NPASS Compound

Structure

NPC280473 OpenBabel07101718282D 52 57 0 0 1 0 0 0 0 0999 V2000 -3.7766 5.6541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1126 -1.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5604 -1.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2286 2.5193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9311 5.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5020 -2.2461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4582 -0.8295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0125 5.0632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0700 1.9861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2334 1.5031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0700 2.9520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2185 -2.8709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3969 1.9861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2334 3.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6163 -2.1157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5604 0.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5604 1.5031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1737 -2.7269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1858 1.1498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9243 -1.0726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3776 0.7841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7239 -0.9117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3583 2.1002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1460 4.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1551 -1.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3969 2.9520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9692 -1.2165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7239 0.0542 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7239 1.9861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1422 4.1060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8096 1.8905 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5077 2.5580 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1126 0.5372 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8678 2.1054 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5604 3.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3669 -0.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8096 0.1499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8678 -0.0650 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1126 1.5031 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2287 1.0202 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5266 -1.8278 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 4.3611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0980 -1.7441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0360 3.7397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5604 4.4009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7198 0.4378 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 -0.4380 3.9888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7239 2.9520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3781 3.5152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4118 -0.6053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5756 0.3085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 22 2 0 0 0 0 3 22 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 8 30 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 26 2 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 17 2 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 41 2 0 0 0 0 19 23 1 0 0 0 0 19 40 1 0 0 0 0 20 27 2 0 0 0 0 20 41 1 0 0 0 0 21 47 1 0 0 0 0 23 4 1 6 0 0 0 23 32 1 0 0 0 0 24 42 2 0 0 0 0 24 48 1 0 0 0 0 25 43 2 0 0 0 0 25 52 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 22 1 6 0 0 0 28 33 1 0 0 0 0 29 39 1 6 0 0 0 29 49 1 0 0 0 0 30 44 2 0 0 0 0 30 50 1 0 0 0 0 31 32 1 0 0 0 0 31 34 1 0 0 0 0 31 40 1 6 0 0 0 32 50 1 6 0 0 0 33 38 1 1 0 0 0 33 39 1 0 0 0 0 34 39 1 1 0 0 0 34 48 1 0 0 0 0 35 45 2 0 0 0 0 35 49 1 0 0 0 0 36 46 2 0 0 0 0 36 51 1 0 0 0 0 37 38 1 6 0 0 0 37 40 1 0 0 0 0 37 51 1 0 0 0 0 38 7 1 6 0 0 0 38 47 1 0 0 0 0 39 21 1 1 0 0 0 40 52 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	715.3
Volume:	722.472
LogP:	4.259
LogD:	2.436
LogS:	-4.384
# Rotatable Bonds:	14
TPSA:	153.62
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	6.145
Fsp3:	0.5
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:	-5.288
MDCK Permeability:	5.73316247027833e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.081
20% Bioavailability (F20%):	0.792
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	79.18340301513672%
Volume Distribution (VD):	2.524
Pgp-substrate:	15.00966739654541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.214
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.351
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	4.008
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.811
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.35
Maximum Recommended Daily Dose:	0.116
Skin Sensitization:	0.099
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.442

Download Data

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

Natural Product: NPC280473

Natural Product ID:	NPC280473
*Common Name:**	VVOHQWVWQIGHHS-UXXSSWLWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VVOHQWVWQIGHHS-UXXSSWLWSA-N
Standard InCHI:	InChI=1S/C40H45NO11/c1-8-30(44)50-32-23(4)19-40(52-25(6)43)31(32)34(48-24(5)42)39-21-47-38(7,37(40)51-36(46)27-15-12-18-41-20-27)33(39)28(22(2)3)16-17-29(39)49-35(45)26-13-10-9-11-14-26/h9-18,20,23,28-29,31-34,37H,2,8,19,21H2,1,3-7H3/t23-,28+,29+,31+,32-,33-,34+,37-,38+,39+,40+/m0/s1
SMILES:	CCC(=O)O[C@H]1[C@@H](C)C[C@]2([C@H]1[C@H]([C@]13CO[C@](C)([C@@H]3[C@H](C=C[C@H]1OC(=O)c1ccccc1)C(=C)C)[C@@H]2OC(=O)c1cccnc1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2030590
PubChem CID:	70694185
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	Roots	Kunming, Yunnan Province, China	2010-JUL	PMID[21928782]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21928782]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22560584]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7775985]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	74300.0	nM	PMID[524159]

☑ 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 NPC280473 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	380
0.1-0.2	1527
0.2-0.3	4569
0.3-0.4	14431
0.4-0.5	16142
0.5-0.6	4339
0.6-0.7	1065
0.7-0.8	130
0.8-0.85	80
0.85-0.9	24
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC323551
0.9947	High Similarity	NPC41724
0.9947	High Similarity	NPC51008
0.9635	High Similarity	NPC165837
0.9536	High Similarity	NPC193361
0.9536	High Similarity	NPC62844
0.9381	High Similarity	NPC476467
0.9146	High Similarity	NPC187494
0.9133	High Similarity	NPC40919
0.9133	High Similarity	NPC470189
0.9078	High Similarity	NPC213143
0.9077	High Similarity	NPC470190
0.9064	High Similarity	NPC233727
0.905	High Similarity	NPC319556
0.895	High Similarity	NPC207531
0.89	High Similarity	NPC4421
0.8883	High Similarity	NPC285411
0.8883	High Similarity	NPC14116
0.8852	High Similarity	NPC238278
0.8841	High Similarity	NPC311196
0.8841	High Similarity	NPC134384
0.8806	High Similarity	NPC264674
0.8768	High Similarity	NPC158020
0.8768	High Similarity	NPC6576
0.8768	High Similarity	NPC62367
0.8768	High Similarity	NPC75600
0.8768	High Similarity	NPC212768
0.8768	High Similarity	NPC473089
0.8768	High Similarity	NPC473115
0.8732	High Similarity	NPC477903
0.8725	High Similarity	NPC84815
0.8725	High Similarity	NPC216428
0.8725	High Similarity	NPC301368
0.8719	High Similarity	NPC471016
0.8706	High Similarity	NPC472553
0.8689	High Similarity	NPC235364
0.8683	High Similarity	NPC477901
0.867	High Similarity	NPC470306
0.867	High Similarity	NPC42678
0.867	High Similarity	NPC477907
0.867	High Similarity	NPC477909
0.8641	High Similarity	NPC477912
0.8627	High Similarity	NPC471014
0.8627	High Similarity	NPC475408
0.8627	High Similarity	NPC6981
0.8606	High Similarity	NPC477899
0.8606	High Similarity	NPC26881
0.8606	High Similarity	NPC477902
0.8606	High Similarity	NPC477900
0.8599	High Similarity	NPC477788
0.8599	High Similarity	NPC127026
0.8599	High Similarity	NPC127720
0.8585	High Similarity	NPC144779
0.8585	High Similarity	NPC294579
0.8565	High Similarity	NPC148860
0.8558	High Similarity	NPC471980
0.8557	High Similarity	NPC48042
0.8557	High Similarity	NPC472550
0.8557	High Similarity	NPC304179
0.8544	High Similarity	NPC472555
0.8529	High Similarity	NPC319128
0.8524	High Similarity	NPC124029
0.8517	High Similarity	NPC328154
0.8488	Intermediate Similarity	NPC477910
0.8469	Intermediate Similarity	NPC76565
0.8469	Intermediate Similarity	NPC250807
0.8469	Intermediate Similarity	NPC57797
0.8465	Intermediate Similarity	NPC472752
0.8447	Intermediate Similarity	NPC206343
0.8447	Intermediate Similarity	NPC477908
0.8443	Intermediate Similarity	NPC91125
0.8439	Intermediate Similarity	NPC228331
0.8436	Intermediate Similarity	NPC87152
0.8436	Intermediate Similarity	NPC475600
0.8436	Intermediate Similarity	NPC477787
0.8436	Intermediate Similarity	NPC476110
0.8436	Intermediate Similarity	NPC328186
0.8436	Intermediate Similarity	NPC211920
0.8436	Intermediate Similarity	NPC228377
0.8436	Intermediate Similarity	NPC122968
0.8436	Intermediate Similarity	NPC475631
0.8429	Intermediate Similarity	NPC475137
0.8429	Intermediate Similarity	NPC475498
0.8429	Intermediate Similarity	NPC473850
0.8421	Intermediate Similarity	NPC477911
0.8416	Intermediate Similarity	NPC63041
0.8404	Intermediate Similarity	NPC477906
0.8396	Intermediate Similarity	NPC475644
0.8396	Intermediate Similarity	NPC470486
0.8396	Intermediate Similarity	NPC471977
0.8396	Intermediate Similarity	NPC471190
0.8349	Intermediate Similarity	NPC475601
0.8349	Intermediate Similarity	NPC146824
0.8318	Intermediate Similarity	NPC473689
0.8318	Intermediate Similarity	NPC96801
0.8318	Intermediate Similarity	NPC292416
0.8318	Intermediate Similarity	NPC475303
0.8318	Intermediate Similarity	NPC475596
0.8318	Intermediate Similarity	NPC150698
0.8318	Intermediate Similarity	NPC316841
0.831	Intermediate Similarity	NPC475362
0.8302	Intermediate Similarity	NPC473506
0.8279	Intermediate Similarity	NPC244839
0.8279	Intermediate Similarity	NPC319880
0.8279	Intermediate Similarity	NPC320324
0.8279	Intermediate Similarity	NPC30456
0.8267	Intermediate Similarity	NPC289086
0.825	Intermediate Similarity	NPC470279
0.8241	Intermediate Similarity	NPC237702
0.8203	Intermediate Similarity	NPC475406
0.8203	Intermediate Similarity	NPC327769
0.8194	Intermediate Similarity	NPC469748
0.8165	Intermediate Similarity	NPC327904
0.8165	Intermediate Similarity	NPC38959
0.8119	Intermediate Similarity	NPC475426
0.8119	Intermediate Similarity	NPC35208
0.8119	Intermediate Similarity	NPC170751
0.8054	Intermediate Similarity	NPC253482
0.799	Intermediate Similarity	NPC292517
0.7961	Intermediate Similarity	NPC309498
0.7946	Intermediate Similarity	NPC475648
0.7877	Intermediate Similarity	NPC30570
0.7876	Intermediate Similarity	NPC475533
0.7861	Intermediate Similarity	NPC103230
0.7841	Intermediate Similarity	NPC475315
0.7841	Intermediate Similarity	NPC324619
0.784	Intermediate Similarity	NPC162812
0.7837	Intermediate Similarity	NPC475835
0.7832	Intermediate Similarity	NPC148896
0.7832	Intermediate Similarity	NPC471013
0.7832	Intermediate Similarity	NPC180668
0.7753	Intermediate Similarity	NPC476090
0.7716	Intermediate Similarity	NPC53255
0.7716	Intermediate Similarity	NPC475301
0.7716	Intermediate Similarity	NPC326930
0.7716	Intermediate Similarity	NPC85879
0.7707	Intermediate Similarity	NPC320748
0.7707	Intermediate Similarity	NPC324245
0.7703	Intermediate Similarity	NPC471004
0.7696	Intermediate Similarity	NPC10904
0.7682	Intermediate Similarity	NPC13603
0.7681	Intermediate Similarity	NPC32451
0.7681	Intermediate Similarity	NPC328559
0.7672	Intermediate Similarity	NPC471015
0.7653	Intermediate Similarity	NPC111732
0.7633	Intermediate Similarity	NPC79223
0.7585	Intermediate Similarity	NPC473833
0.7573	Intermediate Similarity	NPC329024
0.7553	Intermediate Similarity	NPC107287
0.7521	Intermediate Similarity	NPC471978
0.7521	Intermediate Similarity	NPC328928
0.75	Intermediate Similarity	NPC123395
0.75	Intermediate Similarity	NPC156044
0.7488	Intermediate Similarity	NPC44354
0.7452	Intermediate Similarity	NPC59033
0.7452	Intermediate Similarity	NPC317672
0.7449	Intermediate Similarity	NPC249614
0.7427	Intermediate Similarity	NPC471979
0.7411	Intermediate Similarity	NPC191310
0.7406	Intermediate Similarity	NPC12944
0.7406	Intermediate Similarity	NPC25442
0.74	Intermediate Similarity	NPC317010
0.7391	Intermediate Similarity	NPC135950
0.7379	Intermediate Similarity	NPC471546
0.734	Intermediate Similarity	NPC112741
0.734	Intermediate Similarity	NPC282103
0.7333	Intermediate Similarity	NPC103361
0.7318	Intermediate Similarity	NPC141385
0.7316	Intermediate Similarity	NPC37473
0.7264	Intermediate Similarity	NPC155792
0.7222	Intermediate Similarity	NPC470280
0.7206	Intermediate Similarity	NPC207851
0.719	Intermediate Similarity	NPC109922
0.7169	Intermediate Similarity	NPC318299
0.7163	Intermediate Similarity	NPC138370
0.7156	Intermediate Similarity	NPC314834
0.7136	Intermediate Similarity	NPC317752
0.7101	Intermediate Similarity	NPC325775
0.7101	Intermediate Similarity	NPC328798
0.7094	Intermediate Similarity	NPC164340
0.7089	Intermediate Similarity	NPC50997
0.7089	Intermediate Similarity	NPC160127
0.7079	Intermediate Similarity	NPC84347
0.7073	Intermediate Similarity	NPC327373
0.7067	Intermediate Similarity	NPC253314
0.7059	Intermediate Similarity	NPC229348
0.7059	Intermediate Similarity	NPC471997
0.7048	Intermediate Similarity	NPC55493
0.7033	Intermediate Similarity	NPC469489
0.7018	Intermediate Similarity	NPC314297
0.7018	Intermediate Similarity	NPC315545
0.7	Intermediate Similarity	NPC230085
0.7	Intermediate Similarity	NPC123839
0.7	Intermediate Similarity	NPC159630
0.6981	Remote Similarity	NPC476205
0.6981	Remote Similarity	NPC476257
0.6981	Remote Similarity	NPC476256
0.6981	Remote Similarity	NPC476207
0.6981	Remote Similarity	NPC476206
0.6981	Remote Similarity	NPC259791

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 NPC280473 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	575
0.2-0.3	690
0.3-0.4	1929
0.4-0.5	3443
0.5-0.6	1924
0.6-0.7	343
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8457	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7396	Approved
0.7713	Intermediate Similarity	NPD820	Phase 3
0.7565	Intermediate Similarity	NPD8468	Phase 2
0.7465	Intermediate Similarity	NPD2510	Approved
0.7465	Intermediate Similarity	NPD2509	Approved
0.7391	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD9271	Approved
0.7324	Intermediate Similarity	NPD3947	Discontinued
0.7306	Intermediate Similarity	NPD3389	Approved
0.7306	Intermediate Similarity	NPD3393	Approved
0.7306	Intermediate Similarity	NPD3394	Approved
0.7294	Intermediate Similarity	NPD3795	Approved
0.7294	Intermediate Similarity	NPD3794	Approved
0.7282	Intermediate Similarity	NPD6635	Approved
0.7281	Intermediate Similarity	NPD4417	Approved
0.7277	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD4506	Discontinued
0.7209	Intermediate Similarity	NPD7010	Phase 3
0.7204	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6529	Discontinued
0.7163	Intermediate Similarity	NPD2831	Approved
0.713	Intermediate Similarity	NPD6770	Approved
0.71	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4301	Approved
0.7045	Intermediate Similarity	NPD5475	Discontinued
0.704	Intermediate Similarity	NPD8326	Phase 3
0.704	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8325	Phase 3
0.7022	Intermediate Similarity	NPD3280	Approved
0.7021	Intermediate Similarity	NPD107	Approved
0.702	Intermediate Similarity	NPD5088	Discontinued
0.6996	Remote Similarity	NPD5891	Approved
0.6979	Remote Similarity	NPD7886	Phase 2
0.6979	Remote Similarity	NPD7885	Phase 2
0.6947	Remote Similarity	NPD8479	Phase 2
0.6937	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9074	Approved
0.6875	Remote Similarity	NPD9075	Approved
0.6851	Remote Similarity	NPD3006	Discontinued
0.684	Remote Similarity	NPD2336	Approved
0.6825	Remote Similarity	NPD7234	Approved
0.6825	Remote Similarity	NPD7233	Approved
0.6818	Remote Similarity	NPD2581	Approved
0.6818	Remote Similarity	NPD2582	Approved
0.6808	Remote Similarity	NPD4376	Phase 3
0.6806	Remote Similarity	NPD7778	Approved
0.6806	Remote Similarity	NPD7777	Approved
0.6806	Remote Similarity	NPD53	Approved
0.6804	Remote Similarity	NPD6176	Phase 1
0.6804	Remote Similarity	NPD1270	Approved
0.6796	Remote Similarity	NPD6641	Approved
0.6796	Remote Similarity	NPD6642	Approved
0.6792	Remote Similarity	NPD8063	Discontinued
0.6791	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD3371	Approved
0.6786	Remote Similarity	NPD7069	Discontinued
0.6784	Remote Similarity	NPD7878	Phase 2
0.6777	Remote Similarity	NPD4948	Discontinued
0.6777	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD6987	Phase 1
0.6762	Remote Similarity	NPD4889	Approved
0.6752	Remote Similarity	NPD7688	Phase 1
0.675	Remote Similarity	NPD2511	Approved
0.6744	Remote Similarity	NPD4427	Phase 2
0.6741	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7470	Discontinued
0.6726	Remote Similarity	NPD7707	Approved
0.6725	Remote Similarity	NPD1996	Discontinued
0.6713	Remote Similarity	NPD2307	Discontinued
0.6709	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1483	Discontinued
0.67	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6026	Approved
0.6681	Remote Similarity	NPD7404	Approved
0.668	Remote Similarity	NPD5482	Discontinued
0.6667	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4989	Phase 2
0.6667	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5513	Phase 2
0.6649	Remote Similarity	NPD2896	Discontinued
0.6638	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4499	Approved
0.6636	Remote Similarity	NPD6226	Phase 3
0.6623	Remote Similarity	NPD8160	Phase 2
0.6622	Remote Similarity	NPD5901	Discontinued
0.6622	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4529	Approved
0.662	Remote Similarity	NPD8020	Approved
0.662	Remote Similarity	NPD4528	Approved
0.662	Remote Similarity	NPD8021	Approved
0.662	Remote Similarity	NPD4526	Approved
0.6607	Remote Similarity	NPD7467	Discontinued
0.6598	Remote Similarity	NPD6790	Phase 1
0.6591	Remote Similarity	NPD4501	Approved
0.6591	Remote Similarity	NPD4500	Approved
0.6591	Remote Similarity	NPD6479	Discontinued
0.6584	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8289	Discontinued
0.6581	Remote Similarity	NPD5640	Discontinued
0.6574	Remote Similarity	NPD6665	Discontinued
0.6562	Remote Similarity	NPD7562	Approved
0.6561	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6298	Discontinued
0.6545	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6361	Phase 2
0.6542	Remote Similarity	NPD6791	Phase 2
0.6542	Remote Similarity	NPD8409	Suspended
0.654	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.654	Remote Similarity	NPD3178	Discontinued
0.6537	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1630	Approved
0.6535	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7708	Approved
0.6533	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.653	Remote Similarity	NPD5003	Discontinued
0.6526	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6995	Phase 1
0.6524	Remote Similarity	NPD8356	Approved
0.6522	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7001	Phase 3
0.6516	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD5022	Discontinued
0.6498	Remote Similarity	NPD4952	Phase 3
0.6496	Remote Similarity	NPD7803	Approved
0.6494	Remote Similarity	NPD4429	Discontinued
0.6491	Remote Similarity	NPD5866	Approved
0.6478	Remote Similarity	NPD5490	Discontinued
0.6476	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD1032	Phase 2
0.6473	Remote Similarity	NPD1573	Approved
0.6473	Remote Similarity	NPD1575	Approved
0.6471	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6999	Discontinued
0.6463	Remote Similarity	NPD6276	Discontinued
0.6463	Remote Similarity	NPD5888	Phase 2
0.6462	Remote Similarity	NPD3386	Phase 2
0.646	Remote Similarity	NPD8423	Phase 2
0.646	Remote Similarity	NPD8399	Phase 1
0.6449	Remote Similarity	NPD6241	Phase 1
0.6449	Remote Similarity	NPD7967	Discontinued
0.6443	Remote Similarity	NPD4804	Approved
0.6441	Remote Similarity	NPD6219	Discontinued
0.6439	Remote Similarity	NPD1631	Approved
0.6438	Remote Similarity	NPD6242	Discontinued
0.6437	Remote Similarity	NPD4369	Phase 2
0.6435	Remote Similarity	NPD5293	Phase 2
0.6435	Remote Similarity	NPD4334	Discontinued
0.6431	Remote Similarity	NPD5450	Discontinued
0.6429	Remote Similarity	NPD3238	Discontinued
0.6429	Remote Similarity	NPD7955	Approved
0.6429	Remote Similarity	NPD7956	Approved
0.6425	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD3922	Approved
0.6422	Remote Similarity	NPD3921	Approved
0.6422	Remote Similarity	NPD3923	Approved
0.6422	Remote Similarity	NPD3924	Approved
0.6418	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4373	Phase 2
0.6414	Remote Similarity	NPD8430	Approved
0.6411	Remote Similarity	NPD2077	Approved
0.6411	Remote Similarity	NPD2076	Approved
0.641	Remote Similarity	NPD4923	Phase 1
0.6409	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5072	Discontinued
0.6404	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6962	Phase 2
0.64	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2753	Discontinued
0.6398	Remote Similarity	NPD3925	Approved
0.6396	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD3813	Approved
0.6393	Remote Similarity	NPD7417	Discontinued
0.6393	Remote Similarity	NPD1173	Approved
0.6393	Remote Similarity	NPD7576	Discontinued
0.6385	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6825	Phase 1
0.6378	Remote Similarity	NPD4805	Approved
0.6377	Remote Similarity	NPD6446	Discontinued
0.6376	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7944	Discontinued
0.6355	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD5632	Approved
0.6352	Remote Similarity	NPD3354	Phase 2
0.6352	Remote Similarity	NPD1926	Approved
0.6352	Remote Similarity	NPD6578	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