NPASS Compound

Structure

CID3772 OpenBabel06191715322D 34 37 0 0 1 0 0 0 0 0999 V2000 -1.8162 2.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3725 -2.9548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2459 -2.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5291 0.5228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2757 4.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3578 3.2741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 4.1162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2143 -0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3717 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6867 -1.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8427 1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8435 1.4594 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8435 -1.4599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6859 0.9733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5296 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2146 -1.4590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6850 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8167 4.1159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6861 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3723 -1.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5294 -0.4860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9729 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 -0.0224 -1.9602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5518 1.4736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0808 -1.9586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3919 -0.7078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3027 3.2736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3032 4.9579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 7 34 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 27 1 0 0 0 0 15 1 1 6 0 0 0 15 16 1 0 0 0 0 16 27 1 6 0 0 0 17 24 1 0 0 0 0 17 29 1 6 0 0 0 18 23 1 0 0 0 0 18 30 2 0 0 0 0 19 25 1 0 0 0 0 19 26 1 6 0 0 0 20 25 1 0 0 0 0 20 31 2 0 0 0 0 21 28 1 0 0 0 0 21 32 2 0 0 0 0 22 33 2 0 0 0 0 22 34 1 0 0 0 0 23 24 2 0 0 0 0 23 26 1 0 0 0 0 24 28 1 0 0 0 0 26 4 1 6 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.28
Volume:	498.177
LogP:	3.385
LogD:	3.437
LogS:	-4.194
# Rotatable Bonds:	5
TPSA:	94.58
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	4.865
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.281
MDCK Permeability:	2.7384827262721956e-05
Pgp-inhibitor:	0.947
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.928
Plasma Protein Binding (PPB):	68.79523468017578%
Volume Distribution (VD):	0.404
Pgp-substrate:	24.012378692626953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.498
CYP2C19-inhibitor:	0.199
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.163
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.828

ADMET: Excretion

Clearance (CL):	10.645
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.703
Maximum Recommended Daily Dose:	0.212
Skin Sensitization:	0.027
Carcinogencity:	0.12
Eye Corrosion:	0.197
Eye Irritation:	0.062
Respiratory Toxicity:	0.817

Download Data

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

Natural Product: NPC3772

Natural Product ID:	NPC3772
*Common Name:**	Methyl Lucidenate A
IUPAC Name:	methyl (4R)-4-[(5R,7S,10S,13R,14R,17R)-7-hydroxy-4,4,10,13,14-pentamethyl-3,11,15-trioxo-1,2,5,6,7,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]pentanoate
Synonyms:
Standard InCHIKey:	AVSUQFFHBSVWRI-NZXXOGSYSA-N
Standard InCHI:	InChI=1S/C28H40O6/c1-15(8-9-22(33)34-7)16-12-21(32)28(6)24-17(29)13-19-25(2,3)20(31)10-11-26(19,4)23(24)18(30)14-27(16,28)5/h15-17,19,29H,8-14H2,1-7H3/t15-,16-,17+,19+,26+,27-,28+/m1/s1
SMILES:	COC(=O)CC[C@H]([C@H]1CC(=O)[C@@]2([C@]1(C)CC(=O)C1=C2[C@@H](O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460970
PubChem CID:	21636089
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	1
Others	6

Activity Type	# Activity
Cell Line	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[495417]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	22.0	%	PMID[495418]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[495417]
NPT2	Others	Unspecified		Activity	=	24.9	%	PMID[495417]
NPT2	Others	Unspecified		Activity	=	75.1	%	PMID[495417]
NPT2	Others	Unspecified		Activity	=	95.0	%	PMID[495417]
NPT2	Others	Unspecified		IC50	=	287.0	molar ratio	PMID[495417]

☑ 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 NPC3772 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	186
0.1-0.2	1312
0.2-0.3	5432
0.3-0.4	12621
0.4-0.5	9485
0.5-0.6	6788
0.6-0.7	5257
0.7-0.8	1360
0.8-0.85	136
0.85-0.9	84
0.9-0.95	27
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9889	High Similarity	NPC121339
0.9889	High Similarity	NPC106557
0.9888	High Similarity	NPC37646
0.9778	High Similarity	NPC243525
0.9778	High Similarity	NPC40765
0.9556	High Similarity	NPC184870
0.9462	High Similarity	NPC51370
0.9462	High Similarity	NPC287833
0.9444	High Similarity	NPC470254
0.9348	High Similarity	NPC328371
0.9333	High Similarity	NPC107690
0.9255	High Similarity	NPC144660
0.9255	High Similarity	NPC205899
0.9255	High Similarity	NPC307954
0.9255	High Similarity	NPC299971
0.9247	High Similarity	NPC122294
0.9247	High Similarity	NPC18319
0.9239	High Similarity	NPC255809
0.9239	High Similarity	NPC173875
0.9239	High Similarity	NPC469995
0.9239	High Similarity	NPC318282
0.9239	High Similarity	NPC174948
0.9167	High Similarity	NPC251017
0.9149	High Similarity	NPC16021
0.9149	High Similarity	NPC10364
0.914	High Similarity	NPC456
0.914	High Similarity	NPC125622
0.914	High Similarity	NPC472941
0.9082	High Similarity	NPC473037
0.9062	High Similarity	NPC56498
0.9062	High Similarity	NPC281702
0.9053	High Similarity	NPC88198
0.9032	High Similarity	NPC241156
0.9011	High Similarity	NPC477149
0.9011	High Similarity	NPC477147
0.898	High Similarity	NPC51452
0.8969	High Similarity	NPC236390
0.8936	High Similarity	NPC7124
0.8901	High Similarity	NPC214387
0.89	High Similarity	NPC77947
0.89	High Similarity	NPC286174
0.8878	High Similarity	NPC28656
0.8866	High Similarity	NPC293753
0.8866	High Similarity	NPC119601
0.8866	High Similarity	NPC234892
0.8866	High Similarity	NPC308726
0.8866	High Similarity	NPC195290
0.8866	High Similarity	NPC204450
0.8854	High Similarity	NPC157787
0.883	High Similarity	NPC297199
0.883	High Similarity	NPC470016
0.883	High Similarity	NPC317586
0.8817	High Similarity	NPC25750
0.8817	High Similarity	NPC472930
0.8812	High Similarity	NPC473036
0.8812	High Similarity	NPC129689
0.8812	High Similarity	NPC272898
0.88	High Similarity	NPC295244
0.8776	High Similarity	NPC70967
0.8776	High Similarity	NPC33973
0.8776	High Similarity	NPC55872
0.8763	High Similarity	NPC472924
0.8763	High Similarity	NPC163372
0.8763	High Similarity	NPC302537
0.875	High Similarity	NPC197386
0.875	High Similarity	NPC471717
0.8737	High Similarity	NPC95565
0.8725	High Similarity	NPC115303
0.8723	High Similarity	NPC166906
0.871	High Similarity	NPC63748
0.8687	High Similarity	NPC2436
0.8687	High Similarity	NPC135854
0.8687	High Similarity	NPC216245
0.8687	High Similarity	NPC470251
0.8667	High Similarity	NPC473038
0.866	High Similarity	NPC476274
0.8646	High Similarity	NPC320306
0.8646	High Similarity	NPC43747
0.8617	High Similarity	NPC69454
0.8571	High Similarity	NPC476240
0.8571	High Similarity	NPC224720
0.8571	High Similarity	NPC124211
0.8571	High Similarity	NPC476223
0.8556	High Similarity	NPC209882
0.8544	High Similarity	NPC472928
0.8542	High Similarity	NPC328162
0.8542	High Similarity	NPC305483
0.8542	High Similarity	NPC249954
0.8542	High Similarity	NPC96859
0.8485	Intermediate Similarity	NPC53222
0.8485	Intermediate Similarity	NPC136289
0.8478	Intermediate Similarity	NPC99909
0.8469	Intermediate Similarity	NPC327431
0.8469	Intermediate Similarity	NPC316964
0.8469	Intermediate Similarity	NPC198880
0.8444	Intermediate Similarity	NPC271784
0.8444	Intermediate Similarity	NPC469561
0.8438	Intermediate Similarity	NPC259286
0.8438	Intermediate Similarity	NPC472932
0.8421	Intermediate Similarity	NPC243866
0.8416	Intermediate Similarity	NPC323834
0.8404	Intermediate Similarity	NPC289213
0.8404	Intermediate Similarity	NPC469400
0.8404	Intermediate Similarity	NPC20388
0.8387	Intermediate Similarity	NPC131470
0.8387	Intermediate Similarity	NPC143767
0.8384	Intermediate Similarity	NPC81530
0.8381	Intermediate Similarity	NPC472929
0.837	Intermediate Similarity	NPC322159
0.8367	Intermediate Similarity	NPC166745
0.8367	Intermediate Similarity	NPC235464
0.8333	Intermediate Similarity	NPC472925
0.8333	Intermediate Similarity	NPC471720
0.8333	Intermediate Similarity	NPC469406
0.8318	Intermediate Similarity	NPC472927
0.8316	Intermediate Similarity	NPC297265
0.8316	Intermediate Similarity	NPC233116
0.8298	Intermediate Similarity	NPC275740
0.8298	Intermediate Similarity	NPC54689
0.8298	Intermediate Similarity	NPC123912
0.8298	Intermediate Similarity	NPC473039
0.8298	Intermediate Similarity	NPC86319
0.8286	Intermediate Similarity	NPC285956
0.8283	Intermediate Similarity	NPC218383
0.8269	Intermediate Similarity	NPC37116
0.8269	Intermediate Similarity	NPC470496
0.8265	Intermediate Similarity	NPC216904
0.8265	Intermediate Similarity	NPC475894
0.8265	Intermediate Similarity	NPC253826
0.8265	Intermediate Similarity	NPC23680
0.8265	Intermediate Similarity	NPC107243
0.8261	Intermediate Similarity	NPC123319
0.8261	Intermediate Similarity	NPC474083
0.8261	Intermediate Similarity	NPC311702
0.8261	Intermediate Similarity	NPC94531
0.8247	Intermediate Similarity	NPC476174
0.8229	Intermediate Similarity	NPC206810
0.8211	Intermediate Similarity	NPC48010
0.8211	Intermediate Similarity	NPC183283
0.82	Intermediate Similarity	NPC99411
0.8191	Intermediate Similarity	NPC476796
0.8191	Intermediate Similarity	NPC242864
0.8182	Intermediate Similarity	NPC275439
0.8182	Intermediate Similarity	NPC48647
0.8182	Intermediate Similarity	NPC112753
0.8182	Intermediate Similarity	NPC478056
0.8172	Intermediate Similarity	NPC55309
0.8172	Intermediate Similarity	NPC72133
0.8172	Intermediate Similarity	NPC28252
0.8165	Intermediate Similarity	NPC472933
0.8163	Intermediate Similarity	NPC155676
0.8155	Intermediate Similarity	NPC185
0.8155	Intermediate Similarity	NPC91034
0.8152	Intermediate Similarity	NPC473246
0.8152	Intermediate Similarity	NPC109512
0.8152	Intermediate Similarity	NPC320801
0.8152	Intermediate Similarity	NPC165064
0.8148	Intermediate Similarity	NPC472934
0.8144	Intermediate Similarity	NPC318332
0.8125	Intermediate Similarity	NPC23434
0.8125	Intermediate Similarity	NPC150383
0.8125	Intermediate Similarity	NPC473998
0.8125	Intermediate Similarity	NPC154101
0.8119	Intermediate Similarity	NPC477915
0.8119	Intermediate Similarity	NPC473424
0.8113	Intermediate Similarity	NPC264634
0.8113	Intermediate Similarity	NPC147180
0.8105	Intermediate Similarity	NPC309603
0.8105	Intermediate Similarity	NPC155479
0.8105	Intermediate Similarity	NPC477943
0.8105	Intermediate Similarity	NPC473999
0.8105	Intermediate Similarity	NPC474889
0.81	Intermediate Similarity	NPC477521
0.8085	Intermediate Similarity	NPC159046
0.8085	Intermediate Similarity	NPC233836
0.8085	Intermediate Similarity	NPC136948
0.8085	Intermediate Similarity	NPC187376
0.8081	Intermediate Similarity	NPC57416
0.8065	Intermediate Similarity	NPC11711
0.8065	Intermediate Similarity	NPC471224
0.8065	Intermediate Similarity	NPC8571
0.8065	Intermediate Similarity	NPC472940
0.8065	Intermediate Similarity	NPC472931
0.8061	Intermediate Similarity	NPC48330
0.8061	Intermediate Similarity	NPC271195
0.8061	Intermediate Similarity	NPC473648
0.8061	Intermediate Similarity	NPC184848
0.8061	Intermediate Similarity	NPC469599
0.8061	Intermediate Similarity	NPC200702
0.8061	Intermediate Similarity	NPC69548
0.8058	Intermediate Similarity	NPC472935
0.8043	Intermediate Similarity	NPC41539
0.8043	Intermediate Similarity	NPC168188
0.8043	Intermediate Similarity	NPC470015
0.8041	Intermediate Similarity	NPC107674
0.8041	Intermediate Similarity	NPC170220
0.8041	Intermediate Similarity	NPC152897
0.8041	Intermediate Similarity	NPC66429
0.8041	Intermediate Similarity	NPC141497
0.8041	Intermediate Similarity	NPC214697

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 NPC3772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1727
0.2-0.3	4019
0.3-0.4	2215
0.4-0.5	566
0.5-0.6	183
0.6-0.7	178
0.7-0.8	100
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8105	Intermediate Similarity	NPD5328	Approved
0.7938	Intermediate Similarity	NPD6079	Approved
0.7885	Intermediate Similarity	NPD6402	Approved
0.7885	Intermediate Similarity	NPD5739	Approved
0.7885	Intermediate Similarity	NPD7128	Approved
0.7885	Intermediate Similarity	NPD6675	Approved
0.7857	Intermediate Similarity	NPD6399	Phase 3
0.783	Intermediate Similarity	NPD6373	Approved
0.783	Intermediate Similarity	NPD6372	Approved
0.7822	Intermediate Similarity	NPD5696	Approved
0.78	Intermediate Similarity	NPD4697	Phase 3
0.7789	Intermediate Similarity	NPD3618	Phase 1
0.7736	Intermediate Similarity	NPD6899	Approved
0.7736	Intermediate Similarity	NPD6881	Approved
0.7736	Intermediate Similarity	NPD7320	Approved
0.7723	Intermediate Similarity	NPD6083	Phase 2
0.7723	Intermediate Similarity	NPD6084	Phase 2
0.77	Intermediate Similarity	NPD5695	Phase 3
0.7685	Intermediate Similarity	NPD6649	Approved
0.7685	Intermediate Similarity	NPD6650	Approved
0.7642	Intermediate Similarity	NPD5697	Approved
0.7642	Intermediate Similarity	NPD5701	Approved
0.7629	Intermediate Similarity	NPD6672	Approved
0.7629	Intermediate Similarity	NPD5737	Approved
0.7624	Intermediate Similarity	NPD5221	Approved
0.7624	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5222	Approved
0.7604	Intermediate Similarity	NPD6409	Approved
0.7604	Intermediate Similarity	NPD5330	Approved
0.7604	Intermediate Similarity	NPD7521	Approved
0.7604	Intermediate Similarity	NPD7334	Approved
0.7604	Intermediate Similarity	NPD6684	Approved
0.7604	Intermediate Similarity	NPD5279	Phase 3
0.7604	Intermediate Similarity	NPD7146	Approved
0.7596	Intermediate Similarity	NPD5211	Phase 2
0.7593	Intermediate Similarity	NPD7290	Approved
0.7593	Intermediate Similarity	NPD7102	Approved
0.7593	Intermediate Similarity	NPD6883	Approved
0.7579	Intermediate Similarity	NPD3666	Approved
0.7579	Intermediate Similarity	NPD3133	Approved
0.7579	Intermediate Similarity	NPD3665	Phase 1
0.7579	Intermediate Similarity	NPD4786	Approved
0.7576	Intermediate Similarity	NPD5281	Approved
0.7576	Intermediate Similarity	NPD7515	Phase 2
0.7576	Intermediate Similarity	NPD5284	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD6011	Approved
0.7549	Intermediate Similarity	NPD5173	Approved
0.7549	Intermediate Similarity	NPD4755	Approved
0.7525	Intermediate Similarity	NPD5210	Approved
0.7525	Intermediate Similarity	NPD4629	Approved
0.7523	Intermediate Similarity	NPD8130	Phase 1
0.7523	Intermediate Similarity	NPD6617	Approved
0.7523	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6869	Approved
0.7523	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7476	Intermediate Similarity	NPD7638	Approved
0.7455	Intermediate Similarity	NPD8297	Approved
0.7455	Intermediate Similarity	NPD6882	Approved
0.7453	Intermediate Similarity	NPD5141	Approved
0.7449	Intermediate Similarity	NPD6903	Approved
0.7449	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7632	Discontinued
0.7426	Intermediate Similarity	NPD7748	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4700	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.7379	Intermediate Similarity	NPD7902	Approved
0.7374	Intermediate Similarity	NPD4753	Phase 2
0.7368	Intermediate Similarity	NPD3667	Approved
0.7353	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5223	Approved
0.7327	Intermediate Similarity	NPD4202	Approved
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3617	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7257	Intermediate Similarity	NPD6868	Approved
0.7245	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4632	Approved
0.7228	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD6050	Approved
0.7228	Intermediate Similarity	NPD8035	Phase 2
0.7222	Intermediate Similarity	NPD6008	Approved
0.72	Intermediate Similarity	NPD6904	Approved
0.72	Intermediate Similarity	NPD6080	Approved
0.72	Intermediate Similarity	NPD6673	Approved
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7196	Intermediate Similarity	NPD4754	Approved
0.7188	Intermediate Similarity	NPD4223	Phase 3
0.7188	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD5329	Approved
0.713	Intermediate Similarity	NPD6335	Approved
0.7129	Intermediate Similarity	NPD5785	Approved
0.7129	Intermediate Similarity	NPD5207	Approved
0.7129	Intermediate Similarity	NPD5692	Phase 3
0.7115	Intermediate Similarity	NPD7614	Phase 1
0.7105	Intermediate Similarity	NPD6274	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7087	Intermediate Similarity	NPD7900	Approved
0.7087	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4139	Approved
0.7083	Intermediate Similarity	NPD4692	Approved
0.7075	Intermediate Similarity	NPD6404	Discontinued
0.7071	Intermediate Similarity	NPD5690	Phase 2
0.7071	Intermediate Similarity	NPD5786	Approved
0.7071	Intermediate Similarity	NPD5280	Approved
0.7071	Intermediate Similarity	NPD4694	Approved
0.7069	Intermediate Similarity	NPD7100	Approved
0.7069	Intermediate Similarity	NPD7101	Approved
0.7064	Intermediate Similarity	NPD4767	Approved
0.7064	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD6411	Approved
0.7059	Intermediate Similarity	NPD5694	Approved
0.7043	Intermediate Similarity	NPD6009	Approved
0.7043	Intermediate Similarity	NPD6317	Approved
0.7041	Intermediate Similarity	NPD4197	Approved
0.7033	Intermediate Similarity	NPD6081	Approved
0.703	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6116	Phase 1
0.6991	Remote Similarity	NPD6053	Discontinued
0.699	Remote Similarity	NPD5779	Approved
0.699	Remote Similarity	NPD5778	Approved
0.6983	Remote Similarity	NPD6313	Approved
0.6983	Remote Similarity	NPD6314	Approved
0.697	Remote Similarity	NPD5363	Approved
0.6952	Remote Similarity	NPD7732	Phase 3
0.6949	Remote Similarity	NPD6908	Approved
0.6949	Remote Similarity	NPD6909	Approved
0.6949	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6939	Remote Similarity	NPD5362	Discontinued
0.6939	Remote Similarity	NPD4788	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6937	Remote Similarity	NPD5168	Approved
0.6931	Remote Similarity	NPD5208	Approved
0.6923	Remote Similarity	NPD6001	Approved
0.69	Remote Similarity	NPD4138	Approved
0.69	Remote Similarity	NPD4689	Approved
0.69	Remote Similarity	NPD4623	Approved
0.69	Remote Similarity	NPD4519	Discontinued
0.69	Remote Similarity	NPD4693	Phase 3
0.69	Remote Similarity	NPD5205	Approved
0.69	Remote Similarity	NPD6098	Approved
0.69	Remote Similarity	NPD4688	Approved
0.69	Remote Similarity	NPD4690	Approved
0.6882	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3668	Phase 3
0.6864	Remote Similarity	NPD6319	Approved
0.6863	Remote Similarity	NPD6101	Approved
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5654	Approved
0.6855	Remote Similarity	NPD7260	Phase 2
0.6847	Remote Similarity	NPD6412	Phase 2
0.6837	Remote Similarity	NPD4269	Approved
0.6837	Remote Similarity	NPD4270	Approved
0.6837	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7604	Phase 2
0.6832	Remote Similarity	NPD3573	Approved
0.6822	Remote Similarity	NPD4225	Approved
0.6814	Remote Similarity	NPD5251	Approved
0.6814	Remote Similarity	NPD5250	Approved
0.6814	Remote Similarity	NPD5248	Approved
0.6814	Remote Similarity	NPD4634	Approved
0.6814	Remote Similarity	NPD5247	Approved
0.6814	Remote Similarity	NPD5135	Approved
0.6814	Remote Similarity	NPD5249	Phase 3
0.6814	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5169	Approved
0.6814	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5983	Phase 2
0.68	Remote Similarity	NPD6845	Suspended
0.6777	Remote Similarity	NPD7492	Approved
0.6754	Remote Similarity	NPD5217	Approved
0.6754	Remote Similarity	NPD5216	Approved
0.6754	Remote Similarity	NPD5127	Approved
0.6754	Remote Similarity	NPD5215	Approved
0.6731	Remote Similarity	NPD7637	Suspended
0.6729	Remote Similarity	NPD5959	Approved
0.6726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6054	Approved
0.6723	Remote Similarity	NPD6059	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