NPASS Compound

Structure

CID25750 OpenBabel06191715352D 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 0 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 2 0 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:	500.31
Volume:	532.769
LogP:	3.044
LogD:	2.753
LogS:	-4.199
# Rotatable Bonds:	6
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.521
Synthetic Accessibility Score:	4.998
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:	-5.334
MDCK Permeability:	1.613802851352375e-05
Pgp-inhibitor:	0.708
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.927
Plasma Protein Binding (PPB):	80.45668029785156%
Volume Distribution (VD):	0.496
Pgp-substrate:	11.54751968383789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.487

ADMET: Excretion

Clearance (CL):	5.75
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.149
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.6
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.255
Carcinogencity:	0.554
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC25750

Natural Product ID:	NPC25750
*Common Name:**	Ganolucidic Acid A
IUPAC Name:	(6R)-6-[(5R,10S,13R,14R,15S,17R)-15-hydroxy-4,4,10,13,14-pentamethyl-3,11-dioxo-2,5,6,7,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
Synonyms:
Standard InCHIKey:	XRXBNTYHQXKSAO-SXTFGQQDSA-N
Standard InCHI:	InChI=1S/C30H44O6/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/h16-17,20,22,24,34H,8-15H2,1-7H3,(H,35,36)/t16-,17?,20-,22+,24+,28+,29-,30-/m1/s1
SMILES:	O=C(CC(C(=O)O)C)C[C@H]([C@H]1C[C@@H]([C@@]2([C@]1(C)CC(=O)C1=C2CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087131
PubChem CID:	20055993
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
IC50	4
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	22.0	%	PMID[502294]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	22970.0	nM	PMID[502296]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	>	200000.0	nM	PMID[502296]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	101000.0	nM	PMID[502297]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25340.0	nM	PMID[502298]
NPT27	Others	Unspecified		Activity	=	95.16	%	PMID[502298]

☑ 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 NPC25750 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	194
0.1-0.2	1411
0.2-0.3	6420
0.3-0.4	14011
0.4-0.5	7681
0.5-0.6	6717
0.6-0.7	4832
0.7-0.8	1154
0.8-0.85	183
0.85-0.9	59
0.9-0.95	27
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC241156
0.9663	High Similarity	NPC125622
0.9663	High Similarity	NPC95565
0.9451	High Similarity	NPC10364
0.9348	High Similarity	NPC205899
0.9149	High Similarity	NPC204450
0.9149	High Similarity	NPC195290
0.9149	High Similarity	NPC56498
0.913	High Similarity	NPC18319
0.9121	High Similarity	NPC255809
0.9111	High Similarity	NPC206810
0.9053	High Similarity	NPC236390
0.9053	High Similarity	NPC55872
0.9032	High Similarity	NPC197386
0.9022	High Similarity	NPC40765
0.9022	High Similarity	NPC243525
0.9011	High Similarity	NPC166906
0.9	High Similarity	NPC107690
0.8989	High Similarity	NPC54689
0.8958	High Similarity	NPC28656
0.8936	High Similarity	NPC88198
0.8936	High Similarity	NPC157787
0.8925	High Similarity	NPC106557
0.8913	High Similarity	NPC37646
0.8913	High Similarity	NPC318282
0.8913	High Similarity	NPC317586
0.8913	High Similarity	NPC470016
0.8913	High Similarity	NPC173875
0.8913	High Similarity	NPC469995
0.8913	High Similarity	NPC174948
0.8901	High Similarity	NPC470254
0.8817	High Similarity	NPC328162
0.8817	High Similarity	NPC3772
0.8817	High Similarity	NPC328371
0.8817	High Similarity	NPC305483
0.8817	High Similarity	NPC96859
0.8804	High Similarity	NPC184870
0.8778	High Similarity	NPC477943
0.875	High Similarity	NPC473038
0.8737	High Similarity	NPC51370
0.8737	High Similarity	NPC316964
0.8723	High Similarity	NPC121339
0.8723	High Similarity	NPC43747
0.871	High Similarity	NPC469599
0.871	High Similarity	NPC472932
0.871	High Similarity	NPC48330
0.8696	High Similarity	NPC243866
0.8696	High Similarity	NPC152897
0.8696	High Similarity	NPC66429
0.8681	High Similarity	NPC289213
0.866	High Similarity	NPC33973
0.866	High Similarity	NPC70967
0.8652	High Similarity	NPC212843
0.8646	High Similarity	NPC124211
0.8636	High Similarity	NPC209882
0.8632	High Similarity	NPC166745
0.8632	High Similarity	NPC235464
0.8617	High Similarity	NPC173272
0.8617	High Similarity	NPC42042
0.8587	High Similarity	NPC150383
0.8587	High Similarity	NPC23434
0.8587	High Similarity	NPC154101
0.8571	High Similarity	NPC470251
0.8571	High Similarity	NPC216245
0.8571	High Similarity	NPC2436
0.8571	High Similarity	NPC135854
0.8557	High Similarity	NPC53222
0.8556	High Similarity	NPC312215
0.8542	High Similarity	NPC287833
0.8523	High Similarity	NPC168188
0.8523	High Similarity	NPC470015
0.8511	High Similarity	NPC263347
0.8485	Intermediate Similarity	NPC51452
0.8469	Intermediate Similarity	NPC251017
0.8462	Intermediate Similarity	NPC242864
0.8462	Intermediate Similarity	NPC131470
0.8462	Intermediate Similarity	NPC143767
0.8462	Intermediate Similarity	NPC183546
0.8462	Intermediate Similarity	NPC294480
0.8454	Intermediate Similarity	NPC163372
0.8454	Intermediate Similarity	NPC302537
0.8438	Intermediate Similarity	NPC471717
0.8438	Intermediate Similarity	NPC16021
0.8427	Intermediate Similarity	NPC473246
0.8421	Intermediate Similarity	NPC155676
0.8387	Intermediate Similarity	NPC297265
0.8384	Intermediate Similarity	NPC235889
0.837	Intermediate Similarity	NPC275740
0.837	Intermediate Similarity	NPC214387
0.837	Intermediate Similarity	NPC155479
0.837	Intermediate Similarity	NPC86319
0.8367	Intermediate Similarity	NPC308726
0.8367	Intermediate Similarity	NPC119601
0.8352	Intermediate Similarity	NPC99909
0.8351	Intermediate Similarity	NPC144660
0.8351	Intermediate Similarity	NPC218383
0.8351	Intermediate Similarity	NPC474720
0.8351	Intermediate Similarity	NPC299971
0.8333	Intermediate Similarity	NPC122294
0.8333	Intermediate Similarity	NPC474218
0.8333	Intermediate Similarity	NPC94531
0.8333	Intermediate Similarity	NPC320306
0.8333	Intermediate Similarity	NPC216904
0.8333	Intermediate Similarity	NPC123319
0.8333	Intermediate Similarity	NPC311702
0.8333	Intermediate Similarity	NPC469948
0.8317	Intermediate Similarity	NPC295244
0.8316	Intermediate Similarity	NPC184848
0.8316	Intermediate Similarity	NPC45324
0.8316	Intermediate Similarity	NPC69548
0.8316	Intermediate Similarity	NPC222845
0.8316	Intermediate Similarity	NPC162001
0.8316	Intermediate Similarity	NPC200702
0.8315	Intermediate Similarity	NPC469561
0.8315	Intermediate Similarity	NPC271784
0.83	Intermediate Similarity	NPC181265
0.8298	Intermediate Similarity	NPC470376
0.8298	Intermediate Similarity	NPC470375
0.8298	Intermediate Similarity	NPC250575
0.8298	Intermediate Similarity	NPC472930
0.8283	Intermediate Similarity	NPC111323
0.828	Intermediate Similarity	NPC46281
0.828	Intermediate Similarity	NPC183283
0.828	Intermediate Similarity	NPC477147
0.828	Intermediate Similarity	NPC477149
0.828	Intermediate Similarity	NPC20388
0.8265	Intermediate Similarity	NPC99411
0.8265	Intermediate Similarity	NPC472924
0.8265	Intermediate Similarity	NPC474327
0.8261	Intermediate Similarity	NPC48866
0.8261	Intermediate Similarity	NPC471722
0.8261	Intermediate Similarity	NPC247406
0.8247	Intermediate Similarity	NPC275439
0.8247	Intermediate Similarity	NPC114274
0.8247	Intermediate Similarity	NPC112753
0.8247	Intermediate Similarity	NPC147954
0.8242	Intermediate Similarity	NPC472494
0.8242	Intermediate Similarity	NPC31564
0.8242	Intermediate Similarity	NPC474732
0.8242	Intermediate Similarity	NPC222613
0.8242	Intermediate Similarity	NPC474778
0.8242	Intermediate Similarity	NPC474733
0.8242	Intermediate Similarity	NPC28252
0.8242	Intermediate Similarity	NPC55309
0.8242	Intermediate Similarity	NPC118648
0.8242	Intermediate Similarity	NPC145879
0.8242	Intermediate Similarity	NPC475022
0.8242	Intermediate Similarity	NPC472491
0.8242	Intermediate Similarity	NPC155011
0.8242	Intermediate Similarity	NPC72133
0.8235	Intermediate Similarity	NPC258543
0.8235	Intermediate Similarity	NPC304495
0.8235	Intermediate Similarity	NPC241927
0.8229	Intermediate Similarity	NPC472941
0.8229	Intermediate Similarity	NPC456
0.8229	Intermediate Similarity	NPC7124
0.8222	Intermediate Similarity	NPC82902
0.8222	Intermediate Similarity	NPC58841
0.8222	Intermediate Similarity	NPC321187
0.8222	Intermediate Similarity	NPC161423
0.8222	Intermediate Similarity	NPC227064
0.8222	Intermediate Similarity	NPC85774
0.8222	Intermediate Similarity	NPC329043
0.8222	Intermediate Similarity	NPC109512
0.8222	Intermediate Similarity	NPC214043
0.8218	Intermediate Similarity	NPC220974
0.8218	Intermediate Similarity	NPC473037
0.8202	Intermediate Similarity	NPC133391
0.8202	Intermediate Similarity	NPC260956
0.8202	Intermediate Similarity	NPC321289
0.8202	Intermediate Similarity	NPC327969
0.82	Intermediate Similarity	NPC119493
0.82	Intermediate Similarity	NPC96268
0.82	Intermediate Similarity	NPC477812
0.8191	Intermediate Similarity	NPC86266
0.8191	Intermediate Similarity	NPC212301
0.8191	Intermediate Similarity	NPC110657
0.8191	Intermediate Similarity	NPC63748
0.8191	Intermediate Similarity	NPC19114
0.8182	Intermediate Similarity	NPC234892
0.8182	Intermediate Similarity	NPC87351
0.8182	Intermediate Similarity	NPC281702
0.8182	Intermediate Similarity	NPC473424
0.8173	Intermediate Similarity	NPC221144
0.8172	Intermediate Similarity	NPC123912
0.8172	Intermediate Similarity	NPC186688
0.8172	Intermediate Similarity	NPC477973
0.8172	Intermediate Similarity	NPC1015
0.8172	Intermediate Similarity	NPC215029
0.8172	Intermediate Similarity	NPC476733
0.8172	Intermediate Similarity	NPC31985
0.8172	Intermediate Similarity	NPC473039
0.8163	Intermediate Similarity	NPC307954
0.8163	Intermediate Similarity	NPC327431
0.8163	Intermediate Similarity	NPC476274
0.8155	Intermediate Similarity	NPC197428
0.8152	Intermediate Similarity	NPC96496
0.8152	Intermediate Similarity	NPC58063
0.8152	Intermediate Similarity	NPC475740
0.8152	Intermediate Similarity	NPC317590

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 NPC25750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1910
0.2-0.3	4122
0.3-0.4	1980
0.4-0.5	517
0.5-0.6	156
0.6-0.7	155
0.7-0.8	133
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8298	Intermediate Similarity	NPD6399	Phase 3
0.8235	Intermediate Similarity	NPD6372	Approved
0.8235	Intermediate Similarity	NPD6373	Approved
0.8222	Intermediate Similarity	NPD3665	Phase 1
0.8222	Intermediate Similarity	NPD3133	Approved
0.8222	Intermediate Similarity	NPD3666	Approved
0.8191	Intermediate Similarity	NPD5281	Approved
0.8191	Intermediate Similarity	NPD5284	Approved
0.8172	Intermediate Similarity	NPD5328	Approved
0.8144	Intermediate Similarity	NPD6083	Phase 2
0.8144	Intermediate Similarity	NPD6084	Phase 2
0.8125	Intermediate Similarity	NPD5695	Phase 3
0.8119	Intermediate Similarity	NPD5739	Approved
0.8119	Intermediate Similarity	NPD6675	Approved
0.8119	Intermediate Similarity	NPD6402	Approved
0.8119	Intermediate Similarity	NPD7128	Approved
0.8077	Intermediate Similarity	NPD6650	Approved
0.8077	Intermediate Similarity	NPD6649	Approved
0.8043	Intermediate Similarity	NPD7146	Approved
0.8043	Intermediate Similarity	NPD5330	Approved
0.8043	Intermediate Similarity	NPD7334	Approved
0.8043	Intermediate Similarity	NPD6684	Approved
0.8043	Intermediate Similarity	NPD7521	Approved
0.8043	Intermediate Similarity	NPD6409	Approved
0.8041	Intermediate Similarity	NPD4697	Phase 3
0.8022	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD6079	Approved
0.7979	Intermediate Similarity	NPD4753	Phase 2
0.7961	Intermediate Similarity	NPD7320	Approved
0.7961	Intermediate Similarity	NPD6899	Approved
0.7961	Intermediate Similarity	NPD6881	Approved
0.7959	Intermediate Similarity	NPD4755	Approved
0.7879	Intermediate Similarity	NPD5696	Approved
0.7872	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6903	Approved
0.7864	Intermediate Similarity	NPD5701	Approved
0.7864	Intermediate Similarity	NPD5697	Approved
0.7849	Intermediate Similarity	NPD5279	Phase 3
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.781	Intermediate Similarity	NPD7102	Approved
0.781	Intermediate Similarity	NPD6883	Approved
0.781	Intermediate Similarity	NPD7290	Approved
0.7802	Intermediate Similarity	NPD3667	Approved
0.7802	Intermediate Similarity	NPD4223	Phase 3
0.7802	Intermediate Similarity	NPD4221	Approved
0.78	Intermediate Similarity	NPD5286	Approved
0.78	Intermediate Similarity	NPD4700	Approved
0.78	Intermediate Similarity	NPD4696	Approved
0.78	Intermediate Similarity	NPD5285	Approved
0.7788	Intermediate Similarity	NPD6011	Approved
0.7755	Intermediate Similarity	NPD5210	Approved
0.7755	Intermediate Similarity	NPD4629	Approved
0.7742	Intermediate Similarity	NPD5329	Approved
0.7736	Intermediate Similarity	NPD6847	Approved
0.7736	Intermediate Similarity	NPD8130	Phase 1
0.7736	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6617	Approved
0.7736	Intermediate Similarity	NPD6869	Approved
0.7732	Intermediate Similarity	NPD4202	Approved
0.7723	Intermediate Similarity	NPD5223	Approved
0.7714	Intermediate Similarity	NPD6012	Approved
0.7714	Intermediate Similarity	NPD6014	Approved
0.7714	Intermediate Similarity	NPD6013	Approved
0.7692	Intermediate Similarity	NPD4692	Approved
0.7692	Intermediate Similarity	NPD4139	Approved
0.7684	Intermediate Similarity	NPD6672	Approved
0.7684	Intermediate Similarity	NPD5737	Approved
0.7677	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5222	Approved
0.7677	Intermediate Similarity	NPD5221	Approved
0.7664	Intermediate Similarity	NPD8297	Approved
0.7664	Intermediate Similarity	NPD6882	Approved
0.766	Intermediate Similarity	NPD5690	Phase 2
0.766	Intermediate Similarity	NPD4694	Approved
0.766	Intermediate Similarity	NPD5280	Approved
0.7647	Intermediate Similarity	NPD4633	Approved
0.7647	Intermediate Similarity	NPD5226	Approved
0.7647	Intermediate Similarity	NPD5224	Approved
0.7647	Intermediate Similarity	NPD5225	Approved
0.7647	Intermediate Similarity	NPD5211	Phase 2
0.7634	Intermediate Similarity	NPD4197	Approved
0.7629	Intermediate Similarity	NPD7515	Phase 2
0.7629	Intermediate Similarity	NPD6050	Approved
0.7604	Intermediate Similarity	NPD6080	Approved
0.7604	Intermediate Similarity	NPD6904	Approved
0.7604	Intermediate Similarity	NPD6673	Approved
0.76	Intermediate Similarity	NPD5173	Approved
0.7596	Intermediate Similarity	NPD6008	Approved
0.7576	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5174	Approved
0.7573	Intermediate Similarity	NPD5175	Approved
0.7573	Intermediate Similarity	NPD4754	Approved
0.7556	Intermediate Similarity	NPD3617	Approved
0.7527	Intermediate Similarity	NPD4788	Approved
0.7526	Intermediate Similarity	NPD5692	Phase 3
0.7526	Intermediate Similarity	NPD5207	Approved
0.75	Intermediate Similarity	NPD5141	Approved
0.7474	Intermediate Similarity	NPD4688	Approved
0.7474	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4693	Phase 3
0.7474	Intermediate Similarity	NPD5205	Approved
0.7474	Intermediate Similarity	NPD4690	Approved
0.7474	Intermediate Similarity	NPD4138	Approved
0.7474	Intermediate Similarity	NPD4689	Approved
0.7449	Intermediate Similarity	NPD5694	Approved
0.7431	Intermediate Similarity	NPD4632	Approved
0.7429	Intermediate Similarity	NPD4768	Approved
0.7429	Intermediate Similarity	NPD4767	Approved
0.7426	Intermediate Similarity	NPD7902	Approved
0.7423	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6335	Approved
0.732	Intermediate Similarity	NPD5208	Approved
0.73	Intermediate Similarity	NPD7748	Approved
0.7297	Intermediate Similarity	NPD6274	Approved
0.7292	Intermediate Similarity	NPD5786	Approved
0.7292	Intermediate Similarity	NPD6098	Approved
0.729	Intermediate Similarity	NPD4729	Approved
0.729	Intermediate Similarity	NPD4730	Approved
0.729	Intermediate Similarity	NPD5128	Approved
0.7273	Intermediate Similarity	NPD5693	Phase 1
0.7273	Intermediate Similarity	NPD8035	Phase 2
0.7273	Intermediate Similarity	NPD6411	Approved
0.7273	Intermediate Similarity	NPD8034	Phase 2
0.7263	Intermediate Similarity	NPD3668	Phase 3
0.7257	Intermediate Similarity	NPD7100	Approved
0.7257	Intermediate Similarity	NPD7101	Approved
0.7232	Intermediate Similarity	NPD6317	Approved
0.7232	Intermediate Similarity	NPD6009	Approved
0.7228	Intermediate Similarity	NPD5654	Approved
0.7204	Intermediate Similarity	NPD4748	Discontinued
0.7204	Intermediate Similarity	NPD5368	Approved
0.72	Intermediate Similarity	NPD5133	Approved
0.7196	Intermediate Similarity	NPD6412	Phase 2
0.7188	Intermediate Similarity	NPD5363	Approved
0.7184	Intermediate Similarity	NPD7638	Approved
0.7182	Intermediate Similarity	NPD6053	Discontinued
0.7172	Intermediate Similarity	NPD5785	Approved
0.7172	Intermediate Similarity	NPD4096	Approved
0.7168	Intermediate Similarity	NPD6313	Approved
0.7168	Intermediate Similarity	NPD6314	Approved
0.7159	Intermediate Similarity	NPD4245	Approved
0.7159	Intermediate Similarity	NPD4244	Approved
0.7156	Intermediate Similarity	NPD5135	Approved
0.7156	Intermediate Similarity	NPD5249	Phase 3
0.7156	Intermediate Similarity	NPD5169	Approved
0.7156	Intermediate Similarity	NPD5251	Approved
0.7156	Intermediate Similarity	NPD5250	Approved
0.7156	Intermediate Similarity	NPD4634	Approved
0.7156	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5248	Approved
0.7156	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD4518	Approved
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6117	Approved
0.7143	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD6908	Approved
0.713	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6909	Approved
0.7129	Intermediate Similarity	NPD6001	Approved
0.7129	Intermediate Similarity	NPD7900	Approved
0.7129	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5369	Approved
0.7115	Intermediate Similarity	NPD7640	Approved
0.7115	Intermediate Similarity	NPD7639	Approved
0.7111	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4195	Approved
0.7091	Intermediate Similarity	NPD5215	Approved
0.7091	Intermediate Similarity	NPD5217	Approved
0.7091	Intermediate Similarity	NPD5127	Approved
0.7091	Intermediate Similarity	NPD5216	Approved
0.7087	Intermediate Similarity	NPD5959	Approved
0.708	Intermediate Similarity	NPD7115	Discovery
0.7071	Intermediate Similarity	NPD6101	Approved
0.7071	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6116	Phase 1
0.7053	Intermediate Similarity	NPD6435	Approved
0.7053	Intermediate Similarity	NPD4269	Approved
0.7053	Intermediate Similarity	NPD4270	Approved
0.7045	Intermediate Similarity	NPD3698	Phase 2
0.7043	Intermediate Similarity	NPD6319	Approved
0.7033	Intermediate Similarity	NPD6942	Approved
0.7033	Intermediate Similarity	NPD3702	Approved
0.7033	Intermediate Similarity	NPD7339	Approved
0.7021	Intermediate Similarity	NPD4695	Discontinued
0.7009	Intermediate Similarity	NPD7604	Phase 2
0.699	Remote Similarity	NPD7614	Phase 1
0.6989	Remote Similarity	NPD6115	Approved
0.6989	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6114	Approved
0.6989	Remote Similarity	NPD6118	Approved
0.6989	Remote Similarity	NPD6697	Approved
0.6983	Remote Similarity	NPD5983	Phase 2
0.6981	Remote Similarity	NPD7632	Discontinued
0.6979	Remote Similarity	NPD5362	Discontinued
0.6972	Remote Similarity	NPD5168	Approved
0.6949	Remote Similarity	NPD7492	Approved
0.6923	Remote Similarity	NPD5733	Approved
0.6916	Remote Similarity	NPD6052	Approved
0.6903	Remote Similarity	NPD5167	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