NPASS Compound

Structure

NPC470181 OpenBabel07101719132D 50 57 0 0 1 0 0 0 0 0999 V2000 -2.0585 -2.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5376 -3.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3388 0.8373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4082 0.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3867 -0.7436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7219 1.7678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5723 -1.2403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5490 4.3409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1357 0.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5592 0.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9341 0.8166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0946 1.0419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9341 -1.3488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9288 -0.5356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9018 2.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0692 0.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3485 -3.1117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7557 -2.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5969 -0.1084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0332 -0.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9341 -0.6270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5592 -1.7097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1251 2.1731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1843 -0.6270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4779 0.6034 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0527 -0.9292 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2553 -0.7161 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5592 -0.2661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5827 -0.1827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2553 0.9057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2661 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.4557 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8837 0.4219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3090 -0.2661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9590 -0.5555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5790 -4.0645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 -2.0497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5450 -0.3577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5592 -2.6900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2188 2.5468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7723 3.7429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5847 0.1929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4082 -2.8348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0371 -1.6719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1843 -1.3488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2547 1.2014 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9070 -0.8048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2056 -0.0652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7509 -0.0923 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 6 30 1 0 0 0 0 8 41 1 0 0 0 0 9 12 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 28 1 0 0 0 0 11 32 1 0 0 0 0 12 42 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 20 2 0 0 0 0 14 42 1 0 0 0 0 15 23 1 0 0 0 0 15 41 1 0 0 0 0 16 29 1 0 0 0 0 16 33 1 0 0 0 0 17 36 2 0 0 0 0 17 43 1 0 0 0 0 18 37 2 0 0 0 0 18 44 1 0 0 0 0 19 38 2 0 0 0 0 19 47 1 0 0 0 0 20 24 1 0 0 0 0 21 28 1 6 0 0 0 21 34 1 0 0 0 0 22 39 2 0 0 0 0 22 45 1 0 0 0 0 23 40 2 0 0 0 0 23 46 1 0 0 0 0 24 28 1 1 0 0 0 24 45 1 0 0 0 0 25 29 1 6 0 0 0 25 30 1 0 0 0 0 25 46 1 0 0 0 0 26 29 1 1 0 0 0 26 35 1 0 0 0 0 26 43 1 0 0 0 0 27 34 1 6 0 0 0 27 35 1 0 0 0 0 27 44 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 6 0 0 0 30 32 1 6 0 0 0 31 7 1 1 0 0 0 31 48 1 0 0 0 0 31 49 1 0 0 0 0 31 50 1 0 0 0 0 32 34 1 6 0 0 0 32 48 1 0 0 0 0 33 30 1 6 0 0 0 33 49 1 0 0 0 0 34 50 1 1 0 0 0 35 33 1 6 0 0 0 35 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	702.25
Volume:	658.862
LogP:	2.208
LogD:	1.664
LogS:	-5.044
# Rotatable Bonds:	11
TPSA:	181.56
# H-Bond Aceptor:	15
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.299
Synthetic Accessibility Score:	7.748
Fsp3:	0.743
Lipinski Rule-of-5:	Rejected
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:	-5.357
MDCK Permeability:	0.00010510655556572601
Pgp-inhibitor:	0.999
Pgp-substrate:	0.71
Human Intestinal Absorption (HIA):	0.103
20% Bioavailability (F20%):	0.744
30% Bioavailability (F30%):	0.161

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.522
Plasma Protein Binding (PPB):	59.636199951171875%
Volume Distribution (VD):	1.295
Pgp-substrate:	26.789899826049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.818
CYP3A4-substrate:	0.883

ADMET: Excretion

Clearance (CL):	1.29
Half-life (T1/2):	0.284

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.991
Rat Oral Acute Toxicity:	0.999
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.576
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.067
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC470181

Natural Product ID:	NPC470181
*Common Name:**	Xyloccensin E
IUPAC Name:	n.a.
Synonyms:	Xyloccensin E
Standard InCHIKey:	HBXWLQXJFYLQHO-OPSRHREQSA-N
Standard InCHI:	InChI=1S/C35H42O15/c1-17(36)43-26-29(5)16-33-30(6,25(29)46-23(40)15-41-8)32-11-10-28(4)21(13-22(39)45-24(28)20-9-12-42-14-20)34(32,50-31(7,48-32)49-33)27(44-18(2)37)35(26,33)47-19(3)38/h9,12,14,21,24-27H,10-11,13,15-16H2,1-8H3/t21-,24+,25+,26+,27-,28-,29-,30-,31+,32+,33-,34-,35+/m1/s1
SMILES:	CC(=O)OC1C2(CC34C1(C(C56C7CC(=O)OC(C7(CCC5(C3(C2OC(=O)COC)C)OC(O4)(O6)C)C)C8=COC=C8)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1808138
PubChem CID:	56680327
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO6445	Xylocarpus moluccensis	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	27000.0	nM	PMID[525728]

☑ 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 NPC470181 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	525
0.1-0.2	1911
0.2-0.3	3938
0.3-0.4	7704
0.4-0.5	11151
0.5-0.6	11169
0.6-0.7	5496
0.7-0.8	641
0.8-0.85	125
0.85-0.9	33
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9755	High Similarity	NPC477824
0.9273	High Similarity	NPC327922
0.9176	High Similarity	NPC470938
0.8941	High Similarity	NPC236004
0.8941	High Similarity	NPC94763
0.8802	High Similarity	NPC472139
0.878	High Similarity	NPC476262
0.8757	High Similarity	NPC476224
0.8728	High Similarity	NPC478177
0.8698	High Similarity	NPC478178
0.8693	High Similarity	NPC242068
0.8693	High Similarity	NPC247563
0.8693	High Similarity	NPC105395
0.869	High Similarity	NPC469846
0.8671	High Similarity	NPC469633
0.8663	High Similarity	NPC469848
0.8659	High Similarity	NPC476201
0.8613	High Similarity	NPC469576
0.8605	High Similarity	NPC159232
0.858	High Similarity	NPC165218
0.858	High Similarity	NPC472669
0.8547	High Similarity	NPC82602
0.8537	High Similarity	NPC476122
0.8521	High Similarity	NPC471166
0.8521	High Similarity	NPC471167
0.8521	High Similarity	NPC6326
0.8521	High Similarity	NPC82851
0.8521	High Similarity	NPC117986
0.8521	High Similarity	NPC472668
0.8512	High Similarity	NPC475295
0.8512	High Similarity	NPC473473
0.8506	High Similarity	NPC471437
0.8497	Intermediate Similarity	NPC160818
0.8497	Intermediate Similarity	NPC285227
0.8497	Intermediate Similarity	NPC169299
0.8488	Intermediate Similarity	NPC242334
0.848	Intermediate Similarity	NPC97574
0.848	Intermediate Similarity	NPC472141
0.848	Intermediate Similarity	NPC93172
0.8471	Intermediate Similarity	NPC471168
0.8462	Intermediate Similarity	NPC472653
0.8452	Intermediate Similarity	NPC472283
0.8452	Intermediate Similarity	NPC286722
0.8439	Intermediate Similarity	NPC472650
0.8434	Intermediate Similarity	NPC84063
0.843	Intermediate Similarity	NPC478179
0.8421	Intermediate Similarity	NPC470182
0.8412	Intermediate Similarity	NPC200782
0.8412	Intermediate Similarity	NPC470939
0.8412	Intermediate Similarity	NPC96443
0.8412	Intermediate Similarity	NPC290400
0.8393	Intermediate Similarity	NPC126723
0.8393	Intermediate Similarity	NPC471169
0.8393	Intermediate Similarity	NPC175964
0.8393	Intermediate Similarity	NPC107646
0.8393	Intermediate Similarity	NPC209364
0.8382	Intermediate Similarity	NPC271235
0.8372	Intermediate Similarity	NPC214600
0.8363	Intermediate Similarity	NPC39986
0.8363	Intermediate Similarity	NPC134254
0.8363	Intermediate Similarity	NPC302369
0.8353	Intermediate Similarity	NPC475381
0.8353	Intermediate Similarity	NPC191828
0.8353	Intermediate Similarity	NPC305016
0.8352	Intermediate Similarity	NPC262386
0.8343	Intermediate Similarity	NPC167142
0.8343	Intermediate Similarity	NPC249021
0.8343	Intermediate Similarity	NPC195131
0.8333	Intermediate Similarity	NPC472659
0.8333	Intermediate Similarity	NPC471175
0.8324	Intermediate Similarity	NPC472764
0.8323	Intermediate Similarity	NPC322546
0.8323	Intermediate Similarity	NPC308205
0.8314	Intermediate Similarity	NPC271657
0.8314	Intermediate Similarity	NPC469849
0.8314	Intermediate Similarity	NPC259943
0.8304	Intermediate Similarity	NPC197596
0.8304	Intermediate Similarity	NPC18347
0.8304	Intermediate Similarity	NPC149896
0.8294	Intermediate Similarity	NPC475967
0.8294	Intermediate Similarity	NPC474932
0.8294	Intermediate Similarity	NPC475226
0.8284	Intermediate Similarity	NPC204663
0.8276	Intermediate Similarity	NPC472765
0.8276	Intermediate Similarity	NPC472652
0.8276	Intermediate Similarity	NPC472766
0.8276	Intermediate Similarity	NPC160651
0.8276	Intermediate Similarity	NPC472673
0.8274	Intermediate Similarity	NPC282445
0.8266	Intermediate Similarity	NPC149945
0.8266	Intermediate Similarity	NPC470875
0.8263	Intermediate Similarity	NPC18135
0.8256	Intermediate Similarity	NPC419
0.8256	Intermediate Similarity	NPC234660
0.8256	Intermediate Similarity	NPC469338
0.8256	Intermediate Similarity	NPC51568
0.8256	Intermediate Similarity	NPC292389
0.8256	Intermediate Similarity	NPC477405
0.8256	Intermediate Similarity	NPC476197
0.8246	Intermediate Similarity	NPC335761
0.8218	Intermediate Similarity	NPC476861
0.8218	Intermediate Similarity	NPC472775
0.8218	Intermediate Similarity	NPC100333
0.8218	Intermediate Similarity	NPC472774
0.8218	Intermediate Similarity	NPC472651
0.8218	Intermediate Similarity	NPC173516
0.8218	Intermediate Similarity	NPC476850
0.8214	Intermediate Similarity	NPC29695
0.8214	Intermediate Similarity	NPC182427
0.8208	Intermediate Similarity	NPC470940
0.8208	Intermediate Similarity	NPC476857
0.8208	Intermediate Similarity	NPC476856
0.8208	Intermediate Similarity	NPC276551
0.8208	Intermediate Similarity	NPC476858
0.8204	Intermediate Similarity	NPC477404
0.8204	Intermediate Similarity	NPC196864
0.8198	Intermediate Similarity	NPC211777
0.8198	Intermediate Similarity	NPC5079
0.8198	Intermediate Similarity	NPC207978
0.8192	Intermediate Similarity	NPC471632
0.8187	Intermediate Similarity	NPC237155
0.8187	Intermediate Similarity	NPC307383
0.8176	Intermediate Similarity	NPC60973
0.8171	Intermediate Similarity	NPC471397
0.815	Intermediate Similarity	NPC198047
0.8144	Intermediate Similarity	NPC470791
0.8144	Intermediate Similarity	NPC470790
0.814	Intermediate Similarity	NPC25255
0.814	Intermediate Similarity	NPC470789
0.8133	Intermediate Similarity	NPC470941
0.8129	Intermediate Similarity	NPC299038
0.8129	Intermediate Similarity	NPC261597
0.8129	Intermediate Similarity	NPC36655
0.8129	Intermediate Similarity	NPC45101
0.8129	Intermediate Similarity	NPC470119
0.8129	Intermediate Similarity	NPC469847
0.8129	Intermediate Similarity	NPC214495
0.8125	Intermediate Similarity	NPC470995
0.8118	Intermediate Similarity	NPC469850
0.8118	Intermediate Similarity	NPC44675
0.8118	Intermediate Similarity	NPC214541
0.8114	Intermediate Similarity	NPC472282
0.8114	Intermediate Similarity	NPC476853
0.8114	Intermediate Similarity	NPC473766
0.8114	Intermediate Similarity	NPC473753
0.8107	Intermediate Similarity	NPC469503
0.8103	Intermediate Similarity	NPC123088
0.8103	Intermediate Similarity	NPC476860
0.8095	Intermediate Similarity	NPC469335
0.8095	Intermediate Similarity	NPC159927
0.8095	Intermediate Similarity	NPC156189
0.8092	Intermediate Similarity	NPC5741
0.8092	Intermediate Similarity	NPC470792
0.8092	Intermediate Similarity	NPC329938
0.8092	Intermediate Similarity	NPC69028
0.8092	Intermediate Similarity	NPC472767
0.8092	Intermediate Similarity	NPC472771
0.8092	Intermediate Similarity	NPC193798
0.8081	Intermediate Similarity	NPC477403
0.807	Intermediate Similarity	NPC263265
0.8057	Intermediate Similarity	NPC472670
0.8057	Intermediate Similarity	NPC23387
0.8057	Intermediate Similarity	NPC307781
0.8047	Intermediate Similarity	NPC471000
0.8046	Intermediate Similarity	NPC224394
0.8046	Intermediate Similarity	NPC472773
0.8046	Intermediate Similarity	NPC663
0.8045	Intermediate Similarity	NPC167340
0.8036	Intermediate Similarity	NPC471001
0.8024	Intermediate Similarity	NPC255414
0.8024	Intermediate Similarity	NPC221809
0.8023	Intermediate Similarity	NPC187149
0.8023	Intermediate Similarity	NPC475066
0.8023	Intermediate Similarity	NPC302392
0.8	Intermediate Similarity	NPC61967
0.8	Intermediate Similarity	NPC146991
0.8	Intermediate Similarity	NPC472672
0.7989	Intermediate Similarity	NPC263432
0.7988	Intermediate Similarity	NPC46551
0.7978	Intermediate Similarity	NPC475641
0.7978	Intermediate Similarity	NPC186746
0.7978	Intermediate Similarity	NPC475237
0.7977	Intermediate Similarity	NPC472671
0.7977	Intermediate Similarity	NPC262872
0.7964	Intermediate Similarity	NPC262198
0.7953	Intermediate Similarity	NPC30222
0.7953	Intermediate Similarity	NPC253201
0.7953	Intermediate Similarity	NPC302054
0.7943	Intermediate Similarity	NPC476035
0.7943	Intermediate Similarity	NPC475039
0.7943	Intermediate Similarity	NPC14499
0.7941	Intermediate Similarity	NPC116717
0.7931	Intermediate Similarity	NPC477402
0.7929	Intermediate Similarity	NPC472654
0.7929	Intermediate Similarity	NPC125182
0.7929	Intermediate Similarity	NPC69647
0.7921	Intermediate Similarity	NPC88593
0.7919	Intermediate Similarity	NPC472778
0.7919	Intermediate Similarity	NPC472772
0.7919	Intermediate Similarity	NPC470118

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 NPC470181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	1194
0.2-0.3	2600
0.3-0.4	2848
0.4-0.5	1481
0.5-0.6	485
0.6-0.7	119
0.7-0.8	8
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8118	Intermediate Similarity	NPD5761	Phase 2
0.8118	Intermediate Similarity	NPD5760	Phase 2
0.7634	Intermediate Similarity	NPD8434	Phase 2
0.7627	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6764	Approved
0.7366	Intermediate Similarity	NPD6765	Approved
0.7337	Intermediate Similarity	NPD7799	Discontinued
0.7211	Intermediate Similarity	NPD6784	Approved
0.7211	Intermediate Similarity	NPD6785	Approved
0.7113	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5494	Approved
0.709	Intermediate Similarity	NPD7685	Pre-registration
0.6931	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD7075	Discontinued
0.6898	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8404	Phase 2
0.6851	Remote Similarity	NPD6599	Discontinued
0.6847	Remote Similarity	NPD7497	Discontinued
0.6831	Remote Similarity	NPD7819	Suspended
0.6823	Remote Similarity	NPD6559	Discontinued
0.6791	Remote Similarity	NPD8127	Discontinued
0.6788	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD919	Approved
0.6753	Remote Similarity	NPD8312	Approved
0.6753	Remote Similarity	NPD8313	Approved
0.6742	Remote Similarity	NPD7236	Approved
0.6736	Remote Similarity	NPD7251	Discontinued
0.6718	Remote Similarity	NPD8407	Phase 2
0.6703	Remote Similarity	NPD5402	Approved
0.6703	Remote Similarity	NPD3817	Phase 2
0.6702	Remote Similarity	NPD1247	Approved
0.6702	Remote Similarity	NPD7199	Phase 2
0.6702	Remote Similarity	NPD3751	Discontinued
0.6685	Remote Similarity	NPD6801	Discontinued
0.6684	Remote Similarity	NPD6797	Phase 2
0.6683	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD5844	Phase 1
0.6649	Remote Similarity	NPD8368	Discontinued
0.6648	Remote Similarity	NPD7239	Suspended
0.6632	Remote Similarity	NPD7074	Phase 3
0.6631	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6273	Approved
0.6615	Remote Similarity	NPD3818	Discontinued
0.6615	Remote Similarity	NPD7228	Approved
0.6611	Remote Similarity	NPD6799	Approved
0.6602	Remote Similarity	NPD7698	Approved
0.6602	Remote Similarity	NPD7697	Approved
0.6602	Remote Similarity	NPD7696	Phase 3
0.6593	Remote Similarity	NPD920	Approved
0.6593	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7054	Approved
0.6578	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4967	Phase 2
0.6578	Remote Similarity	NPD4966	Approved
0.6578	Remote Similarity	NPD4965	Approved
0.6571	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7874	Approved
0.6566	Remote Similarity	NPD8150	Discontinued
0.6546	Remote Similarity	NPD7472	Approved
0.6536	Remote Similarity	NPD4628	Phase 3
0.6524	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6166	Phase 2
0.651	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6234	Discontinued
0.6505	Remote Similarity	NPD37	Approved
0.6503	Remote Similarity	NPD5403	Approved
0.65	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD7907	Approved
0.649	Remote Similarity	NPD8320	Phase 1
0.649	Remote Similarity	NPD7870	Phase 2
0.649	Remote Similarity	NPD7871	Phase 2
0.649	Remote Similarity	NPD8319	Approved
0.6489	Remote Similarity	NPD3882	Suspended
0.6486	Remote Similarity	NPD7028	Phase 2
0.6484	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5401	Approved
0.648	Remote Similarity	NPD7240	Approved
0.6477	Remote Similarity	NPD7473	Discontinued
0.6476	Remote Similarity	NPD7701	Phase 2
0.6471	Remote Similarity	NPD7319	Approved
0.6461	Remote Similarity	NPD5763	Approved
0.6461	Remote Similarity	NPD5762	Approved
0.6461	Remote Similarity	NPD1471	Phase 3
0.6458	Remote Similarity	NPD3926	Phase 2
0.6456	Remote Similarity	NPD6776	Approved
0.6456	Remote Similarity	NPD4107	Approved
0.6456	Remote Similarity	NPD6779	Approved
0.6456	Remote Similarity	NPD6778	Approved
0.6456	Remote Similarity	NPD6781	Approved
0.6456	Remote Similarity	NPD6782	Approved
0.6456	Remote Similarity	NPD6780	Approved
0.6456	Remote Similarity	NPD6777	Approved
0.6455	Remote Similarity	NPD3749	Approved
0.6452	Remote Similarity	NPD7411	Suspended
0.6432	Remote Similarity	NPD7458	Discontinued
0.6418	Remote Similarity	NPD8435	Approved
0.641	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6232	Discontinued
0.6404	Remote Similarity	NPD2796	Approved
0.6398	Remote Similarity	NPD4380	Phase 2
0.6385	Remote Similarity	NPD7801	Approved
0.6385	Remote Similarity	NPD7783	Phase 2
0.6385	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8455	Phase 2
0.6383	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1933	Approved
0.6359	Remote Similarity	NPD7699	Phase 2
0.6359	Remote Similarity	NPD7700	Phase 2
0.6354	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6959	Discontinued
0.6353	Remote Similarity	NPD7078	Approved
0.6346	Remote Similarity	NPD4482	Phase 3
0.634	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD8361	Approved
0.6337	Remote Similarity	NPD8360	Approved
0.633	Remote Similarity	NPD1934	Approved
0.6316	Remote Similarity	NPD7736	Approved
0.6316	Remote Similarity	NPD7058	Phase 2
0.6316	Remote Similarity	NPD7768	Phase 2
0.6316	Remote Similarity	NPD7057	Phase 3
0.6307	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD2534	Approved
0.6304	Remote Similarity	NPD2533	Approved
0.6304	Remote Similarity	NPD2532	Approved
0.6304	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1465	Phase 2
0.6294	Remote Similarity	NPD7507	Approved
0.6291	Remote Similarity	NPD8151	Discontinued
0.6278	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6004	Phase 3
0.6278	Remote Similarity	NPD6002	Phase 3
0.6278	Remote Similarity	NPD6005	Phase 3
0.6276	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6355	Discontinued
0.6264	Remote Similarity	NPD6832	Phase 2
0.6257	Remote Similarity	NPD3226	Approved
0.6257	Remote Similarity	NPD3748	Approved
0.6256	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD4111	Phase 1
0.6256	Remote Similarity	NPD4665	Approved
0.625	Remote Similarity	NPD8285	Discontinued
0.625	Remote Similarity	NPD8032	Phase 2
0.6235	Remote Similarity	NPD7492	Approved
0.6221	Remote Similarity	NPD7930	Approved
0.622	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6534	Approved
0.6214	Remote Similarity	NPD6535	Approved
0.6211	Remote Similarity	NPD2801	Approved
0.6209	Remote Similarity	NPD1243	Approved
0.6201	Remote Similarity	NPD7097	Phase 1
0.6199	Remote Similarity	NPD6616	Approved
0.619	Remote Similarity	NPD6054	Approved
0.6188	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD2346	Discontinued
0.6185	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD2403	Approved
0.617	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6823	Phase 2
0.6158	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1549	Phase 2
0.6141	Remote Similarity	NPD3887	Approved
0.6141	Remote Similarity	NPD6190	Approved
0.6133	Remote Similarity	NPD1551	Phase 2
0.6133	Remote Similarity	NPD6100	Approved
0.6133	Remote Similarity	NPD6099	Approved
0.6132	Remote Similarity	NPD7680	Approved
0.6129	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.612	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6370	Approved
0.6099	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5353	Approved
0.6089	Remote Similarity	NPD5735	Approved
0.6087	Remote Similarity	NPD3750	Approved
0.6085	Remote Similarity	NPD3057	Approved
0.6077	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7033	Discontinued
0.6077	Remote Similarity	NPD2799	Discontinued
0.6077	Remote Similarity	NPD8485	Approved
0.6075	Remote Similarity	NPD7999	Approved
0.6071	Remote Similarity	NPD7315	Approved
0.6071	Remote Similarity	NPD7229	Phase 3
0.6069	Remote Similarity	NPD8293	Discontinued
0.6066	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7048	Phase 3
0.6059	Remote Similarity	NPD6015	Approved
0.6059	Remote Similarity	NPD6016	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