NPASS Compound

Structure

CID316008 OpenBabel06191716132D 52 55 0 0 1 0 0 0 0 0999 V2000 2.3426 7.4481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3574 2.5369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9183 -1.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4033 -5.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1190 -5.6254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0212 6.5012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6805 5.7494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3591 4.8024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0184 4.0506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9745 -0.4604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6531 -1.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3152 0.2914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6970 3.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 -4.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6723 -1.6025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3344 0.0963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4540 -5.1530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3563 2.3518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5981 -4.0089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0023 1.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0321 -1.0457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4972 0.7604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9747 1.6130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9375 -1.6310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8478 -4.2620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0129 -0.8506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3728 -0.2939 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0898 -1.6310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -4.2620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9239 0.3827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0349 1.4049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5549 -3.5549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3920 -0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5549 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0898 -2.6310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 -4.6447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9375 -2.6310 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6942 0.6531 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0706 -1.4359 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9239 -4.6447 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -3.5549 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8478 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0541 1.2098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3863 -4.1104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7327 0.2629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3863 -0.1515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0706 -2.8261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7288 -5.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7288 1.3635 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 6 1 0 0 0 0 5 42 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 18 2 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 27 2 0 0 0 0 16 27 1 0 0 0 0 18 32 1 0 0 0 0 19 43 1 0 0 0 0 20 24 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 44 1 0 0 0 0 23 29 1 0 0 0 0 23 52 1 0 0 0 0 24 2 1 6 0 0 0 25 3 1 1 0 0 0 25 35 1 0 0 0 0 25 39 1 0 0 0 0 26 4 1 1 0 0 0 26 33 1 0 0 0 0 26 42 1 0 0 0 0 28 21 1 1 0 0 0 28 34 1 0 0 0 0 28 40 1 0 0 0 0 29 36 1 0 0 0 0 29 41 1 6 0 0 0 30 17 1 1 0 0 0 30 37 1 0 0 0 0 30 43 1 0 0 0 0 31 20 1 1 0 0 0 31 38 1 0 0 0 0 31 44 1 0 0 0 0 32 40 2 3 0 0 0 32 45 1 0 0 0 0 33 39 2 3 0 0 0 33 46 1 0 0 0 0 34 41 2 3 0 0 0 34 47 1 0 0 0 0 35 44 1 0 0 0 0 35 48 2 0 0 0 0 36 43 1 0 0 0 0 36 49 2 0 0 0 0 37 42 1 0 0 0 0 37 50 2 0 0 0 0 38 51 2 0 0 0 0 38 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	718.37
Volume:	733.606
LogP:	1.043
LogD:	1.135
LogS:	-2.94
# Rotatable Bonds:	10
TPSA:	174.86
# H-Bond Aceptor:	14
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	5.486
Fsp3:	0.526
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:	-5.336
MDCK Permeability:	2.875030622817576e-05
Pgp-inhibitor:	0.973
Pgp-substrate:	0.896
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.895
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	52.732383728027344%
Volume Distribution (VD):	0.241
Pgp-substrate:	48.23086929321289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.146
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.326
CYP2C9-substrate:	0.272
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.772
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	3.717
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.994
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.759
Carcinogencity:	0.089
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.438

Download Data

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

Natural Product: NPC316008

Natural Product ID:	NPC316008
*Common Name:**	ZGRSXMWWGUOTAO-VIEJTCJKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZGRSXMWWGUOTAO-VIEJTCJKSA-N
Standard InCHI:	InChI=1S/C38H50N6O8/c1-6-7-8-9-13-18-32(45)40-28(21-27-15-11-10-12-16-27)34(47)41-29-23-52-38(51)31-20-24(2)22-44(31)35(48)25(3)39-33(46)26(4)42(5)37(50)30-17-14-19-43(30)36(29)49/h6-13,15-16,18,24-26,28-31H,14,17,19-23H2,1-5H3,(H,39,46)(H,40,45)(H,41,47)/b7-6+,9-8+,18-13+/t24-,25+,26+,28+,29+,30+,31+/m1/s1
SMILES:	C/C=C/C=C/C=C/C(=N[C@@H](Cc1ccccc1)C(=N[C@H]1COC(=O)[C@@H]2C[C@@H](C)CN2C(=O)[C@H](C)N=C([C@H](C)N(C)C(=O)[C@@H]2CCCN2C1=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342324
PubChem CID:	24767779
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
NPO795	Streptomyces hawaiiensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25255326]

☑ 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
Kd	1
MIC	3

Activity Type	# Activity
Individual Protein	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5883	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Escherichia coli (strain K12)	Kd	=	300.0	nM	PMID[506302]
NPT4815	Organism	Neisseria meningitidis	Neisseria meningitidis	MIC	=	0.125	ug.mL-1	PMID[506302]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	<	0.0625	ug.mL-1	PMID[506302]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[506302]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	8760.0	nM	PMID[506303]

☑ 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 NPC316008 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	148
0.1-0.2	807
0.2-0.3	3736
0.3-0.4	19518
0.4-0.5	14859
0.5-0.6	2723
0.6-0.7	535
0.7-0.8	274
0.8-0.85	78
0.85-0.9	13
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC313867
0.9925	High Similarity	NPC315283
0.9925	High Similarity	NPC314388
0.9925	High Similarity	NPC314358
0.8889	High Similarity	NPC130309
0.8794	High Similarity	NPC476978
0.8759	High Similarity	NPC287401
0.8705	High Similarity	NPC471264
0.8705	High Similarity	NPC471265
0.8552	High Similarity	NPC240848
0.8542	High Similarity	NPC262077
0.8521	High Similarity	NPC269398
0.8521	High Similarity	NPC263493
0.8511	High Similarity	NPC92784
0.8511	High Similarity	NPC470884
0.8511	High Similarity	NPC98424
0.8511	High Similarity	NPC178662
0.8511	High Similarity	NPC476133
0.8472	Intermediate Similarity	NPC209509
0.8472	Intermediate Similarity	NPC315266
0.8472	Intermediate Similarity	NPC5620
0.8451	Intermediate Similarity	NPC163392
0.8451	Intermediate Similarity	NPC239762
0.8435	Intermediate Similarity	NPC7817
0.8435	Intermediate Similarity	NPC475168
0.837	Intermediate Similarity	NPC6975
0.8333	Intermediate Similarity	NPC161069
0.8276	Intermediate Similarity	NPC52748
0.8267	Intermediate Similarity	NPC470902
0.8264	Intermediate Similarity	NPC469426
0.8264	Intermediate Similarity	NPC469427
0.8255	Intermediate Similarity	NPC162104
0.8243	Intermediate Similarity	NPC2501
0.8243	Intermediate Similarity	NPC129666
0.8231	Intermediate Similarity	NPC145113
0.8222	Intermediate Similarity	NPC202521
0.8207	Intermediate Similarity	NPC176226
0.82	Intermediate Similarity	NPC473341
0.82	Intermediate Similarity	NPC262166
0.8176	Intermediate Similarity	NPC471820
0.8176	Intermediate Similarity	NPC471821
0.8176	Intermediate Similarity	NPC477462
0.8148	Intermediate Similarity	NPC476990
0.8148	Intermediate Similarity	NPC200964
0.8129	Intermediate Similarity	NPC319766
0.8108	Intermediate Similarity	NPC329761
0.8108	Intermediate Similarity	NPC138775
0.8108	Intermediate Similarity	NPC225648
0.8105	Intermediate Similarity	NPC324850
0.8105	Intermediate Similarity	NPC197743
0.8105	Intermediate Similarity	NPC297145
0.8102	Intermediate Similarity	NPC46427
0.8095	Intermediate Similarity	NPC322878
0.8082	Intermediate Similarity	NPC139326
0.8079	Intermediate Similarity	NPC122590
0.8077	Intermediate Similarity	NPC472923
0.8069	Intermediate Similarity	NPC476259
0.8056	Intermediate Similarity	NPC127741
0.8056	Intermediate Similarity	NPC68865
0.8042	Intermediate Similarity	NPC248283
0.8029	Intermediate Similarity	NPC252878
0.8014	Intermediate Similarity	NPC168113
0.8014	Intermediate Similarity	NPC200589
0.7987	Intermediate Similarity	NPC475123
0.7987	Intermediate Similarity	NPC475204
0.7961	Intermediate Similarity	NPC261934
0.7961	Intermediate Similarity	NPC5194
0.7959	Intermediate Similarity	NPC77905
0.7959	Intermediate Similarity	NPC197682
0.7958	Intermediate Similarity	NPC255447
0.7945	Intermediate Similarity	NPC307357
0.7945	Intermediate Similarity	NPC268841
0.7945	Intermediate Similarity	NPC46098
0.7943	Intermediate Similarity	NPC473322
0.7917	Intermediate Similarity	NPC141050
0.7902	Intermediate Similarity	NPC246079
0.7887	Intermediate Similarity	NPC300315
0.7877	Intermediate Similarity	NPC89489
0.7868	Intermediate Similarity	NPC470546
0.7867	Intermediate Similarity	NPC135121
0.7852	Intermediate Similarity	NPC201244
0.7852	Intermediate Similarity	NPC477217
0.7843	Intermediate Similarity	NPC56685
0.7829	Intermediate Similarity	NPC473491
0.7794	Intermediate Similarity	NPC470545
0.7785	Intermediate Similarity	NPC471051
0.7785	Intermediate Similarity	NPC471052
0.7785	Intermediate Similarity	NPC471053
0.7778	Intermediate Similarity	NPC137627
0.7771	Intermediate Similarity	NPC469901
0.7742	Intermediate Similarity	NPC469903
0.773	Intermediate Similarity	NPC26108
0.7727	Intermediate Similarity	NPC202198
0.7721	Intermediate Similarity	NPC470544
0.7707	Intermediate Similarity	NPC469898
0.7702	Intermediate Similarity	NPC473000
0.7697	Intermediate Similarity	NPC105717
0.7665	Intermediate Similarity	NPC470903
0.7665	Intermediate Similarity	NPC470112
0.7665	Intermediate Similarity	NPC167763
0.7658	Intermediate Similarity	NPC469902
0.7654	Intermediate Similarity	NPC40234
0.7647	Intermediate Similarity	NPC283783
0.764	Intermediate Similarity	NPC294516
0.764	Intermediate Similarity	NPC302597
0.764	Intermediate Similarity	NPC107938
0.7632	Intermediate Similarity	NPC311658
0.7628	Intermediate Similarity	NPC244509
0.7622	Intermediate Similarity	NPC471165
0.7606	Intermediate Similarity	NPC101719
0.7595	Intermediate Similarity	NPC1390
0.7595	Intermediate Similarity	NPC62104
0.7591	Intermediate Similarity	NPC239357
0.7566	Intermediate Similarity	NPC81026
0.7547	Intermediate Similarity	NPC471527
0.7546	Intermediate Similarity	NPC46009
0.7536	Intermediate Similarity	NPC169328
0.7535	Intermediate Similarity	NPC222466
0.7517	Intermediate Similarity	NPC132636
0.7516	Intermediate Similarity	NPC16188
0.7515	Intermediate Similarity	NPC136797
0.7515	Intermediate Similarity	NPC476227
0.7515	Intermediate Similarity	NPC279871
0.75	Intermediate Similarity	NPC80150
0.75	Intermediate Similarity	NPC45777
0.75	Intermediate Similarity	NPC266741
0.75	Intermediate Similarity	NPC477061
0.75	Intermediate Similarity	NPC190663
0.75	Intermediate Similarity	NPC241794
0.75	Intermediate Similarity	NPC286551
0.75	Intermediate Similarity	NPC328494
0.75	Intermediate Similarity	NPC230611
0.7485	Intermediate Similarity	NPC475421
0.7484	Intermediate Similarity	NPC244336
0.7482	Intermediate Similarity	NPC237420
0.7482	Intermediate Similarity	NPC310467
0.747	Intermediate Similarity	NPC469900
0.747	Intermediate Similarity	NPC50016
0.7465	Intermediate Similarity	NPC175726
0.7465	Intermediate Similarity	NPC474082
0.7464	Intermediate Similarity	NPC315276
0.7464	Intermediate Similarity	NPC14672
0.7464	Intermediate Similarity	NPC285926
0.7455	Intermediate Similarity	NPC273755
0.7455	Intermediate Similarity	NPC306804
0.7448	Intermediate Similarity	NPC111428
0.7447	Intermediate Similarity	NPC71684
0.744	Intermediate Similarity	NPC472999
0.7438	Intermediate Similarity	NPC114806
0.7436	Intermediate Similarity	NPC233702
0.7423	Intermediate Similarity	NPC141957
0.7417	Intermediate Similarity	NPC476989
0.7413	Intermediate Similarity	NPC22746
0.741	Intermediate Similarity	NPC318930
0.741	Intermediate Similarity	NPC155506
0.741	Intermediate Similarity	NPC159767
0.741	Intermediate Similarity	NPC317362
0.741	Intermediate Similarity	NPC473402
0.741	Intermediate Similarity	NPC317725
0.741	Intermediate Similarity	NPC473354
0.741	Intermediate Similarity	NPC326407
0.7407	Intermediate Similarity	NPC22883
0.7407	Intermediate Similarity	NPC5719
0.7407	Intermediate Similarity	NPC217804
0.7407	Intermediate Similarity	NPC210377
0.7407	Intermediate Similarity	NPC63931
0.7394	Intermediate Similarity	NPC160493
0.7394	Intermediate Similarity	NPC89831
0.7381	Intermediate Similarity	NPC269750
0.7381	Intermediate Similarity	NPC194671
0.7378	Intermediate Similarity	NPC469904
0.7375	Intermediate Similarity	NPC24617
0.7362	Intermediate Similarity	NPC15068
0.7362	Intermediate Similarity	NPC61004
0.7342	Intermediate Similarity	NPC473002
0.7342	Intermediate Similarity	NPC39431
0.7333	Intermediate Similarity	NPC473693
0.7333	Intermediate Similarity	NPC471568
0.7329	Intermediate Similarity	NPC469666
0.7329	Intermediate Similarity	NPC473003
0.7319	Intermediate Similarity	NPC33742
0.7317	Intermediate Similarity	NPC63040
0.7305	Intermediate Similarity	NPC158277
0.7283	Intermediate Similarity	NPC329731
0.7283	Intermediate Similarity	NPC4910
0.7278	Intermediate Similarity	NPC45037
0.7267	Intermediate Similarity	NPC299806
0.726	Intermediate Similarity	NPC239990
0.726	Intermediate Similarity	NPC71933
0.726	Intermediate Similarity	NPC105114
0.726	Intermediate Similarity	NPC89923
0.726	Intermediate Similarity	NPC152850
0.7256	Intermediate Similarity	NPC254700
0.7254	Intermediate Similarity	NPC478016
0.7254	Intermediate Similarity	NPC478015
0.7254	Intermediate Similarity	NPC478014
0.7246	Intermediate Similarity	NPC35850
0.7246	Intermediate Similarity	NPC248670
0.7246	Intermediate Similarity	NPC276949
0.7232	Intermediate Similarity	NPC184933

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 NPC316008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	110
0.1-0.2	331
0.2-0.3	683
0.3-0.4	2216
0.4-0.5	3960
0.5-0.6	1503
0.6-0.7	297
0.7-0.8	45
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.844	Intermediate Similarity	NPD8172	Phase 2
0.844	Intermediate Similarity	NPD8173	Phase 2
0.8235	Intermediate Similarity	NPD2584	Suspended
0.8058	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4177	Approved
0.7943	Intermediate Similarity	NPD4175	Approved
0.7931	Intermediate Similarity	NPD5725	Approved
0.7917	Intermediate Similarity	NPD8416	Discontinued
0.7871	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD6073	Approved
0.7778	Intermediate Similarity	NPD1330	Phase 2
0.7778	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD8076	Discontinued
0.7639	Intermediate Similarity	NPD4125	Approved
0.7622	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD8643	Discontinued
0.7616	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3125	Approved
0.7603	Intermediate Similarity	NPD5747	Discontinued
0.7589	Intermediate Similarity	NPD3073	Approved
0.7589	Intermediate Similarity	NPD3071	Approved
0.7589	Intermediate Similarity	NPD3072	Approved
0.7586	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4762	Approved
0.7518	Intermediate Similarity	NPD4761	Approved
0.7517	Intermediate Similarity	NPD4676	Approved
0.75	Intermediate Similarity	NPD5265	Approved
0.75	Intermediate Similarity	NPD5264	Approved
0.745	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4153	Approved
0.7403	Intermediate Similarity	NPD8323	Discontinued
0.7397	Intermediate Similarity	NPD5263	Approved
0.7362	Intermediate Similarity	NPD8303	Discontinued
0.7351	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD8124	Phase 3
0.7349	Intermediate Similarity	NPD8126	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6901	Phase 3
0.7283	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3588	Discontinued
0.7246	Intermediate Similarity	NPD7964	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7965	Phase 2
0.7233	Intermediate Similarity	NPD8315	Phase 1
0.7215	Intermediate Similarity	NPD7613	Discontinued
0.7215	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6681	Discovery
0.72	Intermediate Similarity	NPD8265	Approved
0.72	Intermediate Similarity	NPD6623	Phase 3
0.72	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5296	Approved
0.7197	Intermediate Similarity	NPD6088	Approved
0.7197	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7512	Approved
0.719	Intermediate Similarity	NPD7511	Approved
0.7181	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6852	Discontinued
0.7171	Intermediate Similarity	NPD4126	Approved
0.7143	Intermediate Similarity	NPD2022	Approved
0.7134	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4646	Approved
0.7125	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4648	Approved
0.7125	Intermediate Similarity	NPD4647	Approved
0.7124	Intermediate Similarity	NPD3480	Approved
0.7117	Intermediate Similarity	NPD4557	Approved
0.7114	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2046	Approved
0.7114	Intermediate Similarity	NPD2043	Approved
0.7114	Intermediate Similarity	NPD2045	Approved
0.7114	Intermediate Similarity	NPD2048	Approved
0.7114	Intermediate Similarity	NPD2047	Approved
0.7114	Intermediate Similarity	NPD21	Approved
0.7114	Intermediate Similarity	NPD2044	Approved
0.7114	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2051	Approved
0.7097	Intermediate Similarity	NPD2436	Approved
0.7097	Intermediate Similarity	NPD2437	Approved
0.7095	Intermediate Similarity	NPD3040	Approved
0.7095	Intermediate Similarity	NPD5759	Approved
0.7092	Intermediate Similarity	NPD5291	Approved
0.7092	Intermediate Similarity	NPD5292	Approved
0.7089	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5323	Approved
0.7078	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2088	Approved
0.7032	Intermediate Similarity	NPD2087	Approved
0.7006	Intermediate Similarity	NPD6676	Phase 2
0.7	Intermediate Similarity	NPD5229	Approved
0.7	Intermediate Similarity	NPD4731	Phase 3
0.7	Intermediate Similarity	NPD5230	Approved
0.7	Intermediate Similarity	NPD4794	Discontinued
0.6993	Remote Similarity	NPD7510	Approved
0.6987	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3988	Approved
0.6981	Remote Similarity	NPD3987	Approved
0.6972	Remote Similarity	NPD3123	Discovery
0.697	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6303	Approved
0.6964	Remote Similarity	NPD6304	Approved
0.6959	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5299	Approved
0.6948	Remote Similarity	NPD6294	Approved
0.6948	Remote Similarity	NPD6295	Approved
0.6944	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4677	Discontinued
0.6928	Remote Similarity	NPD8351	Phase 2
0.6909	Remote Similarity	NPD4567	Approved
0.6909	Remote Similarity	NPD4566	Approved
0.6908	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1348	Approved
0.6899	Remote Similarity	NPD1967	Approved
0.6899	Remote Similarity	NPD1968	Approved
0.6892	Remote Similarity	NPD5367	Discontinued
0.6875	Remote Similarity	NPD2218	Phase 2
0.6875	Remote Similarity	NPD5613	Approved
0.6875	Remote Similarity	NPD5614	Approved
0.6875	Remote Similarity	NPD2217	Approved
0.6872	Remote Similarity	NPD6058	Phase 2
0.6852	Remote Similarity	NPD7131	Phase 3
0.6842	Remote Similarity	NPD4619	Approved
0.6842	Remote Similarity	NPD4621	Approved
0.6829	Remote Similarity	NPD2891	Approved
0.6829	Remote Similarity	NPD8417	Discontinued
0.6821	Remote Similarity	NPD2613	Approved
0.6813	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7599	Phase 2
0.6803	Remote Similarity	NPD2608	Approved
0.6803	Remote Similarity	NPD3132	Approved
0.6803	Remote Similarity	NPD2610	Approved
0.6803	Remote Similarity	NPD4218	Approved
0.6803	Remote Similarity	NPD4216	Approved
0.6803	Remote Similarity	NPD4215	Approved
0.6803	Remote Similarity	NPD2609	Approved
0.6803	Remote Similarity	NPD4217	Approved
0.6803	Remote Similarity	NPD2612	Approved
0.6803	Remote Similarity	NPD2611	Approved
0.6803	Remote Similarity	NPD3131	Approved
0.68	Remote Similarity	NPD4151	Approved
0.6797	Remote Similarity	NPD2570	Approved
0.6797	Remote Similarity	NPD2573	Approved
0.6797	Remote Similarity	NPD3616	Approved
0.6797	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2574	Discontinued
0.6797	Remote Similarity	NPD3614	Approved
0.6797	Remote Similarity	NPD4745	Approved
0.6797	Remote Similarity	NPD3088	Approved
0.6797	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3090	Approved
0.6797	Remote Similarity	NPD4746	Phase 3
0.6797	Remote Similarity	NPD2566	Approved
0.6797	Remote Similarity	NPD3615	Approved
0.6797	Remote Similarity	NPD3089	Approved
0.6797	Remote Similarity	NPD3087	Approved
0.6797	Remote Similarity	NPD2571	Approved
0.6795	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6325	Discontinued
0.677	Remote Similarity	NPD3283	Phase 3
0.677	Remote Similarity	NPD3282	Phase 1
0.6766	Remote Similarity	NPD7600	Phase 2
0.6765	Remote Similarity	NPD7485	Phase 3
0.6765	Remote Similarity	NPD7484	Phase 3
0.6755	Remote Similarity	NPD3664	Approved
0.6755	Remote Similarity	NPD3626	Phase 3
0.6755	Remote Similarity	NPD3663	Approved
0.6755	Remote Similarity	NPD3662	Phase 3
0.6755	Remote Similarity	NPD3661	Approved
0.675	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4652	Approved
0.671	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4686	Approved
0.671	Remote Similarity	NPD4684	Phase 3
0.671	Remote Similarity	NPD4685	Phase 3
0.6709	Remote Similarity	NPD4152	Approved
0.6709	Remote Similarity	NPD7978	Discontinued
0.6709	Remote Similarity	NPD7720	Phase 2
0.6706	Remote Similarity	NPD4508	Discontinued
0.6689	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2098	Approved
0.6667	Remote Similarity	NPD3643	Approved
0.6667	Remote Similarity	NPD2014	Approved
0.6667	Remote Similarity	NPD2013	Approved
0.6667	Remote Similarity	NPD3644	Approved
0.6667	Remote Similarity	NPD4738	Phase 2
0.6667	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2016	Approved
0.6667	Remote Similarity	NPD3642	Approved
0.6667	Remote Similarity	NPD2097	Approved
0.6646	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5581	Approved
0.6623	Remote Similarity	NPD2625	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