NPASS Compound

Structure

CID318299 OpenBabel06191716142D 47 50 0 0 1 0 0 0 0 0999 V2000 -1.7637 -13.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2637 6.8834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 6.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -13.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -12.1692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -11.3032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -10.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -9.5711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -8.7051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -7.8391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -6.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -6.1070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -5.2410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -4.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -3.5089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -2.6429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -1.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -0.9108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5666 2.7966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1324 2.1597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2322 3.4911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3637 2.2173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -0.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7363 5.1513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2363 6.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2637 5.1513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 4.2853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7637 2.5533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7637 6.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4635 3.5487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2363 4.2853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 3.4193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0293 2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 5.1513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 2.5533 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7637 4.2853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 0.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2363 4.2853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7363 3.4193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7363 5.1513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2363 6.0174 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2637 3.4193 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2606 2.8542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 6.0174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 4.2853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7637 0.8212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 1.6872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 29 1 0 0 0 0 3 29 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 30 2 0 0 0 0 22 33 2 0 0 0 0 23 37 1 0 0 0 0 24 25 2 0 0 0 0 24 31 1 0 0 0 0 25 41 1 0 0 0 0 26 29 2 0 0 0 0 26 36 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 28 42 1 0 0 0 0 30 31 1 0 0 0 0 30 33 1 0 0 0 0 31 38 2 0 0 0 0 32 35 1 0 0 0 0 32 39 1 0 0 0 0 33 43 1 0 0 0 0 34 40 1 0 0 0 0 34 44 2 0 0 0 0 35 47 1 0 0 0 0 36 42 2 3 0 0 0 36 45 1 0 0 0 0 37 46 2 0 0 0 0 37 47 1 0 0 0 0 38 39 1 0 0 0 0 38 40 1 0 0 0 0 39 43 2 0 0 0 0 40 41 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	637.39
Volume:	700.047
LogP:	9.232
LogD:	5.385
LogS:	-3.683
# Rotatable Bonds:	21
TPSA:	101.41
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.027
Synthetic Accessibility Score:	3.487
Fsp3:	0.45
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.092
MDCK Permeability:	9.615970157028642e-06
Pgp-inhibitor:	0.875
Pgp-substrate:	0.2
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	101.0074234008789%
Volume Distribution (VD):	0.55
Pgp-substrate:	0.5662271976470947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.363
CYP1A2-substrate:	0.17
CYP2C19-inhibitor:	0.763
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.77
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.598
CYP3A4-inhibitor:	0.634
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	2.069
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.342
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.983
Carcinogencity:	0.11
Eye Corrosion:	0.005
Eye Irritation:	0.027
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC318299

Natural Product ID:	NPC318299
*Common Name:**	Cystodytin H
IUPAC Name:	n.a.
Synonyms:	Cystodytin H
Standard InCHIKey:	VIBRCGDWEDQVOU-VAWYXSNFSA-N
Standard InCHI:	InChI=1S/C40H51N3O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23-37(46)47-35(28-42-36(45)26-29(2)3)32-27-34(44)40-38-31(24-25-41-40)30-21-19-20-22-33(30)43-39(32)38/h11-12,19-22,24-27,35H,4-10,13-18,23,28H2,1-3H3,(H,42,45)/b12-11+
SMILES:	CCCCCCCCC=CCCCCCCCC(=O)OC(CNC(=O)C=C(C)C)C1=CC(=O)C2=NC=CC3=C2C1=NC4=CC=CC=C34
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501765
PubChem CID:	23427221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0001810] Pyridoacridones [CHEMONTID:0002826] Pyrido[2,3,4-kl]acridones

*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
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812214]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20491501]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.08	ug.mL-1	PMID[531294]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.092	ug.mL-1	PMID[531294]

☑ 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 NPC318299 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	302
0.1-0.2	1386
0.2-0.3	6982
0.3-0.4	15355
0.4-0.5	13420
0.5-0.6	2538
0.6-0.7	2242
0.7-0.8	457
0.8-0.85	9
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9947	High Similarity	NPC317752
0.9628	High Similarity	NPC327592
0.9577	High Similarity	NPC317373
0.9316	High Similarity	NPC328318
0.9316	High Similarity	NPC328596
0.8404	Intermediate Similarity	NPC157583
0.8173	Intermediate Similarity	NPC237740
0.8112	Intermediate Similarity	NPC255909
0.8109	Intermediate Similarity	NPC123395
0.8103	Intermediate Similarity	NPC118084
0.8019	Intermediate Similarity	NPC472070
0.8	Intermediate Similarity	NPC207851
0.7961	Intermediate Similarity	NPC472064
0.7953	Intermediate Similarity	NPC322482
0.7824	Intermediate Similarity	NPC216612
0.782	Intermediate Similarity	NPC118940
0.7816	Intermediate Similarity	NPC57398
0.7788	Intermediate Similarity	NPC472065
0.775	Intermediate Similarity	NPC103119
0.7745	Intermediate Similarity	NPC106824
0.7744	Intermediate Similarity	NPC237188
0.7729	Intermediate Similarity	NPC472063
0.7729	Intermediate Similarity	NPC472062
0.7729	Intermediate Similarity	NPC472069
0.7725	Intermediate Similarity	NPC123839
0.7692	Intermediate Similarity	NPC84347
0.767	Intermediate Similarity	NPC284338
0.767	Intermediate Similarity	NPC103361
0.7656	Intermediate Similarity	NPC289086
0.7647	Intermediate Similarity	NPC135950
0.763	Intermediate Similarity	NPC266249
0.7628	Intermediate Similarity	NPC36405
0.7619	Intermediate Similarity	NPC238457
0.761	Intermediate Similarity	NPC472116
0.7593	Intermediate Similarity	NPC312645
0.756	Intermediate Similarity	NPC476874
0.7556	Intermediate Similarity	NPC327769
0.7512	Intermediate Similarity	NPC477908
0.7512	Intermediate Similarity	NPC206343
0.75	Intermediate Similarity	NPC477979
0.7476	Intermediate Similarity	NPC193761
0.7474	Intermediate Similarity	NPC41717
0.7466	Intermediate Similarity	NPC229893
0.7465	Intermediate Similarity	NPC470280
0.7463	Intermediate Similarity	NPC216550
0.7462	Intermediate Similarity	NPC139763
0.7455	Intermediate Similarity	NPC2395
0.7454	Intermediate Similarity	NPC89508
0.7452	Intermediate Similarity	NPC474916
0.7452	Intermediate Similarity	NPC34837
0.7443	Intermediate Similarity	NPC472555
0.7442	Intermediate Similarity	NPC82370
0.744	Intermediate Similarity	NPC245916
0.7426	Intermediate Similarity	NPC282103
0.7416	Intermediate Similarity	NPC81535
0.7409	Intermediate Similarity	NPC477901
0.7399	Intermediate Similarity	NPC473506
0.7395	Intermediate Similarity	NPC470020
0.7385	Intermediate Similarity	NPC42678
0.7385	Intermediate Similarity	NPC477907
0.7385	Intermediate Similarity	NPC477909
0.7376	Intermediate Similarity	NPC284559
0.7373	Intermediate Similarity	NPC221100
0.7373	Intermediate Similarity	NPC234078
0.7368	Intermediate Similarity	NPC67288
0.7366	Intermediate Similarity	NPC228377
0.7366	Intermediate Similarity	NPC328186
0.7366	Intermediate Similarity	NPC476110
0.7366	Intermediate Similarity	NPC475258
0.7366	Intermediate Similarity	NPC122968
0.7366	Intermediate Similarity	NPC476491
0.7366	Intermediate Similarity	NPC475600
0.7366	Intermediate Similarity	NPC469489
0.7366	Intermediate Similarity	NPC475631
0.7366	Intermediate Similarity	NPC87152
0.7366	Intermediate Similarity	NPC477787
0.7364	Intermediate Similarity	NPC216428
0.7358	Intermediate Similarity	NPC165599
0.7354	Intermediate Similarity	NPC235885
0.7354	Intermediate Similarity	NPC477900
0.7354	Intermediate Similarity	NPC477899
0.7353	Intermediate Similarity	NPC472323
0.7352	Intermediate Similarity	NPC472285
0.7345	Intermediate Similarity	NPC475596
0.7345	Intermediate Similarity	NPC475303
0.7345	Intermediate Similarity	NPC316841
0.7343	Intermediate Similarity	NPC103230
0.7342	Intermediate Similarity	NPC477911
0.7342	Intermediate Similarity	NPC477788
0.7342	Intermediate Similarity	NPC235364
0.7339	Intermediate Similarity	NPC478157
0.7337	Intermediate Similarity	NPC203754
0.7337	Intermediate Similarity	NPC150048
0.7336	Intermediate Similarity	NPC315545
0.7336	Intermediate Similarity	NPC193238
0.7336	Intermediate Similarity	NPC314297
0.7336	Intermediate Similarity	NPC15801
0.7333	Intermediate Similarity	NPC470486
0.7333	Intermediate Similarity	NPC471190
0.7333	Intermediate Similarity	NPC471977
0.7333	Intermediate Similarity	NPC475644
0.733	Intermediate Similarity	NPC473763
0.733	Intermediate Similarity	NPC117244
0.7327	Intermediate Similarity	NPC143533
0.7324	Intermediate Similarity	NPC314648
0.7321	Intermediate Similarity	NPC909
0.7321	Intermediate Similarity	NPC470018
0.7321	Intermediate Similarity	NPC475338
0.7318	Intermediate Similarity	NPC281049
0.7318	Intermediate Similarity	NPC473310
0.7318	Intermediate Similarity	NPC62367
0.7318	Intermediate Similarity	NPC314270
0.7315	Intermediate Similarity	NPC309845
0.7313	Intermediate Similarity	NPC30456
0.7309	Intermediate Similarity	NPC250807
0.7309	Intermediate Similarity	NPC76565
0.7309	Intermediate Similarity	NPC57797
0.7304	Intermediate Similarity	NPC194040
0.7299	Intermediate Similarity	NPC470279
0.7291	Intermediate Similarity	NPC472119
0.729	Intermediate Similarity	NPC315638
0.729	Intermediate Similarity	NPC314855
0.729	Intermediate Similarity	NPC313796
0.729	Intermediate Similarity	NPC313345
0.7289	Intermediate Similarity	NPC74575
0.7286	Intermediate Similarity	NPC149708
0.7281	Intermediate Similarity	NPC70155
0.7277	Intermediate Similarity	NPC475137
0.7277	Intermediate Similarity	NPC26881
0.7277	Intermediate Similarity	NPC475498
0.7277	Intermediate Similarity	NPC473850
0.7273	Intermediate Similarity	NPC249614
0.7273	Intermediate Similarity	NPC109922
0.7269	Intermediate Similarity	NPC478158
0.7269	Intermediate Similarity	NPC292416
0.7269	Intermediate Similarity	NPC260434
0.7269	Intermediate Similarity	NPC473689
0.7269	Intermediate Similarity	NPC477906
0.7268	Intermediate Similarity	NPC322644
0.7261	Intermediate Similarity	NPC472061
0.7256	Intermediate Similarity	NPC244741
0.7256	Intermediate Similarity	NPC475835
0.7251	Intermediate Similarity	NPC74413
0.7251	Intermediate Similarity	NPC474767
0.7249	Intermediate Similarity	NPC475406
0.7248	Intermediate Similarity	NPC292517
0.7246	Intermediate Similarity	NPC138370
0.7244	Intermediate Similarity	NPC319232
0.7244	Intermediate Similarity	NPC24370
0.7243	Intermediate Similarity	NPC132539
0.7238	Intermediate Similarity	NPC227582
0.7237	Intermediate Similarity	NPC49547
0.7237	Intermediate Similarity	NPC319880
0.7237	Intermediate Similarity	NPC320324
0.7237	Intermediate Similarity	NPC244839
0.7235	Intermediate Similarity	NPC314834
0.723	Intermediate Similarity	NPC260900
0.7228	Intermediate Similarity	NPC15840
0.7228	Intermediate Similarity	NPC471997
0.7227	Intermediate Similarity	NPC207531
0.7225	Intermediate Similarity	NPC91125
0.7222	Intermediate Similarity	NPC258062
0.7222	Intermediate Similarity	NPC208522
0.7222	Intermediate Similarity	NPC127677
0.722	Intermediate Similarity	NPC477903
0.722	Intermediate Similarity	NPC66210
0.722	Intermediate Similarity	NPC235684
0.722	Intermediate Similarity	NPC477912
0.7217	Intermediate Similarity	NPC38959
0.7217	Intermediate Similarity	NPC327904
0.7217	Intermediate Similarity	NPC252338
0.7215	Intermediate Similarity	NPC236668
0.7215	Intermediate Similarity	NPC165837
0.7212	Intermediate Similarity	NPC186351
0.7212	Intermediate Similarity	NPC146824
0.721	Intermediate Similarity	NPC72905
0.7207	Intermediate Similarity	NPC301368
0.7207	Intermediate Similarity	NPC84815
0.7206	Intermediate Similarity	NPC258480
0.7205	Intermediate Similarity	NPC237702
0.72	Intermediate Similarity	NPC477902
0.7198	Intermediate Similarity	NPC83111
0.7196	Intermediate Similarity	NPC98715
0.7195	Intermediate Similarity	NPC469727
0.7193	Intermediate Similarity	NPC267853
0.719	Intermediate Similarity	NPC128244
0.7189	Intermediate Similarity	NPC304179
0.7189	Intermediate Similarity	NPC271862
0.7189	Intermediate Similarity	NPC48042
0.7189	Intermediate Similarity	NPC472550
0.7188	Intermediate Similarity	NPC127026
0.7188	Intermediate Similarity	NPC127720
0.7182	Intermediate Similarity	NPC4421
0.7182	Intermediate Similarity	NPC146976
0.7182	Intermediate Similarity	NPC264674
0.7181	Intermediate Similarity	NPC475362
0.7179	Intermediate Similarity	NPC142385
0.7177	Intermediate Similarity	NPC267343
0.7177	Intermediate Similarity	NPC269886
0.7177	Intermediate Similarity	NPC472295

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 NPC318299 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	529
0.2-0.3	661
0.3-0.4	1506
0.4-0.5	2778
0.5-0.6	2204
0.6-0.7	1102
0.7-0.8	186
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
0.7877	Intermediate Similarity	NPD3394	Approved
0.7877	Intermediate Similarity	NPD3389	Approved
0.7877	Intermediate Similarity	NPD3393	Approved
0.7867	Intermediate Similarity	NPD3795	Approved
0.7867	Intermediate Similarity	NPD3794	Approved
0.7798	Intermediate Similarity	NPD8289	Discontinued
0.7703	Intermediate Similarity	NPD7001	Phase 3
0.7624	Intermediate Similarity	NPD8063	Discontinued
0.761	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7608	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD5475	Discontinued
0.7604	Intermediate Similarity	NPD7404	Approved
0.7585	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2510	Approved
0.7547	Intermediate Similarity	NPD2509	Approved
0.7547	Intermediate Similarity	NPD7666	Phase 3
0.7547	Intermediate Similarity	NPD7665	Phase 2
0.7536	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7010	Phase 3
0.7524	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD5891	Approved
0.7489	Intermediate Similarity	NPD3280	Approved
0.7488	Intermediate Similarity	NPD7234	Approved
0.7488	Intermediate Similarity	NPD3947	Discontinued
0.7488	Intermediate Similarity	NPD7233	Approved
0.7488	Intermediate Similarity	NPD5901	Discontinued
0.7452	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD8325	Phase 3
0.7431	Intermediate Similarity	NPD8326	Phase 3
0.7431	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD7688	Phase 1
0.7416	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6999	Discontinued
0.7415	Intermediate Similarity	NPD2336	Approved
0.7406	Intermediate Similarity	NPD6987	Phase 1
0.7391	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6479	Discontinued
0.7371	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5862	Discovery
0.7343	Intermediate Similarity	NPD4526	Approved
0.7343	Intermediate Similarity	NPD4529	Approved
0.7343	Intermediate Similarity	NPD4528	Approved
0.7327	Intermediate Similarity	NPD7069	Discontinued
0.7324	Intermediate Similarity	NPD8114	Approved
0.7324	Intermediate Similarity	NPD8115	Approved
0.7324	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7944	Discontinued
0.7302	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5088	Discontinued
0.7281	Intermediate Similarity	NPD7470	Discontinued
0.7273	Intermediate Similarity	NPD2307	Discontinued
0.7269	Intermediate Similarity	NPD6529	Discontinued
0.7264	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5482	Discontinued
0.7241	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8430	Approved
0.7212	Intermediate Similarity	NPD5505	Discontinued
0.7198	Intermediate Similarity	NPD6281	Approved
0.7195	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8356	Approved
0.7184	Intermediate Similarity	NPD4948	Discontinued
0.7183	Intermediate Similarity	NPD7727	Phase 2
0.7182	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD1996	Discontinued
0.7173	Intermediate Similarity	NPD8101	Phase 3
0.7169	Intermediate Similarity	NPD4852	Phase 2
0.7168	Intermediate Similarity	NPD7426	Phase 1
0.7162	Intermediate Similarity	NPD7395	Discontinued
0.7162	Intermediate Similarity	NPD7878	Phase 2
0.7162	Intermediate Similarity	NPD4429	Discontinued
0.7156	Intermediate Similarity	NPD5003	Discontinued
0.7156	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4334	Discontinued
0.715	Intermediate Similarity	NPD750	Phase 2
0.7149	Intermediate Similarity	NPD5022	Discontinued
0.7149	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4602	Approved
0.713	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7957	Phase 1
0.713	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7885	Phase 2
0.7124	Intermediate Similarity	NPD7886	Phase 2
0.7124	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7778	Approved
0.7123	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7777	Approved
0.7123	Intermediate Similarity	NPD53	Approved
0.7122	Intermediate Similarity	NPD6178	Phase 3
0.7122	Intermediate Similarity	NPD2091	Phase 2
0.7122	Intermediate Similarity	NPD2096	Phase 2
0.7122	Intermediate Similarity	NPD7564	Discontinued
0.7119	Intermediate Similarity	NPD8100	Phase 3
0.7104	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6790	Phase 1
0.7091	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5104	Approved
0.7077	Intermediate Similarity	NPD2581	Approved
0.7077	Intermediate Similarity	NPD2582	Approved
0.7075	Intermediate Similarity	NPD6206	Phase 1
0.7073	Intermediate Similarity	NPD2094	Phase 2
0.7073	Intermediate Similarity	NPD2092	Phase 2
0.7073	Intermediate Similarity	NPD2095	Phase 2
0.7061	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5888	Phase 2
0.7056	Intermediate Similarity	NPD7790	Approved
0.7056	Intermediate Similarity	NPD7950	Approved
0.7056	Intermediate Similarity	NPD7791	Approved
0.7056	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7951	Approved
0.7056	Intermediate Similarity	NPD7789	Approved
0.7056	Intermediate Similarity	NPD4500	Approved
0.7056	Intermediate Similarity	NPD7952	Approved
0.7056	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7953	Approved
0.7056	Intermediate Similarity	NPD4501	Approved
0.7048	Intermediate Similarity	NPD4376	Phase 3
0.7048	Intermediate Similarity	NPD6569	Phase 2
0.7046	Intermediate Similarity	NPD8468	Phase 2
0.7045	Intermediate Similarity	NPD4417	Approved
0.7044	Intermediate Similarity	NPD8123	Approved
0.7044	Intermediate Similarity	NPD8122	Approved
0.7042	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1096	Discontinued
0.7037	Intermediate Similarity	NPD6176	Phase 1
0.7035	Intermediate Similarity	NPD6995	Phase 1
0.7033	Intermediate Similarity	NPD2564	Approved
0.7033	Intermediate Similarity	NPD2565	Phase 2
0.703	Intermediate Similarity	NPD482	Approved
0.7027	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7817	Phase 1
0.7022	Intermediate Similarity	NPD8479	Phase 2
0.7014	Intermediate Similarity	NPD3330	Phase 1
0.7005	Intermediate Similarity	NPD6227	Discontinued
0.7004	Intermediate Similarity	NPD3222	Phase 2
0.7	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8091	Phase 3
0.6995	Remote Similarity	NPD5100	Phase 3
0.6995	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7731	Approved
0.6987	Remote Similarity	NPD6165	Phase 2
0.6987	Remote Similarity	NPD3259	Approved
0.6987	Remote Similarity	NPD6164	Phase 2
0.6987	Remote Similarity	NPD7730	Approved
0.6983	Remote Similarity	NPD8247	Approved
0.6983	Remote Similarity	NPD8246	Approved
0.6982	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4427	Phase 2
0.6978	Remote Similarity	NPD6770	Approved
0.6977	Remote Similarity	NPD4600	Approved
0.6977	Remote Similarity	NPD4601	Approved
0.6977	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7568	Phase 1
0.6971	Remote Similarity	NPD5809	Phase 3
0.6971	Remote Similarity	NPD3315	Phase 3
0.6968	Remote Similarity	NPD5416	Discontinued
0.6967	Remote Similarity	NPD4315	Phase 2
0.6967	Remote Similarity	NPD6665	Discontinued
0.6964	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5450	Discontinued
0.6963	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6642	Approved
0.6961	Remote Similarity	NPD6641	Approved
0.6959	Remote Similarity	NPD4886	Phase 2
0.6959	Remote Similarity	NPD5487	Phase 1
0.6954	Remote Similarity	NPD5255	Approved
0.6952	Remote Similarity	NPD4499	Approved
0.6951	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5512	Phase 3
0.6947	Remote Similarity	NPD6242	Discontinued
0.6944	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8463	Approved
0.6942	Remote Similarity	NPD8408	Discontinued
0.6942	Remote Similarity	NPD3178	Discontinued
0.6941	Remote Similarity	NPD7562	Approved
0.6938	Remote Similarity	NPD8021	Approved
0.6938	Remote Similarity	NPD8020	Approved
0.6935	Remote Similarity	NPD6635	Approved
0.6933	Remote Similarity	NPD7921	Approved
0.693	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4037	Approved
0.6927	Remote Similarity	NPD4122	Approved
0.6927	Remote Similarity	NPD31	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