NPASS Compound

Structure

CID290746 OpenBabel06191716102D 75 82 0 0 1 0 0 0 0 0999 V2000 1.4866 10.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0218 8.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4155 9.9347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8972 -11.4288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1017 0.4111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2426 -6.1780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7563 -4.8397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2203 9.7228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7120 4.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0448 6.8957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3009 -11.6867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4731 -2.8323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6678 -9.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8400 -5.0976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3572 4.4259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1278 2.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9199 3.3967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1493 5.4041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9903 8.3093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5781 7.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1197 8.2874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8220 2.7786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6678 -9.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7515 -0.5159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3894 -7.1050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4731 -2.8323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5040 5.3530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2787 9.5746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3276 9.2656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1541 -10.7597 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1506 0.1021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2915 -6.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0132 -4.1706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6325 8.9138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6141 3.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0788 2.1095 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4599 -10.3996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0084 -1.1850 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1326 -7.7742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6810 -3.8105 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4551 5.0440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2961 6.3311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8628 7.6183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5436 0.4622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6189 -9.1124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4779 -2.5233 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5973 -6.1269 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2030 -11.0687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0573 -0.8760 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0836 -7.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0621 -4.4796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6630 4.0658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0393 7.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0393 8.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1982 5.7131 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9903 6.6912 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3620 9.0183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8139 7.9273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9951 -12.0469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0448 8.1048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9414 6.3822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7335 6.0221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5088 -10.7086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2163 -2.1632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9247 -8.7523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 -4.1195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3620 -9.7815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5925 0.7713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5484 -5.8179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2211 -3.1924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2867 1.1314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6549 6.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8268 -8.1343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6858 -1.5452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1458 -5.4577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 8 34 1 0 0 0 0 10 53 1 0 0 0 0 11 63 1 0 0 0 0 12 64 1 0 0 0 0 13 65 1 0 0 0 0 14 66 1 0 0 0 0 15 18 1 0 0 0 0 15 35 2 0 0 0 0 16 17 1 0 0 0 0 16 36 1 0 0 0 0 17 52 1 0 0 0 0 18 55 1 0 0 0 0 19 20 1 0 0 0 0 19 54 1 0 0 0 0 20 56 1 0 0 0 0 21 29 2 0 0 0 0 21 43 1 0 0 0 0 22 35 1 0 0 0 0 22 36 1 0 0 0 0 23 37 1 0 0 0 0 23 45 1 0 0 0 0 24 38 1 0 0 0 0 24 44 1 0 0 0 0 25 39 1 0 0 0 0 25 47 1 0 0 0 0 26 40 1 0 0 0 0 26 46 1 0 0 0 0 27 41 1 0 0 0 0 27 42 1 0 0 0 0 28 29 1 0 0 0 0 30 4 1 1 0 0 0 30 48 1 0 0 0 0 30 67 1 0 0 0 0 31 5 1 6 0 0 0 31 49 1 0 0 0 0 31 68 1 0 0 0 0 32 6 1 6 0 0 0 32 50 1 0 0 0 0 32 69 1 0 0 0 0 33 7 1 1 0 0 0 33 51 1 0 0 0 0 33 70 1 0 0 0 0 34 54 1 0 0 0 0 34 57 2 0 0 0 0 35 52 1 0 0 0 0 36 71 1 6 0 0 0 37 48 1 0 0 0 0 37 63 1 6 0 0 0 38 49 1 0 0 0 0 38 64 1 1 0 0 0 39 50 1 0 0 0 0 39 65 1 1 0 0 0 40 51 1 0 0 0 0 40 66 1 1 0 0 0 41 52 1 6 0 0 0 41 55 1 0 0 0 0 42 53 1 6 0 0 0 42 72 1 0 0 0 0 43 58 2 0 0 0 0 43 72 1 0 0 0 0 44 68 1 0 0 0 0 44 71 1 6 0 0 0 45 67 1 0 0 0 0 45 73 1 6 0 0 0 46 70 1 0 0 0 0 46 74 1 6 0 0 0 47 69 1 0 0 0 0 47 75 1 6 0 0 0 48 59 1 6 0 0 0 49 74 1 1 0 0 0 50 73 1 1 0 0 0 51 75 1 1 0 0 0 52 9 1 6 0 0 0 53 54 1 1 0 0 0 54 60 1 1 0 0 0 55 56 1 1 0 0 0 55 61 1 0 0 0 0 56 53 1 6 0 0 0 56 62 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1066.61
Volume:	1065.148
LogP:	4.48
LogD:	3.443
LogS:	-5.101
# Rotatable Bonds:	17
TPSA:	235.05
# H-Bond Aceptor:	19
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	6.968
Fsp3:	0.893
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:	-5.129
MDCK Permeability:	0.00019106529362034053
Pgp-inhibitor:	0.445
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	80.26729583740234%
Volume Distribution (VD):	0.587
Pgp-substrate:	7.97556209564209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.991
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.595
CYP3A4-substrate:	0.947

ADMET: Excretion

Clearance (CL):	2.542
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.848
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.473
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.924
Carcinogencity:	0.828
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC290746

Natural Product ID:	NPC290746
*Common Name:**	Wilfoside C1N
IUPAC Name:	[(3S,8S,9R,10R,12R,13S,14R,17R)-17-acetyl-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6S)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (E)-3,4-dimethylpent-2-enoate
Synonyms:
Standard InCHIKey:	YUDOHRCAEPBFBO-ZNQKHRBLSA-N
Standard InCHI:	InChI=1S/C56H90O19/c1-28(2)29(3)21-43(58)72-42-27-41-52(9)17-16-36(22-35(52)15-18-55(41,61)56(62)20-19-54(60,34(8)57)53(42,56)10)71-44-24-38(64-12)49(31(5)68-44)74-46-26-40(66-14)51(33(7)70-46)75-47-25-39(65-13)50(32(6)69-47)73-45-23-37(63-11)48(59)30(4)67-45/h15,21,28,30-33,36-42,44-51,59-62H,16-20,22-27H2,1-14H3/b29-21+/t30-,31+,32+,33-,36-,37+,38-,39-,40-,41+,42+,44-,45-,46-,47-,48-,49+,50+,51+,52-,53+,54-,55-,56+/m0/s1
SMILES:	CC(C)/C(=C/C(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@@H](CC3=CC[C@]2([C@]2(CC[C@](C(=O)C)([C@@]12C)O)O)O)O[C@H]1C[C@@H]([C@@H]([C@@H](C)O1)O[C@H]1C[C@@H]([C@@H]([C@H](C)O1)O[C@H]1C[C@@H]([C@@H]([C@@H](C)O1)O[C@H]1C[C@H]([C@H]([C@H](C)O1)O)OC)OC)OC)OC)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2228801
PubChem CID:	76318706
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
NPO8809	Cynanchum wilfordii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217732]
NPO8809	Cynanchum wilfordii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26716755]
NPO8809	Cynanchum wilfordii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8809	Cynanchum wilfordii	Species	Apocynaceae	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	2

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3519	Organism	Blumeria graminis f. sp. hordei	Blumeria graminis f. sp. hordei	IC50	=	3.24	ug.mL-1	PMID[494610]
NPT3519	Organism	Blumeria graminis f. sp. hordei	Blumeria graminis f. sp. hordei	Activity	=	95.0	%	PMID[494610]
NPT3519	Organism	Blumeria graminis f. sp. hordei	Blumeria graminis f. sp. hordei	Activity	>	77.0	%	PMID[494610]

☑ 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 NPC290746 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	342
0.1-0.2	1899
0.2-0.3	5141
0.3-0.4	8637
0.4-0.5	11353
0.5-0.6	7547
0.6-0.7	4737
0.7-0.8	1940
0.8-0.85	756
0.85-0.9	300
0.9-0.95	35
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC79250
0.9524	High Similarity	NPC473805
0.9524	High Similarity	NPC473519
0.9449	High Similarity	NPC102015
0.9219	High Similarity	NPC471855
0.9062	High Similarity	NPC471407
0.8992	High Similarity	NPC173347
0.8855	High Similarity	NPC104585
0.8855	High Similarity	NPC477709
0.8855	High Similarity	NPC476221
0.8855	High Similarity	NPC142756
0.8855	High Similarity	NPC298783
0.8855	High Similarity	NPC225385
0.8855	High Similarity	NPC157817
0.8846	High Similarity	NPC477493
0.8797	High Similarity	NPC329675
0.8797	High Similarity	NPC59288
0.8779	High Similarity	NPC93416
0.876	High Similarity	NPC329784
0.876	High Similarity	NPC470780
0.876	High Similarity	NPC240070
0.874	High Similarity	NPC28532
0.8731	High Similarity	NPC596
0.873	High Similarity	NPC471406
0.8722	High Similarity	NPC194716
0.8722	High Similarity	NPC262813
0.8712	High Similarity	NPC475487
0.8702	High Similarity	NPC241008
0.8702	High Similarity	NPC159338
0.8702	High Similarity	NPC16569
0.8702	High Similarity	NPC253456
0.8692	High Similarity	NPC114306
0.8692	High Similarity	NPC477490
0.8692	High Similarity	NPC311534
0.8657	High Similarity	NPC251998
0.8657	High Similarity	NPC471089
0.8657	High Similarity	NPC141215
0.8657	High Similarity	NPC190065
0.8647	High Similarity	NPC329636
0.8636	High Similarity	NPC277212
0.8636	High Similarity	NPC473918
0.8636	High Similarity	NPC42670
0.8636	High Similarity	NPC178264
0.8636	High Similarity	NPC19124
0.8636	High Similarity	NPC192765
0.8636	High Similarity	NPC46823
0.8636	High Similarity	NPC30279
0.8636	High Similarity	NPC476776
0.8636	High Similarity	NPC71391
0.8626	High Similarity	NPC140092
0.8626	High Similarity	NPC329986
0.8626	High Similarity	NPC476966
0.8626	High Similarity	NPC470912
0.8626	High Similarity	NPC91
0.8626	High Similarity	NPC188234
0.8626	High Similarity	NPC276838
0.8626	High Similarity	NPC125077
0.8626	High Similarity	NPC232785
0.8605	High Similarity	NPC248202
0.8605	High Similarity	NPC473505
0.8593	High Similarity	NPC295885
0.8593	High Similarity	NPC140045
0.8583	High Similarity	NPC473566
0.8583	High Similarity	NPC475358
0.8583	High Similarity	NPC129393
0.8582	High Similarity	NPC171619
0.8571	High Similarity	NPC116075
0.8571	High Similarity	NPC32793
0.8571	High Similarity	NPC478151
0.8571	High Similarity	NPC469749
0.8571	High Similarity	NPC247190
0.8571	High Similarity	NPC146857
0.8571	High Similarity	NPC225791
0.8561	High Similarity	NPC172374
0.8561	High Similarity	NPC476775
0.8561	High Similarity	NPC478065
0.8561	High Similarity	NPC173435
0.8561	High Similarity	NPC264566
0.8561	High Similarity	NPC301639
0.8561	High Similarity	NPC475167
0.8561	High Similarity	NPC478064
0.8561	High Similarity	NPC476074
0.8561	High Similarity	NPC134914
0.8561	High Similarity	NPC213634
0.8561	High Similarity	NPC476774
0.8561	High Similarity	NPC271610
0.8561	High Similarity	NPC477197
0.8561	High Similarity	NPC262796
0.8561	High Similarity	NPC476780
0.8561	High Similarity	NPC475377
0.8561	High Similarity	NPC45346
0.8561	High Similarity	NPC329993
0.855	High Similarity	NPC69273
0.855	High Similarity	NPC470475
0.855	High Similarity	NPC477078
0.855	High Similarity	NPC475281
0.855	High Similarity	NPC329923
0.855	High Similarity	NPC477075
0.855	High Similarity	NPC293623
0.855	High Similarity	NPC470476
0.855	High Similarity	NPC168899
0.8527	High Similarity	NPC27363
0.8527	High Similarity	NPC160084
0.8527	High Similarity	NPC208193
0.8527	High Similarity	NPC117445
0.8527	High Similarity	NPC256983
0.8527	High Similarity	NPC308262
0.8519	High Similarity	NPC127656
0.8516	High Similarity	NPC182900
0.8516	High Similarity	NPC475182
0.8516	High Similarity	NPC249553
0.8507	High Similarity	NPC476777
0.8507	High Similarity	NPC476778
0.8504	High Similarity	NPC190939
0.8504	High Similarity	NPC197003
0.8496	Intermediate Similarity	NPC478150
0.8496	Intermediate Similarity	NPC312650
0.8496	Intermediate Similarity	NPC478153
0.8496	Intermediate Similarity	NPC478152
0.8496	Intermediate Similarity	NPC478154
0.8492	Intermediate Similarity	NPC309433
0.8485	Intermediate Similarity	NPC11577
0.8485	Intermediate Similarity	NPC244296
0.8485	Intermediate Similarity	NPC252289
0.8485	Intermediate Similarity	NPC477079
0.8485	Intermediate Similarity	NPC477077
0.8485	Intermediate Similarity	NPC273878
0.8485	Intermediate Similarity	NPC472267
0.8485	Intermediate Similarity	NPC88311
0.8485	Intermediate Similarity	NPC9470
0.8485	Intermediate Similarity	NPC97918
0.8485	Intermediate Similarity	NPC82380
0.8485	Intermediate Similarity	NPC265841
0.8485	Intermediate Similarity	NPC107536
0.8485	Intermediate Similarity	NPC141600
0.8485	Intermediate Similarity	NPC47995
0.8485	Intermediate Similarity	NPC305793
0.8485	Intermediate Similarity	NPC269484
0.8485	Intermediate Similarity	NPC477076
0.8485	Intermediate Similarity	NPC477196
0.8485	Intermediate Similarity	NPC280029
0.8485	Intermediate Similarity	NPC115656
0.8485	Intermediate Similarity	NPC470518
0.8485	Intermediate Similarity	NPC1314
0.8485	Intermediate Similarity	NPC470913
0.8485	Intermediate Similarity	NPC252657
0.8473	Intermediate Similarity	NPC179412
0.8473	Intermediate Similarity	NPC117702
0.8473	Intermediate Similarity	NPC471357
0.8473	Intermediate Similarity	NPC146456
0.8473	Intermediate Similarity	NPC469757
0.8473	Intermediate Similarity	NPC470516
0.8473	Intermediate Similarity	NPC471356
0.8462	Intermediate Similarity	NPC473474
0.8462	Intermediate Similarity	NPC130229
0.8462	Intermediate Similarity	NPC318135
0.845	Intermediate Similarity	NPC15918
0.845	Intermediate Similarity	NPC156789
0.845	Intermediate Similarity	NPC222688
0.845	Intermediate Similarity	NPC74259
0.845	Intermediate Similarity	NPC193893
0.845	Intermediate Similarity	NPC305771
0.845	Intermediate Similarity	NPC474423
0.845	Intermediate Similarity	NPC264336
0.845	Intermediate Similarity	NPC169816
0.845	Intermediate Similarity	NPC94072
0.8444	Intermediate Similarity	NPC279915
0.8444	Intermediate Similarity	NPC158350
0.8444	Intermediate Similarity	NPC110700
0.8438	Intermediate Similarity	NPC107607
0.8433	Intermediate Similarity	NPC476779
0.8433	Intermediate Similarity	NPC316915
0.8421	Intermediate Similarity	NPC25998
0.8421	Intermediate Similarity	NPC478155
0.8413	Intermediate Similarity	NPC279638
0.8409	Intermediate Similarity	NPC477191
0.8409	Intermediate Similarity	NPC477194
0.8409	Intermediate Similarity	NPC220838
0.8409	Intermediate Similarity	NPC245094
0.8409	Intermediate Similarity	NPC477193
0.8409	Intermediate Similarity	NPC45606
0.8409	Intermediate Similarity	NPC270109
0.8409	Intermediate Similarity	NPC477192
0.84	Intermediate Similarity	NPC165234
0.84	Intermediate Similarity	NPC475536
0.8397	Intermediate Similarity	NPC181066
0.8397	Intermediate Similarity	NPC469947
0.8397	Intermediate Similarity	NPC469750
0.8397	Intermediate Similarity	NPC174367
0.8397	Intermediate Similarity	NPC47113
0.8397	Intermediate Similarity	NPC250556
0.8394	Intermediate Similarity	NPC477232
0.8394	Intermediate Similarity	NPC477233
0.8382	Intermediate Similarity	NPC477236
0.8372	Intermediate Similarity	NPC476543
0.8372	Intermediate Similarity	NPC476544
0.8372	Intermediate Similarity	NPC120390
0.8372	Intermediate Similarity	NPC475590
0.8372	Intermediate Similarity	NPC202051
0.8372	Intermediate Similarity	NPC475419

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 NPC290746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	2067
0.2-0.3	3927
0.3-0.4	1827
0.4-0.5	534
0.5-0.6	288
0.6-0.7	127
0.7-0.8	57
0.8-0.85	7
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8397	Intermediate Similarity	NPD7507	Approved
0.8372	Intermediate Similarity	NPD8335	Approved
0.8372	Intermediate Similarity	NPD8378	Approved
0.8372	Intermediate Similarity	NPD8379	Approved
0.8372	Intermediate Similarity	NPD8033	Approved
0.8372	Intermediate Similarity	NPD8380	Approved
0.8372	Intermediate Similarity	NPD8296	Approved
0.8346	Intermediate Similarity	NPD7319	Approved
0.8295	Intermediate Similarity	NPD8377	Approved
0.8295	Intermediate Similarity	NPD8294	Approved
0.8244	Intermediate Similarity	NPD8328	Phase 3
0.8217	Intermediate Similarity	NPD7516	Approved
0.814	Intermediate Similarity	NPD7327	Approved
0.814	Intermediate Similarity	NPD7328	Approved
0.811	Intermediate Similarity	NPD8133	Approved
0.8	Intermediate Similarity	NPD7736	Approved
0.7926	Intermediate Similarity	NPD8293	Discontinued
0.782	Intermediate Similarity	NPD8515	Approved
0.782	Intermediate Similarity	NPD8517	Approved
0.782	Intermediate Similarity	NPD7503	Approved
0.782	Intermediate Similarity	NPD8516	Approved
0.7786	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6412	Phase 2
0.7761	Intermediate Similarity	NPD6370	Approved
0.7752	Intermediate Similarity	NPD6882	Approved
0.7752	Intermediate Similarity	NPD8297	Approved
0.7687	Intermediate Similarity	NPD8513	Phase 3
0.7656	Intermediate Similarity	NPD6373	Approved
0.7656	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD6372	Approved
0.7652	Intermediate Similarity	NPD6009	Approved
0.7647	Intermediate Similarity	NPD7492	Approved
0.7612	Intermediate Similarity	NPD6059	Approved
0.7612	Intermediate Similarity	NPD6054	Approved
0.7612	Intermediate Similarity	NPD6319	Approved
0.7591	Intermediate Similarity	NPD6616	Approved
0.7578	Intermediate Similarity	NPD6686	Approved
0.7559	Intermediate Similarity	NPD7128	Approved
0.7559	Intermediate Similarity	NPD5739	Approved
0.7559	Intermediate Similarity	NPD6675	Approved
0.7559	Intermediate Similarity	NPD6402	Approved
0.7557	Intermediate Similarity	NPD4632	Approved
0.7538	Intermediate Similarity	NPD6649	Approved
0.7538	Intermediate Similarity	NPD6650	Approved
0.7536	Intermediate Similarity	NPD7078	Approved
0.7442	Intermediate Similarity	NPD6899	Approved
0.7442	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7320	Approved
0.7442	Intermediate Similarity	NPD6881	Approved
0.7426	Intermediate Similarity	NPD6016	Approved
0.7426	Intermediate Similarity	NPD6015	Approved
0.7405	Intermediate Similarity	NPD8130	Phase 1
0.7405	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD7115	Discovery
0.7372	Intermediate Similarity	NPD5988	Approved
0.7364	Intermediate Similarity	NPD5697	Approved
0.7364	Intermediate Similarity	NPD5701	Approved
0.7328	Intermediate Similarity	NPD7102	Approved
0.7328	Intermediate Similarity	NPD7290	Approved
0.7328	Intermediate Similarity	NPD6883	Approved
0.7273	Intermediate Similarity	NPD6617	Approved
0.7273	Intermediate Similarity	NPD6869	Approved
0.7273	Intermediate Similarity	NPD6847	Approved
0.7252	Intermediate Similarity	NPD6013	Approved
0.7252	Intermediate Similarity	NPD6012	Approved
0.7252	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6014	Approved
0.7209	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7604	Phase 2
0.7176	Intermediate Similarity	NPD6011	Approved
0.7174	Intermediate Similarity	NPD5983	Phase 2
0.7154	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6033	Approved
0.7092	Intermediate Similarity	NPD6336	Discontinued
0.709	Intermediate Similarity	NPD6053	Discontinued
0.7087	Intermediate Similarity	NPD7638	Approved
0.7068	Intermediate Similarity	NPD4634	Approved
0.7054	Intermediate Similarity	NPD5211	Phase 2
0.7031	Intermediate Similarity	NPD4696	Approved
0.7031	Intermediate Similarity	NPD7640	Approved
0.7031	Intermediate Similarity	NPD5286	Approved
0.7031	Intermediate Similarity	NPD7639	Approved
0.7031	Intermediate Similarity	NPD4700	Approved
0.7031	Intermediate Similarity	NPD5285	Approved
0.7008	Intermediate Similarity	NPD6083	Phase 2
0.7008	Intermediate Similarity	NPD6084	Phase 2
0.697	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5141	Approved
0.6934	Remote Similarity	NPD6274	Approved
0.6929	Remote Similarity	NPD6921	Approved
0.6923	Remote Similarity	NPD4633	Approved
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD5224	Approved
0.6906	Remote Similarity	NPD7100	Approved
0.6906	Remote Similarity	NPD7101	Approved
0.6894	Remote Similarity	NPD4768	Approved
0.6894	Remote Similarity	NPD4767	Approved
0.687	Remote Similarity	NPD5175	Approved
0.687	Remote Similarity	NPD5174	Approved
0.6846	Remote Similarity	NPD5223	Approved
0.6835	Remote Similarity	NPD6335	Approved
0.6831	Remote Similarity	NPD6067	Discontinued
0.6822	Remote Similarity	NPD5696	Approved
0.6809	Remote Similarity	NPD6909	Approved
0.6809	Remote Similarity	NPD6908	Approved
0.6806	Remote Similarity	NPD8074	Phase 3
0.6791	Remote Similarity	NPD4729	Approved
0.6791	Remote Similarity	NPD4730	Approved
0.6774	Remote Similarity	NPD7625	Phase 1
0.6763	Remote Similarity	NPD6317	Approved
0.6746	Remote Similarity	NPD7799	Discontinued
0.6744	Remote Similarity	NPD7902	Approved
0.6742	Remote Similarity	NPD4754	Approved
0.6735	Remote Similarity	NPD7260	Phase 2
0.6719	Remote Similarity	NPD5695	Phase 3
0.6716	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6313	Approved
0.6714	Remote Similarity	NPD6314	Approved
0.6693	Remote Similarity	NPD6399	Phase 3
0.6691	Remote Similarity	NPD5248	Approved
0.6691	Remote Similarity	NPD5249	Phase 3
0.6691	Remote Similarity	NPD5247	Approved
0.6691	Remote Similarity	NPD5250	Approved
0.6691	Remote Similarity	NPD5251	Approved
0.669	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6641	Remote Similarity	NPD7748	Approved
0.6614	Remote Similarity	NPD5693	Phase 1
0.6587	Remote Similarity	NPD5328	Approved
0.6587	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD6371	Approved
0.6565	Remote Similarity	NPD4225	Approved
0.6562	Remote Similarity	NPD4202	Approved
0.6541	Remote Similarity	NPD7632	Discontinued
0.6538	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5222	Approved
0.6538	Remote Similarity	NPD5221	Approved
0.6533	Remote Similarity	NPD8450	Suspended
0.6522	Remote Similarity	NPD5216	Approved
0.6522	Remote Similarity	NPD5215	Approved
0.6522	Remote Similarity	NPD5217	Approved
0.6512	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7900	Approved
0.6489	Remote Similarity	NPD5173	Approved
0.6484	Remote Similarity	NPD7515	Phase 2
0.6484	Remote Similarity	NPD6079	Approved
0.6467	Remote Similarity	NPD8338	Approved
0.6467	Remote Similarity	NPD6845	Suspended
0.6467	Remote Similarity	NPD8449	Approved
0.6466	Remote Similarity	NPD5344	Discontinued
0.6462	Remote Similarity	NPD4629	Approved
0.6462	Remote Similarity	NPD5210	Approved
0.6462	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6673	Approved
0.6457	Remote Similarity	NPD6080	Approved
0.6457	Remote Similarity	NPD6904	Approved
0.6454	Remote Similarity	NPD6868	Approved
0.6449	Remote Similarity	NPD5135	Approved
0.6449	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5169	Approved
0.6443	Remote Similarity	NPD5956	Approved
0.6439	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8171	Discontinued
0.6406	Remote Similarity	NPD46	Approved
0.6406	Remote Similarity	NPD6698	Approved
0.6403	Remote Similarity	NPD5127	Approved
0.6378	Remote Similarity	NPD6672	Approved
0.6378	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5737	Approved
0.6375	Remote Similarity	NPD7236	Approved
0.6357	Remote Similarity	NPD8034	Phase 2
0.6357	Remote Similarity	NPD8035	Phase 2
0.6349	Remote Similarity	NPD7334	Approved
0.6349	Remote Similarity	NPD7146	Approved
0.6349	Remote Similarity	NPD5330	Approved
0.6349	Remote Similarity	NPD6409	Approved
0.6349	Remote Similarity	NPD7521	Approved
0.6349	Remote Similarity	NPD6684	Approved
0.6349	Remote Similarity	NPD3618	Phase 1
0.6322	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD8336	Approved
0.6309	Remote Similarity	NPD8337	Approved
0.6307	Remote Similarity	NPD8368	Discontinued
0.6292	Remote Similarity	NPD8407	Phase 2
0.628	Remote Similarity	NPD7239	Suspended
0.627	Remote Similarity	NPD5329	Approved
0.6268	Remote Similarity	NPD5167	Approved
0.625	Remote Similarity	NPD6903	Approved
0.6242	Remote Similarity	NPD8448	Approved
0.6231	Remote Similarity	NPD5284	Approved
0.6231	Remote Similarity	NPD6050	Approved
0.6231	Remote Similarity	NPD5281	Approved
0.6225	Remote Similarity	NPD8392	Approved
0.6225	Remote Similarity	NPD8391	Approved
0.6225	Remote Similarity	NPD8390	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