NPASS Compound

Structure

NPC476133 OpenBabel07101719132D 48 50 0 0 1 0 0 0 0 0999 V2000 0.4536 -6.7002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4794 -8.0958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4125 0.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4383 -0.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8456 1.9868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1162 2.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2030 -3.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5698 0.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2504 1.2446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8258 -1.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9598 -2.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8258 -0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0938 -1.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9598 -0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6140 -4.4276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3852 -5.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1140 -3.5615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4325 -5.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1751 -6.5096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2278 -0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3694 -7.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5225 -0.1051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9534 1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3907 -4.1823 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0938 -0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3617 -0.9775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0651 -5.5157 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.1401 -5.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7168 -0.6973 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8983 0.5368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4414 -3.8680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1683 -1.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7399 -2.9136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7260 -0.2056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0274 -5.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9044 0.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3057 -2.5801 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7124 -1.9140 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 2.8741 0.3181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8492 -4.6738 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3835 -5.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1227 -1.2910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7304 -3.0510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3828 0.5485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4542 -6.1480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6323 1.3890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0666 -5.4606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 39 1 0 0 0 0 9 40 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 25 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 37 1 0 0 0 0 18 41 1 0 0 0 0 19 21 1 0 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 24 31 1 0 0 0 0 26 20 1 6 0 0 0 26 34 1 0 0 0 0 26 38 1 0 0 0 0 27 35 1 0 0 0 0 27 48 1 0 0 0 0 28 42 2 0 0 0 0 28 48 1 0 0 0 0 29 22 1 6 0 0 0 29 32 1 0 0 0 0 29 39 1 0 0 0 0 30 23 1 6 0 0 0 30 36 1 0 0 0 0 30 40 1 0 0 0 0 31 33 1 6 0 0 0 31 41 1 0 0 0 0 32 37 2 3 0 0 0 32 43 1 0 0 0 0 33 38 2 3 0 0 0 33 44 1 0 0 0 0 34 40 1 0 0 0 0 34 45 2 0 0 0 0 35 41 1 0 0 0 0 35 46 2 0 0 0 0 36 39 1 0 0 0 0 36 47 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	669.41
Volume:	698.33
LogP:	3.359
LogD:	2.601
LogS:	-4.354
# Rotatable Bonds:	6
TPSA:	145.43
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	5.163
Fsp3:	0.667
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:	-5.261
MDCK Permeability:	5.569702261709608e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.565
Human Intestinal Absorption (HIA):	0.649
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.534

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	89.84339141845703%
Volume Distribution (VD):	0.542
Pgp-substrate:	2.3845088481903076%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.195
CYP2C9-substrate:	0.38
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	6.769
Half-life (T1/2):	0.689

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.143
Skin Sensitization:	0.026
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.006

Download Data

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

Natural Product: NPC476133

Natural Product ID:	NPC476133
*Common Name:**	Isaridin C2
IUPAC Name:	(10S,13S,16S,19S)-16-benzyl-11,14,20-trimethyl-3-(2-methylpropyl)-10,13-di(propan-2-yl)-4-oxa-1,8,11,14,17-pentazabicyclo[17.3.0]docosane-2,5,9,12,15,18-hexone
Synonyms:	Isaridin C2
Standard InCHIKey:	LQGNIRWAURPTIG-FVRYWTPYSA-N
Standard InCHI:	InChI=1S/C36H55N5O7/c1-21(2)19-27-35(46)41-18-16-24(7)31(41)33(44)38-26(20-25-13-11-10-12-14-25)34(45)40(9)30(23(5)6)36(47)39(8)29(22(3)4)32(43)37-17-15-28(42)48-27/h10-14,21-24,26-27,29-31H,15-20H2,1-9H3,(H,37,43)(H,38,44)/t24?,26-,27?,29-,30-,31-/m0/s1
SMILES:	CC1CCN2C1C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)NCCC(=O)OC(C2=O)CC(C)C)C(C)C)C)C(C)C)C)CC3=CC=CC=C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL539419
PubChem CID:	16680821
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21438588]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23822585]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO20842	Beauveria felina	Species	Cordycipitaceae	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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12120.0	nM	PMID[497101]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10090.0	nM	PMID[497101]

☑ 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 NPC476133 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	125
0.1-0.2	672
0.2-0.3	3663
0.3-0.4	20989
0.4-0.5	13746
0.5-0.6	2582
0.6-0.7	551
0.7-0.8	254
0.8-0.85	70
0.85-0.9	30
0.9-0.95	5
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470884
1.0	High Similarity	NPC98424
1.0	High Similarity	NPC178662
1.0	High Similarity	NPC92784
0.9624	High Similarity	NPC209509
0.9615	High Similarity	NPC471264
0.9615	High Similarity	NPC471265
0.9545	High Similarity	NPC269398
0.9545	High Similarity	NPC263493
0.9333	High Similarity	NPC5620
0.927	High Similarity	NPC240848
0.913	High Similarity	NPC471820
0.913	High Similarity	NPC471821
0.9065	High Similarity	NPC129666
0.9044	High Similarity	NPC139326
0.8849	High Similarity	NPC262077
0.8841	High Similarity	NPC476978
0.8841	High Similarity	NPC52748
0.8803	High Similarity	NPC162104
0.8786	High Similarity	NPC225648
0.8786	High Similarity	NPC329761
0.8768	High Similarity	NPC161069
0.8759	High Similarity	NPC268841
0.8759	High Similarity	NPC307357
0.8759	High Similarity	NPC46098
0.8759	High Similarity	NPC197743
0.8759	High Similarity	NPC297145
0.875	High Similarity	NPC200964
0.8741	High Similarity	NPC248283
0.8652	High Similarity	NPC145113
0.8613	High Similarity	NPC68865
0.8592	High Similarity	NPC105717
0.8531	High Similarity	NPC2501
0.8521	High Similarity	NPC138775
0.8511	High Similarity	NPC313867
0.8511	High Similarity	NPC316008
0.8489	Intermediate Similarity	NPC163392
0.8489	Intermediate Similarity	NPC239762
0.8451	Intermediate Similarity	NPC314358
0.844	Intermediate Similarity	NPC315283
0.844	Intermediate Similarity	NPC314388
0.8409	Intermediate Similarity	NPC6975
0.8409	Intermediate Similarity	NPC46427
0.8369	Intermediate Similarity	NPC197682
0.8356	Intermediate Similarity	NPC286551
0.8356	Intermediate Similarity	NPC122590
0.8333	Intermediate Similarity	NPC252878
0.8298	Intermediate Similarity	NPC168113
0.8271	Intermediate Similarity	NPC474082
0.8271	Intermediate Similarity	NPC175726
0.8261	Intermediate Similarity	NPC287401
0.8258	Intermediate Similarity	NPC202521
0.8252	Intermediate Similarity	NPC315266
0.8252	Intermediate Similarity	NPC477217
0.8252	Intermediate Similarity	NPC201244
0.8248	Intermediate Similarity	NPC130309
0.8239	Intermediate Similarity	NPC176226
0.8214	Intermediate Similarity	NPC127741
0.8182	Intermediate Similarity	NPC476990
0.8175	Intermediate Similarity	NPC200589
0.8169	Intermediate Similarity	NPC469427
0.8169	Intermediate Similarity	NPC469426
0.8151	Intermediate Similarity	NPC283783
0.8138	Intermediate Similarity	NPC135121
0.8125	Intermediate Similarity	NPC322878
0.8116	Intermediate Similarity	NPC255447
0.8102	Intermediate Similarity	NPC473322
0.8099	Intermediate Similarity	NPC476259
0.8095	Intermediate Similarity	NPC7817
0.8095	Intermediate Similarity	NPC475168
0.8092	Intermediate Similarity	NPC169328
0.803	Intermediate Similarity	NPC310467
0.8029	Intermediate Similarity	NPC89923
0.8029	Intermediate Similarity	NPC239990
0.8029	Intermediate Similarity	NPC152850
0.8029	Intermediate Similarity	NPC71933
0.8029	Intermediate Similarity	NPC105114
0.8029	Intermediate Similarity	NPC319766
0.8015	Intermediate Similarity	NPC285926
0.8015	Intermediate Similarity	NPC315276
0.8015	Intermediate Similarity	NPC14672
0.7975	Intermediate Similarity	NPC317362
0.7975	Intermediate Similarity	NPC317725
0.7975	Intermediate Similarity	NPC326407
0.7975	Intermediate Similarity	NPC318930
0.7956	Intermediate Similarity	NPC136453
0.7933	Intermediate Similarity	NPC470902
0.7929	Intermediate Similarity	NPC246079
0.7908	Intermediate Similarity	NPC469901
0.7895	Intermediate Similarity	NPC470546
0.7883	Intermediate Similarity	NPC101719
0.7879	Intermediate Similarity	NPC239357
0.7867	Intermediate Similarity	NPC473341
0.7857	Intermediate Similarity	NPC157311
0.782	Intermediate Similarity	NPC470545
0.781	Intermediate Similarity	NPC222466
0.7801	Intermediate Similarity	NPC8761
0.7801	Intermediate Similarity	NPC44805
0.7786	Intermediate Similarity	NPC300315
0.7771	Intermediate Similarity	NPC473502
0.7761	Intermediate Similarity	NPC237420
0.775	Intermediate Similarity	NPC477462
0.7744	Intermediate Similarity	NPC470544
0.774	Intermediate Similarity	NPC77905
0.7714	Intermediate Similarity	NPC111428
0.7692	Intermediate Similarity	NPC141050
0.7692	Intermediate Similarity	NPC471051
0.7692	Intermediate Similarity	NPC471052
0.7692	Intermediate Similarity	NPC471053
0.7688	Intermediate Similarity	NPC137627
0.7673	Intermediate Similarity	NPC475204
0.7673	Intermediate Similarity	NPC475123
0.7655	Intermediate Similarity	NPC132636
0.7655	Intermediate Similarity	NPC89489
0.764	Intermediate Similarity	NPC26108
0.7613	Intermediate Similarity	NPC1390
0.7613	Intermediate Similarity	NPC62104
0.7607	Intermediate Similarity	NPC475421
0.7594	Intermediate Similarity	NPC33742
0.7564	Intermediate Similarity	NPC471527
0.7533	Intermediate Similarity	NPC16188
0.7532	Intermediate Similarity	NPC469903
0.7532	Intermediate Similarity	NPC472923
0.7519	Intermediate Similarity	NPC35850
0.7519	Intermediate Similarity	NPC276949
0.7518	Intermediate Similarity	NPC190663
0.75	Intermediate Similarity	NPC47667
0.747	Intermediate Similarity	NPC470112
0.747	Intermediate Similarity	NPC470903
0.747	Intermediate Similarity	NPC167763
0.7467	Intermediate Similarity	NPC81026
0.7464	Intermediate Similarity	NPC71684
0.7453	Intermediate Similarity	NPC196091
0.7453	Intermediate Similarity	NPC40234
0.7444	Intermediate Similarity	NPC273814
0.7429	Intermediate Similarity	NPC22746
0.7423	Intermediate Similarity	NPC471165
0.7423	Intermediate Similarity	NPC476227
0.7421	Intermediate Similarity	NPC217804
0.7421	Intermediate Similarity	NPC210377
0.7421	Intermediate Similarity	NPC22883
0.7421	Intermediate Similarity	NPC5719
0.741	Intermediate Similarity	NPC160493
0.7407	Intermediate Similarity	NPC89831
0.7403	Intermediate Similarity	NPC262166
0.74	Intermediate Similarity	NPC266741
0.7391	Intermediate Similarity	NPC478015
0.7391	Intermediate Similarity	NPC478016
0.7391	Intermediate Similarity	NPC477061
0.7391	Intermediate Similarity	NPC478014
0.7391	Intermediate Similarity	NPC45777
0.7391	Intermediate Similarity	NPC473000
0.7389	Intermediate Similarity	NPC469898
0.7381	Intermediate Similarity	NPC299806
0.7378	Intermediate Similarity	NPC469900
0.7375	Intermediate Similarity	NPC15068
0.7362	Intermediate Similarity	NPC306804
0.7347	Intermediate Similarity	NPC43755
0.7342	Intermediate Similarity	NPC469902
0.7338	Intermediate Similarity	NPC300443
0.7329	Intermediate Similarity	NPC294516
0.7329	Intermediate Similarity	NPC63040
0.7329	Intermediate Similarity	NPC107938
0.7326	Intermediate Similarity	NPC165538
0.7325	Intermediate Similarity	NPC324850
0.7317	Intermediate Similarity	NPC155506
0.7317	Intermediate Similarity	NPC279871
0.7317	Intermediate Similarity	NPC159767
0.7313	Intermediate Similarity	NPC474584
0.7312	Intermediate Similarity	NPC63931
0.7303	Intermediate Similarity	NPC311658
0.729	Intermediate Similarity	NPC202198
0.7285	Intermediate Similarity	NPC471680
0.7279	Intermediate Similarity	NPC197470
0.7273	Intermediate Similarity	NPC473491
0.7267	Intermediate Similarity	NPC254700
0.7266	Intermediate Similarity	NPC80150
0.7244	Intermediate Similarity	NPC473002
0.7244	Intermediate Similarity	NPC39431
0.7239	Intermediate Similarity	NPC46009
0.7226	Intermediate Similarity	NPC233702
0.7209	Intermediate Similarity	NPC475149
0.7209	Intermediate Similarity	NPC471097
0.72	Intermediate Similarity	NPC476989
0.7195	Intermediate Similarity	NPC230611
0.7193	Intermediate Similarity	NPC4910
0.7186	Intermediate Similarity	NPC269750
0.7186	Intermediate Similarity	NPC194671
0.7179	Intermediate Similarity	NPC261934
0.7179	Intermediate Similarity	NPC5194
0.7179	Intermediate Similarity	NPC56685
0.7178	Intermediate Similarity	NPC186617
0.7169	Intermediate Similarity	NPC50016
0.7162	Intermediate Similarity	NPC90194
0.7162	Intermediate Similarity	NPC76785
0.7162	Intermediate Similarity	NPC475318
0.7162	Intermediate Similarity	NPC79465
0.7162	Intermediate Similarity	NPC49577
0.7162	Intermediate Similarity	NPC9687
0.7162	Intermediate Similarity	NPC475598

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 NPC476133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	99
0.1-0.2	308
0.2-0.3	641
0.3-0.4	2335
0.4-0.5	3825
0.5-0.6	1516
0.6-0.7	330
0.7-0.8	90
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8837	High Similarity	NPD2584	Suspended
0.875	High Similarity	NPD8173	Phase 2
0.875	High Similarity	NPD8172	Phase 2
0.8676	High Similarity	NPD7113	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD4177	Approved
0.8102	Intermediate Similarity	NPD4175	Approved
0.8071	Intermediate Similarity	NPD8416	Discontinued
0.7958	Intermediate Similarity	NPD5725	Approved
0.7958	Intermediate Similarity	NPD6073	Approved
0.7956	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD4125	Approved
0.7902	Intermediate Similarity	NPD6901	Phase 3
0.7891	Intermediate Similarity	NPD8323	Discontinued
0.7832	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4153	Approved
0.78	Intermediate Similarity	NPD7613	Discontinued
0.7778	Intermediate Similarity	NPD6852	Discontinued
0.7762	Intermediate Similarity	NPD8643	Discontinued
0.7746	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD3071	Approved
0.7737	Intermediate Similarity	NPD3072	Approved
0.7737	Intermediate Similarity	NPD3073	Approved
0.773	Intermediate Similarity	NPD4794	Discontinued
0.7692	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4762	Approved
0.7664	Intermediate Similarity	NPD4761	Approved
0.7635	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5747	Discontinued
0.7619	Intermediate Similarity	NPD8076	Discontinued
0.7597	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6088	Approved
0.7535	Intermediate Similarity	NPD4676	Approved
0.7535	Intermediate Similarity	NPD5263	Approved
0.7535	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD8417	Discontinued
0.7483	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7965	Phase 2
0.7469	Intermediate Similarity	NPD7964	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD3626	Phase 3
0.7465	Intermediate Similarity	NPD3040	Approved
0.745	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6623	Phase 3
0.7448	Intermediate Similarity	NPD8265	Approved
0.7436	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5265	Approved
0.74	Intermediate Similarity	NPD5264	Approved
0.7394	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD8315	Phase 1
0.7329	Intermediate Similarity	NPD5296	Approved
0.7319	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7512	Approved
0.7315	Intermediate Similarity	NPD7511	Approved
0.731	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1348	Approved
0.7273	Intermediate Similarity	NPD3588	Discontinued
0.7267	Intermediate Similarity	NPD2022	Approved
0.7254	Intermediate Similarity	NPD6792	Phase 3
0.7248	Intermediate Similarity	NPD3480	Approved
0.7244	Intermediate Similarity	NPD4648	Approved
0.7244	Intermediate Similarity	NPD4646	Approved
0.7244	Intermediate Similarity	NPD4647	Approved
0.7241	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2046	Approved
0.7241	Intermediate Similarity	NPD2045	Approved
0.7241	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD21	Approved
0.7241	Intermediate Similarity	NPD2048	Approved
0.7241	Intermediate Similarity	NPD2047	Approved
0.7241	Intermediate Similarity	NPD2051	Approved
0.7241	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2043	Approved
0.7241	Intermediate Similarity	NPD2044	Approved
0.7233	Intermediate Similarity	NPD4557	Approved
0.7222	Intermediate Similarity	NPD5759	Approved
0.7219	Intermediate Similarity	NPD6681	Discovery
0.7219	Intermediate Similarity	NPD2437	Approved
0.7219	Intermediate Similarity	NPD2436	Approved
0.7211	Intermediate Similarity	NPD5323	Approved
0.7208	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1330	Phase 2
0.7192	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4677	Discontinued
0.7181	Intermediate Similarity	NPD6295	Approved
0.7181	Intermediate Similarity	NPD6294	Approved
0.7152	Intermediate Similarity	NPD2088	Approved
0.7152	Intermediate Similarity	NPD2087	Approved
0.7152	Intermediate Similarity	NPD8124	Phase 3
0.7152	Intermediate Similarity	NPD8126	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4738	Phase 2
0.7122	Intermediate Similarity	NPD2218	Phase 2
0.7122	Intermediate Similarity	NPD2217	Approved
0.7115	Intermediate Similarity	NPD5229	Approved
0.7115	Intermediate Similarity	NPD5230	Approved
0.7114	Intermediate Similarity	NPD7510	Approved
0.7075	Intermediate Similarity	NPD4621	Approved
0.7075	Intermediate Similarity	NPD4619	Approved
0.7075	Intermediate Similarity	NPD5299	Approved
0.7067	Intermediate Similarity	NPD4126	Approved
0.7055	Intermediate Similarity	NPD2613	Approved
0.7042	Intermediate Similarity	NPD2609	Approved
0.7042	Intermediate Similarity	NPD2612	Approved
0.7042	Intermediate Similarity	NPD3132	Approved
0.7042	Intermediate Similarity	NPD2610	Approved
0.7042	Intermediate Similarity	NPD2608	Approved
0.7042	Intermediate Similarity	NPD4216	Approved
0.7042	Intermediate Similarity	NPD4217	Approved
0.7042	Intermediate Similarity	NPD2611	Approved
0.7042	Intermediate Similarity	NPD3131	Approved
0.7042	Intermediate Similarity	NPD4215	Approved
0.7042	Intermediate Similarity	NPD4218	Approved
0.7037	Intermediate Similarity	NPD8351	Phase 2
0.7027	Intermediate Similarity	NPD3615	Approved
0.7027	Intermediate Similarity	NPD2574	Discontinued
0.7027	Intermediate Similarity	NPD2570	Approved
0.7027	Intermediate Similarity	NPD4746	Phase 3
0.7027	Intermediate Similarity	NPD2571	Approved
0.7027	Intermediate Similarity	NPD3087	Approved
0.7027	Intermediate Similarity	NPD3614	Approved
0.7027	Intermediate Similarity	NPD3616	Approved
0.7027	Intermediate Similarity	NPD4745	Approved
0.7027	Intermediate Similarity	NPD3090	Approved
0.7027	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3088	Approved
0.7027	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2566	Approved
0.7027	Intermediate Similarity	NPD3089	Approved
0.7027	Intermediate Similarity	NPD2573	Approved
0.7019	Intermediate Similarity	NPD7599	Phase 2
0.7014	Intermediate Similarity	NPD3125	Approved
0.7013	Intermediate Similarity	NPD5298	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6343	Approved
0.7	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6345	Approved
0.6987	Remote Similarity	NPD5614	Approved
0.6987	Remote Similarity	NPD3988	Approved
0.6987	Remote Similarity	NPD5613	Approved
0.6987	Remote Similarity	NPD3987	Approved
0.6986	Remote Similarity	NPD3663	Approved
0.6986	Remote Similarity	NPD3664	Approved
0.6986	Remote Similarity	NPD3662	Phase 3
0.6986	Remote Similarity	NPD3661	Approved
0.6975	Remote Similarity	NPD7600	Phase 2
0.6966	Remote Similarity	NPD2626	Approved
0.6966	Remote Similarity	NPD2625	Approved
0.6966	Remote Similarity	NPD2628	Approved
0.6966	Remote Similarity	NPD2160	Approved
0.6966	Remote Similarity	NPD2159	Approved
0.6966	Remote Similarity	NPD2627	Approved
0.6951	Remote Similarity	NPD8303	Discontinued
0.6943	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4686	Approved
0.6933	Remote Similarity	NPD3908	Approved
0.6933	Remote Similarity	NPD4684	Phase 3
0.6933	Remote Similarity	NPD4685	Phase 3
0.6928	Remote Similarity	NPD4152	Approved
0.6928	Remote Similarity	NPD7720	Phase 2
0.6918	Remote Similarity	NPD4151	Approved
0.6913	Remote Similarity	NPD941	Approved
0.6912	Remote Similarity	NPD3642	Approved
0.6912	Remote Similarity	NPD3644	Approved
0.6912	Remote Similarity	NPD3643	Approved
0.6897	Remote Similarity	NPD5367	Discontinued
0.6897	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2031	Discontinued
0.6871	Remote Similarity	NPD5204	Approved
0.6866	Remote Similarity	NPD7130	Phase 3
0.6864	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5581	Approved
0.6831	Remote Similarity	NPD5981	Approved
0.6815	Remote Similarity	NPD3519	Discontinued
0.6815	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5990	Approved
0.6809	Remote Similarity	NPD5991	Approved
0.6809	Remote Similarity	NPD2116	Approved
0.6809	Remote Similarity	NPD2115	Approved
0.6809	Remote Similarity	NPD2117	Pre-registration
0.6797	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1967	Approved
0.6795	Remote Similarity	NPD6676	Phase 2
0.6795	Remote Similarity	NPD1968	Approved
0.6792	Remote Similarity	NPD5638	Approved
0.679	Remote Similarity	NPD7105	Phase 1
0.6776	Remote Similarity	NPD5004	Approved
0.6774	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3282	Phase 1
0.6772	Remote Similarity	NPD3283	Phase 3
0.6768	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7485	Phase 3
0.6766	Remote Similarity	NPD7484	Phase 3
0.6763	Remote Similarity	NPD3598	Phase 3
0.6761	Remote Similarity	NPD2994	Approved
0.675	Remote Similarity	NPD7131	Phase 3

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