NPASS Compound

Structure

CID95565 OpenBabel06191715432D 36 39 0 0 1 0 0 0 0 0999 V2000 -1.8204 2.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2832 4.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3803 -2.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2557 -2.4560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5349 0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 -1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2240 -0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3795 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3586 3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8209 4.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 2.4374 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3085 4.9693 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8462 4.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 -0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4627 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6897 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -1.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2243 -1.4623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6888 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6900 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8214 5.8136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3800 -1.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5352 -0.4871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9751 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 -0.3591 4.9699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5556 1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0905 -1.9620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3957 -0.7078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3090 6.6576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8467 5.8139 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 19 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 28 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 16 1 1 6 0 0 0 16 20 1 0 0 0 0 17 26 1 0 0 0 0 18 31 2 0 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 20 29 1 6 0 0 0 21 25 1 0 0 0 0 21 32 2 0 0 0 0 22 27 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 0 0 0 0 23 33 1 6 0 0 0 24 30 1 1 0 0 0 24 34 1 0 0 0 0 25 28 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:	502.33
Volume:	535.406
LogP:	3.341
LogD:	3.157
LogS:	-4.123
# Rotatable Bonds:	6
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	5.036
Fsp3:	0.833
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:	-5.318
MDCK Permeability:	1.8129612726625055e-05
Pgp-inhibitor:	0.914
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.318
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.896
Plasma Protein Binding (PPB):	81.98490142822266%
Volume Distribution (VD):	0.429
Pgp-substrate:	14.138631820678711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.478
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.362

ADMET: Excretion

Clearance (CL):	7.092
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.085
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.537
Carcinogencity:	0.315
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC95565

Natural Product ID:	NPC95565
*Common Name:**	Ganolucidic Acid B
IUPAC Name:	(6R)-6-[(3S,5R,10S,13R,14R,15S,17R)-3,15-dihydroxy-4,4,10,13,14-pentamethyl-11-oxo-1,2,3,5,6,7,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
Synonyms:	Ganolucidic Acid B
Standard InCHIKey:	YPYHGMCHNBTMDB-GOGDEKJESA-N
Standard InCHI:	InChI=1S/C30H46O6/c1-16(12-18(31)13-17(2)26(35)36)20-14-24(34)30(7)19-8-9-22-27(3,4)23(33)10-11-28(22,5)25(19)21(32)15-29(20,30)6/h16-17,20,22-24,33-34H,8-15H2,1-7H3,(H,35,36)/t16-,17?,20-,22+,23+,24+,28+,29-,30-/m1/s1
SMILES:	C[C@H](CC(=O)CC(C)C(=O)O)[C@H]1C[C@@H]([C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1922176
PubChem CID:	20055994
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]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	>	199200.0	nM	PMID[525640]
NPT2	Others	Unspecified		IC50	>	600000.0	nM	PMID[525641]

☑ 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 NPC95565 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	203
0.1-0.2	1472
0.2-0.3	5934
0.3-0.4	13412
0.4-0.5	8337
0.5-0.6	6738
0.6-0.7	4906
0.7-0.8	1415
0.8-0.85	168
0.85-0.9	85
0.9-0.95	24
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9663	High Similarity	NPC25750
0.9451	High Similarity	NPC241156
0.9451	High Similarity	NPC255809
0.9368	High Similarity	NPC55872
0.9355	High Similarity	NPC10364
0.9348	High Similarity	NPC125622
0.9341	High Similarity	NPC166906
0.9271	High Similarity	NPC28656
0.9255	High Similarity	NPC88198
0.9255	High Similarity	NPC205899
0.9255	High Similarity	NPC157787
0.9239	High Similarity	NPC317586
0.9239	High Similarity	NPC470016
0.914	High Similarity	NPC96859
0.914	High Similarity	NPC328162
0.914	High Similarity	NPC305483
0.9062	High Similarity	NPC204450
0.9062	High Similarity	NPC56498
0.9062	High Similarity	NPC195290
0.9053	High Similarity	NPC316964
0.9043	High Similarity	NPC18319
0.9032	High Similarity	NPC48330
0.8969	High Similarity	NPC236390
0.8969	High Similarity	NPC33973
0.8969	High Similarity	NPC70967
0.8936	High Similarity	NPC40765
0.8936	High Similarity	NPC243525
0.8936	High Similarity	NPC173272
0.8913	High Similarity	NPC107690
0.8913	High Similarity	NPC23434
0.8878	High Similarity	NPC216245
0.8878	High Similarity	NPC135854
0.8878	High Similarity	NPC470251
0.8878	High Similarity	NPC2436
0.8842	High Similarity	NPC106557
0.8842	High Similarity	NPC43747
0.883	High Similarity	NPC173875
0.883	High Similarity	NPC174948
0.883	High Similarity	NPC469995
0.883	High Similarity	NPC318282
0.883	High Similarity	NPC37646
0.8817	High Similarity	NPC206810
0.8817	High Similarity	NPC470254
0.8791	High Similarity	NPC131470
0.8791	High Similarity	NPC242864
0.8791	High Similarity	NPC143767
0.8788	High Similarity	NPC51452
0.8776	High Similarity	NPC251017
0.8763	High Similarity	NPC124211
0.875	High Similarity	NPC16021
0.875	High Similarity	NPC197386
0.8737	High Similarity	NPC328371
0.8737	High Similarity	NPC3772
0.8723	High Similarity	NPC184870
0.871	High Similarity	NPC297265
0.8696	High Similarity	NPC54689
0.8696	High Similarity	NPC86319
0.8696	High Similarity	NPC275740
0.8673	High Similarity	NPC53222
0.866	High Similarity	NPC144660
0.866	High Similarity	NPC51370
0.866	High Similarity	NPC299971
0.8646	High Similarity	NPC121339
0.8646	High Similarity	NPC320306
0.8646	High Similarity	NPC122294
0.8632	High Similarity	NPC222845
0.8632	High Similarity	NPC200702
0.8632	High Similarity	NPC469599
0.8632	High Similarity	NPC184848
0.8632	High Similarity	NPC162001
0.8632	High Similarity	NPC69548
0.8632	High Similarity	NPC45324
0.8617	High Similarity	NPC470376
0.8617	High Similarity	NPC470375
0.8614	High Similarity	NPC295244
0.8602	High Similarity	NPC183283
0.8602	High Similarity	NPC20388
0.8587	High Similarity	NPC471722
0.8571	High Similarity	NPC163372
0.8571	High Similarity	NPC55309
0.8571	High Similarity	NPC72133
0.8571	High Similarity	NPC302537
0.8571	High Similarity	NPC28252
0.8557	High Similarity	NPC114274
0.8542	High Similarity	NPC7124
0.8515	High Similarity	NPC220974
0.8515	High Similarity	NPC473037
0.8511	High Similarity	NPC63748
0.8511	High Similarity	NPC110657
0.8511	High Similarity	NPC86266
0.8511	High Similarity	NPC212301
0.85	High Similarity	NPC96268
0.85	High Similarity	NPC477812
0.8495	Intermediate Similarity	NPC477943
0.8485	Intermediate Similarity	NPC473424
0.8485	Intermediate Similarity	NPC234892
0.8485	Intermediate Similarity	NPC119601
0.8485	Intermediate Similarity	NPC308726
0.8485	Intermediate Similarity	NPC281702
0.8478	Intermediate Similarity	NPC159046
0.8478	Intermediate Similarity	NPC233836
0.8478	Intermediate Similarity	NPC187376
0.8469	Intermediate Similarity	NPC327431
0.8469	Intermediate Similarity	NPC287833
0.8469	Intermediate Similarity	NPC307954
0.8462	Intermediate Similarity	NPC473038
0.8462	Intermediate Similarity	NPC197823
0.8454	Intermediate Similarity	NPC216904
0.8454	Intermediate Similarity	NPC108078
0.8454	Intermediate Similarity	NPC23680
0.8447	Intermediate Similarity	NPC197428
0.8438	Intermediate Similarity	NPC297199
0.8438	Intermediate Similarity	NPC473648
0.8438	Intermediate Similarity	NPC472932
0.8421	Intermediate Similarity	NPC69454
0.8421	Intermediate Similarity	NPC66429
0.8421	Intermediate Similarity	NPC170220
0.8421	Intermediate Similarity	NPC152897
0.8421	Intermediate Similarity	NPC141497
0.8421	Intermediate Similarity	NPC107674
0.8421	Intermediate Similarity	NPC243866
0.8416	Intermediate Similarity	NPC323834
0.8404	Intermediate Similarity	NPC469400
0.8404	Intermediate Similarity	NPC289213
0.84	Intermediate Similarity	NPC159442
0.8387	Intermediate Similarity	NPC328539
0.8384	Intermediate Similarity	NPC473514
0.837	Intermediate Similarity	NPC472491
0.837	Intermediate Similarity	NPC472494
0.837	Intermediate Similarity	NPC212843
0.8367	Intermediate Similarity	NPC477813
0.8367	Intermediate Similarity	NPC112753
0.8367	Intermediate Similarity	NPC477854
0.8367	Intermediate Similarity	NPC186810
0.8367	Intermediate Similarity	NPC166745
0.8367	Intermediate Similarity	NPC235464
0.8367	Intermediate Similarity	NPC48647
0.8367	Intermediate Similarity	NPC275439
0.8367	Intermediate Similarity	NPC471717
0.8365	Intermediate Similarity	NPC115303
0.8352	Intermediate Similarity	NPC209882
0.8351	Intermediate Similarity	NPC42042
0.8351	Intermediate Similarity	NPC192428
0.8351	Intermediate Similarity	NPC249954
0.8351	Intermediate Similarity	NPC477853
0.835	Intermediate Similarity	NPC77947
0.835	Intermediate Similarity	NPC286174
0.8333	Intermediate Similarity	NPC472925
0.8333	Intermediate Similarity	NPC49670
0.8333	Intermediate Similarity	NPC111015
0.8316	Intermediate Similarity	NPC185936
0.8316	Intermediate Similarity	NPC150383
0.8316	Intermediate Similarity	NPC154101
0.8316	Intermediate Similarity	NPC26888
0.8316	Intermediate Similarity	NPC168027
0.83	Intermediate Similarity	NPC477915
0.83	Intermediate Similarity	NPC136289
0.83	Intermediate Similarity	NPC293753
0.8298	Intermediate Similarity	NPC475921
0.8298	Intermediate Similarity	NPC474889
0.8298	Intermediate Similarity	NPC77168
0.8298	Intermediate Similarity	NPC102414
0.8298	Intermediate Similarity	NPC474704
0.8298	Intermediate Similarity	NPC84271
0.8298	Intermediate Similarity	NPC214387
0.8298	Intermediate Similarity	NPC31985
0.8298	Intermediate Similarity	NPC1015
0.8286	Intermediate Similarity	NPC71348
0.8283	Intermediate Similarity	NPC476274
0.828	Intermediate Similarity	NPC142361
0.828	Intermediate Similarity	NPC138756
0.828	Intermediate Similarity	NPC475740
0.828	Intermediate Similarity	NPC474684
0.828	Intermediate Similarity	NPC312215
0.8269	Intermediate Similarity	NPC473036
0.8269	Intermediate Similarity	NPC272898
0.8269	Intermediate Similarity	NPC129689
0.8265	Intermediate Similarity	NPC18509
0.8265	Intermediate Similarity	NPC190554
0.8252	Intermediate Similarity	NPC65941
0.8247	Intermediate Similarity	NPC263347
0.8247	Intermediate Similarity	NPC259286
0.8242	Intermediate Similarity	NPC168188
0.8242	Intermediate Similarity	NPC470015
0.8235	Intermediate Similarity	NPC278628
0.8235	Intermediate Similarity	NPC149047
0.8235	Intermediate Similarity	NPC231530
0.8229	Intermediate Similarity	NPC477435
0.8229	Intermediate Similarity	NPC472930
0.8229	Intermediate Similarity	NPC477436
0.8218	Intermediate Similarity	NPC264048
0.8218	Intermediate Similarity	NPC36321
0.8218	Intermediate Similarity	NPC140723
0.8211	Intermediate Similarity	NPC148414
0.8211	Intermediate Similarity	NPC477147
0.8211	Intermediate Similarity	NPC111585
0.8211	Intermediate Similarity	NPC136801
0.8211	Intermediate Similarity	NPC477149
0.8211	Intermediate Similarity	NPC191684
0.8211	Intermediate Similarity	NPC175628

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 NPC95565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1964
0.2-0.3	4061
0.3-0.4	1998
0.4-0.5	500
0.5-0.6	158
0.6-0.7	137
0.7-0.8	134
0.8-0.85	18
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD6373	Approved
0.8529	High Similarity	NPD6372	Approved
0.8495	Intermediate Similarity	NPD5328	Approved
0.8416	Intermediate Similarity	NPD5739	Approved
0.8416	Intermediate Similarity	NPD7128	Approved
0.8416	Intermediate Similarity	NPD6675	Approved
0.8416	Intermediate Similarity	NPD6402	Approved
0.8365	Intermediate Similarity	NPD6650	Approved
0.8365	Intermediate Similarity	NPD6649	Approved
0.8351	Intermediate Similarity	NPD4697	Phase 3
0.8316	Intermediate Similarity	NPD6079	Approved
0.8265	Intermediate Similarity	NPD4755	Approved
0.8252	Intermediate Similarity	NPD7320	Approved
0.8252	Intermediate Similarity	NPD6899	Approved
0.8252	Intermediate Similarity	NPD6881	Approved
0.8229	Intermediate Similarity	NPD6399	Phase 3
0.8172	Intermediate Similarity	NPD3618	Phase 1
0.8155	Intermediate Similarity	NPD5701	Approved
0.8155	Intermediate Similarity	NPD5697	Approved
0.81	Intermediate Similarity	NPD5286	Approved
0.81	Intermediate Similarity	NPD4696	Approved
0.81	Intermediate Similarity	NPD5285	Approved
0.81	Intermediate Similarity	NPD4700	Approved
0.8095	Intermediate Similarity	NPD6883	Approved
0.8095	Intermediate Similarity	NPD7290	Approved
0.8095	Intermediate Similarity	NPD7102	Approved
0.8077	Intermediate Similarity	NPD6011	Approved
0.8041	Intermediate Similarity	NPD4202	Approved
0.802	Intermediate Similarity	NPD5223	Approved
0.8019	Intermediate Similarity	NPD6847	Approved
0.8019	Intermediate Similarity	NPD6617	Approved
0.8019	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD6869	Approved
0.8019	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.798	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD5222	Approved
0.798	Intermediate Similarity	NPD5221	Approved
0.7957	Intermediate Similarity	NPD3665	Phase 1
0.7957	Intermediate Similarity	NPD3666	Approved
0.7957	Intermediate Similarity	NPD3133	Approved
0.7957	Intermediate Similarity	NPD4786	Approved
0.7944	Intermediate Similarity	NPD8297	Approved
0.7944	Intermediate Similarity	NPD6882	Approved
0.7941	Intermediate Similarity	NPD5226	Approved
0.7941	Intermediate Similarity	NPD4633	Approved
0.7941	Intermediate Similarity	NPD5211	Phase 2
0.7941	Intermediate Similarity	NPD5224	Approved
0.7941	Intermediate Similarity	NPD5225	Approved
0.7938	Intermediate Similarity	NPD7515	Phase 2
0.7938	Intermediate Similarity	NPD5284	Approved
0.7938	Intermediate Similarity	NPD5281	Approved
0.79	Intermediate Similarity	NPD6083	Phase 2
0.79	Intermediate Similarity	NPD5173	Approved
0.79	Intermediate Similarity	NPD6084	Phase 2
0.7885	Intermediate Similarity	NPD6008	Approved
0.7879	Intermediate Similarity	NPD5695	Phase 3
0.7864	Intermediate Similarity	NPD5175	Approved
0.7864	Intermediate Similarity	NPD4754	Approved
0.7864	Intermediate Similarity	NPD5174	Approved
0.7789	Intermediate Similarity	NPD6409	Approved
0.7789	Intermediate Similarity	NPD6684	Approved
0.7789	Intermediate Similarity	NPD7334	Approved
0.7789	Intermediate Similarity	NPD7521	Approved
0.7789	Intermediate Similarity	NPD5330	Approved
0.7789	Intermediate Similarity	NPD7146	Approved
0.7788	Intermediate Similarity	NPD5141	Approved
0.7742	Intermediate Similarity	NPD3667	Approved
0.7732	Intermediate Similarity	NPD4753	Phase 2
0.7723	Intermediate Similarity	NPD7902	Approved
0.7714	Intermediate Similarity	NPD4767	Approved
0.7714	Intermediate Similarity	NPD4768	Approved
0.7706	Intermediate Similarity	NPD4632	Approved
0.77	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5696	Approved
0.7629	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6903	Approved
0.7604	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5279	Phase 3
0.76	Intermediate Similarity	NPD7748	Approved
0.7589	Intermediate Similarity	NPD6335	Approved
0.7576	Intermediate Similarity	NPD8034	Phase 2
0.7576	Intermediate Similarity	NPD8035	Phase 2
0.757	Intermediate Similarity	NPD5128	Approved
0.757	Intermediate Similarity	NPD4730	Approved
0.757	Intermediate Similarity	NPD4729	Approved
0.7568	Intermediate Similarity	NPD6274	Approved
0.7553	Intermediate Similarity	NPD4223	Phase 3
0.7553	Intermediate Similarity	NPD4221	Approved
0.7525	Intermediate Similarity	NPD5210	Approved
0.7525	Intermediate Similarity	NPD4629	Approved
0.7522	Intermediate Similarity	NPD7101	Approved
0.7522	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7476	Intermediate Similarity	NPD7638	Approved
0.7473	Intermediate Similarity	NPD6117	Approved
0.7449	Intermediate Similarity	NPD5737	Approved
0.7449	Intermediate Similarity	NPD6672	Approved
0.7447	Intermediate Similarity	NPD4692	Approved
0.7447	Intermediate Similarity	NPD4139	Approved
0.7434	Intermediate Similarity	NPD6314	Approved
0.7434	Intermediate Similarity	NPD6313	Approved
0.7431	Intermediate Similarity	NPD5135	Approved
0.7431	Intermediate Similarity	NPD5169	Approved
0.7431	Intermediate Similarity	NPD5248	Approved
0.7431	Intermediate Similarity	NPD5250	Approved
0.7431	Intermediate Similarity	NPD4634	Approved
0.7431	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5251	Approved
0.7431	Intermediate Similarity	NPD5247	Approved
0.7431	Intermediate Similarity	NPD5249	Phase 3
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5690	Phase 2
0.7423	Intermediate Similarity	NPD5280	Approved
0.7423	Intermediate Similarity	NPD4694	Approved
0.7411	Intermediate Similarity	NPD6868	Approved
0.7404	Intermediate Similarity	NPD7640	Approved
0.7404	Intermediate Similarity	NPD7639	Approved
0.74	Intermediate Similarity	NPD6050	Approved
0.7396	Intermediate Similarity	NPD4197	Approved
0.7391	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6116	Phase 1
0.7391	Intermediate Similarity	NPD6909	Approved
0.7391	Intermediate Similarity	NPD6908	Approved
0.7374	Intermediate Similarity	NPD6673	Approved
0.7374	Intermediate Similarity	NPD6904	Approved
0.7374	Intermediate Similarity	NPD6080	Approved
0.7364	Intermediate Similarity	NPD5215	Approved
0.7364	Intermediate Similarity	NPD5127	Approved
0.7364	Intermediate Similarity	NPD5216	Approved
0.7364	Intermediate Similarity	NPD5217	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.734	Intermediate Similarity	NPD4748	Discontinued
0.7312	Intermediate Similarity	NPD6118	Approved
0.7312	Intermediate Similarity	NPD6115	Approved
0.7312	Intermediate Similarity	NPD6114	Approved
0.7312	Intermediate Similarity	NPD6697	Approved
0.7312	Intermediate Similarity	NPD3617	Approved
0.7304	Intermediate Similarity	NPD6319	Approved
0.73	Intermediate Similarity	NPD5692	Phase 3
0.73	Intermediate Similarity	NPD5207	Approved
0.7292	Intermediate Similarity	NPD4788	Approved
0.7265	Intermediate Similarity	NPD7604	Phase 2
0.7264	Intermediate Similarity	NPD7632	Discontinued
0.7255	Intermediate Similarity	NPD6001	Approved
0.7253	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5168	Approved
0.7245	Intermediate Similarity	NPD4138	Approved
0.7245	Intermediate Similarity	NPD4690	Approved
0.7245	Intermediate Similarity	NPD4693	Phase 3
0.7245	Intermediate Similarity	NPD5205	Approved
0.7245	Intermediate Similarity	NPD4689	Approved
0.7245	Intermediate Similarity	NPD4688	Approved
0.7241	Intermediate Similarity	NPD5983	Phase 2
0.7228	Intermediate Similarity	NPD6411	Approved
0.7228	Intermediate Similarity	NPD5694	Approved
0.7216	Intermediate Similarity	NPD3668	Phase 3
0.7203	Intermediate Similarity	NPD7492	Approved
0.72	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5167	Approved
0.7155	Intermediate Similarity	NPD6059	Approved
0.7155	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD6616	Approved
0.71	Intermediate Similarity	NPD5208	Approved
0.7097	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7078	Approved
0.7083	Intermediate Similarity	NPD8293	Discontinued
0.7071	Intermediate Similarity	NPD6098	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7034	Intermediate Similarity	NPD6370	Approved
0.7033	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7736	Approved
0.7019	Intermediate Similarity	NPD5654	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD3573	Approved
0.6991	Remote Similarity	NPD6053	Discontinued
0.699	Remote Similarity	NPD5133	Approved
0.6989	Remote Similarity	NPD6942	Approved
0.6989	Remote Similarity	NPD7339	Approved
0.6989	Remote Similarity	NPD3703	Phase 2
0.6979	Remote Similarity	NPD5368	Approved
0.6979	Remote Similarity	NPD7525	Registered
0.697	Remote Similarity	NPD5363	Approved
0.6961	Remote Similarity	NPD5785	Approved
0.6961	Remote Similarity	NPD4096	Approved
0.6949	Remote Similarity	NPD6015	Approved
0.6949	Remote Similarity	NPD6016	Approved
0.6931	Remote Similarity	NPD4518	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