NPASS Compound

Structure

CID22115 OpenBabel06191715352D 45 51 0 0 1 0 0 0 0 0999 V2000 2.4185 -4.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2816 -1.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1823 -5.0019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 1.7776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6169 1.8881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3846 -3.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6587 -2.6652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1987 -2.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6149 -3.2951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2846 -1.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2703 0.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2846 -2.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7754 0.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1412 -3.9079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9574 -2.9201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1507 -3.3218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1676 -1.5171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3422 0.8477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6865 -1.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5595 -3.7356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1936 -2.2383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -1.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5714 0.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 -1.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8569 -3.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4908 -3.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 -2.7224 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8828 -0.8541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7513 -3.1930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0951 -3.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 0.2776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6865 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8021 0.8949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3777 -0.3387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4913 0.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7205 -0.0406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -3.2224 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5816 -0.6743 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5669 -2.6144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5049 0.5377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2495 -4.6416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 1.2776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3793 1.8011 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 38 1 0 0 0 0 2 39 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 44 1 0 0 0 0 6 8 2 0 0 0 0 6 21 1 0 0 0 0 7 9 2 0 0 0 0 7 22 1 0 0 0 0 8 30 1 0 0 0 0 9 31 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 38 1 0 0 0 0 13 39 1 0 0 0 0 14 21 2 0 0 0 0 14 26 1 0 0 0 0 15 22 2 0 0 0 0 15 27 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 32 1 0 0 0 0 19 24 2 0 0 0 0 19 34 1 0 0 0 0 20 25 2 0 0 0 0 20 33 1 0 0 0 0 23 25 1 0 0 0 0 24 35 1 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 26 30 2 0 0 0 0 27 31 2 0 0 0 0 28 16 1 6 0 0 0 28 38 1 0 0 0 0 29 17 1 6 0 0 0 29 35 1 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 31 42 1 0 0 0 0 32 33 2 0 0 0 0 32 43 1 0 0 0 0 33 45 1 0 0 0 0 34 36 2 0 0 0 0 34 44 1 0 0 0 0 35 37 2 0 0 0 0 36 37 1 0 0 0 0 36 41 1 0 0 0 0 37 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.29
Volume:	631.71
LogP:	5.932
LogD:	3.906
LogS:	-3.84
# Rotatable Bonds:	3
TPSA:	83.86
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	5.664
Fsp3:	0.351
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:	-5.619
MDCK Permeability:	2.036158912233077e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.452
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.843
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	83.9190444946289%
Volume Distribution (VD):	1.301
Pgp-substrate:	15.482457160949707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.52
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.959
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.949

ADMET: Excretion

Clearance (CL):	10.016
Half-life (T1/2):	0.398

ADMET: Toxicity

hERG Blockers:	0.946
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.543
AMES Toxicity:	0.116
Rat Oral Acute Toxicity:	0.305
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.866
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.386

Download Data

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

Natural Product: NPC22115

Natural Product ID:	NPC22115
*Common Name:**	Antioquine
IUPAC Name:	n.a.
Synonyms:	Antioquine
Standard InCHIKey:	MNNXIEANPHEHSB-WDYNHAJCSA-N
Standard InCHI:	InChI=1S/C37H40N2O6/c1-38-12-10-23-18-32(43-4)33-20-25(23)28(38)16-21-6-8-30(40)26(14-21)27-15-22(7-9-31(27)42-3)17-29-35-24(11-13-39(29)2)19-34(44-5)36(41)37(35)45-33/h6-9,14-15,18-20,28-29,40-41H,10-13,16-17H2,1-5H3/t28-,29+/m1/s1
SMILES:	COc1cc2CCN([C@@H]3c2c(c1O)Oc1cc2c(cc1OC)CCN([C@@H]2Cc1cc(c2cc(C3)ccc2OC)c(O)cc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452904
PubChem CID:	10393931
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO16121	Pestalotiopsis disseminata	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643036]
NPO8786	Acanthella costata	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19243956]
NPO8786	Acanthella costata	Species	Melastomataceae	Eukaryota	n.a.	(25 m) at Sykes Reef (Capricorn-Bunker Group Great Barrier Reef), Australia	n.a.	PMID[19243956]
NPO16121	Pestalotiopsis disseminata	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26641923]
NPO33281	pseuhxandra sclerocarpa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8676127]
NPO16121	Pestalotiopsis disseminata	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12469	Swainsona procumbens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14287	Alnus formosana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8786	Acanthella costata	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15692	Lampropeltis getula	Species	Colubridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13306	Choisya ternata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9429	Dalbergia sissoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5828	Conger vulgaris	Species	Congridae	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	4
Others	2

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	IC50	=	4.06	ug.mL-1	PMID[501270]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	460.0	ug.mL-1	PMID[501270]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	548.5	ug.mL-1	PMID[501270]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	3400.0	nM	PMID[501271]
NPT2	Others	Unspecified		Ratio IC50	=	29.4	n.a.	PMID[501271]
NPT2	Others	Unspecified		Ratio IC50	=	0.9	n.a.	PMID[501271]

☑ 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 NPC22115 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	365
0.1-0.2	1667
0.2-0.3	8007
0.3-0.4	10341
0.4-0.5	5118
0.5-0.6	7924
0.6-0.7	7369
0.7-0.8	1545
0.8-0.85	172
0.85-0.9	90
0.9-0.95	49
0.95-1	50

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC275680
0.9881	High Similarity	NPC302245
0.9881	High Similarity	NPC95426
0.9881	High Similarity	NPC16357
0.9822	High Similarity	NPC139783
0.9822	High Similarity	NPC65312
0.9762	High Similarity	NPC8836
0.9762	High Similarity	NPC290582
0.9762	High Similarity	NPC54654
0.9762	High Similarity	NPC104196
0.9762	High Similarity	NPC251735
0.9762	High Similarity	NPC271013
0.9762	High Similarity	NPC311973
0.9762	High Similarity	NPC7715
0.9762	High Similarity	NPC49075
0.9762	High Similarity	NPC217748
0.9762	High Similarity	NPC279228
0.9762	High Similarity	NPC15414
0.9762	High Similarity	NPC90998
0.9762	High Similarity	NPC182052
0.9762	High Similarity	NPC42663
0.9762	High Similarity	NPC239824
0.9762	High Similarity	NPC285931
0.9762	High Similarity	NPC229373
0.9762	High Similarity	NPC223690
0.9762	High Similarity	NPC258657
0.9762	High Similarity	NPC290005
0.9762	High Similarity	NPC222661
0.9762	High Similarity	NPC181796
0.9762	High Similarity	NPC328155
0.9762	High Similarity	NPC185639
0.9708	High Similarity	NPC206900
0.9706	High Similarity	NPC116465
0.9706	High Similarity	NPC212237
0.9704	High Similarity	NPC167116
0.9704	High Similarity	NPC274716
0.9704	High Similarity	NPC254441
0.9702	High Similarity	NPC286119
0.9645	High Similarity	NPC30779
0.9595	High Similarity	NPC478093
0.954	High Similarity	NPC473589
0.954	High Similarity	NPC256124
0.954	High Similarity	NPC30182
0.954	High Similarity	NPC478091
0.954	High Similarity	NPC478092
0.948	High Similarity	NPC274661
0.948	High Similarity	NPC48490
0.948	High Similarity	NPC82457
0.948	High Similarity	NPC11296
0.948	High Similarity	NPC175890
0.9425	High Similarity	NPC191132
0.9425	High Similarity	NPC60295
0.9371	High Similarity	NPC24260
0.9345	High Similarity	NPC317145
0.9345	High Similarity	NPC115284
0.9345	High Similarity	NPC276890
0.9345	High Similarity	NPC317439
0.9345	High Similarity	NPC63646
0.9345	High Similarity	NPC198498
0.9345	High Similarity	NPC76682
0.9345	High Similarity	NPC227060
0.9345	High Similarity	NPC10908
0.9294	High Similarity	NPC293093
0.929	High Similarity	NPC41376
0.929	High Similarity	NPC129518
0.929	High Similarity	NPC251580
0.929	High Similarity	NPC12424
0.9138	High Similarity	NPC302275
0.9121	High Similarity	NPC254581
0.9107	High Similarity	NPC317272
0.9107	High Similarity	NPC264850
0.9107	High Similarity	NPC42549
0.9107	High Similarity	NPC240841
0.9107	High Similarity	NPC13916
0.9107	High Similarity	NPC256012
0.9107	High Similarity	NPC250846
0.9107	High Similarity	NPC268503
0.9101	High Similarity	NPC85381
0.9096	High Similarity	NPC318805
0.9096	High Similarity	NPC41122
0.9075	High Similarity	NPC243454
0.9075	High Similarity	NPC475479
0.9061	High Similarity	NPC475654
0.9048	High Similarity	NPC24465
0.9034	High Similarity	NPC47077
0.9034	High Similarity	NPC14507
0.9023	High Similarity	NPC239584
0.9	High Similarity	NPC234318
0.9	High Similarity	NPC83198
0.9	High Similarity	NPC204908
0.8971	High Similarity	NPC73492
0.8971	High Similarity	NPC299990
0.8953	High Similarity	NPC232386
0.8953	High Similarity	NPC152680
0.8953	High Similarity	NPC190783
0.8895	High Similarity	NPC239775
0.8837	High Similarity	NPC168753
0.8837	High Similarity	NPC118274
0.8786	High Similarity	NPC108434
0.8786	High Similarity	NPC475215
0.8764	High Similarity	NPC249996
0.8722	High Similarity	NPC281581
0.8721	High Similarity	NPC117188
0.8721	High Similarity	NPC145832
0.8721	High Similarity	NPC306555
0.8721	High Similarity	NPC12053
0.8721	High Similarity	NPC81218
0.8721	High Similarity	NPC205421
0.8721	High Similarity	NPC158376
0.8721	High Similarity	NPC474931
0.8706	High Similarity	NPC80759
0.8706	High Similarity	NPC60186
0.8706	High Similarity	NPC79402
0.8705	High Similarity	NPC82056
0.8701	High Similarity	NPC230276
0.8701	High Similarity	NPC195538
0.8701	High Similarity	NPC257269
0.869	High Similarity	NPC247639
0.869	High Similarity	NPC25084
0.8674	High Similarity	NPC473716
0.8674	High Similarity	NPC475597
0.8652	High Similarity	NPC476202
0.8647	High Similarity	NPC235143
0.8647	High Similarity	NPC119649
0.8647	High Similarity	NPC230956
0.8647	High Similarity	NPC205255
0.8647	High Similarity	NPC271388
0.8644	High Similarity	NPC40496
0.8644	High Similarity	NPC119068
0.8644	High Similarity	NPC474507
0.8631	High Similarity	NPC249797
0.8631	High Similarity	NPC469817
0.8631	High Similarity	NPC54379
0.8631	High Similarity	NPC110416
0.8631	High Similarity	NPC207757
0.8631	High Similarity	NPC278799
0.8631	High Similarity	NPC172765
0.8631	High Similarity	NPC204828
0.8631	High Similarity	NPC127674
0.8631	High Similarity	NPC5238
0.8631	High Similarity	NPC276588
0.8631	High Similarity	NPC2413
0.8631	High Similarity	NPC39701
0.8631	High Similarity	NPC193949
0.8631	High Similarity	NPC184026
0.8631	High Similarity	NPC295691
0.8631	High Similarity	NPC189266
0.8605	High Similarity	NPC13504
0.8605	High Similarity	NPC212794
0.8605	High Similarity	NPC306843
0.8605	High Similarity	NPC96603
0.8605	High Similarity	NPC78222
0.8605	High Similarity	NPC253043
0.8605	High Similarity	NPC477563
0.8605	High Similarity	NPC136508
0.8605	High Similarity	NPC196447
0.8601	High Similarity	NPC38964
0.8588	High Similarity	NPC221864
0.8547	High Similarity	NPC1229
0.8547	High Similarity	NPC324144
0.8539	High Similarity	NPC32154
0.8531	High Similarity	NPC476577
0.8531	High Similarity	NPC173416
0.8531	High Similarity	NPC148709
0.8466	Intermediate Similarity	NPC10871
0.8439	Intermediate Similarity	NPC475393
0.843	Intermediate Similarity	NPC27410
0.843	Intermediate Similarity	NPC166014
0.8427	Intermediate Similarity	NPC241704
0.8418	Intermediate Similarity	NPC477020
0.8418	Intermediate Similarity	NPC66341
0.8418	Intermediate Similarity	NPC192135
0.8412	Intermediate Similarity	NPC123323
0.8393	Intermediate Similarity	NPC220858
0.8393	Intermediate Similarity	NPC192768
0.8393	Intermediate Similarity	NPC88249
0.8393	Intermediate Similarity	NPC151895
0.8393	Intermediate Similarity	NPC97221
0.838	Intermediate Similarity	NPC320223
0.838	Intermediate Similarity	NPC114364
0.8343	Intermediate Similarity	NPC56887
0.8343	Intermediate Similarity	NPC223077
0.8343	Intermediate Similarity	NPC193853
0.8333	Intermediate Similarity	NPC477565
0.8333	Intermediate Similarity	NPC103379
0.8315	Intermediate Similarity	NPC82763
0.8314	Intermediate Similarity	NPC476572
0.8305	Intermediate Similarity	NPC109925
0.8305	Intermediate Similarity	NPC477562
0.8305	Intermediate Similarity	NPC69712
0.8305	Intermediate Similarity	NPC26240
0.8286	Intermediate Similarity	NPC276944
0.8286	Intermediate Similarity	NPC238530
0.8286	Intermediate Similarity	NPC209377
0.8286	Intermediate Similarity	NPC169743
0.8286	Intermediate Similarity	NPC232514
0.8274	Intermediate Similarity	NPC476571
0.8274	Intermediate Similarity	NPC246587
0.8274	Intermediate Similarity	NPC428
0.8274	Intermediate Similarity	NPC135538

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 NPC22115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	778
0.2-0.3	1151
0.3-0.4	2234
0.4-0.5	2362
0.5-0.6	1542
0.6-0.7	698
0.7-0.8	159
0.8-0.85	7
0.85-0.9	2
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9762	High Similarity	NPD8053	Approved
0.9762	High Similarity	NPD8054	Approved
0.9345	High Similarity	NPD8252	Approved
0.9345	High Similarity	NPD8099	Discontinued
0.9345	High Similarity	NPD8251	Approved
0.929	High Similarity	NPD8156	Discontinued
0.8644	High Similarity	NPD8453	Clinical (unspecified phase)
0.8396	Intermediate Similarity	NPD8095	Phase 1
0.8214	Intermediate Similarity	NPD4584	Approved
0.8207	Intermediate Similarity	NPD7906	Approved
0.8161	Intermediate Similarity	NPD6788	Approved
0.7989	Intermediate Similarity	NPD7313	Approved
0.7989	Intermediate Similarity	NPD7312	Approved
0.7989	Intermediate Similarity	NPD7311	Approved
0.7989	Intermediate Similarity	NPD7310	Approved
0.7946	Intermediate Similarity	NPD7309	Approved
0.7943	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4773	Phase 2
0.7931	Intermediate Similarity	NPD4772	Phase 2
0.791	Intermediate Similarity	NPD7833	Phase 2
0.791	Intermediate Similarity	NPD7831	Phase 2
0.791	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4578	Approved
0.7892	Intermediate Similarity	NPD4577	Approved
0.7861	Intermediate Similarity	NPD4663	Approved
0.7857	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD27	Approved
0.7845	Intermediate Similarity	NPD2489	Approved
0.7833	Intermediate Similarity	NPD6071	Discontinued
0.7833	Intermediate Similarity	NPD3051	Approved
0.779	Intermediate Similarity	NPD2970	Approved
0.779	Intermediate Similarity	NPD2969	Approved
0.7784	Intermediate Similarity	NPD7298	Approved
0.7733	Intermediate Similarity	NPD2421	Approved
0.7733	Intermediate Similarity	NPD2420	Approved
0.7714	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7447	Phase 1
0.765	Intermediate Similarity	NPD2898	Approved
0.7647	Intermediate Similarity	NPD7549	Discontinued
0.7624	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD2563	Approved
0.7598	Intermediate Similarity	NPD2560	Approved
0.7572	Intermediate Similarity	NPD3845	Phase 1
0.7556	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD4010	Discontinued
0.7529	Intermediate Similarity	NPD7212	Phase 2
0.7529	Intermediate Similarity	NPD7213	Phase 3
0.7514	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4055	Discovery
0.7486	Intermediate Similarity	NPD1424	Approved
0.7475	Intermediate Similarity	NPD2494	Approved
0.7475	Intermediate Similarity	NPD3452	Approved
0.7475	Intermediate Similarity	NPD3450	Approved
0.7475	Intermediate Similarity	NPD2493	Approved
0.7472	Intermediate Similarity	NPD4678	Approved
0.7472	Intermediate Similarity	NPD4675	Approved
0.7471	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5677	Discontinued
0.7401	Intermediate Similarity	NPD6031	Approved
0.7401	Intermediate Similarity	NPD6030	Approved
0.7381	Intermediate Similarity	NPD6997	Phase 2
0.7371	Intermediate Similarity	NPD2490	Approved
0.7371	Intermediate Similarity	NPD2488	Approved
0.7371	Intermediate Similarity	NPD7124	Phase 2
0.7366	Intermediate Similarity	NPD4481	Phase 3
0.7363	Intermediate Similarity	NPD4582	Approved
0.7363	Intermediate Similarity	NPD4583	Approved
0.7354	Intermediate Similarity	NPD8152	Approved
0.7354	Intermediate Similarity	NPD8153	Approved
0.7345	Intermediate Similarity	NPD6090	Discontinued
0.7343	Intermediate Similarity	NPD7047	Phase 3
0.7333	Intermediate Similarity	NPD6072	Discontinued
0.733	Intermediate Similarity	NPD7598	Phase 2
0.7318	Intermediate Similarity	NPD4017	Approved
0.7314	Intermediate Similarity	NPD5241	Discontinued
0.7313	Intermediate Similarity	NPD4002	Approved
0.7313	Intermediate Similarity	NPD4004	Approved
0.7303	Intermediate Similarity	NPD3640	Phase 3
0.7303	Intermediate Similarity	NPD3641	Approved
0.7303	Intermediate Similarity	NPD3639	Approved
0.7297	Intermediate Similarity	NPD6107	Approved
0.7297	Intermediate Similarity	NPD7802	Discontinued
0.7292	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4474	Approved
0.7278	Intermediate Similarity	NPD4475	Approved
0.7273	Intermediate Similarity	NPD2974	Approved
0.7273	Intermediate Similarity	NPD2973	Approved
0.7273	Intermediate Similarity	NPD2975	Approved
0.7253	Intermediate Similarity	NPD5772	Approved
0.7253	Intermediate Similarity	NPD5773	Approved
0.725	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6042	Phase 2
0.7249	Intermediate Similarity	NPD42	Phase 2
0.7228	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4005	Discontinued
0.7207	Intermediate Similarity	NPD2122	Discontinued
0.7202	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5177	Phase 3
0.7191	Intermediate Similarity	NPD4123	Phase 3
0.7178	Intermediate Similarity	NPD5006	Approved
0.7178	Intermediate Similarity	NPD5005	Approved
0.7175	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4580	Approved
0.7159	Intermediate Similarity	NPD6748	Discontinued
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1613	Approved
0.7127	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5718	Phase 2
0.7115	Intermediate Similarity	NPD7827	Phase 1
0.7114	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2200	Suspended
0.7101	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6667	Approved
0.7079	Intermediate Similarity	NPD6666	Approved
0.7068	Intermediate Similarity	NPD5313	Approved
0.7068	Intermediate Similarity	NPD5312	Approved
0.7068	Intermediate Similarity	NPD4873	Discontinued
0.7065	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2968	Approved
0.7062	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2971	Approved
0.7062	Intermediate Similarity	NPD7466	Approved
0.7045	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3124	Discontinued
0.7033	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6853	Approved
0.7026	Intermediate Similarity	NPD6851	Approved
0.7024	Intermediate Similarity	NPD4040	Phase 1
0.7022	Intermediate Similarity	NPD3692	Discontinued
0.7015	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7907	Approved
0.7	Intermediate Similarity	NPD4908	Phase 1
0.6995	Remote Similarity	NPD6297	Approved
0.6989	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4420	Approved
0.6973	Remote Similarity	NPD2977	Approved
0.6973	Remote Similarity	NPD2978	Approved
0.6968	Remote Similarity	NPD4666	Phase 3
0.6963	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5938	Phase 3
0.6959	Remote Similarity	NPD3027	Phase 3
0.6959	Remote Similarity	NPD4625	Phase 3
0.6949	Remote Similarity	NPD7037	Approved
0.6947	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7479	Phase 2
0.6936	Remote Similarity	NPD2238	Phase 2
0.6927	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2677	Approved
0.6927	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5976	Discontinued
0.6919	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5709	Phase 3
0.6914	Remote Similarity	NPD6895	Approved
0.6914	Remote Similarity	NPD6111	Discontinued
0.6914	Remote Similarity	NPD6896	Approved
0.691	Remote Similarity	NPD4236	Phase 3
0.691	Remote Similarity	NPD4237	Approved
0.691	Remote Similarity	NPD4162	Approved
0.691	Remote Similarity	NPD3060	Approved
0.6895	Remote Similarity	NPD4166	Phase 2
0.6889	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4585	Approved
0.6879	Remote Similarity	NPD2674	Phase 3
0.6878	Remote Similarity	NPD2904	Discontinued
0.6875	Remote Similarity	NPD1753	Discontinued
0.6868	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5090	Approved
0.6865	Remote Similarity	NPD5089	Approved
0.6865	Remote Similarity	NPD7438	Suspended
0.6862	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6723	Discontinued
0.6847	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7701	Phase 2
0.6839	Remote Similarity	NPD7177	Discontinued
0.6834	Remote Similarity	NPD6842	Approved
0.6834	Remote Similarity	NPD7291	Discontinued
0.6834	Remote Similarity	NPD6843	Phase 3
0.6834	Remote Similarity	NPD6841	Approved
0.6833	Remote Similarity	NPD5160	Discontinued
0.6831	Remote Similarity	NPD7427	Discontinued
0.683	Remote Similarity	NPD7048	Phase 3
0.6825	Remote Similarity	NPD5676	Approved
0.6823	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD6166	Phase 2
0.6823	Remote Similarity	NPD6167	Clinical (unspecified phase)

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