NPASS Compound

Structure

CID187566 OpenBabel06191715572D 48 52 0 0 1 0 0 0 0 0999 V2000 1.3459 -6.6421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9476 -3.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0215 -3.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9502 2.2637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2343 1.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4522 2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2139 1.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6584 0.2139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8645 -5.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8022 0.5594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9757 1.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7878 -0.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1349 0.5843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9469 -0.8721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6422 0.0943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0073 -0.7965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5036 -2.2646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6446 -0.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3034 -3.2064 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4674 -2.8844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9961 2.1345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5676 0.6005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1205 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6881 0.2236 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4183 -1.5581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3459 -4.9745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9543 -2.4275 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3459 -3.3070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0992 -0.5380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0046 -2.2698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2796 -0.8472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6122 -0.8222 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3230 1.1144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8250 -0.2680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4643 -1.4289 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6698 -1.7833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8721 -2.0109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4072 2.8961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5164 0.4376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7834 -2.4490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3087 -4.9745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2652 -1.8098 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 -0.5496 -3.0570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8645 -4.1408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4531 -0.3534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6310 1.2437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3365 -0.8800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 33 1 0 0 0 0 7 33 1 0 0 0 0 9 26 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 23 2 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 36 1 0 0 0 0 18 43 1 0 0 0 0 19 2 1 6 0 0 0 19 28 1 0 0 0 0 20 37 2 0 0 0 0 20 44 1 0 0 0 0 21 38 2 0 0 0 0 21 47 1 0 0 0 0 22 39 2 0 0 0 0 22 48 1 0 0 0 0 23 31 1 0 0 0 0 24 29 1 0 0 0 0 24 33 1 6 0 0 0 25 35 1 0 0 0 0 25 40 2 0 0 0 0 26 41 2 0 0 0 0 26 45 1 0 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 27 36 1 6 0 0 0 28 45 1 6 0 0 0 29 34 1 1 0 0 0 29 35 1 0 0 0 0 30 35 1 1 0 0 0 30 44 1 0 0 0 0 31 42 2 0 0 0 0 31 46 1 0 0 0 0 32 34 1 6 0 0 0 32 36 1 0 0 0 0 32 46 1 0 0 0 0 33 47 1 0 0 0 0 34 8 1 6 0 0 0 34 43 1 0 0 0 0 35 18 1 1 0 0 0 36 48 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	668.28
Volume:	667.548
LogP:	3.678
LogD:	1.912
LogS:	-4.138
# Rotatable Bonds:	13
TPSA:	157.8
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	6.106
Fsp3:	0.611
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:	-5.297
MDCK Permeability:	6.686607230221853e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.578
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.168
Plasma Protein Binding (PPB):	78.19339752197266%
Volume Distribution (VD):	1.678
Pgp-substrate:	16.537918090820312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.713
CYP3A4-substrate:	0.484

ADMET: Excretion

Clearance (CL):	3.056
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.687
Human Hepatotoxicity (H-HT):	0.984
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.803
Maximum Recommended Daily Dose:	0.812
Skin Sensitization:	0.684
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.79

Download Data

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

Natural Product: NPC187566

Natural Product ID:	NPC187566
*Common Name:**	Euphorbiaproliferin D
IUPAC Name:	n.a.
Synonyms:	Euphorbiaproliferin D
Standard InCHIKey:	SRKVJOIQCZXSCT-PQTFDODOSA-N
Standard InCHI:	InChI=1S/C36H44O12/c1-9-26(41)45-28-19(2)17-36(48-22(5)39)27(28)30(44-20(3)37)35-18-43-34(8,32(36)46-31(42)23-13-11-10-12-14-23)29(35)24(15-16-25(35)40)33(6,7)47-21(4)38/h10-16,19,24,27-30,32H,9,17-18H2,1-8H3/t19-,24-,27+,28-,29-,30+,32-,34+,35+,36+/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=CC1=O)C(C)(C)OC(=O)C)[C@@H]2OC(=O)c1ccccc1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1927833
PubChem CID:	56601276
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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	68.7	%	PMID[448503]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	71.3	%	PMID[448503]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	88.6	%	PMID[448503]

☑ 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 NPC187566 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	1251
0.2-0.3	2554
0.3-0.4	6688
0.4-0.5	12351
0.5-0.6	13585
0.6-0.7	5081
0.7-0.8	659
0.8-0.85	78
0.85-0.9	66
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC324898
0.9545	High Similarity	NPC298547
0.9545	High Similarity	NPC134937
0.9481	High Similarity	NPC251294
0.9474	High Similarity	NPC279637
0.9474	High Similarity	NPC149401
0.9333	High Similarity	NPC205305
0.9333	High Similarity	NPC327511
0.9333	High Similarity	NPC86772
0.9275	High Similarity	NPC153214
0.9265	High Similarity	NPC53361
0.9265	High Similarity	NPC272523
0.9265	High Similarity	NPC121268
0.9265	High Similarity	NPC325805
0.9254	High Similarity	NPC153617
0.9242	High Similarity	NPC475508
0.9185	High Similarity	NPC475262
0.9185	High Similarity	NPC265459
0.9185	High Similarity	NPC290833
0.9137	High Similarity	NPC82467
0.913	High Similarity	NPC473497
0.9118	High Similarity	NPC285221
0.9118	High Similarity	NPC194769
0.9111	High Similarity	NPC472250
0.9078	High Similarity	NPC170668
0.9058	High Similarity	NPC475660
0.9044	High Similarity	NPC79699
0.9	High Similarity	NPC477096
0.9	High Similarity	NPC45307
0.9	High Similarity	NPC477094
0.8993	High Similarity	NPC474303
0.8993	High Similarity	NPC475413
0.8993	High Similarity	NPC242355
0.8944	High Similarity	NPC477095
0.8905	High Similarity	NPC200154
0.8905	High Similarity	NPC270364
0.8881	High Similarity	NPC205389
0.8865	High Similarity	NPC131966
0.8865	High Similarity	NPC191387
0.8849	High Similarity	NPC276652
0.8824	High Similarity	NPC233860
0.8759	High Similarity	NPC472248
0.8759	High Similarity	NPC25484
0.8759	High Similarity	NPC232583
0.8723	High Similarity	NPC473654
0.8696	High Similarity	NPC28836
0.8686	High Similarity	NPC239358
0.8675	High Similarity	NPC55744
0.8662	High Similarity	NPC475135
0.863	High Similarity	NPC477099
0.863	High Similarity	NPC477101
0.863	High Similarity	NPC477097
0.8582	High Similarity	NPC473301
0.8581	High Similarity	NPC477098
0.8581	High Similarity	NPC477100
0.8571	High Similarity	NPC202729
0.8561	High Similarity	NPC311492
0.8551	High Similarity	NPC233692
0.854	High Similarity	NPC42234
0.854	High Similarity	NPC272946
0.8511	High Similarity	NPC27721
0.8503	High Similarity	NPC125033
0.85	High Similarity	NPC472247
0.8483	Intermediate Similarity	NPC25043
0.8483	Intermediate Similarity	NPC134131
0.8472	Intermediate Similarity	NPC95449
0.844	Intermediate Similarity	NPC477358
0.8417	Intermediate Similarity	NPC477360
0.8298	Intermediate Similarity	NPC477359
0.8298	Intermediate Similarity	NPC477368
0.8273	Intermediate Similarity	NPC122504
0.8273	Intermediate Similarity	NPC3450
0.8273	Intermediate Similarity	NPC475452
0.8273	Intermediate Similarity	NPC475671
0.8264	Intermediate Similarity	NPC477904
0.8264	Intermediate Similarity	NPC162613
0.8264	Intermediate Similarity	NPC87934
0.8264	Intermediate Similarity	NPC183270
0.8239	Intermediate Similarity	NPC477367
0.8239	Intermediate Similarity	NPC232888
0.8231	Intermediate Similarity	NPC471107
0.8231	Intermediate Similarity	NPC471100
0.8227	Intermediate Similarity	NPC477364
0.8224	Intermediate Similarity	NPC70344
0.8207	Intermediate Similarity	NPC266374
0.8194	Intermediate Similarity	NPC9905
0.8188	Intermediate Similarity	NPC472706
0.8182	Intermediate Similarity	NPC52523
0.8182	Intermediate Similarity	NPC217673
0.8176	Intermediate Similarity	NPC240115
0.8169	Intermediate Similarity	NPC4242
0.8169	Intermediate Similarity	NPC471911
0.8158	Intermediate Similarity	NPC469456
0.8156	Intermediate Similarity	NPC472394
0.8153	Intermediate Similarity	NPC324769
0.8153	Intermediate Similarity	NPC325732
0.8151	Intermediate Similarity	NPC192658
0.8151	Intermediate Similarity	NPC63737
0.8133	Intermediate Similarity	NPC254558
0.8102	Intermediate Similarity	NPC472704
0.8102	Intermediate Similarity	NPC8990
0.8079	Intermediate Similarity	NPC51602
0.8054	Intermediate Similarity	NPC312393
0.8054	Intermediate Similarity	NPC475552
0.805	Intermediate Similarity	NPC40138
0.8043	Intermediate Similarity	NPC477369
0.8041	Intermediate Similarity	NPC34943
0.8039	Intermediate Similarity	NPC251139
0.8029	Intermediate Similarity	NPC472703
0.8028	Intermediate Similarity	NPC469499
0.8026	Intermediate Similarity	NPC472548
0.8	Intermediate Similarity	NPC475373
0.7987	Intermediate Similarity	NPC125882
0.7987	Intermediate Similarity	NPC11410
0.7987	Intermediate Similarity	NPC127857
0.7986	Intermediate Similarity	NPC195647
0.7986	Intermediate Similarity	NPC66761
0.7986	Intermediate Similarity	NPC472577
0.7986	Intermediate Similarity	NPC17877
0.7986	Intermediate Similarity	NPC291638
0.7974	Intermediate Similarity	NPC471135
0.7962	Intermediate Similarity	NPC43304
0.7962	Intermediate Similarity	NPC477190
0.7962	Intermediate Similarity	NPC477188
0.7961	Intermediate Similarity	NPC161955
0.7961	Intermediate Similarity	NPC472398
0.7961	Intermediate Similarity	NPC471103
0.7947	Intermediate Similarity	NPC473403
0.7933	Intermediate Similarity	NPC478263
0.7933	Intermediate Similarity	NPC48599
0.7933	Intermediate Similarity	NPC20255
0.7933	Intermediate Similarity	NPC209592
0.7922	Intermediate Similarity	NPC21410
0.7922	Intermediate Similarity	NPC473670
0.7922	Intermediate Similarity	NPC472549
0.7922	Intermediate Similarity	NPC282239
0.7917	Intermediate Similarity	NPC474608
0.7911	Intermediate Similarity	NPC66193
0.7911	Intermediate Similarity	NPC322420
0.7911	Intermediate Similarity	NPC478073
0.7908	Intermediate Similarity	NPC22571
0.7908	Intermediate Similarity	NPC477905
0.7908	Intermediate Similarity	NPC283875
0.7908	Intermediate Similarity	NPC138641
0.7908	Intermediate Similarity	NPC469648
0.7908	Intermediate Similarity	NPC469647
0.7895	Intermediate Similarity	NPC7095
0.7895	Intermediate Similarity	NPC112216
0.7895	Intermediate Similarity	NPC91730
0.7891	Intermediate Similarity	NPC476094
0.7891	Intermediate Similarity	NPC4341
0.7891	Intermediate Similarity	NPC184747
0.7891	Intermediate Similarity	NPC473060
0.7891	Intermediate Similarity	NPC473440
0.7891	Intermediate Similarity	NPC147880
0.7891	Intermediate Similarity	NPC473112
0.7891	Intermediate Similarity	NPC473085
0.7891	Intermediate Similarity	NPC473109
0.7891	Intermediate Similarity	NPC475400
0.7891	Intermediate Similarity	NPC43241
0.7891	Intermediate Similarity	NPC473613
0.7891	Intermediate Similarity	NPC211137
0.7891	Intermediate Similarity	NPC200592
0.7891	Intermediate Similarity	NPC473081
0.7891	Intermediate Similarity	NPC48017
0.7891	Intermediate Similarity	NPC473758
0.7887	Intermediate Similarity	NPC147561
0.7881	Intermediate Similarity	NPC132652
0.7881	Intermediate Similarity	NPC473760
0.7881	Intermediate Similarity	NPC327031
0.7879	Intermediate Similarity	NPC474176
0.7872	Intermediate Similarity	NPC472707
0.7871	Intermediate Similarity	NPC475548
0.7871	Intermediate Similarity	NPC326235
0.7871	Intermediate Similarity	NPC217091
0.7871	Intermediate Similarity	NPC323001
0.7871	Intermediate Similarity	NPC475638
0.7871	Intermediate Similarity	NPC106895
0.7871	Intermediate Similarity	NPC290683
0.7867	Intermediate Similarity	NPC478264
0.7867	Intermediate Similarity	NPC311825
0.7867	Intermediate Similarity	NPC471162
0.7867	Intermediate Similarity	NPC92867
0.7862	Intermediate Similarity	NPC471134
0.7862	Intermediate Similarity	NPC473399
0.7862	Intermediate Similarity	NPC473216
0.7857	Intermediate Similarity	NPC476033
0.7857	Intermediate Similarity	NPC121272
0.7857	Intermediate Similarity	NPC477366
0.7843	Intermediate Similarity	NPC101043
0.7843	Intermediate Similarity	NPC197037
0.7843	Intermediate Similarity	NPC96308
0.7843	Intermediate Similarity	NPC306799
0.7842	Intermediate Similarity	NPC477362
0.7838	Intermediate Similarity	NPC16912
0.7832	Intermediate Similarity	NPC291419
0.7832	Intermediate Similarity	NPC470278
0.7832	Intermediate Similarity	NPC60825
0.7829	Intermediate Similarity	NPC81698
0.7829	Intermediate Similarity	NPC76103

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 NPC187566 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	814
0.2-0.3	1771
0.3-0.4	3096
0.4-0.5	2163
0.5-0.6	875
0.6-0.7	131
0.7-0.8	8
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
0.795	Intermediate Similarity	NPD7799	Discontinued
0.7748	Intermediate Similarity	NPD7236	Approved
0.7676	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7239	Suspended
0.7603	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2182	Approved
0.7178	Intermediate Similarity	NPD7058	Phase 2
0.7178	Intermediate Similarity	NPD7057	Phase 3
0.711	Intermediate Similarity	NPD8407	Phase 2
0.7091	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5760	Phase 2
0.7055	Intermediate Similarity	NPD5761	Phase 2
0.7047	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8368	Discontinued
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.6978	Remote Similarity	NPD6858	Approved
0.6978	Remote Similarity	NPD7094	Approved
0.6959	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6085	Phase 2
0.6943	Remote Similarity	NPD4628	Phase 3
0.6936	Remote Similarity	NPD7685	Pre-registration
0.6912	Remote Similarity	NPD6685	Approved
0.6906	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD164	Approved
0.6884	Remote Similarity	NPD2067	Discontinued
0.6859	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6005	Phase 3
0.6859	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6004	Phase 3
0.6859	Remote Similarity	NPD6002	Phase 3
0.6849	Remote Similarity	NPD6287	Discontinued
0.6839	Remote Similarity	NPD6764	Approved
0.6839	Remote Similarity	NPD6765	Approved
0.6806	Remote Similarity	NPD7741	Discontinued
0.678	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6599	Discontinued
0.6761	Remote Similarity	NPD690	Clinical (unspecified phase)
0.676	Remote Similarity	NPD8361	Approved
0.676	Remote Similarity	NPD8435	Approved
0.676	Remote Similarity	NPD8360	Approved
0.6732	Remote Similarity	NPD7961	Discontinued
0.6716	Remote Similarity	NPD1238	Approved
0.6691	Remote Similarity	NPD5765	Approved
0.6691	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7137	Phase 2
0.6685	Remote Similarity	NPD6784	Approved
0.6685	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD6912	Phase 3
0.6667	Remote Similarity	NPD2569	Approved
0.6667	Remote Similarity	NPD2567	Approved
0.6648	Remote Similarity	NPD8150	Discontinued
0.6648	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7819	Suspended
0.6647	Remote Similarity	NPD5494	Approved
0.6645	Remote Similarity	NPD6832	Phase 2
0.6643	Remote Similarity	NPD2629	Approved
0.6627	Remote Similarity	NPD7075	Discontinued
0.6623	Remote Similarity	NPD5647	Approved
0.6605	Remote Similarity	NPD6799	Approved
0.6585	Remote Similarity	NPD920	Approved
0.6585	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2796	Approved
0.6575	Remote Similarity	NPD9545	Approved
0.6571	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD8485	Approved
0.6541	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7055	Discontinued
0.6524	Remote Similarity	NPD6273	Approved
0.6519	Remote Similarity	NPD2799	Discontinued
0.6519	Remote Similarity	NPD7305	Phase 1
0.6512	Remote Similarity	NPD8127	Discontinued
0.6497	Remote Similarity	NPD6653	Approved
0.6494	Remote Similarity	NPD7008	Discontinued
0.649	Remote Similarity	NPD1876	Approved
0.6488	Remote Similarity	NPD6801	Discontinued
0.6483	Remote Similarity	NPD4198	Discontinued
0.6475	Remote Similarity	NPD5048	Discontinued
0.6467	Remote Similarity	NPD6637	Approved
0.6467	Remote Similarity	NPD3972	Approved
0.6467	Remote Similarity	NPD4380	Phase 2
0.6463	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2533	Approved
0.6463	Remote Similarity	NPD2532	Approved
0.6463	Remote Similarity	NPD2534	Approved
0.646	Remote Similarity	NPD2800	Approved
0.6449	Remote Similarity	NPD6647	Phase 2
0.6438	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD230	Phase 1
0.642	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7033	Discontinued
0.6412	Remote Similarity	NPD5402	Approved
0.6412	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD3817	Phase 2
0.641	Remote Similarity	NPD8462	Phase 1
0.641	Remote Similarity	NPD7713	Phase 3
0.641	Remote Similarity	NPD6663	Approved
0.6407	Remote Similarity	NPD7458	Discontinued
0.6407	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5403	Approved
0.638	Remote Similarity	NPD3887	Approved
0.638	Remote Similarity	NPD6190	Approved
0.6376	Remote Similarity	NPD17	Approved
0.6369	Remote Similarity	NPD7028	Phase 2
0.6364	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7473	Discontinued
0.6364	Remote Similarity	NPD5401	Approved
0.6364	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1243	Approved
0.6358	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7009	Phase 2
0.635	Remote Similarity	NPD7798	Approved
0.6346	Remote Similarity	NPD2313	Discontinued
0.6345	Remote Similarity	NPD6010	Discontinued
0.6341	Remote Similarity	NPD643	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6362	Approved
0.6337	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7497	Discontinued
0.6331	Remote Similarity	NPD1930	Approved
0.6331	Remote Similarity	NPD6385	Approved
0.6331	Remote Similarity	NPD6386	Approved
0.6331	Remote Similarity	NPD7411	Suspended
0.6331	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD1929	Approved
0.6329	Remote Similarity	NPD6355	Discontinued
0.6328	Remote Similarity	NPD3818	Discontinued
0.6324	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2575	Approved
0.6319	Remote Similarity	NPD8166	Discontinued
0.6316	Remote Similarity	NPD5353	Approved
0.6312	Remote Similarity	NPD3748	Approved
0.631	Remote Similarity	NPD3226	Approved
0.6306	Remote Similarity	NPD8032	Phase 2
0.6303	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD919	Approved
0.6301	Remote Similarity	NPD4766	Approved
0.6301	Remote Similarity	NPD5951	Approved
0.6299	Remote Similarity	NPD2798	Approved
0.6298	Remote Similarity	NPD8312	Approved
0.6298	Remote Similarity	NPD8313	Approved
0.6296	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6371	Approved
0.6289	Remote Similarity	NPD6651	Approved
0.6279	Remote Similarity	NPD3882	Suspended
0.6279	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5667	Approved
0.6267	Remote Similarity	NPD5126	Approved
0.6267	Remote Similarity	NPD5125	Phase 3
0.6258	Remote Similarity	NPD3661	Approved
0.6258	Remote Similarity	NPD3664	Approved
0.6258	Remote Similarity	NPD5736	Approved
0.6258	Remote Similarity	NPD7084	Phase 3
0.6258	Remote Similarity	NPD3662	Phase 3
0.6258	Remote Similarity	NPD3663	Approved
0.625	Remote Similarity	NPD3926	Phase 2
0.625	Remote Similarity	NPD1608	Approved
0.6243	Remote Similarity	NPD3749	Approved
0.6242	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5762	Approved
0.6235	Remote Similarity	NPD5763	Approved
0.6235	Remote Similarity	NPD2346	Discontinued
0.6233	Remote Similarity	NPD2652	Approved
0.6233	Remote Similarity	NPD2650	Approved
0.6232	Remote Similarity	NPD2066	Phase 3
0.6229	Remote Similarity	NPD7199	Phase 2
0.6226	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD1202	Approved
0.6218	Remote Similarity	NPD2613	Approved
0.6216	Remote Similarity	NPD9493	Approved
0.6216	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD2403	Approved
0.6211	Remote Similarity	NPD1510	Phase 2
0.6207	Remote Similarity	NPD969	Suspended
0.6201	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD1934	Approved
0.6196	Remote Similarity	NPD1549	Phase 2
0.6194	Remote Similarity	NPD1019	Discontinued
0.6193	Remote Similarity	NPD6808	Phase 2
0.6193	Remote Similarity	NPD6232	Discontinued
0.6193	Remote Similarity	NPD7315	Approved
0.6185	Remote Similarity	NPD7768	Phase 2
0.6184	Remote Similarity	NPD4806	Approved
0.6184	Remote Similarity	NPD4807	Approved
0.6184	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD4234	Approved
0.6181	Remote Similarity	NPD4233	Approved
0.6178	Remote Similarity	NPD6039	Approved
0.6174	Remote Similarity	NPD7610	Discontinued

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