NPASS Compound

Structure

CID293753 OpenBabel06191716102D 36 39 0 0 1 0 0 0 0 0999 V2000 -1.8191 2.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2808 4.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 -2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2526 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 4.1227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3583 3.2793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8196 4.1224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2210 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6879 0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6894 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 2.4357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3068 4.9658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 1.4617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8448 -1.4622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6885 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5336 -1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2212 -1.4613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8201 5.8094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3776 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5333 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0211 -1.9625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5544 1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0875 -1.9609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3945 -0.7078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3073 6.6528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 5.8097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 28 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 29 1 0 0 0 0 16 1 1 6 0 0 0 16 18 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 6 0 0 0 19 25 1 0 0 0 0 19 31 1 6 0 0 0 20 24 1 0 0 0 0 20 32 2 0 0 0 0 21 27 1 0 0 0 0 21 28 1 6 0 0 0 22 27 1 0 0 0 0 22 33 1 6 0 0 0 23 30 1 0 0 0 0 23 34 2 0 0 0 0 24 25 2 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 35 2 0 0 0 0 26 36 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	532.769
LogP:	4.128
LogD:	4.004
LogS:	-3.991
# Rotatable Bonds:	5
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	5.078
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
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:	-5.328
MDCK Permeability:	2.2282445570454e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	75.35200500488281%
Volume Distribution (VD):	0.476
Pgp-substrate:	15.101629257202148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.424
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.165
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	11.08
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.915
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.143
Carcinogencity:	0.041
Eye Corrosion:	0.091
Eye Irritation:	0.025
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC293753

Natural Product ID:	NPC293753
*Common Name:**	Ganoderic Acid Beta
IUPAC Name:	(E,6R)-6-[(3S,5R,7S,10S,13R,14R,17R)-3,7-dihydroxy-4,4,10,13,14-pentamethyl-11,15-dioxo-2,3,5,6,7,12,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Synonyms:	Ganoderic Acid Beta
Standard InCHIKey:	NJZMSAAKSXZIEC-UQOIKQOMSA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-16(9-8-10-17(2)26(35)36)18-13-23(34)30(7)25-19(31)14-21-27(3,4)22(33)11-12-28(21,5)24(25)20(32)15-29(18,30)6/h10,16,18-19,21-22,31,33H,8-9,11-15H2,1-7H3,(H,35,36)/b17-10+/t16-,18-,19+,21+,22+,28+,29-,30+/m1/s1
SMILES:	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1CC(=O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1C[C@@H]3O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474065
PubChem CID:	10097521
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO32479	gleophyllum lucidum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[Title]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC50	=	20000.0	nM	PMID[502193]

☑ 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 NPC293753 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	181
0.1-0.2	1115
0.2-0.3	4287
0.3-0.4	9617
0.4-0.5	12201
0.5-0.6	6561
0.6-0.7	6037
0.7-0.8	2270
0.8-0.85	304
0.85-0.9	100
0.9-0.95	21
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC234892
0.9574	High Similarity	NPC122294
0.9474	High Similarity	NPC16021
0.9468	High Similarity	NPC472941
0.9468	High Similarity	NPC456
0.9375	High Similarity	NPC307954
0.9375	High Similarity	NPC144660
0.9375	High Similarity	NPC299971
0.9375	High Similarity	NPC287833
0.9368	High Similarity	NPC320306
0.9216	High Similarity	NPC472928
0.9184	High Similarity	NPC281702
0.9175	High Similarity	NPC327431
0.9175	High Similarity	NPC51370
0.9158	High Similarity	NPC297199
0.9109	High Similarity	NPC295244
0.9091	High Similarity	NPC251017
0.9082	High Similarity	NPC472924
0.9062	High Similarity	NPC7124
0.9043	High Similarity	NPC233116
0.901	High Similarity	NPC472925
0.8969	High Similarity	NPC108078
0.8958	High Similarity	NPC271195
0.8958	High Similarity	NPC37646
0.8911	High Similarity	NPC51452
0.8878	High Similarity	NPC103051
0.8866	High Similarity	NPC3772
0.8866	High Similarity	NPC243525
0.8866	High Similarity	NPC40765
0.8854	High Similarity	NPC469406
0.883	High Similarity	NPC214387
0.8824	High Similarity	NPC473037
0.8788	High Similarity	NPC154072
0.8788	High Similarity	NPC476274
0.8785	High Similarity	NPC472927
0.8776	High Similarity	NPC121339
0.8776	High Similarity	NPC253826
0.8776	High Similarity	NPC106557
0.8763	High Similarity	NPC318282
0.8763	High Similarity	NPC173875
0.8763	High Similarity	NPC255809
0.8763	High Similarity	NPC469995
0.8763	High Similarity	NPC174948
0.875	High Similarity	NPC69454
0.875	High Similarity	NPC214697
0.8737	High Similarity	NPC477149
0.8737	High Similarity	NPC469400
0.8737	High Similarity	NPC477147
0.8725	High Similarity	NPC323834
0.8713	High Similarity	NPC55872
0.87	High Similarity	NPC476240
0.87	High Similarity	NPC224720
0.87	High Similarity	NPC476223
0.8687	High Similarity	NPC166745
0.8687	High Similarity	NPC197386
0.8687	High Similarity	NPC48647
0.8687	High Similarity	NPC235464
0.8687	High Similarity	NPC114274
0.8687	High Similarity	NPC478056
0.8673	High Similarity	NPC250757
0.8673	High Similarity	NPC249954
0.8673	High Similarity	NPC301534
0.8673	High Similarity	NPC328371
0.8673	High Similarity	NPC117133
0.866	High Similarity	NPC279410
0.866	High Similarity	NPC166906
0.866	High Similarity	NPC119562
0.8654	High Similarity	NPC286174
0.8654	High Similarity	NPC77947
0.8646	High Similarity	NPC297265
0.8646	High Similarity	NPC63748
0.8646	High Similarity	NPC473998
0.8646	High Similarity	NPC212948
0.8632	High Similarity	NPC472240
0.8632	High Similarity	NPC262858
0.8632	High Similarity	NPC473999
0.8632	High Similarity	NPC309603
0.8627	High Similarity	NPC28656
0.8624	High Similarity	NPC472933
0.8617	High Similarity	NPC187376
0.8617	High Similarity	NPC159046
0.8617	High Similarity	NPC233836
0.8614	High Similarity	NPC195290
0.8614	High Similarity	NPC136289
0.8614	High Similarity	NPC204450
0.86	High Similarity	NPC470074
0.8586	High Similarity	NPC43747
0.8571	High Similarity	NPC259286
0.8571	High Similarity	NPC317586
0.8571	High Similarity	NPC129689
0.8571	High Similarity	NPC476174
0.8571	High Similarity	NPC272898
0.8571	High Similarity	NPC470016
0.8571	High Similarity	NPC473036
0.8557	High Similarity	NPC472930
0.8542	High Similarity	NPC48010
0.8542	High Similarity	NPC191684
0.8529	High Similarity	NPC478057
0.8529	High Similarity	NPC249187
0.8529	High Similarity	NPC236390
0.8529	High Similarity	NPC247957
0.8526	High Similarity	NPC242864
0.8526	High Similarity	NPC471722
0.8515	High Similarity	NPC302537
0.8515	High Similarity	NPC163372
0.8515	High Similarity	NPC81530
0.8511	High Similarity	NPC55309
0.8511	High Similarity	NPC72133
0.8511	High Similarity	NPC28252
0.8505	High Similarity	NPC472929
0.8505	High Similarity	NPC472926
0.85	High Similarity	NPC186810
0.85	High Similarity	NPC471717
0.8491	Intermediate Similarity	NPC115303
0.8485	Intermediate Similarity	NPC305483
0.8485	Intermediate Similarity	NPC96859
0.8485	Intermediate Similarity	NPC328162
0.8485	Intermediate Similarity	NPC173272
0.8469	Intermediate Similarity	NPC196485
0.8469	Intermediate Similarity	NPC8993
0.8469	Intermediate Similarity	NPC184870
0.8469	Intermediate Similarity	NPC245972
0.8469	Intermediate Similarity	NPC111015
0.8454	Intermediate Similarity	NPC107690
0.8454	Intermediate Similarity	NPC212301
0.8454	Intermediate Similarity	NPC475806
0.8454	Intermediate Similarity	NPC86266
0.8454	Intermediate Similarity	NPC23434
0.8454	Intermediate Similarity	NPC110657
0.8447	Intermediate Similarity	NPC72255
0.8447	Intermediate Similarity	NPC209502
0.8447	Intermediate Similarity	NPC204833
0.844	Intermediate Similarity	NPC472934
0.8438	Intermediate Similarity	NPC86319
0.8438	Intermediate Similarity	NPC475921
0.8438	Intermediate Similarity	NPC77168
0.8438	Intermediate Similarity	NPC84271
0.8438	Intermediate Similarity	NPC102414
0.8438	Intermediate Similarity	NPC474704
0.8438	Intermediate Similarity	NPC146554
0.8438	Intermediate Similarity	NPC275740
0.8431	Intermediate Similarity	NPC473424
0.8431	Intermediate Similarity	NPC119601
0.8431	Intermediate Similarity	NPC308726
0.8421	Intermediate Similarity	NPC474684
0.8421	Intermediate Similarity	NPC142361
0.8416	Intermediate Similarity	NPC88198
0.8416	Intermediate Similarity	NPC157787
0.8416	Intermediate Similarity	NPC316964
0.8404	Intermediate Similarity	NPC474083
0.8404	Intermediate Similarity	NPC8571
0.84	Intermediate Similarity	NPC141401
0.84	Intermediate Similarity	NPC99726
0.8396	Intermediate Similarity	NPC286880
0.8384	Intermediate Similarity	NPC162001
0.8384	Intermediate Similarity	NPC45324
0.8384	Intermediate Similarity	NPC222845
0.8384	Intermediate Similarity	NPC48330
0.8381	Intermediate Similarity	NPC65941
0.8367	Intermediate Similarity	NPC170220
0.8367	Intermediate Similarity	NPC141497
0.8367	Intermediate Similarity	NPC38232
0.8367	Intermediate Similarity	NPC470376
0.8367	Intermediate Similarity	NPC243866
0.8367	Intermediate Similarity	NPC470375
0.8367	Intermediate Similarity	NPC107674
0.8367	Intermediate Similarity	NPC476304
0.8367	Intermediate Similarity	NPC470254
0.8365	Intermediate Similarity	NPC152695
0.8365	Intermediate Similarity	NPC476027
0.8365	Intermediate Similarity	NPC85829
0.8365	Intermediate Similarity	NPC149047
0.8365	Intermediate Similarity	NPC171137
0.8365	Intermediate Similarity	NPC202167
0.8365	Intermediate Similarity	NPC97202
0.8365	Intermediate Similarity	NPC214264
0.8365	Intermediate Similarity	NPC48733
0.8365	Intermediate Similarity	NPC302607
0.8365	Intermediate Similarity	NPC319077
0.8365	Intermediate Similarity	NPC150531
0.8365	Intermediate Similarity	NPC260268
0.8365	Intermediate Similarity	NPC50692
0.8365	Intermediate Similarity	NPC296945
0.8365	Intermediate Similarity	NPC257353
0.8365	Intermediate Similarity	NPC49958
0.8351	Intermediate Similarity	NPC111585
0.8351	Intermediate Similarity	NPC175628
0.8351	Intermediate Similarity	NPC148414
0.835	Intermediate Similarity	NPC95899
0.8333	Intermediate Similarity	NPC250109
0.8333	Intermediate Similarity	NPC282524
0.8333	Intermediate Similarity	NPC104560
0.8333	Intermediate Similarity	NPC143767
0.8333	Intermediate Similarity	NPC48107
0.8333	Intermediate Similarity	NPC471724
0.8333	Intermediate Similarity	NPC99411
0.8333	Intermediate Similarity	NPC131470
0.8333	Intermediate Similarity	NPC115862
0.8333	Intermediate Similarity	NPC962
0.8317	Intermediate Similarity	NPC108368

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 NPC293753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1479
0.2-0.3	3820
0.3-0.4	2456
0.4-0.5	750
0.5-0.6	183
0.6-0.7	189
0.7-0.8	121
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD3618	Phase 1
0.8265	Intermediate Similarity	NPD6079	Approved
0.8247	Intermediate Similarity	NPD5328	Approved
0.8235	Intermediate Similarity	NPD7639	Approved
0.8235	Intermediate Similarity	NPD7640	Approved
0.8137	Intermediate Similarity	NPD7638	Approved
0.8081	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7946	Intermediate Similarity	NPD7115	Discovery
0.7941	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD5221	Approved
0.7941	Intermediate Similarity	NPD4697	Phase 3
0.7941	Intermediate Similarity	NPD5222	Approved
0.7917	Intermediate Similarity	NPD4786	Approved
0.7905	Intermediate Similarity	NPD5211	Phase 2
0.787	Intermediate Similarity	NPD6881	Approved
0.787	Intermediate Similarity	NPD6899	Approved
0.7864	Intermediate Similarity	NPD5173	Approved
0.785	Intermediate Similarity	NPD5739	Approved
0.785	Intermediate Similarity	NPD6675	Approved
0.785	Intermediate Similarity	NPD7128	Approved
0.785	Intermediate Similarity	NPD6402	Approved
0.7843	Intermediate Similarity	NPD4629	Approved
0.7843	Intermediate Similarity	NPD5210	Approved
0.7822	Intermediate Similarity	NPD4202	Approved
0.7818	Intermediate Similarity	NPD6649	Approved
0.7818	Intermediate Similarity	NPD6650	Approved
0.7798	Intermediate Similarity	NPD6373	Approved
0.7798	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD5696	Approved
0.7778	Intermediate Similarity	NPD5697	Approved
0.7757	Intermediate Similarity	NPD5141	Approved
0.7755	Intermediate Similarity	NPD5279	Phase 3
0.7745	Intermediate Similarity	NPD7748	Approved
0.7732	Intermediate Similarity	NPD3666	Approved
0.7732	Intermediate Similarity	NPD3665	Phase 1
0.7732	Intermediate Similarity	NPD3133	Approved
0.7727	Intermediate Similarity	NPD6883	Approved
0.7727	Intermediate Similarity	NPD7290	Approved
0.7727	Intermediate Similarity	NPD7102	Approved
0.7723	Intermediate Similarity	NPD5284	Approved
0.7723	Intermediate Similarity	NPD5281	Approved
0.7714	Intermediate Similarity	NPD5286	Approved
0.7714	Intermediate Similarity	NPD4696	Approved
0.7714	Intermediate Similarity	NPD5285	Approved
0.7708	Intermediate Similarity	NPD3667	Approved
0.7706	Intermediate Similarity	NPD6011	Approved
0.7706	Intermediate Similarity	NPD7320	Approved
0.7692	Intermediate Similarity	NPD6083	Phase 2
0.7692	Intermediate Similarity	NPD6084	Phase 2
0.7692	Intermediate Similarity	NPD4755	Approved
0.7692	Intermediate Similarity	NPD7902	Approved
0.7679	Intermediate Similarity	NPD4632	Approved
0.767	Intermediate Similarity	NPD5695	Phase 3
0.7658	Intermediate Similarity	NPD8130	Phase 1
0.7658	Intermediate Similarity	NPD6869	Approved
0.7658	Intermediate Similarity	NPD6847	Approved
0.7658	Intermediate Similarity	NPD6617	Approved
0.7653	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5223	Approved
0.7636	Intermediate Similarity	NPD6012	Approved
0.7636	Intermediate Similarity	NPD6014	Approved
0.7636	Intermediate Similarity	NPD6013	Approved
0.7615	Intermediate Similarity	NPD5701	Approved
0.76	Intermediate Similarity	NPD6672	Approved
0.76	Intermediate Similarity	NPD5737	Approved
0.7589	Intermediate Similarity	NPD8297	Approved
0.7589	Intermediate Similarity	NPD6882	Approved
0.7576	Intermediate Similarity	NPD7146	Approved
0.7576	Intermediate Similarity	NPD7334	Approved
0.7576	Intermediate Similarity	NPD5330	Approved
0.7576	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6409	Approved
0.7576	Intermediate Similarity	NPD7521	Approved
0.7576	Intermediate Similarity	NPD6684	Approved
0.757	Intermediate Similarity	NPD4633	Approved
0.757	Intermediate Similarity	NPD7632	Discontinued
0.757	Intermediate Similarity	NPD5224	Approved
0.757	Intermediate Similarity	NPD5226	Approved
0.757	Intermediate Similarity	NPD5225	Approved
0.7547	Intermediate Similarity	NPD4700	Approved
0.7525	Intermediate Similarity	NPD4753	Phase 2
0.7523	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5174	Approved
0.7478	Intermediate Similarity	NPD6009	Approved
0.7474	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6903	Approved
0.7411	Intermediate Similarity	NPD4634	Approved
0.7404	Intermediate Similarity	NPD7900	Approved
0.7404	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5690	Phase 2
0.7391	Intermediate Similarity	NPD6868	Approved
0.7383	Intermediate Similarity	NPD6404	Discontinued
0.7379	Intermediate Similarity	NPD8035	Phase 2
0.7379	Intermediate Similarity	NPD8034	Phase 2
0.7347	Intermediate Similarity	NPD4223	Phase 3
0.7347	Intermediate Similarity	NPD4221	Approved
0.7339	Intermediate Similarity	NPD4754	Approved
0.73	Intermediate Similarity	NPD5363	Approved
0.73	Intermediate Similarity	NPD5329	Approved
0.73	Intermediate Similarity	NPD1694	Approved
0.7292	Intermediate Similarity	NPD6114	Approved
0.7292	Intermediate Similarity	NPD6118	Approved
0.7292	Intermediate Similarity	NPD6697	Approved
0.7292	Intermediate Similarity	NPD6115	Approved
0.729	Intermediate Similarity	NPD4225	Approved
0.7288	Intermediate Similarity	NPD6319	Approved
0.7282	Intermediate Similarity	NPD5785	Approved
0.7265	Intermediate Similarity	NPD6335	Approved
0.725	Intermediate Similarity	NPD7604	Phase 2
0.7241	Intermediate Similarity	NPD6274	Approved
0.7232	Intermediate Similarity	NPD4729	Approved
0.7232	Intermediate Similarity	NPD5128	Approved
0.7232	Intermediate Similarity	NPD5168	Approved
0.7232	Intermediate Similarity	NPD4730	Approved
0.7228	Intermediate Similarity	NPD4694	Approved
0.7228	Intermediate Similarity	NPD5280	Approved
0.7227	Intermediate Similarity	NPD5983	Phase 2
0.7212	Intermediate Similarity	NPD6050	Approved
0.7207	Intermediate Similarity	NPD4768	Approved
0.7207	Intermediate Similarity	NPD4767	Approved
0.7203	Intermediate Similarity	NPD7101	Approved
0.7203	Intermediate Similarity	NPD7100	Approved
0.72	Intermediate Similarity	NPD4197	Approved
0.72	Intermediate Similarity	NPD3668	Phase 3
0.719	Intermediate Similarity	NPD7492	Approved
0.7184	Intermediate Similarity	NPD6080	Approved
0.7184	Intermediate Similarity	NPD6673	Approved
0.7184	Intermediate Similarity	NPD6904	Approved
0.7179	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7131	Intermediate Similarity	NPD6336	Discontinued
0.7131	Intermediate Similarity	NPD6616	Approved
0.7119	Intermediate Similarity	NPD6314	Approved
0.7119	Intermediate Similarity	NPD6313	Approved
0.7115	Intermediate Similarity	NPD5207	Approved
0.7115	Intermediate Similarity	NPD5692	Phase 3
0.7105	Intermediate Similarity	NPD5247	Approved
0.7105	Intermediate Similarity	NPD5251	Approved
0.7105	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5135	Approved
0.7105	Intermediate Similarity	NPD5248	Approved
0.7105	Intermediate Similarity	NPD5249	Phase 3
0.7105	Intermediate Similarity	NPD5250	Approved
0.7105	Intermediate Similarity	NPD5169	Approved
0.7103	Intermediate Similarity	NPD7614	Phase 1
0.71	Intermediate Similarity	NPD4788	Approved
0.7083	Intermediate Similarity	NPD6117	Approved
0.7083	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6686	Approved
0.7075	Intermediate Similarity	NPD6001	Approved
0.7073	Intermediate Similarity	NPD7078	Approved
0.7059	Intermediate Similarity	NPD4689	Approved
0.7059	Intermediate Similarity	NPD4690	Approved
0.7059	Intermediate Similarity	NPD4138	Approved
0.7059	Intermediate Similarity	NPD5205	Approved
0.7059	Intermediate Similarity	NPD4623	Approved
0.7059	Intermediate Similarity	NPD4519	Discontinued
0.7059	Intermediate Similarity	NPD4688	Approved
0.7059	Intermediate Similarity	NPD4693	Phase 3
0.7048	Intermediate Similarity	NPD5693	Phase 1
0.7048	Intermediate Similarity	NPD5694	Approved
0.7048	Intermediate Similarity	NPD7637	Suspended
0.7043	Intermediate Similarity	NPD5216	Approved
0.7043	Intermediate Similarity	NPD5215	Approved
0.7043	Intermediate Similarity	NPD5127	Approved
0.7043	Intermediate Similarity	NPD5217	Approved
0.7025	Intermediate Similarity	NPD6370	Approved
0.7019	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7736	Approved
0.701	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7507	Approved
0.699	Remote Similarity	NPD3573	Approved
0.699	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7260	Phase 2
0.6983	Remote Similarity	NPD6053	Discontinued
0.6979	Remote Similarity	NPD7339	Approved
0.6979	Remote Similarity	NPD6942	Approved
0.697	Remote Similarity	NPD4695	Discontinued
0.6957	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6908	Approved
0.6942	Remote Similarity	NPD6909	Approved
0.6942	Remote Similarity	NPD6016	Approved
0.6942	Remote Similarity	NPD6015	Approved
0.6939	Remote Similarity	NPD3617	Approved
0.6937	Remote Similarity	NPD5091	Approved
0.6935	Remote Similarity	NPD8293	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