NPASS Compound

Structure

NPC475636 OpenBabel07101718242D 45 50 0 0 1 0 0 0 0 0999 V2000 -3.0745 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5590 -2.2276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 -1.0221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1731 -3.0238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.9359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0395 0.5392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1650 3.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2959 0.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0601 1.9180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4661 -1.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4579 1.5822 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6417 0.8749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1507 2.2739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2638 1.6001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6520 1.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9727 1.7828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9584 0.8253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1220 0.3590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9379 -0.1263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2153 0.2824 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8454 0.5570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5493 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4614 -0.6246 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4098 0.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3001 0.8501 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2554 -1.3673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4476 0.8928 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2534 0.9107 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7747 -0.5628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0013 3.6976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1853 -2.5529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4884 2.0307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8090 2.2491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7804 0.3342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1077 -0.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8486 -0.4222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7979 -1.5211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3524 1.1474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7010 -1.3198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6924 -2.2193 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 -3.6538 -0.9818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4637 0.3838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3144 1.8076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9863 1.5656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 1 0 0 0 0 4 40 1 0 0 0 0 5 11 1 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 27 1 0 0 0 0 7 30 1 0 0 0 0 8 41 1 0 0 0 0 9 1 1 1 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 31 2 0 0 0 0 10 42 1 0 0 0 0 11 27 1 6 0 0 0 12 15 1 0 0 0 0 12 43 1 0 0 0 0 13 7 1 1 0 0 0 13 16 1 0 0 0 0 13 44 1 0 0 0 0 14 28 1 6 0 0 0 14 45 1 0 0 0 0 15 32 2 0 0 0 0 16 17 1 0 0 0 0 16 33 1 6 0 0 0 17 18 1 0 0 0 0 17 34 1 1 0 0 0 18 25 1 0 0 0 0 18 35 1 6 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 19 36 1 6 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 20 42 1 1 0 0 0 21 27 1 6 0 0 0 21 28 1 0 0 0 0 22 28 1 6 0 0 0 22 29 1 0 0 0 0 23 29 1 1 0 0 0 23 37 1 0 0 0 0 24 38 2 0 0 0 0 24 45 1 0 0 0 0 25 43 1 1 0 0 0 25 44 1 0 0 0 0 26 39 2 0 0 0 0 26 40 1 0 0 0 0 27 3 1 6 0 0 0 28 8 1 6 0 0 0 29 26 1 6 0 0 0 29 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	642.22
Volume:	586.263
LogP:	-0.403
LogD:	-0.405
LogS:	-2.872
# Rotatable Bonds:	7
TPSA:	245.04
# H-Bond Aceptor:	16
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.127
Synthetic Accessibility Score:	6.887
Fsp3:	0.793
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:	-5.922
MDCK Permeability:	0.00032091751927509904
Pgp-inhibitor:	0.752
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.945
20% Bioavailability (F20%):	0.258
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	32.358421325683594%
Volume Distribution (VD):	0.382
Pgp-substrate:	42.416439056396484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.183
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	1.271
Half-life (T1/2):	0.583

ADMET: Toxicity

hERG Blockers:	0.201
Human Hepatotoxicity (H-HT):	0.62
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.3
Maximum Recommended Daily Dose:	0.248
Skin Sensitization:	0.14
Carcinogencity:	0.057
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.235

Download Data

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

Natural Product: NPC475636

Natural Product ID:	NPC475636
*Common Name:**	Yadanzioside F
IUPAC Name:	n.a.
Synonyms:	Yadanzioside F
Standard InCHIKey:	BYBDRFPMKPUWDZ-FDSGHLLVSA-N
Standard InCHI:	InChI=1S/C29H38O16/c1-9-11-5-14-28-8-41-29(26(39)40-4,22(28)20(24(38)45-14)42-10(2)31)23(37)19(36)21(28)27(11,3)6-12(15(9)32)43-25-18(35)17(34)16(33)13(7-30)44-25/h6,9,11,13-14,16-23,25,30,33-37H,5,7-8H2,1-4H3/t9-,11-,13+,14+,16+,17-,18+,19+,20+,21+,22+,23-,25+,27-,28+,29+/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC2=C[C@@]3(C)[C@H]([C@@H](C2=O)C)C[C@@H]2[C@@]45[C@@H]3[C@@H](O)[C@H](O)[C@@]([C@@H]5[C@H](C(=O)O2)OC(=O)C)(OC4)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509907
PubChem CID:	44584516
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14948	Brucea javanica	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
EC50	1
IC50	3
Others	2

Activity Type	# Activity
Cell Line	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	156000.0	nM	PMID[544853]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	109000.0	nM	PMID[544853]
NPT27	Others	Unspecified		Therapeutic index	=	1.4	n.a.	PMID[544853]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	5.0	ug.mL-1	PMID[544854]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	31.1	%	PMID[544855]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	2.33	ug.mL-1	PMID[544856]

☑ 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 NPC475636 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	311
0.1-0.2	1955
0.2-0.3	5597
0.3-0.4	8592
0.4-0.5	11241
0.5-0.6	7841
0.6-0.7	4546
0.7-0.8	2026
0.8-0.85	436
0.85-0.9	126
0.9-0.95	18
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC295220
0.9915	High Similarity	NPC54614
0.9915	High Similarity	NPC309096
0.9661	High Similarity	NPC87662
0.9658	High Similarity	NPC227397
0.9487	High Similarity	NPC275675
0.9435	High Similarity	NPC141215
0.9435	High Similarity	NPC471089
0.9435	High Similarity	NPC190065
0.936	High Similarity	NPC295885
0.936	High Similarity	NPC596
0.936	High Similarity	NPC140045
0.9355	High Similarity	NPC262813
0.9316	High Similarity	NPC279143
0.9316	High Similarity	NPC473920
0.9316	High Similarity	NPC127530
0.928	High Similarity	NPC251998
0.9016	High Similarity	NPC285091
0.8992	High Similarity	NPC470777
0.8898	High Similarity	NPC16081
0.8898	High Similarity	NPC173686
0.8852	High Similarity	NPC471964
0.8852	High Similarity	NPC202666
0.8852	High Similarity	NPC262199
0.8852	High Similarity	NPC14617
0.8852	High Similarity	NPC471961
0.8814	High Similarity	NPC323821
0.8814	High Similarity	NPC45218
0.8814	High Similarity	NPC268238
0.8814	High Similarity	NPC143268
0.881	High Similarity	NPC478154
0.878	High Similarity	NPC247315
0.878	High Similarity	NPC30188
0.878	High Similarity	NPC471962
0.878	High Similarity	NPC471963
0.878	High Similarity	NPC177820
0.877	High Similarity	NPC40775
0.877	High Similarity	NPC471965
0.877	High Similarity	NPC235438
0.877	High Similarity	NPC249848
0.877	High Similarity	NPC107966
0.875	High Similarity	NPC176005
0.875	High Similarity	NPC17772
0.875	High Similarity	NPC297179
0.874	High Similarity	NPC478151
0.873	High Similarity	NPC25998
0.873	High Similarity	NPC478155
0.8729	High Similarity	NPC198539
0.8699	High Similarity	NPC105926
0.8699	High Similarity	NPC91693
0.8699	High Similarity	NPC18945
0.8699	High Similarity	NPC478066
0.8699	High Similarity	NPC235405
0.8699	High Similarity	NPC281148
0.8699	High Similarity	NPC30735
0.8699	High Similarity	NPC265557
0.8678	High Similarity	NPC469488
0.8667	High Similarity	NPC309433
0.8661	High Similarity	NPC478153
0.8661	High Similarity	NPC478150
0.8661	High Similarity	NPC478152
0.8661	High Similarity	NPC100390
0.8661	High Similarity	NPC254614
0.8651	High Similarity	NPC477196
0.864	High Similarity	NPC470780
0.8629	High Similarity	NPC6615
0.8629	High Similarity	NPC476729
0.8629	High Similarity	NPC469841
0.8629	High Similarity	NPC7850
0.8629	High Similarity	NPC24651
0.8629	High Similarity	NPC470477
0.8629	High Similarity	NPC469842
0.8618	High Similarity	NPC312833
0.8618	High Similarity	NPC162574
0.8618	High Similarity	NPC213952
0.8595	High Similarity	NPC188667
0.8595	High Similarity	NPC204552
0.8583	High Similarity	NPC264566
0.8583	High Similarity	NPC301639
0.8583	High Similarity	NPC235539
0.8583	High Similarity	NPC173435
0.8583	High Similarity	NPC134869
0.8583	High Similarity	NPC475167
0.8583	High Similarity	NPC478065
0.8583	High Similarity	NPC478064
0.8583	High Similarity	NPC476074
0.8583	High Similarity	NPC262796
0.8583	High Similarity	NPC477197
0.8583	High Similarity	NPC328374
0.8583	High Similarity	NPC134914
0.8583	High Similarity	NPC152199
0.8583	High Similarity	NPC172374
0.8583	High Similarity	NPC329993
0.8583	High Similarity	NPC96312
0.8583	High Similarity	NPC251236
0.8583	High Similarity	NPC45346
0.8583	High Similarity	NPC40632
0.8583	High Similarity	NPC475377
0.8571	High Similarity	NPC477192
0.8571	High Similarity	NPC477193
0.8571	High Similarity	NPC477194
0.8571	High Similarity	NPC477191
0.856	High Similarity	NPC470218
0.856	High Similarity	NPC181066
0.856	High Similarity	NPC469947
0.8548	High Similarity	NPC257211
0.8547	High Similarity	NPC27814
0.8537	High Similarity	NPC114484
0.8537	High Similarity	NPC301449
0.8537	High Similarity	NPC104372
0.8537	High Similarity	NPC64715
0.8537	High Similarity	NPC22956
0.8537	High Similarity	NPC62725
0.8537	High Similarity	NPC131841
0.8537	High Similarity	NPC222580
0.8537	High Similarity	NPC159309
0.8537	High Similarity	NPC102822
0.8537	High Similarity	NPC477046
0.8537	High Similarity	NPC11242
0.8537	High Similarity	NPC171544
0.8537	High Similarity	NPC278163
0.8537	High Similarity	NPC75417
0.8537	High Similarity	NPC31838
0.8537	High Similarity	NPC241310
0.8537	High Similarity	NPC169727
0.8537	High Similarity	NPC86222
0.8537	High Similarity	NPC223301
0.8537	High Similarity	NPC412
0.8537	High Similarity	NPC194310
0.8537	High Similarity	NPC258789
0.8537	High Similarity	NPC297263
0.8537	High Similarity	NPC258815
0.8537	High Similarity	NPC187950
0.8537	High Similarity	NPC47567
0.8525	High Similarity	NPC180550
0.8525	High Similarity	NPC6377
0.8525	High Similarity	NPC309780
0.8525	High Similarity	NPC114441
0.8525	High Similarity	NPC35405
0.8525	High Similarity	NPC208381
0.8525	High Similarity	NPC469945
0.8525	High Similarity	NPC11551
0.8525	High Similarity	NPC157868
0.8525	High Similarity	NPC473884
0.8525	High Similarity	NPC475171
0.8525	High Similarity	NPC214484
0.8525	High Similarity	NPC39211
0.8525	High Similarity	NPC472949
0.8516	High Similarity	NPC476776
0.8516	High Similarity	NPC477195
0.8512	High Similarity	NPC97908
0.8512	High Similarity	NPC122033
0.8512	High Similarity	NPC470854
0.8512	High Similarity	NPC287343
0.8512	High Similarity	NPC474654
0.8504	High Similarity	NPC252289
0.8504	High Similarity	NPC244296
0.8504	High Similarity	NPC9470
0.8504	High Similarity	NPC97918
0.8504	High Similarity	NPC280029
0.8504	High Similarity	NPC141600
0.8504	High Similarity	NPC470518
0.8504	High Similarity	NPC1314
0.8504	High Similarity	NPC82380
0.8504	High Similarity	NPC477079
0.8504	High Similarity	NPC252657
0.8504	High Similarity	NPC273878
0.8504	High Similarity	NPC88311
0.8504	High Similarity	NPC107536
0.8504	High Similarity	NPC115656
0.8504	High Similarity	NPC470913
0.8504	High Similarity	NPC472267
0.8504	High Similarity	NPC11577
0.8504	High Similarity	NPC477077
0.8504	High Similarity	NPC305793
0.8504	High Similarity	NPC269484
0.8504	High Similarity	NPC477076
0.85	High Similarity	NPC473798
0.85	High Similarity	NPC474906
0.85	High Similarity	NPC18547
0.848	Intermediate Similarity	NPC470922
0.848	Intermediate Similarity	NPC23275
0.848	Intermediate Similarity	NPC33068
0.8468	Intermediate Similarity	NPC21691
0.8468	Intermediate Similarity	NPC10607
0.8468	Intermediate Similarity	NPC187290
0.8468	Intermediate Similarity	NPC475591
0.8468	Intermediate Similarity	NPC4749
0.8468	Intermediate Similarity	NPC236870
0.8468	Intermediate Similarity	NPC80986
0.8455	Intermediate Similarity	NPC236657
0.8455	Intermediate Similarity	NPC118440
0.8455	Intermediate Similarity	NPC112038
0.8455	Intermediate Similarity	NPC473645
0.8443	Intermediate Similarity	NPC286347
0.8438	Intermediate Similarity	NPC271610
0.8438	Intermediate Similarity	NPC476780
0.8438	Intermediate Similarity	NPC476775
0.8438	Intermediate Similarity	NPC476774
0.8425	Intermediate Similarity	NPC477075

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 NPC475636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	2282
0.2-0.3	3942
0.3-0.4	1643
0.4-0.5	529
0.5-0.6	285
0.6-0.7	124
0.7-0.8	64
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8852	High Similarity	NPD8328	Phase 3
0.8361	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD7736	Approved
0.8031	Intermediate Similarity	NPD6370	Approved
0.7934	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD8293	Discontinued
0.7907	Intermediate Similarity	NPD7492	Approved
0.7874	Intermediate Similarity	NPD6054	Approved
0.7846	Intermediate Similarity	NPD6616	Approved
0.7786	Intermediate Similarity	NPD7078	Approved
0.7734	Intermediate Similarity	NPD6059	Approved
0.7734	Intermediate Similarity	NPD6319	Approved
0.7705	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6015	Approved
0.7674	Intermediate Similarity	NPD6016	Approved
0.7669	Intermediate Similarity	NPD7319	Approved
0.7615	Intermediate Similarity	NPD5988	Approved
0.76	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.748	Intermediate Similarity	NPD6412	Phase 2
0.746	Intermediate Similarity	NPD8297	Approved
0.7444	Intermediate Similarity	NPD7507	Approved
0.7419	Intermediate Similarity	NPD6686	Approved
0.7405	Intermediate Similarity	NPD8517	Approved
0.7405	Intermediate Similarity	NPD8513	Phase 3
0.7405	Intermediate Similarity	NPD8516	Approved
0.7405	Intermediate Similarity	NPD8515	Approved
0.7381	Intermediate Similarity	NPD6649	Approved
0.7381	Intermediate Similarity	NPD6650	Approved
0.736	Intermediate Similarity	NPD6373	Approved
0.736	Intermediate Similarity	NPD6372	Approved
0.728	Intermediate Similarity	NPD6899	Approved
0.728	Intermediate Similarity	NPD6881	Approved
0.7273	Intermediate Similarity	NPD7503	Approved
0.7266	Intermediate Similarity	NPD8133	Approved
0.7266	Intermediate Similarity	NPD4632	Approved
0.7258	Intermediate Similarity	NPD7128	Approved
0.7258	Intermediate Similarity	NPD6402	Approved
0.7258	Intermediate Similarity	NPD5739	Approved
0.7258	Intermediate Similarity	NPD6675	Approved
0.7206	Intermediate Similarity	NPD6033	Approved
0.72	Intermediate Similarity	NPD5697	Approved
0.7165	Intermediate Similarity	NPD7102	Approved
0.7165	Intermediate Similarity	NPD7290	Approved
0.7165	Intermediate Similarity	NPD6883	Approved
0.7143	Intermediate Similarity	NPD8335	Approved
0.7143	Intermediate Similarity	NPD8296	Approved
0.7143	Intermediate Similarity	NPD8378	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD6921	Approved
0.7143	Intermediate Similarity	NPD8379	Approved
0.7143	Intermediate Similarity	NPD8380	Approved
0.7121	Intermediate Similarity	NPD7516	Approved
0.7109	Intermediate Similarity	NPD6617	Approved
0.7109	Intermediate Similarity	NPD6869	Approved
0.7109	Intermediate Similarity	NPD6847	Approved
0.7109	Intermediate Similarity	NPD8130	Phase 1
0.7087	Intermediate Similarity	NPD6014	Approved
0.7087	Intermediate Similarity	NPD6012	Approved
0.7087	Intermediate Similarity	NPD6013	Approved
0.7068	Intermediate Similarity	NPD8294	Approved
0.7068	Intermediate Similarity	NPD8377	Approved
0.7063	Intermediate Similarity	NPD5701	Approved
0.7045	Intermediate Similarity	NPD7328	Approved
0.7045	Intermediate Similarity	NPD7327	Approved
0.7037	Intermediate Similarity	NPD7604	Phase 2
0.7031	Intermediate Similarity	NPD4634	Approved
0.7015	Intermediate Similarity	NPD5983	Phase 2
0.7015	Intermediate Similarity	NPD8033	Approved
0.7008	Intermediate Similarity	NPD6011	Approved
0.697	Remote Similarity	NPD7115	Discovery
0.6953	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6336	Discontinued
0.6905	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8080	Discontinued
0.6829	Remote Similarity	NPD7902	Approved
0.6767	Remote Similarity	NPD6274	Approved
0.6741	Remote Similarity	NPD7100	Approved
0.6741	Remote Similarity	NPD7101	Approved
0.6721	Remote Similarity	NPD7748	Approved
0.672	Remote Similarity	NPD4696	Approved
0.672	Remote Similarity	NPD5286	Approved
0.672	Remote Similarity	NPD5285	Approved
0.6719	Remote Similarity	NPD6008	Approved
0.6718	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6084	Phase 2
0.6694	Remote Similarity	NPD4755	Approved
0.6694	Remote Similarity	NPD6083	Phase 2
0.6694	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD8074	Phase 3
0.6642	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.664	Remote Similarity	NPD4225	Approved
0.664	Remote Similarity	NPD5696	Approved
0.662	Remote Similarity	NPD5956	Approved
0.6614	Remote Similarity	NPD4633	Approved
0.6614	Remote Similarity	NPD5225	Approved
0.6614	Remote Similarity	NPD5211	Phase 2
0.6614	Remote Similarity	NPD5224	Approved
0.6614	Remote Similarity	NPD5226	Approved
0.6593	Remote Similarity	NPD6317	Approved
0.6587	Remote Similarity	NPD4700	Approved
0.6585	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5282	Discontinued
0.6585	Remote Similarity	NPD7900	Approved
0.6562	Remote Similarity	NPD5175	Approved
0.6562	Remote Similarity	NPD5174	Approved
0.6544	Remote Similarity	NPD6313	Approved
0.6544	Remote Similarity	NPD6314	Approved
0.6535	Remote Similarity	NPD5223	Approved
0.6522	Remote Similarity	NPD6909	Approved
0.6522	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6908	Approved
0.6519	Remote Similarity	NPD6868	Approved
0.6512	Remote Similarity	NPD5141	Approved
0.65	Remote Similarity	NPD3573	Approved
0.6489	Remote Similarity	NPD4730	Approved
0.6489	Remote Similarity	NPD4729	Approved
0.648	Remote Similarity	NPD4697	Phase 3
0.648	Remote Similarity	NPD5222	Approved
0.648	Remote Similarity	NPD5221	Approved
0.648	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4767	Approved
0.6462	Remote Similarity	NPD4768	Approved
0.6458	Remote Similarity	NPD7260	Phase 2
0.6429	Remote Similarity	NPD5173	Approved
0.6423	Remote Similarity	NPD6079	Approved
0.6414	Remote Similarity	NPD6845	Suspended
0.6414	Remote Similarity	NPD8338	Approved
0.64	Remote Similarity	NPD5695	Phase 3
0.6393	Remote Similarity	NPD5328	Approved
0.6391	Remote Similarity	NPD5248	Approved
0.6391	Remote Similarity	NPD5251	Approved
0.6391	Remote Similarity	NPD5247	Approved
0.6391	Remote Similarity	NPD5249	Phase 3
0.6391	Remote Similarity	NPD5250	Approved
0.6378	Remote Similarity	NPD7638	Approved
0.6371	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD8337	Approved
0.6364	Remote Similarity	NPD5128	Approved
0.6364	Remote Similarity	NPD8336	Approved
0.635	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7640	Approved
0.6328	Remote Similarity	NPD7639	Approved
0.6311	Remote Similarity	NPD5737	Approved
0.6311	Remote Similarity	NPD6672	Approved
0.631	Remote Similarity	NPD7799	Discontinued
0.6308	Remote Similarity	NPD4754	Approved
0.629	Remote Similarity	NPD6411	Approved
0.6288	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD3618	Phase 1
0.6279	Remote Similarity	NPD1700	Approved
0.627	Remote Similarity	NPD4629	Approved
0.627	Remote Similarity	NPD5210	Approved
0.626	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8407	Phase 2
0.6222	Remote Similarity	NPD5215	Approved
0.6222	Remote Similarity	NPD5216	Approved
0.6222	Remote Similarity	NPD5217	Approved
0.62	Remote Similarity	NPD6334	Approved
0.62	Remote Similarity	NPD6333	Approved
0.6197	Remote Similarity	NPD7642	Approved
0.6176	Remote Similarity	NPD6053	Discontinued
0.6163	Remote Similarity	NPD8368	Discontinued
0.6148	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6371	Approved
0.6148	Remote Similarity	NPD5135	Approved
0.6148	Remote Similarity	NPD5169	Approved
0.6142	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6673	Approved
0.6129	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6904	Approved
0.6129	Remote Similarity	NPD6080	Approved
0.6129	Remote Similarity	NPD4753	Phase 2
0.6129	Remote Similarity	NPD6101	Approved
0.6111	Remote Similarity	NPD4202	Approved
0.6111	Remote Similarity	NPD8171	Discontinued
0.6103	Remote Similarity	NPD5127	Approved
0.6084	Remote Similarity	NPD7829	Approved
0.6084	Remote Similarity	NPD7830	Approved
0.608	Remote Similarity	NPD8434	Phase 2
0.6071	Remote Similarity	NPD7641	Discontinued
0.6069	Remote Similarity	NPD8448	Approved
0.6067	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD6914	Discontinued
0.6048	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8341	Approved
0.6042	Remote Similarity	NPD8340	Approved
0.6042	Remote Similarity	NPD8299	Approved
0.6042	Remote Similarity	NPD8342	Approved
0.6033	Remote Similarity	NPD3669	Approved
0.6033	Remote Similarity	NPD3670	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