NPASS Compound

Structure

CID109514 OpenBabel06191715462D 22 24 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 12 2 0 0 0 0 10 12 1 0 0 0 0 11 15 2 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.14
Volume:	319.426
LogP:	4.399
LogD:	3.261
LogS:	-4.122
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.767
Synthetic Accessibility Score:	2.984
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.813
MDCK Permeability:	1.9913280993932858e-05
Pgp-inhibitor:	0.181
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.172
30% Bioavailability (F30%):	0.564

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	100.43242645263672%
Volume Distribution (VD):	0.827
Pgp-substrate:	1.5089893341064453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.629
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.122
CYP2C9-inhibitor:	0.839
CYP2C9-substrate:	0.811
CYP2D6-inhibitor:	0.893
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.495
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	1.862
Half-life (T1/2):	0.242

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.681
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.381
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.934
Carcinogencity:	0.745
Eye Corrosion:	0.004
Eye Irritation:	0.921
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC109514

Natural Product ID:	NPC109514
*Common Name:**	1-Oxomiltirone
IUPAC Name:	8,8-dimethyl-2-propan-2-yl-6,7-dihydrophenanthrene-3,4,5-trione
Synonyms:	1-Oxomiltirone
Standard InCHIKey:	VPIMKJVQYOXHSS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O3/c1-10(2)12-9-11-5-6-13-16(15(11)18(22)17(12)21)14(20)7-8-19(13,3)4/h5-6,9-10H,7-8H2,1-4H3
SMILES:	CC(C1=Cc2ccc3c(c2C(=O)C1=O)C(=O)CCC3(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485479
PubChem CID:	9971798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

*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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720520]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24210499]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	whole plants	east Texas, USA	2009-2011	PMID[24210499]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	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
GI50	6
IC50	6

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	4
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	44600.0	nM	PMID[543656]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	29900.0	nM	PMID[543657]
NPT171	Cell Line	MRC5	Homo sapiens	GI50	=	20390.0	nM	PMID[543658]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	23270.0	nM	PMID[543658]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	18970.0	nM	PMID[543658]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	24890.0	nM	PMID[543658]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	17900.0	nM	PMID[543656]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	13000.0	nM	PMID[543656]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	46600.0	nM	PMID[543656]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47800.0	nM	PMID[543656]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	20540.0	nM	PMID[543658]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	32150.0	nM	PMID[543658]

☑ 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 NPC109514 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	341
0.1-0.2	1610
0.2-0.3	4504
0.3-0.4	14722
0.4-0.5	14507
0.5-0.6	5932
0.6-0.7	843
0.7-0.8	174
0.8-0.85	29
0.85-0.9	16
0.9-0.95	14
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9785	High Similarity	NPC134882
0.9677	High Similarity	NPC265220
0.9677	High Similarity	NPC239185
0.9579	High Similarity	NPC476993
0.9574	High Similarity	NPC75724
0.9368	High Similarity	NPC49994
0.9362	High Similarity	NPC219573
0.9362	High Similarity	NPC185208
0.9355	High Similarity	NPC238219
0.93	High Similarity	NPC470252
0.9255	High Similarity	NPC260233
0.9247	High Similarity	NPC323420
0.9247	High Similarity	NPC155232
0.9247	High Similarity	NPC59677
0.9247	High Similarity	NPC153885
0.914	High Similarity	NPC133461
0.9043	High Similarity	NPC188844
0.9043	High Similarity	NPC1682
0.9032	High Similarity	NPC173413
0.8947	High Similarity	NPC289883
0.8936	High Similarity	NPC284475
0.8817	High Similarity	NPC157778
0.88	High Similarity	NPC471829
0.88	High Similarity	NPC475939
0.88	High Similarity	NPC472691
0.88	High Similarity	NPC474866
0.8723	High Similarity	NPC298115
0.871	High Similarity	NPC43945
0.8667	High Similarity	NPC280789
0.8632	High Similarity	NPC19256
0.8632	High Similarity	NPC277277
0.8602	High Similarity	NPC307
0.8602	High Similarity	NPC160339
0.8585	High Similarity	NPC93287
0.8585	High Similarity	NPC470253
0.8544	High Similarity	NPC472699
0.8544	High Similarity	NPC472700
0.8526	High Similarity	NPC418308
0.8511	High Similarity	NPC69057
0.8505	High Similarity	NPC471721
0.8505	High Similarity	NPC326664
0.8469	Intermediate Similarity	NPC472880
0.8462	Intermediate Similarity	NPC472695
0.8462	Intermediate Similarity	NPC472696
0.8462	Intermediate Similarity	NPC472683
0.8462	Intermediate Similarity	NPC472701
0.8431	Intermediate Similarity	NPC247976
0.8426	Intermediate Similarity	NPC215419
0.8421	Intermediate Similarity	NPC267262
0.8416	Intermediate Similarity	NPC472879
0.8411	Intermediate Similarity	NPC143768
0.8396	Intermediate Similarity	NPC265513
0.828	Intermediate Similarity	NPC215008
0.8273	Intermediate Similarity	NPC469843
0.8241	Intermediate Similarity	NPC471481
0.819	Intermediate Similarity	NPC100767
0.8173	Intermediate Similarity	NPC329282
0.8165	Intermediate Similarity	NPC130591
0.8165	Intermediate Similarity	NPC234637
0.8163	Intermediate Similarity	NPC125226
0.8065	Intermediate Similarity	NPC145053
0.8041	Intermediate Similarity	NPC153308
0.8036	Intermediate Similarity	NPC222968
0.8036	Intermediate Similarity	NPC80605
0.8036	Intermediate Similarity	NPC323440
0.7982	Intermediate Similarity	NPC218855
0.7982	Intermediate Similarity	NPC292834
0.798	Intermediate Similarity	NPC103346
0.7957	Intermediate Similarity	NPC285716
0.7957	Intermediate Similarity	NPC17408
0.7957	Intermediate Similarity	NPC190567
0.7925	Intermediate Similarity	NPC172483
0.7925	Intermediate Similarity	NPC474910
0.7895	Intermediate Similarity	NPC202015
0.7895	Intermediate Similarity	NPC273758
0.7876	Intermediate Similarity	NPC268930
0.7872	Intermediate Similarity	NPC273033
0.7872	Intermediate Similarity	NPC12936
0.7849	Intermediate Similarity	NPC300205
0.7845	Intermediate Similarity	NPC269923
0.7845	Intermediate Similarity	NPC167323
0.7835	Intermediate Similarity	NPC164526
0.7807	Intermediate Similarity	NPC318173
0.7788	Intermediate Similarity	NPC221825
0.7778	Intermediate Similarity	NPC325709
0.7778	Intermediate Similarity	NPC113307
0.7767	Intermediate Similarity	NPC226041
0.7766	Intermediate Similarity	NPC71664
0.7766	Intermediate Similarity	NPC164086
0.7766	Intermediate Similarity	NPC477703
0.7757	Intermediate Similarity	NPC471186
0.7742	Intermediate Similarity	NPC36342
0.7742	Intermediate Similarity	NPC285470
0.7742	Intermediate Similarity	NPC2785
0.7742	Intermediate Similarity	NPC103488
0.7736	Intermediate Similarity	NPC274443
0.7732	Intermediate Similarity	NPC252067
0.7727	Intermediate Similarity	NPC474057
0.7727	Intermediate Similarity	NPC137315
0.7714	Intermediate Similarity	NPC225079
0.7714	Intermediate Similarity	NPC133809
0.7714	Intermediate Similarity	NPC136810
0.7714	Intermediate Similarity	NPC128248
0.7712	Intermediate Similarity	NPC85511
0.7712	Intermediate Similarity	NPC51079
0.7712	Intermediate Similarity	NPC328107
0.77	Intermediate Similarity	NPC58872
0.7699	Intermediate Similarity	NPC260886
0.7679	Intermediate Similarity	NPC67377
0.7672	Intermediate Similarity	NPC476225
0.766	Intermediate Similarity	NPC151405
0.766	Intermediate Similarity	NPC139901
0.7658	Intermediate Similarity	NPC186128
0.7652	Intermediate Similarity	NPC472698
0.7652	Intermediate Similarity	NPC472697
0.7642	Intermediate Similarity	NPC244427
0.7642	Intermediate Similarity	NPC222390
0.7634	Intermediate Similarity	NPC245966
0.7615	Intermediate Similarity	NPC203732
0.7611	Intermediate Similarity	NPC93181
0.7611	Intermediate Similarity	NPC474095
0.7611	Intermediate Similarity	NPC217111
0.7607	Intermediate Similarity	NPC472981
0.7596	Intermediate Similarity	NPC240042
0.7593	Intermediate Similarity	NPC134120
0.7586	Intermediate Similarity	NPC476645
0.757	Intermediate Similarity	NPC329556
0.7565	Intermediate Similarity	NPC61651
0.7545	Intermediate Similarity	NPC192577
0.7526	Intermediate Similarity	NPC197581
0.7526	Intermediate Similarity	NPC39600
0.7525	Intermediate Similarity	NPC67585
0.7525	Intermediate Similarity	NPC26224
0.7525	Intermediate Similarity	NPC303967
0.7525	Intermediate Similarity	NPC110420
0.7522	Intermediate Similarity	NPC294458
0.7521	Intermediate Similarity	NPC474106
0.7521	Intermediate Similarity	NPC232958
0.7521	Intermediate Similarity	NPC472679
0.7521	Intermediate Similarity	NPC77000
0.7521	Intermediate Similarity	NPC472680
0.7521	Intermediate Similarity	NPC238861
0.7478	Intermediate Similarity	NPC158157
0.7474	Intermediate Similarity	NPC272260
0.7458	Intermediate Similarity	NPC476234
0.7456	Intermediate Similarity	NPC228936
0.7455	Intermediate Similarity	NPC470007
0.7455	Intermediate Similarity	NPC112903
0.7453	Intermediate Similarity	NPC54647
0.7451	Intermediate Similarity	NPC475023
0.7451	Intermediate Similarity	NPC475059
0.7447	Intermediate Similarity	NPC249018
0.7447	Intermediate Similarity	NPC3190
0.7447	Intermediate Similarity	NPC9796
0.7423	Intermediate Similarity	NPC230068
0.7417	Intermediate Similarity	NPC318067
0.7396	Intermediate Similarity	NPC95868
0.7383	Intermediate Similarity	NPC112552
0.7379	Intermediate Similarity	NPC475057
0.7368	Intermediate Similarity	NPC196673
0.7368	Intermediate Similarity	NPC241851
0.7364	Intermediate Similarity	NPC83409
0.7364	Intermediate Similarity	NPC185763
0.7364	Intermediate Similarity	NPC142326
0.7364	Intermediate Similarity	NPC94751
0.7364	Intermediate Similarity	NPC85560
0.7364	Intermediate Similarity	NPC37914
0.7364	Intermediate Similarity	NPC244933
0.7345	Intermediate Similarity	NPC66208
0.7345	Intermediate Similarity	NPC471189
0.7345	Intermediate Similarity	NPC471188
0.732	Intermediate Similarity	NPC73978
0.732	Intermediate Similarity	NPC100039
0.7317	Intermediate Similarity	NPC478162
0.7317	Intermediate Similarity	NPC51448
0.7317	Intermediate Similarity	NPC478165
0.7317	Intermediate Similarity	NPC115797
0.7311	Intermediate Similarity	NPC144547
0.7304	Intermediate Similarity	NPC186933
0.7292	Intermediate Similarity	NPC159661
0.7288	Intermediate Similarity	NPC204784
0.7281	Intermediate Similarity	NPC13784
0.7273	Intermediate Similarity	NPC472681
0.7264	Intermediate Similarity	NPC156021
0.7263	Intermediate Similarity	NPC179726
0.7257	Intermediate Similarity	NPC95126
0.7257	Intermediate Similarity	NPC291799
0.7257	Intermediate Similarity	NPC475002
0.7241	Intermediate Similarity	NPC135730
0.7236	Intermediate Similarity	NPC470648
0.7227	Intermediate Similarity	NPC988
0.7227	Intermediate Similarity	NPC289432
0.7217	Intermediate Similarity	NPC196075
0.7216	Intermediate Similarity	NPC157055
0.7213	Intermediate Similarity	NPC472693
0.7213	Intermediate Similarity	NPC295664
0.7213	Intermediate Similarity	NPC472694
0.7204	Intermediate Similarity	NPC54269
0.7204	Intermediate Similarity	NPC285679
0.72	Intermediate Similarity	NPC123476

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 NPC109514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	1013
0.2-0.3	1615
0.3-0.4	3342
0.4-0.5	2106
0.5-0.6	618
0.6-0.7	104
0.7-0.8	26
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9677	High Similarity	NPD3495	Discontinued
0.9043	High Similarity	NPD7631	Approved
0.8936	High Similarity	NPD7609	Phase 3
0.871	High Similarity	NPD650	Approved
0.8081	Intermediate Similarity	NPD1508	Approved
0.789	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD942	Approved
0.7843	Intermediate Similarity	NPD1843	Approved
0.7652	Intermediate Similarity	NPD7009	Phase 2
0.7619	Intermediate Similarity	NPD2066	Phase 3
0.7611	Intermediate Similarity	NPD5951	Approved
0.757	Intermediate Similarity	NPD1929	Approved
0.757	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD1930	Approved
0.7565	Intermediate Similarity	NPD7610	Discontinued
0.7521	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1932	Approved
0.7458	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6049	Phase 2
0.7404	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD2329	Discontinued
0.7373	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2648	Phase 3
0.7315	Intermediate Similarity	NPD2193	Phase 2
0.7308	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7094	Approved
0.7281	Intermediate Similarity	NPD6858	Approved
0.7232	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5836	Discontinued
0.7167	Intermediate Similarity	NPD4879	Approved
0.7156	Intermediate Similarity	NPD2196	Discontinued
0.7075	Intermediate Similarity	NPD4094	Approved
0.7059	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1087	Approved
0.7048	Intermediate Similarity	NPD1088	Approved
0.7043	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4655	Approved
0.6944	Remote Similarity	NPD4657	Approved
0.6935	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD1693	Approved
0.687	Remote Similarity	NPD1317	Discontinued
0.6863	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1089	Approved
0.6857	Remote Similarity	NPD1090	Approved
0.6857	Remote Similarity	NPD1086	Approved
0.6852	Remote Similarity	NPD1989	Approved
0.6847	Remote Similarity	NPD6024	Approved
0.6847	Remote Similarity	NPD2171	Approved
0.6847	Remote Similarity	NPD6027	Approved
0.6832	Remote Similarity	NPD3971	Phase 1
0.6822	Remote Similarity	NPD1563	Approved
0.6822	Remote Similarity	NPD7961	Discontinued
0.6814	Remote Similarity	NPD2197	Approved
0.6814	Remote Similarity	NPD2192	Approved
0.6814	Remote Similarity	NPD1677	Discontinued
0.6807	Remote Similarity	NPD3317	Approved
0.6797	Remote Similarity	NPD7008	Discontinued
0.6797	Remote Similarity	NPD2754	Discontinued
0.6797	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4878	Approved
0.6771	Remote Similarity	NPD4058	Approved
0.6762	Remote Similarity	NPD800	Approved
0.6759	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5909	Discontinued
0.6726	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2932	Approved
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.664	Remote Similarity	NPD3972	Approved
0.6639	Remote Similarity	NPD7077	Approved
0.6639	Remote Similarity	NPD7076	Approved
0.6638	Remote Similarity	NPD2182	Approved
0.6637	Remote Similarity	NPD3357	Discontinued
0.6636	Remote Similarity	NPD1100	Approved
0.6636	Remote Similarity	NPD1565	Approved
0.6636	Remote Similarity	NPD1099	Approved
0.6636	Remote Similarity	NPD1566	Phase 3
0.6636	Remote Similarity	NPD1564	Approved
0.6636	Remote Similarity	NPD1239	Approved
0.6585	Remote Similarity	NPD3025	Approved
0.6585	Remote Similarity	NPD3024	Approved
0.6581	Remote Similarity	NPD664	Approved
0.6579	Remote Similarity	NPD164	Approved
0.6579	Remote Similarity	NPD1237	Approved
0.656	Remote Similarity	NPD6287	Discontinued
0.6542	Remote Similarity	NPD3672	Approved
0.6542	Remote Similarity	NPD3673	Approved
0.6532	Remote Similarity	NPD3019	Approved
0.6532	Remote Similarity	NPD2345	Approved
0.6514	Remote Similarity	NPD1202	Approved
0.6512	Remote Similarity	NPD7084	Phase 3
0.648	Remote Similarity	NPD3026	Approved
0.648	Remote Similarity	NPD3023	Approved
0.648	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4691	Approved
0.6452	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5347	Phase 2
0.6449	Remote Similarity	NPD5346	Phase 2
0.6446	Remote Similarity	NPD2508	Discontinued
0.6442	Remote Similarity	NPD4544	Approved
0.6429	Remote Similarity	NPD4687	Approved
0.6406	Remote Similarity	NPD1876	Approved
0.6404	Remote Similarity	NPD813	Approved
0.64	Remote Similarity	NPD4199	Phase 3
0.6364	Remote Similarity	NPD6010	Discontinued
0.6357	Remote Similarity	NPD1470	Approved
0.6357	Remote Similarity	NPD3245	Phase 3
0.6357	Remote Similarity	NPD3244	Pre-registration
0.6354	Remote Similarity	NPD4137	Phase 3
0.6337	Remote Similarity	NPD225	Approved
0.6337	Remote Similarity	NPD227	Approved
0.6336	Remote Similarity	NPD7055	Discontinued
0.6331	Remote Similarity	NPD7003	Approved
0.6328	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD3549	Approved
0.6328	Remote Similarity	NPD3547	Approved
0.6321	Remote Similarity	NPD9257	Approved
0.6321	Remote Similarity	NPD9259	Approved
0.6316	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7713	Phase 3
0.6316	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1201	Approved
0.6289	Remote Similarity	NPD4747	Approved
0.6275	Remote Similarity	NPD9490	Approved
0.6263	Remote Similarity	NPD5733	Approved
0.6262	Remote Similarity	NPD4793	Discontinued
0.6261	Remote Similarity	NPD4803	Discontinued
0.625	Remote Similarity	NPD3093	Approved
0.6241	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1238	Approved
0.6228	Remote Similarity	NPD742	Approved
0.6224	Remote Similarity	NPD5276	Approved
0.621	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6647	Phase 2
0.619	Remote Similarity	NPD9491	Approved
0.619	Remote Similarity	NPD1245	Approved
0.619	Remote Similarity	NPD1651	Approved
0.6183	Remote Similarity	NPD4980	Approved
0.6183	Remote Similarity	NPD2798	Approved
0.6179	Remote Similarity	NPD2319	Discontinued
0.6179	Remote Similarity	NPD2629	Approved
0.6174	Remote Similarity	NPD6354	Discontinued
0.617	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.616	Remote Similarity	NPD997	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6065	Approved
0.6154	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD226	Approved
0.614	Remote Similarity	NPD466	Approved
0.6127	Remote Similarity	NPD7236	Approved
0.6119	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD2346	Discontinued
0.6107	Remote Similarity	NPD5653	Discontinued
0.6091	Remote Similarity	NPD9256	Approved
0.6091	Remote Similarity	NPD9258	Approved
0.6087	Remote Similarity	NPD7798	Approved
0.6087	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD5159	Phase 2
0.6077	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD5157	Phase 1
0.6071	Remote Similarity	NPD2878	Approved
0.6071	Remote Similarity	NPD3982	Approved
0.6071	Remote Similarity	NPD3980	Approved
0.6068	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5598	Approved
0.6053	Remote Similarity	NPD5597	Approved
0.6048	Remote Similarity	NPD1246	Approved
0.6048	Remote Similarity	NPD3867	Phase 2
0.6048	Remote Similarity	NPD4766	Approved
0.6047	Remote Similarity	NPD1281	Approved
0.6045	Remote Similarity	NPD6966	Discovery
0.6043	Remote Similarity	NPD5408	Approved
0.6043	Remote Similarity	NPD5405	Approved
0.6043	Remote Similarity	NPD5404	Approved
0.6043	Remote Similarity	NPD5406	Approved
0.604	Remote Similarity	NPD9716	Approved
0.6038	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5991	Approved
0.6032	Remote Similarity	NPD5990	Approved
0.6031	Remote Similarity	NPD2056	Discontinued
0.6027	Remote Similarity	NPD7239	Suspended
0.6019	Remote Similarity	NPD3099	Discontinued
0.6016	Remote Similarity	NPD2607	Approved
0.6	Remote Similarity	NPD5926	Approved
0.6	Remote Similarity	NPD1471	Phase 3
0.6	Remote Similarity	NPD3355	Approved
0.6	Remote Similarity	NPD675	Discontinued
0.6	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3356	Approved
0.6	Remote Similarity	NPD6637	Approved
0.5986	Remote Similarity	NPD3226	Approved
0.5984	Remote Similarity	NPD3642	Approved
0.5984	Remote Similarity	NPD3643	Approved
0.5984	Remote Similarity	NPD3644	Approved
0.5971	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD1018	Approved
0.5966	Remote Similarity	NPD1767	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