NPASS Compound

Natural Product: NPC484202

Natural Product ID	NPC484202
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WYEQRNLCWWZJJT-UDZBTMSNSA-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]

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 0.6314 0.9299 1.2247 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1207 -0.0322 0.1483 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6843 -1.3782 0.4676 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6624 -1.9177 -0.5359 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5638 -0.8651 -1.1150 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8199 0.2978 -1.7019 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4555 0.5424 -1.1814 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5745 0.1746 -2.2317 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9466 0.7549 -1.9533 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0803 1.0184 -0.4466 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3827 -0.1230 0.2016 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9614 -0.3347 1.5562 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3862 -0.8447 1.2518 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1891 0.3404 0.8253 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8041 0.9289 2.0734 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3497 -0.1356 -0.0283 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6790 1.0452 -0.9243 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3480 1.7410 -1.1409 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4433 1.3450 0.0082 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3544 2.5164 0.8079 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5545 -0.5243 0.7250 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7420 0.0470 0.6165 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6886 -0.6108 1.5205 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9092 -0.3313 1.6837 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0062 -1.6100 2.1778 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6789 -1.6014 1.7491 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5467 -0.4855 -0.2037 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8263 -0.7879 -0.5588 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6012 0.5353 -0.6233 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0008 0.3398 -0.0705 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5646 -0.9816 -0.5561 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6647 -2.1060 -0.1037 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3633 -2.8684 -1.2335 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4556 -1.6277 0.3904 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8144 -1.1863 0.0290 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8362 1.3959 -0.3400 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2458 1.9777 0.8529 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9721 0.3689 2.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1322 1.6356 1.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4848 1.5209 0.8153 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1312 -2.1372 0.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 -1.4066 1.4778 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0978 -2.4671 -1.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -2.6649 -0.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1094 -1.3591 -1.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4553 1.2037 -1.5537 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7429 0.2044 -2.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3638 1.6686 -1.0832 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6109 -0.9189 -2.4064 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1680 0.5970 -3.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0101 1.7011 -2.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6693 -0.0226 -2.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4121 1.9222 -0.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6314 -1.0570 -0.3917 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4163 -0.9985 2.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1345 0.6368 2.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7470 -1.3520 2.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2841 -1.5972 0.4293 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4613 1.9705 2.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9149 0.9618 2.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4397 0.3857 2.9743 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0431 -0.9982 -0.6766 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3436 1.7854 -0.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1806 0.7301 -1.8466 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9861 1.4706 -2.1280 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5266 2.8531 -1.1886 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9135 3.2396 0.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0478 0.8873 -0.0367 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4418 -2.5675 1.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0422 -1.3631 2.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9785 -1.2853 -1.5152 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1135 1.2942 0.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6942 0.8971 -1.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8803 0.2390 1.0190 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6998 -0.9672 -1.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1513 -2.7664 0.6283 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1028 -2.8764 -1.8872 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5283 -1.2722 -0.6475 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7967 1.2400 1.5036 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9204 2.8258 0.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3357 2.2601 1.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 16 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 5 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 31 35 1 0 30 36 1 0 36 37 1 0 7 2 1 0 19 10 1 0 26 21 1 0 34 28 1 0 11 2 1 0 19 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 6 6 46 1 0 6 47 1 0 7 48 1 1 8 49 1 0 8 50 1 0 9 51 1 0 9 52 1 0 10 53 1 6 11 54 1 6 12 55 1 0 12 56 1 0 13 57 1 0 13 58 1 0 15 59 1 0 15 60 1 0 15 61 1 0 16 62 1 6 17 63 1 0 17 64 1 0 18 65 1 0 18 66 1 0 20 67 1 0 22 68 1 0 26 69 1 0 26 70 1 0 28 71 1 6 29 72 1 0 29 73 1 0 30 74 1 1 31 75 1 6 32 76 1 1 33 77 1 0 35 78 1 0 37 79 1 0 37 80 1 0 37 81 1 0 M END

Standard InCHIKey	WYEQRNLCWWZJJT-UDZBTMSNSA-N
Standard InCHI	InChI=1S/C29H44O8/c1-27-9-6-18(36-24-14-22(34-3)25(31)26(32)37-24)13-17(27)4-5-21-20(27)7-10-28(2)19(8-11-29(21,28)33)16-12-23(30)35-15-16/h12,17-22,24-26,31-33H,4-11,13-15H2,1-3H3/t17-,18+,19-,20+,21-,22+,24-,25-,26-,27+,28-,29+/m1/s1
SMILES	C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1)O[C@H]1C[C@@H]([C@H]([C@H](O)O1)O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	520.3	Volume:	523.85 ? Van der Waals volume.
Dense:	0.993	LogP:	2.114 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.541 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.082 ? 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:	0.383	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.111	Fsp³:	0.897
MCE-18:	107.782 ? 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:	0.823	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? 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:	0.178	Promiscuous compounds:	0.268

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.444	MDCK Permeability:	-5.168
Pgp-inhibitor:	0.203	Pgp-substrate:	0.682
PAMPA:	0.895 ? 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):	0.071
20% Bioavailability (F20%):	0.287	30% Bioavailability (F30%):	0.482
50% Bioavailability (F50%):	0.826

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.405	MRP1:	0.531
Plasma Protein Binding (PPB):	91.936%	Volume Distribution (VD):	0.023
Fu:	6.05% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.951	BCRP inhibitor:	0.257
BSEP inhibitor:	0.826

ADMET: Metabolism

CYP1A2-inhibitor:	0.046	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.813	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.565
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.164
HLM stability:	0.148 ? 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):

6.12

Half-life (T1/2):

3.213

ADMET: Toxicity

hERG Blockers:	0.191	hERG Blockers (10um):	0.681
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.961	Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.932	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.991
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.747
Hematotoxicity:	0.694	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.825
A549 Cytotoxicity:	0.621	Hek293 Cytotoxicity:	0.966
BCF:	0.634 ? 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:	3.363 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.966 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.251 ? 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
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	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	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
IC50	1

Activity Type	# Activity
Single protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24787	Single protein	Neurogenic locus notch homolog protein 1	Mus musculus	IC50	=	2700.0	nM	PMID[29693393]

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 NPC484202 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	12535
0.1-0.2	33346
0.2-0.3	3696
0.3-0.4	52
0.4-0.5	109
0.5-0.6	81
0.6-0.7	26
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
0.716	Intermediate Similarity	NPC471633
0.6905	Remote Similarity	NPC199428
0.6905	Remote Similarity	NPC109448
0.6905	Remote Similarity	NPC310341
0.6747	Remote Similarity	NPC99620
0.6744	Remote Similarity	NPC483822
0.6744	Remote Similarity	NPC93883
0.6591	Remote Similarity	NPC72260
0.6588	Remote Similarity	NPC5311
0.6588	Remote Similarity	NPC99080
0.6522	Remote Similarity	NPC55532
0.6344	Remote Similarity	NPC486143
0.6344	Remote Similarity	NPC486142
0.6344	Remote Similarity	NPC486149
0.6211	Remote Similarity	NPC486146
0.6207	Remote Similarity	NPC34390
0.6162	Remote Similarity	NPC120390
0.6162	Remote Similarity	NPC475419
0.6154	Remote Similarity	NPC103534
0.6154	Remote Similarity	NPC44899
0.6154	Remote Similarity	NPC304260
0.6154	Remote Similarity	NPC29639
0.6087	Remote Similarity	NPC30483
0.6087	Remote Similarity	NPC470897
0.6067	Remote Similarity	NPC180079
0.6022	Remote Similarity	NPC236973
0.6022	Remote Similarity	NPC292467
0.596	Remote Similarity	NPC486144
0.596	Remote Similarity	NPC486145
0.596	Remote Similarity	NPC486147
0.596	Remote Similarity	NPC486148
0.5922	Remote Similarity	NPC474423
0.5889	Remote Similarity	NPC250556
0.5843	Remote Similarity	NPC469750
0.5843	Remote Similarity	NPC477580
0.5842	Remote Similarity	NPC74259
0.5824	Remote Similarity	NPC305574
0.5823	Remote Similarity	NPC268829
0.5823	Remote Similarity	NPC295110
0.58	Remote Similarity	NPC475590
0.5784	Remote Similarity	NPC474908
0.5784	Remote Similarity	NPC486134
0.5784	Remote Similarity	NPC486141
0.5778	Remote Similarity	NPC76572
0.5778	Remote Similarity	NPC152615
0.5778	Remote Similarity	NPC193382
0.5714	Remote Similarity	NPC329986
0.5714	Remote Similarity	NPC140092
0.5667	Remote Similarity	NPC479356
0.5667	Remote Similarity	NPC77299
0.5667	Remote Similarity	NPC480906
0.5667	Remote Similarity	NPC479355
0.5618	Remote Similarity	NPC473852
0.5604	Remote Similarity	NPC480914
0.551	Remote Similarity	NPC486135
0.551	Remote Similarity	NPC486137
0.5506	Remote Similarity	NPC474418
0.5474	Remote Similarity	NPC173555
0.5455	Remote Similarity	NPC232785
0.5455	Remote Similarity	NPC486139
0.5426	Remote Similarity	NPC193893
0.5385	Remote Similarity	NPC196429
0.5376	Remote Similarity	NPC88668
0.537	Remote Similarity	NPC286809
0.5368	Remote Similarity	NPC480907
0.5354	Remote Similarity	NPC125077
0.5347	Remote Similarity	NPC486138
0.5347	Remote Similarity	NPC276838
0.5326	Remote Similarity	NPC6108
0.5326	Remote Similarity	NPC89514
0.5326	Remote Similarity	NPC480915
0.5312	Remote Similarity	NPC488935
0.5312	Remote Similarity	NPC5883
0.5312	Remote Similarity	NPC488936
0.5306	Remote Similarity	NPC240070
0.5275	Remote Similarity	NPC99728
0.5275	Remote Similarity	NPC87250
0.5275	Remote Similarity	NPC244402
0.5275	Remote Similarity	NPC50305
0.5269	Remote Similarity	NPC10823
0.5253	Remote Similarity	NPC231518
0.5253	Remote Similarity	NPC488944
0.5213	Remote Similarity	NPC484212
0.5204	Remote Similarity	NPC32177
0.5204	Remote Similarity	NPC469756
0.5204	Remote Similarity	NPC275901
0.52	Remote Similarity	NPC208193
0.5192	Remote Similarity	NPC329636
0.5192	Remote Similarity	NPC486136
0.5165	Remote Similarity	NPC158344
0.5161	Remote Similarity	NPC157376
0.5161	Remote Similarity	NPC17896
0.5161	Remote Similarity	NPC469755
0.5161	Remote Similarity	NPC284406
0.5161	Remote Similarity	NPC197707
0.5161	Remote Similarity	NPC251866
0.5161	Remote Similarity	NPC142066
0.5161	Remote Similarity	NPC603972
0.5152	Remote Similarity	NPC188234
0.5152	Remote Similarity	NPC480910
0.5152	Remote Similarity	NPC480909
0.5119	Remote Similarity	NPC222875
0.5119	Remote Similarity	NPC25177
0.5098	Remote Similarity	NPC146857
0.506	Remote Similarity	NPC187302
0.5054	Remote Similarity	NPC219085
0.5054	Remote Similarity	NPC84987
0.5054	Remote Similarity	NPC486129

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC484202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5659
0.1-0.2	3385
0.2-0.3	90
0.3-0.4	2
0.4-0.5	3
0.5-0.6	8
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
0.6591	Remote Similarity	NPD8294	Phase 4
0.6067	Remote Similarity	NPD8335	Phase 4
0.5889	Remote Similarity	NPD7507	Pre-clinical
0.5652	Remote Similarity	NPD8380	Approved
0.5612	Remote Similarity	NPD8378	Pre-clinical
0.5612	Remote Similarity	NPD8379	Approved
0.5474	Remote Similarity	NPD8296	Phase 4
0.5253	Remote Similarity	NPD8033	Approved
0.5161	Remote Similarity	NPD7319	Approved
0.5158	Remote Similarity	NPD7516	Pre-clinical

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