NPASS Compound

Structure

NPC473159 OpenBabel07101718322D 57 62 0 0 1 0 0 0 0 0999 V2000 -8.3896 -2.9062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7117 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5507 -5.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3896 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1935 -3.7452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1623 -3.7452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8715 2.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8402 2.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3896 -3.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5507 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1948 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3558 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 -2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 -3.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5507 -4.3594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5507 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -1.4531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0338 -2.9062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5169 1.4531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6779 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1948 1.4531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6779 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5169 -1.4531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0338 -0.9687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8727 -2.4219 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8727 -1.4531 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7117 -3.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7117 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -1.4531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6779 -2.9062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3558 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 0.4844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8390 0.4844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6779 -0.9687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1948 -4.3594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -0.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0338 1.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 0.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8727 -4.3594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8727 0.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -2.4219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 -0.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7117 -2.9062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7117 -0.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 41 1 0 0 0 0 6 41 1 0 0 0 0 7 42 1 0 0 0 0 8 42 1 0 0 0 0 10 44 1 0 0 0 0 12 25 2 0 0 0 0 13 26 2 0 0 0 0 14 15 1 0 0 0 0 14 27 2 0 0 0 0 15 31 1 0 0 0 0 16 19 1 0 0 0 0 16 30 1 0 0 0 0 17 18 2 0 0 0 0 17 32 1 0 0 0 0 18 43 1 0 0 0 0 19 44 1 0 0 0 0 20 28 1 0 0 0 0 20 41 1 0 0 0 0 21 33 1 0 0 0 0 21 45 1 0 0 0 0 22 34 1 0 0 0 0 22 41 1 0 0 0 0 23 47 1 0 0 0 0 24 48 1 0 0 0 0 25 38 1 0 0 0 0 26 39 1 0 0 0 0 27 28 1 0 0 0 0 27 45 1 0 0 0 0 28 46 1 6 0 0 0 29 23 1 6 0 0 0 29 36 1 0 0 0 0 29 54 1 0 0 0 0 30 42 1 0 0 0 0 30 43 1 1 0 0 0 31 43 1 1 0 0 0 31 44 1 0 0 0 0 32 42 1 0 0 0 0 32 49 1 1 0 0 0 33 46 1 6 0 0 0 33 50 1 0 0 0 0 34 46 1 6 0 0 0 34 55 1 0 0 0 0 35 37 1 0 0 0 0 35 40 1 0 0 0 0 35 51 1 1 0 0 0 36 37 1 0 0 0 0 36 56 1 1 0 0 0 37 57 1 6 0 0 0 38 52 2 0 0 0 0 38 56 1 0 0 0 0 39 53 2 0 0 0 0 39 57 1 0 0 0 0 40 54 1 0 0 0 0 40 55 1 6 0 0 0 43 9 1 1 0 0 0 44 45 1 6 0 0 0 45 11 1 6 0 0 0 46 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	798.49
Volume:	833.707
LogP:	4.786
LogD:	3.752
LogS:	-4.474
# Rotatable Bonds:	10
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	6.16
Fsp3:	0.783
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:	-5.193
MDCK Permeability:	2.3812490326236002e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.341
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.692

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	85.22132873535156%
Volume Distribution (VD):	1.492
Pgp-substrate:	4.631875991821289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.546
CYP2C9-inhibitor:	0.571
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.432
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.514

ADMET: Excretion

Clearance (CL):	2.924
Half-life (T1/2):	0.35

ADMET: Toxicity

hERG Blockers:	0.793
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.356
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC473159

Natural Product ID:	NPC473159
*Common Name:**	GHOMOQOSGKMYHT-IUYCQTIWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GHOMOQOSGKMYHT-IUYCQTIWSA-N
Standard InCHI:	InChI=1S/C46H70O11/c1-12-25(3)38(52)56-36-29(23-47)54-40(35(51)37(36)57-39(53)26(4)13-2)55-34-22-41(5,6)20-28-27-14-15-31-43(9)18-17-32(49)42(7,8)30(43)16-19-44(31,10)45(27,11)21-33(50)46(28,34)24-48/h12-14,17-18,28-37,40,47-51H,15-16,19-24H2,1-11H3/b25-12-,26-13-/t28-,29+,30-,31+,32-,33+,34-,35+,36+,37+,40-,43-,44+,45+,46-/m0/s1
SMILES:	CC=C(C)C(=O)OC1C(OC(C(C1OC(=O)C(=CC)C)O)OC2CC(CC3C2(C(CC4(C3=CCC5C4(CCC6C5(C=CC(C6(C)C)O)C)C)C)O)CO)(C)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632763
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO33464	cyrilla racemiflora	Species	Cyrillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422131]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[471393]

☑ 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 NPC473159 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	248
0.1-0.2	1601
0.2-0.3	4553
0.3-0.4	9171
0.4-0.5	12095
0.5-0.6	7471
0.6-0.7	4618
0.7-0.8	2201
0.8-0.85	654
0.85-0.9	78
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9099	High Similarity	NPC470515
0.9018	High Similarity	NPC470911
0.9018	High Similarity	NPC470915
0.9018	High Similarity	NPC470914
0.9018	High Similarity	NPC470517
0.8879	High Similarity	NPC297950
0.8818	High Similarity	NPC473125
0.8796	High Similarity	NPC475263
0.8774	High Similarity	NPC473123
0.8774	High Similarity	NPC473124
0.8772	High Similarity	NPC135369
0.875	High Similarity	NPC207637
0.8739	High Similarity	NPC44298
0.8739	High Similarity	NPC49413
0.8739	High Similarity	NPC290608
0.8739	High Similarity	NPC473128
0.8739	High Similarity	NPC40133
0.8729	High Similarity	NPC472269
0.8729	High Similarity	NPC112492
0.8729	High Similarity	NPC23020
0.8729	High Similarity	NPC472268
0.8729	High Similarity	NPC472270
0.8716	High Similarity	NPC137917
0.8704	High Similarity	NPC473586
0.8692	High Similarity	NPC173583
0.8692	High Similarity	NPC473127
0.8692	High Similarity	NPC470768
0.8692	High Similarity	NPC203354
0.8692	High Similarity	NPC110656
0.8673	High Similarity	NPC473405
0.8649	High Similarity	NPC471967
0.8649	High Similarity	NPC328074
0.8649	High Similarity	NPC317460
0.8649	High Similarity	NPC470025
0.8649	High Similarity	NPC321272
0.8636	High Similarity	NPC78046
0.8636	High Similarity	NPC269095
0.8636	High Similarity	NPC220984
0.8611	High Similarity	NPC470763
0.8611	High Similarity	NPC470767
0.8611	High Similarity	NPC88349
0.8609	High Similarity	NPC476150
0.8609	High Similarity	NPC476127
0.8609	High Similarity	NPC470312
0.8598	High Similarity	NPC162354
0.8596	High Similarity	NPC471548
0.8585	High Similarity	NPC280991
0.8585	High Similarity	NPC477717
0.8571	High Similarity	NPC45606
0.8571	High Similarity	NPC470027
0.8571	High Similarity	NPC264153
0.8571	High Similarity	NPC220838
0.8559	High Similarity	NPC17791
0.8545	High Similarity	NPC237503
0.8545	High Similarity	NPC306746
0.8545	High Similarity	NPC167383
0.8545	High Similarity	NPC57362
0.8545	High Similarity	NPC204407
0.8534	High Similarity	NPC476204
0.8534	High Similarity	NPC170084
0.8534	High Similarity	NPC40749
0.8532	High Similarity	NPC472390
0.8532	High Similarity	NPC281939
0.8522	High Similarity	NPC470897
0.8522	High Similarity	NPC292467
0.8522	High Similarity	NPC236973
0.8522	High Similarity	NPC469756
0.8522	High Similarity	NPC32177
0.8522	High Similarity	NPC55532
0.8522	High Similarity	NPC30483
0.8512	High Similarity	NPC322904
0.8512	High Similarity	NPC319719
0.8512	High Similarity	NPC475177
0.8512	High Similarity	NPC233223
0.8512	High Similarity	NPC183816
0.8512	High Similarity	NPC196874
0.8512	High Similarity	NPC324933
0.8512	High Similarity	NPC473679
0.8512	High Similarity	NPC475444
0.8509	High Similarity	NPC474483
0.8509	High Similarity	NPC471547
0.8509	High Similarity	NPC93883
0.8505	High Similarity	NPC283343
0.8505	High Similarity	NPC258547
0.8505	High Similarity	NPC121423
0.8505	High Similarity	NPC201191
0.8491	Intermediate Similarity	NPC477721
0.8491	Intermediate Similarity	NPC477716
0.8487	Intermediate Similarity	NPC470516
0.8476	Intermediate Similarity	NPC125551
0.8476	Intermediate Similarity	NPC240372
0.8476	Intermediate Similarity	NPC309503
0.8476	Intermediate Similarity	NPC96597
0.8476	Intermediate Similarity	NPC91197
0.8476	Intermediate Similarity	NPC155319
0.8476	Intermediate Similarity	NPC239547
0.8475	Intermediate Similarity	NPC471090
0.8468	Intermediate Similarity	NPC274507
0.8468	Intermediate Similarity	NPC108709
0.8468	Intermediate Similarity	NPC476883
0.8468	Intermediate Similarity	NPC474589
0.8468	Intermediate Similarity	NPC270667
0.8468	Intermediate Similarity	NPC75747
0.8468	Intermediate Similarity	NPC199457
0.8468	Intermediate Similarity	NPC102914
0.8468	Intermediate Similarity	NPC476885
0.8468	Intermediate Similarity	NPC164194
0.8468	Intermediate Similarity	NPC174679
0.8468	Intermediate Similarity	NPC136877
0.8468	Intermediate Similarity	NPC56713
0.8468	Intermediate Similarity	NPC29069
0.8468	Intermediate Similarity	NPC68419
0.8468	Intermediate Similarity	NPC279554
0.8468	Intermediate Similarity	NPC476886
0.8468	Intermediate Similarity	NPC316708
0.8468	Intermediate Similarity	NPC59804
0.8468	Intermediate Similarity	NPC476881
0.8468	Intermediate Similarity	NPC476884
0.8468	Intermediate Similarity	NPC476880
0.8468	Intermediate Similarity	NPC475296
0.8468	Intermediate Similarity	NPC7870
0.8468	Intermediate Similarity	NPC90856
0.8468	Intermediate Similarity	NPC476887
0.8468	Intermediate Similarity	NPC127056
0.8468	Intermediate Similarity	NPC476882
0.8468	Intermediate Similarity	NPC110139
0.8455	Intermediate Similarity	NPC38376
0.8455	Intermediate Similarity	NPC470024
0.8455	Intermediate Similarity	NPC219900
0.8455	Intermediate Similarity	NPC177524
0.8455	Intermediate Similarity	NPC28198
0.8455	Intermediate Similarity	NPC284807
0.8455	Intermediate Similarity	NPC476123
0.8455	Intermediate Similarity	NPC177246
0.8455	Intermediate Similarity	NPC392
0.8455	Intermediate Similarity	NPC80210
0.8448	Intermediate Similarity	NPC475629
0.8448	Intermediate Similarity	NPC475556
0.8448	Intermediate Similarity	NPC72260
0.8448	Intermediate Similarity	NPC48692
0.844	Intermediate Similarity	NPC218158
0.844	Intermediate Similarity	NPC82251
0.843	Intermediate Similarity	NPC311178
0.843	Intermediate Similarity	NPC43589
0.843	Intermediate Similarity	NPC300655
0.843	Intermediate Similarity	NPC222951
0.8426	Intermediate Similarity	NPC99627
0.8426	Intermediate Similarity	NPC473129
0.8426	Intermediate Similarity	NPC281378
0.8421	Intermediate Similarity	NPC44170
0.8421	Intermediate Similarity	NPC193382
0.8421	Intermediate Similarity	NPC199428
0.8421	Intermediate Similarity	NPC268954
0.8421	Intermediate Similarity	NPC99620
0.8421	Intermediate Similarity	NPC5311
0.8421	Intermediate Similarity	NPC310341
0.8417	Intermediate Similarity	NPC477193
0.8417	Intermediate Similarity	NPC477192
0.8417	Intermediate Similarity	NPC477191
0.8417	Intermediate Similarity	NPC477194
0.8417	Intermediate Similarity	NPC245094
0.8411	Intermediate Similarity	NPC473160
0.8411	Intermediate Similarity	NPC198992
0.8403	Intermediate Similarity	NPC179261
0.8396	Intermediate Similarity	NPC477928
0.8393	Intermediate Similarity	NPC297208
0.8393	Intermediate Similarity	NPC108748
0.8393	Intermediate Similarity	NPC31839
0.8393	Intermediate Similarity	NPC30397
0.8393	Intermediate Similarity	NPC191763
0.8393	Intermediate Similarity	NPC179434
0.8393	Intermediate Similarity	NPC190837
0.8393	Intermediate Similarity	NPC211798
0.8393	Intermediate Similarity	NPC164419
0.8393	Intermediate Similarity	NPC235841
0.8393	Intermediate Similarity	NPC473481
0.8393	Intermediate Similarity	NPC470026
0.8378	Intermediate Similarity	NPC285253
0.8378	Intermediate Similarity	NPC221110
0.8378	Intermediate Similarity	NPC180459
0.8378	Intermediate Similarity	NPC195116
0.8378	Intermediate Similarity	NPC40728
0.8378	Intermediate Similarity	NPC127853
0.8376	Intermediate Similarity	NPC120390
0.8376	Intermediate Similarity	NPC475590
0.8376	Intermediate Similarity	NPC202051
0.8376	Intermediate Similarity	NPC475419
0.8376	Intermediate Similarity	NPC474908
0.8376	Intermediate Similarity	NPC475219
0.8376	Intermediate Similarity	NPC173555
0.8376	Intermediate Similarity	NPC314535
0.8376	Intermediate Similarity	NPC231518
0.8364	Intermediate Similarity	NPC109376
0.8364	Intermediate Similarity	NPC283849
0.8364	Intermediate Similarity	NPC234160
0.8364	Intermediate Similarity	NPC473538
0.8362	Intermediate Similarity	NPC122971
0.8362	Intermediate Similarity	NPC5883
0.8362	Intermediate Similarity	NPC329905
0.8362	Intermediate Similarity	NPC29639

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 NPC473159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1734
0.2-0.3	3848
0.3-0.4	2206
0.4-0.5	710
0.5-0.6	303
0.6-0.7	89
0.7-0.8	23
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8534	High Similarity	NPD7503	Approved
0.8455	Intermediate Similarity	NPD6686	Approved
0.8448	Intermediate Similarity	NPD8377	Approved
0.8448	Intermediate Similarity	NPD8294	Approved
0.8376	Intermediate Similarity	NPD8335	Approved
0.8376	Intermediate Similarity	NPD8380	Approved
0.8376	Intermediate Similarity	NPD8033	Approved
0.8376	Intermediate Similarity	NPD8378	Approved
0.8376	Intermediate Similarity	NPD8379	Approved
0.8376	Intermediate Similarity	NPD8296	Approved
0.8276	Intermediate Similarity	NPD7327	Approved
0.8276	Intermediate Similarity	NPD7328	Approved
0.8205	Intermediate Similarity	NPD7516	Approved
0.8053	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7951	Intermediate Similarity	NPD7507	Approved
0.7934	Intermediate Similarity	NPD8328	Phase 3
0.7778	Intermediate Similarity	NPD8133	Approved
0.776	Intermediate Similarity	NPD7319	Approved
0.7719	Intermediate Similarity	NPD6412	Phase 2
0.7658	Intermediate Similarity	NPD7640	Approved
0.7658	Intermediate Similarity	NPD7639	Approved
0.7583	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7638	Approved
0.748	Intermediate Similarity	NPD8516	Approved
0.748	Intermediate Similarity	NPD8515	Approved
0.748	Intermediate Similarity	NPD8513	Phase 3
0.748	Intermediate Similarity	NPD8517	Approved
0.7411	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4225	Approved
0.7402	Intermediate Similarity	NPD7736	Approved
0.7295	Intermediate Similarity	NPD7115	Discovery
0.7281	Intermediate Similarity	NPD5344	Discontinued
0.7248	Intermediate Similarity	NPD7838	Discovery
0.7207	Intermediate Similarity	NPD7748	Approved
0.7168	Intermediate Similarity	NPD7902	Approved
0.7167	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7632	Discontinued
0.7027	Intermediate Similarity	NPD7515	Phase 2
0.7008	Intermediate Similarity	NPD6370	Approved
0.6967	Remote Similarity	NPD6882	Approved
0.6967	Remote Similarity	NPD8297	Approved
0.6942	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD46	Approved
0.6937	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD8293	Discontinued
0.6903	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7900	Approved
0.6899	Remote Similarity	NPD7492	Approved
0.6897	Remote Similarity	NPD6648	Approved
0.688	Remote Similarity	NPD6009	Approved
0.6852	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6054	Approved
0.685	Remote Similarity	NPD6319	Approved
0.6846	Remote Similarity	NPD6616	Approved
0.6794	Remote Similarity	NPD7078	Approved
0.6777	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4632	Approved
0.6761	Remote Similarity	NPD7625	Phase 1
0.6698	Remote Similarity	NPD7645	Phase 2
0.6694	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6881	Approved
0.6639	Remote Similarity	NPD6899	Approved
0.6615	Remote Similarity	NPD5988	Approved
0.6613	Remote Similarity	NPD6649	Approved
0.6613	Remote Similarity	NPD8130	Phase 1
0.6613	Remote Similarity	NPD6650	Approved
0.6589	Remote Similarity	NPD6059	Approved
0.6565	Remote Similarity	NPD6067	Discontinued
0.6557	Remote Similarity	NPD5697	Approved
0.6532	Remote Similarity	NPD6883	Approved
0.6532	Remote Similarity	NPD7102	Approved
0.6532	Remote Similarity	NPD7290	Approved
0.6522	Remote Similarity	NPD5778	Approved
0.6522	Remote Similarity	NPD8171	Discontinued
0.6522	Remote Similarity	NPD5779	Approved
0.648	Remote Similarity	NPD6869	Approved
0.648	Remote Similarity	NPD6617	Approved
0.648	Remote Similarity	NPD6847	Approved
0.6475	Remote Similarity	NPD5739	Approved
0.6475	Remote Similarity	NPD7128	Approved
0.6475	Remote Similarity	NPD6675	Approved
0.6475	Remote Similarity	NPD6402	Approved
0.6471	Remote Similarity	NPD7260	Phase 2
0.6452	Remote Similarity	NPD6013	Approved
0.6452	Remote Similarity	NPD6014	Approved
0.6452	Remote Similarity	NPD6372	Approved
0.6452	Remote Similarity	NPD6373	Approved
0.6452	Remote Similarity	NPD6012	Approved
0.6439	Remote Similarity	NPD7829	Approved
0.6439	Remote Similarity	NPD7830	Approved
0.6439	Remote Similarity	NPD7604	Phase 2
0.6435	Remote Similarity	NPD6411	Approved
0.6435	Remote Similarity	NPD7983	Approved
0.6435	Remote Similarity	NPD7637	Suspended
0.6412	Remote Similarity	NPD5983	Phase 2
0.64	Remote Similarity	NPD6371	Approved
0.6393	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3573	Approved
0.6371	Remote Similarity	NPD7320	Approved
0.6371	Remote Similarity	NPD6011	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6336	Discontinued
0.6339	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6083	Phase 2
0.6303	Remote Similarity	NPD6084	Phase 2
0.6299	Remote Similarity	NPD6053	Discontinued
0.6293	Remote Similarity	NPD6079	Approved
0.6293	Remote Similarity	NPD8035	Phase 2
0.6293	Remote Similarity	NPD8034	Phase 2
0.629	Remote Similarity	NPD5701	Approved
0.629	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6921	Approved
0.627	Remote Similarity	NPD4634	Approved
0.6261	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6101	Approved
0.6261	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6051	Approved
0.626	Remote Similarity	NPD5141	Approved
0.6239	Remote Similarity	NPD6399	Phase 3
0.6228	Remote Similarity	NPD7524	Approved
0.6198	Remote Similarity	NPD5286	Approved
0.6198	Remote Similarity	NPD5285	Approved
0.6198	Remote Similarity	NPD4696	Approved
0.6187	Remote Similarity	NPD8449	Approved
0.6182	Remote Similarity	NPD7525	Registered
0.6173	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3669	Approved
0.6161	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8450	Suspended
0.614	Remote Similarity	NPD7334	Approved
0.614	Remote Similarity	NPD5330	Approved
0.614	Remote Similarity	NPD7146	Approved
0.614	Remote Similarity	NPD6409	Approved
0.614	Remote Similarity	NPD6684	Approved
0.614	Remote Similarity	NPD7521	Approved
0.614	Remote Similarity	NPD3618	Phase 1
0.6136	Remote Similarity	NPD7100	Approved
0.6136	Remote Similarity	NPD7101	Approved
0.6134	Remote Similarity	NPD5695	Phase 3
0.6131	Remote Similarity	NPD6033	Approved
0.6127	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5328	Approved
0.6111	Remote Similarity	NPD7799	Discontinued
0.6106	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD8451	Approved
0.6098	Remote Similarity	NPD5226	Approved
0.6098	Remote Similarity	NPD5225	Approved
0.6098	Remote Similarity	NPD4633	Approved
0.6098	Remote Similarity	NPD5224	Approved
0.6096	Remote Similarity	NPD7266	Discontinued
0.6094	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5222	Approved
0.6083	Remote Similarity	NPD7614	Phase 1
0.6083	Remote Similarity	NPD7839	Suspended
0.6083	Remote Similarity	NPD7732	Phase 3
0.6083	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5221	Approved
0.608	Remote Similarity	NPD6008	Approved
0.6074	Remote Similarity	NPD7642	Approved
0.6071	Remote Similarity	NPD6845	Suspended
0.6061	Remote Similarity	NPD6335	Approved
0.6061	Remote Similarity	NPD7641	Discontinued
0.6058	Remote Similarity	NPD8448	Approved
0.6053	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5174	Approved
0.6048	Remote Similarity	NPD5175	Approved
0.6045	Remote Similarity	NPD8444	Approved
0.6043	Remote Similarity	NPD5956	Approved
0.6043	Remote Similarity	NPD8392	Approved
0.6043	Remote Similarity	NPD8391	Approved
0.6043	Remote Similarity	NPD8390	Approved
0.6034	Remote Similarity	NPD5737	Approved
0.6034	Remote Similarity	NPD6903	Approved
0.6034	Remote Similarity	NPD6672	Approved
0.6033	Remote Similarity	NPD5173	Approved
0.6033	Remote Similarity	NPD4755	Approved
0.6031	Remote Similarity	NPD6868	Approved
0.6031	Remote Similarity	NPD6274	Approved
0.6029	Remote Similarity	NPD8299	Approved
0.6029	Remote Similarity	NPD8341	Approved
0.6029	Remote Similarity	NPD8340	Approved
0.6029	Remote Similarity	NPD8342	Approved
0.6019	Remote Similarity	NPD8264	Approved
0.6018	Remote Similarity	NPD6695	Phase 3
0.6016	Remote Similarity	NPD5223	Approved
0.6014	Remote Similarity	NPD8336	Approved
0.6014	Remote Similarity	NPD8337	Approved
0.5985	Remote Similarity	NPD6317	Approved
0.5984	Remote Similarity	NPD4729	Approved
0.5984	Remote Similarity	NPD5696	Approved
0.5984	Remote Similarity	NPD4730	Approved
0.5966	Remote Similarity	NPD4202	Approved
0.5965	Remote Similarity	NPD3665	Phase 1
0.5965	Remote Similarity	NPD3133	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