NPASS Compound

Structure

NPC8761 OpenBabel07101718192D 60 63 0 0 1 0 0 0 0 0999 V2000 -4.1470 5.3888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9736 3.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7667 -1.5976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1134 -1.5976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0936 3.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2669 5.3888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2066 6.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3203 -0.2540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7067 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6270 3.1176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3666 7.2403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5735 1.6858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8003 2.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5399 6.7631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7469 1.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4536 2.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3666 8.1949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5735 2.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6270 1.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7133 8.1949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9202 2.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1470 0.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9400 6.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2669 0.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1470 4.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9400 -1.1203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2669 4.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8003 1.6858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7133 7.2403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9202 1.6858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4536 1.6858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5399 8.6722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7469 3.1176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3203 1.2085 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9400 5.3313 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4402 1.2085 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3203 3.9570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9400 -0.1658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4402 3.9570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7067 4.6882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8801 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7667 3.0600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6468 2.1055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.1655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2803 1.2085 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 1.5399 9.6267 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 4.7469 4.0721 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -1.8801 5.1655 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7067 0.4773 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7667 2.1055 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3203 5.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2066 -0.8970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7067 3.2258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5868 1.9397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3265 6.0625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4402 -0.2540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6468 3.0600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 4.6882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 49 1 0 0 0 0 8 50 1 0 0 0 0 9 51 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 31 2 0 0 0 0 17 32 2 0 0 0 0 18 33 2 0 0 0 0 19 28 2 0 0 0 0 19 31 1 0 0 0 0 20 29 2 0 0 0 0 20 32 1 0 0 0 0 21 30 2 0 0 0 0 21 33 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 31 46 1 0 0 0 0 32 47 1 0 0 0 0 33 48 1 0 0 0 0 34 22 1 1 0 0 0 34 43 1 0 0 0 0 34 50 1 0 0 0 0 35 23 1 1 0 0 0 35 44 1 0 0 0 0 35 49 1 0 0 0 0 36 24 1 1 0 0 0 36 45 1 0 0 0 0 36 51 1 0 0 0 0 37 25 1 6 0 0 0 37 40 1 0 0 0 0 37 58 1 0 0 0 0 38 26 1 6 0 0 0 38 41 1 0 0 0 0 38 60 1 0 0 0 0 39 27 1 6 0 0 0 39 42 1 0 0 0 0 39 59 1 0 0 0 0 40 49 1 0 0 0 0 40 52 2 0 0 0 0 41 50 1 0 0 0 0 41 53 2 0 0 0 0 42 51 1 0 0 0 0 42 54 2 0 0 0 0 43 55 2 0 0 0 0 43 58 1 0 0 0 0 44 56 2 0 0 0 0 44 59 1 0 0 0 0 45 57 2 0 0 0 0 45 60 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	837.38
Volume:	843.408
LogP:	5.116
LogD:	3.935
LogS:	-5.041
# Rotatable Bonds:	9
TPSA:	139.83
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.207
Synthetic Accessibility Score:	5.15
Fsp3:	0.467
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:	-5.073
MDCK Permeability:	9.25812782952562e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.565

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	96.51302337646484%
Volume Distribution (VD):	0.748
Pgp-substrate:	1.81996750831604%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.358
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.331
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.784
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	6.016
Half-life (T1/2):	0.009

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.792
Maximum Recommended Daily Dose:	0.535
Skin Sensitization:	0.012
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC8761

Natural Product ID:	NPC8761
*Common Name:**	Beauvericin H3
IUPAC Name:	(3S,6R,9S,12R,15S,18R)-3,9,15-tris[(3-fluorophenyl)methyl]-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms:	Beauvericin H3
Standard InCHIKey:	ZLBHOQHYWAOFEC-FFCOJMSVSA-N
Standard InCHI:	InChI=1S/C45H54F3N3O9/c1-25(2)37-40(52)49(7)35(23-29-14-11-17-32(47)20-29)44(56)59-39(27(5)6)42(54)51(9)36(24-30-15-12-18-33(48)21-30)45(57)60-38(26(3)4)41(53)50(8)34(43(55)58-37)22-28-13-10-16-31(46)19-28/h10-21,25-27,34-39H,22-24H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1
SMILES:	O=C1O[C@H](C(C)C)C(=O)N(C)[C@@H](Cc2cccc(c2)F)C(=O)O[C@H](C(C)C)C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H]1Cc1cccc(c1)F)C)C(C)C)Cc1cccc(c1)F)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399265
PubChem CID:	23643109
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
NPO33182	beauveria bassiana atcc 7159	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17803266]

☑ 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
Others	1

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4400.0	nM	PMID[528502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3200.0	nM	PMID[528502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	1.4	n.a.	PMID[528502]

☑ 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 NPC8761 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	145
0.1-0.2	825
0.2-0.3	3482
0.3-0.4	15758
0.4-0.5	19040
0.5-0.6	2831
0.6-0.7	493
0.7-0.8	114
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC44805
0.9919	High Similarity	NPC157311
0.9675	High Similarity	NPC71933
0.9675	High Similarity	NPC152850
0.9675	High Similarity	NPC89923
0.9675	High Similarity	NPC239990
0.9675	High Similarity	NPC105114
0.9593	High Similarity	NPC136453
0.8156	Intermediate Similarity	NPC209509
0.8014	Intermediate Similarity	NPC139326
0.7986	Intermediate Similarity	NPC105717
0.7943	Intermediate Similarity	NPC269398
0.7943	Intermediate Similarity	NPC263493
0.7902	Intermediate Similarity	NPC5620
0.7887	Intermediate Similarity	NPC161069
0.7857	Intermediate Similarity	NPC127741
0.7857	Intermediate Similarity	NPC68865
0.7801	Intermediate Similarity	NPC178662
0.7801	Intermediate Similarity	NPC92784
0.7801	Intermediate Similarity	NPC470884
0.7801	Intermediate Similarity	NPC98424
0.7801	Intermediate Similarity	NPC476133
0.777	Intermediate Similarity	NPC286551
0.7746	Intermediate Similarity	NPC268841
0.7746	Intermediate Similarity	NPC307357
0.7746	Intermediate Similarity	NPC46098
0.773	Intermediate Similarity	NPC471264
0.773	Intermediate Similarity	NPC471265
0.7687	Intermediate Similarity	NPC129666
0.7671	Intermediate Similarity	NPC329761
0.7671	Intermediate Similarity	NPC138775
0.7671	Intermediate Similarity	NPC145113
0.7671	Intermediate Similarity	NPC225648
0.7622	Intermediate Similarity	NPC163392
0.7622	Intermediate Similarity	NPC239762
0.7609	Intermediate Similarity	NPC473322
0.75	Intermediate Similarity	NPC471821
0.75	Intermediate Similarity	NPC471820
0.75	Intermediate Similarity	NPC255447
0.7483	Intermediate Similarity	NPC262077
0.7466	Intermediate Similarity	NPC476978
0.7444	Intermediate Similarity	NPC169328
0.7438	Intermediate Similarity	NPC326407
0.7438	Intermediate Similarity	NPC317725
0.7417	Intermediate Similarity	NPC122590
0.7398	Intermediate Similarity	NPC322598
0.7397	Intermediate Similarity	NPC197682
0.7388	Intermediate Similarity	NPC310467
0.7388	Intermediate Similarity	NPC470546
0.7383	Intermediate Similarity	NPC240848
0.7357	Intermediate Similarity	NPC111428
0.7351	Intermediate Similarity	NPC162104
0.7338	Intermediate Similarity	NPC197743
0.7338	Intermediate Similarity	NPC297145
0.7329	Intermediate Similarity	NPC469426
0.7329	Intermediate Similarity	NPC168113
0.7329	Intermediate Similarity	NPC469427
0.7323	Intermediate Similarity	NPC473418
0.7315	Intermediate Similarity	NPC135121
0.7313	Intermediate Similarity	NPC470545
0.731	Intermediate Similarity	NPC132636
0.7297	Intermediate Similarity	NPC201244
0.7297	Intermediate Similarity	NPC477217
0.7279	Intermediate Similarity	NPC45777
0.7279	Intermediate Similarity	NPC477061
0.7279	Intermediate Similarity	NPC176226
0.7261	Intermediate Similarity	NPC471053
0.7261	Intermediate Similarity	NPC471052
0.7261	Intermediate Similarity	NPC471051
0.7239	Intermediate Similarity	NPC470544
0.723	Intermediate Similarity	NPC52748
0.7222	Intermediate Similarity	NPC248283
0.7219	Intermediate Similarity	NPC2501
0.7203	Intermediate Similarity	NPC246079
0.719	Intermediate Similarity	NPC473341
0.7163	Intermediate Similarity	NPC319766
0.7153	Intermediate Similarity	NPC190663
0.7143	Intermediate Similarity	NPC476259
0.7143	Intermediate Similarity	NPC4974
0.7143	Intermediate Similarity	NPC47667
0.7134	Intermediate Similarity	NPC471527
0.7132	Intermediate Similarity	NPC237420
0.7123	Intermediate Similarity	NPC43755
0.7117	Intermediate Similarity	NPC159767
0.7117	Intermediate Similarity	NPC318930
0.7117	Intermediate Similarity	NPC155506
0.7117	Intermediate Similarity	NPC317362
0.7101	Intermediate Similarity	NPC71684
0.709	Intermediate Similarity	NPC33742
0.7071	Intermediate Similarity	NPC222466
0.7067	Intermediate Similarity	NPC313867
0.7067	Intermediate Similarity	NPC316008
0.705	Intermediate Similarity	NPC160493
0.7042	Intermediate Similarity	NPC210950
0.7042	Intermediate Similarity	NPC199738
0.7021	Intermediate Similarity	NPC101719
0.702	Intermediate Similarity	NPC314358
0.7015	Intermediate Similarity	NPC276949
0.7015	Intermediate Similarity	NPC35850
0.7	Intermediate Similarity	NPC315283
0.7	Intermediate Similarity	NPC314388
0.6994	Remote Similarity	NPC230611
0.6981	Remote Similarity	NPC73644
0.6966	Remote Similarity	NPC246913
0.6951	Remote Similarity	NPC137627
0.6951	Remote Similarity	NPC306804
0.6939	Remote Similarity	NPC90194
0.6939	Remote Similarity	NPC151706
0.6939	Remote Similarity	NPC475598
0.6939	Remote Similarity	NPC49577
0.6939	Remote Similarity	NPC9687
0.6939	Remote Similarity	NPC474855
0.6939	Remote Similarity	NPC293377
0.6939	Remote Similarity	NPC260045
0.6939	Remote Similarity	NPC118099
0.6939	Remote Similarity	NPC273907
0.6939	Remote Similarity	NPC76785
0.6939	Remote Similarity	NPC79465
0.6939	Remote Similarity	NPC474811
0.6939	Remote Similarity	NPC476102
0.6939	Remote Similarity	NPC474787
0.6939	Remote Similarity	NPC475318
0.6923	Remote Similarity	NPC476198
0.6914	Remote Similarity	NPC294516
0.6914	Remote Similarity	NPC107938
0.6909	Remote Similarity	NPC473402
0.6909	Remote Similarity	NPC279871
0.6906	Remote Similarity	NPC478014
0.6906	Remote Similarity	NPC478016
0.6906	Remote Similarity	NPC200964
0.6906	Remote Similarity	NPC478015
0.6906	Remote Similarity	NPC80150
0.6903	Remote Similarity	NPC233702
0.6901	Remote Similarity	NPC474847
0.6897	Remote Similarity	NPC130309
0.6879	Remote Similarity	NPC35996
0.6879	Remote Similarity	NPC46427
0.6879	Remote Similarity	NPC6975
0.6875	Remote Similarity	NPC213969
0.6875	Remote Similarity	NPC165726
0.6855	Remote Similarity	NPC62104
0.6855	Remote Similarity	NPC1390
0.6853	Remote Similarity	NPC477937
0.6839	Remote Similarity	NPC7817
0.6839	Remote Similarity	NPC475168
0.6829	Remote Similarity	NPC196091
0.6829	Remote Similarity	NPC40234
0.6828	Remote Similarity	NPC200589
0.6828	Remote Similarity	NPC69496
0.6824	Remote Similarity	NPC294951
0.681	Remote Similarity	NPC473502
0.6809	Remote Similarity	NPC84281
0.6809	Remote Similarity	NPC252878
0.6809	Remote Similarity	NPC317474
0.6809	Remote Similarity	NPC291027
0.6809	Remote Similarity	NPC213126
0.6809	Remote Similarity	NPC169485
0.6807	Remote Similarity	NPC476227
0.6807	Remote Similarity	NPC477462
0.6807	Remote Similarity	NPC26108
0.6803	Remote Similarity	NPC245836
0.6803	Remote Similarity	NPC233910
0.6803	Remote Similarity	NPC313663
0.6803	Remote Similarity	NPC287401
0.6797	Remote Similarity	NPC81026
0.6794	Remote Similarity	NPC67043
0.679	Remote Similarity	NPC223207
0.6788	Remote Similarity	NPC89831
0.6786	Remote Similarity	NPC194671
0.6786	Remote Similarity	NPC269750
0.6786	Remote Similarity	NPC45037
0.6763	Remote Similarity	NPC220698
0.6748	Remote Similarity	NPC304074
0.6748	Remote Similarity	NPC471771
0.6748	Remote Similarity	NPC290755
0.6747	Remote Similarity	NPC248670
0.6747	Remote Similarity	NPC273755
0.6739	Remote Similarity	NPC239357
0.6738	Remote Similarity	NPC202521
0.6738	Remote Similarity	NPC314192
0.6736	Remote Similarity	NPC65310
0.6735	Remote Similarity	NPC257390
0.6733	Remote Similarity	NPC77992
0.6732	Remote Similarity	NPC266741
0.6732	Remote Similarity	NPC315266
0.6716	Remote Similarity	NPC158854
0.6713	Remote Similarity	NPC22746
0.6709	Remote Similarity	NPC470902
0.6707	Remote Similarity	NPC158277
0.6707	Remote Similarity	NPC473354
0.6691	Remote Similarity	NPC474584
0.6687	Remote Similarity	NPC63931
0.6687	Remote Similarity	NPC5719
0.6687	Remote Similarity	NPC210377
0.6687	Remote Similarity	NPC22883
0.6687	Remote Similarity	NPC217804
0.6686	Remote Similarity	NPC475421
0.6667	Remote Similarity	NPC319579
0.6667	Remote Similarity	NPC472165
0.6667	Remote Similarity	NPC473573

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 NPC8761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	108
0.1-0.2	429
0.2-0.3	833
0.3-0.4	2392
0.4-0.5	3305
0.5-0.6	1616
0.6-0.7	436
0.7-0.8	31
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
0.7714	Intermediate Similarity	NPD6623	Phase 3
0.7671	Intermediate Similarity	NPD8323	Discontinued
0.7634	Intermediate Similarity	NPD4576	Approved
0.7634	Intermediate Similarity	NPD4574	Approved
0.7552	Intermediate Similarity	NPD6295	Approved
0.7552	Intermediate Similarity	NPD6294	Approved
0.7483	Intermediate Similarity	NPD6073	Approved
0.7445	Intermediate Similarity	NPD4677	Discontinued
0.7394	Intermediate Similarity	NPD5747	Discontinued
0.7394	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD6345	Approved
0.7388	Intermediate Similarity	NPD6343	Approved
0.7388	Intermediate Similarity	NPD5859	Discontinued
0.7372	Intermediate Similarity	NPD2584	Suspended
0.7357	Intermediate Similarity	NPD4177	Approved
0.7357	Intermediate Similarity	NPD4175	Approved
0.7241	Intermediate Similarity	NPD7510	Approved
0.7241	Intermediate Similarity	NPD5725	Approved
0.7222	Intermediate Similarity	NPD8265	Approved
0.7203	Intermediate Similarity	NPD5581	Approved
0.7192	Intermediate Similarity	NPD6852	Discontinued
0.719	Intermediate Similarity	NPD8352	Phase 1
0.7185	Intermediate Similarity	NPD6065	Approved
0.7185	Intermediate Similarity	NPD5990	Approved
0.7185	Intermediate Similarity	NPD5991	Approved
0.7183	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD8417	Discontinued
0.7153	Intermediate Similarity	NPD4488	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6792	Phase 3
0.7123	Intermediate Similarity	NPD8173	Phase 2
0.7123	Intermediate Similarity	NPD8172	Phase 2
0.7103	Intermediate Similarity	NPD4153	Approved
0.7103	Intermediate Similarity	NPD5296	Approved
0.7101	Intermediate Similarity	NPD7813	Approved
0.7101	Intermediate Similarity	NPD7815	Approved
0.7095	Intermediate Similarity	NPD7512	Approved
0.7095	Intermediate Similarity	NPD7511	Approved
0.7063	Intermediate Similarity	NPD4620	Approved
0.7063	Intermediate Similarity	NPD5201	Approved
0.7063	Intermediate Similarity	NPD5263	Approved
0.7063	Intermediate Similarity	NPD5203	Approved
0.7063	Intermediate Similarity	NPD4617	Approved
0.7055	Intermediate Similarity	NPD8643	Discontinued
0.705	Intermediate Similarity	NPD7437	Approved
0.705	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7436	Approved
0.7021	Intermediate Similarity	NPD5667	Approved
0.7014	Intermediate Similarity	NPD4794	Discontinued
0.7	Intermediate Similarity	NPD3073	Approved
0.7	Intermediate Similarity	NPD3072	Approved
0.7	Intermediate Similarity	NPD7814	Approved
0.7	Intermediate Similarity	NPD7130	Phase 3
0.7	Intermediate Similarity	NPD5706	Approved
0.7	Intermediate Similarity	NPD5704	Approved
0.7	Intermediate Similarity	NPD5705	Approved
0.7	Intermediate Similarity	NPD3071	Approved
0.6993	Remote Similarity	NPD5759	Approved
0.6986	Remote Similarity	NPD5121	Approved
0.6986	Remote Similarity	NPD5120	Approved
0.6986	Remote Similarity	NPD5119	Approved
0.6986	Remote Similarity	NPD8416	Discontinued
0.697	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4621	Approved
0.6966	Remote Similarity	NPD4619	Approved
0.6957	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5941	Approved
0.6948	Remote Similarity	NPD5942	Approved
0.6947	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2607	Approved
0.6939	Remote Similarity	NPD8302	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4807	Approved
0.6929	Remote Similarity	NPD4806	Approved
0.6929	Remote Similarity	NPD7798	Approved
0.6929	Remote Similarity	NPD4762	Approved
0.6929	Remote Similarity	NPD4761	Approved
0.6923	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7086	Phase 2
0.6906	Remote Similarity	NPD6806	Phase 1
0.6901	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6039	Approved
0.6892	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7042	Phase 3
0.6884	Remote Similarity	NPD2994	Approved
0.6875	Remote Similarity	NPD5204	Approved
0.6871	Remote Similarity	NPD3373	Approved
0.6861	Remote Similarity	NPD7679	Phase 2
0.6857	Remote Similarity	NPD4135	Approved
0.6857	Remote Similarity	NPD4136	Approved
0.6857	Remote Similarity	NPD4106	Approved
0.6853	Remote Similarity	NPD6564	Approved
0.6853	Remote Similarity	NPD6563	Approved
0.6853	Remote Similarity	NPD6565	Approved
0.6832	Remote Similarity	NPD8351	Phase 2
0.6828	Remote Similarity	NPD4676	Approved
0.6828	Remote Similarity	NPD4125	Approved
0.6828	Remote Similarity	NPD2613	Approved
0.6821	Remote Similarity	NPD7720	Phase 2
0.6815	Remote Similarity	NPD8315	Phase 1
0.6812	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3132	Approved
0.6809	Remote Similarity	NPD4218	Approved
0.6809	Remote Similarity	NPD2610	Approved
0.6809	Remote Similarity	NPD2612	Approved
0.6809	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2611	Approved
0.6809	Remote Similarity	NPD4216	Approved
0.6809	Remote Similarity	NPD2608	Approved
0.6809	Remote Similarity	NPD2609	Approved
0.6809	Remote Similarity	NPD4215	Approved
0.6809	Remote Similarity	NPD3131	Approved
0.6809	Remote Similarity	NPD4217	Approved
0.6806	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3087	Approved
0.6803	Remote Similarity	NPD3088	Approved
0.6803	Remote Similarity	NPD4745	Approved
0.6803	Remote Similarity	NPD3614	Approved
0.6803	Remote Similarity	NPD3090	Approved
0.6803	Remote Similarity	NPD2573	Approved
0.6803	Remote Similarity	NPD3615	Approved
0.6803	Remote Similarity	NPD2566	Approved
0.6803	Remote Similarity	NPD3089	Approved
0.6803	Remote Similarity	NPD3616	Approved
0.6803	Remote Similarity	NPD4746	Phase 3
0.6803	Remote Similarity	NPD2574	Discontinued
0.6803	Remote Similarity	NPD7714	Approved
0.6803	Remote Similarity	NPD2570	Approved
0.6803	Remote Similarity	NPD2571	Approved
0.6803	Remote Similarity	NPD7715	Approved
0.6803	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7613	Discontinued
0.6792	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2199	Approved
0.6783	Remote Similarity	NPD2198	Approved
0.6774	Remote Similarity	NPD8165	Discontinued
0.6774	Remote Similarity	NPD6088	Approved
0.6765	Remote Similarity	NPD3598	Phase 3
0.6759	Remote Similarity	NPD3040	Approved
0.6748	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5500	Discontinued
0.6738	Remote Similarity	NPD5579	Approved
0.6738	Remote Similarity	NPD2946	Phase 2
0.6738	Remote Similarity	NPD5576	Approved
0.6736	Remote Similarity	NPD2627	Approved
0.6736	Remote Similarity	NPD2159	Approved
0.6736	Remote Similarity	NPD2160	Approved
0.6736	Remote Similarity	NPD2626	Approved
0.6736	Remote Similarity	NPD2625	Approved
0.6736	Remote Similarity	NPD2628	Approved
0.6732	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5264	Approved
0.6732	Remote Similarity	NPD5265	Approved
0.6716	Remote Similarity	NPD4233	Approved
0.6716	Remote Similarity	NPD1756	Approved
0.6716	Remote Similarity	NPD4234	Approved
0.6716	Remote Similarity	NPD1752	Approved
0.6715	Remote Similarity	NPD747	Discontinued
0.6715	Remote Similarity	NPD3551	Approved
0.6714	Remote Similarity	NPD3031	Approved
0.6714	Remote Similarity	NPD3030	Approved
0.6714	Remote Similarity	NPD4105	Approved
0.6714	Remote Similarity	NPD4102	Approved
0.6714	Remote Similarity	NPD3032	Approved
0.6714	Remote Similarity	NPD5981	Approved
0.6711	Remote Similarity	NPD4684	Phase 3
0.6711	Remote Similarity	NPD4685	Phase 3
0.6711	Remote Similarity	NPD4686	Approved
0.6711	Remote Similarity	NPD7733	Phase 2
0.6708	Remote Similarity	NPD7599	Phase 2
0.6692	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4151	Approved
0.669	Remote Similarity	NPD5993	Phase 1
0.669	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5638	Approved
0.6687	Remote Similarity	NPD7105	Phase 1
0.6667	Remote Similarity	NPD3643	Approved
0.6667	Remote Similarity	NPD7600	Phase 2
0.6667	Remote Similarity	NPD7508	Discontinued
0.6667	Remote Similarity	NPD6681	Discovery
0.6667	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6544	Discontinued
0.6667	Remote Similarity	NPD3644	Approved
0.6667	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3642	Approved
0.6647	Remote Similarity	NPD7854	Phase 2
0.6645	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6310	Approved
0.6644	Remote Similarity	NPD3661	Approved
0.6644	Remote Similarity	NPD6311	Approved
0.6644	Remote Similarity	NPD3663	Approved
0.6644	Remote Similarity	NPD3664	Approved
0.6644	Remote Similarity	NPD3662	Phase 3
0.6644	Remote Similarity	NPD6309	Approved
0.6643	Remote Similarity	NPD6408	Phase 1
0.6642	Remote Similarity	NPD1370	Approved
0.6642	Remote Similarity	NPD1374	Approved
0.6642	Remote Similarity	NPD1371	Approved
0.6642	Remote Similarity	NPD1373	Approved
0.6642	Remote Similarity	NPD2652	Approved
0.6642	Remote Similarity	NPD2650	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