NPASS Compound

Structure

NPC473040 OpenBabel07101718192D 41 48 0 0 1 0 0 0 0 0999 V2000 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7894 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4073 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8684 -3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4562 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4073 -3.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5411 -0.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2163 -4.1569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7894 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4562 -3.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 0.9230 -0.5878 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 3 19 1 0 0 0 0 4 22 1 0 0 0 0 5 7 1 0 0 0 0 5 21 1 0 0 0 0 6 8 1 0 0 0 0 6 20 1 0 0 0 0 7 27 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 9 32 1 0 0 0 0 10 41 1 0 0 0 0 11 18 2 0 0 0 0 11 25 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 30 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 37 1 0 0 0 0 16 33 2 0 0 0 0 17 1 1 6 0 0 0 17 38 1 0 0 0 0 18 20 1 0 0 0 0 19 28 1 1 0 0 0 20 27 1 1 0 0 0 21 22 1 0 0 0 0 21 28 1 1 0 0 0 22 29 1 6 0 0 0 23 12 1 1 0 0 0 23 24 1 0 0 0 0 23 39 1 0 0 0 0 24 14 1 6 0 0 0 24 40 1 0 0 0 0 25 34 2 0 0 0 0 25 37 1 0 0 0 0 26 31 1 6 0 0 0 26 38 1 0 0 0 0 26 39 1 0 0 0 0 27 29 1 1 0 0 0 28 16 1 1 0 0 0 29 35 1 1 0 0 0 30 31 1 1 0 0 0 30 32 1 0 0 0 0 30 41 1 0 0 0 0 31 36 1 1 0 0 0 31 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	589.27
Volume:	568.199
LogP:	3.454
LogD:	2.97
LogS:	-4.076
# Rotatable Bonds:	2
TPSA:	130.62
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	6.538
Fsp3:	0.839
Lipinski Rule-of-5:	Accepted
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:	-5.499
MDCK Permeability:	1.0387600923422724e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.907
Human Intestinal Absorption (HIA):	0.571
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98
Plasma Protein Binding (PPB):	62.83154296875%
Volume Distribution (VD):	1.116
Pgp-substrate:	27.450990676879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.353
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.868

ADMET: Excretion

Clearance (CL):	4.241
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.701
Human Hepatotoxicity (H-HT):	0.776
Drug-inuced Liver Injury (DILI):	0.317
AMES Toxicity:	0.932
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.931
Carcinogencity:	0.708
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC473040

Natural Product ID:	NPC473040
*Common Name:**	YLDBWOUPHZGCJG-IGACXKNBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YLDBWOUPHZGCJG-IGACXKNBSA-N
Standard InCHI:	InChI=1S/C31H43NO8S/c1-17-13-30(32-9-10-41-30)31(36)26(38-17)39-23-12-19-3-4-22-21(28(19,16-33)14-24(23)40-31)5-7-27(2)20(6-8-29(22,27)35)18-11-25(34)37-15-18/h11,16-17,19-24,26,32,35-36H,3-10,12-15H2,1-2H3/t17-,19+,20-,21+,22-,23-,24-,26+,27-,28-,29+,30+,31-/m1/s1
SMILES:	C[C@@H]1C[C@]2([C@]3([C@@H](O1)O[C@@H]1C[C@@H]4CC[C@@H]5[C@H](CC[C@]6(C)[C@H](CC[C@]56O)C5=CC(=O)OC5)[C@]4(C[C@H]1O3)C=O)O)NCCS2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL360322
PubChem CID:	44387915
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

*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
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	root barks	n.a.	n.a.	PMID[15689169]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933890]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	root	n.a.	PMID[19052526]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28817274]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31967821]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32649211]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548837]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27807	Calotropis procera	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	6
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT933	Cell Line	U373 MG	Homo sapiens	IC50	=	32.0	nM	PMID[474408]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	27.0	nM	PMID[474408]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	17.0	nM	PMID[474408]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5.0	nM	PMID[474408]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.0	nM	PMID[474408]
NPT32	Organism	Mus musculus	Mus musculus	MTD	=	1.25	mg kg-1	PMID[474408]
NPT25172	SINGLE PROTEIN	Neurogenic locus notch homolog protein 1	Homo sapiens	IC50	=	2000.0	nM	PMID[474409]

☑ 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 NPC473040 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	199
0.1-0.2	1353
0.2-0.3	6246
0.3-0.4	16499
0.4-0.5	11189
0.5-0.6	5161
0.6-0.7	1898
0.7-0.8	146
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9125	High Similarity	NPC470094
0.8797	High Similarity	NPC163365
0.8418	Intermediate Similarity	NPC473208
0.7748	Intermediate Similarity	NPC91
0.7697	Intermediate Similarity	NPC16569
0.7697	Intermediate Similarity	NPC159338
0.7697	Intermediate Similarity	NPC253456
0.7647	Intermediate Similarity	NPC19124
0.7647	Intermediate Similarity	NPC42670
0.7647	Intermediate Similarity	NPC93416
0.7597	Intermediate Similarity	NPC157817
0.7597	Intermediate Similarity	NPC142756
0.7597	Intermediate Similarity	NPC104585
0.7597	Intermediate Similarity	NPC477709
0.7597	Intermediate Similarity	NPC298783
0.7597	Intermediate Similarity	NPC225385
0.7597	Intermediate Similarity	NPC476221
0.7516	Intermediate Similarity	NPC140092
0.7516	Intermediate Similarity	NPC188234
0.7516	Intermediate Similarity	NPC329986
0.7516	Intermediate Similarity	NPC125077
0.7516	Intermediate Similarity	NPC276838
0.7516	Intermediate Similarity	NPC232785
0.75	Intermediate Similarity	NPC171619
0.7434	Intermediate Similarity	NPC469750
0.7434	Intermediate Similarity	NPC250556
0.7386	Intermediate Similarity	NPC179412
0.7386	Intermediate Similarity	NPC471356
0.7386	Intermediate Similarity	NPC329784
0.7386	Intermediate Similarity	NPC240070
0.7372	Intermediate Similarity	NPC88668
0.7372	Intermediate Similarity	NPC116075
0.7372	Intermediate Similarity	NPC32793
0.7372	Intermediate Similarity	NPC146857
0.7372	Intermediate Similarity	NPC469749
0.7372	Intermediate Similarity	NPC247190
0.7342	Intermediate Similarity	NPC59288
0.7325	Intermediate Similarity	NPC329636
0.7303	Intermediate Similarity	NPC27363
0.729	Intermediate Similarity	NPC180079
0.729	Intermediate Similarity	NPC251866
0.729	Intermediate Similarity	NPC469752
0.729	Intermediate Similarity	NPC197707
0.729	Intermediate Similarity	NPC10823
0.729	Intermediate Similarity	NPC469755
0.729	Intermediate Similarity	NPC469751
0.729	Intermediate Similarity	NPC9499
0.729	Intermediate Similarity	NPC6108
0.729	Intermediate Similarity	NPC471352
0.729	Intermediate Similarity	NPC284406
0.729	Intermediate Similarity	NPC70542
0.729	Intermediate Similarity	NPC471361
0.729	Intermediate Similarity	NPC471358
0.729	Intermediate Similarity	NPC469754
0.729	Intermediate Similarity	NPC469753
0.729	Intermediate Similarity	NPC471360
0.729	Intermediate Similarity	NPC17896
0.729	Intermediate Similarity	NPC219085
0.729	Intermediate Similarity	NPC86159
0.729	Intermediate Similarity	NPC471359
0.729	Intermediate Similarity	NPC89514
0.7278	Intermediate Similarity	NPC194716
0.7233	Intermediate Similarity	NPC329675
0.7161	Intermediate Similarity	NPC469757
0.7161	Intermediate Similarity	NPC471357
0.7161	Intermediate Similarity	NPC117702
0.7161	Intermediate Similarity	NPC146456
0.7125	Intermediate Similarity	NPC297058
0.7039	Intermediate Similarity	NPC329905
0.7025	Intermediate Similarity	NPC201359
0.7006	Intermediate Similarity	NPC311534
0.6993	Remote Similarity	NPC474466
0.6993	Remote Similarity	NPC475136
0.6954	Remote Similarity	NPC196931
0.6928	Remote Similarity	NPC236973
0.6928	Remote Similarity	NPC55532
0.6928	Remote Similarity	NPC470897
0.6928	Remote Similarity	NPC292467
0.6928	Remote Similarity	NPC30483
0.6928	Remote Similarity	NPC469756
0.6928	Remote Similarity	NPC32177
0.6918	Remote Similarity	NPC478139
0.6914	Remote Similarity	NPC289700
0.6914	Remote Similarity	NPC62172
0.6908	Remote Similarity	NPC152615
0.6899	Remote Similarity	NPC478136
0.6883	Remote Similarity	NPC475556
0.6883	Remote Similarity	NPC475629
0.6883	Remote Similarity	NPC470312
0.6883	Remote Similarity	NPC72260
0.6875	Remote Similarity	NPC155529
0.6875	Remote Similarity	NPC471855
0.6863	Remote Similarity	NPC218093
0.6842	Remote Similarity	NPC99620
0.6842	Remote Similarity	NPC106228
0.6842	Remote Similarity	NPC138372
0.6842	Remote Similarity	NPC310341
0.6842	Remote Similarity	NPC5311
0.6842	Remote Similarity	NPC199428
0.6842	Remote Similarity	NPC193382
0.6839	Remote Similarity	NPC474908
0.6839	Remote Similarity	NPC475590
0.6839	Remote Similarity	NPC40749
0.6839	Remote Similarity	NPC475419
0.6839	Remote Similarity	NPC120390
0.6839	Remote Similarity	NPC314535
0.6839	Remote Similarity	NPC475219
0.6839	Remote Similarity	NPC173555
0.6839	Remote Similarity	NPC231518
0.6829	Remote Similarity	NPC79250
0.6829	Remote Similarity	NPC287885
0.6829	Remote Similarity	NPC75616
0.6829	Remote Similarity	NPC290746
0.6818	Remote Similarity	NPC291820
0.6818	Remote Similarity	NPC9674
0.6818	Remote Similarity	NPC19028
0.6818	Remote Similarity	NPC81222
0.6813	Remote Similarity	NPC173347
0.681	Remote Similarity	NPC127656
0.681	Remote Similarity	NPC477236
0.6802	Remote Similarity	NPC265699
0.6797	Remote Similarity	NPC158344
0.6797	Remote Similarity	NPC93883
0.6797	Remote Similarity	NPC309034
0.6797	Remote Similarity	NPC471355
0.6797	Remote Similarity	NPC142066
0.6797	Remote Similarity	NPC157376
0.6797	Remote Similarity	NPC34390
0.6797	Remote Similarity	NPC84987
0.6797	Remote Similarity	NPC471354
0.6797	Remote Similarity	NPC99728
0.6797	Remote Similarity	NPC27507
0.6797	Remote Similarity	NPC50305
0.6797	Remote Similarity	NPC473852
0.6797	Remote Similarity	NPC196429
0.6797	Remote Similarity	NPC471353
0.6797	Remote Similarity	NPC471351
0.6797	Remote Similarity	NPC244402
0.6797	Remote Similarity	NPC87250
0.6797	Remote Similarity	NPC474418
0.6797	Remote Similarity	NPC243196
0.6797	Remote Similarity	NPC77319
0.6795	Remote Similarity	NPC264336
0.6795	Remote Similarity	NPC193893
0.6795	Remote Similarity	NPC74259
0.6795	Remote Similarity	NPC28532
0.6795	Remote Similarity	NPC474423
0.6792	Remote Similarity	NPC477490
0.6792	Remote Similarity	NPC114306
0.6776	Remote Similarity	NPC471633
0.6776	Remote Similarity	NPC69576
0.6776	Remote Similarity	NPC31354
0.6776	Remote Similarity	NPC84949
0.6774	Remote Similarity	NPC107607
0.6763	Remote Similarity	NPC187497
0.6763	Remote Similarity	NPC475599
0.6763	Remote Similarity	NPC100612
0.6763	Remote Similarity	NPC174336
0.6763	Remote Similarity	NPC113620
0.6753	Remote Similarity	NPC83287
0.6752	Remote Similarity	NPC308262
0.6752	Remote Similarity	NPC208193
0.6752	Remote Similarity	NPC117445
0.675	Remote Similarity	NPC471407
0.6748	Remote Similarity	NPC158350
0.673	Remote Similarity	NPC317654
0.673	Remote Similarity	NPC96010
0.671	Remote Similarity	NPC29639
0.671	Remote Similarity	NPC477071
0.671	Remote Similarity	NPC122971
0.671	Remote Similarity	NPC304260
0.671	Remote Similarity	NPC5883
0.671	Remote Similarity	NPC44899
0.6708	Remote Similarity	NPC477493
0.6706	Remote Similarity	NPC61717
0.6706	Remote Similarity	NPC244380
0.6705	Remote Similarity	NPC475527
0.6688	Remote Similarity	NPC203862
0.6688	Remote Similarity	NPC39485
0.6688	Remote Similarity	NPC221196
0.6688	Remote Similarity	NPC290693
0.6687	Remote Similarity	NPC477234
0.6687	Remote Similarity	NPC248703
0.6687	Remote Similarity	NPC473888
0.6667	Remote Similarity	NPC478154
0.6667	Remote Similarity	NPC174367
0.6667	Remote Similarity	NPC15249
0.6667	Remote Similarity	NPC47113
0.6667	Remote Similarity	NPC477195
0.6667	Remote Similarity	NPC25455
0.6646	Remote Similarity	NPC41129
0.6646	Remote Similarity	NPC231529
0.6646	Remote Similarity	NPC476966
0.6626	Remote Similarity	NPC122819
0.6626	Remote Similarity	NPC478151
0.6625	Remote Similarity	NPC287423
0.6625	Remote Similarity	NPC470780
0.6623	Remote Similarity	NPC49492
0.6623	Remote Similarity	NPC266728
0.6607	Remote Similarity	NPC5153

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 NPC473040 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	854
0.2-0.3	3807
0.3-0.4	3200
0.4-0.5	890
0.5-0.6	219
0.6-0.7	40
0.7-0.8	6
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
0.8089	Intermediate Similarity	NPD7625	Phase 1
0.7434	Intermediate Similarity	NPD7507	Approved
0.729	Intermediate Similarity	NPD7319	Approved
0.6883	Remote Similarity	NPD8377	Approved
0.6883	Remote Similarity	NPD8294	Approved
0.6839	Remote Similarity	NPD8296	Approved
0.6839	Remote Similarity	NPD8335	Approved
0.6839	Remote Similarity	NPD8378	Approved
0.6839	Remote Similarity	NPD8033	Approved
0.6839	Remote Similarity	NPD8380	Approved
0.6839	Remote Similarity	NPD8379	Approved
0.6818	Remote Similarity	NPD7516	Approved
0.6753	Remote Similarity	NPD7327	Approved
0.6753	Remote Similarity	NPD7328	Approved
0.6626	Remote Similarity	NPD8449	Approved
0.6585	Remote Similarity	NPD8450	Suspended
0.646	Remote Similarity	NPD8451	Approved
0.6438	Remote Similarity	NPD6067	Discontinued
0.642	Remote Similarity	NPD8448	Approved
0.6402	Remote Similarity	NPD8391	Approved
0.6402	Remote Similarity	NPD8392	Approved
0.6402	Remote Similarity	NPD8390	Approved
0.6387	Remote Similarity	NPD8133	Approved
0.638	Remote Similarity	NPD7736	Approved
0.638	Remote Similarity	NPD8337	Approved
0.638	Remote Similarity	NPD8336	Approved
0.6335	Remote Similarity	NPD7122	Discontinued
0.6325	Remote Similarity	NPD6845	Suspended
0.6325	Remote Similarity	NPD8338	Approved
0.6312	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7503	Approved
0.6312	Remote Similarity	NPD6909	Approved
0.6312	Remote Similarity	NPD6908	Approved
0.6296	Remote Similarity	NPD8299	Approved
0.6296	Remote Similarity	NPD8340	Approved
0.6296	Remote Similarity	NPD8342	Approved
0.6296	Remote Similarity	NPD8341	Approved
0.6275	Remote Similarity	NPD6686	Approved
0.6235	Remote Similarity	NPD7642	Approved
0.6235	Remote Similarity	NPD8328	Phase 3
0.622	Remote Similarity	NPD8293	Discontinued
0.6205	Remote Similarity	NPD6914	Discontinued
0.6188	Remote Similarity	NPD7519	Approved
0.6188	Remote Similarity	NPD7518	Approved
0.6188	Remote Similarity	NPD7517	Approved
0.6173	Remote Similarity	NPD6370	Approved
0.6135	Remote Similarity	NPD7829	Approved
0.6135	Remote Similarity	NPD7830	Approved
0.6125	Remote Similarity	NPD7641	Discontinued
0.6121	Remote Similarity	NPD7078	Approved
0.6118	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6921	Approved
0.6104	Remote Similarity	NPD6412	Phase 2
0.6098	Remote Similarity	NPD7492	Approved
0.6071	Remote Similarity	NPD7260	Phase 2
0.6062	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6616	Approved
0.6059	Remote Similarity	NPD8415	Approved
0.6051	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD6054	Approved
0.6049	Remote Similarity	NPD6059	Approved
0.6012	Remote Similarity	NPD8517	Approved
0.6012	Remote Similarity	NPD8513	Phase 3
0.6012	Remote Similarity	NPD8515	Approved
0.6012	Remote Similarity	NPD8516	Approved
0.5976	Remote Similarity	NPD8080	Discontinued
0.5963	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6009	Approved
0.5963	Remote Similarity	NPD6317	Approved
0.596	Remote Similarity	NPD7638	Approved
0.5951	Remote Similarity	NPD7147	Phase 3
0.5951	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD7604	Phase 2
0.5935	Remote Similarity	NPD6008	Approved
0.5924	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD7640	Approved
0.5921	Remote Similarity	NPD7639	Approved
0.5917	Remote Similarity	NPD7751	Phase 1
0.5915	Remote Similarity	NPD6015	Approved
0.5915	Remote Similarity	NPD6016	Approved
0.5915	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD6882	Approved
0.5879	Remote Similarity	NPD5988	Approved
0.5875	Remote Similarity	NPD4632	Approved
0.5871	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6334	Approved
0.5862	Remote Similarity	NPD6333	Approved
0.5854	Remote Similarity	NPD6319	Approved
0.5833	Remote Similarity	NPD8074	Phase 3
0.5823	Remote Similarity	NPD6373	Approved
0.5823	Remote Similarity	NPD6372	Approved
0.5818	Remote Similarity	NPD8444	Approved
0.5813	Remote Similarity	NPD8297	Approved
0.5806	Remote Similarity	NPD6052	Approved
0.5799	Remote Similarity	NPD6033	Approved
0.5786	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD7115	Discovery
0.5759	Remote Similarity	NPD7320	Approved
0.575	Remote Similarity	NPD6650	Approved
0.575	Remote Similarity	NPD6649	Approved
0.5732	Remote Similarity	NPD6675	Approved
0.5732	Remote Similarity	NPD5739	Approved
0.5732	Remote Similarity	NPD7128	Approved
0.5732	Remote Similarity	NPD6402	Approved
0.5723	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6430	Approved
0.5714	Remote Similarity	NPD6429	Approved
0.5705	Remote Similarity	NPD4754	Approved
0.5687	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5687	Remote Similarity	NPD5135	Approved
0.566	Remote Similarity	NPD6899	Approved
0.566	Remote Similarity	NPD7999	Approved
0.566	Remote Similarity	NPD6881	Approved
0.5652	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD8462	Phase 1
0.5635	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD8268	Approved
0.5629	Remote Similarity	NPD8269	Approved
0.5629	Remote Similarity	NPD5983	Phase 2
0.5629	Remote Similarity	NPD8266	Approved
0.5629	Remote Similarity	NPD8267	Approved
0.5617	Remote Similarity	NPD6053	Discontinued
0.561	Remote Similarity	NPD6940	Discontinued

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