NPASS Compound

Structure

NPC475482 OpenBabel07101718192D 46 51 0 0 1 0 0 0 0 0999 V2000 2.5481 3.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4904 -4.7724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7950 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9456 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0962 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6443 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7950 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2469 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 3.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9808 -3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 2.9423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6987 1.9615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9456 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6443 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8494 -1.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8494 -4.4135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3975 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 1.4712 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8494 2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -2.4519 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.9231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4712 -3.0737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4937 0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -5.3942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 -1.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 1.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 3.4327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 -0.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 37 1 0 0 0 0 6 9 1 0 0 0 0 6 26 2 0 0 0 0 7 10 2 0 0 0 0 7 26 1 0 0 0 0 8 13 2 0 0 0 0 8 26 1 0 0 0 0 9 27 2 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 28 2 0 0 0 0 12 30 1 0 0 0 0 13 32 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 31 1 0 0 0 0 17 35 1 0 0 0 0 18 37 1 0 0 0 0 19 38 1 0 0 0 0 20 21 1 0 0 0 0 20 38 1 0 0 0 0 21 39 1 0 0 0 0 22 36 1 0 0 0 0 22 40 1 0 0 0 0 23 46 1 0 0 0 0 24 1 1 1 0 0 0 24 25 1 0 0 0 0 25 2 1 6 0 0 0 25 33 1 0 0 0 0 27 41 1 0 0 0 0 28 33 1 0 0 0 0 28 39 1 0 0 0 0 29 35 1 6 0 0 0 29 36 1 0 0 0 0 30 35 1 6 0 0 0 30 37 1 0 0 0 0 31 36 1 6 0 0 0 31 42 1 0 0 0 0 32 43 2 0 0 0 0 32 46 1 0 0 0 0 33 38 1 1 0 0 0 34 44 2 0 0 0 0 34 45 1 0 0 0 0 35 3 1 6 0 0 0 36 4 1 6 0 0 0 37 39 1 1 0 0 0 38 34 1 6 0 0 0 39 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.39
Volume:	674.838
LogP:	5.376
LogD:	4.512
LogS:	-4.16
# Rotatable Bonds:	7
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	5.17
Fsp3:	0.692
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:	-5.583
MDCK Permeability:	1.5058479220897425e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.2
30% Bioavailability (F30%):	0.874

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.588
Plasma Protein Binding (PPB):	99.8867416381836%
Volume Distribution (VD):	0.461
Pgp-substrate:	2.306216239929199%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.51
CYP2C9-inhibitor:	0.31
CYP2C9-substrate:	0.488
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.325

ADMET: Excretion

Clearance (CL):	3.352
Half-life (T1/2):	0.483

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.672
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.248
Carcinogencity:	0.061
Eye Corrosion:	0.004
Eye Irritation:	0.037
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC475482

Natural Product ID:	NPC475482
*Common Name:**	(1S,2R,4As,6Ar,6Ar,6Br,8Ar,9R,10S,12Ar,14Bs)-10-Hydroxy-9-(Hydroxymethyl)-6A-[[(Z)-3-(4-Hydroxyphenyl)Prop-2-Enoyl]Oxymethyl]-1,2,6B,9,12A-Pentamethyl-2,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydro-1H-Picene-4A-Carboxylic Acid
IUPAC Name:	(1S,2R,4aS,6aR,6aR,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-6a-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,6b,9,12a-pentamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	UQWOVDOTSQPRJO-RBHNILKQSA-N
Standard InCHI:	InChI=1S/C39H54O7/c1-24-14-19-38(34(44)45)20-21-39(23-46-32(43)13-8-26-6-9-27(41)10-7-26)28(33(38)25(24)2)11-12-30-35(3)17-16-31(42)36(4,22-40)29(35)15-18-37(30,39)5/h6-11,13,24-25,29-31,33,40-42H,12,14-23H2,1-5H3,(H,44,45)/b13-8-/t24-,25+,29-,30-,31+,33+,35+,36+,37-,38+,39+/m1/s1
SMILES:	OC[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(COC(=O)/C=Cc1ccc(cc1)O)CC[C@@]1([C@H]2[C@@H](C)[C@@H](CC1)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506421
PubChem CID:	44566351
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3065	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Rattus norvegicus	IC50	=	194000.0	nM	PMID[537045]

☑ 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 NPC475482 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	306
0.1-0.2	1207
0.2-0.3	2367
0.3-0.4	4673
0.4-0.5	9036
0.5-0.6	11416
0.6-0.7	11753
0.7-0.8	1757
0.8-0.85	66
0.85-0.9	57
0.9-0.95	30
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC22676
1.0	High Similarity	NPC216940
1.0	High Similarity	NPC198621
0.9923	High Similarity	NPC249817
0.9846	High Similarity	NPC477874
0.9846	High Similarity	NPC173569
0.9627	High Similarity	NPC304110
0.9627	High Similarity	NPC472801
0.9627	High Similarity	NPC27518
0.9542	High Similarity	NPC475457
0.9542	High Similarity	NPC18982
0.9542	High Similarity	NPC475627
0.9542	High Similarity	NPC475346
0.9481	High Similarity	NPC172311
0.9478	High Similarity	NPC248287
0.9478	High Similarity	NPC234548
0.9416	High Similarity	NPC25491
0.9385	High Similarity	NPC86257
0.9343	High Similarity	NPC477873
0.9343	High Similarity	NPC469447
0.9286	High Similarity	NPC477483
0.9286	High Similarity	NPC325032
0.9254	High Similarity	NPC472804
0.9209	High Similarity	NPC53520
0.9179	High Similarity	NPC11266
0.9124	High Similarity	NPC271494
0.9124	High Similarity	NPC473591
0.9124	High Similarity	NPC155192
0.9077	High Similarity	NPC137416
0.9051	High Similarity	NPC182249
0.9051	High Similarity	NPC116742
0.9051	High Similarity	NPC139243
0.9028	High Similarity	NPC473773
0.9028	High Similarity	NPC475579
0.9007	High Similarity	NPC8102
0.9007	High Similarity	NPC66894
0.8986	High Similarity	NPC470616
0.8986	High Similarity	NPC470617
0.8958	High Similarity	NPC118033
0.8951	High Similarity	NPC279442
0.8897	High Similarity	NPC194970
0.8889	High Similarity	NPC327962
0.8855	High Similarity	NPC10154
0.8855	High Similarity	NPC474532
0.8855	High Similarity	NPC265413
0.8841	High Similarity	NPC471152
0.8828	High Similarity	NPC475311
0.8828	High Similarity	NPC473579
0.8828	High Similarity	NPC473680
0.8828	High Similarity	NPC475454
0.8794	High Similarity	NPC310621
0.8794	High Similarity	NPC235557
0.8732	High Similarity	NPC26045
0.8723	High Similarity	NPC35212
0.8716	High Similarity	NPC472807
0.8696	High Similarity	NPC43353
0.869	High Similarity	NPC473719
0.8662	High Similarity	NPC252133
0.8652	High Similarity	NPC473612
0.8582	High Similarity	NPC190849
0.8582	High Similarity	NPC171007
0.8581	High Similarity	NPC105942
0.8581	High Similarity	NPC205392
0.8552	High Similarity	NPC472936
0.8552	High Similarity	NPC472937
0.8552	High Similarity	NPC472938
0.8542	High Similarity	NPC307205
0.8451	Intermediate Similarity	NPC471875
0.8444	Intermediate Similarity	NPC473220
0.8444	Intermediate Similarity	NPC470753
0.8431	Intermediate Similarity	NPC266365
0.8429	Intermediate Similarity	NPC279463
0.8421	Intermediate Similarity	NPC478058
0.8394	Intermediate Similarity	NPC131684
0.8378	Intermediate Similarity	NPC470619
0.8378	Intermediate Similarity	NPC208785
0.8378	Intermediate Similarity	NPC35160
0.8378	Intermediate Similarity	NPC162569
0.8378	Intermediate Similarity	NPC116292
0.8378	Intermediate Similarity	NPC470618
0.8378	Intermediate Similarity	NPC472939
0.8378	Intermediate Similarity	NPC145527
0.8378	Intermediate Similarity	NPC267469
0.8378	Intermediate Similarity	NPC87630
0.8378	Intermediate Similarity	NPC179128
0.837	Intermediate Similarity	NPC470765
0.837	Intermediate Similarity	NPC275576
0.8356	Intermediate Similarity	NPC320734
0.8345	Intermediate Similarity	NPC477207
0.8333	Intermediate Similarity	NPC477468
0.8311	Intermediate Similarity	NPC477206
0.8309	Intermediate Similarity	NPC169913
0.8286	Intermediate Similarity	NPC476282
0.8286	Intermediate Similarity	NPC203486
0.8276	Intermediate Similarity	NPC477209
0.8276	Intermediate Similarity	NPC204644
0.8273	Intermediate Similarity	NPC18798
0.8267	Intermediate Similarity	NPC48671
0.8261	Intermediate Similarity	NPC475138
0.8261	Intermediate Similarity	NPC288290
0.8258	Intermediate Similarity	NPC42657
0.8255	Intermediate Similarity	NPC247219
0.8219	Intermediate Similarity	NPC474599
0.8214	Intermediate Similarity	NPC165612
0.82	Intermediate Similarity	NPC140133
0.82	Intermediate Similarity	NPC261659
0.8194	Intermediate Similarity	NPC79372
0.8188	Intermediate Similarity	NPC253591
0.8188	Intermediate Similarity	NPC146388
0.8182	Intermediate Similarity	NPC477592
0.8176	Intermediate Similarity	NPC470330
0.8176	Intermediate Similarity	NPC477208
0.8175	Intermediate Similarity	NPC471929
0.8175	Intermediate Similarity	NPC71610
0.8175	Intermediate Similarity	NPC471930
0.8175	Intermediate Similarity	NPC471935
0.817	Intermediate Similarity	NPC469507
0.8156	Intermediate Similarity	NPC126516
0.8156	Intermediate Similarity	NPC48929
0.8148	Intermediate Similarity	NPC121168
0.8143	Intermediate Similarity	NPC243305
0.8138	Intermediate Similarity	NPC470035
0.8133	Intermediate Similarity	NPC146014
0.8129	Intermediate Similarity	NPC117899
0.8125	Intermediate Similarity	NPC469774
0.8125	Intermediate Similarity	NPC135334
0.8125	Intermediate Similarity	NPC295941
0.8125	Intermediate Similarity	NPC469773
0.8125	Intermediate Similarity	NPC100925
0.8125	Intermediate Similarity	NPC469777
0.8125	Intermediate Similarity	NPC469778
0.8125	Intermediate Similarity	NPC469775
0.8125	Intermediate Similarity	NPC265335
0.8125	Intermediate Similarity	NPC469776
0.8125	Intermediate Similarity	NPC32723
0.8125	Intermediate Similarity	NPC469772
0.8108	Intermediate Similarity	NPC208293
0.8101	Intermediate Similarity	NPC200726
0.8099	Intermediate Similarity	NPC471864
0.8095	Intermediate Similarity	NPC478164
0.8095	Intermediate Similarity	NPC471876
0.8074	Intermediate Similarity	NPC249340
0.8074	Intermediate Similarity	NPC162935
0.8067	Intermediate Similarity	NPC273358
0.8067	Intermediate Similarity	NPC298647
0.8063	Intermediate Similarity	NPC472803
0.8058	Intermediate Similarity	NPC469930
0.8058	Intermediate Similarity	NPC193203
0.8058	Intermediate Similarity	NPC229894
0.805	Intermediate Similarity	NPC177362
0.8042	Intermediate Similarity	NPC472372
0.8042	Intermediate Similarity	NPC103082
0.8042	Intermediate Similarity	NPC472374
0.8041	Intermediate Similarity	NPC169942
0.8041	Intermediate Similarity	NPC280717
0.8041	Intermediate Similarity	NPC235195
0.8041	Intermediate Similarity	NPC19862
0.8041	Intermediate Similarity	NPC271607
0.8029	Intermediate Similarity	NPC181334
0.8028	Intermediate Similarity	NPC472591
0.8028	Intermediate Similarity	NPC49742
0.8028	Intermediate Similarity	NPC329913
0.8027	Intermediate Similarity	NPC184935
0.8025	Intermediate Similarity	NPC315772
0.8014	Intermediate Similarity	NPC258073
0.8012	Intermediate Similarity	NPC13989
0.8	Intermediate Similarity	NPC96930
0.8	Intermediate Similarity	NPC132723
0.8	Intermediate Similarity	NPC202428
0.8	Intermediate Similarity	NPC76032
0.8	Intermediate Similarity	NPC471870
0.8	Intermediate Similarity	NPC477593
0.8	Intermediate Similarity	NPC266545
0.8	Intermediate Similarity	NPC32017
0.8	Intermediate Similarity	NPC164852
0.8	Intermediate Similarity	NPC241001
0.7987	Intermediate Similarity	NPC478160
0.7986	Intermediate Similarity	NPC262324
0.7975	Intermediate Similarity	NPC161151
0.7974	Intermediate Similarity	NPC474534
0.7974	Intermediate Similarity	NPC473544
0.7974	Intermediate Similarity	NPC475145
0.7974	Intermediate Similarity	NPC475162
0.7974	Intermediate Similarity	NPC266084
0.7974	Intermediate Similarity	NPC474533
0.7974	Intermediate Similarity	NPC475216
0.7974	Intermediate Similarity	NPC83663
0.7974	Intermediate Similarity	NPC475595
0.7973	Intermediate Similarity	NPC472556
0.7973	Intermediate Similarity	NPC96447
0.7972	Intermediate Similarity	NPC27394
0.7972	Intermediate Similarity	NPC477594
0.7971	Intermediate Similarity	NPC87985
0.7961	Intermediate Similarity	NPC119252
0.7961	Intermediate Similarity	NPC77310
0.7959	Intermediate Similarity	NPC91703
0.7959	Intermediate Similarity	NPC477595
0.7959	Intermediate Similarity	NPC20631
0.7959	Intermediate Similarity	NPC93640
0.7956	Intermediate Similarity	NPC12881

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 NPC475482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	804
0.2-0.3	1418
0.3-0.4	2530
0.4-0.5	2249
0.5-0.6	1371
0.6-0.7	487
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD8166	Discontinued
0.8273	Intermediate Similarity	NPD6663	Approved
0.8248	Intermediate Similarity	NPD5736	Approved
0.8207	Intermediate Similarity	NPD7003	Approved
0.8054	Intermediate Similarity	NPD6273	Approved
0.8013	Intermediate Similarity	NPD7458	Discontinued
0.7848	Intermediate Similarity	NPD8127	Discontinued
0.7794	Intermediate Similarity	NPD2932	Approved
0.7794	Intermediate Similarity	NPD3019	Approved
0.7733	Intermediate Similarity	NPD7236	Approved
0.7718	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD8032	Phase 2
0.76	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD4140	Approved
0.7569	Intermediate Similarity	NPD3764	Approved
0.7568	Intermediate Similarity	NPD5408	Approved
0.7568	Intermediate Similarity	NPD5405	Approved
0.7568	Intermediate Similarity	NPD5404	Approved
0.7568	Intermediate Similarity	NPD5406	Approved
0.7518	Intermediate Similarity	NPD3091	Approved
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7008	Discontinued
0.7484	Intermediate Similarity	NPD7239	Suspended
0.7484	Intermediate Similarity	NPD7768	Phase 2
0.7465	Intermediate Similarity	NPD2797	Approved
0.745	Intermediate Similarity	NPD2935	Discontinued
0.7432	Intermediate Similarity	NPD7097	Phase 1
0.7415	Intermediate Similarity	NPD6355	Discontinued
0.7394	Intermediate Similarity	NPD1283	Approved
0.7379	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3750	Approved
0.7357	Intermediate Similarity	NPD3026	Approved
0.7357	Intermediate Similarity	NPD3023	Approved
0.7353	Intermediate Similarity	NPD2629	Approved
0.7343	Intermediate Similarity	NPD3094	Phase 2
0.7338	Intermediate Similarity	NPD3024	Approved
0.7338	Intermediate Similarity	NPD3025	Approved
0.7337	Intermediate Similarity	NPD8312	Approved
0.7337	Intermediate Similarity	NPD8313	Approved
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD3268	Approved
0.732	Intermediate Similarity	NPD6190	Approved
0.732	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3092	Approved
0.7303	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3095	Discontinued
0.7286	Intermediate Similarity	NPD4626	Approved
0.7285	Intermediate Similarity	NPD7266	Discontinued
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD9545	Approved
0.726	Intermediate Similarity	NPD7095	Approved
0.7255	Intermediate Similarity	NPD4110	Phase 3
0.7255	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7819	Suspended
0.725	Intermediate Similarity	NPD8455	Phase 2
0.723	Intermediate Similarity	NPD2979	Phase 3
0.723	Intermediate Similarity	NPD4060	Phase 1
0.7226	Intermediate Similarity	NPD5951	Approved
0.7225	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2438	Suspended
0.7214	Intermediate Similarity	NPD5691	Approved
0.7209	Intermediate Similarity	NPD8150	Discontinued
0.7206	Intermediate Similarity	NPD7094	Approved
0.7206	Intermediate Similarity	NPD6858	Approved
0.7205	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD37	Approved
0.7186	Intermediate Similarity	NPD7228	Approved
0.7183	Intermediate Similarity	NPD1281	Approved
0.7169	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6233	Phase 2
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7125	Intermediate Similarity	NPD6677	Suspended
0.7122	Intermediate Similarity	NPD9493	Approved
0.7115	Intermediate Similarity	NPD7390	Discontinued
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD6099	Approved
0.7103	Intermediate Similarity	NPD1470	Approved
0.7103	Intermediate Similarity	NPD1164	Approved
0.7095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5327	Phase 3
0.7073	Intermediate Similarity	NPD6234	Discontinued
0.7067	Intermediate Similarity	NPD5735	Approved
0.7063	Intermediate Similarity	NPD7028	Phase 2
0.7063	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7055	Intermediate Similarity	NPD7057	Phase 3
0.7055	Intermediate Similarity	NPD7058	Phase 2
0.705	Intermediate Similarity	NPD4198	Discontinued
0.7047	Intermediate Similarity	NPD7961	Discontinued
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3748	Approved
0.7039	Intermediate Similarity	NPD4308	Phase 3
0.7021	Intermediate Similarity	NPD7741	Discontinued
0.7019	Intermediate Similarity	NPD7411	Suspended
0.7014	Intermediate Similarity	NPD3972	Approved
0.7013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7075	Discontinued
0.7011	Intermediate Similarity	NPD8434	Phase 2
0.7006	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3620	Phase 2
0.6993	Remote Similarity	NPD2531	Phase 2
0.6993	Remote Similarity	NPD4477	Approved
0.6993	Remote Similarity	NPD4476	Approved
0.6992	Remote Similarity	NPD5909	Discontinued
0.6988	Remote Similarity	NPD6959	Discontinued
0.6986	Remote Similarity	NPD3266	Approved
0.6986	Remote Similarity	NPD3267	Approved
0.698	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5585	Approved
0.6972	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1651	Approved
0.6962	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4908	Phase 1
0.6959	Remote Similarity	NPD6832	Phase 2
0.6957	Remote Similarity	NPD4380	Phase 2
0.6954	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5124	Phase 1
0.6951	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5762	Approved
0.6948	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6005	Phase 3
0.6948	Remote Similarity	NPD5763	Approved
0.6948	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6004	Phase 3
0.6948	Remote Similarity	NPD6002	Phase 3
0.6947	Remote Similarity	NPD3020	Approved
0.6939	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD7714	Approved
0.6933	Remote Similarity	NPD7715	Approved
0.6933	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7033	Discontinued
0.6923	Remote Similarity	NPD1778	Approved
0.6923	Remote Similarity	NPD4059	Approved
0.6923	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7473	Discontinued
0.6917	Remote Similarity	NPD6647	Phase 2
0.6908	Remote Similarity	NPD6653	Approved
0.6908	Remote Similarity	NPD6353	Approved
0.6906	Remote Similarity	NPD1241	Discontinued
0.6906	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6010	Discontinued
0.6903	Remote Similarity	NPD4534	Discontinued
0.6901	Remote Similarity	NPD1894	Discontinued
0.6899	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1608	Approved
0.6894	Remote Similarity	NPD3226	Approved
0.6889	Remote Similarity	NPD3134	Approved
0.6882	Remote Similarity	NPD7799	Discontinued
0.6875	Remote Similarity	NPD7427	Discontinued
0.6875	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD3847	Discontinued
0.6871	Remote Similarity	NPD1203	Approved
0.6867	Remote Similarity	NPD2313	Discontinued
0.686	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2534	Approved
0.6855	Remote Similarity	NPD2533	Approved
0.6855	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2532	Approved
0.6852	Remote Similarity	NPD6599	Discontinued
0.6849	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2614	Approved
0.6845	Remote Similarity	NPD6232	Discontinued
0.6842	Remote Similarity	NPD230	Phase 1
0.6839	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5535	Approved
0.6835	Remote Similarity	NPD7440	Discontinued
0.6829	Remote Similarity	NPD5761	Phase 2
0.6829	Remote Similarity	NPD5760	Phase 2
0.6828	Remote Similarity	NPD1535	Discovery
0.6824	Remote Similarity	NPD4624	Approved
0.6821	Remote Similarity	NPD4062	Phase 3
0.6821	Remote Similarity	NPD7240	Approved
0.6818	Remote Similarity	NPD7743	Approved
0.6818	Remote Similarity	NPD1510	Phase 2
0.6818	Remote Similarity	NPD7742	Approved
0.6815	Remote Similarity	NPD3400	Discontinued
0.6812	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7157	Approved
0.6807	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8651	Approved
0.6803	Remote Similarity	NPD3225	Approved
0.6803	Remote Similarity	NPD1876	Approved
0.6797	Remote Similarity	NPD4097	Suspended
0.6795	Remote Similarity	NPD1549	Phase 2

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