NPASS Compound

Structure

CID235464 OpenBabel06191716032D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.0017 2.9229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0026 5.8449 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 -1.6890 3.8964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 2.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 4.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4622 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 1.6885 0.9749 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 0.8440 1.4621 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 -0.8451 2.4357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 5.3576 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 -0.8448 1.4617 0.0000 C 0 0 2 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 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6896 5.8444 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 1 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 1 0 0 0 0 0 0 0 0 0 5.0874 -1.9610 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 -1.6899 6.8184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5329 5.3572 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 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 18 1 0 0 0 0 10 19 2 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 1 1 1 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 22 29 1 6 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 31 2 0 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 26 33 2 0 0 0 0 26 34 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:	468.32
Volume:	515.189
LogP:	5.548
LogD:	4.621
LogS:	-4.554
# Rotatable Bonds:	5
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	5.01
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.2
MDCK Permeability:	2.6398796762805432e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	90.5921859741211%
Volume Distribution (VD):	0.608
Pgp-substrate:	4.201667308807373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.607
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.303
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.272
CYP3A4-inhibitor:	0.278
CYP3A4-substrate:	0.438

ADMET: Excretion

Clearance (CL):	5.519
Half-life (T1/2):	0.693

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.852
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.602
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.969
Carcinogencity:	0.522
Eye Corrosion:	0.02
Eye Irritation:	0.089
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC235464

Natural Product ID:	NPC235464
*Common Name:**	Ganoderic Acid Tr
IUPAC Name:	(Z,6R)-6-[(5R,10S,13R,14R,15S,17R)-15-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Synonyms:	Ganoderic Acid Tr
Standard InCHIKey:	SNZQBBATMLGADX-OYLOMWMRSA-N
Standard InCHI:	InChI=1S/C30H44O4/c1-18(9-8-10-19(2)26(33)34)22-17-25(32)30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(22,30)6/h10-11,13,18,22-23,25,32H,8-9,12,14-17H2,1-7H3,(H,33,34)/b19-10-/t18-,22-,23+,25+,28-,29-,30-/m1/s1
SMILES:	C[C@@H]([C@H]1C[C@@H]([C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)O)CC/C=C(C(=O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097474
PubChem CID:	46888170
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]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	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]
NPO16609	Ganoderma sinense	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
EC50	1
IC50	2

Activity Type	# Activity
Organism	1
Others	1
PROTEIN COMPLEX	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	20000.0	nM	PMID[524081]
NPT22802	PROTEIN COMPLEX	Bile acid receptor/Retinoic acid receptor RXR-alpha	Mus musculus	EC50	>	14000.0	nM	PMID[524082]
NPT2	Others	Unspecified		IC50	=	8500.0	nM	PMID[524083]

☑ 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 NPC235464 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	167
0.1-0.2	909
0.2-0.3	3959
0.3-0.4	10768
0.4-0.5	11739
0.5-0.6	7344
0.6-0.7	5597
0.7-0.8	1791
0.8-0.85	308
0.85-0.9	75
0.9-0.95	33
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC166745
0.9574	High Similarity	NPC99411
0.957	High Similarity	NPC197386
0.9239	High Similarity	NPC472942
0.9231	High Similarity	NPC69622
0.9158	High Similarity	NPC471717
0.9149	High Similarity	NPC472941
0.9149	High Similarity	NPC456
0.9149	High Similarity	NPC155676
0.9072	High Similarity	NPC195290
0.9072	High Similarity	NPC204450
0.9043	High Similarity	NPC472932
0.9043	High Similarity	NPC173875
0.9043	High Similarity	NPC318282
0.9043	High Similarity	NPC469995
0.9043	High Similarity	NPC174948
0.9032	High Similarity	NPC66429
0.9032	High Similarity	NPC250575
0.9032	High Similarity	NPC152897
0.898	High Similarity	NPC236390
0.8958	High Similarity	NPC48647
0.8947	High Similarity	NPC328371
0.8936	High Similarity	NPC469406
0.8925	High Similarity	NPC204341
0.8913	High Similarity	NPC214387
0.8866	High Similarity	NPC287833
0.8854	High Similarity	NPC18319
0.8854	High Similarity	NPC320306
0.8842	High Similarity	NPC263347
0.8842	High Similarity	NPC476174
0.883	High Similarity	NPC214697
0.883	High Similarity	NPC243866
0.8817	High Similarity	NPC477149
0.8817	High Similarity	NPC477147
0.8776	High Similarity	NPC472924
0.8763	High Similarity	NPC10364
0.8763	High Similarity	NPC186810
0.875	High Similarity	NPC301534
0.875	High Similarity	NPC250757
0.8723	High Similarity	NPC45269
0.8723	High Similarity	NPC212948
0.871	High Similarity	NPC54689
0.8687	High Similarity	NPC293753
0.8687	High Similarity	NPC473424
0.8681	High Similarity	NPC474083
0.8673	High Similarity	NPC51370
0.8673	High Similarity	NPC205899
0.8673	High Similarity	NPC327431
0.866	High Similarity	NPC141401
0.866	High Similarity	NPC475894
0.866	High Similarity	NPC107243
0.8646	High Similarity	NPC222845
0.8646	High Similarity	NPC162001
0.8646	High Similarity	NPC45324
0.8632	High Similarity	NPC474736
0.8632	High Similarity	NPC472930
0.8632	High Similarity	NPC25750
0.8632	High Similarity	NPC206810
0.8627	High Similarity	NPC220155
0.8617	High Similarity	NPC48010
0.8617	High Similarity	NPC46281
0.8602	High Similarity	NPC48866
0.8602	High Similarity	NPC247406
0.86	High Similarity	NPC111323
0.8587	High Similarity	NPC469994
0.8586	High Similarity	NPC163372
0.8586	High Similarity	NPC302537
0.8571	High Similarity	NPC473246
0.8571	High Similarity	NPC165064
0.8571	High Similarity	NPC164577
0.8571	High Similarity	NPC87552
0.8557	High Similarity	NPC29152
0.8542	High Similarity	NPC184870
0.8542	High Similarity	NPC7165
0.8542	High Similarity	NPC166906
0.8529	High Similarity	NPC472925
0.8529	High Similarity	NPC91034
0.8526	High Similarity	NPC474018
0.8526	High Similarity	NPC473986
0.8526	High Similarity	NPC154101
0.8526	High Similarity	NPC473998
0.8515	High Similarity	NPC472868
0.8511	High Similarity	NPC84271
0.8511	High Similarity	NPC155479
0.8511	High Similarity	NPC309603
0.8511	High Similarity	NPC477943
0.8511	High Similarity	NPC262043
0.8511	High Similarity	NPC77168
0.8511	High Similarity	NPC473999
0.8511	High Similarity	NPC310236
0.8511	High Similarity	NPC123912
0.8511	High Similarity	NPC2983
0.8511	High Similarity	NPC146554
0.8511	High Similarity	NPC102414
0.85	High Similarity	NPC56498
0.85	High Similarity	NPC119601
0.85	High Similarity	NPC234892
0.85	High Similarity	NPC87351
0.85	High Similarity	NPC308726
0.8495	Intermediate Similarity	NPC136548
0.8495	Intermediate Similarity	NPC287079
0.8495	Intermediate Similarity	NPC317590
0.8495	Intermediate Similarity	NPC312215
0.8495	Intermediate Similarity	NPC136948
0.8485	Intermediate Similarity	NPC476274
0.8485	Intermediate Similarity	NPC266955
0.8478	Intermediate Similarity	NPC471224
0.8476	Intermediate Similarity	NPC191620
0.8469	Intermediate Similarity	NPC253826
0.8469	Intermediate Similarity	NPC57416
0.8469	Intermediate Similarity	NPC108078
0.8469	Intermediate Similarity	NPC469432
0.8469	Intermediate Similarity	NPC156546
0.8462	Intermediate Similarity	NPC470015
0.8462	Intermediate Similarity	NPC97913
0.8462	Intermediate Similarity	NPC69279
0.8462	Intermediate Similarity	NPC168188
0.8462	Intermediate Similarity	NPC83569
0.8454	Intermediate Similarity	NPC37646
0.8454	Intermediate Similarity	NPC317586
0.8454	Intermediate Similarity	NPC470016
0.8454	Intermediate Similarity	NPC241156
0.8454	Intermediate Similarity	NPC171395
0.8454	Intermediate Similarity	NPC469599
0.8447	Intermediate Similarity	NPC295244
0.8438	Intermediate Similarity	NPC69454
0.8421	Intermediate Similarity	NPC469400
0.8421	Intermediate Similarity	NPC123854
0.8421	Intermediate Similarity	NPC320026
0.8416	Intermediate Similarity	NPC85742
0.8416	Intermediate Similarity	NPC311612
0.8416	Intermediate Similarity	NPC55872
0.8404	Intermediate Similarity	NPC471722
0.8404	Intermediate Similarity	NPC193843
0.8404	Intermediate Similarity	NPC72397
0.8404	Intermediate Similarity	NPC242864
0.8404	Intermediate Similarity	NPC294480
0.8404	Intermediate Similarity	NPC249889
0.84	Intermediate Similarity	NPC476240
0.84	Intermediate Similarity	NPC224720
0.84	Intermediate Similarity	NPC282524
0.84	Intermediate Similarity	NPC115899
0.84	Intermediate Similarity	NPC146822
0.84	Intermediate Similarity	NPC476223
0.8387	Intermediate Similarity	NPC155011
0.8387	Intermediate Similarity	NPC474732
0.8387	Intermediate Similarity	NPC118648
0.8387	Intermediate Similarity	NPC474778
0.8387	Intermediate Similarity	NPC474733
0.8387	Intermediate Similarity	NPC475022
0.8387	Intermediate Similarity	NPC31564
0.8387	Intermediate Similarity	NPC212843
0.8387	Intermediate Similarity	NPC145879
0.8387	Intermediate Similarity	NPC222613
0.8384	Intermediate Similarity	NPC478056
0.8384	Intermediate Similarity	NPC477813
0.8384	Intermediate Similarity	NPC108368
0.8384	Intermediate Similarity	NPC57079
0.8384	Intermediate Similarity	NPC103051
0.8381	Intermediate Similarity	NPC474315
0.837	Intermediate Similarity	NPC58841
0.837	Intermediate Similarity	NPC82902
0.837	Intermediate Similarity	NPC161423
0.837	Intermediate Similarity	NPC214043
0.837	Intermediate Similarity	NPC472865
0.837	Intermediate Similarity	NPC227064
0.837	Intermediate Similarity	NPC321187
0.837	Intermediate Similarity	NPC85774
0.837	Intermediate Similarity	NPC329043
0.8367	Intermediate Similarity	NPC7124
0.8367	Intermediate Similarity	NPC96859
0.8367	Intermediate Similarity	NPC117133
0.8367	Intermediate Similarity	NPC243525
0.8367	Intermediate Similarity	NPC249954
0.8367	Intermediate Similarity	NPC125622
0.8367	Intermediate Similarity	NPC3772
0.8367	Intermediate Similarity	NPC190713
0.8367	Intermediate Similarity	NPC173272
0.8367	Intermediate Similarity	NPC305483
0.8367	Intermediate Similarity	NPC40765
0.8367	Intermediate Similarity	NPC95565
0.8367	Intermediate Similarity	NPC328162
0.8352	Intermediate Similarity	NPC260956
0.8352	Intermediate Similarity	NPC3511
0.8352	Intermediate Similarity	NPC142253
0.8351	Intermediate Similarity	NPC8993
0.8351	Intermediate Similarity	NPC474690
0.8351	Intermediate Similarity	NPC299100
0.8333	Intermediate Similarity	NPC63748
0.8333	Intermediate Similarity	NPC235889
0.8333	Intermediate Similarity	NPC233116
0.8333	Intermediate Similarity	NPC19114
0.8333	Intermediate Similarity	NPC107690
0.8333	Intermediate Similarity	NPC28656
0.8333	Intermediate Similarity	NPC23434
0.8333	Intermediate Similarity	NPC475806
0.8317	Intermediate Similarity	NPC136289
0.8316	Intermediate Similarity	NPC1015
0.8316	Intermediate Similarity	NPC262858
0.8316	Intermediate Similarity	NPC31985

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 NPC235464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1164
0.2-0.3	3570
0.3-0.4	2852
0.4-0.5	861
0.5-0.6	223
0.6-0.7	167
0.7-0.8	157
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD5281	Approved
0.8526	High Similarity	NPD5284	Approved
0.8387	Intermediate Similarity	NPD5279	Phase 3
0.837	Intermediate Similarity	NPD3133	Approved
0.837	Intermediate Similarity	NPD3666	Approved
0.837	Intermediate Similarity	NPD3665	Phase 1
0.8283	Intermediate Similarity	NPD6083	Phase 2
0.8283	Intermediate Similarity	NPD6084	Phase 2
0.8265	Intermediate Similarity	NPD5695	Phase 3
0.8191	Intermediate Similarity	NPD5330	Approved
0.8191	Intermediate Similarity	NPD6409	Approved
0.8191	Intermediate Similarity	NPD7334	Approved
0.8191	Intermediate Similarity	NPD4694	Approved
0.8191	Intermediate Similarity	NPD6684	Approved
0.8191	Intermediate Similarity	NPD7521	Approved
0.8191	Intermediate Similarity	NPD5280	Approved
0.8191	Intermediate Similarity	NPD7146	Approved
0.8172	Intermediate Similarity	NPD4786	Approved
0.8144	Intermediate Similarity	NPD6050	Approved
0.8125	Intermediate Similarity	NPD4753	Phase 2
0.8061	Intermediate Similarity	NPD6399	Phase 3
0.8041	Intermediate Similarity	NPD5692	Phase 3
0.8021	Intermediate Similarity	NPD6903	Approved
0.8021	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5690	Phase 2
0.7961	Intermediate Similarity	NPD5211	Phase 2
0.7959	Intermediate Similarity	NPD5694	Approved
0.7959	Intermediate Similarity	NPD6079	Approved
0.7957	Intermediate Similarity	NPD4223	Phase 3
0.7957	Intermediate Similarity	NPD3667	Approved
0.7957	Intermediate Similarity	NPD4221	Approved
0.7941	Intermediate Similarity	NPD6404	Discontinued
0.7938	Intermediate Similarity	NPD5328	Approved
0.7925	Intermediate Similarity	NPD6899	Approved
0.7925	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD5739	Approved
0.7905	Intermediate Similarity	NPD6675	Approved
0.7905	Intermediate Similarity	NPD6402	Approved
0.7905	Intermediate Similarity	NPD7128	Approved
0.79	Intermediate Similarity	NPD4629	Approved
0.79	Intermediate Similarity	NPD5210	Approved
0.7895	Intermediate Similarity	NPD5363	Approved
0.7895	Intermediate Similarity	NPD5329	Approved
0.7879	Intermediate Similarity	NPD4202	Approved
0.7857	Intermediate Similarity	NPD5207	Approved
0.7857	Intermediate Similarity	NPD5785	Approved
0.7843	Intermediate Similarity	NPD5696	Approved
0.7835	Intermediate Similarity	NPD6672	Approved
0.7835	Intermediate Similarity	NPD5737	Approved
0.783	Intermediate Similarity	NPD5697	Approved
0.7812	Intermediate Similarity	NPD3618	Phase 1
0.781	Intermediate Similarity	NPD5141	Approved
0.7789	Intermediate Similarity	NPD4197	Approved
0.7778	Intermediate Similarity	NPD7290	Approved
0.7778	Intermediate Similarity	NPD7515	Phase 2
0.7778	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD6883	Approved
0.7767	Intermediate Similarity	NPD5286	Approved
0.7767	Intermediate Similarity	NPD4696	Approved
0.7767	Intermediate Similarity	NPD5285	Approved
0.7767	Intermediate Similarity	NPD7640	Approved
0.7767	Intermediate Similarity	NPD7639	Approved
0.7757	Intermediate Similarity	NPD7320	Approved
0.7757	Intermediate Similarity	NPD6011	Approved
0.7755	Intermediate Similarity	NPD6904	Approved
0.7755	Intermediate Similarity	NPD6673	Approved
0.7755	Intermediate Similarity	NPD6080	Approved
0.7755	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD4755	Approved
0.7717	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD8130	Phase 1
0.7706	Intermediate Similarity	NPD6649	Approved
0.7706	Intermediate Similarity	NPD6617	Approved
0.7706	Intermediate Similarity	NPD6650	Approved
0.7706	Intermediate Similarity	NPD6847	Approved
0.7706	Intermediate Similarity	NPD6869	Approved
0.7692	Intermediate Similarity	NPD5223	Approved
0.7685	Intermediate Similarity	NPD6014	Approved
0.7685	Intermediate Similarity	NPD6012	Approved
0.7685	Intermediate Similarity	NPD6373	Approved
0.7685	Intermediate Similarity	NPD6013	Approved
0.7685	Intermediate Similarity	NPD6372	Approved
0.7684	Intermediate Similarity	NPD4788	Approved
0.7684	Intermediate Similarity	NPD5362	Discontinued
0.7679	Intermediate Similarity	NPD7115	Discovery
0.7677	Intermediate Similarity	NPD4096	Approved
0.767	Intermediate Similarity	NPD7638	Approved
0.7664	Intermediate Similarity	NPD5701	Approved
0.7653	Intermediate Similarity	NPD4518	Approved
0.7647	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5222	Approved
0.7647	Intermediate Similarity	NPD5221	Approved
0.7636	Intermediate Similarity	NPD6882	Approved
0.7636	Intermediate Similarity	NPD8297	Approved
0.7629	Intermediate Similarity	NPD5205	Approved
0.7629	Intermediate Similarity	NPD4138	Approved
0.7629	Intermediate Similarity	NPD4689	Approved
0.7629	Intermediate Similarity	NPD4688	Approved
0.7629	Intermediate Similarity	NPD4693	Phase 3
0.7629	Intermediate Similarity	NPD4690	Approved
0.7619	Intermediate Similarity	NPD5224	Approved
0.7619	Intermediate Similarity	NPD4633	Approved
0.7619	Intermediate Similarity	NPD5226	Approved
0.7619	Intermediate Similarity	NPD5225	Approved
0.76	Intermediate Similarity	NPD5693	Phase 1
0.7596	Intermediate Similarity	NPD4700	Approved
0.7579	Intermediate Similarity	NPD4270	Approved
0.7579	Intermediate Similarity	NPD4269	Approved
0.7573	Intermediate Similarity	NPD5173	Approved
0.7549	Intermediate Similarity	NPD5654	Approved
0.7549	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5174	Approved
0.7547	Intermediate Similarity	NPD5175	Approved
0.7545	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5133	Approved
0.7476	Intermediate Similarity	NPD4697	Phase 3
0.7475	Intermediate Similarity	NPD5208	Approved
0.7473	Intermediate Similarity	NPD5733	Approved
0.7451	Intermediate Similarity	NPD7748	Approved
0.7449	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6098	Approved
0.7447	Intermediate Similarity	NPD4195	Approved
0.7426	Intermediate Similarity	NPD7637	Suspended
0.7426	Intermediate Similarity	NPD6411	Approved
0.7423	Intermediate Similarity	NPD3668	Phase 3
0.7411	Intermediate Similarity	NPD4632	Approved
0.7404	Intermediate Similarity	NPD5959	Approved
0.7383	Intermediate Similarity	NPD4754	Approved
0.7368	Intermediate Similarity	NPD4252	Approved
0.7368	Intermediate Similarity	NPD4695	Discontinued
0.7353	Intermediate Similarity	NPD5779	Approved
0.7353	Intermediate Similarity	NPD5778	Approved
0.7347	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6412	Phase 2
0.7321	Intermediate Similarity	NPD6053	Discontinued
0.732	Intermediate Similarity	NPD5332	Approved
0.732	Intermediate Similarity	NPD5331	Approved
0.7312	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6335	Approved
0.7292	Intermediate Similarity	NPD4139	Approved
0.7292	Intermediate Similarity	NPD4790	Discontinued
0.7292	Intermediate Similarity	NPD4692	Approved
0.7283	Intermediate Similarity	NPD4687	Approved
0.7281	Intermediate Similarity	NPD6274	Approved
0.7273	Intermediate Similarity	NPD4623	Approved
0.7273	Intermediate Similarity	NPD4519	Discontinued
0.7273	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD5128	Approved
0.7273	Intermediate Similarity	NPD5786	Approved
0.7273	Intermediate Similarity	NPD4730	Approved
0.7253	Intermediate Similarity	NPD5276	Approved
0.7248	Intermediate Similarity	NPD4768	Approved
0.7248	Intermediate Similarity	NPD6008	Approved
0.7248	Intermediate Similarity	NPD4767	Approved
0.7241	Intermediate Similarity	NPD7100	Approved
0.7241	Intermediate Similarity	NPD7101	Approved
0.7238	Intermediate Similarity	NPD7902	Approved
0.7228	Intermediate Similarity	NPD6051	Approved
0.7228	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6101	Approved
0.7217	Intermediate Similarity	NPD6009	Approved
0.7217	Intermediate Similarity	NPD6317	Approved
0.7216	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7339	Approved
0.7204	Intermediate Similarity	NPD6942	Approved
0.72	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4822	Approved
0.7188	Intermediate Similarity	NPD4820	Approved
0.7188	Intermediate Similarity	NPD4821	Approved
0.7188	Intermediate Similarity	NPD4819	Approved
0.7158	Intermediate Similarity	NPD4268	Approved
0.7158	Intermediate Similarity	NPD3617	Approved
0.7158	Intermediate Similarity	NPD4271	Approved
0.7155	Intermediate Similarity	NPD6313	Approved
0.7155	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD7632	Discontinued
0.7115	Intermediate Similarity	NPD6001	Approved
0.7113	Intermediate Similarity	NPD5369	Approved
0.7097	Intermediate Similarity	NPD6926	Approved
0.7097	Intermediate Similarity	NPD4058	Approved
0.7097	Intermediate Similarity	NPD6924	Approved
0.7083	Intermediate Similarity	NPD6929	Approved
0.708	Intermediate Similarity	NPD5127	Approved
0.708	Intermediate Similarity	NPD5215	Approved
0.708	Intermediate Similarity	NPD5217	Approved
0.708	Intermediate Similarity	NPD5216	Approved
0.7034	Intermediate Similarity	NPD6319	Approved
0.701	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6931	Approved

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