NPASS Compound

Structure

CID25511 OpenBabel06191715352D 31 35 0 0 1 0 0 0 0 0999 V2000 5.7003 0.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1706 0.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4389 1.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9480 0.5688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4598 -2.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0242 1.9073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8680 -1.4481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6391 0.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8193 1.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0977 -1.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6382 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6396 2.8380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2793 -1.8914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8201 2.3655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8190 -0.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6399 -1.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8201 -1.4189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7661 0.1970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0975 -0.4721 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6394 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6385 0.9460 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9465 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4586 2.3645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4592 -0.4725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4580 1.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4595 -1.4184 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8195 1.4195 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8198 -0.4730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3083 2.8545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 6 0 0 0 25 27 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	490.807
LogP:	6.683
LogD:	5.844
LogS:	-6.35
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	4.663
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.236
MDCK Permeability:	3.6766847188118845e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.152
30% Bioavailability (F30%):	0.825

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.9804458618164%
Volume Distribution (VD):	1.236
Pgp-substrate:	1.6436824798583984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.606
CYP2C19-inhibitor:	0.096
CYP2C19-substrate:	0.956
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.741
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.467

ADMET: Excretion

Clearance (CL):	3.489
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.766
Skin Sensitization:	0.526
Carcinogencity:	0.001
Eye Corrosion:	0.994
Eye Irritation:	0.926
Respiratory Toxicity:	0.253

Download Data

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

Natural Product: NPC25511

Natural Product ID:	NPC25511
*Common Name:**	Epilupeol
IUPAC Name:	(1R,3aR,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms:
Standard InCHIKey:	MQYXUWHLBZFQQO-ISZJTHHZSA-N
Standard InCHI:	InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24+,25+,27+,28-,29+,30+/m0/s1
SMILES:	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459702
PubChem CID:	5270628
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104489]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195447]
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant	n.a.	n.a.	PMID[24467317]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	Gum resin	n.a.	n.a.	PMID[26457560]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9225	Bursera graveolens	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5740	Phellodendron japonicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9225	Bursera graveolens	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5740	Phellodendron japonicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5740	Phellodendron japonicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9225	Bursera graveolens	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15315	Boswellia carterii	Species	Burseraceae	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	7
MIC	1
Others	1

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	127.2	ug.mL-1	PMID[455131]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[455132]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[455132]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	13.4	ug.mL-1	PMID[455131]
NPT2	Others	Unspecified		Ratio	=	10.4	n.a.	PMID[455131]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[455132]

☑ 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 NPC25511 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	185
0.1-0.2	2452
0.2-0.3	13217
0.3-0.4	12558
0.4-0.5	5266
0.5-0.6	4327
0.6-0.7	3366
0.7-0.8	1060
0.8-0.85	143
0.85-0.9	92
0.9-0.95	14
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62657
1.0	High Similarity	NPC192638
0.9855	High Similarity	NPC104387
0.9855	High Similarity	NPC240235
0.9855	High Similarity	NPC178383
0.9855	High Similarity	NPC231256
0.9855	High Similarity	NPC212879
0.9714	High Similarity	NPC78067
0.9714	High Similarity	NPC278091
0.9714	High Similarity	NPC86305
0.9714	High Similarity	NPC14112
0.9714	High Similarity	NPC93662
0.9706	High Similarity	NPC111234
0.9577	High Similarity	NPC248830
0.9577	High Similarity	NPC212241
0.9577	High Similarity	NPC119355
0.9577	High Similarity	NPC202540
0.9559	High Similarity	NPC45296
0.9444	High Similarity	NPC42853
0.9444	High Similarity	NPC102708
0.9429	High Similarity	NPC49168
0.9429	High Similarity	NPC254509
0.9429	High Similarity	NPC5046
0.9429	High Similarity	NPC196358
0.9429	High Similarity	NPC145552
0.9315	High Similarity	NPC80297
0.9315	High Similarity	NPC116119
0.9315	High Similarity	NPC472742
0.9315	High Similarity	NPC49599
0.9315	High Similarity	NPC49627
0.9315	High Similarity	NPC475727
0.9296	High Similarity	NPC3403
0.9296	High Similarity	NPC200243
0.9296	High Similarity	NPC185536
0.9296	High Similarity	NPC70982
0.9296	High Similarity	NPC230704
0.9286	High Similarity	NPC195489
0.9189	High Similarity	NPC475679
0.9167	High Similarity	NPC237460
0.9167	High Similarity	NPC91573
0.9155	High Similarity	NPC472503
0.9155	High Similarity	NPC308440
0.9143	High Similarity	NPC301226
0.9041	High Similarity	NPC331618
0.9041	High Similarity	NPC257191
0.9014	High Similarity	NPC211009
0.8919	High Similarity	NPC85346
0.8919	High Similarity	NPC285761
0.8919	High Similarity	NPC477819
0.8919	High Similarity	NPC301707
0.8919	High Similarity	NPC167037
0.8919	High Similarity	NPC244385
0.8919	High Similarity	NPC472342
0.8919	High Similarity	NPC31828
0.8919	High Similarity	NPC302041
0.8919	High Similarity	NPC65897
0.8919	High Similarity	NPC138621
0.8919	High Similarity	NPC6978
0.8919	High Similarity	NPC477817
0.8904	High Similarity	NPC189883
0.8831	High Similarity	NPC5280
0.8831	High Similarity	NPC246956
0.8831	High Similarity	NPC475726
0.8831	High Similarity	NPC472743
0.8824	High Similarity	NPC476737
0.8824	High Similarity	NPC27243
0.88	High Similarity	NPC80530
0.88	High Similarity	NPC273410
0.8784	High Similarity	NPC260301
0.8784	High Similarity	NPC307336
0.8784	High Similarity	NPC138502
0.8767	High Similarity	NPC257347
0.8767	High Similarity	NPC121744
0.8767	High Similarity	NPC322353
0.8767	High Similarity	NPC103822
0.8767	High Similarity	NPC471723
0.8767	High Similarity	NPC141071
0.8767	High Similarity	NPC144075
0.8767	High Similarity	NPC118508
0.8718	High Similarity	NPC475745
0.8718	High Similarity	NPC474482
0.8718	High Similarity	NPC264665
0.8718	High Similarity	NPC74595
0.8696	High Similarity	NPC142712
0.8684	High Similarity	NPC102253
0.8684	High Similarity	NPC13554
0.8684	High Similarity	NPC322313
0.8684	High Similarity	NPC78545
0.8684	High Similarity	NPC71535
0.8684	High Similarity	NPC236237
0.8667	High Similarity	NPC472499
0.8667	High Similarity	NPC472500
0.8667	High Similarity	NPC312328
0.8667	High Similarity	NPC472501
0.8649	High Similarity	NPC122418
0.8649	High Similarity	NPC134330
0.8649	High Similarity	NPC38141
0.8649	High Similarity	NPC46160
0.8649	High Similarity	NPC120098
0.8649	High Similarity	NPC129165
0.8649	High Similarity	NPC290598
0.8649	High Similarity	NPC30590
0.8649	High Similarity	NPC202642
0.8649	High Similarity	NPC300324
0.8649	High Similarity	NPC73875
0.8649	High Similarity	NPC27765
0.8649	High Similarity	NPC240604
0.8649	High Similarity	NPC265328
0.863	High Similarity	NPC476736
0.863	High Similarity	NPC100334
0.8611	High Similarity	NPC164045
0.8608	High Similarity	NPC264317
0.8608	High Similarity	NPC294438
0.8608	High Similarity	NPC292553
0.859	High Similarity	NPC470929
0.8571	High Similarity	NPC48079
0.8553	High Similarity	NPC1319
0.8553	High Similarity	NPC24504
0.8553	High Similarity	NPC476316
0.8533	High Similarity	NPC157996
0.8533	High Similarity	NPC214570
0.8533	High Similarity	NPC101475
0.8533	High Similarity	NPC34177
0.8533	High Similarity	NPC40394
0.8514	High Similarity	NPC136188
0.8514	High Similarity	NPC22105
0.8514	High Similarity	NPC230301
0.8514	High Similarity	NPC285893
0.8514	High Similarity	NPC162742
0.8514	High Similarity	NPC134847
0.8514	High Similarity	NPC288035
0.8514	High Similarity	NPC138374
0.8514	High Similarity	NPC304309
0.8514	High Similarity	NPC28657
0.8514	High Similarity	NPC34700
0.85	High Similarity	NPC12774
0.85	High Similarity	NPC472738
0.85	High Similarity	NPC168231
0.85	High Similarity	NPC2783
0.85	High Similarity	NPC98236
0.85	High Similarity	NPC269396
0.8493	Intermediate Similarity	NPC201373
0.8493	Intermediate Similarity	NPC472506
0.8481	Intermediate Similarity	NPC474233
0.8481	Intermediate Similarity	NPC209802
0.8462	Intermediate Similarity	NPC248886
0.8462	Intermediate Similarity	NPC477599
0.8462	Intermediate Similarity	NPC296701
0.8462	Intermediate Similarity	NPC218616
0.8451	Intermediate Similarity	NPC472741
0.8442	Intermediate Similarity	NPC47149
0.8442	Intermediate Similarity	NPC236112
0.8442	Intermediate Similarity	NPC206735
0.8421	Intermediate Similarity	NPC186191
0.8421	Intermediate Similarity	NPC300499
0.8421	Intermediate Similarity	NPC472502
0.8421	Intermediate Similarity	NPC475
0.8421	Intermediate Similarity	NPC275910
0.8421	Intermediate Similarity	NPC22955
0.8421	Intermediate Similarity	NPC205455
0.8421	Intermediate Similarity	NPC196753
0.8421	Intermediate Similarity	NPC99168
0.8421	Intermediate Similarity	NPC253807
0.8421	Intermediate Similarity	NPC470396
0.8421	Intermediate Similarity	NPC98386
0.8421	Intermediate Similarity	NPC158662
0.8421	Intermediate Similarity	NPC474989
0.8421	Intermediate Similarity	NPC230295
0.84	Intermediate Similarity	NPC113733
0.84	Intermediate Similarity	NPC470362
0.84	Intermediate Similarity	NPC321016
0.84	Intermediate Similarity	NPC107059
0.84	Intermediate Similarity	NPC321381
0.84	Intermediate Similarity	NPC106364
0.8395	Intermediate Similarity	NPC264005
0.8395	Intermediate Similarity	NPC33768
0.8395	Intermediate Similarity	NPC4643
0.8395	Intermediate Similarity	NPC269360
0.8395	Intermediate Similarity	NPC57469
0.8382	Intermediate Similarity	NPC71460
0.8382	Intermediate Similarity	NPC148174
0.8382	Intermediate Similarity	NPC218585
0.8378	Intermediate Similarity	NPC469534
0.8378	Intermediate Similarity	NPC469533
0.8378	Intermediate Similarity	NPC469593
0.8354	Intermediate Similarity	NPC110778
0.8354	Intermediate Similarity	NPC207013
0.8354	Intermediate Similarity	NPC113978
0.8354	Intermediate Similarity	NPC232023
0.8354	Intermediate Similarity	NPC85095
0.8354	Intermediate Similarity	NPC211135
0.8354	Intermediate Similarity	NPC477818
0.8354	Intermediate Similarity	NPC216420
0.8333	Intermediate Similarity	NPC129829
0.8333	Intermediate Similarity	NPC210323
0.8333	Intermediate Similarity	NPC157655
0.8333	Intermediate Similarity	NPC474531
0.8333	Intermediate Similarity	NPC254037
0.8312	Intermediate Similarity	NPC201459
0.8312	Intermediate Similarity	NPC30986

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 NPC25511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	2753
0.2-0.3	4334
0.3-0.4	1276
0.4-0.5	231
0.5-0.6	154
0.6-0.7	161
0.7-0.8	37
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD7525	Registered
0.8608	High Similarity	NPD7520	Clinical (unspecified phase)
0.8514	High Similarity	NPD7339	Approved
0.8514	High Similarity	NPD6942	Approved
0.8312	Intermediate Similarity	NPD7645	Phase 2
0.7922	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8034	Phase 2
0.7791	Intermediate Similarity	NPD8035	Phase 2
0.7662	Intermediate Similarity	NPD6924	Approved
0.7662	Intermediate Similarity	NPD6926	Approved
0.7632	Intermediate Similarity	NPD7151	Approved
0.7632	Intermediate Similarity	NPD7152	Approved
0.7632	Intermediate Similarity	NPD7150	Approved
0.7632	Intermediate Similarity	NPD4243	Approved
0.76	Intermediate Similarity	NPD6922	Approved
0.76	Intermediate Similarity	NPD6923	Approved
0.759	Intermediate Similarity	NPD4786	Approved
0.7558	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD4787	Phase 1
0.75	Intermediate Similarity	NPD7144	Approved
0.75	Intermediate Similarity	NPD7143	Approved
0.747	Intermediate Similarity	NPD4788	Approved
0.7468	Intermediate Similarity	NPD6933	Approved
0.7436	Intermediate Similarity	NPD4785	Approved
0.7436	Intermediate Similarity	NPD4784	Approved
0.7412	Intermediate Similarity	NPD3618	Phase 1
0.7403	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6079	Approved
0.7349	Intermediate Similarity	NPD3667	Approved
0.7317	Intermediate Similarity	NPD4748	Discontinued
0.725	Intermediate Similarity	NPD6117	Approved
0.7215	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6929	Approved
0.7191	Intermediate Similarity	NPD7515	Phase 2
0.716	Intermediate Similarity	NPD6116	Phase 1
0.7143	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4190	Phase 3
0.7125	Intermediate Similarity	NPD5275	Approved
0.7111	Intermediate Similarity	NPD4202	Approved
0.7108	Intermediate Similarity	NPD6930	Phase 2
0.7108	Intermediate Similarity	NPD6931	Approved
0.7108	Intermediate Similarity	NPD7509	Discontinued
0.7073	Intermediate Similarity	NPD6118	Approved
0.7073	Intermediate Similarity	NPD6697	Approved
0.7073	Intermediate Similarity	NPD6114	Approved
0.7073	Intermediate Similarity	NPD6115	Approved
0.6977	Remote Similarity	NPD3665	Phase 1
0.6977	Remote Similarity	NPD3666	Approved
0.6977	Remote Similarity	NPD3133	Approved
0.6951	Remote Similarity	NPD6925	Approved
0.6951	Remote Similarity	NPD6932	Approved
0.6951	Remote Similarity	NPD5776	Phase 2
0.6915	Remote Similarity	NPD7638	Approved
0.6914	Remote Similarity	NPD3703	Phase 2
0.6905	Remote Similarity	NPD6928	Phase 2
0.6882	Remote Similarity	NPD4697	Phase 3
0.6882	Remote Similarity	NPD5222	Approved
0.6882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5221	Approved
0.6867	Remote Similarity	NPD7145	Approved
0.686	Remote Similarity	NPD6695	Phase 3
0.6848	Remote Similarity	NPD7748	Approved
0.6842	Remote Similarity	NPD7640	Approved
0.6842	Remote Similarity	NPD7639	Approved
0.6835	Remote Similarity	NPD4245	Approved
0.6835	Remote Similarity	NPD4244	Approved
0.6835	Remote Similarity	NPD4789	Approved
0.6809	Remote Similarity	NPD4755	Approved
0.6809	Remote Similarity	NPD5173	Approved
0.6795	Remote Similarity	NPD5360	Phase 3
0.6795	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4195	Approved
0.6786	Remote Similarity	NPD6683	Phase 2
0.6782	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6399	Phase 3
0.6709	Remote Similarity	NPD3698	Phase 2
0.6706	Remote Similarity	NPD7514	Phase 3
0.6705	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6632	Remote Similarity	NPD7902	Approved
0.6629	Remote Similarity	NPD5279	Phase 3
0.6628	Remote Similarity	NPD6902	Approved
0.6623	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5223	Approved
0.6593	Remote Similarity	NPD4753	Phase 2
0.6591	Remote Similarity	NPD3668	Phase 3
0.6562	Remote Similarity	NPD5290	Discontinued
0.6556	Remote Similarity	NPD7524	Approved
0.6556	Remote Similarity	NPD7750	Discontinued
0.6552	Remote Similarity	NPD4221	Approved
0.6552	Remote Similarity	NPD4223	Phase 3
0.6531	Remote Similarity	NPD5224	Approved
0.6531	Remote Similarity	NPD5226	Approved
0.6531	Remote Similarity	NPD5225	Approved
0.6531	Remote Similarity	NPD4633	Approved
0.6531	Remote Similarity	NPD5211	Phase 2
0.6517	Remote Similarity	NPD5329	Approved
0.6512	Remote Similarity	NPD7332	Phase 2
0.6506	Remote Similarity	NPD8264	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3671	Phase 1
0.6465	Remote Similarity	NPD5175	Approved
0.6465	Remote Similarity	NPD4754	Approved
0.6465	Remote Similarity	NPD5174	Approved
0.6437	Remote Similarity	NPD6898	Phase 1
0.6404	Remote Similarity	NPD4197	Approved
0.64	Remote Similarity	NPD5141	Approved
0.6375	Remote Similarity	NPD6705	Phase 1
0.6373	Remote Similarity	NPD6899	Approved
0.6373	Remote Similarity	NPD7320	Approved
0.6373	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD7632	Discontinued
0.6341	Remote Similarity	NPD4758	Discontinued
0.6337	Remote Similarity	NPD4768	Approved
0.6337	Remote Similarity	NPD4767	Approved
0.6324	Remote Similarity	NPD385	Approved
0.6324	Remote Similarity	NPD384	Approved
0.6316	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7900	Approved
0.6311	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6373	Approved
0.6289	Remote Similarity	NPD6084	Phase 2
0.6289	Remote Similarity	NPD6083	Phase 2
0.6279	Remote Similarity	NPD3617	Approved
0.6277	Remote Similarity	NPD7087	Discontinued
0.6275	Remote Similarity	NPD5701	Approved
0.6275	Remote Similarity	NPD5697	Approved
0.6264	Remote Similarity	NPD4690	Approved
0.6264	Remote Similarity	NPD7146	Approved
0.6264	Remote Similarity	NPD4138	Approved
0.6264	Remote Similarity	NPD5330	Approved
0.6264	Remote Similarity	NPD7521	Approved
0.6264	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4693	Phase 3
0.6264	Remote Similarity	NPD7334	Approved
0.6264	Remote Similarity	NPD6684	Approved
0.6264	Remote Similarity	NPD4689	Approved
0.6264	Remote Similarity	NPD6409	Approved
0.6264	Remote Similarity	NPD4688	Approved
0.6264	Remote Similarity	NPD5205	Approved
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD4629	Approved
0.6237	Remote Similarity	NPD6051	Approved
0.6214	Remote Similarity	NPD5168	Approved
0.6214	Remote Similarity	NPD4730	Approved
0.6214	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD4729	Approved
0.6214	Remote Similarity	NPD5128	Approved
0.619	Remote Similarity	NPD6617	Approved
0.619	Remote Similarity	NPD6650	Approved
0.619	Remote Similarity	NPD6847	Approved
0.619	Remote Similarity	NPD8130	Phase 1
0.619	Remote Similarity	NPD6869	Approved
0.619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6649	Approved
0.617	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6700	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD7328	Approved
0.6147	Remote Similarity	NPD7327	Approved
0.6145	Remote Similarity	NPD6081	Approved
0.6132	Remote Similarity	NPD8297	Approved
0.6132	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD6903	Approved
0.6129	Remote Similarity	NPD4722	Approved
0.6129	Remote Similarity	NPD4723	Approved
0.6129	Remote Similarity	NPD6672	Approved
0.6129	Remote Similarity	NPD5737	Approved
0.6125	Remote Similarity	NPD4224	Phase 2
0.6105	Remote Similarity	NPD6703	Approved
0.6105	Remote Similarity	NPD6702	Approved
0.61	Remote Similarity	NPD4159	Approved
0.6095	Remote Similarity	NPD4634	Approved
0.6095	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5251	Approved
0.6095	Remote Similarity	NPD5248	Approved
0.6095	Remote Similarity	NPD5135	Approved
0.6095	Remote Similarity	NPD5249	Phase 3
0.6095	Remote Similarity	NPD5169	Approved
0.6095	Remote Similarity	NPD5247	Approved
0.6095	Remote Similarity	NPD5250	Approved
0.6092	Remote Similarity	NPD5364	Discontinued
0.6091	Remote Similarity	NPD7516	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