NPASS Compound

Structure

NPC473667 OpenBabel07101718302D 49 55 0 0 1 0 0 0 0 0999 V2000 -0.5653 -2.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0567 -0.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4209 -2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6764 -0.0861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4424 1.8328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4206 -1.9731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6718 0.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7781 -0.8670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7575 0.5324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9702 -1.4562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6527 -4.2184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5464 -3.2241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5370 -0.8506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6438 -0.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2348 -1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3385 0.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3130 -0.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3130 0.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9495 -0.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2419 -0.9120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6551 -0.1240 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0559 -1.0512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3277 -0.4715 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2914 -0.8690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8448 -4.8077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3543 -2.6348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9221 0.5561 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0487 0.0691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1527 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5764 0.3328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0352 0.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4161 -0.6103 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5051 -0.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2177 0.7059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1527 -0.6655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9305 -4.4026 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2480 -1.6405 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7685 -1.0356 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9511 -5.8020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2686 -3.0398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9289 1.3425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2707 1.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9427 -0.3336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2221 -0.9188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 -1.7699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8587 0.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5764 1.3328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2273 -0.2411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 45 1 0 0 0 0 3 46 1 0 0 0 0 4 47 1 0 0 0 0 5 48 1 0 0 0 0 6 39 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 10 22 2 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 33 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 16 34 1 0 0 0 0 17 33 1 0 0 0 0 17 39 1 0 0 0 0 18 49 1 0 0 0 0 19 22 1 0 0 0 0 19 31 1 0 0 0 0 20 15 1 6 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 21 35 1 6 0 0 0 22 38 1 0 0 0 0 23 45 1 1 0 0 0 24 35 1 6 0 0 0 24 46 1 0 0 0 0 25 37 2 0 0 0 0 25 40 1 0 0 0 0 26 38 2 3 0 0 0 26 41 1 0 0 0 0 27 28 1 0 0 0 0 27 34 1 6 0 0 0 28 47 1 6 0 0 0 29 30 1 0 0 0 0 29 33 1 6 0 0 0 29 35 1 0 0 0 0 30 36 1 1 0 0 0 30 48 1 0 0 0 0 31 42 2 0 0 0 0 31 49 1 0 0 0 0 32 35 1 1 0 0 0 32 36 1 0 0 0 0 32 39 1 0 0 0 0 33 18 1 6 0 0 0 34 36 1 6 0 0 0 34 43 1 0 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	685.36
Volume:	676.391
LogP:	1.617
LogD:	1.985
LogS:	-3.943
# Rotatable Bonds:	14
TPSA:	179.11
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.233
Synthetic Accessibility Score:	7.081
Fsp3:	0.75
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:	-5.497
MDCK Permeability:	5.109274570713751e-05
Pgp-inhibitor:	0.763
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.366
20% Bioavailability (F20%):	0.327
30% Bioavailability (F30%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	25.712345123291016%
Volume Distribution (VD):	0.449
Pgp-substrate:	51.1530647277832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	4.75
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.458
Human Hepatotoxicity (H-HT):	0.301
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.257
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC473667

Natural Product ID:	NPC473667
*Common Name:**	Avadharidine
IUPAC Name:	n.a.
Synonyms:	Avadharidine
Standard InCHIKey:	ZBALYAJAWGGUCX-RLNVAPDASA-N
Standard InCHI:	InChI=1S/C36H51N3O10/c1-6-39-17-33(18-49-31(42)19-9-7-8-10-22(19)38-26(41)12-11-25(37)40)14-13-24(46-3)35-21-15-20-23(45-2)16-34(43,27(21)28(20)47-4)36(44,32(35)39)30(48-5)29(33)35/h7-10,20-21,23-24,27-30,32,43-44H,6,11-18H2,1-5H3,(H2,37,40)(H,38,41)/t20-,21-,23+,24+,27-,28+,29-,30+,32+,33+,34-,35+,36+/m1/s1
SMILES:	CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7NC(=O)CCC(=O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448609
PubChem CID:	44566469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid alkaloids

*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
NPO33014	delphinium cashmirianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[541686]

☑ 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
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	8.0	bpm	PMID[462965]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	0.0	bpm	PMID[462965]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	5.0	bpm	PMID[462965]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-10.0	bpm	PMID[462965]

☑ 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 NPC473667 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	337
0.1-0.2	1504
0.2-0.3	3318
0.3-0.4	10562
0.4-0.5	19755
0.5-0.6	5766
0.6-0.7	1276
0.7-0.8	136
0.8-0.85	13
0.85-0.9	24
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9849	High Similarity	NPC106593
0.9698	High Similarity	NPC223590
0.9552	High Similarity	NPC140311
0.9307	High Similarity	NPC473837
0.9052	High Similarity	NPC35390
0.9052	High Similarity	NPC473781
0.9052	High Similarity	NPC470631
0.9009	High Similarity	NPC473486
0.9009	High Similarity	NPC475316
0.845	Intermediate Similarity	NPC172769
0.845	Intermediate Similarity	NPC205
0.845	Intermediate Similarity	NPC166521
0.845	Intermediate Similarity	NPC124690
0.845	Intermediate Similarity	NPC184195
0.845	Intermediate Similarity	NPC281470
0.835	Intermediate Similarity	NPC40539
0.8308	Intermediate Similarity	NPC163578
0.8308	Intermediate Similarity	NPC108276
0.7897	Intermediate Similarity	NPC476496
0.7804	Intermediate Similarity	NPC326895
0.7767	Intermediate Similarity	NPC94687
0.7767	Intermediate Similarity	NPC476495
0.7767	Intermediate Similarity	NPC106840
0.77	Intermediate Similarity	NPC475223
0.7664	Intermediate Similarity	NPC246983
0.7664	Intermediate Similarity	NPC475448
0.7403	Intermediate Similarity	NPC475596
0.7403	Intermediate Similarity	NPC475303
0.7403	Intermediate Similarity	NPC316841
0.7401	Intermediate Similarity	NPC127720
0.7401	Intermediate Similarity	NPC127026
0.7382	Intermediate Similarity	NPC475406
0.7371	Intermediate Similarity	NPC30456
0.7371	Intermediate Similarity	NPC21483
0.7371	Intermediate Similarity	NPC198205
0.7368	Intermediate Similarity	NPC471980
0.735	Intermediate Similarity	NPC38959
0.735	Intermediate Similarity	NPC327904
0.7348	Intermediate Similarity	NPC477787
0.7348	Intermediate Similarity	NPC122968
0.7348	Intermediate Similarity	NPC476110
0.7348	Intermediate Similarity	NPC328186
0.7348	Intermediate Similarity	NPC87152
0.7348	Intermediate Similarity	NPC475600
0.7348	Intermediate Similarity	NPC475631
0.7348	Intermediate Similarity	NPC228377
0.7345	Intermediate Similarity	NPC301368
0.7345	Intermediate Similarity	NPC84815
0.7328	Intermediate Similarity	NPC292416
0.7328	Intermediate Similarity	NPC473689
0.7316	Intermediate Similarity	NPC475644
0.7316	Intermediate Similarity	NPC471190
0.7316	Intermediate Similarity	NPC471977
0.7316	Intermediate Similarity	NPC470486
0.7308	Intermediate Similarity	NPC327769
0.7302	Intermediate Similarity	NPC198390
0.7301	Intermediate Similarity	NPC62367
0.7296	Intermediate Similarity	NPC244839
0.7296	Intermediate Similarity	NPC319880
0.7296	Intermediate Similarity	NPC320324
0.7293	Intermediate Similarity	NPC250807
0.7293	Intermediate Similarity	NPC76565
0.7293	Intermediate Similarity	NPC57797
0.729	Intermediate Similarity	NPC476206
0.729	Intermediate Similarity	NPC476205
0.729	Intermediate Similarity	NPC259791
0.729	Intermediate Similarity	NPC476256
0.729	Intermediate Similarity	NPC476257
0.729	Intermediate Similarity	NPC476207
0.729	Intermediate Similarity	NPC476129
0.729	Intermediate Similarity	NPC476212
0.7273	Intermediate Similarity	NPC146824
0.7269	Intermediate Similarity	NPC216428
0.7269	Intermediate Similarity	NPC311054
0.7269	Intermediate Similarity	NPC112752
0.7265	Intermediate Similarity	NPC237702
0.7261	Intermediate Similarity	NPC473850
0.7261	Intermediate Similarity	NPC475137
0.7261	Intermediate Similarity	NPC475498
0.7257	Intermediate Similarity	NPC471016
0.7257	Intermediate Similarity	NPC6981
0.7256	Intermediate Similarity	NPC476218
0.7256	Intermediate Similarity	NPC108804
0.7248	Intermediate Similarity	NPC176371
0.7248	Intermediate Similarity	NPC136573
0.7241	Intermediate Similarity	NPC475362
0.7235	Intermediate Similarity	NPC107828
0.7235	Intermediate Similarity	NPC90358
0.7234	Intermediate Similarity	NPC170751
0.7229	Intermediate Similarity	NPC473506
0.7225	Intermediate Similarity	NPC212768
0.7225	Intermediate Similarity	NPC75600
0.7225	Intermediate Similarity	NPC473115
0.7225	Intermediate Similarity	NPC294579
0.7225	Intermediate Similarity	NPC158020
0.7225	Intermediate Similarity	NPC144779
0.7225	Intermediate Similarity	NPC6576
0.7225	Intermediate Similarity	NPC473089
0.7217	Intermediate Similarity	NPC327699
0.7212	Intermediate Similarity	NPC470306
0.7212	Intermediate Similarity	NPC477907
0.7212	Intermediate Similarity	NPC42678
0.7212	Intermediate Similarity	NPC477909
0.7205	Intermediate Similarity	NPC477912
0.7198	Intermediate Similarity	NPC211920
0.7186	Intermediate Similarity	NPC328154
0.7186	Intermediate Similarity	NPC477902
0.7181	Intermediate Similarity	NPC475408
0.7181	Intermediate Similarity	NPC471014
0.7174	Intermediate Similarity	NPC477788
0.7168	Intermediate Similarity	NPC4421
0.7167	Intermediate Similarity	NPC475648
0.7156	Intermediate Similarity	NPC472553
0.7155	Intermediate Similarity	NPC148860
0.7131	Intermediate Similarity	NPC17160
0.7131	Intermediate Similarity	NPC313720
0.7129	Intermediate Similarity	NPC476750
0.7124	Intermediate Similarity	NPC124029
0.7118	Intermediate Similarity	NPC472555
0.7113	Intermediate Similarity	NPC253482
0.708	Intermediate Similarity	NPC476467
0.7073	Intermediate Similarity	NPC473441
0.7073	Intermediate Similarity	NPC131273
0.707	Intermediate Similarity	NPC473400
0.707	Intermediate Similarity	NPC206211
0.707	Intermediate Similarity	NPC275170
0.707	Intermediate Similarity	NPC306001
0.707	Intermediate Similarity	NPC317882
0.707	Intermediate Similarity	NPC471754
0.707	Intermediate Similarity	NPC471629
0.707	Intermediate Similarity	NPC324251
0.7056	Intermediate Similarity	NPC477903
0.7051	Intermediate Similarity	NPC473458
0.7042	Intermediate Similarity	NPC471583
0.7042	Intermediate Similarity	NPC471782
0.7039	Intermediate Similarity	NPC476749
0.7034	Intermediate Similarity	NPC477906
0.7034	Intermediate Similarity	NPC150698
0.7034	Intermediate Similarity	NPC96801
0.7031	Intermediate Similarity	NPC206343
0.7031	Intermediate Similarity	NPC477908
0.7026	Intermediate Similarity	NPC477911
0.7022	Intermediate Similarity	NPC472550
0.7022	Intermediate Similarity	NPC304179
0.7022	Intermediate Similarity	NPC48042
0.7018	Intermediate Similarity	NPC215892
0.7018	Intermediate Similarity	NPC242662
0.7018	Intermediate Similarity	NPC321072
0.7018	Intermediate Similarity	NPC191193
0.7018	Intermediate Similarity	NPC319128
0.7017	Intermediate Similarity	NPC35208
0.7017	Intermediate Similarity	NPC475426
0.7014	Intermediate Similarity	NPC471512
0.7009	Intermediate Similarity	NPC476436
0.7004	Intermediate Similarity	NPC476429
0.7	Intermediate Similarity	NPC203005
0.7	Intermediate Similarity	NPC278540
0.6991	Remote Similarity	NPC475336
0.6991	Remote Similarity	NPC453583
0.6991	Remote Similarity	NPC473300
0.699	Remote Similarity	NPC469462
0.6987	Remote Similarity	NPC477910
0.6986	Remote Similarity	NPC471606
0.6986	Remote Similarity	NPC181964
0.6986	Remote Similarity	NPC208553
0.6979	Remote Similarity	NPC475601
0.6979	Remote Similarity	NPC14116
0.6979	Remote Similarity	NPC285411
0.6975	Remote Similarity	NPC238278
0.6968	Remote Similarity	NPC472375
0.6968	Remote Similarity	NPC475489
0.6966	Remote Similarity	NPC477900
0.6966	Remote Similarity	NPC477899
0.6964	Remote Similarity	NPC476500
0.6959	Remote Similarity	NPC67246
0.6959	Remote Similarity	NPC33372
0.6957	Remote Similarity	NPC30171
0.6955	Remote Similarity	NPC473558
0.6955	Remote Similarity	NPC473490
0.6953	Remote Similarity	NPC235364
0.6949	Remote Similarity	NPC311196
0.6949	Remote Similarity	NPC134384
0.6943	Remote Similarity	NPC264674
0.6943	Remote Similarity	NPC228331
0.6937	Remote Similarity	NPC472330
0.6937	Remote Similarity	NPC472329
0.6926	Remote Similarity	NPC476090
0.6926	Remote Similarity	NPC311451
0.6909	Remote Similarity	NPC36607
0.6907	Remote Similarity	NPC471513
0.6903	Remote Similarity	NPC63041
0.69	Remote Similarity	NPC51008
0.69	Remote Similarity	NPC41724
0.6897	Remote Similarity	NPC288110
0.6895	Remote Similarity	NPC221687
0.6894	Remote Similarity	NPC26881
0.6893	Remote Similarity	NPC253738
0.6892	Remote Similarity	NPC472392
0.689	Remote Similarity	NPC210415
0.689	Remote Similarity	NPC276993

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 NPC473667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	563
0.2-0.3	768
0.3-0.4	2189
0.4-0.5	3734
0.5-0.6	1596
0.6-0.7	105
0.7-0.8	2
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
0.7746	Intermediate Similarity	NPD7497	Discontinued
0.6986	Remote Similarity	NPD8485	Approved
0.6981	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8435	Approved
0.6866	Remote Similarity	NPD8360	Approved
0.6866	Remote Similarity	NPD8361	Approved
0.6852	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8468	Phase 2
0.6792	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6625	Approved
0.6667	Remote Similarity	NPD6997	Phase 2
0.6652	Remote Similarity	NPD8146	Phase 2
0.6635	Remote Similarity	NPD7795	Phase 2
0.6622	Remote Similarity	NPD6874	Approved
0.6573	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.653	Remote Similarity	NPD8407	Phase 2
0.6514	Remote Similarity	NPD7962	Phase 2
0.65	Remote Similarity	NPD7803	Approved
0.6483	Remote Similarity	NPD7047	Phase 3
0.6473	Remote Similarity	NPD7708	Approved
0.6468	Remote Similarity	NPD8368	Discontinued
0.6466	Remote Similarity	NPD8465	Approved
0.6466	Remote Similarity	NPD8467	Approved
0.6466	Remote Similarity	NPD8466	Approved
0.645	Remote Similarity	NPD8161	Suspended
0.6437	Remote Similarity	NPD5891	Approved
0.6434	Remote Similarity	NPD7955	Approved
0.6434	Remote Similarity	NPD7956	Approved
0.6429	Remote Similarity	NPD7570	Approved
0.6429	Remote Similarity	NPD7569	Approved
0.6426	Remote Similarity	NPD8363	Approved
0.6426	Remote Similarity	NPD7827	Phase 1
0.6426	Remote Similarity	NPD8364	Approved
0.6416	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5928	Phase 1
0.6409	Remote Similarity	NPD7546	Discontinued
0.6404	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD8492	Approved
0.6379	Remote Similarity	NPD6807	Phase 3
0.6377	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.637	Remote Similarity	NPD8426	Approved
0.637	Remote Similarity	NPD8459	Approved
0.637	Remote Similarity	NPD8460	Approved
0.637	Remote Similarity	NPD8425	Approved
0.6368	Remote Similarity	NPD7906	Approved
0.6356	Remote Similarity	NPD8462	Phase 1
0.6355	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8149	Discontinued
0.6343	Remote Similarity	NPD8427	Approved
0.6343	Remote Similarity	NPD8429	Approved
0.6343	Remote Similarity	NPD8428	Approved
0.6341	Remote Similarity	NPD7688	Phase 1
0.6332	Remote Similarity	NPD5609	Approved
0.6332	Remote Similarity	NPD5608	Approved
0.633	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7300	Phase 3
0.6325	Remote Similarity	NPD7302	Phase 3
0.6323	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2974	Approved
0.6316	Remote Similarity	NPD2973	Approved
0.6316	Remote Similarity	NPD2975	Approved
0.6307	Remote Similarity	NPD3437	Discontinued
0.6307	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4580	Approved
0.629	Remote Similarity	NPD6723	Discontinued
0.6287	Remote Similarity	NPD7301	Phase 3
0.6282	Remote Similarity	NPD6296	Discontinued
0.6281	Remote Similarity	NPD7907	Approved
0.6278	Remote Similarity	NPD5036	Approved
0.6277	Remote Similarity	NPD3452	Approved
0.6277	Remote Similarity	NPD2493	Approved
0.6277	Remote Similarity	NPD2494	Approved
0.6277	Remote Similarity	NPD3450	Approved
0.6268	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD4583	Approved
0.6266	Remote Similarity	NPD6770	Approved
0.6266	Remote Similarity	NPD4582	Approved
0.6265	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7565	Approved
0.625	Remote Similarity	NPD5038	Approved
0.625	Remote Similarity	NPD8404	Phase 2
0.625	Remote Similarity	NPD5037	Approved
0.6239	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.623	Remote Similarity	NPD3912	Discontinued
0.6226	Remote Similarity	NPD8367	Approved
0.6225	Remote Similarity	NPD7922	Phase 1
0.6224	Remote Similarity	NPD7292	Approved
0.6223	Remote Similarity	NPD4004	Approved
0.6223	Remote Similarity	NPD4002	Approved
0.6218	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7799	Discontinued
0.6208	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8461	Discontinued
0.6206	Remote Similarity	NPD7417	Discontinued
0.6205	Remote Similarity	NPD3154	Approved
0.6205	Remote Similarity	NPD3153	Approved
0.6197	Remote Similarity	NPD8320	Phase 1
0.6197	Remote Similarity	NPD8319	Approved
0.6193	Remote Similarity	NPD5997	Discontinued
0.6192	Remote Similarity	NPD3794	Approved
0.6192	Remote Similarity	NPD3795	Approved
0.619	Remote Similarity	NPD7810	Phase 3
0.619	Remote Similarity	NPD7811	Phase 3
0.6189	Remote Similarity	NPD6995	Phase 1
0.6188	Remote Similarity	NPD3170	Approved
0.6186	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7683	Discontinued
0.6176	Remote Similarity	NPD7801	Approved
0.6174	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7606	Phase 3
0.6167	Remote Similarity	NPD5042	Phase 1
0.6166	Remote Similarity	NPD7560	Approved
0.6161	Remote Similarity	NPD5742	Approved
0.6161	Remote Similarity	NPD5743	Approved
0.6161	Remote Similarity	NPD5741	Approved
0.616	Remote Similarity	NPD4506	Discontinued
0.6157	Remote Similarity	NPD7256	Discontinued
0.6157	Remote Similarity	NPD7293	Approved
0.6154	Remote Similarity	NPD8059	Phase 3
0.6154	Remote Similarity	NPD7528	Approved
0.6154	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6151	Remote Similarity	NPD7048	Phase 3
0.6147	Remote Similarity	NPD4668	Phase 2
0.6145	Remote Similarity	NPD8067	Phase 3
0.614	Remote Similarity	NPD5937	Approved
0.6137	Remote Similarity	NPD7476	Discontinued
0.6133	Remote Similarity	NPD7921	Approved
0.6132	Remote Similarity	NPD2836	Approved
0.6132	Remote Similarity	NPD2899	Discontinued
0.6132	Remote Similarity	NPD2672	Discontinued
0.613	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.613	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2821	Approved
0.6121	Remote Similarity	NPD8489	Phase 1
0.6116	Remote Similarity	NPD4577	Approved
0.6116	Remote Similarity	NPD4578	Approved
0.6114	Remote Similarity	NPD4121	Phase 3
0.6114	Remote Similarity	NPD4120	Approved
0.6113	Remote Similarity	NPD7186	Phase 3
0.6111	Remote Similarity	NPD8162	Phase 2
0.6111	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5005	Approved
0.6111	Remote Similarity	NPD5430	Discontinued
0.6111	Remote Similarity	NPD7035	Approved
0.6111	Remote Similarity	NPD7036	Phase 3
0.6111	Remote Similarity	NPD5006	Approved
0.6109	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD1945	Phase 1
0.6108	Remote Similarity	NPD1110	Approved
0.6108	Remote Similarity	NPD1109	Approved
0.6106	Remote Similarity	NPD4951	Discontinued
0.6106	Remote Similarity	NPD4663	Approved
0.6104	Remote Similarity	NPD7282	Approved
0.6104	Remote Similarity	NPD6199	Discontinued
0.6099	Remote Similarity	NPD5030	Phase 2
0.6099	Remote Similarity	NPD5031	Approved
0.6099	Remote Similarity	NPD5029	Approved
0.6099	Remote Similarity	NPD5027	Approved
0.6098	Remote Similarity	NPD7279	Phase 2
0.6098	Remote Similarity	NPD7278	Phase 2
0.6098	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7395	Discontinued
0.6091	Remote Similarity	NPD7940	Phase 3
0.6091	Remote Similarity	NPD7878	Phase 2
0.6087	Remote Similarity	NPD7295	Approved
0.6083	Remote Similarity	NPD7225	Discontinued
0.6082	Remote Similarity	NPD7556	Discontinued
0.6081	Remote Similarity	NPD5190	Phase 2
0.6078	Remote Similarity	NPD4420	Approved
0.6077	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD7583	Approved
0.6074	Remote Similarity	NPD5025	Approved
0.6071	Remote Similarity	NPD5028	Approved
0.6071	Remote Similarity	NPD4955	Approved
0.6071	Remote Similarity	NPD5034	Approved
0.6071	Remote Similarity	NPD4954	Approved
0.6071	Remote Similarity	NPD36	Approved
0.6071	Remote Similarity	NPD8281	Discontinued
0.6071	Remote Similarity	NPD5026	Approved
0.607	Remote Similarity	NPD5968	Phase 3
0.6066	Remote Similarity	NPD4665	Approved
0.6066	Remote Similarity	NPD7239	Suspended
0.6066	Remote Similarity	NPD4111	Phase 1
0.6065	Remote Similarity	NPD8008	Approved
0.6065	Remote Similarity	NPD8007	Approved
0.6061	Remote Similarity	NPD5411	Discontinued
0.6059	Remote Similarity	NPD7891	Discontinued
0.6058	Remote Similarity	NPD7236	Approved
0.6055	Remote Similarity	NPD6716	Phase 1
0.6053	Remote Similarity	NPD6836	Approved
0.6053	Remote Similarity	NPD2843	Phase 2

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