NPASS Compound

Structure

CID6975 OpenBabel06191715332D 43 45 0 0 1 0 0 0 0 0999 V2000 -1.3900 -3.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0613 0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1953 2.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3900 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5240 -3.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7934 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7934 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9273 -0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2750 0.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9273 -2.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0613 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4460 1.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9994 0.0349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1953 -2.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 -4.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1953 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5240 -2.4397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0613 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3293 -1.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8356 -3.3794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3420 0.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8204 2.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3293 0.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3420 -1.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6865 -2.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 -3.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 1.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6713 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 2.2057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6713 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8204 -3.2057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6865 1.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 -2.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 -4.8794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1625 3.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3293 -3.4718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 -4.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3420 2.4718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6561 0.1736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 -1.1736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 13 36 1 0 0 0 0 14 19 1 0 0 0 0 15 23 1 0 0 0 0 15 31 1 0 0 0 0 16 37 1 0 0 0 0 18 4 1 6 0 0 0 20 14 1 1 0 0 0 20 26 1 0 0 0 0 20 32 1 0 0 0 0 21 16 1 1 0 0 0 21 27 1 0 0 0 0 21 33 1 0 0 0 0 22 12 1 1 0 0 0 22 28 1 0 0 0 0 22 36 1 0 0 0 0 23 34 2 3 0 0 0 23 38 1 0 0 0 0 24 17 1 1 0 0 0 24 29 1 0 0 0 0 24 34 1 0 0 0 0 25 18 1 1 0 0 0 25 30 1 0 0 0 0 25 35 1 0 0 0 0 26 33 2 3 0 0 0 26 39 1 0 0 0 0 27 35 2 3 0 0 0 27 40 1 0 0 0 0 28 31 2 3 0 0 0 28 41 1 0 0 0 0 29 32 2 3 0 0 0 29 42 1 0 0 0 0 30 36 1 0 0 0 0 30 43 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.33
Volume:	605.551
LogP:	0.585
LogD:	1.648
LogS:	-2.969
# Rotatable Bonds:	6
TPSA:	186.04
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	4.796
Fsp3:	0.6
Lipinski Rule-of-5:	Rejected
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:	-6.516
MDCK Permeability:	2.9645912945852615e-05
Pgp-inhibitor:	0.317
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.651
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	57.561378479003906%
Volume Distribution (VD):	0.357
Pgp-substrate:	37.228240966796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	4.159
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.502
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.621
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.12
Carcinogencity:	0.07
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC6975

Natural Product ID:	NPC6975
*Common Name:**	Dianthin E
IUPAC Name:	(3S,6S,9S,12S,18S)-9-benzyl-3-[(2S)-butan-2-yl]-6-(hydroxymethyl)-12-propan-2-yl-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosane-2,5,8,11,14,17-hexone
Synonyms:	Dianthin E
Standard InCHIKey:	NHNDCMROOPKDNF-BYZHJWIBSA-N
Standard InCHI:	InChI=1S/C30H44N6O7/c1-5-18(4)25-30(43)36-13-9-12-22(36)28(41)31-15-23(38)34-24(17(2)3)29(42)32-20(14-19-10-7-6-8-11-19)26(39)33-21(16-37)27(40)35-25/h6-8,10-11,17-18,20-22,24-25,37H,5,9,12-16H2,1-4H3,(H,31,41)(H,32,42)(H,33,39)(H,34,38)(H,35,40)/t18-,20-,21-,22-,24-,25-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=NCC(=N[C@@H](C(C)C)C(=N[C@@H](Cc2ccccc2)C(=N[C@@H](CO)C(=N1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1957467
PubChem CID:	21589729
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387653]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22325941]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	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
Others	5

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown	Activity	=	10.3	%	PMID[492896]
NPT610	Others	Molecular identity unknown	Activity	=	19.5	%	PMID[492896]
NPT610	Others	Molecular identity unknown	Activity	=	14.9	%	PMID[492896]
NPT610	Others	Molecular identity unknown	Activity	=	31.3	%	PMID[492896]

☑ 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 NPC6975 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	100
0.1-0.2	658
0.2-0.3	3589
0.3-0.4	21113
0.4-0.5	13706
0.5-0.6	2525
0.6-0.7	598
0.7-0.8	276
0.8-0.85	88
0.85-0.9	35
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9826	High Similarity	NPC202521
0.9739	High Similarity	NPC476990
0.9573	High Similarity	NPC252878
0.9492	High Similarity	NPC46427
0.9426	High Similarity	NPC130309
0.9237	High Similarity	NPC200964
0.8983	High Similarity	NPC470545
0.8968	High Similarity	NPC287401
0.8908	High Similarity	NPC470546
0.8898	High Similarity	NPC470544
0.881	High Similarity	NPC255447
0.876	High Similarity	NPC471265
0.876	High Similarity	NPC471264
0.875	High Similarity	NPC248283
0.873	High Similarity	NPC300315
0.872	High Similarity	NPC319766
0.8712	High Similarity	NPC476978
0.8651	High Similarity	NPC473322
0.8583	High Similarity	NPC315276
0.8583	High Similarity	NPC14672
0.8583	High Similarity	NPC200589
0.8583	High Similarity	NPC285926
0.8548	High Similarity	NPC175726
0.8548	High Similarity	NPC474082
0.8507	High Similarity	NPC315266
0.8507	High Similarity	NPC5620
0.8485	Intermediate Similarity	NPC163392
0.8485	Intermediate Similarity	NPC239762
0.8462	Intermediate Similarity	NPC141050
0.8444	Intermediate Similarity	NPC314358
0.843	Intermediate Similarity	NPC239357
0.8417	Intermediate Similarity	NPC33742
0.8413	Intermediate Similarity	NPC101719
0.8409	Intermediate Similarity	NPC92784
0.8409	Intermediate Similarity	NPC476133
0.8409	Intermediate Similarity	NPC178662
0.8409	Intermediate Similarity	NPC98424
0.8409	Intermediate Similarity	NPC470884
0.8394	Intermediate Similarity	NPC2501
0.8387	Intermediate Similarity	NPC71684
0.837	Intermediate Similarity	NPC209509
0.837	Intermediate Similarity	NPC313867
0.837	Intermediate Similarity	NPC316008
0.8359	Intermediate Similarity	NPC111428
0.8358	Intermediate Similarity	NPC161069
0.8333	Intermediate Similarity	NPC35850
0.8333	Intermediate Similarity	NPC276949
0.8333	Intermediate Similarity	NPC222466
0.8296	Intermediate Similarity	NPC52748
0.8296	Intermediate Similarity	NPC315283
0.8296	Intermediate Similarity	NPC314388
0.8284	Intermediate Similarity	NPC269398
0.8284	Intermediate Similarity	NPC263493
0.8261	Intermediate Similarity	NPC129666
0.8235	Intermediate Similarity	NPC322878
0.8214	Intermediate Similarity	NPC122590
0.8214	Intermediate Similarity	NPC262166
0.8201	Intermediate Similarity	NPC7817
0.8201	Intermediate Similarity	NPC475168
0.8195	Intermediate Similarity	NPC68865
0.8189	Intermediate Similarity	NPC22746
0.8134	Intermediate Similarity	NPC89489
0.8116	Intermediate Similarity	NPC138775
0.8088	Intermediate Similarity	NPC77905
0.8074	Intermediate Similarity	NPC476259
0.8058	Intermediate Similarity	NPC471820
0.8058	Intermediate Similarity	NPC471821
0.8043	Intermediate Similarity	NPC262077
0.8028	Intermediate Similarity	NPC470902
0.8014	Intermediate Similarity	NPC162104
0.8	Intermediate Similarity	NPC283783
0.7986	Intermediate Similarity	NPC225648
0.7986	Intermediate Similarity	NPC197743
0.7986	Intermediate Similarity	NPC329761
0.7986	Intermediate Similarity	NPC297145
0.7986	Intermediate Similarity	NPC16188
0.7943	Intermediate Similarity	NPC473491
0.7941	Intermediate Similarity	NPC307357
0.7941	Intermediate Similarity	NPC268841
0.7941	Intermediate Similarity	NPC46098
0.7939	Intermediate Similarity	NPC469666
0.7926	Intermediate Similarity	NPC127741
0.7883	Intermediate Similarity	NPC476989
0.7883	Intermediate Similarity	NPC168113
0.7857	Intermediate Similarity	NPC145113
0.7842	Intermediate Similarity	NPC471680
0.7832	Intermediate Similarity	NPC473341
0.7826	Intermediate Similarity	NPC139326
0.7826	Intermediate Similarity	NPC176226
0.7826	Intermediate Similarity	NPC197682
0.7808	Intermediate Similarity	NPC469898
0.7801	Intermediate Similarity	NPC240848
0.7778	Intermediate Similarity	NPC169328
0.7761	Intermediate Similarity	NPC246079
0.7754	Intermediate Similarity	NPC469426
0.7754	Intermediate Similarity	NPC469427
0.7739	Intermediate Similarity	NPC25565
0.7737	Intermediate Similarity	NPC132636
0.7731	Intermediate Similarity	NPC194390
0.7731	Intermediate Similarity	NPC88267
0.7731	Intermediate Similarity	NPC224610
0.7731	Intermediate Similarity	NPC113326
0.773	Intermediate Similarity	NPC135121
0.773	Intermediate Similarity	NPC311658
0.7724	Intermediate Similarity	NPC476268
0.7724	Intermediate Similarity	NPC244509
0.7717	Intermediate Similarity	NPC310467
0.7714	Intermediate Similarity	NPC201244
0.7714	Intermediate Similarity	NPC477217
0.7708	Intermediate Similarity	NPC261934
0.7708	Intermediate Similarity	NPC202198
0.7708	Intermediate Similarity	NPC5194
0.7708	Intermediate Similarity	NPC56685
0.7703	Intermediate Similarity	NPC73655
0.7672	Intermediate Similarity	NPC473501
0.7672	Intermediate Similarity	NPC475439
0.7661	Intermediate Similarity	NPC474584
0.7619	Intermediate Similarity	NPC324850
0.7616	Intermediate Similarity	NPC302597
0.7609	Intermediate Similarity	NPC313694
0.7609	Intermediate Similarity	NPC242159
0.7603	Intermediate Similarity	NPC469903
0.7597	Intermediate Similarity	NPC478015
0.7597	Intermediate Similarity	NPC478016
0.7597	Intermediate Similarity	NPC478014
0.7578	Intermediate Similarity	NPC237420
0.7568	Intermediate Similarity	NPC62104
0.7568	Intermediate Similarity	NPC244336
0.7568	Intermediate Similarity	NPC1390
0.7552	Intermediate Similarity	NPC105717
0.7517	Intermediate Similarity	NPC233702
0.7517	Intermediate Similarity	NPC471527
0.7517	Intermediate Similarity	NPC469901
0.7516	Intermediate Similarity	NPC475123
0.7516	Intermediate Similarity	NPC475204
0.75	Intermediate Similarity	NPC325479
0.7462	Intermediate Similarity	NPC45777
0.7462	Intermediate Similarity	NPC477061
0.7459	Intermediate Similarity	NPC327481
0.7451	Intermediate Similarity	NPC473000
0.7447	Intermediate Similarity	NPC468984
0.7444	Intermediate Similarity	NPC47667
0.7442	Intermediate Similarity	NPC314992
0.7434	Intermediate Similarity	NPC254700
0.7419	Intermediate Similarity	NPC137627
0.7417	Intermediate Similarity	NPC471052
0.7417	Intermediate Similarity	NPC471053
0.7417	Intermediate Similarity	NPC471051
0.7415	Intermediate Similarity	NPC473002
0.7413	Intermediate Similarity	NPC81026
0.74	Intermediate Similarity	NPC473003
0.74	Intermediate Similarity	NPC469902
0.7372	Intermediate Similarity	NPC477462
0.7372	Intermediate Similarity	NPC471165
0.7372	Intermediate Similarity	NPC26108
0.7368	Intermediate Similarity	NPC22883
0.7368	Intermediate Similarity	NPC5719
0.7368	Intermediate Similarity	NPC217804
0.7368	Intermediate Similarity	NPC472923
0.7368	Intermediate Similarity	NPC210377
0.7355	Intermediate Similarity	NPC328494
0.7351	Intermediate Similarity	NPC241794
0.7347	Intermediate Similarity	NPC286551
0.7343	Intermediate Similarity	NPC266741
0.7338	Intermediate Similarity	NPC476102
0.7338	Intermediate Similarity	NPC314835
0.7338	Intermediate Similarity	NPC118099
0.7338	Intermediate Similarity	NPC273907
0.7338	Intermediate Similarity	NPC475318
0.7338	Intermediate Similarity	NPC76785
0.7338	Intermediate Similarity	NPC49577
0.7338	Intermediate Similarity	NPC151706
0.7338	Intermediate Similarity	NPC475598
0.7338	Intermediate Similarity	NPC90194
0.7338	Intermediate Similarity	NPC9687
0.7338	Intermediate Similarity	NPC260045
0.7338	Intermediate Similarity	NPC79465
0.7338	Intermediate Similarity	NPC474855
0.7338	Intermediate Similarity	NPC474811
0.7338	Intermediate Similarity	NPC280022
0.7338	Intermediate Similarity	NPC474787
0.7338	Intermediate Similarity	NPC293377
0.7317	Intermediate Similarity	NPC130898
0.7317	Intermediate Similarity	NPC474804
0.7317	Intermediate Similarity	NPC474973
0.7308	Intermediate Similarity	NPC220698
0.7287	Intermediate Similarity	NPC2265
0.7273	Intermediate Similarity	NPC107938
0.7273	Intermediate Similarity	NPC294516
0.7273	Intermediate Similarity	NPC63040
0.7267	Intermediate Similarity	NPC323336
0.7267	Intermediate Similarity	NPC326349
0.7261	Intermediate Similarity	NPC136797
0.726	Intermediate Similarity	NPC254798
0.7259	Intermediate Similarity	NPC477937
0.7255	Intermediate Similarity	NPC63931
0.725	Intermediate Similarity	NPC12730
0.7244	Intermediate Similarity	NPC89831
0.7244	Intermediate Similarity	NPC273814
0.7236	Intermediate Similarity	NPC143516

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 NPC6975 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	92
0.1-0.2	304
0.2-0.3	649
0.3-0.4	2116
0.4-0.5	3803
0.5-0.6	1690
0.6-0.7	392
0.7-0.8	94
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD8173	Phase 2
0.8906	High Similarity	NPD8172	Phase 2
0.8682	High Similarity	NPD7113	Clinical (unspecified phase)
0.8571	High Similarity	NPD5339	Clinical (unspecified phase)
0.8548	High Similarity	NPD2584	Suspended
0.8492	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD4125	Approved
0.8209	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8416	Discontinued
0.8182	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD3071	Approved
0.7969	Intermediate Similarity	NPD3072	Approved
0.7969	Intermediate Similarity	NPD3073	Approved
0.7939	Intermediate Similarity	NPD4177	Approved
0.7939	Intermediate Similarity	NPD4175	Approved
0.7899	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4761	Approved
0.7891	Intermediate Similarity	NPD4762	Approved
0.7857	Intermediate Similarity	NPD8323	Discontinued
0.7826	Intermediate Similarity	NPD8076	Discontinued
0.782	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD3626	Phase 3
0.7794	Intermediate Similarity	NPD6073	Approved
0.7794	Intermediate Similarity	NPD5725	Approved
0.7744	Intermediate Similarity	NPD5263	Approved
0.7744	Intermediate Similarity	NPD4676	Approved
0.774	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD6901	Phase 3
0.7727	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD8643	Discontinued
0.7639	Intermediate Similarity	NPD7613	Discontinued
0.763	Intermediate Similarity	NPD1330	Phase 2
0.763	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7130	Phase 3
0.7594	Intermediate Similarity	NPD3588	Discontinued
0.7576	Intermediate Similarity	NPD3125	Approved
0.7574	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5747	Discontinued
0.7571	Intermediate Similarity	NPD2022	Approved
0.7559	Intermediate Similarity	NPD3123	Discovery
0.7556	Intermediate Similarity	NPD2046	Approved
0.7556	Intermediate Similarity	NPD2044	Approved
0.7556	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD21	Approved
0.7556	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2048	Approved
0.7556	Intermediate Similarity	NPD2047	Approved
0.7556	Intermediate Similarity	NPD2051	Approved
0.7556	Intermediate Similarity	NPD2043	Approved
0.7556	Intermediate Similarity	NPD2045	Approved
0.7552	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7342	Discontinued
0.7447	Intermediate Similarity	NPD2088	Approved
0.7447	Intermediate Similarity	NPD2087	Approved
0.7444	Intermediate Similarity	NPD6792	Phase 3
0.7444	Intermediate Similarity	NPD5367	Discontinued
0.7442	Intermediate Similarity	NPD2218	Phase 2
0.7442	Intermediate Similarity	NPD2217	Approved
0.7432	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD8315	Phase 1
0.7407	Intermediate Similarity	NPD3040	Approved
0.7407	Intermediate Similarity	NPD5759	Approved
0.7394	Intermediate Similarity	NPD2436	Approved
0.7394	Intermediate Similarity	NPD2437	Approved
0.7391	Intermediate Similarity	NPD5323	Approved
0.7391	Intermediate Similarity	NPD4153	Approved
0.7379	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD999	Phase 2
0.7368	Intermediate Similarity	NPD4677	Discontinued
0.7364	Intermediate Similarity	NPD7522	Discontinued
0.7338	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7720	Phase 2
0.7319	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3480	Approved
0.7299	Intermediate Similarity	NPD4794	Discontinued
0.7273	Intermediate Similarity	NPD6681	Discovery
0.7266	Intermediate Similarity	NPD8265	Approved
0.7266	Intermediate Similarity	NPD6623	Phase 3
0.726	Intermediate Similarity	NPD3988	Approved
0.726	Intermediate Similarity	NPD5613	Approved
0.726	Intermediate Similarity	NPD5614	Approved
0.726	Intermediate Similarity	NPD3987	Approved
0.7254	Intermediate Similarity	NPD7511	Approved
0.7254	Intermediate Similarity	NPD7512	Approved
0.7252	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5299	Approved
0.7234	Intermediate Similarity	NPD4126	Approved
0.7234	Intermediate Similarity	NPD6852	Discontinued
0.7222	Intermediate Similarity	NPD5264	Approved
0.7222	Intermediate Similarity	NPD5265	Approved
0.7222	Intermediate Similarity	NPD3643	Approved
0.7222	Intermediate Similarity	NPD3642	Approved
0.7222	Intermediate Similarity	NPD3644	Approved
0.7208	Intermediate Similarity	NPD8303	Discontinued
0.7194	Intermediate Similarity	NPD941	Approved
0.719	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2031	Discontinued
0.7181	Intermediate Similarity	NPD4648	Approved
0.7181	Intermediate Similarity	NPD4646	Approved
0.7181	Intermediate Similarity	NPD4647	Approved
0.7172	Intermediate Similarity	NPD6676	Phase 2
0.7162	Intermediate Similarity	NPD5229	Approved
0.7162	Intermediate Similarity	NPD5230	Approved
0.7162	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6088	Approved
0.7143	Intermediate Similarity	NPD5296	Approved
0.7123	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD480	Approved
0.7105	Intermediate Similarity	NPD7011	Discontinued
0.7089	Intermediate Similarity	NPD8124	Phase 3
0.7089	Intermediate Similarity	NPD8126	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4151	Approved
0.7078	Intermediate Similarity	NPD8351	Phase 2
0.7077	Intermediate Similarity	NPD1348	Approved
0.7067	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4814	Discontinued
0.7059	Intermediate Similarity	NPD6325	Discontinued
0.7059	Intermediate Similarity	NPD4557	Approved
0.7054	Intermediate Similarity	NPD3598	Phase 3
0.705	Intermediate Similarity	NPD4738	Phase 2
0.7045	Intermediate Similarity	NPD6343	Approved
0.7045	Intermediate Similarity	NPD6345	Approved
0.7042	Intermediate Similarity	NPD7510	Approved
0.7037	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6690	Approved
0.7023	Intermediate Similarity	NPD1344	Phase 2
0.7014	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5581	Approved
0.6993	Remote Similarity	NPD6295	Approved
0.6993	Remote Similarity	NPD6294	Approved
0.6984	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7965	Phase 2
0.6981	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2613	Approved
0.6974	Remote Similarity	NPD8417	Discontinued
0.6972	Remote Similarity	NPD3908	Approved
0.6963	Remote Similarity	NPD2612	Approved
0.6963	Remote Similarity	NPD2609	Approved
0.6963	Remote Similarity	NPD2608	Approved
0.6963	Remote Similarity	NPD2610	Approved
0.6963	Remote Similarity	NPD2611	Approved
0.6963	Remote Similarity	NPD4215	Approved
0.6963	Remote Similarity	NPD4218	Approved
0.6963	Remote Similarity	NPD4217	Approved
0.6963	Remote Similarity	NPD3131	Approved
0.6963	Remote Similarity	NPD3132	Approved
0.6963	Remote Similarity	NPD4216	Approved
0.696	Remote Similarity	NPD1040	Phase 2
0.6948	Remote Similarity	NPD7599	Phase 2
0.6947	Remote Similarity	NPD7508	Discontinued
0.6939	Remote Similarity	NPD1967	Approved
0.6939	Remote Similarity	NPD1968	Approved
0.6929	Remote Similarity	NPD3136	Phase 2
0.6903	Remote Similarity	NPD7600	Phase 2
0.6899	Remote Similarity	NPD7485	Phase 3
0.6899	Remote Similarity	NPD7484	Phase 3
0.6894	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1812	Approved
0.6891	Remote Similarity	NPD1814	Approved
0.6887	Remote Similarity	NPD7131	Phase 3
0.6875	Remote Similarity	NPD3581	Discontinued
0.687	Remote Similarity	NPD747	Discontinued
0.6866	Remote Similarity	NPD5981	Approved
0.6857	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD854	Approved
0.6855	Remote Similarity	NPD855	Approved
0.6853	Remote Similarity	NPD3577	Discontinued
0.6846	Remote Similarity	NPD4165	Phase 2
0.6846	Remote Similarity	NPD3066	Phase 2
0.6842	Remote Similarity	NPD5991	Approved
0.6842	Remote Similarity	NPD5990	Approved
0.6839	Remote Similarity	NPD4567	Approved
0.6839	Remote Similarity	NPD4566	Approved
0.6838	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1080	Approved
0.6831	Remote Similarity	NPD2570	Approved
0.6831	Remote Similarity	NPD2573	Approved
0.6831	Remote Similarity	NPD3615	Approved
0.6831	Remote Similarity	NPD3087	Approved
0.6831	Remote Similarity	NPD3090	Approved
0.6831	Remote Similarity	NPD3614	Approved
0.6831	Remote Similarity	NPD3089	Approved
0.6831	Remote Similarity	NPD2571	Approved
0.6831	Remote Similarity	NPD4746	Phase 3
0.6831	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3616	Approved
0.6831	Remote Similarity	NPD2566	Approved
0.6831	Remote Similarity	NPD4745	Approved
0.6831	Remote Similarity	NPD2574	Discontinued
0.6831	Remote Similarity	NPD3088	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