NPASS Compound

Structure

NPC300315 OpenBabel07101719142D 56 58 0 0 1 0 0 0 0 0999 V2000 -1.3121 7.8539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0293 8.0800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6288 8.9371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0885 8.7111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3031 -1.8590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0203 -1.6329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2500 10.0126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0815 1.7895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0901 1.6590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4642 2.7134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4813 2.4524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8555 3.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4066 7.3715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0240 8.2953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3665 6.4798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2552 4.1696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3320 3.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5050 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2360 7.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8354 8.3284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0965 -1.2503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8640 3.3762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7979 6.5781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5731 5.8710 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2638 4.0391 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3320 4.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7979 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 7.3369 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9659 -0.2588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2638 3.0391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5050 5.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5731 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9659 7.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0050 2.0731 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0731 2.0731 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0731 5.0050 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9319 7.0781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0050 5.0050 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9319 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 7.0781 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 -3.3234 4.1696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4066 -0.2934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2552 2.9085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2983 6.4798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4748 7.3715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3665 0.5983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0965 8.3284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8354 -1.2503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6327 9.0887 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 56 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 15 17 1 0 0 0 0 16 47 1 0 0 0 0 17 56 1 0 0 0 0 18 22 1 0 0 0 0 19 25 1 0 0 0 0 20 30 1 0 0 0 0 20 41 1 0 0 0 0 21 31 1 0 0 0 0 21 40 1 0 0 0 0 26 15 1 1 0 0 0 26 35 1 0 0 0 0 26 43 1 0 0 0 0 27 18 1 1 0 0 0 27 36 1 0 0 0 0 27 42 1 0 0 0 0 28 19 1 1 0 0 0 28 34 1 0 0 0 0 28 44 1 0 0 0 0 29 14 1 1 0 0 0 29 37 1 0 0 0 0 29 47 1 0 0 0 0 30 42 2 3 0 0 0 30 48 1 0 0 0 0 31 45 2 3 0 0 0 31 49 1 0 0 0 0 32 23 1 1 0 0 0 32 38 1 0 0 0 0 32 46 1 0 0 0 0 33 24 1 1 0 0 0 33 39 1 0 0 0 0 33 45 1 0 0 0 0 34 40 2 3 0 0 0 34 50 1 0 0 0 0 35 44 2 3 0 0 0 35 51 1 0 0 0 0 36 46 2 3 0 0 0 36 52 1 0 0 0 0 37 41 2 3 0 0 0 37 53 1 0 0 0 0 38 43 2 3 0 0 0 38 54 1 0 0 0 0 39 47 1 0 0 0 0 39 55 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	800.43
Volume:	805.234
LogP:	1.58
LogD:	2.127
LogS:	-3.624
# Rotatable Bonds:	9
TPSA:	234.48
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.194
Synthetic Accessibility Score:	5.798
Fsp3:	0.641
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:	-4.724
MDCK Permeability:	4.145915681874612e-06
Pgp-inhibitor:	0.041
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.885
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	37.321807861328125%
Volume Distribution (VD):	0.575
Pgp-substrate:	57.49943161010742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	1.322
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.529
Skin Sensitization:	0.482
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC300315

Natural Product ID:	NPC300315
*Common Name:**	Planktocyclin
IUPAC Name:	(3S,9S,12S,15S,18S,24S)-9-benzyl-18-(2-methylpropyl)-12-(2-methylsulfanylethyl)-3,15-di(propan-2-yl)-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
Synonyms:	planktocyclin
Standard InCHIKey:	ZMRRRONVXWEVSB-ODNAPOIPSA-N
Standard InCHI:	InChI=1S/C39H60N8O8S/c1-22(2)18-27-36(52)46-32(23(3)4)38(54)43-26(15-17-56-7)35(51)44-28(19-25-12-9-8-10-13-25)34(50)40-21-31(49)45-33(24(5)6)39(55)47-16-11-14-29(47)37(53)41-20-30(48)42-27/h8-10,12-13,22-24,26-29,32-33H,11,14-21H2,1-7H3,(H,40,50)(H,41,53)(H,42,48)(H,43,54)(H,44,51)(H,45,49)(H,46,52)/t26-,27-,28-,29-,32-,33-/m0/s1
SMILES:	CC(C)C[C@H]1C(=N[C@@H](C(C)C)C(=N[C@@H](CCSC)C(=N[C@@H](Cc2ccccc2)C(=NCC(=N[C@@H](C(C)C)C(=O)N2CCC[C@H]2C(=NCC(=N1)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400366
PubChem CID:	23655167
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
NPO12687	Planktothrix rubescens	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17935298]
NPO12687	Planktothrix rubescens	Species	Microcoleaceae	Bacteria	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	5

Activity Type	# Activity
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4211	Individual Protein	Caspase-8	Homo sapiens	IC50	=	93000.0	nM	PMID[529565]
NPT5077	Individual Protein	Cathepsin B	Bos taurus	IC50	>	500000.0	nM	PMID[529565]
NPT1720	Individual Protein	Plasminogen	Homo sapiens	IC50	=	78000.0	nM	PMID[529565]
NPT2	Others	Unspecified		IC50	=	104.0	nM	PMID[529565]
NPT2	Others	Unspecified		IC50	=	10000.0	nM	PMID[529565]

☑ 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 NPC300315 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	139
0.1-0.2	948
0.2-0.3	8885
0.3-0.4	22362
0.4-0.5	8277
0.5-0.6	1353
0.6-0.7	466
0.7-0.8	209
0.8-0.85	33
0.85-0.9	19
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8955	High Similarity	NPC322878
0.8864	High Similarity	NPC89489
0.879	High Similarity	NPC200964
0.873	High Similarity	NPC6975
0.872	High Similarity	NPC202521
0.8692	High Similarity	NPC255447
0.864	High Similarity	NPC476990
0.8583	High Similarity	NPC46427
0.8561	High Similarity	NPC287401
0.855	High Similarity	NPC130309
0.8504	High Similarity	NPC252878
0.848	Intermediate Similarity	NPC470546
0.8468	Intermediate Similarity	NPC470544
0.84	Intermediate Similarity	NPC470545
0.8298	Intermediate Similarity	NPC283783
0.8258	Intermediate Similarity	NPC473322
0.8195	Intermediate Similarity	NPC200589
0.8182	Intermediate Similarity	NPC319766
0.8129	Intermediate Similarity	NPC468984
0.8102	Intermediate Similarity	NPC471264
0.8102	Intermediate Similarity	NPC471265
0.8099	Intermediate Similarity	NPC105717
0.8088	Intermediate Similarity	NPC141050
0.8071	Intermediate Similarity	NPC476978
0.8031	Intermediate Similarity	NPC239357
0.8031	Intermediate Similarity	NPC285926
0.8031	Intermediate Similarity	NPC315276
0.8031	Intermediate Similarity	NPC14672
0.803	Intermediate Similarity	NPC101719
0.7985	Intermediate Similarity	NPC111428
0.7956	Intermediate Similarity	NPC248283
0.7955	Intermediate Similarity	NPC22746
0.7955	Intermediate Similarity	NPC222466
0.7905	Intermediate Similarity	NPC323336
0.7905	Intermediate Similarity	NPC326349
0.7887	Intermediate Similarity	NPC471680
0.7887	Intermediate Similarity	NPC5620
0.7887	Intermediate Similarity	NPC316008
0.7887	Intermediate Similarity	NPC313867
0.7877	Intermediate Similarity	NPC286551
0.7874	Intermediate Similarity	NPC33742
0.7863	Intermediate Similarity	NPC71684
0.7832	Intermediate Similarity	NPC314358
0.7817	Intermediate Similarity	NPC314388
0.7817	Intermediate Similarity	NPC315283
0.7795	Intermediate Similarity	NPC276949
0.7795	Intermediate Similarity	NPC35850
0.7793	Intermediate Similarity	NPC2501
0.7786	Intermediate Similarity	NPC470884
0.7786	Intermediate Similarity	NPC98424
0.7786	Intermediate Similarity	NPC178662
0.7786	Intermediate Similarity	NPC476133
0.7786	Intermediate Similarity	NPC92784
0.7762	Intermediate Similarity	NPC209509
0.774	Intermediate Similarity	NPC7817
0.774	Intermediate Similarity	NPC475168
0.773	Intermediate Similarity	NPC239762
0.773	Intermediate Similarity	NPC163392
0.7692	Intermediate Similarity	NPC52748
0.7676	Intermediate Similarity	NPC269398
0.7676	Intermediate Similarity	NPC263493
0.7676	Intermediate Similarity	NPC476989
0.7671	Intermediate Similarity	NPC129666
0.7655	Intermediate Similarity	NPC16188
0.7639	Intermediate Similarity	NPC315266
0.7635	Intermediate Similarity	NPC261934
0.7635	Intermediate Similarity	NPC5194
0.7635	Intermediate Similarity	NPC56685
0.7635	Intermediate Similarity	NPC202198
0.7635	Intermediate Similarity	NPC122590
0.7622	Intermediate Similarity	NPC77905
0.7622	Intermediate Similarity	NPC161069
0.7612	Intermediate Similarity	NPC175726
0.7612	Intermediate Similarity	NPC474082
0.7606	Intermediate Similarity	NPC476259
0.7584	Intermediate Similarity	NPC470902
0.7557	Intermediate Similarity	NPC254088
0.7552	Intermediate Similarity	NPC168113
0.7535	Intermediate Similarity	NPC132636
0.7533	Intermediate Similarity	NPC469903
0.7532	Intermediate Similarity	NPC317725
0.7532	Intermediate Similarity	NPC317362
0.7532	Intermediate Similarity	NPC326407
0.7532	Intermediate Similarity	NPC318930
0.7517	Intermediate Similarity	NPC262166
0.75	Intermediate Similarity	NPC197682
0.75	Intermediate Similarity	NPC473491
0.75	Intermediate Similarity	NPC176226
0.7483	Intermediate Similarity	NPC471821
0.7483	Intermediate Similarity	NPC471820
0.7466	Intermediate Similarity	NPC262077
0.7465	Intermediate Similarity	NPC127741
0.7465	Intermediate Similarity	NPC68865
0.745	Intermediate Similarity	NPC162104
0.7438	Intermediate Similarity	NPC473501
0.7438	Intermediate Similarity	NPC475439
0.7434	Intermediate Similarity	NPC297145
0.7434	Intermediate Similarity	NPC197743
0.7431	Intermediate Similarity	NPC469426
0.7431	Intermediate Similarity	NPC469427
0.7417	Intermediate Similarity	NPC244509
0.7415	Intermediate Similarity	NPC329761
0.7415	Intermediate Similarity	NPC225648
0.7415	Intermediate Similarity	NPC138775
0.7386	Intermediate Similarity	NPC469898
0.7379	Intermediate Similarity	NPC139326
0.7365	Intermediate Similarity	NPC240848
0.7355	Intermediate Similarity	NPC25565
0.7351	Intermediate Similarity	NPC473002
0.7338	Intermediate Similarity	NPC473003
0.7338	Intermediate Similarity	NPC469902
0.7333	Intermediate Similarity	NPC233702
0.7315	Intermediate Similarity	NPC13470
0.7305	Intermediate Similarity	NPC246079
0.7297	Intermediate Similarity	NPC145113
0.7297	Intermediate Similarity	NPC311658
0.729	Intermediate Similarity	NPC241794
0.7273	Intermediate Similarity	NPC244336
0.7241	Intermediate Similarity	NPC46098
0.7241	Intermediate Similarity	NPC268841
0.7241	Intermediate Similarity	NPC307357
0.7208	Intermediate Similarity	NPC324850
0.7176	Intermediate Similarity	NPC474584
0.7172	Intermediate Similarity	NPC242159
0.7172	Intermediate Similarity	NPC313694
0.7171	Intermediate Similarity	NPC473341
0.7152	Intermediate Similarity	NPC61004
0.7134	Intermediate Similarity	NPC153554
0.7132	Intermediate Similarity	NPC302169
0.7115	Intermediate Similarity	NPC471527
0.7115	Intermediate Similarity	NPC469901
0.7107	Intermediate Similarity	NPC302597
0.7107	Intermediate Similarity	NPC141957
0.7107	Intermediate Similarity	NPC328649
0.7092	Intermediate Similarity	NPC469666
0.7083	Intermediate Similarity	NPC4910
0.7067	Intermediate Similarity	NPC135121
0.7063	Intermediate Similarity	NPC469904
0.7063	Intermediate Similarity	NPC129486
0.7063	Intermediate Similarity	NPC473000
0.7051	Intermediate Similarity	NPC1390
0.7051	Intermediate Similarity	NPC62104
0.7047	Intermediate Similarity	NPC477217
0.7047	Intermediate Similarity	NPC201244
0.7037	Intermediate Similarity	NPC169328
0.7019	Intermediate Similarity	NPC475123
0.7019	Intermediate Similarity	NPC475204
0.6988	Remote Similarity	NPC477637
0.6985	Remote Similarity	NPC310467
0.6985	Remote Similarity	NPC237420
0.6982	Remote Similarity	NPC329731
0.6981	Remote Similarity	NPC217804
0.6981	Remote Similarity	NPC210377
0.6981	Remote Similarity	NPC5719
0.6981	Remote Similarity	NPC22883
0.6977	Remote Similarity	NPC474804
0.6977	Remote Similarity	NPC327481
0.6977	Remote Similarity	NPC474973
0.6977	Remote Similarity	NPC130898
0.6974	Remote Similarity	NPC254798
0.697	Remote Similarity	NPC475013
0.6968	Remote Similarity	NPC476268
0.6962	Remote Similarity	NPC73655
0.6953	Remote Similarity	NPC113326
0.6953	Remote Similarity	NPC194390
0.6953	Remote Similarity	NPC88267
0.6953	Remote Similarity	NPC224610
0.6944	Remote Similarity	NPC325479
0.6937	Remote Similarity	NPC254700
0.6937	Remote Similarity	NPC15068
0.6936	Remote Similarity	NPC184933
0.6936	Remote Similarity	NPC59827
0.6933	Remote Similarity	NPC475532
0.6933	Remote Similarity	NPC137627
0.6918	Remote Similarity	NPC471053
0.6918	Remote Similarity	NPC471051
0.6918	Remote Similarity	NPC471052
0.6899	Remote Similarity	NPC143516
0.6894	Remote Similarity	NPC63040
0.689	Remote Similarity	NPC477462
0.689	Remote Similarity	NPC165285
0.689	Remote Similarity	NPC471165
0.689	Remote Similarity	NPC136797
0.689	Remote Similarity	NPC26108
0.6887	Remote Similarity	NPC81026
0.6884	Remote Similarity	NPC478015
0.6884	Remote Similarity	NPC478016
0.6884	Remote Similarity	NPC478014
0.6884	Remote Similarity	NPC45777
0.6884	Remote Similarity	NPC477061
0.6883	Remote Similarity	NPC300443
0.6875	Remote Similarity	NPC472923
0.6871	Remote Similarity	NPC328494
0.6866	Remote Similarity	NPC476048
0.6864	Remote Similarity	NPC96016
0.6861	Remote Similarity	NPC220698
0.6855	Remote Similarity	NPC161972
0.6855	Remote Similarity	NPC303045
0.6848	Remote Similarity	NPC469900
0.6845	Remote Similarity	NPC161143

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 NPC300315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	106
0.1-0.2	381
0.2-0.3	763
0.3-0.4	2511
0.4-0.5	3813
0.5-0.6	1243
0.6-0.7	250
0.7-0.8	70
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD4125	Approved
0.8672	High Similarity	NPD2585	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD2045	Approved
0.8271	Intermediate Similarity	NPD2048	Approved
0.8271	Intermediate Similarity	NPD21	Approved
0.8271	Intermediate Similarity	NPD2051	Approved
0.8271	Intermediate Similarity	NPD2047	Approved
0.8271	Intermediate Similarity	NPD2043	Approved
0.8271	Intermediate Similarity	NPD2044	Approved
0.8271	Intermediate Similarity	NPD2046	Approved
0.8271	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2022	Approved
0.8168	Intermediate Similarity	NPD5367	Discontinued
0.8129	Intermediate Similarity	NPD2087	Approved
0.8129	Intermediate Similarity	NPD2088	Approved
0.8102	Intermediate Similarity	NPD8173	Phase 2
0.8102	Intermediate Similarity	NPD8172	Phase 2
0.8045	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD5323	Approved
0.7917	Intermediate Similarity	NPD5614	Approved
0.7917	Intermediate Similarity	NPD3987	Approved
0.7917	Intermediate Similarity	NPD5613	Approved
0.7917	Intermediate Similarity	NPD3988	Approved
0.791	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3480	Approved
0.7817	Intermediate Similarity	NPD2436	Approved
0.7817	Intermediate Similarity	NPD2437	Approved
0.7817	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD5299	Approved
0.7786	Intermediate Similarity	NPD4126	Approved
0.7746	Intermediate Similarity	NPD8076	Discontinued
0.7744	Intermediate Similarity	NPD2584	Suspended
0.7698	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD5230	Approved
0.7687	Intermediate Similarity	NPD5229	Approved
0.7664	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4647	Approved
0.7584	Intermediate Similarity	NPD4646	Approved
0.7584	Intermediate Similarity	NPD4648	Approved
0.7571	Intermediate Similarity	NPD8416	Discontinued
0.7566	Intermediate Similarity	NPD4566	Approved
0.7566	Intermediate Similarity	NPD4567	Approved
0.7534	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD8643	Discontinued
0.7517	Intermediate Similarity	NPD5264	Approved
0.7517	Intermediate Similarity	NPD5265	Approved
0.7482	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3072	Approved
0.7481	Intermediate Similarity	NPD3073	Approved
0.7481	Intermediate Similarity	NPD3071	Approved
0.7465	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7828	Discontinued
0.7413	Intermediate Similarity	NPD6901	Phase 3
0.7407	Intermediate Similarity	NPD4761	Approved
0.7407	Intermediate Similarity	NPD4762	Approved
0.7403	Intermediate Similarity	NPD2097	Approved
0.7397	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8126	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8124	Phase 3
0.7338	Intermediate Similarity	NPD4557	Approved
0.7333	Intermediate Similarity	NPD7303	Discontinued
0.7315	Intermediate Similarity	NPD2016	Approved
0.7315	Intermediate Similarity	NPD2014	Approved
0.7315	Intermediate Similarity	NPD2013	Approved
0.7308	Intermediate Similarity	NPD2098	Approved
0.7286	Intermediate Similarity	NPD5263	Approved
0.7286	Intermediate Similarity	NPD4676	Approved
0.7278	Intermediate Similarity	NPD6304	Approved
0.7278	Intermediate Similarity	NPD6303	Approved
0.7239	Intermediate Similarity	NPD6093	Discontinued
0.7233	Intermediate Similarity	NPD4652	Approved
0.7222	Intermediate Similarity	NPD5004	Approved
0.7214	Intermediate Similarity	NPD4177	Approved
0.7214	Intermediate Similarity	NPD4175	Approved
0.7183	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1330	Phase 2
0.7181	Intermediate Similarity	NPD8323	Discontinued
0.7164	Intermediate Similarity	NPD6360	Discontinued
0.7164	Intermediate Similarity	NPD1713	Approved
0.7153	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8303	Discontinued
0.7143	Intermediate Similarity	NPD7965	Phase 2
0.7143	Intermediate Similarity	NPD7964	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3125	Approved
0.7114	Intermediate Similarity	NPD5298	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6073	Approved
0.7103	Intermediate Similarity	NPD5725	Approved
0.7097	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2891	Approved
0.7027	Intermediate Similarity	NPD7720	Phase 2
0.7013	Intermediate Similarity	NPD8315	Phase 1
0.6978	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1582	Approved
0.6974	Remote Similarity	NPD1581	Approved
0.6972	Remote Similarity	NPD5759	Approved
0.6972	Remote Similarity	NPD3040	Approved
0.6972	Remote Similarity	NPD3626	Phase 3
0.6957	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4677	Discontinued
0.6928	Remote Similarity	NPD4432	Discontinued
0.6918	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5780	Phase 2
0.6908	Remote Similarity	NPD3509	Approved
0.6908	Remote Similarity	NPD3510	Approved
0.6903	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD999	Phase 2
0.6897	Remote Similarity	NPD5747	Discontinued
0.6897	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7613	Discontinued
0.6883	Remote Similarity	NPD5638	Approved
0.6857	Remote Similarity	NPD6408	Phase 1
0.685	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7130	Phase 3
0.6842	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7908	Discontinued
0.6815	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3588	Discontinued
0.6781	Remote Similarity	NPD941	Approved
0.6779	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3644	Approved
0.6767	Remote Similarity	NPD3642	Approved
0.6767	Remote Similarity	NPD3643	Approved
0.6763	Remote Similarity	NPD7342	Discontinued
0.6761	Remote Similarity	NPD2031	Discontinued
0.6748	Remote Similarity	NPD2889	Approved
0.6748	Remote Similarity	NPD2017	Approved
0.6748	Remote Similarity	NPD2888	Approved
0.6748	Remote Similarity	NPD2890	Approved
0.6747	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8265	Approved
0.6735	Remote Similarity	NPD4153	Approved
0.6732	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3123	Discovery
0.6715	Remote Similarity	NPD1344	Phase 2
0.6711	Remote Similarity	NPD3508	Approved
0.6708	Remote Similarity	NPD8351	Phase 2
0.6694	Remote Similarity	NPD6690	Approved
0.6685	Remote Similarity	NPD8272	Phase 2
0.6667	Remote Similarity	NPD480	Approved
0.6667	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4151	Approved
0.6667	Remote Similarity	NPD6864	Phase 2
0.6667	Remote Similarity	NPD6865	Phase 2
0.6645	Remote Similarity	NPD6681	Discovery
0.6644	Remote Similarity	NPD4794	Discontinued
0.6643	Remote Similarity	NPD6792	Phase 3
0.6643	Remote Similarity	NPD6325	Discontinued
0.6641	Remote Similarity	NPD1067	Discontinued
0.6623	Remote Similarity	NPD7512	Approved
0.6623	Remote Similarity	NPD7511	Approved
0.6623	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6623	Phase 3
0.6622	Remote Similarity	NPD5272	Discontinued
0.6619	Remote Similarity	NPD2217	Approved
0.6619	Remote Similarity	NPD2218	Phase 2
0.6618	Remote Similarity	NPD3598	Phase 3
0.6607	Remote Similarity	NPD8362	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5581	Approved
0.6585	Remote Similarity	NPD4508	Discontinued
0.6577	Remote Similarity	NPD3908	Approved
0.6575	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5485	Approved
0.6568	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5484	Approved
0.656	Remote Similarity	NPD1812	Approved
0.656	Remote Similarity	NPD1814	Approved
0.6558	Remote Similarity	NPD6676	Phase 2
0.6558	Remote Similarity	NPD1967	Approved
0.6558	Remote Similarity	NPD1968	Approved
0.6552	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7522	Discontinued
0.6545	Remote Similarity	NPD2516	Approved
0.6544	Remote Similarity	NPD3066	Phase 2
0.6544	Remote Similarity	NPD4165	Phase 2
0.6538	Remote Similarity	NPD6088	Approved
0.6522	Remote Similarity	NPD1348	Approved
0.6515	Remote Similarity	NPD1040	Phase 2
0.651	Remote Similarity	NPD5296	Approved
0.6506	Remote Similarity	NPD2517	Approved
0.65	Remote Similarity	NPD8417	Discontinued
0.6496	Remote Similarity	NPD5063	Approved
0.6496	Remote Similarity	NPD5064	Approved
0.6494	Remote Similarity	NPD3919	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