NPASS Compound

Structure

CID82467 OpenBabel06191715422D 56 60 0 0 1 0 0 0 0 0999 V2000 -5.9723 0.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4999 3.1733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4999 -2.2209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9803 3.2562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1785 4.0440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7854 3.6663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0697 -1.1933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6734 -0.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9199 0.2465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8109 4.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3532 1.2649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8910 5.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0574 3.9779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6797 1.9384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1067 0.3450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2175 4.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3840 3.3045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7598 1.6919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1867 0.0985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4601 -0.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0199 0.4762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2534 2.2534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2534 -1.3010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6860 2.3505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5051 3.3705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1119 4.3397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9241 -0.2521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4640 3.5510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5133 0.7719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5543 0.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4601 1.2467 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0781 1.7772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3010 2.2534 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3010 -1.3010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4762 1.7772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0781 -0.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4762 -0.8248 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7906 2.8775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5934 0.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5543 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3232 1.6427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6652 3.8635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3584 5.2596 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0363 0.0925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7516 -1.4982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0371 1.9576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3469 -0.3945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7544 2.1525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7516 2.4506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8080 4.0932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4762 -1.7772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8707 3.1240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9199 1.1989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6665 0.3446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 2 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 41 1 0 0 0 0 9 41 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 28 2 0 0 0 0 17 28 1 0 0 0 0 18 29 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 42 1 0 0 0 0 21 1 1 6 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 22 33 1 0 0 0 0 23 3 1 1 0 0 0 23 34 1 0 0 0 0 23 36 1 0 0 0 0 24 43 2 0 0 0 0 24 50 1 0 0 0 0 25 44 2 0 0 0 0 25 51 1 0 0 0 0 26 45 2 0 0 0 0 26 52 1 0 0 0 0 27 46 2 0 0 0 0 27 56 1 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 30 42 1 6 0 0 0 31 50 1 6 0 0 0 32 51 1 1 0 0 0 33 35 1 0 0 0 0 33 52 1 6 0 0 0 34 37 1 0 0 0 0 34 53 1 6 0 0 0 35 38 1 0 0 0 0 35 54 1 1 0 0 0 36 42 1 0 0 0 0 36 47 2 0 0 0 0 37 41 1 0 0 0 0 37 53 1 1 0 0 0 38 41 1 0 0 0 0 38 55 1 1 0 0 0 39 48 2 0 0 0 0 39 54 1 0 0 0 0 40 49 2 0 0 0 0 40 55 1 0 0 0 0 42 56 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	776.3
Volume:	778.358
LogP:	4.716
LogD:	2.926
LogS:	-4.101
# Rotatable Bonds:	14
TPSA:	187.4
# H-Bond Aceptor:	14
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.155
Synthetic Accessibility Score:	5.83
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:	-5.226
MDCK Permeability:	5.2301649702712893e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.333
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	84.2640609741211%
Volume Distribution (VD):	2.406
Pgp-substrate:	11.600601196289062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.789
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.419

ADMET: Excretion

Clearance (CL):	3.786
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.989
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.915
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.09
Carcinogencity:	0.051
Eye Corrosion:	0.005
Eye Irritation:	0.052
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC82467

Natural Product ID:	NPC82467
*Common Name:**	Kansuinin F
IUPAC Name:	n.a.
Synonyms:	kansuinin F
Standard InCHIKey:	PJXPCKIXYVFTNT-HOZRDUKESA-N
Standard InCHI:	InChI=1S/C42H48O14/c1-21-20-42(56-27(7)46)30(31(21)50-24(4)43)32(51-25(5)44)22(2)33(52-26(6)45)35(54-39(48)28-16-12-10-13-17-28)38(55-40(49)29-18-14-11-15-19-29)41(8,9)37-34(53-37)23(3)36(42)47/h10-19,21,23,30-35,37-38H,2,20H2,1,3-9H3/t21-,23+,30+,31-,32-,33-,34+,35+,37-,38+,42+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)C)[C@H](C(=C)[C@@H]([C@H]([C@H](C(C)(C)[C@@H]1[C@@H]([C@@H](C)C2=O)O1)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508061
PubChem CID:	21589731
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic 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
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	ED50	>	50.0	ug ml-1	PMID[564516]

☑ 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 NPC82467 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	363
0.1-0.2	1242
0.2-0.3	2519
0.3-0.4	6287
0.4-0.5	11808
0.5-0.6	11704
0.6-0.7	7774
0.7-0.8	799
0.8-0.85	75
0.85-0.9	56
0.9-0.95	59
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9781	High Similarity	NPC477095
0.963	High Similarity	NPC475660
0.9627	High Similarity	NPC86772
0.9571	High Similarity	NPC25484
0.9571	High Similarity	NPC232583
0.9562	High Similarity	NPC477094
0.9562	High Similarity	NPC477096
0.9559	High Similarity	NPC473654
0.9556	High Similarity	NPC276652
0.9556	High Similarity	NPC272523
0.9556	High Similarity	NPC325805
0.9478	High Similarity	NPC475262
0.9478	High Similarity	NPC265459
0.9478	High Similarity	NPC290833
0.9429	High Similarity	NPC205389
0.9416	High Similarity	NPC473497
0.9407	High Similarity	NPC194769
0.9407	High Similarity	NPC285221
0.9403	High Similarity	NPC153617
0.9403	High Similarity	NPC472250
0.9371	High Similarity	NPC477100
0.9371	High Similarity	NPC477098
0.9333	High Similarity	NPC79699
0.9333	High Similarity	NPC270364
0.9281	High Similarity	NPC45307
0.9275	High Similarity	NPC475413
0.9275	High Similarity	NPC474303
0.9265	High Similarity	NPC477358
0.9161	High Similarity	NPC477099
0.9161	High Similarity	NPC477097
0.9161	High Similarity	NPC477101
0.9137	High Similarity	NPC242355
0.9137	High Similarity	NPC187566
0.9085	High Similarity	NPC170668
0.9065	High Similarity	NPC251294
0.8971	High Similarity	NPC477360
0.8963	High Similarity	NPC42234
0.8873	High Similarity	NPC153214
0.8824	High Similarity	NPC475671
0.8824	High Similarity	NPC475452
0.8824	High Similarity	NPC475508
0.8824	High Similarity	NPC122504
0.8824	High Similarity	NPC3450
0.8786	High Similarity	NPC327511
0.8786	High Similarity	NPC205305
0.8777	High Similarity	NPC472247
0.8767	High Similarity	NPC125033
0.8723	High Similarity	NPC53361
0.8723	High Similarity	NPC473301
0.8723	High Similarity	NPC121268
0.8705	High Similarity	NPC324898
0.8705	High Similarity	NPC298547
0.8705	High Similarity	NPC477368
0.8705	High Similarity	NPC134937
0.8705	High Similarity	NPC477359
0.8696	High Similarity	NPC233860
0.8686	High Similarity	NPC272946
0.8684	High Similarity	NPC55744
0.8643	High Similarity	NPC477367
0.8643	High Similarity	NPC279637
0.8643	High Similarity	NPC232888
0.8643	High Similarity	NPC149401
0.8633	High Similarity	NPC472248
0.8633	High Similarity	NPC477364
0.8571	High Similarity	NPC28836
0.8561	High Similarity	NPC239358
0.8542	High Similarity	NPC475135
0.8519	High Similarity	NPC8990
0.8514	High Similarity	NPC254558
0.8511	High Similarity	NPC200154
0.8493	Intermediate Similarity	NPC471100
0.8493	Intermediate Similarity	NPC25043
0.8493	Intermediate Similarity	NPC471107
0.8493	Intermediate Similarity	NPC134131
0.8483	Intermediate Similarity	NPC131966
0.8483	Intermediate Similarity	NPC191387
0.8477	Intermediate Similarity	NPC70344
0.8456	Intermediate Similarity	NPC477369
0.8451	Intermediate Similarity	NPC202729
0.844	Intermediate Similarity	NPC311492
0.8429	Intermediate Similarity	NPC233692
0.8392	Intermediate Similarity	NPC27721
0.8333	Intermediate Similarity	NPC51602
0.8311	Intermediate Similarity	NPC475552
0.8289	Intermediate Similarity	NPC282239
0.8289	Intermediate Similarity	NPC251139
0.8264	Intermediate Similarity	NPC184109
0.8243	Intermediate Similarity	NPC127857
0.8235	Intermediate Similarity	NPC217091
0.8235	Intermediate Similarity	NPC106895
0.8235	Intermediate Similarity	NPC11410
0.8231	Intermediate Similarity	NPC95449
0.8214	Intermediate Similarity	NPC37968
0.8212	Intermediate Similarity	NPC471103
0.8201	Intermediate Similarity	NPC477357
0.82	Intermediate Similarity	NPC473403
0.8182	Intermediate Similarity	NPC472393
0.8176	Intermediate Similarity	NPC40138
0.8176	Intermediate Similarity	NPC470231
0.817	Intermediate Similarity	NPC21410
0.817	Intermediate Similarity	NPC473670
0.817	Intermediate Similarity	NPC469456
0.8158	Intermediate Similarity	NPC138641
0.8158	Intermediate Similarity	NPC469647
0.8158	Intermediate Similarity	NPC22571
0.8158	Intermediate Similarity	NPC283875
0.8158	Intermediate Similarity	NPC469648
0.8146	Intermediate Similarity	NPC112216
0.8146	Intermediate Similarity	NPC7095
0.8143	Intermediate Similarity	NPC477370
0.8129	Intermediate Similarity	NPC477366
0.8129	Intermediate Similarity	NPC471102
0.8129	Intermediate Similarity	NPC477363
0.8121	Intermediate Similarity	NPC471162
0.8116	Intermediate Similarity	NPC477362
0.8105	Intermediate Similarity	NPC472030
0.8105	Intermediate Similarity	NPC473414
0.8105	Intermediate Similarity	NPC265395
0.8105	Intermediate Similarity	NPC158333
0.8105	Intermediate Similarity	NPC242262
0.8105	Intermediate Similarity	NPC237549
0.8105	Intermediate Similarity	NPC256142
0.8105	Intermediate Similarity	NPC304876
0.8105	Intermediate Similarity	NPC249471
0.8105	Intermediate Similarity	NPC1173
0.8105	Intermediate Similarity	NPC77719
0.8105	Intermediate Similarity	NPC257213
0.8105	Intermediate Similarity	NPC472005
0.8105	Intermediate Similarity	NPC472022
0.8095	Intermediate Similarity	NPC266374
0.8092	Intermediate Similarity	NPC101043
0.8092	Intermediate Similarity	NPC306799
0.8079	Intermediate Similarity	NPC250046
0.8079	Intermediate Similarity	NPC60509
0.8079	Intermediate Similarity	NPC81698
0.8071	Intermediate Similarity	NPC477365
0.8071	Intermediate Similarity	NPC472706
0.8056	Intermediate Similarity	NPC471911
0.8056	Intermediate Similarity	NPC4242
0.8052	Intermediate Similarity	NPC26033
0.8052	Intermediate Similarity	NPC114410
0.8052	Intermediate Similarity	NPC228204
0.8052	Intermediate Similarity	NPC112523
0.8052	Intermediate Similarity	NPC472549
0.8042	Intermediate Similarity	NPC472394
0.8041	Intermediate Similarity	NPC183540
0.8041	Intermediate Similarity	NPC182869
0.8039	Intermediate Similarity	NPC233581
0.8039	Intermediate Similarity	NPC145649
0.8027	Intermediate Similarity	NPC162613
0.8027	Intermediate Similarity	NPC477904
0.8027	Intermediate Similarity	NPC87934
0.8027	Intermediate Similarity	NPC183270
0.8026	Intermediate Similarity	NPC161239
0.8026	Intermediate Similarity	NPC198455
0.8026	Intermediate Similarity	NPC165260
0.8014	Intermediate Similarity	NPC472707
0.7987	Intermediate Similarity	NPC477894
0.7987	Intermediate Similarity	NPC219419
0.7986	Intermediate Similarity	NPC472704
0.7975	Intermediate Similarity	NPC43304
0.7975	Intermediate Similarity	NPC477190
0.7975	Intermediate Similarity	NPC477188
0.7974	Intermediate Similarity	NPC472398
0.7959	Intermediate Similarity	NPC9905
0.7956	Intermediate Similarity	NPC473243
0.7949	Intermediate Similarity	NPC469771
0.7947	Intermediate Similarity	NPC477737
0.7945	Intermediate Similarity	NPC52523
0.7945	Intermediate Similarity	NPC217673
0.7937	Intermediate Similarity	NPC477491
0.7937	Intermediate Similarity	NPC61891
0.7937	Intermediate Similarity	NPC324769
0.7937	Intermediate Similarity	NPC325732
0.7935	Intermediate Similarity	NPC259144
0.7935	Intermediate Similarity	NPC155329
0.7935	Intermediate Similarity	NPC114357
0.7935	Intermediate Similarity	NPC473611
0.7922	Intermediate Similarity	NPC472548
0.7922	Intermediate Similarity	NPC477905
0.7919	Intermediate Similarity	NPC63737
0.7919	Intermediate Similarity	NPC192658
0.7919	Intermediate Similarity	NPC472546
0.7917	Intermediate Similarity	NPC475569
0.7917	Intermediate Similarity	NPC469499
0.7917	Intermediate Similarity	NPC238370
0.7914	Intermediate Similarity	NPC472703
0.7908	Intermediate Similarity	NPC473214
0.7908	Intermediate Similarity	NPC470245
0.7905	Intermediate Similarity	NPC200592
0.7905	Intermediate Similarity	NPC43241
0.7905	Intermediate Similarity	NPC473085
0.7905	Intermediate Similarity	NPC184747
0.7905	Intermediate Similarity	NPC473613
0.7905	Intermediate Similarity	NPC48017
0.7905	Intermediate Similarity	NPC147880
0.7905	Intermediate Similarity	NPC473758
0.7905	Intermediate Similarity	NPC211137
0.7905	Intermediate Similarity	NPC476094
0.7905	Intermediate Similarity	NPC473112

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 NPC82467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	803
0.2-0.3	1643
0.3-0.4	2958
0.4-0.5	2230
0.5-0.6	964
0.6-0.7	249
0.7-0.8	11
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
0.8	Intermediate Similarity	NPD7236	Approved
0.7963	Intermediate Similarity	NPD7799	Discontinued
0.7857	Intermediate Similarity	NPD7239	Suspended
0.774	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7057	Phase 3
0.7407	Intermediate Similarity	NPD7058	Phase 2
0.7251	Intermediate Similarity	NPD8368	Discontinued
0.7251	Intermediate Similarity	NPD7685	Pre-registration
0.7226	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8407	Phase 2
0.7205	Intermediate Similarity	NPD6599	Discontinued
0.7153	Intermediate Similarity	NPD2067	Discontinued
0.7153	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7086	Intermediate Similarity	NPD7961	Discontinued
0.708	Intermediate Similarity	NPD2182	Approved
0.7073	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4628	Phase 3
0.7067	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8435	Approved
0.7048	Intermediate Similarity	NPD7075	Discontinued
0.7045	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6799	Approved
0.7021	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6287	Discontinued
0.6966	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8361	Approved
0.6966	Remote Similarity	NPD8360	Approved
0.6909	Remote Similarity	NPD6801	Discontinued
0.6901	Remote Similarity	NPD2629	Approved
0.6879	Remote Similarity	NPD6858	Approved
0.6879	Remote Similarity	NPD7094	Approved
0.6867	Remote Similarity	NPD6085	Phase 2
0.6867	Remote Similarity	NPD5760	Phase 2
0.6867	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5761	Phase 2
0.6866	Remote Similarity	NPD1238	Approved
0.6857	Remote Similarity	NPD6765	Approved
0.6857	Remote Similarity	NPD6764	Approved
0.6854	Remote Similarity	NPD8150	Discontinued
0.6853	Remote Similarity	NPD4198	Discontinued
0.6831	Remote Similarity	NPD8485	Approved
0.6828	Remote Similarity	NPD7741	Discontinued
0.6826	Remote Similarity	NPD5402	Approved
0.6826	Remote Similarity	NPD3817	Phase 2
0.6813	Remote Similarity	NPD3887	Approved
0.6813	Remote Similarity	NPD6190	Approved
0.6812	Remote Similarity	NPD6685	Approved
0.681	Remote Similarity	NPD5403	Approved
0.6798	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5401	Approved
0.6788	Remote Similarity	NPD164	Approved
0.6776	Remote Similarity	NPD6832	Phase 2
0.6774	Remote Similarity	NPD6355	Discontinued
0.6766	Remote Similarity	NPD7819	Suspended
0.6733	Remote Similarity	NPD5667	Approved
0.672	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2796	Approved
0.6704	Remote Similarity	NPD6784	Approved
0.6704	Remote Similarity	NPD6785	Approved
0.6703	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3764	Approved
0.6687	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5494	Approved
0.6646	Remote Similarity	NPD6273	Approved
0.6623	Remote Similarity	NPD7008	Discontinued
0.6623	Remote Similarity	NPD1876	Approved
0.6619	Remote Similarity	NPD5048	Discontinued
0.6606	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3972	Approved
0.6594	Remote Similarity	NPD5765	Approved
0.6591	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3882	Suspended
0.6587	Remote Similarity	NPD4380	Phase 2
0.6573	Remote Similarity	NPD6912	Phase 3
0.6562	Remote Similarity	NPD2353	Approved
0.6562	Remote Similarity	NPD5762	Approved
0.6562	Remote Similarity	NPD6002	Phase 3
0.6562	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5763	Approved
0.6562	Remote Similarity	NPD6004	Phase 3
0.6562	Remote Similarity	NPD6005	Phase 3
0.6562	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1237	Approved
0.6543	Remote Similarity	NPD2575	Approved
0.6541	Remote Similarity	NPD2799	Discontinued
0.6541	Remote Similarity	NPD7033	Discontinued
0.6541	Remote Similarity	NPD7305	Phase 1
0.6538	Remote Similarity	NPD7713	Phase 3
0.6536	Remote Similarity	NPD5647	Approved
0.6532	Remote Similarity	NPD8127	Discontinued
0.6529	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7458	Discontinued
0.6514	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD8462	Phase 1
0.6512	Remote Similarity	NPD919	Approved
0.651	Remote Similarity	NPD17	Approved
0.6506	Remote Similarity	NPD920	Approved
0.65	Remote Similarity	NPD7137	Phase 2
0.6496	Remote Similarity	NPD7798	Approved
0.6486	Remote Similarity	NPD9545	Approved
0.6485	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2569	Approved
0.6478	Remote Similarity	NPD2567	Approved
0.6477	Remote Similarity	NPD7473	Discontinued
0.6475	Remote Similarity	NPD1930	Approved
0.6475	Remote Similarity	NPD1929	Approved
0.6475	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2313	Discontinued
0.646	Remote Similarity	NPD1471	Phase 3
0.646	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD3926	Phase 2
0.6453	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6385	Approved
0.645	Remote Similarity	NPD7411	Suspended
0.645	Remote Similarity	NPD6386	Approved
0.6441	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5951	Approved
0.6429	Remote Similarity	NPD3226	Approved
0.6429	Remote Similarity	NPD2798	Approved
0.6424	Remote Similarity	NPD4807	Approved
0.6424	Remote Similarity	NPD4806	Approved
0.6415	Remote Similarity	NPD6653	Approved
0.6409	Remote Similarity	NPD8312	Approved
0.6409	Remote Similarity	NPD8313	Approved
0.6406	Remote Similarity	NPD8320	Phase 1
0.6406	Remote Similarity	NPD8319	Approved
0.6402	Remote Similarity	NPD2354	Approved
0.6402	Remote Similarity	NPD8285	Discontinued
0.64	Remote Similarity	NPD5306	Approved
0.64	Remote Similarity	NPD5305	Approved
0.6395	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1608	Approved
0.6382	Remote Similarity	NPD6637	Approved
0.637	Remote Similarity	NPD1202	Approved
0.6364	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4106	Approved
0.6358	Remote Similarity	NPD4135	Approved
0.6358	Remote Similarity	NPD4136	Approved
0.6358	Remote Similarity	NPD2346	Discontinued
0.6357	Remote Similarity	NPD6647	Phase 2
0.6354	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7808	Phase 3
0.6352	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD230	Phase 1
0.6348	Remote Similarity	NPD3818	Discontinued
0.6348	Remote Similarity	NPD3751	Discontinued
0.6346	Remote Similarity	NPD7055	Discontinued
0.6343	Remote Similarity	NPD1247	Approved
0.6335	Remote Similarity	NPD3748	Approved
0.6335	Remote Similarity	NPD1510	Phase 2
0.6333	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5585	Approved
0.6331	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6233	Phase 2
0.6329	Remote Similarity	NPD6663	Approved
0.6329	Remote Similarity	NPD8032	Phase 2
0.6328	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6166	Phase 2
0.6328	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1549	Phase 2
0.6316	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1934	Approved
0.6312	Remote Similarity	NPD5909	Discontinued
0.6307	Remote Similarity	NPD6232	Discontinued
0.6307	Remote Similarity	NPD3787	Discontinued
0.6306	Remote Similarity	NPD6039	Approved
0.6306	Remote Similarity	NPD7095	Approved
0.6301	Remote Similarity	NPD7768	Phase 2
0.6298	Remote Similarity	NPD7251	Discontinued
0.6296	Remote Similarity	NPD2935	Discontinued
0.6296	Remote Similarity	NPD2438	Suspended
0.6291	Remote Similarity	NPD5125	Phase 3
0.6291	Remote Similarity	NPD5126	Approved
0.6289	Remote Similarity	NPD1240	Approved
0.6287	Remote Similarity	NPD2534	Approved
0.6287	Remote Similarity	NPD2533	Approved
0.6287	Remote Similarity	NPD2532	Approved
0.6287	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5204	Approved
0.6282	Remote Similarity	NPD5736	Approved
0.628	Remote Similarity	NPD1243	Approved
0.6279	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD1989	Approved
0.6271	Remote Similarity	NPD5242	Approved
0.6269	Remote Similarity	NPD7435	Discontinued
0.6269	Remote Similarity	NPD7497	Discontinued
0.6267	Remote Similarity	NPD7009	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