NPASS Compound

Structure

NPC132636 OpenBabel07101719142D 57 59 0 0 1 0 0 0 0 0999 V2000 2.3475 5.9610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4026 9.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7267 3.7032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0108 7.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0490 -1.1085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2721 -0.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1194 5.3253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1839 8.4360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7600 -0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3234 -2.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8700 0.1508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8442 -1.2449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4574 -1.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1894 -1.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1230 5.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9448 5.1006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0642 0.7430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0384 -0.6526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4574 -0.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1894 -0.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1608 5.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3427 0.9335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4269 0.5318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5370 4.2948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3234 0.9043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9548 4.3389 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2295 8.1375 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9939 -0.1100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1484 0.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3234 -0.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1623 5.8874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6211 1.1241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4574 1.4043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0183 3.9883 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4938 8.8148 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9697 0.1087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8080 2.3408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7642 5.5111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2100 3.0068 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 0.7124 9.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6793 7.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8356 3.3404 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0727 2.0163 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8216 0.6323 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0564 6.8632 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5183 4.8543 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4606 8.5163 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 -2.3460 -0.8178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7895 2.1491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2879 6.3630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2096 3.0344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4742 -0.3950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6668 10.0891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0233 10.4679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6337 7.2420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 6 49 1 0 0 0 0 7 26 1 0 0 0 0 8 27 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 24 1 0 0 0 0 17 29 2 0 0 0 0 18 29 1 0 0 0 0 19 30 2 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 24 43 1 0 0 0 0 25 30 1 0 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 27 35 1 0 0 0 0 28 5 1 1 0 0 0 28 36 1 0 0 0 0 28 49 1 0 0 0 0 31 38 1 0 0 0 0 31 46 1 1 0 0 0 32 23 1 1 0 0 0 32 40 1 0 0 0 0 32 44 1 0 0 0 0 33 25 1 1 0 0 0 33 37 1 0 0 0 0 33 45 1 0 0 0 0 34 26 1 1 0 0 0 34 39 1 0 0 0 0 34 47 1 0 0 0 0 35 41 1 6 0 0 0 35 48 1 0 0 0 0 36 45 2 3 0 0 0 36 50 1 0 0 0 0 37 43 2 3 0 0 0 37 51 1 0 0 0 0 38 47 2 3 0 0 0 38 52 1 0 0 0 0 39 44 2 3 0 0 0 39 53 1 0 0 0 0 40 49 1 0 0 0 0 40 54 2 0 0 0 0 41 55 2 0 0 0 0 41 56 1 0 0 0 0 42 46 2 3 0 0 0 42 48 1 0 0 0 0 42 57 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	791.46
Volume:	822.344
LogP:	3.949
LogD:	3.131
LogS:	-3.26
# Rotatable Bonds:	14
TPSA:	218.63
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	5.428
Fsp3:	0.548
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:	-6.388
MDCK Permeability:	2.6759900720207952e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.766
20% Bioavailability (F20%):	0.55
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	82.7945556640625%
Volume Distribution (VD):	0.301
Pgp-substrate:	4.3858819007873535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.32
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.247
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	1.421
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.972
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.324
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.204
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.557

Download Data

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

Natural Product: NPC132636

Natural Product ID:	NPC132636
*Common Name:**	Schizopeptin 791
IUPAC Name:	(2S,3S)-2-[[(3S,6S,9S,12S,15R)-3-benzyl-12-[(2S)-butan-2-yl]-6,7-dimethyl-2,5,8,11,14-pentaoxo-9-(2-phenylethyl)-1,4,7,10,13-pentazacyclononadec-15-yl]carbamoylamino]-3-methylpentanoic acid
Synonyms:	Schizopeptin 791
Standard InCHIKey:	UHGIIADZWWCEKS-NDSQDYTJSA-N
Standard InCHI:	InChI=1S/C42H61N7O8/c1-7-26(3)34-39(53)44-32(23-22-29-17-11-9-12-18-29)40(54)49(6)28(5)36(50)45-33(25-30-19-13-10-14-20-30)37(51)43-24-16-15-21-31(38(52)47-34)46-42(57)48-35(41(55)56)27(4)8-2/h9-14,17-20,26-28,31-35H,7-8,15-16,21-25H2,1-6H3,(H,43,51)(H,44,53)(H,45,50)(H,47,52)(H,55,56)(H2,46,48,57)/t26-,27-,28-,31+,32-,33-,34-,35-/m0/s1
SMILES:	CC[C@@H]([C@@H](C(=O)O)NC(=N[C@@H]1CCCCN=C(O)[C@H](Cc2ccccc2)N=C([C@@H](N(C(=O)[C@@H](N=C([C@@H](N=C1O)[C@H](CC)C)O)CCc1ccccc1)C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2368571
PubChem CID:	10985632
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
NPO33068	Schizothrix sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10691708]
NPO33068	Schizothrix sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12193029]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	45.0	ug.mL-1	PMID[470808]

☑ 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 NPC132636 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	155
0.1-0.2	1038
0.2-0.3	6546
0.3-0.4	20684
0.4-0.5	11499
0.5-0.6	1929
0.6-0.7	518
0.7-0.8	288
0.8-0.85	29
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9219	High Similarity	NPC477937
0.8828	High Similarity	NPC71684
0.8767	High Similarity	NPC469243
0.8639	High Similarity	NPC475544
0.8594	High Similarity	NPC470546
0.8591	High Similarity	NPC223207
0.8533	High Similarity	NPC304074
0.8533	High Similarity	NPC471771
0.8533	High Similarity	NPC290755
0.8516	High Similarity	NPC470545
0.8493	Intermediate Similarity	NPC473580
0.8438	Intermediate Similarity	NPC470544
0.8421	Intermediate Similarity	NPC101719
0.837	Intermediate Similarity	NPC473322
0.837	Intermediate Similarity	NPC111428
0.8366	Intermediate Similarity	NPC198254
0.8366	Intermediate Similarity	NPC274198
0.8346	Intermediate Similarity	NPC222466
0.8322	Intermediate Similarity	NPC314114
0.8273	Intermediate Similarity	NPC314835
0.8248	Intermediate Similarity	NPC255447
0.8247	Intermediate Similarity	NPC276506
0.8243	Intermediate Similarity	NPC469903
0.8153	Intermediate Similarity	NPC196243
0.8133	Intermediate Similarity	NPC324850
0.8125	Intermediate Similarity	NPC474584
0.8112	Intermediate Similarity	NPC161069
0.8085	Intermediate Similarity	NPC127741
0.8079	Intermediate Similarity	NPC1390
0.8079	Intermediate Similarity	NPC62104
0.8045	Intermediate Similarity	NPC200964
0.8026	Intermediate Similarity	NPC469902
0.8014	Intermediate Similarity	NPC311658
0.8	Intermediate Similarity	NPC209509
0.7987	Intermediate Similarity	NPC122590
0.7969	Intermediate Similarity	NPC319579
0.7941	Intermediate Similarity	NPC22746
0.7914	Intermediate Similarity	NPC200589
0.7891	Intermediate Similarity	NPC138775
0.7888	Intermediate Similarity	NPC153554
0.7879	Intermediate Similarity	NPC239357
0.7871	Intermediate Similarity	NPC22883
0.7871	Intermediate Similarity	NPC210377
0.7871	Intermediate Similarity	NPC217804
0.7871	Intermediate Similarity	NPC5719
0.7863	Intermediate Similarity	NPC33742
0.7862	Intermediate Similarity	NPC139326
0.7847	Intermediate Similarity	NPC239762
0.7847	Intermediate Similarity	NPC163392
0.7838	Intermediate Similarity	NPC105717
0.7821	Intermediate Similarity	NPC15068
0.7808	Intermediate Similarity	NPC52748
0.78	Intermediate Similarity	NPC300443
0.7793	Intermediate Similarity	NPC263493
0.7793	Intermediate Similarity	NPC269398
0.7786	Intermediate Similarity	NPC276949
0.7786	Intermediate Similarity	NPC35850
0.7785	Intermediate Similarity	NPC2501
0.7771	Intermediate Similarity	NPC63040
0.777	Intermediate Similarity	NPC319766
0.7755	Intermediate Similarity	NPC315266
0.7755	Intermediate Similarity	NPC5620
0.7748	Intermediate Similarity	NPC473341
0.774	Intermediate Similarity	NPC197682
0.7737	Intermediate Similarity	NPC6975
0.773	Intermediate Similarity	NPC130309
0.7724	Intermediate Similarity	NPC476259
0.7722	Intermediate Similarity	NPC469904
0.7708	Intermediate Similarity	NPC68865
0.7703	Intermediate Similarity	NPC262077
0.7697	Intermediate Similarity	NPC473002
0.7687	Intermediate Similarity	NPC476978
0.7677	Intermediate Similarity	NPC471527
0.7677	Intermediate Similarity	NPC473003
0.7671	Intermediate Similarity	NPC168113
0.7656	Intermediate Similarity	NPC327481
0.7655	Intermediate Similarity	NPC470884
0.7655	Intermediate Similarity	NPC98424
0.7655	Intermediate Similarity	NPC476133
0.7655	Intermediate Similarity	NPC92784
0.7655	Intermediate Similarity	NPC178662
0.7643	Intermediate Similarity	NPC63931
0.7632	Intermediate Similarity	NPC286551
0.7619	Intermediate Similarity	NPC176226
0.7619	Intermediate Similarity	NPC77905
0.7609	Intermediate Similarity	NPC35996
0.7603	Intermediate Similarity	NPC46098
0.7603	Intermediate Similarity	NPC307357
0.7603	Intermediate Similarity	NPC268841
0.76	Intermediate Similarity	NPC471821
0.76	Intermediate Similarity	NPC471820
0.7591	Intermediate Similarity	NPC202521
0.7586	Intermediate Similarity	NPC471264
0.7586	Intermediate Similarity	NPC471265
0.7578	Intermediate Similarity	NPC67043
0.7578	Intermediate Similarity	NPC475532
0.7569	Intermediate Similarity	NPC141050
0.7551	Intermediate Similarity	NPC469426
0.7551	Intermediate Similarity	NPC469427
0.755	Intermediate Similarity	NPC129666
0.7535	Intermediate Similarity	NPC300315
0.7533	Intermediate Similarity	NPC225648
0.7533	Intermediate Similarity	NPC135121
0.7533	Intermediate Similarity	NPC329761
0.7531	Intermediate Similarity	NPC165285
0.7518	Intermediate Similarity	NPC105114
0.7518	Intermediate Similarity	NPC71933
0.7518	Intermediate Similarity	NPC89923
0.7518	Intermediate Similarity	NPC239990
0.7518	Intermediate Similarity	NPC476990
0.7518	Intermediate Similarity	NPC152850
0.7517	Intermediate Similarity	NPC477217
0.7517	Intermediate Similarity	NPC313867
0.7517	Intermediate Similarity	NPC201244
0.7517	Intermediate Similarity	NPC316008
0.75	Intermediate Similarity	NPC24617
0.75	Intermediate Similarity	NPC329011
0.75	Intermediate Similarity	NPC7817
0.75	Intermediate Similarity	NPC47667
0.75	Intermediate Similarity	NPC475168
0.7482	Intermediate Similarity	NPC46427
0.7481	Intermediate Similarity	NPC285926
0.7481	Intermediate Similarity	NPC315276
0.7481	Intermediate Similarity	NPC14672
0.7467	Intermediate Similarity	NPC314358
0.7452	Intermediate Similarity	NPC469901
0.7452	Intermediate Similarity	NPC114806
0.7451	Intermediate Similarity	NPC233702
0.745	Intermediate Similarity	NPC315283
0.745	Intermediate Similarity	NPC314388
0.7447	Intermediate Similarity	NPC136453
0.7439	Intermediate Similarity	NPC473001
0.7436	Intermediate Similarity	NPC197743
0.7436	Intermediate Similarity	NPC297145
0.7426	Intermediate Similarity	NPC169328
0.7422	Intermediate Similarity	NPC164859
0.7421	Intermediate Similarity	NPC189116
0.7417	Intermediate Similarity	NPC145113
0.7417	Intermediate Similarity	NPC16188
0.7412	Intermediate Similarity	NPC61332
0.7412	Intermediate Similarity	NPC240130
0.741	Intermediate Similarity	NPC252878
0.7407	Intermediate Similarity	NPC197470
0.74	Intermediate Similarity	NPC322878
0.7391	Intermediate Similarity	NPC129486
0.7391	Intermediate Similarity	NPC280022
0.7379	Intermediate Similarity	NPC287401
0.7372	Intermediate Similarity	NPC310467
0.7361	Intermediate Similarity	NPC157311
0.7358	Intermediate Similarity	NPC471053
0.7358	Intermediate Similarity	NPC471052
0.7358	Intermediate Similarity	NPC471051
0.7355	Intermediate Similarity	NPC470902
0.7329	Intermediate Similarity	NPC248283
0.7317	Intermediate Similarity	NPC17698
0.731	Intermediate Similarity	NPC44805
0.731	Intermediate Similarity	NPC246079
0.731	Intermediate Similarity	NPC325479
0.731	Intermediate Similarity	NPC8761
0.7305	Intermediate Similarity	NPC473404
0.7296	Intermediate Similarity	NPC73655
0.7294	Intermediate Similarity	NPC94862
0.729	Intermediate Similarity	NPC202198
0.7283	Intermediate Similarity	NPC302715
0.7278	Intermediate Similarity	NPC319320
0.7278	Intermediate Similarity	NPC287757
0.7267	Intermediate Similarity	NPC468984
0.7267	Intermediate Similarity	NPC61004
0.7266	Intermediate Similarity	NPC478016
0.7266	Intermediate Similarity	NPC477061
0.7266	Intermediate Similarity	NPC478015
0.7266	Intermediate Similarity	NPC478014
0.7266	Intermediate Similarity	NPC45777
0.7256	Intermediate Similarity	NPC306804
0.7255	Intermediate Similarity	NPC240848
0.7246	Intermediate Similarity	NPC220698
0.7246	Intermediate Similarity	NPC314992
0.723	Intermediate Similarity	NPC43755
0.7226	Intermediate Similarity	NPC162104
0.7222	Intermediate Similarity	NPC328649
0.7212	Intermediate Similarity	NPC477462
0.7192	Intermediate Similarity	NPC326966
0.7188	Intermediate Similarity	NPC241794
0.7188	Intermediate Similarity	NPC12730
0.7186	Intermediate Similarity	NPC119652
0.7186	Intermediate Similarity	NPC97526
0.7178	Intermediate Similarity	NPC473000
0.7176	Intermediate Similarity	NPC473418
0.717	Intermediate Similarity	NPC469898
0.7169	Intermediate Similarity	NPC469900
0.7143	Intermediate Similarity	NPC472999
0.7134	Intermediate Similarity	NPC46009
0.7122	Intermediate Similarity	NPC237420
0.7113	Intermediate Similarity	NPC474082
0.7113	Intermediate Similarity	NPC175726
0.7109	Intermediate Similarity	NPC322598
0.7101	Intermediate Similarity	NPC2265
0.7097	Intermediate Similarity	NPC254798
0.7086	Intermediate Similarity	NPC476989
0.7083	Intermediate Similarity	NPC194671

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 NPC132636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	107
0.1-0.2	311
0.2-0.3	732
0.3-0.4	1823
0.4-0.5	3846
0.5-0.6	1837
0.6-0.7	384
0.7-0.8	101
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8633	High Similarity	NPD8076	Discontinued
0.8551	High Similarity	NPD6901	Phase 3
0.8433	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD4677	Discontinued
0.8227	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD5581	Approved
0.8043	Intermediate Similarity	NPD5263	Approved
0.8027	Intermediate Similarity	NPD6088	Approved
0.8014	Intermediate Similarity	NPD3908	Approved
0.8	Intermediate Similarity	NPD3073	Approved
0.8	Intermediate Similarity	NPD3072	Approved
0.8	Intermediate Similarity	NPD3071	Approved
0.7986	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6623	Phase 3
0.7931	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD4762	Approved
0.7926	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD4761	Approved
0.7887	Intermediate Similarity	NPD8643	Discontinued
0.7862	Intermediate Similarity	NPD7720	Phase 2
0.7842	Intermediate Similarity	NPD3040	Approved
0.7832	Intermediate Similarity	NPD6073	Approved
0.7812	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4676	Approved
0.7786	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6294	Approved
0.7778	Intermediate Similarity	NPD6295	Approved
0.777	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD5367	Discontinued
0.7714	Intermediate Similarity	NPD4177	Approved
0.7714	Intermediate Similarity	NPD4175	Approved
0.7714	Intermediate Similarity	NPD7828	Discontinued
0.7676	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6852	Discontinued
0.7643	Intermediate Similarity	NPD4151	Approved
0.7613	Intermediate Similarity	NPD7495	Discontinued
0.7595	Intermediate Similarity	NPD8303	Discontinued
0.7586	Intermediate Similarity	NPD5725	Approved
0.7582	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3606	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4153	Approved
0.7569	Intermediate Similarity	NPD5323	Approved
0.7569	Intermediate Similarity	NPD8416	Discontinued
0.7566	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4125	Approved
0.7534	Intermediate Similarity	NPD4214	Discontinued
0.7533	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD8323	Discontinued
0.7518	Intermediate Similarity	NPD7342	Discontinued
0.7517	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2584	Suspended
0.7466	Intermediate Similarity	NPD8173	Phase 2
0.7466	Intermediate Similarity	NPD8172	Phase 2
0.7448	Intermediate Similarity	NPD5296	Approved
0.7434	Intermediate Similarity	NPD5613	Approved
0.7434	Intermediate Similarity	NPD5614	Approved
0.7431	Intermediate Similarity	NPD5299	Approved
0.7424	Intermediate Similarity	NPD3642	Approved
0.7424	Intermediate Similarity	NPD3644	Approved
0.7424	Intermediate Similarity	NPD3643	Approved
0.7417	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1348	Approved
0.74	Intermediate Similarity	NPD5024	Approved
0.7379	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5747	Discontinued
0.7379	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4158	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1968	Approved
0.7351	Intermediate Similarity	NPD1967	Approved
0.7333	Intermediate Similarity	NPD6681	Discovery
0.7324	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3987	Approved
0.732	Intermediate Similarity	NPD3988	Approved
0.7297	Intermediate Similarity	NPD4126	Approved
0.7285	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8019	Approved
0.7267	Intermediate Similarity	NPD2087	Approved
0.7267	Intermediate Similarity	NPD2088	Approved
0.7246	Intermediate Similarity	NPD2217	Approved
0.7246	Intermediate Similarity	NPD2218	Phase 2
0.7214	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1330	Phase 2
0.7192	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6646	Discontinued
0.7185	Intermediate Similarity	NPD480	Approved
0.7179	Intermediate Similarity	NPD7523	Phase 3
0.717	Intermediate Similarity	NPD4517	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4432	Discontinued
0.7161	Intermediate Similarity	NPD5942	Approved
0.7161	Intermediate Similarity	NPD5941	Approved
0.7153	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3519	Discontinued
0.7124	Intermediate Similarity	NPD5298	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5759	Approved
0.7101	Intermediate Similarity	NPD5162	Approved
0.7086	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3029	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD747	Discontinued
0.7078	Intermediate Similarity	NPD2887	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6839	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5264	Approved
0.7059	Intermediate Similarity	NPD5265	Approved
0.7044	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2022	Approved
0.7031	Intermediate Similarity	NPD9566	Approved
0.7029	Intermediate Similarity	NPD7508	Discontinued
0.7025	Intermediate Similarity	NPD8315	Phase 1
0.7024	Intermediate Similarity	NPD8362	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7599	Phase 2
0.7019	Intermediate Similarity	NPD4566	Approved
0.7019	Intermediate Similarity	NPD4567	Approved
0.7014	Intermediate Similarity	NPD3125	Approved
0.7007	Intermediate Similarity	NPD2047	Approved
0.7007	Intermediate Similarity	NPD21	Approved
0.7007	Intermediate Similarity	NPD2048	Approved
0.7007	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2046	Approved
0.7007	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2051	Approved
0.7007	Intermediate Similarity	NPD2044	Approved
0.7007	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2045	Approved
0.7007	Intermediate Similarity	NPD2043	Approved
0.7006	Intermediate Similarity	NPD7613	Discontinued
0.7	Intermediate Similarity	NPD7105	Phase 1
0.7	Intermediate Similarity	NPD8125	Discontinued
0.7	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2437	Approved
0.6993	Remote Similarity	NPD2436	Approved
0.6992	Remote Similarity	NPD7130	Phase 3
0.6987	Remote Similarity	NPD2014	Approved
0.6987	Remote Similarity	NPD2016	Approved
0.6987	Remote Similarity	NPD2013	Approved
0.6986	Remote Similarity	NPD3626	Phase 3
0.6975	Remote Similarity	NPD7600	Phase 2
0.6974	Remote Similarity	NPD7450	Phase 2
0.697	Remote Similarity	NPD7484	Phase 3
0.697	Remote Similarity	NPD7485	Phase 3
0.695	Remote Similarity	NPD5981	Approved
0.6918	Remote Similarity	NPD3588	Discontinued
0.6917	Remote Similarity	NPD1040	Phase 2
0.6908	Remote Similarity	NPD6864	Phase 2
0.6908	Remote Similarity	NPD6865	Phase 2
0.6899	Remote Similarity	NPD5229	Approved
0.6899	Remote Similarity	NPD5230	Approved
0.6899	Remote Similarity	NPD5638	Approved
0.6899	Remote Similarity	NPD7303	Discontinued
0.6894	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4794	Discontinued
0.6884	Remote Similarity	NPD3598	Phase 3
0.6875	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8265	Approved
0.6846	Remote Similarity	NPD6075	Approved
0.6846	Remote Similarity	NPD6076	Approved
0.6842	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3509	Approved
0.6815	Remote Similarity	NPD3510	Approved
0.6813	Remote Similarity	NPD4648	Approved
0.6813	Remote Similarity	NPD4647	Approved
0.6813	Remote Similarity	NPD4646	Approved
0.6809	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7091	Discontinued
0.6784	Remote Similarity	NPD5774	Approved
0.6784	Remote Similarity	NPD5775	Approved
0.6774	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7744	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1373	Approved
0.6763	Remote Similarity	NPD1374	Approved
0.6763	Remote Similarity	NPD1370	Approved
0.6763	Remote Similarity	NPD1371	Approved
0.6761	Remote Similarity	NPD6093	Discontinued
0.6753	Remote Similarity	NPD7511	Approved
0.6753	Remote Similarity	NPD7512	Approved
0.6739	Remote Similarity	NPD753	Approved
0.6733	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8417	Discontinued
0.6728	Remote Similarity	NPD2891	Approved
0.6727	Remote Similarity	NPD8351	Phase 2
0.6726	Remote Similarity	NPD7608	Discontinued
0.6723	Remote Similarity	NPD7617	Discontinued
0.6721	Remote Similarity	NPD7817	Phase 1
0.6719	Remote Similarity	NPD1812	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