NPASS Compound

Structure

CID236390 OpenBabel06191716032D 38 41 0 0 1 0 0 0 0 0999 V2000 -1.8217 2.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2854 4.9725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3826 -2.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2586 -2.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5366 0.5244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3598 6.6627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2269 -0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3818 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3588 3.2839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8221 4.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6903 0.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 -1.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 2.4391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3101 4.9727 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8468 4.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 1.4637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8460 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6909 0.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5372 -1.4638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2272 -1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6912 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 -0.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8226 5.8176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3823 -1.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5369 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9758 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 -0.3593 4.9733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0199 -1.9646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 1.4765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0934 -1.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3969 -0.7078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3105 6.6621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 5.8179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 38 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 29 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 17 27 1 0 0 0 0 18 32 2 0 0 0 0 19 30 1 6 0 0 0 20 26 1 0 0 0 0 20 33 1 6 0 0 0 21 25 1 0 0 0 0 21 34 2 0 0 0 0 22 28 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 0 0 0 0 23 35 2 0 0 0 0 24 31 1 1 0 0 0 24 36 1 0 0 0 0 25 26 2 0 0 0 0 25 29 1 0 0 0 0 26 31 1 0 0 0 0 27 37 2 0 0 0 0 27 38 1 0 0 0 0 29 5 1 6 0 0 0 30 31 1 6 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.31
Volume:	556.219
LogP:	3.056
LogD:	2.612
LogS:	-4.188
# Rotatable Bonds:	6
TPSA:	114.81
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	5.228
Fsp3:	0.774
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:	-5.239
MDCK Permeability:	2.3080818209564313e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	77.48585510253906%
Volume Distribution (VD):	0.4
Pgp-substrate:	17.045467376708984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.639
CYP2C19-inhibitor:	0.223
CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.379
CYP2C9-substrate:	0.142
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.725

ADMET: Excretion

Clearance (CL):	9.397
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.609
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.113
Carcinogencity:	0.372
Eye Corrosion:	0.012
Eye Irritation:	0.013
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC236390

Natural Product ID:	NPC236390
*Common Name:**	Methyl Ganoderenate A
IUPAC Name:	methyl (E)-6-[(5R,7S,10S,13R,14R,15S,17R)-7,15-dihydroxy-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-oxohept-5-enoate
Synonyms:	Methyl Ganoderenate A
Standard InCHIKey:	VLILOXNRSPUUFE-KZEAGTKASA-N
Standard InCHI:	InChI=1S/C31H44O7/c1-16(11-18(32)12-17(2)27(37)38-8)19-13-24(36)31(7)26-20(33)14-22-28(3,4)23(35)9-10-29(22,5)25(26)21(34)15-30(19,31)6/h11,17,19-20,22,24,33,36H,9-10,12-15H2,1-8H3/b16-11+/t17?,19-,20+,22+,24+,29+,30-,31+/m1/s1
SMILES:	C/C(=CC(=O)CC(C)C(=O)OC)/[C@H]1C[C@@H]([C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1C[C@@H]3O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1922173
PubChem CID:	57395022
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]
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	>	183900.0	nM	PMID[458373]
NPT2	Others	Unspecified		IC50	>	600000.0	nM	PMID[458374]

☑ 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 NPC236390 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	180
0.1-0.2	1077
0.2-0.3	4420
0.3-0.4	10466
0.4-0.5	11443
0.5-0.6	6751
0.6-0.7	5966
0.7-0.8	1997
0.8-0.85	270
0.85-0.9	90
0.9-0.95	32
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC195290
0.9895	High Similarity	NPC204450
0.9684	High Similarity	NPC205899
0.9579	High Similarity	NPC10364
0.9485	High Similarity	NPC56498
0.9474	High Similarity	NPC18319
0.9375	High Similarity	NPC197386
0.9368	High Similarity	NPC328371
0.9293	High Similarity	NPC28656
0.9278	High Similarity	NPC51370
0.9263	High Similarity	NPC173875
0.9263	High Similarity	NPC469995
0.9263	High Similarity	NPC174948
0.9263	High Similarity	NPC318282
0.9192	High Similarity	NPC55872
0.9091	High Similarity	NPC119601
0.9091	High Similarity	NPC308726
0.9082	High Similarity	NPC287833
0.9072	High Similarity	NPC106557
0.9062	High Similarity	NPC472932
0.9053	High Similarity	NPC470254
0.9053	High Similarity	NPC25750
0.899	High Similarity	NPC302537
0.899	High Similarity	NPC163372
0.898	High Similarity	NPC166745
0.898	High Similarity	NPC235464
0.898	High Similarity	NPC471717
0.8969	High Similarity	NPC95565
0.8969	High Similarity	NPC125622
0.8969	High Similarity	NPC243525
0.8969	High Similarity	NPC3772
0.8969	High Similarity	NPC40765
0.8958	High Similarity	NPC184870
0.8947	High Similarity	NPC107690
0.89	High Similarity	NPC136289
0.8889	High Similarity	NPC218383
0.8889	High Similarity	NPC476274
0.8878	High Similarity	NPC121339
0.8878	High Similarity	NPC107243
0.8866	High Similarity	NPC317586
0.8866	High Similarity	NPC241156
0.8866	High Similarity	NPC37646
0.8866	High Similarity	NPC470016
0.8854	High Similarity	NPC243866
0.8854	High Similarity	NPC472930
0.8842	High Similarity	NPC477149
0.8842	High Similarity	NPC477147
0.8835	High Similarity	NPC295244
0.88	High Similarity	NPC476240
0.88	High Similarity	NPC224720
0.88	High Similarity	NPC476223
0.88	High Similarity	NPC472924
0.88	High Similarity	NPC81530
0.88	High Similarity	NPC99411
0.8788	High Similarity	NPC48647
0.8776	High Similarity	NPC472941
0.8776	High Similarity	NPC456
0.8776	High Similarity	NPC155676
0.8763	High Similarity	NPC166906
0.875	High Similarity	NPC154101
0.8737	High Similarity	NPC214387
0.8737	High Similarity	NPC54689
0.8713	High Similarity	NPC234892
0.8713	High Similarity	NPC473424
0.8687	High Similarity	NPC320306
0.8687	High Similarity	NPC475894
0.8687	High Similarity	NPC57416
0.8673	High Similarity	NPC469599
0.866	High Similarity	NPC66429
0.866	High Similarity	NPC206810
0.866	High Similarity	NPC69454
0.866	High Similarity	NPC152897
0.8641	High Similarity	NPC323834
0.8632	High Similarity	NPC294480
0.8627	High Similarity	NPC111323
0.8614	High Similarity	NPC474327
0.86	High Similarity	NPC176845
0.86	High Similarity	NPC186810
0.8598	High Similarity	NPC962
0.8598	High Similarity	NPC250109
0.8586	High Similarity	NPC96859
0.8586	High Similarity	NPC328162
0.8586	High Similarity	NPC173272
0.8586	High Similarity	NPC249954
0.8586	High Similarity	NPC305483
0.8558	High Similarity	NPC220229
0.8558	High Similarity	NPC472925
0.8558	High Similarity	NPC475060
0.8557	High Similarity	NPC63748
0.8557	High Similarity	NPC23434
0.8557	High Similarity	NPC297265
0.8544	High Similarity	NPC235889
0.8542	High Similarity	NPC155479
0.8542	High Similarity	NPC123912
0.8542	High Similarity	NPC477943
0.8529	High Similarity	NPC293753
0.8529	High Similarity	NPC87351
0.8529	High Similarity	NPC477915
0.8526	High Similarity	NPC312215
0.8515	High Similarity	NPC88198
0.8515	High Similarity	NPC154072
0.8515	High Similarity	NPC144660
0.8515	High Similarity	NPC299971
0.8515	High Similarity	NPC327431
0.8515	High Similarity	NPC316964
0.8505	High Similarity	NPC221144
0.8491	Intermediate Similarity	NPC197428
0.8491	Intermediate Similarity	NPC37116
0.8485	Intermediate Similarity	NPC45324
0.8485	Intermediate Similarity	NPC255809
0.8485	Intermediate Similarity	NPC48330
0.8485	Intermediate Similarity	NPC162001
0.8485	Intermediate Similarity	NPC263347
0.8485	Intermediate Similarity	NPC222845
0.8485	Intermediate Similarity	NPC184848
0.8485	Intermediate Similarity	NPC259286
0.8485	Intermediate Similarity	NPC69548
0.8476	Intermediate Similarity	NPC65941
0.8476	Intermediate Similarity	NPC217201
0.8469	Intermediate Similarity	NPC470376
0.8469	Intermediate Similarity	NPC472942
0.8469	Intermediate Similarity	NPC470375
0.8462	Intermediate Similarity	NPC51452
0.8462	Intermediate Similarity	NPC48733
0.8462	Intermediate Similarity	NPC202167
0.8462	Intermediate Similarity	NPC60681
0.8462	Intermediate Similarity	NPC149047
0.8462	Intermediate Similarity	NPC97202
0.8462	Intermediate Similarity	NPC181265
0.8462	Intermediate Similarity	NPC171137
0.8462	Intermediate Similarity	NPC152695
0.8462	Intermediate Similarity	NPC296945
0.8462	Intermediate Similarity	NPC260268
0.8462	Intermediate Similarity	NPC476027
0.8462	Intermediate Similarity	NPC85829
0.8462	Intermediate Similarity	NPC302607
0.8462	Intermediate Similarity	NPC319077
0.8462	Intermediate Similarity	NPC50692
0.8462	Intermediate Similarity	NPC214264
0.8462	Intermediate Similarity	NPC150531
0.8462	Intermediate Similarity	NPC49958
0.8454	Intermediate Similarity	NPC48010
0.8454	Intermediate Similarity	NPC69622
0.8447	Intermediate Similarity	NPC140723
0.8447	Intermediate Similarity	NPC251017
0.8447	Intermediate Similarity	NPC311612
0.844	Intermediate Similarity	NPC266728
0.844	Intermediate Similarity	NPC49492
0.8438	Intermediate Similarity	NPC183546
0.8426	Intermediate Similarity	NPC472929
0.8421	Intermediate Similarity	NPC212843
0.8416	Intermediate Similarity	NPC16021
0.8416	Intermediate Similarity	NPC477813
0.8416	Intermediate Similarity	NPC478056
0.8411	Intermediate Similarity	NPC472928
0.84	Intermediate Similarity	NPC7124
0.84	Intermediate Similarity	NPC42042
0.8396	Intermediate Similarity	NPC258543
0.8396	Intermediate Similarity	NPC241927
0.8396	Intermediate Similarity	NPC11710
0.8384	Intermediate Similarity	NPC7165
0.8384	Intermediate Similarity	NPC469406
0.8381	Intermediate Similarity	NPC83744
0.8381	Intermediate Similarity	NPC185
0.8381	Intermediate Similarity	NPC220974
0.8381	Intermediate Similarity	NPC91034
0.8381	Intermediate Similarity	NPC473037
0.8378	Intermediate Similarity	NPC475041
0.8367	Intermediate Similarity	NPC45269
0.8365	Intermediate Similarity	NPC209502
0.8365	Intermediate Similarity	NPC96268
0.8365	Intermediate Similarity	NPC119493
0.8365	Intermediate Similarity	NPC477812
0.8365	Intermediate Similarity	NPC204833
0.8364	Intermediate Similarity	NPC471854
0.8351	Intermediate Similarity	NPC86319
0.8351	Intermediate Similarity	NPC275740
0.835	Intermediate Similarity	NPC281702
0.8333	Intermediate Similarity	NPC71348
0.8333	Intermediate Similarity	NPC241221
0.8333	Intermediate Similarity	NPC307954
0.8333	Intermediate Similarity	NPC100267
0.8333	Intermediate Similarity	NPC475524
0.8333	Intermediate Similarity	NPC157787
0.8318	Intermediate Similarity	NPC473036
0.8318	Intermediate Similarity	NPC272898
0.8317	Intermediate Similarity	NPC122294
0.8317	Intermediate Similarity	NPC469432
0.8317	Intermediate Similarity	NPC69385
0.8317	Intermediate Similarity	NPC23680
0.8317	Intermediate Similarity	NPC253826
0.8317	Intermediate Similarity	NPC43747
0.8316	Intermediate Similarity	NPC474083
0.8302	Intermediate Similarity	NPC329417
0.83	Intermediate Similarity	NPC476174
0.8286	Intermediate Similarity	NPC231530
0.8286	Intermediate Similarity	NPC278628
0.8283	Intermediate Similarity	NPC170220
0.8283	Intermediate Similarity	NPC476416
0.8283	Intermediate Similarity	NPC141497

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 NPC236390 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1407
0.2-0.3	3797
0.3-0.4	2530
0.4-0.5	745
0.5-0.6	201
0.6-0.7	153
0.7-0.8	156
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD6373	Approved
0.8571	High Similarity	NPD6372	Approved
0.8469	Intermediate Similarity	NPD6399	Phase 3
0.8462	Intermediate Similarity	NPD7128	Approved
0.8462	Intermediate Similarity	NPD6402	Approved
0.8462	Intermediate Similarity	NPD5739	Approved
0.8462	Intermediate Similarity	NPD6675	Approved
0.8411	Intermediate Similarity	NPD6649	Approved
0.8411	Intermediate Similarity	NPD6650	Approved
0.8302	Intermediate Similarity	NPD7320	Approved
0.8302	Intermediate Similarity	NPD6899	Approved
0.8302	Intermediate Similarity	NPD6881	Approved
0.8208	Intermediate Similarity	NPD5697	Approved
0.8208	Intermediate Similarity	NPD5701	Approved
0.8182	Intermediate Similarity	NPD5284	Approved
0.8182	Intermediate Similarity	NPD5281	Approved
0.8173	Intermediate Similarity	NPD5211	Phase 2
0.8163	Intermediate Similarity	NPD5328	Approved
0.8148	Intermediate Similarity	NPD6883	Approved
0.8148	Intermediate Similarity	NPD7102	Approved
0.8148	Intermediate Similarity	NPD7290	Approved
0.8137	Intermediate Similarity	NPD6083	Phase 2
0.8137	Intermediate Similarity	NPD4755	Approved
0.8137	Intermediate Similarity	NPD6084	Phase 2
0.8131	Intermediate Similarity	NPD6011	Approved
0.8119	Intermediate Similarity	NPD5695	Phase 3
0.8073	Intermediate Similarity	NPD6869	Approved
0.8073	Intermediate Similarity	NPD6847	Approved
0.8073	Intermediate Similarity	NPD8130	Phase 1
0.8073	Intermediate Similarity	NPD6617	Approved
0.8073	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6012	Approved
0.8056	Intermediate Similarity	NPD6013	Approved
0.8056	Intermediate Similarity	NPD6014	Approved
0.8041	Intermediate Similarity	NPD7146	Approved
0.8041	Intermediate Similarity	NPD5330	Approved
0.8041	Intermediate Similarity	NPD7334	Approved
0.8041	Intermediate Similarity	NPD6684	Approved
0.8041	Intermediate Similarity	NPD7521	Approved
0.8041	Intermediate Similarity	NPD6409	Approved
0.8039	Intermediate Similarity	NPD4697	Phase 3
0.8021	Intermediate Similarity	NPD3133	Approved
0.8021	Intermediate Similarity	NPD3666	Approved
0.8021	Intermediate Similarity	NPD3665	Phase 1
0.8019	Intermediate Similarity	NPD5141	Approved
0.8	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD8297	Approved
0.7981	Intermediate Similarity	NPD5286	Approved
0.7981	Intermediate Similarity	NPD5285	Approved
0.7981	Intermediate Similarity	NPD4700	Approved
0.7981	Intermediate Similarity	NPD4696	Approved
0.7944	Intermediate Similarity	NPD6008	Approved
0.7921	Intermediate Similarity	NPD4202	Approved
0.7905	Intermediate Similarity	NPD5223	Approved
0.7885	Intermediate Similarity	NPD5696	Approved
0.7879	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6903	Approved
0.7857	Intermediate Similarity	NPD3618	Phase 1
0.7857	Intermediate Similarity	NPD5786	Approved
0.7835	Intermediate Similarity	NPD4786	Approved
0.783	Intermediate Similarity	NPD5225	Approved
0.783	Intermediate Similarity	NPD5226	Approved
0.783	Intermediate Similarity	NPD5224	Approved
0.783	Intermediate Similarity	NPD4633	Approved
0.781	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7640	Approved
0.78	Intermediate Similarity	NPD4753	Phase 2
0.7788	Intermediate Similarity	NPD7902	Approved
0.7768	Intermediate Similarity	NPD4632	Approved
0.7767	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD4754	Approved
0.7757	Intermediate Similarity	NPD5175	Approved
0.7757	Intermediate Similarity	NPD5174	Approved
0.7723	Intermediate Similarity	NPD5785	Approved
0.7719	Intermediate Similarity	NPD7115	Discovery
0.7714	Intermediate Similarity	NPD7638	Approved
0.77	Intermediate Similarity	NPD6672	Approved
0.77	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD5221	Approved
0.7692	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5222	Approved
0.7679	Intermediate Similarity	NPD6053	Discontinued
0.7677	Intermediate Similarity	NPD5279	Phase 3
0.7652	Intermediate Similarity	NPD6335	Approved
0.7647	Intermediate Similarity	NPD7515	Phase 2
0.7647	Intermediate Similarity	NPD6050	Approved
0.7632	Intermediate Similarity	NPD6274	Approved
0.7629	Intermediate Similarity	NPD4221	Approved
0.7629	Intermediate Similarity	NPD3667	Approved
0.7629	Intermediate Similarity	NPD4223	Phase 3
0.7624	Intermediate Similarity	NPD6904	Approved
0.7624	Intermediate Similarity	NPD6673	Approved
0.7624	Intermediate Similarity	NPD6080	Approved
0.7619	Intermediate Similarity	NPD5173	Approved
0.7615	Intermediate Similarity	NPD4768	Approved
0.7615	Intermediate Similarity	NPD4767	Approved
0.7596	Intermediate Similarity	NPD4629	Approved
0.7596	Intermediate Similarity	NPD5210	Approved
0.7586	Intermediate Similarity	NPD7101	Approved
0.7586	Intermediate Similarity	NPD7100	Approved
0.7576	Intermediate Similarity	NPD5329	Approved
0.7576	Intermediate Similarity	NPD5363	Approved
0.7565	Intermediate Similarity	NPD6317	Approved
0.7565	Intermediate Similarity	NPD6009	Approved
0.7551	Intermediate Similarity	NPD5362	Discontinued
0.7549	Intermediate Similarity	NPD5207	Approved
0.7549	Intermediate Similarity	NPD5692	Phase 3
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD6313	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.75	Intermediate Similarity	NPD6314	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.7477	Intermediate Similarity	NPD5128	Approved
0.7477	Intermediate Similarity	NPD4729	Approved
0.7477	Intermediate Similarity	NPD4730	Approved
0.7476	Intermediate Similarity	NPD5693	Phase 1
0.7476	Intermediate Similarity	NPD5694	Approved
0.7476	Intermediate Similarity	NPD8035	Phase 2
0.7476	Intermediate Similarity	NPD8034	Phase 2
0.7475	Intermediate Similarity	NPD4197	Approved
0.7458	Intermediate Similarity	NPD6909	Approved
0.7458	Intermediate Similarity	NPD6908	Approved
0.7458	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD4270	Approved
0.7449	Intermediate Similarity	NPD4269	Approved
0.7396	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6412	Phase 2
0.7373	Intermediate Similarity	NPD6319	Approved
0.7353	Intermediate Similarity	NPD5208	Approved
0.7345	Intermediate Similarity	NPD5135	Approved
0.7345	Intermediate Similarity	NPD5248	Approved
0.7345	Intermediate Similarity	NPD5251	Approved
0.7345	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5250	Approved
0.7345	Intermediate Similarity	NPD5169	Approved
0.7345	Intermediate Similarity	NPD5249	Phase 3
0.7345	Intermediate Similarity	NPD5247	Approved
0.7345	Intermediate Similarity	NPD4634	Approved
0.7333	Intermediate Similarity	NPD7604	Phase 2
0.7333	Intermediate Similarity	NPD6001	Approved
0.7328	Intermediate Similarity	NPD6868	Approved
0.7327	Intermediate Similarity	NPD4688	Approved
0.7327	Intermediate Similarity	NPD4138	Approved
0.7327	Intermediate Similarity	NPD6098	Approved
0.7327	Intermediate Similarity	NPD4690	Approved
0.7327	Intermediate Similarity	NPD4693	Phase 3
0.7327	Intermediate Similarity	NPD4689	Approved
0.7327	Intermediate Similarity	NPD5205	Approved
0.7327	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5983	Phase 2
0.7308	Intermediate Similarity	NPD6411	Approved
0.7281	Intermediate Similarity	NPD5216	Approved
0.7281	Intermediate Similarity	NPD5215	Approved
0.7281	Intermediate Similarity	NPD5127	Approved
0.7281	Intermediate Similarity	NPD5217	Approved
0.7273	Intermediate Similarity	NPD6435	Approved
0.7273	Intermediate Similarity	NPD7492	Approved
0.7245	Intermediate Similarity	NPD5368	Approved
0.7245	Intermediate Similarity	NPD4252	Approved
0.7238	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD5779	Approved
0.7228	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6059	Approved
0.7227	Intermediate Similarity	NPD6054	Approved
0.7213	Intermediate Similarity	NPD6616	Approved
0.7213	Intermediate Similarity	NPD7507	Approved
0.7213	Intermediate Similarity	NPD6336	Discontinued
0.72	Intermediate Similarity	NPD4788	Approved
0.7182	Intermediate Similarity	NPD7632	Discontinued
0.7172	Intermediate Similarity	NPD5369	Approved
0.7156	Intermediate Similarity	NPD6404	Discontinued
0.7154	Intermediate Similarity	NPD7078	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7129	Intermediate Similarity	NPD3668	Phase 3
0.7115	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6051	Approved
0.7115	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6101	Approved
0.7107	Intermediate Similarity	NPD6370	Approved
0.7103	Intermediate Similarity	NPD5654	Approved
0.7097	Intermediate Similarity	NPD7736	Approved
0.7094	Intermediate Similarity	NPD5167	Approved
0.7071	Intermediate Similarity	NPD4820	Approved
0.7071	Intermediate Similarity	NPD4819	Approved
0.7071	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4822	Approved
0.7071	Intermediate Similarity	NPD4821	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.7059	Intermediate Similarity	NPD1694	Approved
0.7048	Intermediate Similarity	NPD4096	Approved
0.7041	Intermediate Similarity	NPD4268	Approved
0.7041	Intermediate Similarity	NPD4271	Approved
0.704	Intermediate Similarity	NPD7319	Approved
0.703	Intermediate Similarity	NPD5332	Approved
0.703	Intermediate Similarity	NPD5331	Approved
0.7025	Intermediate Similarity	NPD6016	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