NPASS Compound

Structure

NPC63304 OpenBabel07101719402D 44 48 0 0 1 0 0 0 0 0999 V2000 -2.9250 -0.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4800 -0.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5792 -2.5286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5611 -1.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8566 -2.7096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3882 -1.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3701 -0.5395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9431 -2.3029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0159 4.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8819 0.7556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1160 -1.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6656 -2.1218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2837 -0.9463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0159 -0.7444 0.0000 C 0 0 2 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 2.8819 -0.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 3.7556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1341 -2.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 -0.2444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2839 4.2556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5822 3.7556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5822 2.7556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7480 -0.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 0.7556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2839 2.2556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8819 3.7556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0927 -0.3585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2386 -3.8852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2839 5.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4482 4.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4482 2.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7480 -1.7444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6140 -0.2444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0159 1.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2205 -2.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 2.7556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2839 1.2556 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 2 39 1 0 0 0 0 3 6 1 0 0 0 0 3 15 2 0 0 0 0 4 7 2 0 0 0 0 4 15 1 0 0 0 0 5 8 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 21 1 0 0 0 0 9 10 2 0 0 0 0 11 18 2 0 0 0 0 11 30 1 0 0 0 0 12 31 1 0 0 0 0 13 19 2 0 0 0 0 13 40 1 0 0 0 0 14 1 1 1 0 0 0 14 18 1 0 0 0 0 14 41 1 0 0 0 0 16 32 1 0 0 0 0 17 9 1 1 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 27 1 0 0 0 0 19 26 1 0 0 0 0 20 12 1 1 0 0 0 20 23 1 0 0 0 0 20 42 1 0 0 0 0 21 33 2 0 0 0 0 21 41 1 0 0 0 0 22 28 1 0 0 0 0 22 30 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 6 0 0 0 24 25 1 0 0 0 0 24 35 1 1 0 0 0 25 29 1 0 0 0 0 25 36 1 6 0 0 0 26 37 2 0 0 0 0 26 39 1 0 0 0 0 27 38 2 0 0 0 0 27 44 1 0 0 0 0 28 40 1 0 0 0 0 28 43 1 6 0 0 0 29 42 1 0 0 0 0 29 43 1 1 0 0 0 30 10 1 6 0 0 0 30 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.18
Volume:	581.352
LogP:	1.442
LogD:	1.142
LogS:	-2.622
# Rotatable Bonds:	10
TPSA:	207.74
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	5.714
Fsp3:	0.433
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:	-5.912
MDCK Permeability:	6.44513129373081e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.103
Human Intestinal Absorption (HIA):	0.756
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	62.42707061767578%
Volume Distribution (VD):	0.72
Pgp-substrate:	21.423620223999023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.128
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.378
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	1.588
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.4
AMES Toxicity:	0.625
Rat Oral Acute Toxicity:	0.802
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.855
Carcinogencity:	0.925
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC63304

Natural Product ID:	NPC63304
*Common Name:**	13-O-T-Coumaroylplumieride
IUPAC Name:	methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Synonyms:
Standard InCHIKey:	WBCMGDNFDRNGGZ-DEYYTONKSA-N
Standard InCHI:	InChI=1S/C30H32O14/c1-14(41-21(33)8-5-15-3-6-16(32)7-4-15)18-11-30(44-27(18)38)10-9-17-19(26(37)39-2)13-40-28(22(17)30)43-29-25(36)24(35)23(34)20(12-31)42-29/h3-11,13-14,17,20,22-25,28-29,31-32,34-36H,12H2,1-2H3/b8-5+/t14-,17+,20+,22+,23+,24-,25+,28-,29-,30+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@]2(C=C3)OC(=O)C(=C2)[C@@H](OC(=O)/C=C/c2ccc(cc2)O)C)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499977
PubChem CID:	44593497
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	bark	Indonesia	n.a.	PMID[1965200]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12734	Plumeria rubra	Species	Apocynaceae	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
ED50	7
IC50	1
MIC	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[536508]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[536508]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	ug ml-1	PMID[536508]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[536509]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	50.0	ug ml-1	PMID[536508]
NPT1019	Organism	Trichomonas vaginalis	Trichomonas vaginalis	MIC	=	12500.0	nM	PMID[536510]

☑ 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 NPC63304 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	295
0.1-0.2	1112
0.2-0.3	2802
0.3-0.4	6175
0.4-0.5	10287
0.5-0.6	8030
0.6-0.7	11094
0.7-0.8	2715
0.8-0.85	138
0.85-0.9	30
0.9-0.95	13
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9712	High Similarity	NPC475539
0.9712	High Similarity	NPC119773
0.9712	High Similarity	NPC143246
0.9712	High Similarity	NPC474268
0.964	High Similarity	NPC475528
0.9375	High Similarity	NPC474620
0.9209	High Similarity	NPC31745
0.9209	High Similarity	NPC220936
0.9203	High Similarity	NPC472132
0.9085	High Similarity	NPC293154
0.9067	High Similarity	NPC469384
0.9021	High Similarity	NPC202391
0.9021	High Similarity	NPC296659
0.9	High Similarity	NPC286919
0.9	High Similarity	NPC475663
0.8958	High Similarity	NPC210330
0.8951	High Similarity	NPC152796
0.8951	High Similarity	NPC475213
0.8933	High Similarity	NPC475378
0.8921	High Similarity	NPC169398
0.8912	High Similarity	NPC240592
0.8912	High Similarity	NPC117346
0.8897	High Similarity	NPC212808
0.8889	High Similarity	NPC77922
0.8889	High Similarity	NPC473281
0.8844	High Similarity	NPC96599
0.8841	High Similarity	NPC254819
0.8841	High Similarity	NPC281798
0.8784	High Similarity	NPC69367
0.8759	High Similarity	NPC184464
0.8759	High Similarity	NPC251062
0.8732	High Similarity	NPC65262
0.8732	High Similarity	NPC101686
0.8732	High Similarity	NPC469364
0.8725	High Similarity	NPC158546
0.8725	High Similarity	NPC289021
0.8716	High Similarity	NPC478234
0.8716	High Similarity	NPC478236
0.8707	High Similarity	NPC473149
0.869	High Similarity	NPC186296
0.8686	High Similarity	NPC106677
0.8667	High Similarity	NPC203664
0.8654	High Similarity	NPC180586
0.8639	High Similarity	NPC473147
0.8621	High Similarity	NPC296643
0.8562	High Similarity	NPC478250
0.8561	High Similarity	NPC469549
0.8552	High Similarity	NPC154262
0.8552	High Similarity	NPC159387
0.8552	High Similarity	NPC7518
0.8552	High Similarity	NPC137501
0.8551	High Similarity	NPC45224
0.8551	High Similarity	NPC471881
0.8551	High Similarity	NPC156692
0.8551	High Similarity	NPC35288
0.8551	High Similarity	NPC173150
0.8551	High Similarity	NPC471882
0.8543	High Similarity	NPC194705
0.8542	High Similarity	NPC220942
0.8542	High Similarity	NPC49597
0.8523	High Similarity	NPC189631
0.8497	Intermediate Similarity	NPC475484
0.8489	Intermediate Similarity	NPC225307
0.8478	Intermediate Similarity	NPC252114
0.8478	Intermediate Similarity	NPC471157
0.8477	Intermediate Similarity	NPC475379
0.8456	Intermediate Similarity	NPC52097
0.8452	Intermediate Similarity	NPC76211
0.8451	Intermediate Similarity	NPC114116
0.844	Intermediate Similarity	NPC478255
0.8429	Intermediate Similarity	NPC253595
0.8425	Intermediate Similarity	NPC46644
0.8411	Intermediate Similarity	NPC35097
0.8406	Intermediate Similarity	NPC126991
0.8406	Intermediate Similarity	NPC83218
0.8403	Intermediate Similarity	NPC470572
0.8382	Intermediate Similarity	NPC11724
0.8378	Intermediate Similarity	NPC194938
0.8345	Intermediate Similarity	NPC61181
0.8333	Intermediate Similarity	NPC179914
0.8322	Intermediate Similarity	NPC254398
0.8312	Intermediate Similarity	NPC478232
0.8311	Intermediate Similarity	NPC237872
0.8311	Intermediate Similarity	NPC116104
0.8311	Intermediate Similarity	NPC302286
0.8311	Intermediate Similarity	NPC88754
0.8311	Intermediate Similarity	NPC263397
0.831	Intermediate Similarity	NPC235294
0.831	Intermediate Similarity	NPC246869
0.831	Intermediate Similarity	NPC225384
0.831	Intermediate Similarity	NPC138777
0.831	Intermediate Similarity	NPC46137
0.8309	Intermediate Similarity	NPC476872
0.8301	Intermediate Similarity	NPC478235
0.8289	Intermediate Similarity	NPC12006
0.8286	Intermediate Similarity	NPC288416
0.8286	Intermediate Similarity	NPC103533
0.8278	Intermediate Similarity	NPC473428
0.8278	Intermediate Similarity	NPC120728
0.8278	Intermediate Similarity	NPC23677
0.8276	Intermediate Similarity	NPC471345
0.8269	Intermediate Similarity	NPC187205
0.8267	Intermediate Similarity	NPC473867
0.8267	Intermediate Similarity	NPC291153
0.8264	Intermediate Similarity	NPC471029
0.8264	Intermediate Similarity	NPC471883
0.8252	Intermediate Similarity	NPC473924
0.8252	Intermediate Similarity	NPC473285
0.8247	Intermediate Similarity	NPC229354
0.8243	Intermediate Similarity	NPC148080
0.8243	Intermediate Similarity	NPC469623
0.8239	Intermediate Similarity	NPC109990
0.8239	Intermediate Similarity	NPC17567
0.8228	Intermediate Similarity	NPC477627
0.8224	Intermediate Similarity	NPC478242
0.8212	Intermediate Similarity	NPC470330
0.8207	Intermediate Similarity	NPC476870
0.8194	Intermediate Similarity	NPC28637
0.8194	Intermediate Similarity	NPC164172
0.8194	Intermediate Similarity	NPC472127
0.8194	Intermediate Similarity	NPC472128
0.8188	Intermediate Similarity	NPC469367
0.8187	Intermediate Similarity	NPC294722
0.8182	Intermediate Similarity	NPC219677
0.8182	Intermediate Similarity	NPC106818
0.8176	Intermediate Similarity	NPC476011
0.8176	Intermediate Similarity	NPC145847
0.8176	Intermediate Similarity	NPC80098
0.817	Intermediate Similarity	NPC182350
0.8169	Intermediate Similarity	NPC477293
0.8169	Intermediate Similarity	NPC295970
0.8169	Intermediate Similarity	NPC477294
0.8169	Intermediate Similarity	NPC229784
0.8165	Intermediate Similarity	NPC474936
0.8165	Intermediate Similarity	NPC138993
0.8163	Intermediate Similarity	NPC321638
0.8163	Intermediate Similarity	NPC171134
0.8163	Intermediate Similarity	NPC321184
0.8163	Intermediate Similarity	NPC328273
0.8153	Intermediate Similarity	NPC104275
0.8153	Intermediate Similarity	NPC226759
0.8153	Intermediate Similarity	NPC4747
0.8146	Intermediate Similarity	NPC37838
0.8146	Intermediate Similarity	NPC320734
0.8141	Intermediate Similarity	NPC156624
0.8141	Intermediate Similarity	NPC172920
0.8137	Intermediate Similarity	NPC469419
0.8133	Intermediate Similarity	NPC478240
0.8133	Intermediate Similarity	NPC110063
0.8129	Intermediate Similarity	NPC257847
0.8129	Intermediate Similarity	NPC87403
0.8125	Intermediate Similarity	NPC471066
0.8125	Intermediate Similarity	NPC471095
0.8117	Intermediate Similarity	NPC478249
0.8117	Intermediate Similarity	NPC269914
0.8113	Intermediate Similarity	NPC293568
0.8113	Intermediate Similarity	NPC117943
0.8112	Intermediate Similarity	NPC469705
0.8112	Intermediate Similarity	NPC17968
0.8112	Intermediate Similarity	NPC470122
0.8105	Intermediate Similarity	NPC161955
0.8099	Intermediate Similarity	NPC232880
0.8095	Intermediate Similarity	NPC469696
0.8095	Intermediate Similarity	NPC476376
0.8092	Intermediate Similarity	NPC18789
0.8082	Intermediate Similarity	NPC182217
0.8082	Intermediate Similarity	NPC233350
0.8082	Intermediate Similarity	NPC70680
0.8082	Intermediate Similarity	NPC263829
0.8075	Intermediate Similarity	NPC475979
0.8069	Intermediate Similarity	NPC215484
0.8069	Intermediate Similarity	NPC322503
0.8069	Intermediate Similarity	NPC470143
0.8067	Intermediate Similarity	NPC204644
0.8067	Intermediate Similarity	NPC40305
0.8054	Intermediate Similarity	NPC79908
0.8052	Intermediate Similarity	NPC87630
0.8052	Intermediate Similarity	NPC116292
0.8052	Intermediate Similarity	NPC179128
0.8052	Intermediate Similarity	NPC267469
0.8052	Intermediate Similarity	NPC147224
0.805	Intermediate Similarity	NPC208676
0.805	Intermediate Similarity	NPC130489
0.8041	Intermediate Similarity	NPC81515
0.8041	Intermediate Similarity	NPC68092
0.8041	Intermediate Similarity	NPC197316
0.8041	Intermediate Similarity	NPC62800
0.8041	Intermediate Similarity	NPC226005
0.8041	Intermediate Similarity	NPC89105
0.8041	Intermediate Similarity	NPC64141
0.8041	Intermediate Similarity	NPC476383
0.8041	Intermediate Similarity	NPC324262
0.8041	Intermediate Similarity	NPC472350
0.8039	Intermediate Similarity	NPC308178
0.8039	Intermediate Similarity	NPC473138
0.8039	Intermediate Similarity	NPC28776
0.8037	Intermediate Similarity	NPC21956
0.8028	Intermediate Similarity	NPC476873
0.8027	Intermediate Similarity	NPC157554
0.8027	Intermediate Similarity	NPC255428

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 NPC63304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	716
0.2-0.3	1644
0.3-0.4	2849
0.4-0.5	2126
0.5-0.6	1174
0.6-0.7	368
0.7-0.8	28
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
0.8041	Intermediate Similarity	NPD7266	Discontinued
0.7892	Intermediate Similarity	NPD7685	Pre-registration
0.7812	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6190	Approved
0.7635	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7472	Approved
0.744	Intermediate Similarity	NPD3818	Discontinued
0.7438	Intermediate Similarity	NPD4380	Phase 2
0.7421	Intermediate Similarity	NPD1653	Approved
0.7419	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD7075	Discontinued
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7353	Intermediate Similarity	NPD7074	Phase 3
0.7337	Intermediate Similarity	NPD7228	Approved
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD9545	Approved
0.732	Intermediate Similarity	NPD7033	Discontinued
0.731	Intermediate Similarity	NPD6797	Phase 2
0.7301	Intermediate Similarity	NPD8455	Phase 2
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.7233	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6234	Discontinued
0.7212	Intermediate Similarity	NPD4966	Approved
0.7212	Intermediate Similarity	NPD4967	Phase 2
0.7212	Intermediate Similarity	NPD4965	Approved
0.7195	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8313	Approved
0.7184	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7134	Intermediate Similarity	NPD6801	Discontinued
0.7134	Intermediate Similarity	NPD37	Approved
0.7124	Intermediate Similarity	NPD230	Phase 1
0.7123	Intermediate Similarity	NPD1091	Approved
0.7089	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7458	Discontinued
0.7039	Intermediate Similarity	NPD3764	Approved
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5647	Approved
0.6988	Remote Similarity	NPD7819	Suspended
0.6971	Remote Similarity	NPD7240	Approved
0.6968	Remote Similarity	NPD6653	Approved
0.6959	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6799	Approved
0.695	Remote Similarity	NPD969	Suspended
0.6946	Remote Similarity	NPD3817	Phase 2
0.6946	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7799	Discontinued
0.6936	Remote Similarity	NPD3751	Discontinued
0.6933	Remote Similarity	NPD5403	Approved
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1934	Approved
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7435	Discontinued
0.6891	Remote Similarity	NPD7930	Approved
0.6886	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6233	Phase 2
0.6879	Remote Similarity	NPD1510	Phase 2
0.6875	Remote Similarity	NPD8166	Discontinued
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8434	Phase 2
0.6872	Remote Similarity	NPD8150	Discontinued
0.6867	Remote Similarity	NPD7411	Suspended
0.6862	Remote Similarity	NPD8319	Approved
0.6862	Remote Similarity	NPD8320	Phase 1
0.6855	Remote Similarity	NPD1549	Phase 2
0.6845	Remote Similarity	NPD5402	Approved
0.6821	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6166	Phase 2
0.6821	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1652	Phase 2
0.6813	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5401	Approved
0.681	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6599	Discontinued
0.6802	Remote Similarity	NPD3787	Discontinued
0.6796	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5124	Phase 1
0.6792	Remote Similarity	NPD6004	Phase 3
0.6792	Remote Similarity	NPD6005	Phase 3
0.6792	Remote Similarity	NPD6002	Phase 3
0.6792	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2801	Approved
0.6786	Remote Similarity	NPD1358	Approved
0.6782	Remote Similarity	NPD7473	Discontinued
0.6776	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6663	Approved
0.675	Remote Similarity	NPD2424	Discontinued
0.6744	Remote Similarity	NPD8127	Discontinued
0.6739	Remote Similarity	NPD6535	Approved
0.6739	Remote Similarity	NPD6534	Approved
0.6738	Remote Similarity	NPD6776	Approved
0.6738	Remote Similarity	NPD6777	Approved
0.6738	Remote Similarity	NPD6778	Approved
0.6738	Remote Similarity	NPD6782	Approved
0.6738	Remote Similarity	NPD6779	Approved
0.6738	Remote Similarity	NPD6780	Approved
0.6738	Remote Similarity	NPD6781	Approved
0.6737	Remote Similarity	NPD7999	Approved
0.6732	Remote Similarity	NPD5736	Approved
0.673	Remote Similarity	NPD2935	Discontinued
0.673	Remote Similarity	NPD2796	Approved
0.6724	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7700	Phase 2
0.672	Remote Similarity	NPD7699	Phase 2
0.6714	Remote Similarity	NPD3134	Approved
0.6712	Remote Similarity	NPD9493	Approved
0.6711	Remote Similarity	NPD2797	Approved
0.671	Remote Similarity	NPD3268	Approved
0.671	Remote Similarity	NPD6798	Discontinued
0.6707	Remote Similarity	NPD2534	Approved
0.6707	Remote Similarity	NPD2532	Approved
0.6707	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2533	Approved
0.6706	Remote Similarity	NPD3882	Suspended
0.6706	Remote Similarity	NPD7768	Phase 2
0.6705	Remote Similarity	NPD6232	Discontinued
0.6705	Remote Similarity	NPD5844	Phase 1
0.6702	Remote Similarity	NPD7584	Approved
0.6689	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1933	Approved
0.6687	Remote Similarity	NPD5058	Phase 3
0.6684	Remote Similarity	NPD7874	Approved
0.6684	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD7585	Approved
0.6649	Remote Similarity	NPD7783	Phase 2
0.6649	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1511	Approved
0.6645	Remote Similarity	NPD3225	Approved
0.6645	Remote Similarity	NPD7095	Approved
0.6644	Remote Similarity	NPD5125	Phase 3
0.6644	Remote Similarity	NPD5126	Approved
0.6643	Remote Similarity	NPD5048	Discontinued
0.6632	Remote Similarity	NPD8151	Discontinued
0.6632	Remote Similarity	NPD7697	Approved
0.6632	Remote Similarity	NPD7698	Approved
0.6632	Remote Similarity	NPD7696	Phase 3
0.6629	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1551	Phase 2
0.6624	Remote Similarity	NPD1240	Approved
0.6623	Remote Similarity	NPD9494	Approved
0.6623	Remote Similarity	NPD1608	Approved
0.6619	Remote Similarity	NPD6647	Phase 2
0.6615	Remote Similarity	NPD7583	Approved
0.6605	Remote Similarity	NPD6674	Discontinued
0.6601	Remote Similarity	NPD6362	Approved
0.6597	Remote Similarity	NPD7870	Phase 2
0.6597	Remote Similarity	NPD7871	Phase 2
0.6596	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5494	Approved
0.6582	Remote Similarity	NPD4340	Discontinued
0.6581	Remote Similarity	NPD6832	Phase 2
0.658	Remote Similarity	NPD7701	Phase 2
0.6579	Remote Similarity	NPD6823	Phase 2
0.6577	Remote Similarity	NPD1357	Approved
0.6575	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1512	Approved
0.6564	Remote Similarity	NPD7801	Approved
0.6562	Remote Similarity	NPD2799	Discontinued
0.6561	Remote Similarity	NPD4062	Phase 3
0.6556	Remote Similarity	NPD422	Phase 1
0.6556	Remote Similarity	NPD3705	Approved
0.655	Remote Similarity	NPD5353	Approved
0.6545	Remote Similarity	NPD7680	Approved
0.6541	Remote Similarity	NPD1607	Approved
0.6541	Remote Similarity	NPD7296	Approved
0.6538	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3027	Phase 3
0.6531	Remote Similarity	NPD7157	Approved
0.6522	Remote Similarity	NPD6099	Approved
0.6522	Remote Similarity	NPD6100	Approved
0.6519	Remote Similarity	NPD4060	Phase 1
0.6517	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD2861	Phase 2
0.6513	Remote Similarity	NPD9269	Phase 2
0.6513	Remote Similarity	NPD9717	Approved
0.6509	Remote Similarity	NPD7028	Phase 2
0.6505	Remote Similarity	NPD6213	Phase 3
0.6505	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6212	Phase 3
0.65	Remote Similarity	NPD8368	Discontinued
0.6494	Remote Similarity	NPD1203	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