NPASS Compound

Structure

NPC253580 OpenBabel07101718302D 45 53 0 0 1 0 0 0 0 0999 V2000 -8.0590 -2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1105 -3.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5949 -1.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1930 -1.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5987 -2.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9098 -3.6919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1975 -4.3937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3620 0.0289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6583 -2.7241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2335 -4.1277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9386 -5.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9441 -5.3596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6123 -0.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8628 -2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1930 -3.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5458 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6741 0.3424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9888 0.1490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7289 -1.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1930 -4.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4609 -3.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2442 -2.1032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4609 -1.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3269 -2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3269 -3.0725 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6943 -2.4580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2470 -1.5637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8628 -3.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5264 -4.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9819 -3.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7184 -2.7235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5949 -3.0725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5374 -4.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1197 -3.7416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1252 -3.6371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7289 -3.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2581 -1.7127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3653 -0.9309 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0871 -1.3054 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5210 -4.5506 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0943 -2.6992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5949 -2.0725 0.0000 N 0 3 1 0 0 0 0 0 0 0 0 0 -8.0590 -5.0725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4571 -4.3416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 4 24 2 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 16 1 0 0 0 0 8 17 1 0 0 0 0 9 26 2 0 0 0 0 10 30 2 0 0 0 0 11 12 2 0 0 0 0 11 29 1 0 0 0 0 12 33 1 0 0 0 0 13 18 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 16 39 1 0 0 0 0 17 41 1 0 0 0 0 18 41 1 0 0 0 0 19 43 1 0 0 0 0 20 44 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 0 0 0 0 22 31 1 0 0 0 0 22 39 1 0 0 0 0 23 24 1 0 0 0 0 23 43 1 0 0 0 0 24 25 1 0 0 0 0 25 15 1 6 0 0 0 26 27 1 0 0 0 0 26 30 1 0 0 0 0 27 37 2 0 0 0 0 28 34 1 0 0 0 0 28 36 2 0 0 0 0 29 34 2 0 0 0 0 29 40 1 0 0 0 0 30 42 1 0 0 0 0 31 35 1 6 0 0 0 31 42 1 0 0 0 0 32 36 1 0 0 0 0 32 43 1 1 0 0 0 33 35 2 0 0 0 0 33 45 1 0 0 0 0 34 35 1 0 0 0 0 36 40 1 0 0 0 0 37 38 1 0 0 0 0 37 42 1 0 0 0 0 38 39 1 1 0 0 0 38 41 1 0 0 0 0 39 5 1 6 0 0 0 43 3 1 6 0 0 0 M CHG 1 43 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	605.39
Volume:	645.249
LogP:	4.002
LogD:	4.465
LogS:	-1.002
# Rotatable Bonds:	4
TPSA:	64.42
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	9
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.169
Synthetic Accessibility Score:	5.29
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.865
MDCK Permeability:	1.0127643690793775e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.917
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	91.6237564086914%
Volume Distribution (VD):	1.405
Pgp-substrate:	6.046600818634033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.23
CYP2D6-inhibitor:	0.265
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.402
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	4.305
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.872
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.215
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.106
Carcinogencity:	0.193
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.66

Download Data

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

Natural Product: NPC253580

Natural Product ID:	NPC253580
*Common Name:**	Bisnicalaterine B
IUPAC Name:	n.a.
Synonyms:	Bisnicalaterine B; Bisnicalaterine C
Standard InCHIKey:	VOTSDECPXOPQEF-RDIXYSTHSA-O
Standard InCHI:	InChI=1S/C39H48N4O2/c1-4-24-23-43(3)19-14-28-34-29(40-36(28)32(43)21-25(24)15-20-44)11-12-33(45)35(34)31-22-39(5-2)16-8-17-41-18-13-27-26-9-6-7-10-30(26)42(31)37(27)38(39)41/h4,6-7,9-12,25,31-32,38,40,44H,5,8,13-23H2,1-3H3/p+1/b24-4-/t25-,31-,32+,38-,39+,43+/m0/s1
SMILES:	OCC[C@H]1C[C@@H]2c3[nH]c4c(c3CC[N@@+]2(C/C/1=C/C)C)c(c(cc4)O)[C@@H]1C[C@@]2(CC)CCCN3[C@H]2c2n1c1ccccc1c2CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1778841
PubChem CID:	46846152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002671] Eburnan-type alkaloids

*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
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19388660]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21524573]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28362501]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	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	4
Others	2

Activity Type	# Activity
Cell Line	2
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[486889]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[486890]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1130.0	nM	PMID[486889]
NPT2	Others	Unspecified		Ratio IC50	>	44.0	n.a.	PMID[486889]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	50.0	nM	PMID[486890]
NPT2	Others	Unspecified		Ratio IC50	>	1000.0	n.a.	PMID[486890]

☑ 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 NPC253580 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	516
0.1-0.2	2503
0.2-0.3	12278
0.3-0.4	14631
0.4-0.5	7478
0.5-0.6	3205
0.6-0.7	1629
0.7-0.8	421
0.8-0.85	24
0.85-0.9	10
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9755	High Similarity	NPC470126
0.8762	High Similarity	NPC249040
0.8585	High Similarity	NPC476041
0.8585	High Similarity	NPC304926
0.8517	High Similarity	NPC476116
0.8387	Intermediate Similarity	NPC162748
0.8364	Intermediate Similarity	NPC183407
0.8235	Intermediate Similarity	NPC6215
0.8219	Intermediate Similarity	NPC280272
0.8066	Intermediate Similarity	NPC475070
0.8062	Intermediate Similarity	NPC295228
0.8047	Intermediate Similarity	NPC5145
0.8047	Intermediate Similarity	NPC475422
0.8035	Intermediate Similarity	NPC477861
0.8	Intermediate Similarity	NPC81175
0.7961	Intermediate Similarity	NPC106833
0.7961	Intermediate Similarity	NPC469497
0.7953	Intermediate Similarity	NPC87755
0.7946	Intermediate Similarity	NPC2497
0.7932	Intermediate Similarity	NPC478080
0.7913	Intermediate Similarity	NPC128751
0.7913	Intermediate Similarity	NPC246700
0.7913	Intermediate Similarity	NPC41679
0.7906	Intermediate Similarity	NPC17437
0.7888	Intermediate Similarity	NPC478082
0.7888	Intermediate Similarity	NPC477067
0.7885	Intermediate Similarity	NPC476451
0.7867	Intermediate Similarity	NPC214980
0.786	Intermediate Similarity	NPC472111
0.782	Intermediate Similarity	NPC153042
0.7793	Intermediate Similarity	NPC477609
0.7773	Intermediate Similarity	NPC471080
0.7773	Intermediate Similarity	NPC469592
0.7773	Intermediate Similarity	NPC478074
0.7768	Intermediate Similarity	NPC477066
0.7767	Intermediate Similarity	NPC223427
0.7735	Intermediate Similarity	NPC478081
0.7729	Intermediate Similarity	NPC477531
0.7719	Intermediate Similarity	NPC252251
0.7718	Intermediate Similarity	NPC472294
0.7703	Intermediate Similarity	NPC469928
0.7686	Intermediate Similarity	NPC209174
0.7679	Intermediate Similarity	NPC471891
0.7673	Intermediate Similarity	NPC472123
0.767	Intermediate Similarity	NPC19679
0.7644	Intermediate Similarity	NPC132642
0.7642	Intermediate Similarity	NPC477608
0.7642	Intermediate Similarity	NPC314954
0.7637	Intermediate Similarity	NPC469734
0.7634	Intermediate Similarity	NPC469594
0.763	Intermediate Similarity	NPC99666
0.7615	Intermediate Similarity	NPC475841
0.7615	Intermediate Similarity	NPC474145
0.7598	Intermediate Similarity	NPC473185
0.7598	Intermediate Similarity	NPC476492
0.7591	Intermediate Similarity	NPC469589
0.7585	Intermediate Similarity	NPC473312
0.758	Intermediate Similarity	NPC193777
0.7568	Intermediate Similarity	NPC294620
0.7565	Intermediate Similarity	NPC33949
0.756	Intermediate Similarity	NPC171171
0.7557	Intermediate Similarity	NPC126066
0.7546	Intermediate Similarity	NPC329793
0.7534	Intermediate Similarity	NPC477610
0.7525	Intermediate Similarity	NPC317430
0.7524	Intermediate Similarity	NPC88363
0.7523	Intermediate Similarity	NPC208284
0.7522	Intermediate Similarity	NPC193267
0.7522	Intermediate Similarity	NPC213530
0.7521	Intermediate Similarity	NPC81939
0.7521	Intermediate Similarity	NPC477549
0.7512	Intermediate Similarity	NPC314002
0.7511	Intermediate Similarity	NPC473540
0.75	Intermediate Similarity	NPC472108
0.75	Intermediate Similarity	NPC139291
0.749	Intermediate Similarity	NPC475666
0.7489	Intermediate Similarity	NPC477607
0.7489	Intermediate Similarity	NPC470500
0.7488	Intermediate Similarity	NPC77555
0.7478	Intermediate Similarity	NPC227908
0.7466	Intermediate Similarity	NPC475910
0.7464	Intermediate Similarity	NPC204717
0.7457	Intermediate Similarity	NPC326363
0.7453	Intermediate Similarity	NPC469501
0.7453	Intermediate Similarity	NPC469470
0.7444	Intermediate Similarity	NPC9894
0.7443	Intermediate Similarity	NPC476098
0.744	Intermediate Similarity	NPC133261
0.7421	Intermediate Similarity	NPC53344
0.7421	Intermediate Similarity	NPC166492
0.7421	Intermediate Similarity	NPC473362
0.7416	Intermediate Similarity	NPC220765
0.7416	Intermediate Similarity	NPC472110
0.7416	Intermediate Similarity	NPC472109
0.7415	Intermediate Similarity	NPC474409
0.7412	Intermediate Similarity	NPC472099
0.7411	Intermediate Similarity	NPC48353
0.7411	Intermediate Similarity	NPC94157
0.7404	Intermediate Similarity	NPC472105
0.7404	Intermediate Similarity	NPC187827
0.7404	Intermediate Similarity	NPC325976
0.7393	Intermediate Similarity	NPC469554
0.7388	Intermediate Similarity	NPC478083
0.7383	Intermediate Similarity	NPC324149
0.738	Intermediate Similarity	NPC477532
0.7371	Intermediate Similarity	NPC95783
0.735	Intermediate Similarity	NPC475253
0.7346	Intermediate Similarity	NPC94943
0.7342	Intermediate Similarity	NPC473183
0.7336	Intermediate Similarity	NPC477533
0.7333	Intermediate Similarity	NPC472098
0.7331	Intermediate Similarity	NPC478010
0.7319	Intermediate Similarity	NPC101543
0.7317	Intermediate Similarity	NPC474897
0.7316	Intermediate Similarity	NPC130570
0.7313	Intermediate Similarity	NPC330009
0.7308	Intermediate Similarity	NPC326575
0.7306	Intermediate Similarity	NPC329982
0.7306	Intermediate Similarity	NPC176538
0.7304	Intermediate Similarity	NPC471506
0.7299	Intermediate Similarity	NPC190007
0.7293	Intermediate Similarity	NPC473179
0.7284	Intermediate Similarity	NPC313884
0.7284	Intermediate Similarity	NPC98371
0.7284	Intermediate Similarity	NPC471564
0.7281	Intermediate Similarity	NPC205403
0.7281	Intermediate Similarity	NPC251090
0.7277	Intermediate Similarity	NPC229173
0.7273	Intermediate Similarity	NPC72980
0.7269	Intermediate Similarity	NPC250835
0.7261	Intermediate Similarity	NPC86078
0.726	Intermediate Similarity	NPC476167
0.726	Intermediate Similarity	NPC24594
0.726	Intermediate Similarity	NPC472122
0.7257	Intermediate Similarity	NPC473184
0.7257	Intermediate Similarity	NPC473180
0.7253	Intermediate Similarity	NPC202503
0.7253	Intermediate Similarity	NPC319232
0.7253	Intermediate Similarity	NPC24370
0.7253	Intermediate Similarity	NPC214142
0.7252	Intermediate Similarity	NPC47059
0.7252	Intermediate Similarity	NPC264166
0.7252	Intermediate Similarity	NPC118832
0.7252	Intermediate Similarity	NPC274291
0.7252	Intermediate Similarity	NPC165349
0.7252	Intermediate Similarity	NPC329708
0.7251	Intermediate Similarity	NPC212535
0.7249	Intermediate Similarity	NPC96321
0.7248	Intermediate Similarity	NPC232130
0.7248	Intermediate Similarity	NPC474188
0.7246	Intermediate Similarity	NPC207686
0.7246	Intermediate Similarity	NPC474192
0.7246	Intermediate Similarity	NPC475720
0.7244	Intermediate Similarity	NPC167860
0.7244	Intermediate Similarity	NPC471304
0.7244	Intermediate Similarity	NPC123976
0.724	Intermediate Similarity	NPC211813
0.7237	Intermediate Similarity	NPC152768
0.7237	Intermediate Similarity	NPC148183
0.7237	Intermediate Similarity	NPC477110
0.7237	Intermediate Similarity	NPC251936
0.7237	Intermediate Similarity	NPC170114
0.7235	Intermediate Similarity	NPC276517
0.7235	Intermediate Similarity	NPC195314
0.7229	Intermediate Similarity	NPC310118
0.7225	Intermediate Similarity	NPC475602
0.7225	Intermediate Similarity	NPC184964
0.7222	Intermediate Similarity	NPC261251
0.7222	Intermediate Similarity	NPC110151
0.7215	Intermediate Similarity	NPC192315
0.7215	Intermediate Similarity	NPC52557
0.7215	Intermediate Similarity	NPC473182
0.7215	Intermediate Similarity	NPC265576
0.7205	Intermediate Similarity	NPC314552
0.7204	Intermediate Similarity	NPC314394
0.72	Intermediate Similarity	NPC201697
0.7196	Intermediate Similarity	NPC46580
0.7195	Intermediate Similarity	NPC476493
0.7194	Intermediate Similarity	NPC478009
0.7193	Intermediate Similarity	NPC470549
0.7192	Intermediate Similarity	NPC81229
0.7192	Intermediate Similarity	NPC255229
0.7191	Intermediate Similarity	NPC100547
0.7189	Intermediate Similarity	NPC307963
0.7188	Intermediate Similarity	NPC270918
0.7183	Intermediate Similarity	NPC476319
0.7175	Intermediate Similarity	NPC285558
0.7174	Intermediate Similarity	NPC473310
0.717	Intermediate Similarity	NPC176127
0.7169	Intermediate Similarity	NPC243834
0.7169	Intermediate Similarity	NPC156704
0.7169	Intermediate Similarity	NPC70956
0.7168	Intermediate Similarity	NPC199667
0.7162	Intermediate Similarity	NPC74969
0.7161	Intermediate Similarity	NPC322135
0.7161	Intermediate Similarity	NPC223409
0.7161	Intermediate Similarity	NPC95240
0.7156	Intermediate Similarity	NPC477111
0.7154	Intermediate Similarity	NPC315467
0.7149	Intermediate Similarity	NPC39092

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 NPC253580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	600
0.2-0.3	827
0.3-0.4	1617
0.4-0.5	2717
0.5-0.6	2254
0.6-0.7	767
0.7-0.8	113
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
0.7941	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD8358	Approved
0.7713	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7678	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD7112	Discontinued
0.7617	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5530	Phase 1
0.7581	Intermediate Similarity	NPD8395	Approved
0.7581	Intermediate Similarity	NPD8396	Approved
0.758	Intermediate Similarity	NPD7222	Phase 2
0.7577	Intermediate Similarity	NPD7221	Approved
0.7577	Intermediate Similarity	NPD7219	Approved
0.757	Intermediate Similarity	NPD7948	Phase 1
0.75	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD5658	Approved
0.7436	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4511	Phase 1
0.7426	Intermediate Similarity	NPD8016	Phase 3
0.7426	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2175	Phase 3
0.7419	Intermediate Similarity	NPD2176	Approved
0.7419	Intermediate Similarity	NPD2177	Approved
0.7387	Intermediate Similarity	NPD2916	Discontinued
0.738	Intermediate Similarity	NPD7726	Phase 1
0.7368	Intermediate Similarity	NPD7194	Discontinued
0.7366	Intermediate Similarity	NPD5936	Approved
0.7366	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5939	Approved
0.7342	Intermediate Similarity	NPD7453	Approved
0.7342	Intermediate Similarity	NPD7452	Approved
0.7325	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6978	Phase 2
0.7284	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2383	Phase 1
0.7253	Intermediate Similarity	NPD7603	Discontinued
0.7252	Intermediate Similarity	NPD32	Approved
0.7252	Intermediate Similarity	NPD31	Approved
0.7252	Intermediate Similarity	NPD4034	Approved
0.7252	Intermediate Similarity	NPD4122	Approved
0.7252	Intermediate Similarity	NPD4036	Approved
0.7252	Intermediate Similarity	NPD4035	Approved
0.7252	Intermediate Similarity	NPD4037	Approved
0.7252	Intermediate Similarity	NPD4038	Approved
0.7252	Intermediate Similarity	NPD4039	Approved
0.7252	Intermediate Similarity	NPD4033	Approved
0.7237	Intermediate Similarity	NPD5612	Discontinued
0.7235	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD3003	Approved
0.7215	Intermediate Similarity	NPD7558	Phase 2
0.7212	Intermediate Similarity	NPD4502	Phase 2
0.7205	Intermediate Similarity	NPD5164	Discontinued
0.7204	Intermediate Similarity	NPD7867	Phase 1
0.7189	Intermediate Similarity	NPD1038	Approved
0.7188	Intermediate Similarity	NPD6290	Phase 2
0.7171	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5507	Approved
0.7155	Intermediate Similarity	NPD5506	Approved
0.7154	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4601	Approved
0.7149	Intermediate Similarity	NPD4600	Approved
0.7111	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3330	Phase 1
0.7098	Intermediate Similarity	NPD4795	Phase 2
0.7085	Intermediate Similarity	NPD6975	Discontinued
0.708	Intermediate Similarity	NPD6376	Discontinued
0.7075	Intermediate Similarity	NPD6595	Phase 3
0.7072	Intermediate Similarity	NPD484	Approved
0.7068	Intermediate Similarity	NPD8442	Discontinued
0.7067	Intermediate Similarity	NPD1325	Approved
0.7067	Intermediate Similarity	NPD1326	Approved
0.7067	Intermediate Similarity	NPD8403	Phase 1
0.7062	Intermediate Similarity	NPD6159	Phase 2
0.7048	Intermediate Similarity	NPD5065	Approved
0.7043	Intermediate Similarity	NPD5902	Approved
0.7043	Intermediate Similarity	NPD5903	Approved
0.7032	Intermediate Similarity	NPD802	Phase 2
0.7032	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8364	Approved
0.7031	Intermediate Similarity	NPD8363	Approved
0.7029	Intermediate Similarity	NPD7797	Approved
0.7029	Intermediate Similarity	NPD4885	Approved
0.7029	Intermediate Similarity	NPD7796	Approved
0.7023	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD3931	Approved
0.7009	Intermediate Similarity	NPD3928	Approved
0.6992	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8244	Phase 2
0.6966	Remote Similarity	NPD5930	Phase 3
0.6962	Remote Similarity	NPD7674	Phase 3
0.6962	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7675	Phase 3
0.6959	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5140	Approved
0.6957	Remote Similarity	NPD5138	Approved
0.6953	Remote Similarity	NPD6985	Discontinued
0.6951	Remote Similarity	NPD3814	Phase 1
0.6951	Remote Similarity	NPD1768	Approved
0.6946	Remote Similarity	NPD7824	Approved
0.6944	Remote Similarity	NPD6227	Discontinued
0.6934	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5596	Phase 2
0.693	Remote Similarity	NPD7666	Phase 3
0.693	Remote Similarity	NPD7665	Phase 2
0.6923	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6455	Phase 3
0.692	Remote Similarity	NPD1740	Approved
0.692	Remote Similarity	NPD1739	Approved
0.6907	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5559	Phase 2
0.6897	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6158	Phase 2
0.6897	Remote Similarity	NPD4897	Phase 2
0.6897	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6492	Phase 2
0.6885	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4204	Approved
0.6884	Remote Similarity	NPD4203	Approved
0.6883	Remote Similarity	NPD3815	Phase 1
0.6883	Remote Similarity	NPD3816	Phase 1
0.6883	Remote Similarity	NPD8093	Discontinued
0.6881	Remote Similarity	NPD8431	Approved
0.6875	Remote Similarity	NPD6456	Discontinued
0.6869	Remote Similarity	NPD4079	Approved
0.6869	Remote Similarity	NPD4076	Approved
0.6866	Remote Similarity	NPD2762	Phase 2
0.6864	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5913	Phase 3
0.6862	Remote Similarity	NPD7731	Approved
0.6862	Remote Similarity	NPD7730	Approved
0.686	Remote Similarity	NPD7950	Approved
0.686	Remote Similarity	NPD7952	Approved
0.686	Remote Similarity	NPD7951	Approved
0.686	Remote Similarity	NPD7953	Approved
0.686	Remote Similarity	NPD7790	Approved
0.686	Remote Similarity	NPD7791	Approved
0.686	Remote Similarity	NPD7789	Approved
0.6856	Remote Similarity	NPD7672	Approved
0.6856	Remote Similarity	NPD7671	Approved
0.6856	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2380	Approved
0.6854	Remote Similarity	NPD2381	Approved
0.6854	Remote Similarity	NPD2382	Approved
0.6853	Remote Similarity	NPD8094	Discontinued
0.6851	Remote Similarity	NPD3875	Discontinued
0.685	Remote Similarity	NPD7955	Approved
0.685	Remote Similarity	NPD7956	Approved
0.6849	Remote Similarity	NPD7271	Approved
0.6849	Remote Similarity	NPD4401	Phase 2
0.6849	Remote Similarity	NPD4403	Phase 3
0.6849	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4418	Discontinued
0.6828	Remote Similarity	NPD4886	Phase 2
0.6828	Remote Similarity	NPD4044	Discontinued
0.6826	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3505	Approved
0.6822	Remote Similarity	NPD3506	Approved
0.6818	Remote Similarity	NPD6281	Approved
0.6818	Remote Similarity	NPD7181	Phase 3
0.6818	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6230	Discontinued
0.6814	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD2882	Phase 1
0.6812	Remote Similarity	NPD1392	Approved
0.6806	Remote Similarity	NPD8466	Approved
0.6806	Remote Similarity	NPD8465	Approved
0.6806	Remote Similarity	NPD8467	Approved
0.6805	Remote Similarity	NPD6968	Phase 2
0.6805	Remote Similarity	NPD6969	Phase 2
0.6798	Remote Similarity	NPD5426	Phase 3
0.6792	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6494	Phase 2
0.6786	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3763	Approved
0.678	Remote Similarity	NPD3402	Phase 1
0.6774	Remote Similarity	NPD7592	Phase 2
0.6774	Remote Similarity	NPD6572	Phase 2
0.6774	Remote Similarity	NPD6573	Phase 3
0.6773	Remote Similarity	NPD8101	Phase 3
0.6769	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5067	Phase 2
0.6767	Remote Similarity	NPD7470	Discontinued
0.6767	Remote Similarity	NPD5066	Phase 2
0.6761	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6531	Approved
0.6758	Remote Similarity	NPD6530	Approved
0.6758	Remote Similarity	NPD7708	Approved
0.6756	Remote Similarity	NPD53	Approved
0.6756	Remote Similarity	NPD7777	Approved
0.6756	Remote Similarity	NPD7778	Approved
0.6751	Remote Similarity	NPD7678	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data