NPASS Compound

Structure

NPC472436 OpenBabel07101719512D 48 53 0 0 1 0 0 0 0 0999 V2000 -1.2796 -7.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2705 1.6074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2651 1.7120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8638 0.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8528 0.9030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9075 -2.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5278 -2.2246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -7.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -6.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4516 -0.1151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4461 -0.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -3.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5035 -1.4119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -8.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -5.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -2.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -1.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6456 -1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 -7.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2437 -3.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8528 -0.9241 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8736 3.1915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3910 -0.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -9.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -9.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -6.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -3.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7796 -7.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 2.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -4.5933 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 -3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 14 2 0 0 0 0 5 16 2 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 8 30 1 0 0 0 0 9 21 1 0 0 0 0 9 30 1 0 0 0 0 10 17 1 0 0 0 0 10 32 2 0 0 0 0 11 44 1 0 0 0 0 12 31 1 0 0 0 0 12 34 1 0 0 0 0 13 31 1 0 0 0 0 13 45 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 22 2 0 0 0 0 17 46 1 0 0 0 0 18 11 1 1 0 0 0 18 24 1 0 0 0 0 18 47 1 0 0 0 0 19 33 1 0 0 0 0 19 35 2 0 0 0 0 20 36 2 0 0 0 0 20 37 1 0 0 0 0 21 38 2 0 0 0 0 21 44 1 0 0 0 0 22 23 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 24 39 1 6 0 0 0 25 26 1 0 0 0 0 25 40 1 1 0 0 0 26 28 1 0 0 0 0 26 48 1 6 0 0 0 27 29 1 0 0 0 0 27 31 1 6 0 0 0 27 41 1 0 0 0 0 28 46 1 1 0 0 0 28 47 1 0 0 0 0 29 45 1 0 0 0 0 29 48 1 1 0 0 0 30 1 1 1 0 0 0 30 42 1 0 0 0 0 31 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	674.2
Volume:	620.876
LogP:	-0.186
LogD:	-0.413
LogS:	-3.816
# Rotatable Bonds:	12
TPSA:	256.27
# H-Bond Aceptor:	17
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.087
Synthetic Accessibility Score:	5.138
Fsp3:	0.484
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.647
MDCK Permeability:	1.0029622899310198e-05
Pgp-inhibitor:	0.187
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.922
20% Bioavailability (F20%):	0.849
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	62.31300354003906%
Volume Distribution (VD):	0.518
Pgp-substrate:	16.325685501098633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.195
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	1.413
Half-life (T1/2):	0.783

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.124
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.487
Skin Sensitization:	0.019
Carcinogencity:	0.8
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC472436

Natural Product ID:	NPC472436
*Common Name:**	HSFDYJXFPJALEF-GNKCQKPXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HSFDYJXFPJALEF-GNKCQKPXSA-N
Standard InCHI:	InChI=1S/C31H34N2O15/c1-30(42,8-20(36)37)9-21(38)44-11-18-24(39)25(40)26(48-29-27(41)31(43,12-34)13-45-29)28(47-18)46-17-10-32-15-6-7-19(35)33-16-5-3-2-4-14(16)22(17)23(15)33/h2-7,10,18,24-29,34,39-43H,8-9,11-13H2,1H3,(H,36,37)/t18-,24-,25+,26-,27+,28-,29+,30-,31-/m1/s1
SMILES:	OC[C@@]1(O)CO[C@H]([C@@H]1O)O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)COC(=O)C[C@@](CC(=O)O)(O)C)Oc1cnc2c3c1c1ccccc1n3c(=O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3403682
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[450484]

☑ 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 NPC472436 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	493
0.1-0.2	2164
0.2-0.3	8518
0.3-0.4	11113
0.4-0.5	13667
0.5-0.6	4951
0.6-0.7	1598
0.7-0.8	188
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC472435
0.9513	High Similarity	NPC472434
0.8718	High Similarity	NPC99891
0.8142	Intermediate Similarity	NPC287208
0.7851	Intermediate Similarity	NPC141053
0.7821	Intermediate Similarity	NPC288349
0.7773	Intermediate Similarity	NPC124300
0.7751	Intermediate Similarity	NPC310618
0.7742	Intermediate Similarity	NPC291609
0.7659	Intermediate Similarity	NPC26543
0.7639	Intermediate Similarity	NPC174672
0.7615	Intermediate Similarity	NPC128115
0.7564	Intermediate Similarity	NPC174758
0.7559	Intermediate Similarity	NPC473800
0.7549	Intermediate Similarity	NPC258048
0.7537	Intermediate Similarity	NPC314222
0.7537	Intermediate Similarity	NPC196449
0.7521	Intermediate Similarity	NPC82548
0.7511	Intermediate Similarity	NPC239954
0.7489	Intermediate Similarity	NPC198673
0.7489	Intermediate Similarity	NPC477548
0.7467	Intermediate Similarity	NPC267928
0.7437	Intermediate Similarity	NPC151781
0.7437	Intermediate Similarity	NPC74562
0.7437	Intermediate Similarity	NPC316181
0.7435	Intermediate Similarity	NPC168911
0.743	Intermediate Similarity	NPC57453
0.7391	Intermediate Similarity	NPC316224
0.739	Intermediate Similarity	NPC182222
0.7381	Intermediate Similarity	NPC148889
0.7379	Intermediate Similarity	NPC469554
0.7375	Intermediate Similarity	NPC274982
0.7371	Intermediate Similarity	NPC474183
0.7359	Intermediate Similarity	NPC212213
0.7322	Intermediate Similarity	NPC26679
0.7315	Intermediate Similarity	NPC165964
0.7314	Intermediate Similarity	NPC314270
0.73	Intermediate Similarity	NPC328928
0.7296	Intermediate Similarity	NPC19872
0.7292	Intermediate Similarity	NPC476287
0.7288	Intermediate Similarity	NPC238457
0.7287	Intermediate Similarity	NPC110151
0.7284	Intermediate Similarity	NPC315804
0.7284	Intermediate Similarity	NPC313804
0.7277	Intermediate Similarity	NPC200836
0.7269	Intermediate Similarity	NPC328798
0.7269	Intermediate Similarity	NPC469589
0.7261	Intermediate Similarity	NPC226202
0.7258	Intermediate Similarity	NPC314954
0.7257	Intermediate Similarity	NPC474905
0.7253	Intermediate Similarity	NPC160127
0.7253	Intermediate Similarity	NPC50997
0.7243	Intermediate Similarity	NPC82070
0.724	Intermediate Similarity	NPC101543
0.7237	Intermediate Similarity	NPC161801
0.7236	Intermediate Similarity	NPC475271
0.7233	Intermediate Similarity	NPC470785
0.7231	Intermediate Similarity	NPC8022
0.7231	Intermediate Similarity	NPC470799
0.7227	Intermediate Similarity	NPC308392
0.7224	Intermediate Similarity	NPC473833
0.7218	Intermediate Similarity	NPC186351
0.7218	Intermediate Similarity	NPC244536
0.7208	Intermediate Similarity	NPC152620
0.7206	Intermediate Similarity	NPC212766
0.7206	Intermediate Similarity	NPC289423
0.7203	Intermediate Similarity	NPC326930
0.7203	Intermediate Similarity	NPC475301
0.7203	Intermediate Similarity	NPC53144
0.7197	Intermediate Similarity	NPC185782
0.7194	Intermediate Similarity	NPC184680
0.7193	Intermediate Similarity	NPC325775
0.719	Intermediate Similarity	NPC274842
0.7178	Intermediate Similarity	NPC244856
0.7176	Intermediate Similarity	NPC53534
0.7176	Intermediate Similarity	NPC13603
0.7174	Intermediate Similarity	NPC127647
0.7173	Intermediate Similarity	NPC118832
0.7173	Intermediate Similarity	NPC329708
0.7173	Intermediate Similarity	NPC165349
0.7173	Intermediate Similarity	NPC264166
0.7173	Intermediate Similarity	NPC274291
0.7173	Intermediate Similarity	NPC47059
0.7165	Intermediate Similarity	NPC314882
0.7165	Intermediate Similarity	NPC470784
0.7161	Intermediate Similarity	NPC211813
0.7154	Intermediate Similarity	NPC90019
0.7154	Intermediate Similarity	NPC60621
0.7149	Intermediate Similarity	NPC306644
0.7149	Intermediate Similarity	NPC236424
0.7143	Intermediate Similarity	NPC52254
0.7143	Intermediate Similarity	NPC472111
0.7143	Intermediate Similarity	NPC220852
0.7137	Intermediate Similarity	NPC478045
0.7137	Intermediate Similarity	NPC85879
0.7137	Intermediate Similarity	NPC53255
0.7131	Intermediate Similarity	NPC475774
0.7126	Intermediate Similarity	NPC285343
0.7121	Intermediate Similarity	NPC478006
0.7119	Intermediate Similarity	NPC153452
0.7115	Intermediate Similarity	NPC253675
0.7113	Intermediate Similarity	NPC193238
0.7107	Intermediate Similarity	NPC111732
0.7105	Intermediate Similarity	NPC471978
0.7103	Intermediate Similarity	NPC196718
0.7102	Intermediate Similarity	NPC469594
0.7093	Intermediate Similarity	NPC471013
0.7093	Intermediate Similarity	NPC180668
0.7093	Intermediate Similarity	NPC148896
0.7093	Intermediate Similarity	NPC325093
0.709	Intermediate Similarity	NPC476114
0.709	Intermediate Similarity	NPC315467
0.7089	Intermediate Similarity	NPC311357
0.7087	Intermediate Similarity	NPC182814
0.7085	Intermediate Similarity	NPC310118
0.7078	Intermediate Similarity	NPC234078
0.7078	Intermediate Similarity	NPC221100
0.7076	Intermediate Similarity	NPC79223
0.7071	Intermediate Similarity	NPC471736
0.7068	Intermediate Similarity	NPC473449
0.7068	Intermediate Similarity	NPC21638
0.7066	Intermediate Similarity	NPC475533
0.7066	Intermediate Similarity	NPC58209
0.7063	Intermediate Similarity	NPC478009
0.7063	Intermediate Similarity	NPC260434
0.7063	Intermediate Similarity	NPC478010
0.7059	Intermediate Similarity	NPC476115
0.7054	Intermediate Similarity	NPC75179
0.705	Intermediate Similarity	NPC10904
0.7046	Intermediate Similarity	NPC32451
0.7045	Intermediate Similarity	NPC472099
0.7042	Intermediate Similarity	NPC316403
0.7042	Intermediate Similarity	NPC156044
0.7039	Intermediate Similarity	NPC79293
0.7039	Intermediate Similarity	NPC279401
0.7038	Intermediate Similarity	NPC324619
0.7038	Intermediate Similarity	NPC475315
0.7037	Intermediate Similarity	NPC264176
0.7037	Intermediate Similarity	NPC472098
0.7037	Intermediate Similarity	NPC292517
0.7036	Intermediate Similarity	NPC102593
0.7034	Intermediate Similarity	NPC471015
0.7033	Intermediate Similarity	NPC174788
0.7031	Intermediate Similarity	NPC318020
0.7026	Intermediate Similarity	NPC471979
0.7026	Intermediate Similarity	NPC129909
0.7026	Intermediate Similarity	NPC227824
0.7025	Intermediate Similarity	NPC85273
0.702	Intermediate Similarity	NPC477549
0.7018	Intermediate Similarity	NPC322043
0.7018	Intermediate Similarity	NPC327373
0.7013	Intermediate Similarity	NPC61435
0.7009	Intermediate Similarity	NPC20593
0.7004	Intermediate Similarity	NPC24864
0.7004	Intermediate Similarity	NPC477588
0.7004	Intermediate Similarity	NPC477590
0.7004	Intermediate Similarity	NPC477585
0.7004	Intermediate Similarity	NPC477586
0.7	Intermediate Similarity	NPC309498
0.6992	Remote Similarity	NPC284685
0.6992	Remote Similarity	NPC162812
0.6992	Remote Similarity	NPC28945
0.6992	Remote Similarity	NPC320748
0.6992	Remote Similarity	NPC324245
0.6988	Remote Similarity	NPC208364
0.6988	Remote Similarity	NPC188400
0.6987	Remote Similarity	NPC245816
0.6987	Remote Similarity	NPC476138
0.698	Remote Similarity	NPC170751
0.6975	Remote Similarity	NPC328559
0.6974	Remote Similarity	NPC219963
0.6967	Remote Similarity	NPC171409
0.6967	Remote Similarity	NPC53069
0.6967	Remote Similarity	NPC96405
0.6967	Remote Similarity	NPC202768
0.6967	Remote Similarity	NPC296482
0.6958	Remote Similarity	NPC25442
0.6958	Remote Similarity	NPC12944
0.6958	Remote Similarity	NPC470500
0.6951	Remote Similarity	NPC30570
0.6941	Remote Similarity	NPC329631
0.6941	Remote Similarity	NPC323752
0.6939	Remote Similarity	NPC469592
0.6939	Remote Similarity	NPC471080
0.6935	Remote Similarity	NPC193267
0.6935	Remote Similarity	NPC213530
0.6934	Remote Similarity	NPC478012
0.6934	Remote Similarity	NPC478011
0.6929	Remote Similarity	NPC129897
0.6929	Remote Similarity	NPC476999
0.6926	Remote Similarity	NPC314056
0.6926	Remote Similarity	NPC315634
0.6926	Remote Similarity	NPC477587
0.6926	Remote Similarity	NPC477589
0.6926	Remote Similarity	NPC100734
0.6926	Remote Similarity	NPC88923
0.6926	Remote Similarity	NPC476995
0.692	Remote Similarity	NPC476516
0.692	Remote Similarity	NPC59033
0.692	Remote Similarity	NPC216612

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 NPC472436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	579
0.2-0.3	1029
0.3-0.4	1953
0.4-0.5	2759
0.5-0.6	1868
0.6-0.7	628
0.7-0.8	62
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7992	Intermediate Similarity	NPD8370	Discontinued
0.7868	Intermediate Similarity	NPD8421	Discontinued
0.7801	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD5640	Discontinued
0.7542	Intermediate Similarity	NPD8479	Phase 2
0.7531	Intermediate Similarity	NPD7426	Phase 1
0.752	Intermediate Similarity	NPD7796	Approved
0.752	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD7797	Approved
0.752	Intermediate Similarity	NPD5482	Discontinued
0.749	Intermediate Similarity	NPD8326	Phase 3
0.749	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD8325	Phase 3
0.7479	Intermediate Similarity	NPD4897	Phase 2
0.7458	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD6716	Phase 1
0.7347	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD8246	Approved
0.7336	Intermediate Similarity	NPD8247	Approved
0.7295	Intermediate Similarity	NPD6298	Discontinued
0.7295	Intermediate Similarity	NPD5506	Approved
0.7295	Intermediate Similarity	NPD5507	Approved
0.7291	Intermediate Similarity	NPD3006	Discontinued
0.7288	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7558	Phase 2
0.7265	Intermediate Similarity	NPD8356	Approved
0.725	Intermediate Similarity	NPD7069	Discontinued
0.7245	Intermediate Similarity	NPD5450	Discontinued
0.7218	Intermediate Similarity	NPD8430	Approved
0.7218	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD4086	Phase 1
0.7217	Intermediate Similarity	NPD4372	Phase 1
0.7202	Intermediate Similarity	NPD4989	Phase 2
0.7202	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8468	Phase 2
0.7192	Intermediate Similarity	NPD7859	Phase 2
0.7181	Intermediate Similarity	NPD8101	Phase 3
0.7176	Intermediate Similarity	NPD6961	Discontinued
0.7173	Intermediate Similarity	NPD4035	Approved
0.7173	Intermediate Similarity	NPD4038	Approved
0.7173	Intermediate Similarity	NPD4039	Approved
0.7173	Intermediate Similarity	NPD4034	Approved
0.7173	Intermediate Similarity	NPD31	Approved
0.7173	Intermediate Similarity	NPD4037	Approved
0.7173	Intermediate Similarity	NPD4033	Approved
0.7173	Intermediate Similarity	NPD32	Approved
0.7173	Intermediate Similarity	NPD4122	Approved
0.7173	Intermediate Similarity	NPD4036	Approved
0.716	Intermediate Similarity	NPD5022	Discontinued
0.7143	Intermediate Similarity	NPD6569	Phase 2
0.7132	Intermediate Similarity	NPD8375	Approved
0.7126	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3477	Phase 2
0.7124	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD8463	Approved
0.7094	Intermediate Similarity	NPD6206	Phase 1
0.7077	Intermediate Similarity	NPD8371	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8359	Phase 2
0.7066	Intermediate Similarity	NPD8100	Phase 3
0.7056	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6550	Discontinued
0.7045	Intermediate Similarity	NPD8255	Phase 2
0.7045	Intermediate Similarity	NPD8049	Phase 2
0.7043	Intermediate Similarity	NPD7417	Discontinued
0.7027	Intermediate Similarity	NPD7967	Discontinued
0.7026	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7853	Phase 2
0.7013	Intermediate Similarity	NPD4334	Discontinued
0.7008	Intermediate Similarity	NPD4373	Phase 2
0.7004	Intermediate Similarity	NPD6974	Phase 3
0.7004	Intermediate Similarity	NPD7886	Phase 2
0.7004	Intermediate Similarity	NPD7885	Phase 2
0.6996	Remote Similarity	NPD5066	Phase 2
0.6996	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5067	Phase 2
0.6993	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7955	Approved
0.6992	Remote Similarity	NPD7956	Approved
0.6987	Remote Similarity	NPD5487	Phase 1
0.6985	Remote Similarity	NPD5922	Phase 3
0.6983	Remote Similarity	NPD3321	Discontinued
0.698	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5512	Phase 3
0.6972	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7674	Phase 3
0.6972	Remote Similarity	NPD7675	Phase 3
0.6972	Remote Similarity	NPD7603	Discontinued
0.6972	Remote Similarity	NPD3263	Phase 3
0.6971	Remote Similarity	NPD7222	Phase 2
0.697	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6969	Remote Similarity	NPD7031	Phase 1
0.6967	Remote Similarity	NPD3816	Phase 1
0.6967	Remote Similarity	NPD3815	Phase 1
0.6964	Remote Similarity	NPD6568	Discontinued
0.6964	Remote Similarity	NPD5948	Phase 2
0.6957	Remote Similarity	NPD8374	Phase 3
0.695	Remote Similarity	NPD6517	Phase 3
0.695	Remote Similarity	NPD8117	Approved
0.695	Remote Similarity	NPD8116	Phase 3
0.6948	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8324	Phase 2
0.6942	Remote Similarity	NPD7467	Discontinued
0.6941	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7803	Approved
0.692	Remote Similarity	NPD6261	Phase 3
0.692	Remote Similarity	NPD1856	Discontinued
0.6914	Remote Similarity	NPD8329	Phase 3
0.6911	Remote Similarity	NPD5293	Phase 2
0.6908	Remote Similarity	NPD6276	Discontinued
0.6905	Remote Similarity	NPD8289	Discontinued
0.6903	Remote Similarity	NPD6531	Approved
0.6903	Remote Similarity	NPD6530	Approved
0.6903	Remote Similarity	NPD7708	Approved
0.6902	Remote Similarity	NPD4885	Approved
0.6901	Remote Similarity	NPD1392	Approved
0.6898	Remote Similarity	NPD5866	Approved
0.6897	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1034	Phase 3
0.6895	Remote Similarity	NPD7395	Discontinued
0.6895	Remote Similarity	NPD5632	Approved
0.6892	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6248	Phase 2
0.6891	Remote Similarity	NPD6249	Phase 2
0.689	Remote Similarity	NPD4952	Phase 3
0.6887	Remote Similarity	NPD4454	Phase 2
0.6883	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6494	Phase 2
0.6875	Remote Similarity	NPD7924	Phase 2
0.6875	Remote Similarity	NPD7925	Phase 2
0.6873	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5416	Discontinued
0.6853	Remote Similarity	NPD5444	Phase 1
0.6851	Remote Similarity	NPD4315	Phase 2
0.685	Remote Similarity	NPD5559	Phase 2
0.6846	Remote Similarity	NPD5513	Phase 2
0.6846	Remote Similarity	NPD6669	Phase 2
0.6842	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.684	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7180	Phase 3
0.684	Remote Similarity	NPD5850	Phase 3
0.684	Remote Similarity	NPD5116	Phase 1
0.6838	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6023	Discontinued
0.6836	Remote Similarity	NPD5018	Phase 3
0.6826	Remote Similarity	NPD4203	Approved
0.6826	Remote Similarity	NPD4204	Approved
0.6824	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.682	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4369	Phase 2
0.6818	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8442	Discontinued
0.6815	Remote Similarity	NPD5612	Discontinued
0.6813	Remote Similarity	NPD4923	Phase 1
0.681	Remote Similarity	NPD4889	Approved
0.6805	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6801	Remote Similarity	NPD3343	Phase 3
0.68	Remote Similarity	NPD7194	Discontinued
0.6797	Remote Similarity	NPD6962	Phase 2
0.679	Remote Similarity	NPD7001	Phase 3
0.679	Remote Similarity	NPD3003	Approved
0.6789	Remote Similarity	NPD4131	Phase 3
0.6786	Remote Similarity	NPD8459	Approved
0.6786	Remote Similarity	NPD8460	Approved
0.6784	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6963	Approved
0.6783	Remote Similarity	NPD6964	Approved
0.6782	Remote Similarity	NPD6790	Phase 1
0.6779	Remote Similarity	NPD7963	Phase 3
0.6774	Remote Similarity	NPD5903	Approved
0.6774	Remote Similarity	NPD5902	Approved
0.6774	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6456	Discontinued
0.6763	Remote Similarity	NPD8466	Approved
0.6763	Remote Similarity	NPD8465	Approved
0.6763	Remote Similarity	NPD8467	Approved
0.6762	Remote Similarity	NPD7453	Approved
0.6762	Remote Similarity	NPD5429	Discontinued
0.6762	Remote Similarity	NPD7452	Approved
0.676	Remote Similarity	NPD4429	Discontinued
0.6758	Remote Similarity	NPD1659	Phase 1
0.6758	Remote Similarity	NPD8512	Phase 3
0.6756	Remote Similarity	NPD7022	Phase 2
0.6755	Remote Similarity	NPD8102	Discontinued
0.6755	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7994	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