NPASS Compound

Structure

NPC474182 OpenBabel07101718302D 32 35 0 0 1 0 0 0 0 0999 V2000 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1902 -0.2750 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 -3.2604 2.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1264 2.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1974 -1.7549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2162 -1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4635 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1687 -0.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3168 -0.7620 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 -2.7293 -1.0747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3944 1.1472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4094 -0.3417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2604 0.6472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 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 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2604 1.6472 0.0000 C 0 0 0 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 2.5981 0.5000 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 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 13 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 13 2 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 12 26 1 0 0 0 0 13 23 1 0 0 0 0 14 3 1 1 0 0 0 14 18 1 0 0 0 0 15 4 1 6 0 0 0 15 20 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 1 0 0 0 17 11 1 6 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 30 1 0 0 0 0 24 32 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.3
Volume:	471.495
LogP:	5.108
LogD:	4.896
LogS:	-4.817
# Rotatable Bonds:	5
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	5.043
Fsp3:	0.885
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:	-4.732
MDCK Permeability:	2.825250521709677e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.798
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.675

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	94.91807556152344%
Volume Distribution (VD):	2.15
Pgp-substrate:	2.9990110397338867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.843
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.426
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.452
CYP3A4-substrate:	0.491

ADMET: Excretion

Clearance (CL):	5.25
Half-life (T1/2):	0.403

ADMET: Toxicity

hERG Blockers:	0.53
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.549
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.143
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.805
Carcinogencity:	0.034
Eye Corrosion:	0.051
Eye Irritation:	0.053
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC474182

Natural Product ID:	NPC474182
*Common Name:**	((2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-Methyl-2-((1Ar,4R,4As,7R,7As,7Bs)-1,1,4,7-Tetramethyldecahydro-1H-Cyclopropa[E]Azulen-4-Yloxy)Tetrahydro-2H-Pyran-3-Yl) 2-Methylbut-2-Enoate
IUPAC Name:	[(2S,3R,4S,5R,6R)-2-[[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	ZJDFOCVQLXHEEJ-CHSBRROWSA-N
Standard InCHI:	InChI=1S/C26H42O6/c1-8-13(2)23(29)31-22-21(28)20(27)15(4)30-24(22)32-26(7)12-11-17-19(25(17,5)6)18-14(3)9-10-16(18)26/h8,14-22,24,27-28H,9-12H2,1-7H3/b13-8+/t14-,15-,16+,17-,18-,19-,20+,21+,22-,24+,26-/m1/s1
SMILES:	C/C=C(/C(=O)O[C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1O)O)C)O[C@]1(C)CC[C@@H]2[C@H]([C@H]3[C@@H]1CC[C@H]3C)C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463262
PubChem CID:	44567063
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1965654]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17716	Calendula arvensis	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
Others	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	22.0	%	PMID[490540]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	13.0	%	PMID[490540]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	0.0	%	PMID[490540]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC50	>	20.0	ug.mL-1	PMID[490540]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	Activity	=	0.0	%	PMID[490540]

☑ 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 NPC474182 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	237
0.1-0.2	1921
0.2-0.3	6674
0.3-0.4	14252
0.4-0.5	8110
0.5-0.6	7646
0.6-0.7	3606
0.7-0.8	245
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC130792
0.8444	Intermediate Similarity	NPC475849
0.8352	Intermediate Similarity	NPC474266
0.8333	Intermediate Similarity	NPC216941
0.8155	Intermediate Similarity	NPC85670
0.7925	Intermediate Similarity	NPC257853
0.7889	Intermediate Similarity	NPC188793
0.7857	Intermediate Similarity	NPC477749
0.7838	Intermediate Similarity	NPC13710
0.781	Intermediate Similarity	NPC239961
0.7778	Intermediate Similarity	NPC472196
0.7778	Intermediate Similarity	NPC238090
0.7778	Intermediate Similarity	NPC472195
0.7767	Intermediate Similarity	NPC198992
0.7755	Intermediate Similarity	NPC202886
0.7745	Intermediate Similarity	NPC472015
0.7727	Intermediate Similarity	NPC106446
0.77	Intermediate Similarity	NPC159698
0.7677	Intermediate Similarity	NPC235051
0.7664	Intermediate Similarity	NPC177524
0.7664	Intermediate Similarity	NPC392
0.7664	Intermediate Similarity	NPC219900
0.7653	Intermediate Similarity	NPC477748
0.7636	Intermediate Similarity	NPC287075
0.7632	Intermediate Similarity	NPC470829
0.7632	Intermediate Similarity	NPC473228
0.7624	Intermediate Similarity	NPC93869
0.7624	Intermediate Similarity	NPC6765
0.7619	Intermediate Similarity	NPC473148
0.7615	Intermediate Similarity	NPC470076
0.7615	Intermediate Similarity	NPC71680
0.76	Intermediate Similarity	NPC474835
0.7589	Intermediate Similarity	NPC290693
0.7573	Intermediate Similarity	NPC49833
0.7573	Intermediate Similarity	NPC249171
0.7568	Intermediate Similarity	NPC471633
0.7568	Intermediate Similarity	NPC84949
0.7568	Intermediate Similarity	NPC69576
0.7568	Intermediate Similarity	NPC31354
0.7525	Intermediate Similarity	NPC274588
0.7524	Intermediate Similarity	NPC121423
0.7524	Intermediate Similarity	NPC201191
0.7523	Intermediate Similarity	NPC15551
0.75	Intermediate Similarity	NPC199428
0.75	Intermediate Similarity	NPC288471
0.75	Intermediate Similarity	NPC310341
0.75	Intermediate Similarity	NPC5311
0.75	Intermediate Similarity	NPC79631
0.75	Intermediate Similarity	NPC207637
0.75	Intermediate Similarity	NPC193382
0.75	Intermediate Similarity	NPC99620
0.75	Intermediate Similarity	NPC266718
0.7477	Intermediate Similarity	NPC82251
0.7476	Intermediate Similarity	NPC309503
0.7476	Intermediate Similarity	NPC91197
0.7476	Intermediate Similarity	NPC304445
0.7476	Intermediate Similarity	NPC96597
0.7476	Intermediate Similarity	NPC239547
0.7476	Intermediate Similarity	NPC155319
0.7476	Intermediate Similarity	NPC125551
0.7476	Intermediate Similarity	NPC236580
0.7453	Intermediate Similarity	NPC37240
0.7451	Intermediate Similarity	NPC220221
0.7434	Intermediate Similarity	NPC473852
0.7434	Intermediate Similarity	NPC243196
0.7434	Intermediate Similarity	NPC471355
0.7434	Intermediate Similarity	NPC474418
0.7434	Intermediate Similarity	NPC471351
0.7434	Intermediate Similarity	NPC471353
0.7434	Intermediate Similarity	NPC158344
0.7434	Intermediate Similarity	NPC84987
0.7434	Intermediate Similarity	NPC27507
0.7434	Intermediate Similarity	NPC34390
0.7434	Intermediate Similarity	NPC157376
0.7434	Intermediate Similarity	NPC196429
0.7434	Intermediate Similarity	NPC87250
0.7434	Intermediate Similarity	NPC244402
0.7434	Intermediate Similarity	NPC142066
0.7434	Intermediate Similarity	NPC77319
0.7434	Intermediate Similarity	NPC99728
0.7434	Intermediate Similarity	NPC50305
0.7434	Intermediate Similarity	NPC203862
0.7434	Intermediate Similarity	NPC152615
0.7434	Intermediate Similarity	NPC93883
0.7434	Intermediate Similarity	NPC471354
0.7434	Intermediate Similarity	NPC309034
0.7429	Intermediate Similarity	NPC219038
0.7411	Intermediate Similarity	NPC216665
0.7391	Intermediate Similarity	NPC135369
0.7391	Intermediate Similarity	NPC470312
0.7387	Intermediate Similarity	NPC241477
0.7379	Intermediate Similarity	NPC98165
0.7379	Intermediate Similarity	NPC170527
0.7373	Intermediate Similarity	NPC222307
0.7368	Intermediate Similarity	NPC83287
0.7364	Intermediate Similarity	NPC257240
0.7358	Intermediate Similarity	NPC35185
0.7358	Intermediate Similarity	NPC177013
0.7358	Intermediate Similarity	NPC200672
0.7358	Intermediate Similarity	NPC471599
0.7358	Intermediate Similarity	NPC214714
0.7358	Intermediate Similarity	NPC106668
0.7358	Intermediate Similarity	NPC4899
0.7358	Intermediate Similarity	NPC80144
0.7358	Intermediate Similarity	NPC474730
0.7353	Intermediate Similarity	NPC256368
0.7347	Intermediate Similarity	NPC311163
0.7345	Intermediate Similarity	NPC470075
0.7333	Intermediate Similarity	NPC244878
0.7321	Intermediate Similarity	NPC264153
0.732	Intermediate Similarity	NPC475035
0.7315	Intermediate Similarity	NPC29389
0.7315	Intermediate Similarity	NPC93026
0.7315	Intermediate Similarity	NPC469960
0.7315	Intermediate Similarity	NPC265502
0.7315	Intermediate Similarity	NPC54737
0.7308	Intermediate Similarity	NPC263674
0.7308	Intermediate Similarity	NPC261372
0.7308	Intermediate Similarity	NPC86843
0.7308	Intermediate Similarity	NPC58267
0.7304	Intermediate Similarity	NPC304260
0.7304	Intermediate Similarity	NPC236973
0.7304	Intermediate Similarity	NPC55532
0.7304	Intermediate Similarity	NPC5883
0.7304	Intermediate Similarity	NPC44899
0.7304	Intermediate Similarity	NPC469756
0.7304	Intermediate Similarity	NPC30483
0.7304	Intermediate Similarity	NPC153085
0.7304	Intermediate Similarity	NPC268326
0.7304	Intermediate Similarity	NPC32177
0.7304	Intermediate Similarity	NPC29639
0.7304	Intermediate Similarity	NPC219656
0.7304	Intermediate Similarity	NPC329905
0.7304	Intermediate Similarity	NPC470897
0.7304	Intermediate Similarity	NPC292467
0.729	Intermediate Similarity	NPC329834
0.729	Intermediate Similarity	NPC27687
0.729	Intermediate Similarity	NPC475928
0.7282	Intermediate Similarity	NPC167893
0.7282	Intermediate Similarity	NPC240838
0.7273	Intermediate Similarity	NPC45957
0.7273	Intermediate Similarity	NPC477102
0.7273	Intermediate Similarity	NPC206618
0.7273	Intermediate Similarity	NPC471657
0.7265	Intermediate Similarity	NPC115349
0.7264	Intermediate Similarity	NPC216911
0.7264	Intermediate Similarity	NPC285231
0.7264	Intermediate Similarity	NPC26557
0.7264	Intermediate Similarity	NPC67296
0.7264	Intermediate Similarity	NPC21568
0.7264	Intermediate Similarity	NPC20673
0.7264	Intermediate Similarity	NPC280991
0.7257	Intermediate Similarity	NPC43213
0.7255	Intermediate Similarity	NPC320089
0.725	Intermediate Similarity	NPC114306
0.725	Intermediate Similarity	NPC477490
0.725	Intermediate Similarity	NPC270109
0.7248	Intermediate Similarity	NPC108682
0.7248	Intermediate Similarity	NPC80338
0.7248	Intermediate Similarity	NPC469957
0.7248	Intermediate Similarity	NPC148270
0.7248	Intermediate Similarity	NPC469959
0.7248	Intermediate Similarity	NPC472263
0.7248	Intermediate Similarity	NPC197813
0.7245	Intermediate Similarity	NPC471494
0.7241	Intermediate Similarity	NPC475136
0.7241	Intermediate Similarity	NPC474466
0.7241	Intermediate Similarity	NPC281840
0.7241	Intermediate Similarity	NPC72260
0.7241	Intermediate Similarity	NPC475629
0.7241	Intermediate Similarity	NPC475556
0.7238	Intermediate Similarity	NPC65700
0.7238	Intermediate Similarity	NPC151093
0.7238	Intermediate Similarity	NPC474957
0.7238	Intermediate Similarity	NPC79449
0.7232	Intermediate Similarity	NPC313921
0.7232	Intermediate Similarity	NPC98038
0.7222	Intermediate Similarity	NPC161775
0.7217	Intermediate Similarity	NPC218093
0.7212	Intermediate Similarity	NPC284063
0.7212	Intermediate Similarity	NPC18019
0.7212	Intermediate Similarity	NPC474297
0.7212	Intermediate Similarity	NPC54731
0.7212	Intermediate Similarity	NPC24956
0.7212	Intermediate Similarity	NPC126156
0.7207	Intermediate Similarity	NPC477103
0.7207	Intermediate Similarity	NPC193741
0.7203	Intermediate Similarity	NPC27363
0.72	Intermediate Similarity	NPC470009
0.7196	Intermediate Similarity	NPC86077
0.7196	Intermediate Similarity	NPC475956
0.7196	Intermediate Similarity	NPC252242
0.7196	Intermediate Similarity	NPC470972
0.7196	Intermediate Similarity	NPC154452
0.7193	Intermediate Similarity	NPC471816
0.7184	Intermediate Similarity	NPC281775
0.7184	Intermediate Similarity	NPC477345
0.7184	Intermediate Similarity	NPC238264
0.7184	Intermediate Similarity	NPC477348
0.7182	Intermediate Similarity	NPC38948

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 NPC474182 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	2501
0.2-0.3	4043
0.3-0.4	1615
0.4-0.5	422
0.5-0.6	281
0.6-0.7	38
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
0.7664	Intermediate Similarity	NPD6686	Approved
0.7368	Intermediate Similarity	NPD7328	Approved
0.7368	Intermediate Similarity	NPD7327	Approved
0.7364	Intermediate Similarity	NPD6371	Approved
0.7328	Intermediate Similarity	NPD7503	Approved
0.7304	Intermediate Similarity	NPD7516	Approved
0.7241	Intermediate Similarity	NPD8377	Approved
0.7241	Intermediate Similarity	NPD8294	Approved
0.7179	Intermediate Similarity	NPD8380	Approved
0.7179	Intermediate Similarity	NPD8335	Approved
0.7179	Intermediate Similarity	NPD8379	Approved
0.7179	Intermediate Similarity	NPD8378	Approved
0.7179	Intermediate Similarity	NPD8296	Approved
0.7179	Intermediate Similarity	NPD8033	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.7059	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD7838	Discovery
0.7059	Intermediate Similarity	NPD46	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.6916	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7319	Approved
0.687	Remote Similarity	NPD8133	Approved
0.6789	Remote Similarity	NPD5344	Discontinued
0.6786	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7638	Approved
0.6545	Remote Similarity	NPD7639	Approved
0.6545	Remote Similarity	NPD7640	Approved
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4225	Approved
0.6417	Remote Similarity	NPD7115	Discovery
0.641	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6648	Approved
0.6356	Remote Similarity	NPD6053	Discontinued
0.6321	Remote Similarity	NPD1695	Approved
0.6299	Remote Similarity	NPD7736	Approved
0.629	Remote Similarity	NPD6370	Approved
0.6286	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8293	Discontinued
0.621	Remote Similarity	NPD8513	Phase 3
0.621	Remote Similarity	NPD8516	Approved
0.621	Remote Similarity	NPD8515	Approved
0.621	Remote Similarity	NPD8517	Approved
0.6204	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD7492	Approved
0.6182	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6009	Approved
0.6142	Remote Similarity	NPD6616	Approved
0.6129	Remote Similarity	NPD6054	Approved
0.6111	Remote Similarity	NPD7830	Approved
0.6111	Remote Similarity	NPD7642	Approved
0.6111	Remote Similarity	NPD7829	Approved
0.6111	Remote Similarity	NPD5785	Approved
0.6094	Remote Similarity	NPD7078	Approved
0.6083	Remote Similarity	NPD6882	Approved
0.6058	Remote Similarity	NPD6695	Phase 3
0.6033	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD8171	Discontinued
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.5984	Remote Similarity	NPD8328	Phase 3
0.5984	Remote Similarity	NPD7604	Phase 2
0.5981	Remote Similarity	NPD4251	Approved
0.5981	Remote Similarity	NPD4250	Approved
0.5966	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6016	Approved
0.5952	Remote Similarity	NPD6015	Approved
0.595	Remote Similarity	NPD8297	Approved
0.5929	Remote Similarity	NPD6084	Phase 2
0.5929	Remote Similarity	NPD6083	Phase 2
0.5922	Remote Similarity	NPD4820	Approved
0.5922	Remote Similarity	NPD4822	Approved
0.5922	Remote Similarity	NPD4819	Approved
0.5922	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4821	Approved
0.5917	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7983	Approved
0.5906	Remote Similarity	NPD5988	Approved
0.5905	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD3669	Approved
0.5897	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4249	Approved
0.5887	Remote Similarity	NPD7625	Phase 1
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6051	Approved
0.5847	Remote Similarity	NPD6402	Approved
0.5847	Remote Similarity	NPD7128	Approved
0.5847	Remote Similarity	NPD6675	Approved
0.5847	Remote Similarity	NPD5739	Approved
0.584	Remote Similarity	NPD7641	Discontinued
0.5833	Remote Similarity	NPD7750	Discontinued
0.5816	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5209	Approved
0.581	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5282	Discontinued
0.5798	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6883	Approved
0.5785	Remote Similarity	NPD7290	Approved
0.5785	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD6930	Phase 2
0.5769	Remote Similarity	NPD6931	Approved
0.5769	Remote Similarity	NPD8451	Approved
0.5755	Remote Similarity	NPD5362	Discontinued
0.5752	Remote Similarity	NPD5695	Phase 3
0.575	Remote Similarity	NPD7320	Approved
0.5738	Remote Similarity	NPD6847	Approved
0.5738	Remote Similarity	NPD8130	Phase 1
0.5738	Remote Similarity	NPD6650	Approved
0.5738	Remote Similarity	NPD6649	Approved
0.5738	Remote Similarity	NPD6869	Approved
0.5738	Remote Similarity	NPD6617	Approved
0.5736	Remote Similarity	NPD6067	Discontinued
0.5728	Remote Similarity	NPD4271	Approved
0.5728	Remote Similarity	NPD4268	Approved
0.5725	Remote Similarity	NPD8448	Approved
0.5725	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD6902	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5703	Remote Similarity	NPD5983	Phase 2
0.5703	Remote Similarity	NPD8444	Approved
0.5702	Remote Similarity	NPD6372	Approved
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5702	Remote Similarity	NPD6014	Approved
0.5702	Remote Similarity	NPD6373	Approved
0.5686	Remote Similarity	NPD6933	Approved
0.568	Remote Similarity	NPD6940	Discontinued
0.5673	Remote Similarity	NPD6929	Approved
0.5672	Remote Similarity	NPD7260	Phase 2
0.5667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5701	Approved
0.566	Remote Similarity	NPD6435	Approved
0.5649	Remote Similarity	NPD6336	Discontinued
0.5649	Remote Similarity	NPD8273	Phase 1
0.5648	Remote Similarity	NPD5363	Approved
0.5644	Remote Similarity	NPD1811	Approved
0.5644	Remote Similarity	NPD1810	Approved
0.5635	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7087	Discontinued
0.562	Remote Similarity	NPD6011	Approved
0.5619	Remote Similarity	NPD6928	Phase 2
0.5619	Remote Similarity	NPD7514	Phase 3
0.5607	Remote Similarity	NPD5332	Approved
0.5607	Remote Similarity	NPD7154	Phase 3
0.5607	Remote Similarity	NPD5331	Approved
0.5603	Remote Similarity	NPD5696	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