NPASS Compound

Structure

CID214264 OpenBabel06191716002D 35 38 0 0 1 0 0 0 0 0999 V2000 2.5139 2.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4286 4.5216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8558 3.7322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5366 0.5244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2438 3.3299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6909 0.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6903 0.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8337 2.2635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3823 -1.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3818 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7245 2.6607 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6912 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8457 -0.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5372 -1.4638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6917 -1.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2272 -1.4633 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2269 -0.4870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8460 1.4637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0442 2.8363 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8258 3.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5369 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8466 2.4391 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 1.6920 -2.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1037 -1.9689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1031 0.0191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1456 3.8064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7167 4.0281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8167 2.5405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 22 1 0 0 0 0 9 26 1 0 0 0 0 10 28 1 0 0 0 0 11 15 1 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 25 1 0 0 0 0 15 1 1 6 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 29 2 0 0 0 0 20 21 1 0 0 0 0 20 30 1 6 0 0 0 21 31 1 6 0 0 0 22 26 1 6 0 0 0 22 27 1 0 0 0 0 23 27 1 0 0 0 0 23 32 1 6 0 0 0 24 33 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 6 0 0 0 27 6 1 6 0 0 0 27 34 1 0 0 0 0 28 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.32
Volume:	514.877
LogP:	1.989
LogD:	0.673
LogS:	-2.963
# Rotatable Bonds:	5
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	5.516
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.008
MDCK Permeability:	5.420201887318399e-06
Pgp-inhibitor:	0.031
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.054
20% Bioavailability (F20%):	0.416
30% Bioavailability (F30%):	0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	67.17400360107422%
Volume Distribution (VD):	0.667
Pgp-substrate:	19.49993896484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.687
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.184
CYP3A4-substrate:	0.48

ADMET: Excretion

Clearance (CL):	2.52
Half-life (T1/2):	0.517

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.74
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.505
Carcinogencity:	0.153
Eye Corrosion:	0.01
Eye Irritation:	0.107
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC214264

Natural Product ID:	NPC214264
*Common Name:**	Makisterone A
IUPAC Name:	(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:
Standard InCHIKey:	IJRBORPEVKCEQD-JMQWOFAPSA-N
Standard InCHI:	InChI=1S/C28H46O7/c1-15(24(2,3)33)11-23(32)27(6,34)22-8-10-28(35)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,15-16,18,20-23,30-35H,7-11,13-14H2,1-6H3/t15-,16+,18+,20-,21+,22+,23-,25-,26-,27-,28-/m1/s1
SMILES:	C[C@H](C[C@H]([C@@](C)([C@H]1CC[C@]2(C3=CC(=O)[C@@H]4C[C@H]([C@H](C[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O)O)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255034
PubChem CID:	12312690
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols 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
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[21417387]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[21417387]
NPO28005.1	Panax japonicus var. bipinnatifidus	Varieties	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[2618703]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28005.1	Panax japonicus var. bipinnatifidus	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28005.1	Panax japonicus var. bipinnatifidus	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4842	Limonium vulgare	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28005.1	Panax japonicus var. bipinnatifidus	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8139	Clostridium paraputrificum	Species	Clostridiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1557	Rhizoplaca chrysoleuca	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	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	6

Activity Type	# Activity
Individual Protein	2
Protein Complex	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	100000.0	nM	PMID[538514]
NPT3064	Individual Protein	Ecdysone receptor	Drosophila melanogaster	IC50	=	112.2	nM	PMID[538515]
NPT5226	Protein Complex	Ecdysone receptor	Spodoptera frugiperda	IC50	=	389.05	nM	PMID[538516]
NPT3079	Protein Complex	Ecdysone receptor	Nezara viridula	IC50	=	1380.38	nM	PMID[538516]
NPT5227	Protein Complex	Ecdysone receptor	Leptinotarsa decemlineata	IC50	=	1737.8	nM	PMID[538516]
NPT5228	Protein Complex	Ecdysone receptor	Drosophila melanogaster	IC50	=	1380.38	nM	PMID[538516]

☑ 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 NPC214264 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	203
0.1-0.2	1288
0.2-0.3	4406
0.3-0.4	8636
0.4-0.5	12604
0.5-0.6	6549
0.6-0.7	5959
0.7-0.8	2698
0.8-0.85	258
0.85-0.9	52
0.9-0.95	16
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC49958
1.0	High Similarity	NPC48733
1.0	High Similarity	NPC296945
1.0	High Similarity	NPC50692
1.0	High Similarity	NPC319077
1.0	High Similarity	NPC97202
1.0	High Similarity	NPC202167
1.0	High Similarity	NPC171137
1.0	High Similarity	NPC302607
1.0	High Similarity	NPC85829
1.0	High Similarity	NPC152695
1.0	High Similarity	NPC150531
1.0	High Similarity	NPC260268
1.0	High Similarity	NPC476027
0.9898	High Similarity	NPC475060
0.9898	High Similarity	NPC83744
0.9898	High Similarity	NPC220229
0.9897	High Similarity	NPC204833
0.9897	High Similarity	NPC209502
0.9798	High Similarity	NPC329417
0.9798	High Similarity	NPC217201
0.9796	High Similarity	NPC149047
0.97	High Similarity	NPC11710
0.9697	High Similarity	NPC477916
0.9691	High Similarity	NPC477915
0.9485	High Similarity	NPC154072
0.9417	High Similarity	NPC207251
0.9412	High Similarity	NPC76084
0.9327	High Similarity	NPC73300
0.9327	High Similarity	NPC108721
0.9327	High Similarity	NPC962
0.9327	High Similarity	NPC250109
0.9327	High Similarity	NPC317210
0.9238	High Similarity	NPC326542
0.9216	High Similarity	NPC65941
0.9151	High Similarity	NPC49492
0.9151	High Similarity	NPC266728
0.9126	High Similarity	NPC214644
0.91	High Similarity	NPC473424
0.9072	High Similarity	NPC271195
0.902	High Similarity	NPC323834
0.901	High Similarity	NPC191892
0.8969	High Similarity	NPC111015
0.8899	High Similarity	NPC475041
0.8835	High Similarity	NPC166607
0.8835	High Similarity	NPC257353
0.8818	High Similarity	NPC109973
0.8788	High Similarity	NPC249954
0.8776	High Similarity	NPC196227
0.875	High Similarity	NPC165873
0.8738	High Similarity	NPC160843
0.87	High Similarity	NPC190554
0.87	High Similarity	NPC18509
0.8687	High Similarity	NPC259286
0.8687	High Similarity	NPC200702
0.8673	High Similarity	NPC69454
0.8661	High Similarity	NPC222688
0.8661	High Similarity	NPC28532
0.8661	High Similarity	NPC269642
0.8641	High Similarity	NPC117185
0.8641	High Similarity	NPC311612
0.8641	High Similarity	NPC247957
0.8641	High Similarity	NPC55872
0.8641	High Similarity	NPC249187
0.8614	High Similarity	NPC103051
0.86	High Similarity	NPC49371
0.86	High Similarity	NPC471463
0.8586	High Similarity	NPC472977
0.8586	High Similarity	NPC8993
0.8586	High Similarity	NPC472976
0.8571	High Similarity	NPC63748
0.8571	High Similarity	NPC116726
0.8571	High Similarity	NPC233116
0.8571	High Similarity	NPC473998
0.8571	High Similarity	NPC185
0.8571	High Similarity	NPC475806
0.8558	High Similarity	NPC75531
0.8558	High Similarity	NPC149124
0.8558	High Similarity	NPC28656
0.8558	High Similarity	NPC72255
0.8557	High Similarity	NPC309603
0.8557	High Similarity	NPC477943
0.8557	High Similarity	NPC473999
0.8545	High Similarity	NPC471854
0.8544	High Similarity	NPC87351
0.8544	High Similarity	NPC204450
0.8544	High Similarity	NPC195290
0.8529	High Similarity	NPC144956
0.8529	High Similarity	NPC316964
0.8529	High Similarity	NPC110149
0.8529	High Similarity	NPC218383
0.8529	High Similarity	NPC15390
0.8505	High Similarity	NPC235077
0.85	High Similarity	NPC473170
0.85	High Similarity	NPC472932
0.85	High Similarity	NPC472485
0.8485	Intermediate Similarity	NPC472496
0.8485	Intermediate Similarity	NPC472930
0.8485	Intermediate Similarity	NPC109305
0.8469	Intermediate Similarity	NPC48010
0.8469	Intermediate Similarity	NPC136801
0.8469	Intermediate Similarity	NPC100313
0.8462	Intermediate Similarity	NPC236390
0.8455	Intermediate Similarity	NPC196931
0.8454	Intermediate Similarity	NPC328539
0.8416	Intermediate Similarity	NPC117133
0.84	Intermediate Similarity	NPC196485
0.84	Intermediate Similarity	NPC245972
0.8396	Intermediate Similarity	NPC43285
0.8396	Intermediate Similarity	NPC58370
0.8396	Intermediate Similarity	NPC144459
0.8384	Intermediate Similarity	NPC472978
0.8384	Intermediate Similarity	NPC155304
0.8384	Intermediate Similarity	NPC168027
0.8384	Intermediate Similarity	NPC185936
0.8381	Intermediate Similarity	NPC477812
0.8367	Intermediate Similarity	NPC472973
0.8367	Intermediate Similarity	NPC2983
0.8367	Intermediate Similarity	NPC186688
0.8367	Intermediate Similarity	NPC86319
0.8367	Intermediate Similarity	NPC32830
0.8367	Intermediate Similarity	NPC275740
0.8365	Intermediate Similarity	NPC22388
0.8365	Intermediate Similarity	NPC234892
0.8365	Intermediate Similarity	NPC136289
0.8365	Intermediate Similarity	NPC293753
0.835	Intermediate Similarity	NPC474720
0.835	Intermediate Similarity	NPC476274
0.835	Intermediate Similarity	NPC83709
0.8349	Intermediate Similarity	NPC280782
0.8333	Intermediate Similarity	NPC320306
0.8333	Intermediate Similarity	NPC107243
0.8333	Intermediate Similarity	NPC474938
0.8333	Intermediate Similarity	NPC474785
0.8317	Intermediate Similarity	NPC53565
0.8317	Intermediate Similarity	NPC297199
0.8317	Intermediate Similarity	NPC472824
0.8304	Intermediate Similarity	NPC257457
0.8304	Intermediate Similarity	NPC311554
0.8302	Intermediate Similarity	NPC60681
0.83	Intermediate Similarity	NPC470376
0.83	Intermediate Similarity	NPC470375
0.83	Intermediate Similarity	NPC475255
0.83	Intermediate Similarity	NPC474736
0.8286	Intermediate Similarity	NPC26478
0.8286	Intermediate Similarity	NPC111323
0.8286	Intermediate Similarity	NPC140723
0.8283	Intermediate Similarity	NPC134321
0.8283	Intermediate Similarity	NPC320026
0.8269	Intermediate Similarity	NPC472924
0.8269	Intermediate Similarity	NPC476223
0.8269	Intermediate Similarity	NPC302537
0.8269	Intermediate Similarity	NPC163372
0.8269	Intermediate Similarity	NPC476240
0.8269	Intermediate Similarity	NPC224720
0.8269	Intermediate Similarity	NPC471401
0.8269	Intermediate Similarity	NPC81530
0.8265	Intermediate Similarity	NPC143767
0.8265	Intermediate Similarity	NPC474668
0.8265	Intermediate Similarity	NPC133588
0.8265	Intermediate Similarity	NPC193360
0.8265	Intermediate Similarity	NPC470417
0.8265	Intermediate Similarity	NPC131470
0.8261	Intermediate Similarity	NPC473979
0.8252	Intermediate Similarity	NPC197386
0.8252	Intermediate Similarity	NPC48647
0.8252	Intermediate Similarity	NPC186810
0.8252	Intermediate Similarity	NPC10364
0.8252	Intermediate Similarity	NPC114274
0.8252	Intermediate Similarity	NPC477854
0.8247	Intermediate Similarity	NPC472985
0.8247	Intermediate Similarity	NPC469994
0.8247	Intermediate Similarity	NPC472986
0.8241	Intermediate Similarity	NPC470257
0.8235	Intermediate Similarity	NPC173272
0.8235	Intermediate Similarity	NPC192428
0.8235	Intermediate Similarity	NPC477853
0.823	Intermediate Similarity	NPC61520
0.8224	Intermediate Similarity	NPC472925
0.8224	Intermediate Similarity	NPC230541
0.8218	Intermediate Similarity	NPC292793
0.8218	Intermediate Similarity	NPC299100
0.8218	Intermediate Similarity	NPC103527
0.8218	Intermediate Similarity	NPC470957
0.8218	Intermediate Similarity	NPC280804
0.8218	Intermediate Similarity	NPC470958
0.8214	Intermediate Similarity	NPC218970
0.8208	Intermediate Similarity	NPC471293
0.8205	Intermediate Similarity	NPC470882
0.82	Intermediate Similarity	NPC189520
0.819	Intermediate Similarity	NPC119601
0.819	Intermediate Similarity	NPC308726
0.819	Intermediate Similarity	NPC185530
0.8182	Intermediate Similarity	NPC77263
0.8182	Intermediate Similarity	NPC472971
0.8182	Intermediate Similarity	NPC472002
0.8182	Intermediate Similarity	NPC71348
0.8182	Intermediate Similarity	NPC472970
0.8182	Intermediate Similarity	NPC250592
0.8182	Intermediate Similarity	NPC1015

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 NPC214264 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1569
0.2-0.3	3976
0.3-0.4	2277
0.4-0.5	666
0.5-0.6	168
0.6-0.7	149
0.7-0.8	117
0.8-0.85	46
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8725	High Similarity	NPD5211	Phase 2
0.87	High Similarity	NPD4755	Approved
0.8558	High Similarity	NPD5141	Approved
0.8557	High Similarity	NPD5328	Approved
0.8529	High Similarity	NPD5285	Approved
0.8529	High Similarity	NPD4700	Approved
0.8529	High Similarity	NPD4696	Approved
0.8529	High Similarity	NPD5286	Approved
0.8505	High Similarity	NPD4634	Approved
0.8485	Intermediate Similarity	NPD4202	Approved
0.8447	Intermediate Similarity	NPD5223	Approved
0.8384	Intermediate Similarity	NPD6079	Approved
0.8365	Intermediate Similarity	NPD5224	Approved
0.8365	Intermediate Similarity	NPD5225	Approved
0.8365	Intermediate Similarity	NPD5226	Approved
0.8365	Intermediate Similarity	NPD4633	Approved
0.8302	Intermediate Similarity	NPD6675	Approved
0.8302	Intermediate Similarity	NPD7128	Approved
0.8302	Intermediate Similarity	NPD5739	Approved
0.8302	Intermediate Similarity	NPD6402	Approved
0.8286	Intermediate Similarity	NPD4754	Approved
0.8286	Intermediate Similarity	NPD5174	Approved
0.8286	Intermediate Similarity	NPD5175	Approved
0.8273	Intermediate Similarity	NPD4632	Approved
0.8247	Intermediate Similarity	NPD3618	Phase 1
0.8241	Intermediate Similarity	NPD6373	Approved
0.8241	Intermediate Similarity	NPD6372	Approved
0.8235	Intermediate Similarity	NPD4697	Phase 3
0.8148	Intermediate Similarity	NPD7320	Approved
0.8148	Intermediate Similarity	NPD6899	Approved
0.8148	Intermediate Similarity	NPD6881	Approved
0.8131	Intermediate Similarity	NPD4768	Approved
0.8131	Intermediate Similarity	NPD4767	Approved
0.8091	Intermediate Similarity	NPD6650	Approved
0.8091	Intermediate Similarity	NPD6649	Approved
0.8058	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD5221	Approved
0.8058	Intermediate Similarity	NPD5222	Approved
0.8056	Intermediate Similarity	NPD5697	Approved
0.8056	Intermediate Similarity	NPD5701	Approved
0.8041	Intermediate Similarity	NPD3666	Approved
0.8041	Intermediate Similarity	NPD3665	Phase 1
0.8041	Intermediate Similarity	NPD3133	Approved
0.8018	Intermediate Similarity	NPD8297	Approved
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD4753	Phase 2
0.8	Intermediate Similarity	NPD6883	Approved
0.7982	Intermediate Similarity	NPD4729	Approved
0.7982	Intermediate Similarity	NPD4730	Approved
0.7982	Intermediate Similarity	NPD6011	Approved
0.7982	Intermediate Similarity	NPD5128	Approved
0.7981	Intermediate Similarity	NPD5173	Approved
0.7963	Intermediate Similarity	NPD6008	Approved
0.7928	Intermediate Similarity	NPD8130	Phase 1
0.7928	Intermediate Similarity	NPD6617	Approved
0.7928	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD6869	Approved
0.7928	Intermediate Similarity	NPD6847	Approved
0.7909	Intermediate Similarity	NPD6014	Approved
0.7909	Intermediate Similarity	NPD6012	Approved
0.7909	Intermediate Similarity	NPD6013	Approved
0.7895	Intermediate Similarity	NPD6009	Approved
0.7857	Intermediate Similarity	NPD4786	Approved
0.7857	Intermediate Similarity	NPD6882	Approved
0.7845	Intermediate Similarity	NPD6319	Approved
0.7845	Intermediate Similarity	NPD6054	Approved
0.7845	Intermediate Similarity	NPD6059	Approved
0.7838	Intermediate Similarity	NPD5249	Phase 3
0.7838	Intermediate Similarity	NPD5250	Approved
0.7838	Intermediate Similarity	NPD5251	Approved
0.7838	Intermediate Similarity	NPD5169	Approved
0.7838	Intermediate Similarity	NPD5247	Approved
0.7838	Intermediate Similarity	NPD5248	Approved
0.7838	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD5135	Approved
0.7835	Intermediate Similarity	NPD4221	Approved
0.7835	Intermediate Similarity	NPD4223	Phase 3
0.783	Intermediate Similarity	NPD7639	Approved
0.783	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD4629	Approved
0.7788	Intermediate Similarity	NPD5210	Approved
0.7778	Intermediate Similarity	NPD5329	Approved
0.7768	Intermediate Similarity	NPD5127	Approved
0.7768	Intermediate Similarity	NPD5216	Approved
0.7768	Intermediate Similarity	NPD5215	Approved
0.7768	Intermediate Similarity	NPD5217	Approved
0.7739	Intermediate Similarity	NPD7115	Discovery
0.7736	Intermediate Similarity	NPD7638	Approved
0.7727	Intermediate Similarity	NPD6412	Phase 2
0.7712	Intermediate Similarity	NPD6370	Approved
0.77	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4197	Approved
0.7667	Intermediate Similarity	NPD7507	Approved
0.7653	Intermediate Similarity	NPD3667	Approved
0.7647	Intermediate Similarity	NPD7604	Phase 2
0.7642	Intermediate Similarity	NPD6083	Phase 2
0.7642	Intermediate Similarity	NPD6084	Phase 2
0.7627	Intermediate Similarity	NPD6016	Approved
0.7627	Intermediate Similarity	NPD5983	Phase 2
0.7627	Intermediate Similarity	NPD6015	Approved
0.7596	Intermediate Similarity	NPD6399	Phase 3
0.7583	Intermediate Similarity	NPD7492	Approved
0.7565	Intermediate Similarity	NPD5167	Approved
0.7563	Intermediate Similarity	NPD5988	Approved
0.7525	Intermediate Similarity	NPD5205	Approved
0.7525	Intermediate Similarity	NPD4689	Approved
0.7525	Intermediate Similarity	NPD4688	Approved
0.7525	Intermediate Similarity	NPD4690	Approved
0.7525	Intermediate Similarity	NPD4693	Phase 3
0.7525	Intermediate Similarity	NPD4138	Approved
0.7521	Intermediate Similarity	NPD6616	Approved
0.7521	Intermediate Similarity	NPD6336	Discontinued
0.7521	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD5284	Approved
0.748	Intermediate Similarity	NPD7319	Approved
0.7459	Intermediate Similarity	NPD7078	Approved
0.7459	Intermediate Similarity	NPD8293	Discontinued
0.7458	Intermediate Similarity	NPD7101	Approved
0.7458	Intermediate Similarity	NPD7100	Approved
0.7453	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7525	Registered
0.7436	Intermediate Similarity	NPD6317	Approved
0.7407	Intermediate Similarity	NPD5696	Approved
0.74	Intermediate Similarity	NPD4788	Approved
0.7398	Intermediate Similarity	NPD6033	Approved
0.7398	Intermediate Similarity	NPD7736	Approved
0.7373	Intermediate Similarity	NPD6314	Approved
0.7373	Intermediate Similarity	NPD6313	Approved
0.7353	Intermediate Similarity	NPD5690	Phase 2
0.7353	Intermediate Similarity	NPD6684	Approved
0.7353	Intermediate Similarity	NPD5330	Approved
0.7353	Intermediate Similarity	NPD7521	Approved
0.7353	Intermediate Similarity	NPD7334	Approved
0.7353	Intermediate Similarity	NPD5280	Approved
0.7353	Intermediate Similarity	NPD5279	Phase 3
0.7353	Intermediate Similarity	NPD6409	Approved
0.7353	Intermediate Similarity	NPD7146	Approved
0.7353	Intermediate Similarity	NPD4694	Approved
0.7345	Intermediate Similarity	NPD5168	Approved
0.7333	Intermediate Similarity	NPD6909	Approved
0.7333	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6908	Approved
0.7315	Intermediate Similarity	NPD7902	Approved
0.729	Intermediate Similarity	NPD5695	Phase 3
0.7281	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6053	Discontinued
0.7212	Intermediate Similarity	NPD6903	Approved
0.7212	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7632	Discontinued
0.7196	Intermediate Similarity	NPD7748	Approved
0.7184	Intermediate Similarity	NPD4623	Approved
0.7184	Intermediate Similarity	NPD4519	Discontinued
0.7172	Intermediate Similarity	NPD4195	Approved
0.7167	Intermediate Similarity	NPD4522	Approved
0.7167	Intermediate Similarity	NPD7516	Approved
0.7157	Intermediate Similarity	NPD3668	Phase 3
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7143	Intermediate Similarity	NPD6904	Approved
0.7087	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7328	Approved
0.7083	Intermediate Similarity	NPD7327	Approved
0.7073	Intermediate Similarity	NPD6067	Discontinued
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6868	Approved
0.7048	Intermediate Similarity	NPD6672	Approved
0.7048	Intermediate Similarity	NPD5737	Approved
0.7043	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6001	Approved
0.7009	Intermediate Similarity	NPD8035	Phase 2
0.7009	Intermediate Similarity	NPD8034	Phase 2
0.7009	Intermediate Similarity	NPD5693	Phase 1
0.6967	Remote Similarity	NPD8377	Approved
0.6967	Remote Similarity	NPD8294	Approved
0.6952	Remote Similarity	NPD7524	Approved
0.6939	Remote Similarity	NPD7339	Approved
0.6939	Remote Similarity	NPD3703	Phase 2
0.6939	Remote Similarity	NPD6942	Approved
0.6937	Remote Similarity	NPD4225	Approved
0.6935	Remote Similarity	NPD8328	Phase 3
0.6916	Remote Similarity	NPD4096	Approved
0.6911	Remote Similarity	NPD8335	Approved
0.6911	Remote Similarity	NPD8380	Approved
0.6911	Remote Similarity	NPD7503	Approved
0.6911	Remote Similarity	NPD8033	Approved
0.6911	Remote Similarity	NPD8379	Approved
0.6911	Remote Similarity	NPD8296	Approved
0.6911	Remote Similarity	NPD8378	Approved
0.6903	Remote Similarity	NPD5091	Approved
0.69	Remote Similarity	NPD3617	Approved
0.6897	Remote Similarity	NPD6686	Approved
0.6887	Remote Similarity	NPD5208	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