NPASS Compound

Structure

CID110701 OpenBabel06191715462D 28 30 0 0 1 0 0 0 0 0999 V2000 -3.0029 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0733 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0514 -0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 6 1 0 0 0 0 3 9 1 0 0 0 0 4 18 1 0 0 0 0 5 7 2 0 0 0 0 5 26 1 0 0 0 0 6 1 1 1 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 7 17 1 0 0 0 0 8 4 1 6 0 0 0 8 11 1 0 0 0 0 8 27 1 0 0 0 0 9 17 1 6 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 1 0 0 0 11 12 1 0 0 0 0 11 20 1 1 0 0 0 12 13 1 0 0 0 0 12 21 1 6 0 0 0 13 16 1 0 0 0 0 13 22 1 1 0 0 0 14 23 2 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 15 28 1 6 0 0 0 16 27 1 0 0 0 0 16 28 1 6 0 0 0 17 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.15
Volume:	368.338
LogP:	-0.596
LogD:	-0.378
LogS:	-1.764
# Rotatable Bonds:	5
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	4.922
Fsp3:	0.824
Lipinski Rule-of-5:	Rejected
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:	-6.242
MDCK Permeability:	0.00015155253640841693
Pgp-inhibitor:	0.001
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	23.81612777709961%
Volume Distribution (VD):	0.369
Pgp-substrate:	50.37562942504883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.568
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	1.224
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.664
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.212
Carcinogencity:	0.131
Eye Corrosion:	0.003
Eye Irritation:	0.09
Respiratory Toxicity:	0.492

Download Data

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

Natural Product: NPC110701

Natural Product ID:	NPC110701
*Common Name:**	MLTZHVBDDNOQNM-SUXXVOEXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MLTZHVBDDNOQNM-SUXXVOEXSA-N
Standard InCHI:	InChI=1S/C17H26O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8-13,15-16,18-22,24H,3-4H2,1-2H3/t6-,8-,9-,10+,11-,12+,13-,15+,16+,17-/m1/s1
SMILES:	C[C@@H]1C[C@H]([C@@]2(C(=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622812
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO17761	Ophiorrhiza japonica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17761	Ophiorrhiza japonica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27644	Machaerocereus eruca	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28518	Solanum wendlandii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25748	Eugenia grandis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28080	Pedicularis palustris	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17761	Ophiorrhiza japonica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28896	Astragalus centralpinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29280	Argopsis megalospora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27798	Verticillium intertextum	Species	Plectosphaerellaceae	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
Others	6

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	33.2	%	PMID[565951]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	33.4	%	PMID[565951]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	51.7	%	PMID[565951]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<=	30.0	%	PMID[565951]

☑ 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 NPC110701 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	255
0.1-0.2	1637
0.2-0.3	5515
0.3-0.4	9397
0.4-0.5	12698
0.5-0.6	7758
0.6-0.7	4909
0.7-0.8	476
0.8-0.85	29
0.85-0.9	8
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9406	High Similarity	NPC170432
0.94	High Similarity	NPC475928
0.9314	High Similarity	NPC148270
0.9314	High Similarity	NPC197813
0.9314	High Similarity	NPC80338
0.9231	High Similarity	NPC193741
0.9216	High Similarity	NPC127235
0.9208	High Similarity	NPC37240
0.9109	High Similarity	NPC177013
0.9109	High Similarity	NPC4899
0.9109	High Similarity	NPC35185
0.9109	High Similarity	NPC474730
0.9057	High Similarity	NPC475851
0.9057	High Similarity	NPC475924
0.901	High Similarity	NPC287539
0.901	High Similarity	NPC3488
0.8922	High Similarity	NPC106668
0.8922	High Similarity	NPC304163
0.8835	High Similarity	NPC27687
0.8614	High Similarity	NPC170527
0.8614	High Similarity	NPC161293
0.8515	High Similarity	NPC93869
0.8515	High Similarity	NPC6765
0.8416	Intermediate Similarity	NPC274588
0.8381	Intermediate Similarity	NPC80144
0.8302	Intermediate Similarity	NPC329704
0.8286	Intermediate Similarity	NPC216911
0.8286	Intermediate Similarity	NPC67296
0.8269	Intermediate Similarity	NPC37866
0.8269	Intermediate Similarity	NPC49833
0.8269	Intermediate Similarity	NPC249171
0.8252	Intermediate Similarity	NPC284063
0.8235	Intermediate Similarity	NPC63897
0.8218	Intermediate Similarity	NPC235051
0.819	Intermediate Similarity	NPC476211
0.819	Intermediate Similarity	NPC476320
0.8173	Intermediate Similarity	NPC86843
0.8173	Intermediate Similarity	NPC304445
0.8173	Intermediate Similarity	NPC236580
0.8131	Intermediate Similarity	NPC329834
0.8131	Intermediate Similarity	NPC473148
0.8119	Intermediate Similarity	NPC246173
0.8113	Intermediate Similarity	NPC298255
0.8113	Intermediate Similarity	NPC27474
0.8113	Intermediate Similarity	NPC476230
0.8113	Intermediate Similarity	NPC28304
0.8103	Intermediate Similarity	NPC470829
0.8103	Intermediate Similarity	NPC473228
0.8077	Intermediate Similarity	NPC474297
0.8039	Intermediate Similarity	NPC473150
0.8039	Intermediate Similarity	NPC274274
0.8039	Intermediate Similarity	NPC294643
0.8019	Intermediate Similarity	NPC22149
0.8019	Intermediate Similarity	NPC255677
0.8019	Intermediate Similarity	NPC306344
0.8	Intermediate Similarity	NPC58267
0.8	Intermediate Similarity	NPC263674
0.8	Intermediate Similarity	NPC261372
0.7981	Intermediate Similarity	NPC101051
0.7944	Intermediate Similarity	NPC476228
0.789	Intermediate Similarity	NPC86095
0.787	Intermediate Similarity	NPC250545
0.787	Intermediate Similarity	NPC261117
0.787	Intermediate Similarity	NPC195510
0.787	Intermediate Similarity	NPC310804
0.787	Intermediate Similarity	NPC13171
0.7864	Intermediate Similarity	NPC66504
0.7845	Intermediate Similarity	NPC13710
0.7843	Intermediate Similarity	NPC93190
0.783	Intermediate Similarity	NPC471150
0.783	Intermediate Similarity	NPC474313
0.7826	Intermediate Similarity	NPC277583
0.7822	Intermediate Similarity	NPC31349
0.7818	Intermediate Similarity	NPC41681
0.781	Intermediate Similarity	NPC472873
0.781	Intermediate Similarity	NPC167893
0.7798	Intermediate Similarity	NPC267869
0.7798	Intermediate Similarity	NPC284929
0.7798	Intermediate Similarity	NPC118761
0.7798	Intermediate Similarity	NPC234304
0.7798	Intermediate Similarity	NPC197541
0.7767	Intermediate Similarity	NPC120021
0.7767	Intermediate Similarity	NPC117596
0.7767	Intermediate Similarity	NPC65665
0.7767	Intermediate Similarity	NPC270908
0.7767	Intermediate Similarity	NPC470573
0.7767	Intermediate Similarity	NPC216826
0.7767	Intermediate Similarity	NPC231710
0.7748	Intermediate Similarity	NPC474285
0.7748	Intermediate Similarity	NPC254538
0.7736	Intermediate Similarity	NPC241911
0.7723	Intermediate Similarity	NPC470657
0.7712	Intermediate Similarity	NPC281840
0.7706	Intermediate Similarity	NPC222062
0.7692	Intermediate Similarity	NPC184063
0.7692	Intermediate Similarity	NPC472125
0.7692	Intermediate Similarity	NPC472124
0.7692	Intermediate Similarity	NPC472126
0.7685	Intermediate Similarity	NPC186861
0.7685	Intermediate Similarity	NPC473146
0.7685	Intermediate Similarity	NPC471381
0.767	Intermediate Similarity	NPC50464
0.7664	Intermediate Similarity	NPC472290
0.7664	Intermediate Similarity	NPC311904
0.7658	Intermediate Similarity	NPC44004
0.7619	Intermediate Similarity	NPC61201
0.7615	Intermediate Similarity	NPC20673
0.7615	Intermediate Similarity	NPC4637
0.7615	Intermediate Similarity	NPC98859
0.7611	Intermediate Similarity	NPC208307
0.7596	Intermediate Similarity	NPC307699
0.7596	Intermediate Similarity	NPC19087
0.7593	Intermediate Similarity	NPC472015
0.7581	Intermediate Similarity	NPC213634
0.757	Intermediate Similarity	NPC476009
0.7549	Intermediate Similarity	NPC171484
0.7549	Intermediate Similarity	NPC149018
0.7547	Intermediate Similarity	NPC71589
0.7545	Intermediate Similarity	NPC471599
0.7544	Intermediate Similarity	NPC235014
0.7544	Intermediate Similarity	NPC106760
0.7542	Intermediate Similarity	NPC475309
0.7538	Intermediate Similarity	NPC5153
0.7538	Intermediate Similarity	NPC48414
0.7523	Intermediate Similarity	NPC244878
0.7522	Intermediate Similarity	NPC475960
0.7521	Intermediate Similarity	NPC88945
0.75	Intermediate Similarity	NPC181151
0.75	Intermediate Similarity	NPC38392
0.75	Intermediate Similarity	NPC54737
0.75	Intermediate Similarity	NPC132668
0.75	Intermediate Similarity	NPC215556
0.7478	Intermediate Similarity	NPC471251
0.7459	Intermediate Similarity	NPC318135
0.7458	Intermediate Similarity	NPC473304
0.7456	Intermediate Similarity	NPC59489
0.7456	Intermediate Similarity	NPC139838
0.7455	Intermediate Similarity	NPC219038
0.7455	Intermediate Similarity	NPC150923
0.7453	Intermediate Similarity	NPC475788
0.7442	Intermediate Similarity	NPC75616
0.744	Intermediate Similarity	NPC173347
0.7431	Intermediate Similarity	NPC45125
0.7431	Intermediate Similarity	NPC151093
0.7429	Intermediate Similarity	NPC474323
0.7429	Intermediate Similarity	NPC216284
0.7429	Intermediate Similarity	NPC206614
0.7424	Intermediate Similarity	NPC471172
0.7422	Intermediate Similarity	NPC289700
0.7422	Intermediate Similarity	NPC62172
0.7419	Intermediate Similarity	NPC311534
0.7411	Intermediate Similarity	NPC474917
0.7407	Intermediate Similarity	NPC470883
0.7407	Intermediate Similarity	NPC142529
0.7407	Intermediate Similarity	NPC306041
0.7407	Intermediate Similarity	NPC76862
0.7407	Intermediate Similarity	NPC158416
0.7407	Intermediate Similarity	NPC39859
0.7407	Intermediate Similarity	NPC91771
0.7404	Intermediate Similarity	NPC207114
0.7404	Intermediate Similarity	NPC217983
0.7404	Intermediate Similarity	NPC79549
0.7402	Intermediate Similarity	NPC471234
0.7395	Intermediate Similarity	NPC471249
0.7391	Intermediate Similarity	NPC50223
0.7391	Intermediate Similarity	NPC124053
0.7387	Intermediate Similarity	NPC313569
0.7381	Intermediate Similarity	NPC42206
0.7381	Intermediate Similarity	NPC155529
0.7381	Intermediate Similarity	NPC231240
0.7377	Intermediate Similarity	NPC1980
0.7377	Intermediate Similarity	NPC238005
0.7377	Intermediate Similarity	NPC141196
0.7373	Intermediate Similarity	NPC229752
0.7368	Intermediate Similarity	NPC224414
0.7368	Intermediate Similarity	NPC194854
0.7368	Intermediate Similarity	NPC48813
0.736	Intermediate Similarity	NPC472770
0.736	Intermediate Similarity	NPC476966
0.7358	Intermediate Similarity	NPC470373
0.7358	Intermediate Similarity	NPC470379
0.7355	Intermediate Similarity	NPC472001
0.7355	Intermediate Similarity	NPC129434
0.735	Intermediate Similarity	NPC102619
0.7348	Intermediate Similarity	NPC471171
0.7344	Intermediate Similarity	NPC158350
0.7339	Intermediate Similarity	NPC152091
0.7339	Intermediate Similarity	NPC40812
0.7339	Intermediate Similarity	NPC469757
0.7339	Intermediate Similarity	NPC471357
0.7339	Intermediate Similarity	NPC146456
0.7339	Intermediate Similarity	NPC117702
0.7333	Intermediate Similarity	NPC22918
0.7333	Intermediate Similarity	NPC219656
0.7333	Intermediate Similarity	NPC477092
0.7333	Intermediate Similarity	NPC232258
0.7333	Intermediate Similarity	NPC92974
0.7328	Intermediate Similarity	NPC63244
0.7328	Intermediate Similarity	NPC213320
0.7328	Intermediate Similarity	NPC56025

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 NPC110701 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	2262
0.2-0.3	3779
0.3-0.4	1861
0.4-0.5	586
0.5-0.6	291
0.6-0.7	115
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7222	Intermediate Similarity	NPD7319	Approved
0.7217	Intermediate Similarity	NPD6686	Approved
0.7213	Intermediate Similarity	NPD8513	Phase 3
0.7203	Intermediate Similarity	NPD8133	Approved
0.713	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7507	Approved
0.7094	Intermediate Similarity	NPD6371	Approved
0.7073	Intermediate Similarity	NPD8515	Approved
0.7073	Intermediate Similarity	NPD8516	Approved
0.7073	Intermediate Similarity	NPD8517	Approved
0.7073	Intermediate Similarity	NPD7503	Approved
0.7034	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6053	Discontinued
0.6838	Remote Similarity	NPD6412	Phase 2
0.6814	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6698	Approved
0.6789	Remote Similarity	NPD46	Approved
0.6748	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6370	Approved
0.6744	Remote Similarity	NPD7736	Approved
0.672	Remote Similarity	NPD6319	Approved
0.6694	Remote Similarity	NPD7328	Approved
0.6694	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6641	Remote Similarity	NPD7492	Approved
0.664	Remote Similarity	NPD7516	Approved
0.6614	Remote Similarity	NPD8080	Discontinued
0.6613	Remote Similarity	NPD7115	Discovery
0.6589	Remote Similarity	NPD6616	Approved
0.6587	Remote Similarity	NPD8377	Approved
0.6587	Remote Similarity	NPD6054	Approved
0.6587	Remote Similarity	NPD8294	Approved
0.6577	Remote Similarity	NPD7983	Approved
0.6562	Remote Similarity	NPD7642	Approved
0.6538	Remote Similarity	NPD7078	Approved
0.6538	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD8378	Approved
0.6535	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8380	Approved
0.6535	Remote Similarity	NPD8379	Approved
0.6535	Remote Similarity	NPD8296	Approved
0.6535	Remote Similarity	NPD8335	Approved
0.6535	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5785	Approved
0.6484	Remote Similarity	NPD5988	Approved
0.648	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8451	Approved
0.6457	Remote Similarity	NPD6059	Approved
0.6434	Remote Similarity	NPD7829	Approved
0.6434	Remote Similarity	NPD7830	Approved
0.6422	Remote Similarity	NPD4249	Approved
0.6412	Remote Similarity	NPD8448	Approved
0.6396	Remote Similarity	NPD1695	Approved
0.6385	Remote Similarity	NPD8340	Approved
0.6385	Remote Similarity	NPD8341	Approved
0.6385	Remote Similarity	NPD8299	Approved
0.6385	Remote Similarity	NPD8342	Approved
0.6379	Remote Similarity	NPD4225	Approved
0.6364	Remote Similarity	NPD4250	Approved
0.6364	Remote Similarity	NPD4251	Approved
0.6349	Remote Similarity	NPD6009	Approved
0.633	Remote Similarity	NPD5363	Approved
0.6316	Remote Similarity	NPD5282	Discontinued
0.6311	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8328	Phase 3
0.629	Remote Similarity	NPD6882	Approved
0.6286	Remote Similarity	NPD4238	Approved
0.6286	Remote Similarity	NPD4802	Phase 2
0.6273	Remote Similarity	NPD5786	Approved
0.6269	Remote Similarity	NPD8390	Approved
0.6269	Remote Similarity	NPD8392	Approved
0.6269	Remote Similarity	NPD8391	Approved
0.6262	Remote Similarity	NPD5369	Approved
0.6261	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.624	Remote Similarity	NPD4632	Approved
0.6232	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5779	Approved
0.6228	Remote Similarity	NPD5778	Approved
0.6218	Remote Similarity	NPD8139	Approved
0.6218	Remote Similarity	NPD8085	Approved
0.6218	Remote Similarity	NPD8086	Approved
0.6218	Remote Similarity	NPD8084	Approved
0.6218	Remote Similarity	NPD8138	Approved
0.6218	Remote Similarity	NPD8082	Approved
0.6218	Remote Similarity	NPD8083	Approved
0.6207	Remote Similarity	NPD7839	Suspended
0.6204	Remote Similarity	NPD4269	Approved
0.6204	Remote Similarity	NPD4270	Approved
0.6195	Remote Similarity	NPD7838	Discovery
0.6182	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7641	Discontinued
0.6167	Remote Similarity	NPD8275	Approved
0.6167	Remote Similarity	NPD8276	Approved
0.616	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD8266	Approved
0.6154	Remote Similarity	NPD8267	Approved
0.6154	Remote Similarity	NPD8444	Approved
0.6154	Remote Similarity	NPD8268	Approved
0.6154	Remote Similarity	NPD8269	Approved
0.6147	Remote Similarity	NPD7154	Phase 3
0.6147	Remote Similarity	NPD5362	Discontinued
0.6129	Remote Similarity	NPD4634	Approved
0.6119	Remote Similarity	NPD8336	Approved
0.6119	Remote Similarity	NPD8337	Approved
0.6116	Remote Similarity	NPD8081	Approved
0.608	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD6649	Approved
0.6066	Remote Similarity	NPD8393	Approved
0.6055	Remote Similarity	NPD6435	Approved
0.605	Remote Similarity	NPD7639	Approved
0.605	Remote Similarity	NPD7640	Approved
0.6048	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6372	Approved
0.6048	Remote Similarity	NPD6373	Approved
0.6036	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6921	Approved
0.6029	Remote Similarity	NPD5956	Approved
0.6019	Remote Similarity	NPD4252	Approved
0.6019	Remote Similarity	NPD4820	Approved
0.6019	Remote Similarity	NPD4822	Approved
0.6019	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4819	Approved
0.6019	Remote Similarity	NPD4821	Approved
0.6016	Remote Similarity	NPD5697	Approved
0.6	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5344	Discontinued
0.5968	Remote Similarity	NPD6881	Approved
0.5968	Remote Similarity	NPD6899	Approved
0.5966	Remote Similarity	NPD7638	Approved
0.5965	Remote Similarity	NPD6101	Approved
0.5965	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD8338	Approved
0.5935	Remote Similarity	NPD7128	Approved
0.5935	Remote Similarity	NPD5739	Approved
0.5935	Remote Similarity	NPD6675	Approved
0.5935	Remote Similarity	NPD6008	Approved
0.5935	Remote Similarity	NPD6402	Approved
0.592	Remote Similarity	NPD6012	Approved
0.592	Remote Similarity	NPD6014	Approved
0.592	Remote Similarity	NPD6013	Approved
0.5909	Remote Similarity	NPD5983	Phase 2
0.5887	Remote Similarity	NPD8140	Approved
0.5887	Remote Similarity	NPD8307	Discontinued
0.5887	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD6084	Phase 2
0.5882	Remote Similarity	NPD6083	Phase 2
0.5873	Remote Similarity	NPD6883	Approved
0.5873	Remote Similarity	NPD7290	Approved
0.5873	Remote Similarity	NPD7102	Approved
0.5872	Remote Similarity	NPD5368	Approved
0.587	Remote Similarity	NPD7260	Phase 2
0.5862	Remote Similarity	NPD6411	Approved
0.5856	Remote Similarity	NPD4788	Approved
0.5856	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3669	Approved
0.5847	Remote Similarity	NPD5695	Phase 3
0.584	Remote Similarity	NPD6011	Approved
0.584	Remote Similarity	NPD7320	Approved
0.5833	Remote Similarity	NPD5696	Approved
0.5833	Remote Similarity	NPD4268	Approved
0.5833	Remote Similarity	NPD4271	Approved
0.5827	Remote Similarity	NPD6845	Suspended
0.5827	Remote Similarity	NPD6847	Approved
0.5827	Remote Similarity	NPD8130	Phase 1
0.5827	Remote Similarity	NPD6869	Approved
0.5827	Remote Similarity	NPD6617	Approved
0.5821	Remote Similarity	NPD6067	Discontinued
0.5821	Remote Similarity	NPD7604	Phase 2
0.582	Remote Similarity	NPD5211	Phase 2
0.582	Remote Similarity	NPD7632	Discontinued
0.5818	Remote Similarity	NPD1780	Approved
0.5818	Remote Similarity	NPD1779	Approved
0.5812	Remote Similarity	NPD6399	Phase 3
0.5804	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD8306	Approved
0.5794	Remote Similarity	NPD8305	Approved
0.5789	Remote Similarity	NPD7524	Approved
0.5784	Remote Similarity	NPD896	Approved
0.5784	Remote Similarity	NPD897	Approved
0.5784	Remote Similarity	NPD898	Approved
0.576	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7685	Pre-registration
0.5748	Remote Similarity	NPD8087	Discontinued
0.5738	Remote Similarity	NPD1700	Approved
0.5735	Remote Similarity	NPD6336	Discontinued
0.5735	Remote Similarity	NPD8273	Phase 1
0.5726	Remote Similarity	NPD8035	Phase 2
0.5726	Remote Similarity	NPD5141	Approved
0.5726	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD5331	Approved
0.5714	Remote Similarity	NPD5332	Approved
0.5701	Remote Similarity	NPD3702	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