NPASS Compound

Natural Product: NPC284406

Natural Product ID	NPC284406
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Desglucocheirotoxin
IUPAC Name	(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms	Desglucocheirotoxin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1169675
PubChem CID	16401455
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 81 86 0 0 0 0 0 0 0 0999 V2000 -7.3790 -2.2508 -1.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7544 -1.3315 -0.1748 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7836 -0.3618 0.3613 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2376 1.0349 0.1400 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8491 1.0892 0.7406 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9566 -0.0218 0.2263 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6960 -0.6903 -0.7774 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8165 0.4503 -0.3771 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6360 -0.0819 0.1944 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8575 -0.7624 -0.8832 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8687 0.1253 -1.5635 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1087 0.8064 -0.6369 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2091 2.2338 -1.1184 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0525 3.1905 -0.4204 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4573 0.1788 -0.7991 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3007 1.0048 -1.7162 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6531 0.3918 -1.8601 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3595 0.1716 -0.5413 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7710 1.4889 0.0190 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4904 -0.7859 -0.8098 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0875 -2.1384 -0.2302 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6030 -1.9673 -0.0153 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4991 -0.5590 0.4528 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1005 -0.0354 0.5448 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2157 -0.9598 1.3296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1166 -0.3079 1.6241 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3916 0.8834 0.7761 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9108 1.0982 0.7873 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1167 2.0160 1.4347 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0952 -0.4498 1.7030 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8047 -0.3511 -0.2708 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8375 -0.0985 -1.0606 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9493 0.2972 -0.2219 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1197 0.6210 -0.6058 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5418 0.2707 1.0886 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2088 -0.1539 1.1358 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9948 1.0563 2.1258 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0167 1.9643 0.8365 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9378 -0.4848 -0.3869 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4262 -2.5246 -0.9073 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3611 -1.8007 -2.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8071 -3.1994 -1.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3327 -1.9485 0.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9592 -0.5286 1.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1989 1.2444 -0.9453 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3828 2.0646 0.4554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6980 -0.7197 1.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9780 -0.7622 1.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3940 -1.7342 -0.5768 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5852 -1.0760 -1.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4169 0.8618 -2.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3206 -0.5184 -2.3088 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5284 2.4749 -2.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3320 -0.8358 -1.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8195 0.9978 -2.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3568 2.0658 -1.3977 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5942 -0.5693 -2.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3146 1.0628 -2.4619 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1405 2.2885 -0.4763 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5242 1.5698 1.0913 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8166 1.7835 -0.2225 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6031 -0.9901 -1.9115 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5661 -2.2226 0.7774 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3404 -2.9764 -0.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2072 -2.7017 0.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1193 -2.1200 -1.0029 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1616 0.9573 1.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6928 -1.3724 2.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9917 -1.8426 0.6639 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0377 0.0464 2.6952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9572 -1.0408 1.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2329 1.3294 1.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0893 1.9886 0.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4694 2.3005 2.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8545 -1.2508 2.2381 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8859 -0.1627 -2.1375 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6128 0.6154 1.6765 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2151 -1.1203 1.7008 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3087 1.9810 2.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4425 1.5537 1.6275 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5525 0.2499 -0.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 13 14 2 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 1 23 30 1 1 20 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 5 37 1 0 4 38 1 0 3 39 1 0 7 2 1 0 28 9 1 0 36 31 1 0 27 12 1 0 24 15 1 0 23 18 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 1 3 44 1 1 4 45 1 6 5 46 1 1 6 47 1 1 9 48 1 1 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 13 53 1 0 15 54 1 6 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 19 59 1 0 19 60 1 0 19 61 1 0 20 62 1 6 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 24 67 1 1 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 29 74 1 0 30 75 1 0 32 76 1 0 36 77 1 0 36 78 1 0 37 79 1 0 38 80 1 0 39 81 1 0 M END

Standard InCHIKey	HULMNSIAKWANQO-PZXOABCJSA-N
Standard InCHI	InChI=1S/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17+,18-,19+,20-,22+,23-,24-,25+,26-,27+,28+,29+/m1/s1
SMILES	C[C@@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@]2(C=O)[C@H]3CC[C@]4(C)[C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)C1=CC(=O)OC1)O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	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	Organism Name	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
Activity	4
Ratio	2
Inhibition	1
ED50	10

Activity Type	# Activity
Cell line	7
Non-molecular	10

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	=	0.015	ug ml-1	PMID[19651910]
NPT308	Cell line	CAKI-1	Homo sapiens	ED50	=	0.014	ug ml-1	PMID[19651910]
NPT309	Cell line	1A9	Homo sapiens	ED50	=	0.012	ug ml-1	PMID[19651910]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	0.018	ug ml-1	PMID[19651915]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	0.015	ug ml-1	PMID[19651910]
NPT81	Cell line	A549	Homo sapiens	ED50	=	0.0092	ug ml-1	PMID[19651910]
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.044	ug ml-1	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.05	uM	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.5	uM	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	300.0	%	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Ratio	=	50.0	n.a.	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Ratio	=	10.0	n.a.	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	76.9	%	PMID[24033101]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.044	ug ml-1	PMID[24582402]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.054	ug ml-1	PMID[24582402]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.018	ug ml-1	PMID[24582402]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC284406 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	15723
0.1-0.2	28744
0.2-0.3	4828
0.3-0.4	344
0.4-0.5	70
0.5-0.6	71
0.6-0.7	33
0.7-0.8	0
0.8-0.85	13
0.85-0.9	4
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC17896
1.0	High Similarity	NPC469755
1.0	High Similarity	NPC197707
1.0	High Similarity	NPC251866
0.863	High Similarity	NPC99728
0.863	High Similarity	NPC87250
0.863	High Similarity	NPC244402
0.863	High Similarity	NPC50305
0.84	Intermediate Similarity	NPC157376
0.84	Intermediate Similarity	NPC142066
0.84	Intermediate Similarity	NPC603972
0.8267	Intermediate Similarity	NPC219085
0.8077	Intermediate Similarity	NPC9499
0.8077	Intermediate Similarity	NPC471360
0.8077	Intermediate Similarity	NPC469751
0.8077	Intermediate Similarity	NPC471361
0.8077	Intermediate Similarity	NPC86159
0.8077	Intermediate Similarity	NPC469752
0.8077	Intermediate Similarity	NPC469754
0.8077	Intermediate Similarity	NPC70542
0.8072	Intermediate Similarity	NPC469749
0.7927	Intermediate Similarity	NPC32793
0.7927	Intermediate Similarity	NPC116075
0.7692	Intermediate Similarity	NPC469750
0.7595	Intermediate Similarity	NPC10823
0.7564	Intermediate Similarity	NPC84987
0.7564	Intermediate Similarity	NPC309034
0.7436	Intermediate Similarity	NPC99620
0.7356	Intermediate Similarity	NPC146857
0.7356	Intermediate Similarity	NPC247190
0.7284	Intermediate Similarity	NPC77319
0.7284	Intermediate Similarity	NPC471351
0.7284	Intermediate Similarity	NPC180079
0.7284	Intermediate Similarity	NPC471355
0.725	Intermediate Similarity	NPC6108
0.725	Intermediate Similarity	NPC89514
0.716	Intermediate Similarity	NPC76572
0.716	Intermediate Similarity	NPC193382
0.7093	Intermediate Similarity	NPC608063
0.7089	Intermediate Similarity	NPC158344
0.6905	Remote Similarity	NPC471354
0.6905	Remote Similarity	NPC27507
0.6875	Remote Similarity	NPC474418
0.6829	Remote Similarity	NPC480915
0.6809	Remote Similarity	NPC329675
0.6809	Remote Similarity	NPC194716
0.6747	Remote Similarity	NPC480914
0.6742	Remote Similarity	NPC59288
0.6707	Remote Similarity	NPC196429
0.6629	Remote Similarity	NPC475629
0.6627	Remote Similarity	NPC5311
0.6517	Remote Similarity	NPC475556
0.6517	Remote Similarity	NPC240070
0.6517	Remote Similarity	NPC311706
0.6471	Remote Similarity	NPC83287
0.6429	Remote Similarity	NPC77299
0.6429	Remote Similarity	NPC480906
0.6395	Remote Similarity	NPC471359
0.6395	Remote Similarity	NPC179412
0.6395	Remote Similarity	NPC471356
0.6316	Remote Similarity	NPC329636
0.6316	Remote Similarity	NPC72772
0.6235	Remote Similarity	NPC34390
0.6154	Remote Similarity	NPC188234
0.6136	Remote Similarity	NPC469753
0.6118	Remote Similarity	NPC484211
0.6111	Remote Similarity	NPC30483
0.6111	Remote Similarity	NPC470897
0.6067	Remote Similarity	NPC480907
0.6044	Remote Similarity	NPC236973
0.6044	Remote Similarity	NPC27363
0.6023	Remote Similarity	NPC471353
0.6	Remote Similarity	NPC471633
0.5957	Remote Similarity	NPC232785
0.5957	Remote Similarity	NPC486139
0.5914	Remote Similarity	NPC264336
0.5909	Remote Similarity	NPC250556
0.587	Remote Similarity	NPC32177
0.587	Remote Similarity	NPC292467
0.587	Remote Similarity	NPC469756
0.587	Remote Similarity	NPC275901
0.5851	Remote Similarity	NPC486143
0.5851	Remote Similarity	NPC125077
0.5851	Remote Similarity	NPC486142
0.5851	Remote Similarity	NPC486149
0.5833	Remote Similarity	NPC486138
0.5833	Remote Similarity	NPC276838
0.5806	Remote Similarity	NPC480910
0.5806	Remote Similarity	NPC480909
0.5795	Remote Similarity	NPC199428
0.5795	Remote Similarity	NPC243196
0.5795	Remote Similarity	NPC109448
0.5795	Remote Similarity	NPC310341
0.573	Remote Similarity	NPC146456
0.5729	Remote Similarity	NPC329986
0.5729	Remote Similarity	NPC140092
0.5729	Remote Similarity	NPC486146
0.5714	Remote Similarity	NPC72260
0.5684	Remote Similarity	NPC486135
0.5684	Remote Similarity	NPC486137
0.5618	Remote Similarity	NPC604978
0.5579	Remote Similarity	NPC610296
0.5556	Remote Similarity	NPC484212
0.5513	Remote Similarity	NPC97487
0.5506	Remote Similarity	NPC484210
0.55	Remote Similarity	NPC486144
0.55	Remote Similarity	NPC486145
0.55	Remote Similarity	NPC486147
0.55	Remote Similarity	NPC486148
0.5495	Remote Similarity	NPC93883
0.5495	Remote Similarity	NPC305574
0.5444	Remote Similarity	NPC84949
0.5444	Remote Similarity	NPC480562
0.5444	Remote Similarity	NPC74945
0.5444	Remote Similarity	NPC31354
0.5444	Remote Similarity	NPC69576
0.5437	Remote Similarity	NPC486150
0.5417	Remote Similarity	NPC486127
0.5375	Remote Similarity	NPC10232
0.5368	Remote Similarity	NPC62172
0.5347	Remote Similarity	NPC475590
0.5347	Remote Similarity	NPC486136
0.534	Remote Similarity	NPC486134
0.534	Remote Similarity	NPC486141
0.5333	Remote Similarity	NPC486126
0.5312	Remote Similarity	NPC471357
0.5312	Remote Similarity	NPC469757
0.5312	Remote Similarity	NPC75616
0.5312	Remote Similarity	NPC117702
0.5312	Remote Similarity	NPC486130
0.5281	Remote Similarity	NPC473852
0.5243	Remote Similarity	NPC120390
0.5243	Remote Similarity	NPC74259
0.5243	Remote Similarity	NPC475419
0.5222	Remote Similarity	NPC486129
0.5217	Remote Similarity	NPC88668
0.5192	Remote Similarity	NPC474908
0.5161	Remote Similarity	NPC483822
0.5161	Remote Similarity	NPC484202
0.5161	Remote Similarity	NPC277374
0.5098	Remote Similarity	NPC486128
0.5093	Remote Similarity	NPC286809
0.5051	Remote Similarity	NPC55532
0.5047	Remote Similarity	NPC474423

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC284406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6152
0.1-0.2	2856
0.2-0.3	123
0.3-0.4	6
0.4-0.5	6
0.5-0.6	4
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD7327	Approved
0.6471	Remote Similarity	NPD7328	Phase 4
0.5909	Remote Similarity	NPD7507	Pre-clinical
0.5714	Remote Similarity	NPD8294	Phase 4
0.5161	Remote Similarity	NPD7516	Pre-clinical
0.5051	Remote Similarity	NPD8377	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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