NPASS Compound

Structure

NPC471169 OpenBabel07101719512D 43 47 0 0 1 0 0 0 0 0999 V2000 3.9952 -4.2831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5425 -6.4281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1049 -0.3822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2120 -5.2968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2869 -2.2739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7973 -3.1218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7395 -3.2446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5766 -2.4277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1557 -5.7009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7417 -5.2289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4597 -0.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8430 -1.0690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6117 -1.2947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5354 -1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9449 -0.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4597 -3.7426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1237 -2.4807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7959 -5.4823 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4125 -1.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4654 -4.3510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9706 -1.5136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -1.0690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4597 -2.7634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3077 -1.2947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9778 0.0512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3077 -4.2322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6659 -2.0204 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0264 -2.7128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9722 -2.4594 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1036 -4.7899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3077 -2.2739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6117 -2.2739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2257 -1.5136 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5333 -0.8212 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4112 -4.0976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1557 -0.8051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1557 -3.7426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1578 -5.0434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3077 -5.2114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0908 -2.6339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2270 -3.6586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3570 -3.8441 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 10 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 4 20 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 8 33 1 0 0 0 0 9 39 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 24 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 32 1 0 0 0 0 14 40 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 17 40 1 0 0 0 0 18 30 1 0 0 0 0 20 35 2 0 0 0 0 20 41 1 0 0 0 0 21 22 1 0 0 0 0 22 33 1 1 0 0 0 23 31 1 0 0 0 0 23 32 1 1 0 0 0 24 31 1 0 0 0 0 24 36 2 0 0 0 0 25 34 1 1 0 0 0 25 43 1 0 0 0 0 26 37 2 0 0 0 0 26 39 1 0 0 0 0 27 19 1 6 0 0 0 27 28 1 0 0 0 0 27 32 1 0 0 0 0 28 29 1 0 0 0 0 28 41 1 6 0 0 0 29 33 1 1 0 0 0 29 42 1 0 0 0 0 30 38 2 0 0 0 0 30 42 1 0 0 0 0 32 7 1 1 0 0 0 33 34 1 1 0 0 0 34 19 1 1 0 0 0 34 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.3
Volume:	611.858
LogP:	4.309
LogD:	3.496
LogS:	-5.43
# Rotatable Bonds:	11
TPSA:	121.64
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.169
Synthetic Accessibility Score:	5.926
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.325
MDCK Permeability:	3.78074255422689e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.763
30% Bioavailability (F30%):	0.565

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	79.68339538574219%
Volume Distribution (VD):	2.392
Pgp-substrate:	13.708911895751953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.41
CYP2C19-substrate:	0.384
CYP2C9-inhibitor:	0.919
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.26
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.788

ADMET: Excretion

Clearance (CL):	9.265
Half-life (T1/2):	0.258

ADMET: Toxicity

hERG Blockers:	0.836
Human Hepatotoxicity (H-HT):	0.914
Drug-inuced Liver Injury (DILI):	0.362
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.097
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC471169

Natural Product ID:	NPC471169
*Common Name:**	12-Deacetoxy-12-(2-Methylbutanoxyl)Toonacilin
IUPAC Name:	[(1aR,3S,3aR,4R,5R,6R,7aS)-5-acetyloxy-3-(furan-3-yl)-6-[(1S,6R)-6-(2-methoxy-2-oxoethyl)-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-methylbutanoate
Synonyms:
Standard InCHIKey:	DONYQPIDLOHRDV-NAQGJSFCSA-N
Standard InCHI:	InChI=1S/C34H44O9/c1-10-18(2)30(38)42-29-28(41-20(4)35)27(32(7)13-11-24(36)31(5,6)23(32)16-26(37)39-9)19(3)34-25(43-34)15-22(33(29,34)8)21-12-14-40-17-21/h11-14,17-18,22-23,25,27-29H,3,10,15-16H2,1-2,4-9H3/t18?,22-,23-,25+,27+,28+,29-,32-,33+,34+/m0/s1
SMILES:	CCC(C(=O)O[C@H]1[C@H](OC(=O)C)[C@@H](C(=C)[C@@]23[C@]1(C)[C@@H](C[C@H]3O2)c1cocc1)[C@@]1(C)C=CC(=O)C([C@@H]1CC(=O)OC)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386295
PubChem CID:	71725940
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[465049]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[465049]

☑ 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 NPC471169 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	411
0.1-0.2	1487
0.2-0.3	3441
0.3-0.4	6370
0.4-0.5	11476
0.5-0.6	10321
0.6-0.7	7995
0.7-0.8	928
0.8-0.85	209
0.85-0.9	46
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC175964
0.9932	High Similarity	NPC471175
0.9605	High Similarity	NPC5741
0.9477	High Similarity	NPC471166
0.9477	High Similarity	NPC471167
0.94	High Similarity	NPC84063
0.929	High Similarity	NPC471168
0.9167	High Similarity	NPC472669
0.9103	High Similarity	NPC472668
0.8987	High Similarity	NPC259943
0.8974	High Similarity	NPC474932
0.8889	High Similarity	NPC469848
0.8831	High Similarity	NPC116717
0.8765	High Similarity	NPC472650
0.8758	High Similarity	NPC476224
0.8742	High Similarity	NPC197596
0.8726	High Similarity	NPC204663
0.869	High Similarity	NPC242068
0.869	High Similarity	NPC247563
0.8684	High Similarity	NPC34056
0.8671	High Similarity	NPC469847
0.8671	High Similarity	NPC195131
0.8654	High Similarity	NPC322546
0.8654	High Similarity	NPC29695
0.8654	High Similarity	NPC182427
0.8654	High Similarity	NPC308205
0.8642	High Similarity	NPC472764
0.8606	High Similarity	NPC471632
0.859	High Similarity	NPC291150
0.859	High Similarity	NPC18135
0.8589	High Similarity	NPC327922
0.8589	High Similarity	NPC472765
0.8589	High Similarity	NPC472766
0.858	High Similarity	NPC105395
0.8571	High Similarity	NPC255414
0.8571	High Similarity	NPC476197
0.8553	High Similarity	NPC167142
0.8553	High Similarity	NPC470118
0.8553	High Similarity	NPC197137
0.8544	High Similarity	NPC469850
0.8535	High Similarity	NPC268905
0.8526	High Similarity	NPC5180
0.8509	High Similarity	NPC472767
0.8509	High Similarity	NPC6326
0.8503	High Similarity	NPC478177
0.8494	Intermediate Similarity	NPC94763
0.8494	Intermediate Similarity	NPC477824
0.8485	Intermediate Similarity	NPC285227
0.8476	Intermediate Similarity	NPC242334
0.8462	Intermediate Similarity	NPC470790
0.8462	Intermediate Similarity	NPC470791
0.8462	Intermediate Similarity	NPC69647
0.8462	Intermediate Similarity	NPC471001
0.8462	Intermediate Similarity	NPC125182
0.8457	Intermediate Similarity	NPC165218
0.8438	Intermediate Similarity	NPC214495
0.8438	Intermediate Similarity	NPC475066
0.8438	Intermediate Similarity	NPC470119
0.8428	Intermediate Similarity	NPC476262
0.8428	Intermediate Similarity	NPC92979
0.8424	Intermediate Similarity	NPC472659
0.8418	Intermediate Similarity	NPC472672
0.8415	Intermediate Similarity	NPC173516
0.8408	Intermediate Similarity	NPC156189
0.8395	Intermediate Similarity	NPC96443
0.8395	Intermediate Similarity	NPC470939
0.8395	Intermediate Similarity	NPC290400
0.8393	Intermediate Similarity	NPC470181
0.8387	Intermediate Similarity	NPC471292
0.8385	Intermediate Similarity	NPC475226
0.8385	Intermediate Similarity	NPC473473
0.8385	Intermediate Similarity	NPC472671
0.8385	Intermediate Similarity	NPC475295
0.8383	Intermediate Similarity	NPC236004
0.8365	Intermediate Similarity	NPC302054
0.8365	Intermediate Similarity	NPC253201
0.8364	Intermediate Similarity	NPC160651
0.8364	Intermediate Similarity	NPC472673
0.8364	Intermediate Similarity	NPC471397
0.8354	Intermediate Similarity	NPC149945
0.8354	Intermediate Similarity	NPC478178
0.8344	Intermediate Similarity	NPC472139
0.8344	Intermediate Similarity	NPC469846
0.8333	Intermediate Similarity	NPC167340
0.8333	Intermediate Similarity	NPC221809
0.8333	Intermediate Similarity	NPC469633
0.8333	Intermediate Similarity	NPC191828
0.8323	Intermediate Similarity	NPC286722
0.8323	Intermediate Similarity	NPC195954
0.8323	Intermediate Similarity	NPC472283
0.8313	Intermediate Similarity	NPC264943
0.8303	Intermediate Similarity	NPC476850
0.8303	Intermediate Similarity	NPC476861
0.8303	Intermediate Similarity	NPC478179
0.8302	Intermediate Similarity	NPC476201
0.8293	Intermediate Similarity	NPC469849
0.8293	Intermediate Similarity	NPC476856
0.8293	Intermediate Similarity	NPC476858
0.8293	Intermediate Similarity	NPC476857
0.8291	Intermediate Similarity	NPC469335
0.8291	Intermediate Similarity	NPC159927
0.8282	Intermediate Similarity	NPC472771
0.8282	Intermediate Similarity	NPC470792
0.8274	Intermediate Similarity	NPC471437
0.8274	Intermediate Similarity	NPC469576
0.8272	Intermediate Similarity	NPC237155
0.8269	Intermediate Similarity	NPC470999
0.8263	Intermediate Similarity	NPC159232
0.8261	Intermediate Similarity	NPC60973
0.8261	Intermediate Similarity	NPC209364
0.8258	Intermediate Similarity	NPC199044
0.8258	Intermediate Similarity	NPC238843
0.8247	Intermediate Similarity	NPC121158
0.8242	Intermediate Similarity	NPC470875
0.8235	Intermediate Similarity	NPC56197
0.8232	Intermediate Similarity	NPC14499
0.8232	Intermediate Similarity	NPC469338
0.8232	Intermediate Similarity	NPC663
0.8232	Intermediate Similarity	NPC224394
0.8232	Intermediate Similarity	NPC476035
0.8232	Intermediate Similarity	NPC292389
0.8232	Intermediate Similarity	NPC475039
0.8232	Intermediate Similarity	NPC472773
0.8228	Intermediate Similarity	NPC329180
0.8221	Intermediate Similarity	NPC472653
0.8221	Intermediate Similarity	NPC470789
0.8221	Intermediate Similarity	NPC305016
0.8221	Intermediate Similarity	NPC25255
0.8217	Intermediate Similarity	NPC471174
0.821	Intermediate Similarity	NPC88007
0.821	Intermediate Similarity	NPC299038
0.8205	Intermediate Similarity	NPC5676
0.8204	Intermediate Similarity	NPC470995
0.8199	Intermediate Similarity	NPC141538
0.8199	Intermediate Similarity	NPC155939
0.8199	Intermediate Similarity	NPC296807
0.8194	Intermediate Similarity	NPC80635
0.8193	Intermediate Similarity	NPC472774
0.8193	Intermediate Similarity	NPC472282
0.8193	Intermediate Similarity	NPC473753
0.8193	Intermediate Similarity	NPC473766
0.8193	Intermediate Similarity	NPC472775
0.8193	Intermediate Similarity	NPC476853
0.8187	Intermediate Similarity	NPC75906
0.8187	Intermediate Similarity	NPC33938
0.8187	Intermediate Similarity	NPC470996
0.8187	Intermediate Similarity	NPC471002
0.8182	Intermediate Similarity	NPC62692
0.8182	Intermediate Similarity	NPC61967
0.8182	Intermediate Similarity	NPC27541
0.8182	Intermediate Similarity	NPC123088
0.8182	Intermediate Similarity	NPC476860
0.8182	Intermediate Similarity	NPC276551
0.8182	Intermediate Similarity	NPC126984
0.8182	Intermediate Similarity	NPC470940
0.8176	Intermediate Similarity	NPC476122
0.8176	Intermediate Similarity	NPC477404
0.8176	Intermediate Similarity	NPC470997
0.8176	Intermediate Similarity	NPC196864
0.8171	Intermediate Similarity	NPC68848
0.8171	Intermediate Similarity	NPC193798
0.8171	Intermediate Similarity	NPC329938
0.8171	Intermediate Similarity	NPC117986
0.8171	Intermediate Similarity	NPC149896
0.816	Intermediate Similarity	NPC477403
0.8148	Intermediate Similarity	NPC126723
0.8148	Intermediate Similarity	NPC107646
0.8148	Intermediate Similarity	NPC263265
0.8141	Intermediate Similarity	NPC251865
0.8137	Intermediate Similarity	NPC57998
0.8137	Intermediate Similarity	NPC98206
0.8137	Intermediate Similarity	NPC237259
0.8137	Intermediate Similarity	NPC34421
0.8133	Intermediate Similarity	NPC472141
0.8133	Intermediate Similarity	NPC307781
0.8133	Intermediate Similarity	NPC23387
0.8133	Intermediate Similarity	NPC472670
0.8125	Intermediate Similarity	NPC272590
0.8125	Intermediate Similarity	NPC471000
0.8121	Intermediate Similarity	NPC285567
0.8121	Intermediate Similarity	NPC234660
0.8121	Intermediate Similarity	NPC51568
0.8113	Intermediate Similarity	NPC234494
0.8113	Intermediate Similarity	NPC472654
0.811	Intermediate Similarity	NPC477402
0.811	Intermediate Similarity	NPC475381
0.8101	Intermediate Similarity	NPC216755
0.8101	Intermediate Similarity	NPC71821
0.8098	Intermediate Similarity	NPC472778
0.8098	Intermediate Similarity	NPC472772
0.8098	Intermediate Similarity	NPC472777
0.8098	Intermediate Similarity	NPC173544
0.8098	Intermediate Similarity	NPC187149
0.8098	Intermediate Similarity	NPC472776
0.8098	Intermediate Similarity	NPC194499
0.8095	Intermediate Similarity	NPC88593
0.8086	Intermediate Similarity	NPC469336
0.8084	Intermediate Similarity	NPC270312
0.8081	Intermediate Similarity	NPC470938
0.8077	Intermediate Similarity	NPC223415

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 NPC471169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	1053
0.2-0.3	2344
0.3-0.4	2727
0.4-0.5	1735
0.5-0.6	774
0.6-0.7	173
0.7-0.8	9
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
0.7975	Intermediate Similarity	NPD5761	Phase 2
0.7975	Intermediate Similarity	NPD5760	Phase 2
0.7784	Intermediate Similarity	NPD8434	Phase 2
0.7701	Intermediate Similarity	NPD6765	Approved
0.7701	Intermediate Similarity	NPD6764	Approved
0.7679	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6784	Approved
0.7528	Intermediate Similarity	NPD6785	Approved
0.7086	Intermediate Similarity	NPD8127	Discontinued
0.7049	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4628	Phase 3
0.6946	Remote Similarity	NPD7236	Approved
0.6936	Remote Similarity	NPD7819	Suspended
0.6923	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD7685	Pre-registration
0.6889	Remote Similarity	NPD7799	Discontinued
0.686	Remote Similarity	NPD6599	Discontinued
0.6856	Remote Similarity	NPD7497	Discontinued
0.6842	Remote Similarity	NPD7239	Suspended
0.6836	Remote Similarity	NPD5494	Approved
0.6824	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD1247	Approved
0.6784	Remote Similarity	NPD920	Approved
0.678	Remote Similarity	NPD919	Approved
0.6766	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5844	Phase 1
0.6743	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8032	Phase 2
0.6726	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7075	Discontinued
0.6705	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.67	Remote Similarity	NPD8404	Phase 2
0.6667	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6005	Phase 3
0.6647	Remote Similarity	NPD5763	Approved
0.6647	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5762	Approved
0.6647	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6004	Phase 3
0.6647	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6002	Phase 3
0.6629	Remote Similarity	NPD7411	Suspended
0.6627	Remote Similarity	NPD3748	Approved
0.6612	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7199	Phase 2
0.661	Remote Similarity	NPD3817	Phase 2
0.6609	Remote Similarity	NPD3226	Approved
0.6608	Remote Similarity	NPD6799	Approved
0.6591	Remote Similarity	NPD6801	Discontinued
0.659	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2796	Approved
0.6573	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7028	Phase 2
0.657	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6559	Discontinued
0.6557	Remote Similarity	NPD7473	Discontinued
0.6548	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1471	Phase 3
0.6538	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4107	Approved
0.6514	Remote Similarity	NPD7458	Discontinued
0.651	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8285	Discontinued
0.648	Remote Similarity	NPD7058	Phase 2
0.648	Remote Similarity	NPD7057	Phase 3
0.6471	Remote Similarity	NPD1243	Approved
0.6461	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6355	Discontinued
0.6442	Remote Similarity	NPD6832	Phase 2
0.6433	Remote Similarity	NPD4110	Phase 3
0.6433	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3750	Approved
0.6425	Remote Similarity	NPD5402	Approved
0.6414	Remote Similarity	NPD4482	Phase 3
0.6407	Remote Similarity	NPD6653	Approved
0.6406	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1934	Approved
0.6402	Remote Similarity	NPD8312	Approved
0.6402	Remote Similarity	NPD8313	Approved
0.6398	Remote Similarity	NPD1876	Approved
0.6395	Remote Similarity	NPD3887	Approved
0.6393	Remote Similarity	NPD6232	Discontinued
0.6392	Remote Similarity	NPD17	Approved
0.6391	Remote Similarity	NPD2438	Suspended
0.6391	Remote Similarity	NPD6100	Approved
0.6391	Remote Similarity	NPD6099	Approved
0.6389	Remote Similarity	NPD4966	Approved
0.6389	Remote Similarity	NPD4965	Approved
0.6389	Remote Similarity	NPD4967	Phase 2
0.6387	Remote Similarity	NPD8150	Discontinued
0.6386	Remote Similarity	NPD4140	Approved
0.6384	Remote Similarity	NPD4380	Phase 2
0.6383	Remote Similarity	NPD8368	Discontinued
0.6379	Remote Similarity	NPD2534	Approved
0.6379	Remote Similarity	NPD2532	Approved
0.6379	Remote Similarity	NPD2533	Approved
0.6375	Remote Similarity	NPD3972	Approved
0.6368	Remote Similarity	NPD8407	Phase 2
0.6364	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3926	Phase 2
0.6358	Remote Similarity	NPD3267	Approved
0.6358	Remote Similarity	NPD3266	Approved
0.6354	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3751	Discontinued
0.6344	Remote Similarity	NPD3818	Discontinued
0.6335	Remote Similarity	NPD5327	Phase 3
0.6333	Remote Similarity	NPD5353	Approved
0.6331	Remote Similarity	NPD2799	Discontinued
0.633	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD2403	Approved
0.6322	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6234	Discontinued
0.6316	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD37	Approved
0.631	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD5403	Approved
0.6298	Remote Similarity	NPD3882	Suspended
0.6298	Remote Similarity	NPD7768	Phase 2
0.6294	Remote Similarity	NPD1551	Phase 2
0.6286	Remote Similarity	NPD5401	Approved
0.6286	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2800	Approved
0.6278	Remote Similarity	NPD2801	Approved
0.6277	Remote Similarity	NPD7074	Phase 3
0.6273	Remote Similarity	NPD1608	Approved
0.6265	Remote Similarity	NPD3268	Approved
0.6264	Remote Similarity	NPD3749	Approved
0.6257	Remote Similarity	NPD6386	Approved
0.6257	Remote Similarity	NPD2346	Discontinued
0.6257	Remote Similarity	NPD6385	Approved
0.6256	Remote Similarity	NPD7907	Approved
0.625	Remote Similarity	NPD6959	Discontinued
0.625	Remote Similarity	NPD5735	Approved
0.625	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8166	Discontinued
0.6237	Remote Similarity	NPD6166	Phase 2
0.6237	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD7033	Discontinued
0.6228	Remote Similarity	NPD6663	Approved
0.6226	Remote Similarity	NPD5585	Approved
0.6223	Remote Similarity	NPD7054	Approved
0.6223	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD1549	Phase 2
0.622	Remote Similarity	NPD5647	Approved
0.6216	Remote Similarity	NPD7315	Approved
0.6216	Remote Similarity	NPD3787	Discontinued
0.6216	Remote Similarity	NPD6808	Phase 2
0.6213	Remote Similarity	NPD6353	Approved
0.6199	Remote Similarity	NPD2935	Discontinued
0.6193	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2979	Phase 3
0.619	Remote Similarity	NPD7472	Approved
0.619	Remote Similarity	NPD4307	Phase 2
0.6188	Remote Similarity	NPD8455	Phase 2
0.6188	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD1465	Phase 2
0.6183	Remote Similarity	NPD5242	Approved
0.6178	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7808	Phase 3
0.6173	Remote Similarity	NPD7507	Approved
0.6171	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7228	Approved
0.6163	Remote Similarity	NPD2353	Approved
0.6163	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4111	Phase 1
0.6159	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD6008	Approved
0.6159	Remote Similarity	NPD7319	Approved
0.6159	Remote Similarity	NPD6362	Approved
0.6154	Remote Similarity	NPD8360	Approved
0.6154	Remote Similarity	NPD1241	Discontinued
0.6154	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8435	Approved
0.6154	Remote Similarity	NPD8361	Approved
0.6149	Remote Similarity	NPD7003	Approved
0.6143	Remote Similarity	NPD5980	Discovery
0.6139	Remote Similarity	NPD3057	Approved
0.6134	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7229	Phase 3
0.6127	Remote Similarity	NPD7999	Approved
0.6126	Remote Similarity	NPD7251	Discontinued
0.6118	Remote Similarity	NPD6651	Approved
0.6114	Remote Similarity	NPD6190	Approved
0.6108	Remote Similarity	NPD7435	Discontinued
0.6098	Remote Similarity	NPD8651	Approved
0.6087	Remote Similarity	NPD1778	Approved
0.6085	Remote Similarity	NPD4665	Approved
0.6084	Remote Similarity	NPD5736	Approved
0.6082	Remote Similarity	NPD7097	Phase 1
0.6077	Remote Similarity	NPD6873	Phase 2
0.6073	Remote Similarity	NPD6797	Phase 2
0.6071	Remote Similarity	NPD2313	Discontinued
0.6071	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5616	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