.8239	Intermediate Similarity	NPD2970	Approved
0.8239	Intermediate Similarity	NPD2969	Approved
0.8232	Intermediate Similarity	NPD4577	Approved
0.8232	Intermediate Similarity	NPD4578	Approved
0.809	Intermediate Similarity	NPD27	Approved
0.809	Intermediate Similarity	NPD2489	Approved
0.7989	Intermediate Similarity	NPD8054	Approved
0.7989	Intermediate Similarity	NPD8053	Approved
0.7989	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD5241	Discontinued
0.7956	Intermediate Similarity	NPD8156	Discontinued
0.7901	Intermediate Similarity	NPD8251	Approved
0.7901	Intermediate Similarity	NPD8099	Discontinued
0.7901	Intermediate Similarity	NPD8252	Approved
0.7889	Intermediate Similarity	NPD4481	Phase 3
0.7853	Intermediate Similarity	NPD2974	Approved
0.7853	Intermediate Similarity	NPD2973	Approved
0.7853	Intermediate Similarity	NPD2975	Approved
0.7838	Intermediate Similarity	NPD7311	Approved
0.7838	Intermediate Similarity	NPD7312	Approved
0.7838	Intermediate Similarity	NPD7313	Approved
0.7838	Intermediate Similarity	NPD7310	Approved
0.7836	Intermediate Similarity	NPD4584	Approved
0.7835	Intermediate Similarity	NPD5005	Approved
0.7835	Intermediate Similarity	NPD5006	Approved
0.7798	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6788	Approved
0.7796	Intermediate Similarity	NPD7309	Approved
0.7784	Intermediate Similarity	NPD3450	Approved
0.7784	Intermediate Similarity	NPD2493	Approved
0.7784	Intermediate Similarity	NPD2494	Approved
0.7784	Intermediate Similarity	NPD3452	Approved
0.7778	Intermediate Similarity	NPD2420	Approved
0.7778	Intermediate Similarity	NPD2421	Approved
0.7778	Intermediate Similarity	NPD6071	Discontinued
0.774	Intermediate Similarity	NPD2563	Approved
0.774	Intermediate Similarity	NPD2560	Approved
0.7732	Intermediate Similarity	NPD4580	Approved
0.772	Intermediate Similarity	NPD4420	Approved
0.7719	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD2977	Approved
0.7684	Intermediate Similarity	NPD2978	Approved
0.7667	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4582	Approved
0.7665	Intermediate Similarity	NPD4583	Approved
0.7614	Intermediate Similarity	NPD4004	Approved
0.7614	Intermediate Similarity	NPD4002	Approved
0.7598	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7827	Phase 1
0.7558	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2488	Approved
0.75	Intermediate Similarity	NPD2490	Approved
0.75	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4773	Phase 2
0.7472	Intermediate Similarity	NPD4772	Phase 2
0.7463	Intermediate Similarity	NPD7047	Phase 3
0.746	Intermediate Similarity	NPD2971	Approved
0.746	Intermediate Similarity	NPD2968	Approved
0.7459	Intermediate Similarity	NPD7831	Phase 2
0.7459	Intermediate Similarity	NPD7833	Phase 2
0.7459	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4055	Discovery
0.7458	Intermediate Similarity	NPD4005	Discontinued
0.7442	Intermediate Similarity	NPD4237	Approved
0.7442	Intermediate Similarity	NPD4236	Phase 3
0.7436	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6997	Phase 2
0.7411	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2898	Approved
0.736	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5177	Phase 3
0.7306	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7213	Phase 3
0.7273	Intermediate Similarity	NPD7212	Phase 2
0.7263	Intermediate Similarity	NPD4017	Approved
0.7259	Intermediate Similarity	NPD5582	Discontinued
0.7247	Intermediate Similarity	NPD4727	Phase 1
0.7241	Intermediate Similarity	NPD3060	Approved
0.7238	Intermediate Similarity	NPD7298	Approved
0.7238	Intermediate Similarity	NPD37	Approved
0.7232	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1424	Approved
0.7232	Intermediate Similarity	NPD7447	Phase 1
0.7222	Intermediate Similarity	NPD4678	Approved
0.7222	Intermediate Similarity	NPD4675	Approved
0.7209	Intermediate Similarity	NPD1753	Discontinued
0.7204	Intermediate Similarity	NPD4010	Discontinued
0.7196	Intermediate Similarity	NPD6042	Phase 2
0.7196	Intermediate Similarity	NPD42	Phase 2
0.7189	Intermediate Similarity	NPD5677	Discontinued
0.7174	Intermediate Similarity	NPD5604	Discontinued
0.7151	Intermediate Similarity	NPD6030	Approved
0.7151	Intermediate Similarity	NPD6031	Approved
0.715	Intermediate Similarity	NPD8095	Phase 1
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7135	Intermediate Similarity	NPD7400	Phase 3
0.7135	Intermediate Similarity	NPD5709	Phase 3
0.7129	Intermediate Similarity	NPD3057	Approved
0.7123	Intermediate Similarity	NPD7907	Approved
0.712	Intermediate Similarity	NPD6297	Approved
0.712	Intermediate Similarity	NPD4966	Approved
0.712	Intermediate Similarity	NPD4965	Approved
0.712	Intermediate Similarity	NPD4967	Phase 2
0.7119	Intermediate Similarity	NPD3845	Phase 1
0.7119	Intermediate Similarity	NPD7124	Phase 2
0.7119	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6723	Discontinued
0.711	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4111	Phase 1
0.7109	Intermediate Similarity	NPD4665	Approved
0.7104	Intermediate Similarity	NPD5772	Approved
0.7104	Intermediate Similarity	NPD5773	Approved
0.7098	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4666	Phase 3
0.708	Intermediate Similarity	NPD8153	Approved
0.708	Intermediate Similarity	NPD8152	Approved
0.7076	Intermediate Similarity	NPD3109	Approved
0.7076	Intermediate Similarity	NPD3110	Approved
0.7062	Intermediate Similarity	NPD6853	Approved
0.7062	Intermediate Similarity	NPD6851	Approved
0.7059	Intermediate Similarity	NPD6107	Approved
0.7056	Intermediate Similarity	NPD3640	Phase 3
0.7056	Intermediate Similarity	NPD3641	Approved
0.7056	Intermediate Similarity	NPD3639	Approved
0.7056	Intermediate Similarity	NPD5976	Discontinued
0.7047	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6674	Discontinued
0.7044	Intermediate Similarity	NPD3533	Approved
0.7044	Intermediate Similarity	NPD2972	Approved
0.7032	Intermediate Similarity	NPD6625	Approved
0.7031	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4721	Approved
0.7029	Intermediate Similarity	NPD4725	Approved
0.7029	Intermediate Similarity	NPD4726	Approved
0.7019	Intermediate Similarity	NPD5676	Approved
0.701	Intermediate Similarity	NPD7281	Phase 3
0.701	Intermediate Similarity	NPD7280	Phase 3
0.7006	Intermediate Similarity	NPD7466	Approved
0.7	Intermediate Similarity	NPD6090	Discontinued
0.6995	Remote Similarity	NPD6072	Discontinued
0.6977	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2238	Phase 2
0.6976	Remote Similarity	NPD4040	Phase 1
0.6966	Remote Similarity	NPD5160	Discontinued
0.6963	Remote Similarity	NPD7228	Approved
0.6961	Remote Similarity	NPD3448	Approved
0.6961	Remote Similarity	NPD2491	Approved
0.6957	Remote Similarity	NPD3383	Approved
0.6957	Remote Similarity	NPD3384	Approved
0.6957	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3382	Approved
0.6954	Remote Similarity	NPD6842	Approved
0.6954	Remote Similarity	NPD6841	Approved
0.6954	Remote Similarity	NPD6843	Phase 3
0.6954	Remote Similarity	NPD2200	Suspended
0.6952	Remote Similarity	NPD6234	Discontinued
0.6946	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4107	Approved
0.6944	Remote Similarity	NPD4123	Phase 3
0.6943	Remote Similarity	NPD7007	Discovery
0.6937	Remote Similarity	NPD7048	Phase 3
0.6927	Remote Similarity	NPD6666	Approved
0.6927	Remote Similarity	NPD6667	Approved
0.6914	Remote Similarity	NPD4108	Discontinued
0.6911	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5754	Discontinued
0.6901	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5242	Approved
0.6893	Remote Similarity	NPD7037	Approved
0.6878	Remote Similarity	NPD7802	Discontinued
0.6875	Remote Similarity	NPD7701	Phase 2
0.686	Remote Similarity	NPD5718	Phase 2
0.6854	Remote Similarity	NPD4162	Approved
0.6834	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4210	Discontinued
0.6829	Remote Similarity	NPD4482	Phase 3
0.6828	Remote Similarity	NPD4585	Approved
0.6825	Remote Similarity	NPD6037	Discontinued
0.6823	Remote Similarity	NPD5938	Phase 3
0.6821	Remote Similarity	NPD4474	Approved
0.6821	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4475	Approved
0.6816	Remote Similarity	NPD7262	Phase 1
0.6811	Remote Similarity	NPD5089	Approved
0.6811	Remote Similarity	NPD5090	Approved
0.6806	Remote Similarity	NPD6688	Approved
0.6806	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6687	Approved
0.6802	Remote Similarity	NPD3027	Phase 3
0.6802	Remote Similarity	NPD5155	Approved
0.6802	Remote Similarity	NPD5156	Approved
0.68	Remote Similarity	NPD2568	Approved
0.68	Remote Similarity	NPD3808	Clinical (unspecified phase)

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