NPASS Compound

Structure

CID260665 OpenBabel06191716062D 43 47 0 0 1 0 0 0 0 0999 V2000 -1.0574 3.0906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3244 2.7341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7985 1.7254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2464 3.2005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6335 2.9124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5320 3.7080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6811 4.1996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7364 3.8886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5306 0.7610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6800 1.2521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3823 2.2343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1290 5.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9790 2.2351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2632 -1.1381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3663 1.5371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2634 2.5133 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4273 3.7104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5317 2.7254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3817 1.2521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8299 3.7086 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8297 2.7259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9791 4.2002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6333 4.2876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2784 5.1826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3031 -0.9337 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1282 2.7267 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2775 4.2010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3540 -1.6630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3141 -1.4586 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6172 -0.5250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9601 0.2044 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6806 2.2343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1284 3.7094 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9203 -0.4087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2475 0.7517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7361 5.2639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4126 5.6830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2620 2.2269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0509 -2.5967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9712 -2.1880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5774 -0.3206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2632 1.1381 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 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 32 1 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 12 24 1 0 0 0 0 13 21 1 0 0 0 0 13 26 1 0 0 0 0 14 34 1 0 0 0 0 15 16 1 0 0 0 0 15 42 1 0 0 0 0 16 1 1 6 0 0 0 17 2 1 6 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 32 1 0 0 0 0 19 35 2 0 0 0 0 20 7 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 32 1 1 0 0 0 22 33 1 1 0 0 0 23 36 1 6 0 0 0 24 27 1 0 0 0 0 24 37 1 1 0 0 0 25 14 1 6 0 0 0 25 28 1 0 0 0 0 25 43 1 0 0 0 0 26 33 1 1 0 0 0 26 38 1 0 0 0 0 27 33 1 1 0 0 0 28 29 1 0 0 0 0 28 39 1 1 0 0 0 29 30 1 0 0 0 0 29 40 1 6 0 0 0 30 31 1 0 0 0 0 30 41 1 1 0 0 0 31 42 1 6 0 0 0 31 43 1 0 0 0 0 32 3 1 1 0 0 0 33 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.37
Volume:	619.171
LogP:	2.068
LogD:	2.325
LogS:	-3.159
# Rotatable Bonds:	9
TPSA:	177.14
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	5.553
Fsp3:	0.909
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.622
MDCK Permeability:	2.078529360005632e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	60.9587287902832%
Volume Distribution (VD):	0.374
Pgp-substrate:	12.281511306762695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.281
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	1.56
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.281
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.221
Skin Sensitization:	0.738
Carcinogencity:	0.111
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC260665

Natural Product ID:	NPC260665
*Common Name:**	(25R)-12Beta,16Beta,22Beta,26-(Beta-D-Glucopyranosyl)-Tetrahydroxycholest-4-En-3-One
IUPAC Name:	(8R,9S,10R,12R,13S,14S,16S,17R)-12,16-dihydroxy-17-[(2S,3S,6R)-3-hydroxy-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	KBOYYAOBNDMUQQ-GILNANDQSA-N
Standard InCHI:	InChI=1S/C33H54O10/c1-16(15-42-31-30(41)29(40)28(39)25(14-34)43-31)5-8-23(36)17(2)27-24(37)12-22-20-7-6-18-11-19(35)9-10-32(18,3)21(20)13-26(38)33(22,27)4/h11,16-17,20-31,34,36-41H,5-10,12-15H2,1-4H3/t16-,17-,20-,21+,22+,23+,24+,25-,26-,27+,28-,29+,30-,31-,32+,33-/m1/s1
SMILES:	C[C@H](CC[C@@H]([C@@H](C)[C@H]1[C@H](C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C[C@H]([C@]12C)O)O)O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337721
PubChem CID:	71568834
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662101]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO22127	Hosta longipes	Species	Asparagaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23411079]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21760	Bungarus multicinctus	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22926	Centaurea moschata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10886	Spiranthera odoratissima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19644	Dalea scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22127	Hosta longipes	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22474	Gnaphalium declinatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20423	Euryops imbricatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21093	Sinularia gonatodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19090	Polygonatum officinale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	94.8	%	PMID[478346]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	46300.0	nM	PMID[478346]

☑ 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 NPC260665 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	241
0.1-0.2	1494
0.2-0.3	4968
0.3-0.4	10159
0.4-0.5	10729
0.5-0.6	6048
0.6-0.7	4765
0.7-0.8	3204
0.8-0.85	950
0.85-0.9	113
0.9-0.95	25
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9439	High Similarity	NPC477944
0.9352	High Similarity	NPC477580
0.9352	High Similarity	NPC74727
0.934	High Similarity	NPC475317
0.934	High Similarity	NPC52241
0.934	High Similarity	NPC154856
0.9286	High Similarity	NPC28532
0.9259	High Similarity	NPC178981
0.9252	High Similarity	NPC263827
0.9252	High Similarity	NPC250481
0.9252	High Similarity	NPC285410
0.9245	High Similarity	NPC246205
0.9167	High Similarity	NPC130427
0.9167	High Similarity	NPC210420
0.9167	High Similarity	NPC474265
0.9159	High Similarity	NPC129340
0.9107	High Similarity	NPC471406
0.9099	High Similarity	NPC239293
0.9074	High Similarity	NPC269466
0.9065	High Similarity	NPC265655
0.9043	High Similarity	NPC47113
0.9043	High Similarity	NPC174367
0.9027	High Similarity	NPC476675
0.9	High Similarity	NPC474557
0.9	High Similarity	NPC473882
0.9	High Similarity	NPC165439
0.8991	High Similarity	NPC471967
0.8991	High Similarity	NPC477253
0.8981	High Similarity	NPC27551
0.8981	High Similarity	NPC114961
0.8972	High Similarity	NPC295389
0.8972	High Similarity	NPC195708
0.8957	High Similarity	NPC473505
0.8947	High Similarity	NPC475431
0.8929	High Similarity	NPC86020
0.8929	High Similarity	NPC475632
0.8919	High Similarity	NPC279638
0.8919	High Similarity	NPC244127
0.8909	High Similarity	NPC73455
0.8909	High Similarity	NPC62696
0.8909	High Similarity	NPC251309
0.8909	High Similarity	NPC200944
0.8909	High Similarity	NPC293038
0.8899	High Similarity	NPC292196
0.8889	High Similarity	NPC8431
0.886	High Similarity	NPC202051
0.885	High Similarity	NPC197003
0.885	High Similarity	NPC161738
0.885	High Similarity	NPC190939
0.8829	High Similarity	NPC102088
0.8818	High Similarity	NPC233003
0.8814	High Similarity	NPC471407
0.8807	High Similarity	NPC101450
0.8796	High Similarity	NPC272576
0.8793	High Similarity	NPC475194
0.8785	High Similarity	NPC210178
0.8785	High Similarity	NPC162033
0.8785	High Similarity	NPC63023
0.8785	High Similarity	NPC95243
0.8785	High Similarity	NPC242748
0.8772	High Similarity	NPC308459
0.8772	High Similarity	NPC470312
0.8772	High Similarity	NPC475187
0.8739	High Similarity	NPC173347
0.8729	High Similarity	NPC69273
0.8729	High Similarity	NPC311534
0.8729	High Similarity	NPC293623
0.8729	High Similarity	NPC168899
0.8727	High Similarity	NPC274833
0.8727	High Similarity	NPC114188
0.8716	High Similarity	NPC57362
0.8716	High Similarity	NPC237503
0.8716	High Similarity	NPC118225
0.8716	High Similarity	NPC137917
0.8716	High Similarity	NPC306746
0.8716	High Similarity	NPC477070
0.8716	High Similarity	NPC167383
0.8716	High Similarity	NPC477069
0.8716	High Similarity	NPC204407
0.8707	High Similarity	NPC27363
0.8696	High Similarity	NPC182900
0.8696	High Similarity	NPC475182
0.8696	High Similarity	NPC42675
0.8696	High Similarity	NPC476672
0.8696	High Similarity	NPC249553
0.8696	High Similarity	NPC476544
0.8696	High Similarity	NPC476545
0.8696	High Similarity	NPC476543
0.8692	High Similarity	NPC100955
0.8692	High Similarity	NPC121566
0.8692	High Similarity	NPC223741
0.8684	High Similarity	NPC319570
0.8673	High Similarity	NPC477252
0.8667	High Similarity	NPC473200
0.8667	High Similarity	NPC471855
0.8667	High Similarity	NPC7341
0.8661	High Similarity	NPC220293
0.8661	High Similarity	NPC475163
0.8661	High Similarity	NPC116024
0.8649	High Similarity	NPC472719
0.8649	High Similarity	NPC207845
0.8649	High Similarity	NPC243572
0.8644	High Similarity	NPC329784
0.8644	High Similarity	NPC240070
0.8636	High Similarity	NPC78046
0.8636	High Similarity	NPC474589
0.8636	High Similarity	NPC102914
0.8636	High Similarity	NPC163314
0.8636	High Similarity	NPC476885
0.8636	High Similarity	NPC270667
0.8636	High Similarity	NPC476887
0.8636	High Similarity	NPC75747
0.8636	High Similarity	NPC90856
0.8636	High Similarity	NPC164194
0.8636	High Similarity	NPC475296
0.8636	High Similarity	NPC29069
0.8636	High Similarity	NPC476883
0.8636	High Similarity	NPC68419
0.8636	High Similarity	NPC199457
0.8636	High Similarity	NPC279554
0.8636	High Similarity	NPC269095
0.8636	High Similarity	NPC127056
0.8636	High Similarity	NPC476886
0.8636	High Similarity	NPC108709
0.8636	High Similarity	NPC56713
0.8636	High Similarity	NPC220984
0.8636	High Similarity	NPC110139
0.8636	High Similarity	NPC136877
0.8636	High Similarity	NPC7870
0.8636	High Similarity	NPC274507
0.8636	High Similarity	NPC59804
0.8636	High Similarity	NPC476880
0.8636	High Similarity	NPC476884
0.8636	High Similarity	NPC174679
0.8636	High Similarity	NPC476882
0.8636	High Similarity	NPC476881
0.8632	High Similarity	NPC248202
0.8624	High Similarity	NPC476123
0.8624	High Similarity	NPC88744
0.8624	High Similarity	NPC284807
0.8624	High Similarity	NPC258323
0.8624	High Similarity	NPC28198
0.8624	High Similarity	NPC177246
0.8624	High Similarity	NPC295980
0.8621	High Similarity	NPC15918
0.8621	High Similarity	NPC305771
0.8621	High Similarity	NPC169816
0.8621	High Similarity	NPC94072
0.8621	High Similarity	NPC156789
0.8611	High Similarity	NPC473923
0.8611	High Similarity	NPC473476
0.8611	High Similarity	NPC473199
0.8611	High Similarity	NPC26798
0.8609	High Similarity	NPC472257
0.8609	High Similarity	NPC129393
0.8609	High Similarity	NPC476670
0.8596	High Similarity	NPC473828
0.8596	High Similarity	NPC45475
0.8596	High Similarity	NPC473617
0.8585	High Similarity	NPC309425
0.8585	High Similarity	NPC472023
0.8585	High Similarity	NPC129372
0.8585	High Similarity	NPC160734
0.8585	High Similarity	NPC47566
0.8585	High Similarity	NPC88000
0.8585	High Similarity	NPC4831
0.8583	High Similarity	NPC241008
0.8571	High Similarity	NPC56071
0.8571	High Similarity	NPC144068
0.8571	High Similarity	NPC280825
0.8571	High Similarity	NPC234287
0.8571	High Similarity	NPC73986
0.8571	High Similarity	NPC70733
0.8571	High Similarity	NPC102619
0.8559	High Similarity	NPC191763
0.8559	High Similarity	NPC473481
0.8559	High Similarity	NPC297208
0.8559	High Similarity	NPC235841
0.8559	High Similarity	NPC469750
0.8559	High Similarity	NPC250556
0.8559	High Similarity	NPC179434
0.8559	High Similarity	NPC108748
0.8559	High Similarity	NPC30397
0.8559	High Similarity	NPC164419
0.8559	High Similarity	NPC211798
0.8559	High Similarity	NPC31839
0.8559	High Similarity	NPC477073
0.8547	High Similarity	NPC141196
0.8547	High Similarity	NPC476542
0.8547	High Similarity	NPC256983
0.8547	High Similarity	NPC1980
0.8547	High Similarity	NPC238005
0.8547	High Similarity	NPC160084
0.8545	High Similarity	NPC473844
0.8545	High Similarity	NPC240125
0.8545	High Similarity	NPC127853
0.8545	High Similarity	NPC51947
0.8545	High Similarity	NPC91583
0.8534	High Similarity	NPC133506
0.8532	High Similarity	NPC473538

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 NPC260665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1768
0.2-0.3	4047
0.3-0.4	2051
0.4-0.5	537
0.5-0.6	245
0.6-0.7	139
0.7-0.8	128
0.8-0.85	23
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9423	High Similarity	NPD6412	Phase 2
0.8559	High Similarity	NPD7507	Approved
0.8462	Intermediate Similarity	NPD6370	Approved
0.8417	Intermediate Similarity	NPD7736	Approved
0.8378	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8347	Intermediate Similarity	NPD7319	Approved
0.8333	Intermediate Similarity	NPD8293	Discontinued
0.8291	Intermediate Similarity	NPD6054	Approved
0.8291	Intermediate Similarity	NPD8377	Approved
0.8291	Intermediate Similarity	NPD8294	Approved
0.8291	Intermediate Similarity	NPD6059	Approved
0.8276	Intermediate Similarity	NPD7327	Approved
0.8276	Intermediate Similarity	NPD7328	Approved
0.8235	Intermediate Similarity	NPD8328	Phase 3
0.822	Intermediate Similarity	NPD8296	Approved
0.822	Intermediate Similarity	NPD8335	Approved
0.822	Intermediate Similarity	NPD8378	Approved
0.822	Intermediate Similarity	NPD8380	Approved
0.822	Intermediate Similarity	NPD8033	Approved
0.822	Intermediate Similarity	NPD8379	Approved
0.8205	Intermediate Similarity	NPD7516	Approved
0.8158	Intermediate Similarity	NPD8297	Approved
0.8158	Intermediate Similarity	NPD6882	Approved
0.8125	Intermediate Similarity	NPD6686	Approved
0.8087	Intermediate Similarity	NPD8133	Approved
0.8083	Intermediate Similarity	NPD6067	Discontinued
0.8067	Intermediate Similarity	NPD7503	Approved
0.8067	Intermediate Similarity	NPD6015	Approved
0.8067	Intermediate Similarity	NPD6016	Approved
0.8034	Intermediate Similarity	NPD6009	Approved
0.8017	Intermediate Similarity	NPD7492	Approved
0.8	Intermediate Similarity	NPD5988	Approved
0.7983	Intermediate Similarity	NPD6319	Approved
0.7951	Intermediate Similarity	NPD6616	Approved
0.7946	Intermediate Similarity	NPD6675	Approved
0.7946	Intermediate Similarity	NPD6402	Approved
0.7946	Intermediate Similarity	NPD7128	Approved
0.7946	Intermediate Similarity	NPD5739	Approved
0.7931	Intermediate Similarity	NPD4632	Approved
0.7895	Intermediate Similarity	NPD6373	Approved
0.7895	Intermediate Similarity	NPD6372	Approved
0.7886	Intermediate Similarity	NPD7078	Approved
0.7857	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7320	Approved
0.7807	Intermediate Similarity	NPD6899	Approved
0.7807	Intermediate Similarity	NPD6881	Approved
0.7798	Intermediate Similarity	NPD4755	Approved
0.7759	Intermediate Similarity	NPD6649	Approved
0.7759	Intermediate Similarity	NPD6650	Approved
0.7759	Intermediate Similarity	NPD8130	Phase 1
0.7757	Intermediate Similarity	NPD4202	Approved
0.7731	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5701	Approved
0.7719	Intermediate Similarity	NPD5697	Approved
0.768	Intermediate Similarity	NPD6033	Approved
0.7672	Intermediate Similarity	NPD4634	Approved
0.7672	Intermediate Similarity	NPD7102	Approved
0.7672	Intermediate Similarity	NPD6883	Approved
0.7672	Intermediate Similarity	NPD7290	Approved
0.7658	Intermediate Similarity	NPD5285	Approved
0.7658	Intermediate Similarity	NPD5286	Approved
0.7658	Intermediate Similarity	NPD4700	Approved
0.7658	Intermediate Similarity	NPD4696	Approved
0.7642	Intermediate Similarity	NPD5328	Approved
0.7636	Intermediate Similarity	NPD6083	Phase 2
0.7636	Intermediate Similarity	NPD6084	Phase 2
0.7607	Intermediate Similarity	NPD6617	Approved
0.7607	Intermediate Similarity	NPD6869	Approved
0.7607	Intermediate Similarity	NPD6847	Approved
0.7586	Intermediate Similarity	NPD6012	Approved
0.7586	Intermediate Similarity	NPD6014	Approved
0.7586	Intermediate Similarity	NPD6013	Approved
0.7568	Intermediate Similarity	NPD7638	Approved
0.7524	Intermediate Similarity	NPD3618	Phase 1
0.7523	Intermediate Similarity	NPD7748	Approved
0.7522	Intermediate Similarity	NPD5224	Approved
0.7522	Intermediate Similarity	NPD5211	Phase 2
0.7522	Intermediate Similarity	NPD5225	Approved
0.7522	Intermediate Similarity	NPD5226	Approved
0.7522	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.748	Intermediate Similarity	NPD5983	Phase 2
0.7478	Intermediate Similarity	NPD4768	Approved
0.7478	Intermediate Similarity	NPD4767	Approved
0.7478	Intermediate Similarity	NPD6008	Approved
0.7477	Intermediate Similarity	NPD7902	Approved
0.7477	Intermediate Similarity	NPD4753	Phase 2
0.7458	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5175	Approved
0.7456	Intermediate Similarity	NPD5174	Approved
0.7438	Intermediate Similarity	NPD7115	Discovery
0.7434	Intermediate Similarity	NPD5223	Approved
0.7431	Intermediate Similarity	NPD6399	Phase 3
0.7391	Intermediate Similarity	NPD5141	Approved
0.7383	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6336	Discontinued
0.7358	Intermediate Similarity	NPD5330	Approved
0.7358	Intermediate Similarity	NPD7521	Approved
0.7358	Intermediate Similarity	NPD7334	Approved
0.7358	Intermediate Similarity	NPD6684	Approved
0.7358	Intermediate Similarity	NPD6409	Approved
0.7358	Intermediate Similarity	NPD7146	Approved
0.735	Intermediate Similarity	NPD4729	Approved
0.735	Intermediate Similarity	NPD4730	Approved
0.7339	Intermediate Similarity	NPD7515	Phase 2
0.7333	Intermediate Similarity	NPD4786	Approved
0.7304	Intermediate Similarity	NPD4754	Approved
0.7297	Intermediate Similarity	NPD5695	Phase 3
0.7273	Intermediate Similarity	NPD8171	Discontinued
0.7257	Intermediate Similarity	NPD5696	Approved
0.7232	Intermediate Similarity	NPD4697	Phase 3
0.7232	Intermediate Similarity	NPD5221	Approved
0.7232	Intermediate Similarity	NPD5222	Approved
0.7232	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5250	Approved
0.7227	Intermediate Similarity	NPD5247	Approved
0.7227	Intermediate Similarity	NPD5249	Phase 3
0.7227	Intermediate Similarity	NPD5248	Approved
0.7227	Intermediate Similarity	NPD5251	Approved
0.7222	Intermediate Similarity	NPD6903	Approved
0.7213	Intermediate Similarity	NPD6274	Approved
0.7207	Intermediate Similarity	NPD7900	Approved
0.7207	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5128	Approved
0.7182	Intermediate Similarity	NPD8035	Phase 2
0.7182	Intermediate Similarity	NPD8034	Phase 2
0.7177	Intermediate Similarity	NPD7101	Approved
0.7177	Intermediate Similarity	NPD7100	Approved
0.7168	Intermediate Similarity	NPD5173	Approved
0.7154	Intermediate Similarity	NPD5956	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3667	Approved
0.7103	Intermediate Similarity	NPD5329	Approved
0.7097	Intermediate Similarity	NPD6335	Approved
0.7064	Intermediate Similarity	NPD5737	Approved
0.7064	Intermediate Similarity	NPD6672	Approved
0.7063	Intermediate Similarity	NPD8515	Approved
0.7063	Intermediate Similarity	NPD8517	Approved
0.7063	Intermediate Similarity	NPD6909	Approved
0.7063	Intermediate Similarity	NPD8516	Approved
0.7063	Intermediate Similarity	NPD6908	Approved
0.7063	Intermediate Similarity	NPD8513	Phase 3
0.7025	Intermediate Similarity	NPD5217	Approved
0.7025	Intermediate Similarity	NPD5215	Approved
0.7025	Intermediate Similarity	NPD5216	Approved
0.7016	Intermediate Similarity	NPD6317	Approved
0.7009	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.696	Remote Similarity	NPD6314	Approved
0.696	Remote Similarity	NPD6313	Approved
0.6944	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5169	Approved
0.6942	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5135	Approved
0.6923	Remote Similarity	NPD7632	Discontinued
0.6917	Remote Similarity	NPD8449	Approved
0.6885	Remote Similarity	NPD5127	Approved
0.6881	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4689	Approved
0.6881	Remote Similarity	NPD4693	Phase 3
0.6881	Remote Similarity	NPD5279	Phase 3
0.6881	Remote Similarity	NPD4688	Approved
0.6881	Remote Similarity	NPD4138	Approved
0.6881	Remote Similarity	NPD5205	Approved
0.6881	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.687	Remote Similarity	NPD8336	Approved
0.687	Remote Similarity	NPD8337	Approved
0.6866	Remote Similarity	NPD8450	Suspended
0.6829	Remote Similarity	NPD6053	Discontinued
0.68	Remote Similarity	NPD6868	Approved
0.6797	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7525	Registered
0.6791	Remote Similarity	NPD8338	Approved
0.6777	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4522	Approved
0.6759	Remote Similarity	NPD4788	Approved
0.6757	Remote Similarity	NPD5208	Approved
0.6754	Remote Similarity	NPD6001	Approved
0.6727	Remote Similarity	NPD5690	Phase 2
0.6727	Remote Similarity	NPD4694	Approved
0.6727	Remote Similarity	NPD6098	Approved
0.6727	Remote Similarity	NPD5280	Approved
0.6726	Remote Similarity	NPD6050	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