NPASS Compound

Natural Product: NPC260365

Natural Product ID	NPC260365
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MKAWBADWUNBVAW-PGJQYQLYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 84 89 0 0 0 0 0 0 0 0999 V2000 7.2344 -2.8824 0.4774 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4451 -1.6718 0.0603 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3562 -0.6062 -0.5064 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5552 0.6414 -0.8044 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7400 0.9968 0.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8486 -0.2240 0.6855 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7215 -1.2331 1.1447 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8954 0.0202 1.6507 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6317 -0.1139 1.1388 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8132 -1.1098 1.9018 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4471 -1.2918 1.3334 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3229 -0.0082 1.1664 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7538 0.4573 2.5217 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5863 1.0242 0.5059 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1121 2.3264 0.2740 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3533 2.1137 -0.5674 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2237 1.1221 0.1822 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4753 -0.1853 0.1982 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3227 -1.3674 0.4283 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7232 -1.0603 0.8928 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4406 -0.0384 0.0921 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5565 0.5422 0.9277 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0491 -0.6800 -1.1652 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9661 0.4165 -2.2154 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5588 0.9724 -1.9422 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5712 1.0571 -0.4524 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2015 2.2897 -0.1530 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5977 0.1252 -2.4610 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4352 -1.1335 -0.9585 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5321 -0.6762 -1.5677 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7218 -1.3612 -1.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9124 -1.1500 -1.5019 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2900 -2.2826 -0.1696 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8832 -2.2050 -0.0367 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8716 1.2169 1.2359 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3717 1.6649 -1.2098 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0602 2.0653 -2.5089 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4051 -0.3014 0.3401 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4624 -2.8622 1.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5975 -3.8018 0.3423 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1540 -3.0402 -0.0875 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7282 -1.9413 -0.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7459 -0.9787 -1.4791 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8351 0.3711 -1.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4722 1.1343 1.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1087 1.8758 0.2733 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4183 -0.4783 -0.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6612 -0.3874 0.0670 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7460 -0.7200 2.9602 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2860 -2.0984 1.9880 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5433 -1.8507 0.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1064 -1.9544 2.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1540 -0.0611 3.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7997 0.2774 2.7666 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5631 1.5433 2.7003 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8324 0.6006 -0.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5893 2.9700 -0.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3769 2.8808 1.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0037 1.5680 -1.4910 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8713 3.0405 -0.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3414 1.5104 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9873 -0.2711 -0.8181 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4471 -1.9597 -0.5283 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9155 -2.1153 1.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2858 -2.0348 0.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 -0.8520 1.9821 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3693 1.6054 1.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5781 0.0055 1.8942 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5495 0.4024 0.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4049 -1.5003 -1.4885 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0363 0.0326 -3.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6660 1.2431 -2.0299 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4347 1.9798 -2.3662 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9420 2.9908 -0.7961 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3283 0.4623 -3.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4951 0.1246 -2.3195 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6612 -1.9169 1.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4041 -3.1799 -0.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4330 2.0168 0.7578 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7061 1.4860 2.3081 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1851 1.2161 -3.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0393 2.4790 -2.5495 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7590 2.8529 -2.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2020 -0.1351 -0.2154 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 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 25 28 1 0 23 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 14 35 1 0 4 36 1 0 36 37 1 0 3 38 1 0 7 2 1 0 35 9 1 0 18 12 1 0 26 21 1 0 34 29 1 0 26 17 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 6 3 43 1 6 4 44 1 6 5 45 1 0 5 46 1 0 6 47 1 6 9 48 1 6 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 6 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 17 61 1 1 18 62 1 6 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 6 24 71 1 0 24 72 1 0 25 73 1 6 27 74 1 0 28 75 1 0 30 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 37 81 1 0 37 82 1 0 37 83 1 0 38 84 1 0 M END

Standard InCHIKey	MKAWBADWUNBVAW-PGJQYQLYSA-N
Standard InCHI	InChI=1S/C30H46O8/c1-16-27(33)23(35-4)14-26(37-16)38-19-7-9-28(2)18(12-19)5-6-21-20(28)8-10-29(3)22(13-24(31)30(21,29)34)17-11-25(32)36-15-17/h11,16,18-24,26-27,31,33-34H,5-10,12-15H2,1-4H3/t16-,18+,19+,20+,21-,22-,23-,24+,26+,27+,28+,29-,30-/m1/s1
SMILES	C[C@@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](C[C@@H]([C@]32O)O)C2=CC(=O)OC2)C1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.32	Volume:	541.146 ? Van der Waals volume.
Dense:	0.987	LogP:	2.805 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.086 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.186 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	32.0
TPSA:	114.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.372	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.293	Fsp³:	0.9
MCE-18:	109.474 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.762	Fluc inhibitor:	0.011 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.17	Promiscuous compounds:	0.617

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.454	MDCK Permeability:	-5.146
Pgp-inhibitor:	0.036	Pgp-substrate:	0.196
PAMPA:	0.951 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.128	30% Bioavailability (F30%):	0.103
50% Bioavailability (F50%):	0.848

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034	MRP1:	0.798
Plasma Protein Binding (PPB):	68.089%	Volume Distribution (VD):	-0.129
Fu:	36.169% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.025
BSEP inhibitor:	0.887

ADMET: Metabolism

CYP1A2-inhibitor:	0.01	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.046	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.708	CYP3A4-substrate:	0.895
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.178
HLM stability:	0.1 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.344

Half-life (T1/2):

2.366

ADMET: Toxicity

hERG Blockers:	0.063	hERG Blockers (10um):	0.526
Human Hepatotoxicity (H-HT):	0.542	Drug-induced Liver Injury (DILI):	0.972
AMES Toxicity:	0.989	Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.945	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.74
Hematotoxicity:	0.958	Drug-induced Nephrotoxicity:	0.993
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.877
A549 Cytotoxicity:	0.982	Hek293 Cytotoxicity:	0.983
BCF:	1.258 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.754 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.162 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.57 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12987	Rhododendron farrerae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12987	Rhododendron farrerae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18054	Curvularia coicis	Species	Pleosporaceae	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

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

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 NPC260365 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	14247
0.1-0.2	31004
0.2-0.3	4249
0.3-0.4	166
0.4-0.5	125
0.5-0.6	43
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7975	Intermediate Similarity	NPC84949
0.7975	Intermediate Similarity	NPC480562
0.7975	Intermediate Similarity	NPC74945
0.7975	Intermediate Similarity	NPC31354
0.7975	Intermediate Similarity	NPC69576
0.7625	Intermediate Similarity	NPC99080
0.7294	Intermediate Similarity	NPC103534
0.7294	Intermediate Similarity	NPC44899
0.7294	Intermediate Similarity	NPC304260
0.7294	Intermediate Similarity	NPC29639
0.6744	Remote Similarity	NPC483822
0.6512	Remote Similarity	NPC152615
0.6364	Remote Similarity	NPC484202
0.6353	Remote Similarity	NPC471633
0.6207	Remote Similarity	NPC34390
0.618	Remote Similarity	NPC93883
0.6136	Remote Similarity	NPC199428
0.6136	Remote Similarity	NPC109448
0.6136	Remote Similarity	NPC310341
0.6067	Remote Similarity	NPC180079
0.6067	Remote Similarity	NPC290693
0.6023	Remote Similarity	NPC477580
0.587	Remote Similarity	NPC72260
0.5843	Remote Similarity	NPC479356
0.5843	Remote Similarity	NPC479355
0.5833	Remote Similarity	NPC55532
0.5823	Remote Similarity	NPC186668
0.5795	Remote Similarity	NPC99620
0.5714	Remote Similarity	NPC484212
0.5638	Remote Similarity	NPC488935
0.5638	Remote Similarity	NPC5883
0.5638	Remote Similarity	NPC488936
0.5591	Remote Similarity	NPC193893
0.5495	Remote Similarity	NPC5311
0.5474	Remote Similarity	NPC173555
0.5464	Remote Similarity	NPC603096
0.5426	Remote Similarity	NPC268326
0.5426	Remote Similarity	NPC153085
0.54	Remote Similarity	NPC486146
0.5385	Remote Similarity	NPC475419
0.5361	Remote Similarity	NPC115349
0.5354	Remote Similarity	NPC486143
0.5354	Remote Similarity	NPC486142
0.5354	Remote Similarity	NPC486149
0.5301	Remote Similarity	NPC480911
0.5238	Remote Similarity	NPC120390
0.5238	Remote Similarity	NPC74259
0.5213	Remote Similarity	NPC250556
0.5192	Remote Similarity	NPC329636
0.5189	Remote Similarity	NPC474908
0.5185	Remote Similarity	NPC474423
0.5158	Remote Similarity	NPC305574
0.5102	Remote Similarity	NPC30483
0.5102	Remote Similarity	NPC470897
0.51	Remote Similarity	NPC231518
0.51	Remote Similarity	NPC488944
0.5054	Remote Similarity	NPC481208
0.5051	Remote Similarity	NPC236973
0.5051	Remote Similarity	NPC292467
0.5048	Remote Similarity	NPC486144
0.5048	Remote Similarity	NPC486145
0.5048	Remote Similarity	NPC486147
0.5048	Remote Similarity	NPC486148
0.5047	Remote Similarity	NPC486134
0.5047	Remote Similarity	NPC486141

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC260365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5872
0.1-0.2	3154
0.2-0.3	108
0.3-0.4	5
0.4-0.5	1
0.5-0.6	7
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6703	Remote Similarity	NPD8377	Phase 4
0.6277	Remote Similarity	NPD8378	Pre-clinical
0.6277	Remote Similarity	NPD8379	Approved
0.587	Remote Similarity	NPD8294	Phase 4
0.5543	Remote Similarity	NPD8335	Phase 4
0.5484	Remote Similarity	NPD7516	Pre-clinical
0.5474	Remote Similarity	NPD8296	Phase 4
0.5319	Remote Similarity	NPD8380	Approved
0.5213	Remote Similarity	NPD7507	Pre-clinical
0.51	Remote Similarity	NPD8033	Approved

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