NPASS Compound

Structure

CID6707 OpenBabel06191715332D 33 36 0 0 1 0 0 0 0 0999 V2000 -0.2728 3.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 -2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2526 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6409 2.3438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5393 3.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8138 2.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6894 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2102 3.4269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6879 0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6885 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2210 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 2.4357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8448 1.4617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5336 -1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2212 -1.4613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1789 3.5284 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3776 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 2.7403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5333 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0874 -1.9610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5753 4.4181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3548 1.8506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 22 2 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 21 2 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 1 1 1 0 0 0 19 20 1 0 0 0 0 20 29 1 6 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 28 1 6 0 0 0 24 26 1 0 0 0 0 24 31 1 6 0 0 0 25 27 1 0 0 0 0 25 32 1 1 0 0 0 27 33 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	514.308
LogP:	5.791
LogD:	4.881
LogS:	-4.539
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	4.908
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.786
MDCK Permeability:	1.8611324776429683e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.9

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	94.05245208740234%
Volume Distribution (VD):	1.116
Pgp-substrate:	2.1490747928619385%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.135
CYP2C9-substrate:	0.261
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.346
CYP3A4-inhibitor:	0.388
CYP3A4-substrate:	0.75

ADMET: Excretion

Clearance (CL):	6.726
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.578
Drug-inuced Liver Injury (DILI):	0.004
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.634
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.958
Carcinogencity:	0.148
Eye Corrosion:	0.066
Eye Irritation:	0.044
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC6707

Natural Product ID:	NPC6707
*Common Name:**	Lucidumol B
IUPAC Name:	(3S,6R)-6-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-2,3-diol
Synonyms:	Lucidumol B
Standard InCHIKey:	BLTRPNNWBNKAEH-LCWRUPSGSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-19(9-12-25(32)27(4,5)33)20-13-17-30(8)22-10-11-23-26(2,3)24(31)15-16-28(23,6)21(22)14-18-29(20,30)7/h10,14,19-20,23-25,31-33H,9,11-13,15-18H2,1-8H3/t19-,20-,23+,24+,25+,28-,29-,30+/m1/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)CC[C@@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915762
PubChem CID:	475411
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
ED50	2
IC50	2

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	16270.0	nM	PMID[568905]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	>	200000.0	nM	PMID[568905]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.3	ug ml-1	PMID[568906]

☑ 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 NPC6707 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	158
0.1-0.2	1271
0.2-0.3	6217
0.3-0.4	16375
0.4-0.5	7962
0.5-0.6	6481
0.6-0.7	3252
0.7-0.8	818
0.8-0.85	120
0.85-0.9	27
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9342	High Similarity	NPC205455
0.9342	High Similarity	NPC186191
0.9211	High Similarity	NPC214570
0.9146	High Similarity	NPC280556
0.9125	High Similarity	NPC231310
0.9114	High Similarity	NPC20853
0.9114	High Similarity	NPC30166
0.9114	High Similarity	NPC202389
0.9114	High Similarity	NPC201852
0.9103	High Similarity	NPC236112
0.9103	High Similarity	NPC22403
0.9103	High Similarity	NPC13554
0.9091	High Similarity	NPC275910
0.9091	High Similarity	NPC318136
0.9079	High Similarity	NPC73875
0.9079	High Similarity	NPC202642
0.9079	High Similarity	NPC46160
0.8987	High Similarity	NPC474531
0.8974	High Similarity	NPC328714
0.8947	High Similarity	NPC118508
0.8947	High Similarity	NPC121744
0.8947	High Similarity	NPC322353
0.8933	High Similarity	NPC201373
0.8889	High Similarity	NPC238485
0.8875	High Similarity	NPC7988
0.8875	High Similarity	NPC87489
0.8846	High Similarity	NPC285761
0.8831	High Similarity	NPC470362
0.8831	High Similarity	NPC189883
0.8765	High Similarity	NPC207013
0.8765	High Similarity	NPC132635
0.8734	High Similarity	NPC1319
0.8734	High Similarity	NPC273410
0.8734	High Similarity	NPC80530
0.8721	High Similarity	NPC310013
0.8718	High Similarity	NPC155986
0.8718	High Similarity	NPC318495
0.8718	High Similarity	NPC198968
0.8701	High Similarity	NPC257347
0.8701	High Similarity	NPC471723
0.8701	High Similarity	NPC141071
0.8675	High Similarity	NPC94462
0.8675	High Similarity	NPC125399
0.8675	High Similarity	NPC89077
0.8625	High Similarity	NPC236237
0.8625	High Similarity	NPC102253
0.8625	High Similarity	NPC322313
0.8608	High Similarity	NPC167037
0.8608	High Similarity	NPC138621
0.8608	High Similarity	NPC76931
0.8608	High Similarity	NPC6978
0.8608	High Similarity	NPC72507
0.8608	High Similarity	NPC18603
0.8608	High Similarity	NPC307965
0.8608	High Similarity	NPC244385
0.859	High Similarity	NPC240604
0.859	High Similarity	NPC321381
0.859	High Similarity	NPC237460
0.859	High Similarity	NPC300324
0.859	High Similarity	NPC129165
0.859	High Similarity	NPC134330
0.859	High Similarity	NPC315261
0.859	High Similarity	NPC321016
0.859	High Similarity	NPC107059
0.859	High Similarity	NPC91573
0.859	High Similarity	NPC106432
0.8571	High Similarity	NPC475772
0.8553	High Similarity	NPC110799
0.8537	High Similarity	NPC470384
0.8537	High Similarity	NPC474634
0.8537	High Similarity	NPC317458
0.8519	High Similarity	NPC70927
0.85	High Similarity	NPC30986
0.85	High Similarity	NPC209430
0.8488	Intermediate Similarity	NPC107189
0.8471	Intermediate Similarity	NPC133588
0.8471	Intermediate Similarity	NPC470542
0.8471	Intermediate Similarity	NPC44181
0.8462	Intermediate Similarity	NPC22105
0.8462	Intermediate Similarity	NPC136188
0.8462	Intermediate Similarity	NPC134847
0.8462	Intermediate Similarity	NPC471468
0.8462	Intermediate Similarity	NPC28657
0.8462	Intermediate Similarity	NPC477923
0.8462	Intermediate Similarity	NPC66566
0.8462	Intermediate Similarity	NPC230301
0.8462	Intermediate Similarity	NPC285893
0.8462	Intermediate Similarity	NPC304309
0.8462	Intermediate Similarity	NPC162742
0.8462	Intermediate Similarity	NPC288035
0.8442	Intermediate Similarity	NPC474140
0.8434	Intermediate Similarity	NPC470077
0.8434	Intermediate Similarity	NPC474493
0.8434	Intermediate Similarity	NPC185568
0.8415	Intermediate Similarity	NPC470049
0.8415	Intermediate Similarity	NPC296701
0.8415	Intermediate Similarity	NPC49964
0.8415	Intermediate Similarity	NPC218616
0.8395	Intermediate Similarity	NPC241290
0.8395	Intermediate Similarity	NPC209944
0.8395	Intermediate Similarity	NPC164840
0.8375	Intermediate Similarity	NPC85346
0.8375	Intermediate Similarity	NPC65897
0.8375	Intermediate Similarity	NPC302041
0.8375	Intermediate Similarity	NPC477522
0.8375	Intermediate Similarity	NPC473943
0.8375	Intermediate Similarity	NPC474216
0.8375	Intermediate Similarity	NPC87604
0.8372	Intermediate Similarity	NPC84271
0.8372	Intermediate Similarity	NPC102414
0.8372	Intermediate Similarity	NPC470361
0.8372	Intermediate Similarity	NPC77168
0.8354	Intermediate Similarity	NPC113733
0.8353	Intermediate Similarity	NPC271967
0.8353	Intermediate Similarity	NPC138756
0.8333	Intermediate Similarity	NPC27395
0.8333	Intermediate Similarity	NPC318390
0.8333	Intermediate Similarity	NPC329090
0.8312	Intermediate Similarity	NPC167706
0.8293	Intermediate Similarity	NPC470383
0.8293	Intermediate Similarity	NPC47761
0.8293	Intermediate Similarity	NPC264245
0.8276	Intermediate Similarity	NPC11216
0.8276	Intermediate Similarity	NPC204188
0.8276	Intermediate Similarity	NPC291484
0.8276	Intermediate Similarity	NPC3345
0.8276	Intermediate Similarity	NPC80561
0.8276	Intermediate Similarity	NPC329596
0.8272	Intermediate Similarity	NPC81306
0.8272	Intermediate Similarity	NPC109546
0.8272	Intermediate Similarity	NPC143182
0.8272	Intermediate Similarity	NPC28862
0.8272	Intermediate Similarity	NPC47982
0.8272	Intermediate Similarity	NPC84694
0.8256	Intermediate Similarity	NPC2158
0.8256	Intermediate Similarity	NPC474668
0.825	Intermediate Similarity	NPC477924
0.825	Intermediate Similarity	NPC130136
0.825	Intermediate Similarity	NPC34019
0.8235	Intermediate Similarity	NPC94755
0.8235	Intermediate Similarity	NPC261266
0.8235	Intermediate Similarity	NPC477604
0.8235	Intermediate Similarity	NPC269058
0.8235	Intermediate Similarity	NPC473168
0.8235	Intermediate Similarity	NPC6391
0.8235	Intermediate Similarity	NPC71520
0.8228	Intermediate Similarity	NPC319090
0.8228	Intermediate Similarity	NPC3403
0.8228	Intermediate Similarity	NPC328104
0.8214	Intermediate Similarity	NPC205845
0.8214	Intermediate Similarity	NPC474047
0.8214	Intermediate Similarity	NPC478102
0.8214	Intermediate Similarity	NPC124172
0.8214	Intermediate Similarity	NPC209802
0.8205	Intermediate Similarity	NPC182717
0.8193	Intermediate Similarity	NPC101462
0.8193	Intermediate Similarity	NPC248886
0.8182	Intermediate Similarity	NPC471453
0.8182	Intermediate Similarity	NPC41554
0.8182	Intermediate Similarity	NPC212948
0.8182	Intermediate Similarity	NPC210268
0.8182	Intermediate Similarity	NPC97404
0.8171	Intermediate Similarity	NPC234193
0.8171	Intermediate Similarity	NPC26117
0.8161	Intermediate Similarity	NPC32830
0.8161	Intermediate Similarity	NPC105495
0.8158	Intermediate Similarity	NPC216460
0.8148	Intermediate Similarity	NPC102708
0.8148	Intermediate Similarity	NPC312328
0.8148	Intermediate Similarity	NPC477514
0.814	Intermediate Similarity	NPC187376
0.814	Intermediate Similarity	NPC470620
0.814	Intermediate Similarity	NPC233836
0.814	Intermediate Similarity	NPC159046
0.8125	Intermediate Similarity	NPC96319
0.8125	Intermediate Similarity	NPC274079
0.8125	Intermediate Similarity	NPC244488
0.8125	Intermediate Similarity	NPC265588
0.8125	Intermediate Similarity	NPC477925
0.8125	Intermediate Similarity	NPC247325
0.8118	Intermediate Similarity	NPC274448
0.8118	Intermediate Similarity	NPC470360
0.8118	Intermediate Similarity	NPC157257
0.8101	Intermediate Similarity	NPC469533
0.8101	Intermediate Similarity	NPC469534
0.8101	Intermediate Similarity	NPC100334
0.8101	Intermediate Similarity	NPC477138
0.8101	Intermediate Similarity	NPC469593
0.8101	Intermediate Similarity	NPC91858
0.8101	Intermediate Similarity	NPC243342
0.8095	Intermediate Similarity	NPC477818
0.8095	Intermediate Similarity	NPC113978
0.8095	Intermediate Similarity	NPC475789
0.8095	Intermediate Similarity	NPC110778
0.8095	Intermediate Similarity	NPC82538
0.8095	Intermediate Similarity	NPC134481
0.8095	Intermediate Similarity	NPC470558
0.8095	Intermediate Similarity	NPC82623
0.8095	Intermediate Similarity	NPC237795
0.809	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 NPC6707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1609
0.2-0.3	4416
0.3-0.4	2130
0.4-0.5	442
0.5-0.6	196
0.6-0.7	156
0.7-0.8	45
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8625	High Similarity	NPD7525	Registered
0.859	High Similarity	NPD6933	Approved
0.8462	Intermediate Similarity	NPD7339	Approved
0.8462	Intermediate Similarity	NPD6942	Approved
0.8333	Intermediate Similarity	NPD6926	Approved
0.8333	Intermediate Similarity	NPD6924	Approved
0.8171	Intermediate Similarity	NPD4748	Discontinued
0.8125	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7150	Approved
0.7848	Intermediate Similarity	NPD7152	Approved
0.7848	Intermediate Similarity	NPD4243	Approved
0.7848	Intermediate Similarity	NPD7151	Approved
0.7831	Intermediate Similarity	NPD7645	Phase 2
0.7821	Intermediate Similarity	NPD6922	Approved
0.7821	Intermediate Similarity	NPD6923	Approved
0.7791	Intermediate Similarity	NPD4786	Approved
0.7753	Intermediate Similarity	NPD5328	Approved
0.7738	Intermediate Similarity	NPD6931	Approved
0.7738	Intermediate Similarity	NPD6930	Phase 2
0.7738	Intermediate Similarity	NPD7509	Discontinued
0.7722	Intermediate Similarity	NPD7144	Approved
0.7722	Intermediate Similarity	NPD7143	Approved
0.7654	Intermediate Similarity	NPD4785	Approved
0.7654	Intermediate Similarity	NPD4784	Approved
0.7619	Intermediate Similarity	NPD6929	Approved
0.7614	Intermediate Similarity	NPD5279	Phase 3
0.7614	Intermediate Similarity	NPD3618	Phase 1
0.7595	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6932	Approved
0.7582	Intermediate Similarity	NPD6079	Approved
0.7561	Intermediate Similarity	NPD8264	Approved
0.7558	Intermediate Similarity	NPD3667	Approved
0.7528	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7524	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7471	Intermediate Similarity	NPD6695	Phase 3
0.7412	Intermediate Similarity	NPD6683	Phase 2
0.7386	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5776	Phase 2
0.7381	Intermediate Similarity	NPD6925	Approved
0.7349	Intermediate Similarity	NPD4190	Phase 3
0.7349	Intermediate Similarity	NPD5275	Approved
0.7326	Intermediate Similarity	NPD7514	Phase 3
0.7303	Intermediate Similarity	NPD6893	Approved
0.7294	Intermediate Similarity	NPD7145	Approved
0.7294	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4694	Approved
0.7222	Intermediate Similarity	NPD5280	Approved
0.7209	Intermediate Similarity	NPD4195	Approved
0.7191	Intermediate Similarity	NPD3133	Approved
0.7191	Intermediate Similarity	NPD3665	Phase 1
0.7191	Intermediate Similarity	NPD3666	Approved
0.7188	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD7750	Discontinued
0.7126	Intermediate Similarity	NPD7332	Phase 2
0.7111	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5221	Approved
0.7083	Intermediate Similarity	NPD5222	Approved
0.7083	Intermediate Similarity	NPD4697	Phase 3
0.7083	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6902	Approved
0.7045	Intermediate Similarity	NPD6898	Phase 1
0.7041	Intermediate Similarity	NPD5286	Approved
0.7041	Intermediate Similarity	NPD5285	Approved
0.7041	Intermediate Similarity	NPD4700	Approved
0.7041	Intermediate Similarity	NPD4696	Approved
0.701	Intermediate Similarity	NPD5173	Approved
0.6989	Remote Similarity	NPD4753	Phase 2
0.697	Remote Similarity	NPD5223	Approved
0.6966	Remote Similarity	NPD4223	Phase 3
0.6966	Remote Similarity	NPD4221	Approved
0.6947	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD5329	Approved
0.69	Remote Similarity	NPD5225	Approved
0.69	Remote Similarity	NPD5226	Approved
0.69	Remote Similarity	NPD4633	Approved
0.69	Remote Similarity	NPD5211	Phase 2
0.69	Remote Similarity	NPD5224	Approved
0.6867	Remote Similarity	NPD4787	Phase 1
0.6863	Remote Similarity	NPD7128	Approved
0.6863	Remote Similarity	NPD5739	Approved
0.6863	Remote Similarity	NPD6402	Approved
0.6863	Remote Similarity	NPD6675	Approved
0.6854	Remote Similarity	NPD4692	Approved
0.6854	Remote Similarity	NPD4139	Approved
0.6848	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5690	Phase 2
0.6842	Remote Similarity	NPD5284	Approved
0.6842	Remote Similarity	NPD7087	Discontinued
0.6842	Remote Similarity	NPD7515	Phase 2
0.6842	Remote Similarity	NPD5281	Approved
0.6832	Remote Similarity	NPD5175	Approved
0.6832	Remote Similarity	NPD5174	Approved
0.6832	Remote Similarity	NPD4754	Approved
0.6813	Remote Similarity	NPD4197	Approved
0.6813	Remote Similarity	NPD3668	Phase 3
0.68	Remote Similarity	NPD4159	Approved
0.6771	Remote Similarity	NPD5133	Approved
0.6768	Remote Similarity	NPD7638	Approved
0.6768	Remote Similarity	NPD5290	Discontinued
0.6765	Remote Similarity	NPD5141	Approved
0.6762	Remote Similarity	NPD4634	Approved
0.6737	Remote Similarity	NPD4096	Approved
0.6731	Remote Similarity	NPD6881	Approved
0.6731	Remote Similarity	NPD6899	Approved
0.6731	Remote Similarity	NPD7320	Approved
0.6703	Remote Similarity	NPD4788	Approved
0.67	Remote Similarity	NPD7640	Approved
0.67	Remote Similarity	NPD7639	Approved
0.6699	Remote Similarity	NPD4768	Approved
0.6699	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6636	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD5701	Approved
0.6635	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD4629	Approved
0.6633	Remote Similarity	NPD5210	Approved
0.6633	Remote Similarity	NPD5695	Phase 3
0.6632	Remote Similarity	NPD6051	Approved
0.6628	Remote Similarity	NPD5733	Approved
0.6604	Remote Similarity	NPD7290	Approved
0.6604	Remote Similarity	NPD7102	Approved
0.6604	Remote Similarity	NPD6883	Approved
0.6588	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD4730	Approved
0.6571	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD5128	Approved
0.6571	Remote Similarity	NPD4729	Approved
0.6545	Remote Similarity	NPD7115	Discovery
0.6542	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD8130	Phase 1
0.6542	Remote Similarity	NPD6869	Approved
0.6542	Remote Similarity	NPD6847	Approved
0.6542	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6649	Approved
0.6542	Remote Similarity	NPD6617	Approved
0.6531	Remote Similarity	NPD7748	Approved
0.6526	Remote Similarity	NPD4518	Approved
0.6526	Remote Similarity	NPD4723	Approved
0.6526	Remote Similarity	NPD4722	Approved
0.6517	Remote Similarity	NPD3617	Approved
0.6509	Remote Similarity	NPD6013	Approved
0.6509	Remote Similarity	NPD6014	Approved
0.6509	Remote Similarity	NPD6012	Approved
0.65	Remote Similarity	NPD368	Approved
0.6495	Remote Similarity	NPD8035	Phase 2
0.6495	Remote Similarity	NPD8034	Phase 2
0.6495	Remote Similarity	NPD6411	Approved
0.6495	Remote Similarity	NPD6050	Approved
0.6489	Remote Similarity	NPD7521	Approved
0.6489	Remote Similarity	NPD7334	Approved
0.6489	Remote Similarity	NPD7146	Approved
0.6489	Remote Similarity	NPD5330	Approved
0.6489	Remote Similarity	NPD6684	Approved
0.6489	Remote Similarity	NPD6409	Approved
0.6481	Remote Similarity	NPD6882	Approved
0.6477	Remote Similarity	NPD6117	Approved
0.646	Remote Similarity	NPD7503	Approved
0.6449	Remote Similarity	NPD5135	Approved
0.6449	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5250	Approved
0.6449	Remote Similarity	NPD5251	Approved
0.6449	Remote Similarity	NPD5247	Approved
0.6449	Remote Similarity	NPD5169	Approved
0.6449	Remote Similarity	NPD5249	Phase 3
0.6449	Remote Similarity	NPD5248	Approved
0.6437	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4687	Approved
0.6415	Remote Similarity	NPD5168	Approved
0.6404	Remote Similarity	NPD6116	Phase 1
0.6395	Remote Similarity	NPD5276	Approved
0.6392	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5207	Approved
0.6392	Remote Similarity	NPD5692	Phase 3
0.6389	Remote Similarity	NPD5215	Approved
0.6389	Remote Similarity	NPD5217	Approved
0.6389	Remote Similarity	NPD5127	Approved
0.6389	Remote Similarity	NPD5216	Approved
0.6383	Remote Similarity	NPD1696	Phase 3
0.6374	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6672	Approved
0.6354	Remote Similarity	NPD5737	Approved
0.6354	Remote Similarity	NPD6903	Approved
0.6354	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7327	Approved
0.6339	Remote Similarity	NPD7328	Approved
0.6337	Remote Similarity	NPD7902	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