NPASS Compound

Structure

CID70733 OpenBabel06191715412D 36 38 0 0 1 0 0 0 0 0999 V2000 -2.5981 -4.5000 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 2 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 3.4641 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 2 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 1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 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 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 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 2.5981 -5.5000 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 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 14 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 15 1 0 0 0 0 12 2 1 6 0 0 0 12 33 1 0 0 0 0 13 3 1 1 0 0 0 13 17 1 0 0 0 0 13 34 1 0 0 0 0 14 27 2 0 0 0 0 15 7 1 6 0 0 0 15 25 1 0 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 35 1 0 0 0 0 17 19 1 0 0 0 0 17 28 1 6 0 0 0 18 20 1 0 0 0 0 18 29 1 1 0 0 0 19 21 1 0 0 0 0 19 30 1 1 0 0 0 20 22 1 0 0 0 0 20 31 1 6 0 0 0 21 23 1 0 0 0 0 21 32 1 1 0 0 0 22 24 1 0 0 0 0 22 36 1 1 0 0 0 23 34 1 0 0 0 0 23 36 1 6 0 0 0 24 33 1 6 0 0 0 24 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	194.06
Volume:	194.938
LogP:	1.803
LogD:	2.724
LogS:	-1.761
# Rotatable Bonds:	3
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	1.869
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	1.4585020835511386e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.086
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.584

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	89.75426483154297%
Volume Distribution (VD):	0.339
Pgp-substrate:	6.394725322723389%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.478
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.367
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	7.48
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.511
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.733
Maximum Recommended Daily Dose:	0.076
Skin Sensitization:	0.929
Carcinogencity:	0.443
Eye Corrosion:	0.515
Eye Irritation:	0.979
Respiratory Toxicity:	0.72

Download Data

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

Natural Product: NPC70733

Natural Product ID:	NPC70733
*Common Name:**	Gusanlungionoside C
IUPAC Name:	(4S)-4-[(3R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxybutyl]-3,5,5-trimethylcyclohex-2-en-1-one
Synonyms:	Gusanlungionoside C
Standard InCHIKey:	ZUTSCUCRFVUYIA-XUGLSIFHSA-N
Standard InCHI:	InChI=1S/C25H42O11/c1-11-8-14(27)9-25(4,5)15(11)7-6-12(2)33-24-22(20(31)18(29)16(10-26)35-24)36-23-21(32)19(30)17(28)13(3)34-23/h8,12-13,15-24,26,28-32H,6-7,9-10H2,1-5H3/t12-,13+,15-,16-,17+,18-,19-,20+,21-,22-,23+,24-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H](CC[C@@H]2C(=CC(=O)CC2(C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813175
PubChem CID:	53355122
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19018	Senecio provincialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4674	Gaillardia powellii	Species	Asteraceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	200000.0	nM	PMID[485697]

☑ 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 NPC70733 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	203
0.1-0.2	1215
0.2-0.3	4558
0.3-0.4	8937
0.4-0.5	12413
0.5-0.6	7087
0.6-0.7	6464
0.7-0.8	1693
0.8-0.85	103
0.85-0.9	20
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC56071
0.967	High Similarity	NPC108141
0.9462	High Similarity	NPC278506
0.9072	High Similarity	NPC223834
0.9	High Similarity	NPC473288
0.8958	High Similarity	NPC198422
0.8958	High Similarity	NPC40182
0.8812	High Similarity	NPC272576
0.875	High Similarity	NPC256230
0.8725	High Similarity	NPC246205
0.8667	High Similarity	NPC165439
0.8654	High Similarity	NPC471967
0.8627	High Similarity	NPC177524
0.8627	High Similarity	NPC219900
0.8627	High Similarity	NPC392
0.8571	High Similarity	NPC293038
0.8571	High Similarity	NPC477944
0.8571	High Similarity	NPC62696
0.8571	High Similarity	NPC260665
0.8557	High Similarity	NPC143446
0.8542	High Similarity	NPC2003
0.8542	High Similarity	NPC25701
0.8529	High Similarity	NPC293512
0.8515	High Similarity	NPC121566
0.8515	High Similarity	NPC100955
0.8505	High Similarity	NPC309433
0.8491	Intermediate Similarity	NPC102088
0.8491	Intermediate Similarity	NPC74727
0.8476	Intermediate Similarity	NPC474265
0.8476	Intermediate Similarity	NPC210420
0.8462	Intermediate Similarity	NPC474589
0.8462	Intermediate Similarity	NPC270667
0.8462	Intermediate Similarity	NPC269095
0.8462	Intermediate Similarity	NPC174679
0.8462	Intermediate Similarity	NPC127056
0.8462	Intermediate Similarity	NPC164194
0.8462	Intermediate Similarity	NPC475317
0.8462	Intermediate Similarity	NPC136877
0.8462	Intermediate Similarity	NPC56713
0.8462	Intermediate Similarity	NPC29069
0.8462	Intermediate Similarity	NPC279554
0.8462	Intermediate Similarity	NPC83005
0.8462	Intermediate Similarity	NPC59804
0.8462	Intermediate Similarity	NPC475296
0.8462	Intermediate Similarity	NPC90856
0.8462	Intermediate Similarity	NPC78046
0.8462	Intermediate Similarity	NPC52241
0.8462	Intermediate Similarity	NPC154856
0.8431	Intermediate Similarity	NPC95243
0.8431	Intermediate Similarity	NPC210178
0.8431	Intermediate Similarity	NPC162033
0.8431	Intermediate Similarity	NPC63023
0.8416	Intermediate Similarity	NPC151516
0.8411	Intermediate Similarity	NPC31797
0.8404	Intermediate Similarity	NPC471756
0.8404	Intermediate Similarity	NPC471755
0.8381	Intermediate Similarity	NPC211798
0.8381	Intermediate Similarity	NPC30397
0.8381	Intermediate Similarity	NPC235841
0.8381	Intermediate Similarity	NPC473481
0.8381	Intermediate Similarity	NPC297208
0.8381	Intermediate Similarity	NPC164419
0.8381	Intermediate Similarity	NPC108748
0.8381	Intermediate Similarity	NPC179434
0.8365	Intermediate Similarity	NPC137917
0.8365	Intermediate Similarity	NPC204407
0.8365	Intermediate Similarity	NPC118225
0.8365	Intermediate Similarity	NPC237503
0.8365	Intermediate Similarity	NPC57362
0.8365	Intermediate Similarity	NPC306746
0.8365	Intermediate Similarity	NPC167383
0.8349	Intermediate Similarity	NPC190939
0.8349	Intermediate Similarity	NPC197003
0.8349	Intermediate Similarity	NPC473401
0.8333	Intermediate Similarity	NPC223741
0.8318	Intermediate Similarity	NPC474557
0.8318	Intermediate Similarity	NPC473882
0.8302	Intermediate Similarity	NPC109079
0.8302	Intermediate Similarity	NPC10320
0.8302	Intermediate Similarity	NPC80843
0.8302	Intermediate Similarity	NPC1046
0.8302	Intermediate Similarity	NPC256798
0.8302	Intermediate Similarity	NPC101744
0.8302	Intermediate Similarity	NPC471383
0.8302	Intermediate Similarity	NPC104400
0.8302	Intermediate Similarity	NPC130427
0.8302	Intermediate Similarity	NPC139894
0.8302	Intermediate Similarity	NPC475516
0.8302	Intermediate Similarity	NPC324875
0.8302	Intermediate Similarity	NPC79718
0.8302	Intermediate Similarity	NPC475504
0.8302	Intermediate Similarity	NPC469946
0.8302	Intermediate Similarity	NPC104071
0.8302	Intermediate Similarity	NPC174836
0.8302	Intermediate Similarity	NPC276093
0.8302	Intermediate Similarity	NPC473373
0.8302	Intermediate Similarity	NPC473383
0.8302	Intermediate Similarity	NPC128925
0.8302	Intermediate Similarity	NPC292677
0.8302	Intermediate Similarity	NPC257468
0.8302	Intermediate Similarity	NPC139044
0.8302	Intermediate Similarity	NPC102439
0.8286	Intermediate Similarity	NPC476882
0.8286	Intermediate Similarity	NPC102914
0.8286	Intermediate Similarity	NPC129340
0.8286	Intermediate Similarity	NPC75747
0.8286	Intermediate Similarity	NPC476883
0.8286	Intermediate Similarity	NPC476887
0.8286	Intermediate Similarity	NPC476881
0.8286	Intermediate Similarity	NPC127153
0.8286	Intermediate Similarity	NPC68419
0.8286	Intermediate Similarity	NPC114961
0.8286	Intermediate Similarity	NPC108709
0.8286	Intermediate Similarity	NPC110139
0.8286	Intermediate Similarity	NPC7870
0.8286	Intermediate Similarity	NPC476886
0.8286	Intermediate Similarity	NPC476884
0.8286	Intermediate Similarity	NPC220984
0.8286	Intermediate Similarity	NPC274507
0.8286	Intermediate Similarity	NPC27551
0.8286	Intermediate Similarity	NPC199457
0.8286	Intermediate Similarity	NPC476885
0.8286	Intermediate Similarity	NPC476880
0.8283	Intermediate Similarity	NPC474194
0.8273	Intermediate Similarity	NPC308459
0.8269	Intermediate Similarity	NPC177246
0.8269	Intermediate Similarity	NPC476123
0.8269	Intermediate Similarity	NPC284807
0.8269	Intermediate Similarity	NPC295389
0.8269	Intermediate Similarity	NPC28198
0.8257	Intermediate Similarity	NPC234522
0.8257	Intermediate Similarity	NPC176005
0.8241	Intermediate Similarity	NPC279638
0.8241	Intermediate Similarity	NPC473126
0.8224	Intermediate Similarity	NPC189884
0.8224	Intermediate Similarity	NPC251263
0.8224	Intermediate Similarity	NPC134835
0.8224	Intermediate Similarity	NPC163183
0.8224	Intermediate Similarity	NPC311592
0.8224	Intermediate Similarity	NPC241909
0.8224	Intermediate Similarity	NPC166422
0.8224	Intermediate Similarity	NPC475208
0.8224	Intermediate Similarity	NPC155410
0.8224	Intermediate Similarity	NPC309714
0.8224	Intermediate Similarity	NPC47063
0.8224	Intermediate Similarity	NPC114304
0.8224	Intermediate Similarity	NPC258885
0.8224	Intermediate Similarity	NPC133818
0.8224	Intermediate Similarity	NPC475287
0.8224	Intermediate Similarity	NPC475467
0.8224	Intermediate Similarity	NPC473343
0.8224	Intermediate Similarity	NPC73455
0.8224	Intermediate Similarity	NPC323341
0.8224	Intermediate Similarity	NPC96641
0.8224	Intermediate Similarity	NPC75167
0.8224	Intermediate Similarity	NPC295823
0.8224	Intermediate Similarity	NPC46665
0.8224	Intermediate Similarity	NPC200944
0.8224	Intermediate Similarity	NPC138334
0.8224	Intermediate Similarity	NPC204458
0.8224	Intermediate Similarity	NPC251309
0.8224	Intermediate Similarity	NPC192600
0.8224	Intermediate Similarity	NPC174720
0.8224	Intermediate Similarity	NPC219180
0.8224	Intermediate Similarity	NPC238935
0.8224	Intermediate Similarity	NPC151543
0.8224	Intermediate Similarity	NPC150400
0.8224	Intermediate Similarity	NPC473826
0.8224	Intermediate Similarity	NPC124296
0.8224	Intermediate Similarity	NPC114287
0.8224	Intermediate Similarity	NPC73318
0.8218	Intermediate Similarity	NPC476611
0.8218	Intermediate Similarity	NPC154127
0.8208	Intermediate Similarity	NPC191763
0.8208	Intermediate Similarity	NPC250481
0.8208	Intermediate Similarity	NPC285410
0.8208	Intermediate Similarity	NPC31839
0.8208	Intermediate Similarity	NPC263827
0.82	Intermediate Similarity	NPC307517
0.82	Intermediate Similarity	NPC61630
0.82	Intermediate Similarity	NPC169468
0.82	Intermediate Similarity	NPC477928
0.82	Intermediate Similarity	NPC81483
0.8198	Intermediate Similarity	NPC476675
0.819	Intermediate Similarity	NPC265655
0.819	Intermediate Similarity	NPC127853
0.8182	Intermediate Similarity	NPC319570
0.8173	Intermediate Similarity	NPC283849
0.8173	Intermediate Similarity	NPC473538
0.8165	Intermediate Similarity	NPC474483
0.8165	Intermediate Similarity	NPC471580
0.8163	Intermediate Similarity	NPC477927
0.8163	Intermediate Similarity	NPC72817
0.8148	Intermediate Similarity	NPC475160
0.8148	Intermediate Similarity	NPC294453
0.8148	Intermediate Similarity	NPC4328
0.8148	Intermediate Similarity	NPC41061
0.8148	Intermediate Similarity	NPC469782
0.8148	Intermediate Similarity	NPC475486
0.8148	Intermediate Similarity	NPC119592

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 NPC70733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1586
0.2-0.3	3876
0.3-0.4	2292
0.4-0.5	692
0.5-0.6	255
0.6-0.7	237
0.7-0.8	29
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.89	High Similarity	NPD6412	Phase 2
0.8627	High Similarity	NPD6686	Approved
0.8053	Intermediate Similarity	NPD8328	Phase 3
0.8019	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.75	Intermediate Similarity	NPD46	Approved
0.7458	Intermediate Similarity	NPD7507	Approved
0.7411	Intermediate Similarity	NPD8133	Approved
0.7328	Intermediate Similarity	NPD6054	Approved
0.7328	Intermediate Similarity	NPD6059	Approved
0.7288	Intermediate Similarity	NPD6067	Discontinued
0.7273	Intermediate Similarity	NPD7319	Approved
0.725	Intermediate Similarity	NPD8293	Discontinued
0.719	Intermediate Similarity	NPD7736	Approved
0.7179	Intermediate Similarity	NPD8294	Approved
0.7179	Intermediate Similarity	NPD8377	Approved
0.7168	Intermediate Similarity	NPD6882	Approved
0.7155	Intermediate Similarity	NPD7328	Approved
0.7155	Intermediate Similarity	NPD7327	Approved
0.7119	Intermediate Similarity	NPD8378	Approved
0.7119	Intermediate Similarity	NPD8296	Approved
0.7119	Intermediate Similarity	NPD6015	Approved
0.7119	Intermediate Similarity	NPD8380	Approved
0.7119	Intermediate Similarity	NPD8335	Approved
0.7119	Intermediate Similarity	NPD7503	Approved
0.7119	Intermediate Similarity	NPD8033	Approved
0.7119	Intermediate Similarity	NPD6016	Approved
0.7119	Intermediate Similarity	NPD8379	Approved
0.7115	Intermediate Similarity	NPD7748	Approved
0.7094	Intermediate Similarity	NPD7516	Approved
0.7087	Intermediate Similarity	NPD7515	Phase 2
0.7087	Intermediate Similarity	NPD6411	Approved
0.7083	Intermediate Similarity	NPD7492	Approved
0.708	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD7902	Approved
0.7071	Intermediate Similarity	NPD3665	Phase 1
0.7071	Intermediate Similarity	NPD3666	Approved
0.7071	Intermediate Similarity	NPD3133	Approved
0.7069	Intermediate Similarity	NPD6009	Approved
0.7059	Intermediate Similarity	NPD5988	Approved
0.7034	Intermediate Similarity	NPD6319	Approved
0.7025	Intermediate Similarity	NPD6616	Approved
0.7019	Intermediate Similarity	NPD6399	Phase 3
0.7018	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD8513	Phase 3
0.6975	Remote Similarity	NPD8517	Approved
0.6975	Remote Similarity	NPD8515	Approved
0.6975	Remote Similarity	NPD8516	Approved
0.6967	Remote Similarity	NPD7078	Approved
0.6957	Remote Similarity	NPD4632	Approved
0.6952	Remote Similarity	NPD5282	Discontinued
0.6937	Remote Similarity	NPD5739	Approved
0.6937	Remote Similarity	NPD6675	Approved
0.6937	Remote Similarity	NPD6402	Approved
0.6937	Remote Similarity	NPD7128	Approved
0.6931	Remote Similarity	NPD7521	Approved
0.6931	Remote Similarity	NPD5279	Phase 3
0.6931	Remote Similarity	NPD3618	Phase 1
0.6931	Remote Similarity	NPD7334	Approved
0.6931	Remote Similarity	NPD6684	Approved
0.6931	Remote Similarity	NPD6409	Approved
0.6931	Remote Similarity	NPD7146	Approved
0.6931	Remote Similarity	NPD5330	Approved
0.6903	Remote Similarity	NPD6373	Approved
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6372	Approved
0.69	Remote Similarity	NPD4786	Approved
0.6893	Remote Similarity	NPD5328	Approved
0.6893	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6101	Approved
0.6893	Remote Similarity	NPD4753	Phase 2
0.6887	Remote Similarity	NPD5695	Phase 3
0.6869	Remote Similarity	NPD3667	Approved
0.6864	Remote Similarity	NPD7641	Discontinued
0.6852	Remote Similarity	NPD7638	Approved
0.6847	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4695	Discontinued
0.6814	Remote Similarity	NPD7320	Approved
0.6814	Remote Similarity	NPD6881	Approved
0.6814	Remote Similarity	NPD6899	Approved
0.6796	Remote Similarity	NPD6903	Approved
0.6796	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6672	Approved
0.6796	Remote Similarity	NPD5737	Approved
0.6792	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7640	Approved
0.6789	Remote Similarity	NPD7639	Approved
0.6783	Remote Similarity	NPD6650	Approved
0.6783	Remote Similarity	NPD6649	Approved
0.6774	Remote Similarity	NPD6033	Approved
0.6774	Remote Similarity	NPD8336	Approved
0.6774	Remote Similarity	NPD8337	Approved
0.6762	Remote Similarity	NPD7983	Approved
0.6762	Remote Similarity	NPD6079	Approved
0.6759	Remote Similarity	NPD4755	Approved
0.6726	Remote Similarity	NPD5701	Approved
0.6726	Remote Similarity	NPD5697	Approved
0.6698	Remote Similarity	NPD4202	Approved
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6697	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD6883	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6371	Approved
0.6696	Remote Similarity	NPD7290	Approved
0.6696	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6639	Remote Similarity	NPD7115	Discovery
0.6639	Remote Similarity	NPD8080	Discontinued
0.6638	Remote Similarity	NPD6869	Approved
0.6638	Remote Similarity	NPD8130	Phase 1
0.6638	Remote Similarity	NPD6617	Approved
0.6638	Remote Similarity	NPD6847	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6609	Remote Similarity	NPD6012	Approved
0.6609	Remote Similarity	NPD6014	Approved
0.6609	Remote Similarity	NPD6013	Approved
0.6585	Remote Similarity	NPD7830	Approved
0.6585	Remote Similarity	NPD7604	Phase 2
0.6585	Remote Similarity	NPD7829	Approved
0.6581	Remote Similarity	NPD6053	Discontinued
0.6574	Remote Similarity	NPD5210	Approved
0.6574	Remote Similarity	NPD4629	Approved
0.6569	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5983	Phase 2
0.6545	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD4221	Approved
0.6535	Remote Similarity	NPD4223	Phase 3
0.6535	Remote Similarity	NPD6914	Discontinued
0.6522	Remote Similarity	NPD6011	Approved
0.6518	Remote Similarity	NPD5224	Approved
0.6518	Remote Similarity	NPD5211	Phase 2
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD4633	Approved
0.6514	Remote Similarity	NPD5221	Approved
0.6514	Remote Similarity	NPD4697	Phase 3
0.6514	Remote Similarity	NPD5222	Approved
0.6514	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5329	Approved
0.65	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4768	Approved
0.6491	Remote Similarity	NPD4767	Approved
0.6491	Remote Similarity	NPD6008	Approved
0.648	Remote Similarity	NPD6336	Discontinued
0.6471	Remote Similarity	NPD6110	Phase 1
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD5173	Approved
0.6449	Remote Similarity	NPD5284	Approved
0.6449	Remote Similarity	NPD5281	Approved
0.6435	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8074	Phase 3
0.6429	Remote Similarity	NPD5223	Approved
0.6423	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6904	Approved
0.6415	Remote Similarity	NPD6080	Approved
0.6415	Remote Similarity	NPD6673	Approved
0.6408	Remote Similarity	NPD3668	Phase 3
0.6408	Remote Similarity	NPD4197	Approved
0.6404	Remote Similarity	NPD5141	Approved
0.64	Remote Similarity	NPD8341	Approved
0.64	Remote Similarity	NPD8299	Approved
0.64	Remote Similarity	NPD8340	Approved
0.64	Remote Similarity	NPD8342	Approved
0.6381	Remote Similarity	NPD3573	Approved
0.6381	Remote Similarity	NPD7524	Approved
0.6379	Remote Similarity	NPD4730	Approved
0.6379	Remote Similarity	NPD4729	Approved
0.6373	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6435	Approved
0.6364	Remote Similarity	NPD7839	Suspended
0.6357	Remote Similarity	NPD7260	Phase 2
0.6349	Remote Similarity	NPD8451	Approved
0.6337	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7642	Approved
0.6316	Remote Similarity	NPD4754	Approved
0.6311	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3669	Approved
0.63	Remote Similarity	NPD3617	Approved
0.6299	Remote Similarity	NPD8448	Approved
0.6296	Remote Similarity	NPD6050	Approved
0.629	Remote Similarity	NPD8444	Approved
0.6286	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4693	Phase 3

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