NPASS Compound

Natural Product: NPC59488

Natural Product ID	NPC59488
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KLQOLSXBHGJGJD-JCXMIBBCSA-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:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 88 95 0 0 0 0 0 0 0 0999 V2000 4.9203 0.4108 0.6442 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1904 0.6543 2.0808 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3779 1.4391 2.7545 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2115 2.1224 2.2666 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5709 2.8565 3.1017 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6755 2.0977 1.0062 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4962 2.8619 0.6934 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0716 2.6607 -0.7439 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2065 3.4411 -1.0332 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5530 3.9223 -2.3615 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9705 2.5766 -2.0683 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1552 1.3160 -2.2354 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0063 1.5455 -3.2202 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4825 1.2897 -0.8695 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2865 0.1558 -0.4666 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7282 -1.0180 -1.2418 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3760 -2.0644 -1.6844 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8508 -2.3417 -1.5086 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4495 -2.8775 -2.4394 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7451 -3.9920 -3.0203 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7322 -2.2496 -2.4088 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7087 -1.0753 -1.6117 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9091 0.1036 -2.5926 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2640 0.1664 -3.1288 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2705 -0.1173 -2.0372 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0255 -0.7611 -0.9597 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7022 -1.3426 -0.6058 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5879 -1.0366 0.8275 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8105 -1.6854 1.6533 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0613 -2.8312 1.1811 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7855 -1.4208 3.0724 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5353 -0.5988 3.6124 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1054 -2.0907 3.9264 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0715 -1.7761 5.3014 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4128 0.0702 1.3698 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8394 0.9225 2.0725 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8776 0.1466 1.0725 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1954 -0.8765 -0.0292 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3746 -2.2607 0.4914 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3456 -0.3500 -0.8369 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6272 -0.9513 -2.1614 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7423 0.2591 -2.0155 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5551 -0.2641 2.2067 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0971 3.0029 -1.5536 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3809 0.0001 2.7440 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4528 0.3488 4.0738 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2954 -0.4897 0.4884 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9194 0.1308 0.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6163 1.3089 0.1084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 1.5540 3.8238 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6984 3.9176 0.9220 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7118 2.4709 1.4014 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7166 3.7849 -0.1375 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2619 4.2766 -3.0004 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3821 4.6951 -2.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0068 2.3977 -1.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9357 1.0831 -2.8598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0988 2.5445 -3.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7356 0.9250 -4.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3974 1.3492 -0.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3830 0.2456 -0.6671 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1891 -0.0685 0.5849 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1438 -3.2649 -2.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3602 -1.4931 -2.0299 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0523 -2.3338 -0.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3204 -0.3196 -3.5018 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4857 -0.6646 -3.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5645 1.0786 -3.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8658 -2.5024 -0.6146 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3176 -3.3351 0.3018 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1310 -2.5544 1.1732 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0305 -3.5983 2.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4927 -0.8389 5.4656 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1176 -1.5748 5.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3941 -2.5844 5.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2070 1.1386 0.7884 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9339 -3.0062 -0.2253 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4388 -2.5740 0.5917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7910 -2.3651 1.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1781 0.1619 -0.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5857 -0.7622 -2.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1695 -1.9443 -2.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0124 1.2224 -2.4443 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4563 -0.6224 2.0287 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9465 2.6775 -1.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3220 0.3827 2.2628 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3765 -1.0862 2.6319 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3575 0.2485 4.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 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 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 17 19 1 0 19 20 2 0 19 21 1 0 22 21 1 6 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 29 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 28 35 1 0 35 36 2 0 35 37 1 0 37 38 1 0 38 39 1 1 38 40 1 0 40 41 1 0 41 42 1 0 37 43 1 0 8 44 1 6 2 45 1 0 45 46 1 0 14 8 1 0 22 16 1 0 42 25 1 0 11 9 1 0 23 12 1 0 38 26 1 0 42 40 1 0 27 22 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 7 51 1 0 7 52 1 0 9 53 1 1 10 54 1 0 10 55 1 0 11 56 1 1 13 57 1 0 13 58 1 0 13 59 1 0 14 60 1 1 15 61 1 0 15 62 1 0 18 63 1 0 18 64 1 0 18 65 1 0 23 66 1 6 24 67 1 0 24 68 1 0 27 69 1 1 30 70 1 0 30 71 1 0 30 72 1 0 34 73 1 0 34 74 1 0 34 75 1 0 37 76 1 6 39 77 1 0 39 78 1 0 39 79 1 0 40 80 1 1 41 81 1 0 41 82 1 0 42 83 1 6 43 84 1 0 44 85 1 0 45 86 1 0 45 87 1 0 46 88 1 0 M END

Standard InCHIKey	KLQOLSXBHGJGJD-JCXMIBBCSA-N
Standard InCHI	InChI=1S/C36H42O10/c1-14(12-37)7-25(38)45-13-35(43)22-10-21(22)33(4)23(35)11-19-15(2)32(42)46-36(19)24(33)9-18-17-8-20(17)34(5)27(18)28(36)26(29(39)30(34)40)16(3)31(41)44-6/h7,17,20-24,28,30,37,40,43H,8-13H2,1-6H3/b14-7+,26-16-/t17-,20-,21-,22+,23-,24+,28+,30+,33+,34+,35+,36+/m1/s1
SMILES	C/C(=CC(=O)OC[C@@]1([C@H]2C[C@H]2[C@@]2(C)[C@H]1CC1=C(C)C(=O)O[C@@]31[C@H]2CC1=C2[C@@H]3/C(=C(C)/C(=O)OC)/C(=O)[C@@H]([C@@]2(C)[C@@H]2C[C@H]12)O)O)/CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.28	Volume:	629.571 ? Van der Waals volume.
Dense:	1.007	LogP:	2.09 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.366 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.826 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	37.0
TPSA:	156.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	8.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.178	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.712	Fsp³:	0.667
MCE-18:	194.333 ? 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:	0.408	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.465 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.157	Promiscuous compounds:	0.625

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.341	MDCK Permeability:	-4.968
Pgp-inhibitor:	0.004	Pgp-substrate:	0.943
PAMPA:	0.617 ? 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%):	0.992	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.871	MRP1:	1.0
Plasma Protein Binding (PPB):	88.476%	Volume Distribution (VD):	0.013
Fu:	11.953% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.244
BSEP inhibitor:	0.93

ADMET: Metabolism

CYP1A2-inhibitor:	0.043	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.964
HLM stability:	0.336 ? 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):

2.936

Half-life (T1/2):

1.857

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.146
Human Hepatotoxicity (H-HT):	0.824	Drug-induced Liver Injury (DILI):	0.603
AMES Toxicity:	0.883	Rat Oral Acute Toxicity:	0.253
Maximum Recommended Daily Dose:	0.802	Skin Sensitization:	0.999
Carcinogencity:	0.794	Eye Corrosion:	0.0
Eye Irritation:	0.068	Respiratory Toxicity:	0.39
Drug-induced Neurotoxicity:	0.6	Ototoxicity:	0.771
Hematotoxicity:	0.877	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.197
A549 Cytotoxicity:	0.754	Hek293 Cytotoxicity:	0.606
BCF:	0.776 ? 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:	3.859 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.919 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.158 ? 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
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27997206]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	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	2
Ratio IC50	1

Activity Type	# Activity
Cell line	1
Organism	1
Others	1

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
NPT1374	Cell line	WI-38	Homo sapiens	IC50	=	4450.0	nM	PMID[27997206]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	96.0	nM	PMID[27997206]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	46.0	n.a.	PMID[27997206]

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 NPC59488 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	20817
0.1-0.2	28473
0.2-0.3	510
0.3-0.4	21
0.4-0.5	9
0.5-0.6	4
0.6-0.7	8
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC19772
0.8675	High Similarity	NPC486799
0.8523	High Similarity	NPC164241
0.8313	Intermediate Similarity	NPC15095
0.814	Intermediate Similarity	NPC299570
0.7976	Intermediate Similarity	NPC275236
0.7841	Intermediate Similarity	NPC196921
0.7826	Intermediate Similarity	NPC486798
0.7816	Intermediate Similarity	NPC486811
0.7816	Intermediate Similarity	NPC220757
0.7692	Intermediate Similarity	NPC241935
0.7692	Intermediate Similarity	NPC486803
0.7527	Intermediate Similarity	NPC486797
0.7333	Intermediate Similarity	NPC35109
0.7292	Intermediate Similarity	NPC279478
0.701	Intermediate Similarity	NPC486810
0.6875	Remote Similarity	NPC34963
0.6875	Remote Similarity	NPC186637
0.6782	Remote Similarity	NPC486809
0.66	Remote Similarity	NPC290020
0.6346	Remote Similarity	NPC58029
0.6222	Remote Similarity	NPC263046
0.6163	Remote Similarity	NPC309497
0.6163	Remote Similarity	NPC611150
0.5851	Remote Similarity	NPC17938
0.5652	Remote Similarity	NPC486812
0.5377	Remote Similarity	NPC469673
0.5273	Remote Similarity	NPC486801

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC59488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7082
0.1-0.2	2026
0.2-0.3	42
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
		NPD

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