NPASS Compound

Structure

CID30846 OpenBabel06191715362D 45 47 0 0 1 0 0 0 0 0999 V2000 -3.6244 -1.3388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1244 -0.4728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0763 6.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7838 6.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2736 1.1513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3790 2.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1278 3.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2416 -1.8388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3756 -2.3388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1244 -2.2048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1817 5.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9174 -3.5783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1244 -2.2048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4119 4.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4174 -4.4443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9811 0.8607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0223 2.0173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7922 1.3791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8133 -0.1252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5826 -2.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1244 -0.4728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6244 -1.3388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0139 6.2512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2112 1.4989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1901 3.0031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4174 -2.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6244 -1.3388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5797 3.6414 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5826 -4.4443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0826 -3.5783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4174 -0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9174 -1.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8516 -0.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3513 -1.0378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3756 0.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3756 -1.3388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6244 0.3933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8756 -0.4728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5173 3.2938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0826 -5.3103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0826 -3.5783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9174 -1.8462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8404 -0.4924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7167 -1.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8756 1.2593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 36 1 0 0 0 0 9 36 1 0 0 0 0 10 13 1 0 0 0 0 10 22 2 0 0 0 0 11 14 1 0 0 0 0 11 23 2 0 0 0 0 12 15 2 0 0 0 0 12 26 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 18 1 0 0 0 0 17 25 2 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 27 1 0 0 0 0 21 37 1 0 0 0 0 25 28 1 0 0 0 0 26 32 1 0 0 0 0 27 13 1 6 0 0 0 27 36 1 0 0 0 0 28 39 1 6 0 0 0 29 30 2 0 0 0 0 29 40 1 0 0 0 0 30 41 1 0 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 31 34 1 0 0 0 0 32 42 2 0 0 0 0 33 37 1 0 0 0 0 33 43 1 0 0 0 0 34 38 1 0 0 0 0 34 44 2 0 0 0 0 35 37 1 0 0 0 0 35 38 1 0 0 0 0 35 45 2 0 0 0 0 36 38 1 0 0 0 0 37 18 1 1 0 0 0 38 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.36
Volume:	672.665
LogP:	7.021
LogD:	4.623
LogS:	-3.938
# Rotatable Bonds:	11
TPSA:	128.97
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.102
Synthetic Accessibility Score:	5.826
Fsp3:	0.526
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111
MDCK Permeability:	1.7968164684134535e-05
Pgp-inhibitor:	0.128
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.336
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.759

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	97.77465057373047%
Volume Distribution (VD):	1.576
Pgp-substrate:	4.909631252288818%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.672
CYP2C19-substrate:	0.441
CYP2C9-inhibitor:	0.803
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.762
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.756

ADMET: Excretion

Clearance (CL):	14.477
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.539
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.058
Carcinogencity:	0.538
Eye Corrosion:	0.022
Eye Irritation:	0.219
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC30846

Natural Product ID:	NPC30846
*Common Name:**	ONKOOMBIYOLKEL-MCDUMTBSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ONKOOMBIYOLKEL-MCDUMTBSSA-N
Standard InCHI:	InChI=1S/C38H50O7/c1-22(2)10-13-27-21-37(18-17-25(7)28(39)14-11-23(3)4)33(43)31(32(42)26-12-15-29(40)30(41)20-26)34(44)38(35(37)45,36(27,8)9)19-16-24(5)6/h10-12,15-17,20,27-28,39-41,43H,13-14,18-19,21H2,1-9H3/b25-17+/t27-,28+,37+,38-/m1/s1
SMILES:	CC(=CC[C@@H]1C[C@@]2(C/C=C(/[C@H](CC=C(C)C)O)C)C(=C(C(=O)[C@@](C1(C)C)(C2=O)CC=C(C)C)C(=O)c1ccc(c(c1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1629875
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	seeds and rinds	n.a.	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21028890]
NPO3858	Pimpinella magna	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1970	Rubus palmatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6556	Garcinia intermedia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO104	Hymenodictyon floribundum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4768	Lunaria annua	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3858	Pimpinella magna	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10493	Casearia thwaitesii	Species	Salicaceae	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
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	38320.0	nM	PMID[515050]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45580.0	nM	PMID[515050]

☑ 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 NPC30846 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	344
0.1-0.2	1299
0.2-0.3	2604
0.3-0.4	6853
0.4-0.5	11085
0.5-0.6	7235
0.6-0.7	10124
0.7-0.8	3016
0.8-0.85	71
0.85-0.9	15
0.9-0.95	17
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471972
1.0	High Similarity	NPC471971
1.0	High Similarity	NPC469855
0.9854	High Similarity	NPC469854
0.9854	High Similarity	NPC469856
0.9712	High Similarity	NPC471970
0.9704	High Similarity	NPC5014
0.9704	High Similarity	NPC165191
0.9704	High Similarity	NPC149773
0.9704	High Similarity	NPC50615
0.9704	High Similarity	NPC114333
0.9704	High Similarity	NPC469857
0.9704	High Similarity	NPC91887
0.9704	High Similarity	NPC473479
0.9704	High Similarity	NPC473779
0.9704	High Similarity	NPC46242
0.9704	High Similarity	NPC42384
0.9704	High Similarity	NPC157284
0.9704	High Similarity	NPC23667
0.9704	High Similarity	NPC477849
0.9704	High Similarity	NPC28592
0.9704	High Similarity	NPC297797
0.9704	High Similarity	NPC245760
0.9704	High Similarity	NPC289358
0.9704	High Similarity	NPC51531
0.9632	High Similarity	NPC294330
0.9562	High Similarity	NPC473527
0.9556	High Similarity	NPC7464
0.9437	High Similarity	NPC46549
0.9437	High Similarity	NPC132810
0.9437	High Similarity	NPC264229
0.9296	High Similarity	NPC273798
0.9291	High Similarity	NPC469375
0.9291	High Similarity	NPC8493
0.9291	High Similarity	NPC294679
0.9291	High Similarity	NPC144247
0.9291	High Similarity	NPC145301
0.9275	High Similarity	NPC469681
0.9275	High Similarity	NPC471974
0.9275	High Similarity	NPC469680
0.9103	High Similarity	NPC237441
0.9037	High Similarity	NPC25736
0.8859	High Similarity	NPC305710
0.8784	High Similarity	NPC48949
0.8643	High Similarity	NPC4170
0.8643	High Similarity	NPC474715
0.8643	High Similarity	NPC138472
0.8621	High Similarity	NPC248068
0.8611	High Similarity	NPC471853
0.8562	High Similarity	NPC199936
0.8531	High Similarity	NPC277559
0.8531	High Similarity	NPC118366
0.8531	High Similarity	NPC475957
0.8511	High Similarity	NPC111845
0.8483	Intermediate Similarity	NPC470035
0.8483	Intermediate Similarity	NPC476534
0.8472	Intermediate Similarity	NPC230811
0.8446	Intermediate Similarity	NPC470038
0.8429	Intermediate Similarity	NPC117609
0.8417	Intermediate Similarity	NPC234175
0.8403	Intermediate Similarity	NPC49911
0.8403	Intermediate Similarity	NPC471152
0.8392	Intermediate Similarity	NPC43353
0.8392	Intermediate Similarity	NPC153088
0.8389	Intermediate Similarity	NPC143685
0.8382	Intermediate Similarity	NPC86900
0.838	Intermediate Similarity	NPC294226
0.8377	Intermediate Similarity	NPC471968
0.8367	Intermediate Similarity	NPC184935
0.8322	Intermediate Similarity	NPC202225
0.8322	Intermediate Similarity	NPC258856
0.8289	Intermediate Similarity	NPC470037
0.8273	Intermediate Similarity	NPC71610
0.8272	Intermediate Similarity	NPC471969
0.8264	Intermediate Similarity	NPC258502
0.8255	Intermediate Similarity	NPC79627
0.8252	Intermediate Similarity	NPC78307
0.8252	Intermediate Similarity	NPC477139
0.8243	Intermediate Similarity	NPC176030
0.8243	Intermediate Similarity	NPC229218
0.8243	Intermediate Similarity	NPC469447
0.8243	Intermediate Similarity	NPC169214
0.8243	Intermediate Similarity	NPC477873
0.8243	Intermediate Similarity	NPC141817
0.8243	Intermediate Similarity	NPC192597
0.8239	Intermediate Similarity	NPC471851
0.8219	Intermediate Similarity	NPC416
0.8219	Intermediate Similarity	NPC61398
0.8214	Intermediate Similarity	NPC72667
0.8212	Intermediate Similarity	NPC52692
0.8212	Intermediate Similarity	NPC10842
0.82	Intermediate Similarity	NPC75295
0.8188	Intermediate Similarity	NPC239608
0.8188	Intermediate Similarity	NPC46161
0.8162	Intermediate Similarity	NPC265454
0.8162	Intermediate Similarity	NPC34634
0.8151	Intermediate Similarity	NPC264022
0.8143	Intermediate Similarity	NPC254492
0.8143	Intermediate Similarity	NPC15837
0.8138	Intermediate Similarity	NPC72918
0.8133	Intermediate Similarity	NPC53520
0.8125	Intermediate Similarity	NPC475457
0.8125	Intermediate Similarity	NPC18982
0.8125	Intermediate Similarity	NPC475627
0.8125	Intermediate Similarity	NPC475346
0.8121	Intermediate Similarity	NPC291078
0.8121	Intermediate Similarity	NPC477209
0.8112	Intermediate Similarity	NPC291001
0.8102	Intermediate Similarity	NPC98305
0.8099	Intermediate Similarity	NPC171460
0.8095	Intermediate Similarity	NPC206207
0.8092	Intermediate Similarity	NPC476821
0.8085	Intermediate Similarity	NPC69424
0.8085	Intermediate Similarity	NPC78364
0.8085	Intermediate Similarity	NPC176130
0.8085	Intermediate Similarity	NPC84672
0.8085	Intermediate Similarity	NPC324209
0.8082	Intermediate Similarity	NPC315275
0.8082	Intermediate Similarity	NPC474311
0.8074	Intermediate Similarity	NPC150919
0.8069	Intermediate Similarity	NPC204582
0.8069	Intermediate Similarity	NPC471913
0.8067	Intermediate Similarity	NPC209085
0.8067	Intermediate Similarity	NPC224884
0.8054	Intermediate Similarity	NPC472904
0.8052	Intermediate Similarity	NPC475311
0.8052	Intermediate Similarity	NPC473680
0.8052	Intermediate Similarity	NPC473579
0.8052	Intermediate Similarity	NPC475454
0.805	Intermediate Similarity	NPC266365
0.8042	Intermediate Similarity	NPC108129
0.8041	Intermediate Similarity	NPC472903
0.8028	Intermediate Similarity	NPC96024
0.8028	Intermediate Similarity	NPC247250
0.8028	Intermediate Similarity	NPC3009
0.8028	Intermediate Similarity	NPC767
0.8027	Intermediate Similarity	NPC147418
0.8027	Intermediate Similarity	NPC290030
0.8026	Intermediate Similarity	NPC476535
0.8025	Intermediate Similarity	NPC471975
0.8025	Intermediate Similarity	NPC470374
0.8025	Intermediate Similarity	NPC478059
0.8025	Intermediate Similarity	NPC478060
0.8025	Intermediate Similarity	NPC470377
0.8015	Intermediate Similarity	NPC249435
0.8014	Intermediate Similarity	NPC103082
0.8013	Intermediate Similarity	NPC309169
0.8013	Intermediate Similarity	NPC62051
0.8013	Intermediate Similarity	NPC196941
0.8	Intermediate Similarity	NPC144283
0.8	Intermediate Similarity	NPC199273
0.8	Intermediate Similarity	NPC234890
0.8	Intermediate Similarity	NPC52407
0.8	Intermediate Similarity	NPC15127
0.8	Intermediate Similarity	NPC471749
0.8	Intermediate Similarity	NPC74507
0.8	Intermediate Similarity	NPC53896
0.7987	Intermediate Similarity	NPC474310
0.7987	Intermediate Similarity	NPC78987
0.7987	Intermediate Similarity	NPC203063
0.7987	Intermediate Similarity	NPC304110
0.7987	Intermediate Similarity	NPC82336
0.7987	Intermediate Similarity	NPC27518
0.7986	Intermediate Similarity	NPC91478
0.7973	Intermediate Similarity	NPC182249
0.7973	Intermediate Similarity	NPC87723
0.7973	Intermediate Similarity	NPC141368
0.7972	Intermediate Similarity	NPC117899
0.7972	Intermediate Similarity	NPC276238
0.7972	Intermediate Similarity	NPC474546
0.7971	Intermediate Similarity	NPC236520
0.7971	Intermediate Similarity	NPC294361
0.7962	Intermediate Similarity	NPC472807
0.7961	Intermediate Similarity	NPC8102
0.7961	Intermediate Similarity	NPC73416
0.7961	Intermediate Similarity	NPC66894
0.7961	Intermediate Similarity	NPC160777
0.7959	Intermediate Similarity	NPC65005
0.7959	Intermediate Similarity	NPC194764
0.7959	Intermediate Similarity	NPC193358
0.7959	Intermediate Similarity	NPC264112
0.7958	Intermediate Similarity	NPC471530
0.7958	Intermediate Similarity	NPC316553
0.7958	Intermediate Similarity	NPC473787
0.795	Intermediate Similarity	NPC100420
0.7949	Intermediate Similarity	NPC164912
0.7947	Intermediate Similarity	NPC25491
0.7945	Intermediate Similarity	NPC50924
0.7945	Intermediate Similarity	NPC194970
0.7935	Intermediate Similarity	NPC118033
0.7935	Intermediate Similarity	NPC474191
0.7933	Intermediate Similarity	NPC472410
0.7933	Intermediate Similarity	NPC84273
0.7931	Intermediate Similarity	NPC246693
0.7931	Intermediate Similarity	NPC242358
0.7931	Intermediate Similarity	NPC50763
0.7931	Intermediate Similarity	NPC110609
0.7929	Intermediate Similarity	NPC198014
0.7927	Intermediate Similarity	NPC472803
0.7922	Intermediate Similarity	NPC474903

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 NPC30846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	876
0.2-0.3	1469
0.3-0.4	2737
0.4-0.5	2184
0.5-0.6	1129
0.6-0.7	410
0.7-0.8	41
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
0.8299	Intermediate Similarity	NPD8166	Discontinued
0.7808	Intermediate Similarity	NPD943	Approved
0.777	Intermediate Similarity	NPD2932	Approved
0.7727	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3019	Approved
0.7569	Intermediate Similarity	NPD1470	Approved
0.7483	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1201	Approved
0.7383	Intermediate Similarity	NPD6663	Approved
0.7372	Intermediate Similarity	NPD3300	Phase 2
0.7357	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4628	Phase 3
0.7353	Intermediate Similarity	NPD3021	Approved
0.7353	Intermediate Similarity	NPD3022	Approved
0.7347	Intermediate Similarity	NPD5736	Approved
0.7347	Intermediate Similarity	NPD9494	Approved
0.7324	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3092	Approved
0.7284	Intermediate Similarity	NPD1934	Approved
0.7255	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3091	Approved
0.7241	Intermediate Similarity	NPD3972	Approved
0.7222	Intermediate Similarity	NPD3026	Approved
0.7222	Intermediate Similarity	NPD3023	Approved
0.7219	Intermediate Similarity	NPD7473	Discontinued
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3094	Phase 2
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.7203	Intermediate Similarity	NPD3025	Approved
0.7203	Intermediate Similarity	NPD3024	Approved
0.72	Intermediate Similarity	NPD8434	Phase 2
0.7197	Intermediate Similarity	NPD6190	Approved
0.7195	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7134	Intermediate Similarity	NPD2801	Approved
0.7125	Intermediate Similarity	NPD6273	Approved
0.7123	Intermediate Similarity	NPD9269	Phase 2
0.7107	Intermediate Similarity	NPD7390	Discontinued
0.7105	Intermediate Similarity	NPD3620	Phase 2
0.7105	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8150	Discontinued
0.7097	Intermediate Similarity	NPD5406	Approved
0.7097	Intermediate Similarity	NPD5405	Approved
0.7097	Intermediate Similarity	NPD5404	Approved
0.7097	Intermediate Similarity	NPD5408	Approved
0.7089	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3818	Discontinued
0.7059	Intermediate Similarity	NPD6166	Phase 2
0.7059	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4380	Phase 2
0.705	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6232	Discontinued
0.7034	Intermediate Similarity	NPD3095	Discontinued
0.703	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD1511	Approved
0.6994	Remote Similarity	NPD7074	Phase 3
0.6987	Remote Similarity	NPD2935	Discontinued
0.6982	Remote Similarity	NPD8127	Discontinued
0.6962	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7028	Phase 2
0.6946	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2344	Approved
0.6937	Remote Similarity	NPD7236	Approved
0.6936	Remote Similarity	NPD7054	Approved
0.6923	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD5494	Approved
0.6923	Remote Similarity	NPD1510	Phase 2
0.6918	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7003	Approved
0.6914	Remote Similarity	NPD7685	Pre-registration
0.6914	Remote Similarity	NPD1512	Approved
0.6906	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7075	Discontinued
0.6897	Remote Similarity	NPD7472	Approved
0.689	Remote Similarity	NPD3226	Approved
0.689	Remote Similarity	NPD3455	Phase 2
0.6875	Remote Similarity	NPD4954	Approved
0.6875	Remote Similarity	NPD4955	Approved
0.6875	Remote Similarity	NPD5034	Approved
0.6875	Remote Similarity	NPD36	Approved
0.6875	Remote Similarity	NPD5026	Approved
0.6875	Remote Similarity	NPD5028	Approved
0.6867	Remote Similarity	NPD1164	Approved
0.6863	Remote Similarity	NPD3764	Approved
0.6853	Remote Similarity	NPD5951	Approved
0.6853	Remote Similarity	NPD2629	Approved
0.6849	Remote Similarity	NPD9268	Approved
0.6839	Remote Similarity	NPD5844	Phase 1
0.6836	Remote Similarity	NPD5035	Approved
0.6836	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2346	Discontinued
0.6835	Remote Similarity	NPD1471	Phase 3
0.6835	Remote Similarity	NPD7266	Discontinued
0.6826	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2798	Approved
0.6818	Remote Similarity	NPD5030	Phase 2
0.6818	Remote Similarity	NPD7251	Discontinued
0.6813	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4110	Phase 3
0.68	Remote Similarity	NPD1876	Approved
0.6795	Remote Similarity	NPD6651	Approved
0.6795	Remote Similarity	NPD1607	Approved
0.6792	Remote Similarity	NPD1549	Phase 2
0.6781	Remote Similarity	NPD9545	Approved
0.678	Remote Similarity	NPD7808	Phase 3
0.6774	Remote Similarity	NPD1240	Approved
0.677	Remote Similarity	NPD2309	Approved
0.6761	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6797	Phase 2
0.6758	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6599	Discontinued
0.6742	Remote Similarity	NPD8312	Approved
0.6742	Remote Similarity	NPD8313	Approved
0.6739	Remote Similarity	NPD1237	Approved
0.6733	Remote Similarity	NPD1755	Approved
0.673	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7239	Suspended
0.6726	Remote Similarity	NPD5760	Phase 2
0.6726	Remote Similarity	NPD5761	Phase 2
0.6722	Remote Similarity	NPD5038	Approved
0.6722	Remote Similarity	NPD5037	Approved
0.6714	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5536	Phase 2
0.671	Remote Similarity	NPD8032	Phase 2
0.6707	Remote Similarity	NPD7411	Suspended
0.6706	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3020	Approved
0.6689	Remote Similarity	NPD1283	Approved
0.6689	Remote Similarity	NPD4059	Approved
0.6689	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6959	Discontinued
0.6686	Remote Similarity	NPD3817	Phase 2
0.6685	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD5036	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6100	Approved
0.6648	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2800	Approved
0.6646	Remote Similarity	NPD2534	Approved
0.6646	Remote Similarity	NPD2532	Approved
0.6646	Remote Similarity	NPD2533	Approved
0.6629	Remote Similarity	NPD8368	Discontinued
0.6624	Remote Similarity	NPD5735	Approved
0.6622	Remote Similarity	NPD1651	Approved
0.6607	Remote Similarity	NPD6873	Phase 2
0.6605	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7742	Approved
0.6604	Remote Similarity	NPD7743	Approved
0.6601	Remote Similarity	NPD257	Approved
0.6601	Remote Similarity	NPD258	Approved
0.66	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7610	Discontinued
0.6596	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7228	Approved
0.6588	Remote Similarity	NPD5978	Approved
0.6588	Remote Similarity	NPD5977	Approved
0.6588	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3027	Phase 3
0.6581	Remote Similarity	NPD7008	Discontinued
0.6566	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD9570	Approved
0.6561	Remote Similarity	NPD4140	Approved
0.655	Remote Similarity	NPD4967	Phase 2
0.655	Remote Similarity	NPD4966	Approved
0.655	Remote Similarity	NPD4965	Approved
0.655	Remote Similarity	NPD7768	Phase 2
0.6545	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3645	Discontinued
0.6538	Remote Similarity	NPD3268	Approved
0.6538	Remote Similarity	NPD2313	Discontinued
0.6536	Remote Similarity	NPD5029	Approved
0.6536	Remote Similarity	NPD5027	Approved
0.6536	Remote Similarity	NPD5031	Approved
0.6536	Remote Similarity	NPD6559	Discontinued
0.6531	Remote Similarity	NPD9493	Approved
0.6529	Remote Similarity	NPD1465	Phase 2
0.6528	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6355	Discontinued

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