NPASS Compound

Natural Product: NPC486811

Natural Product ID	NPC486811
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KDKIOCIPCJDWMT-BPPFJZGASA-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:0001535] Polyprenols

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 7.7696 2.0684 -1.3901 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5649 1.1707 -1.4151 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6045 -0.0060 -0.8202 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8385 -0.4176 -0.1393 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4425 -0.9103 -0.8253 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5208 -2.0191 -0.2489 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2626 -0.5900 -1.4402 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0914 -1.2793 -1.5326 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2207 -1.4856 -0.3497 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7739 -2.0973 0.8745 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4791 -1.3807 1.9558 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9812 -1.5544 2.0281 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1699 -0.3717 1.5375 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7150 0.8213 2.3593 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5658 -0.2087 0.1163 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4155 0.2341 -0.7767 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4027 1.1902 0.0563 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7340 2.4417 0.0062 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3753 3.4360 -1.0332 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4005 2.9405 -2.0492 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3787 2.8342 1.2938 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8319 3.9599 1.5948 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3373 1.6549 2.0313 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1234 0.5486 1.1952 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2715 -0.4685 1.8819 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7771 -1.8821 1.8750 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6185 -2.2324 0.6908 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4179 -1.3216 0.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5088 0.0500 0.8370 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2510 0.8474 -0.1385 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1555 1.7571 0.2005 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7986 2.4781 -0.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6131 2.0666 1.5268 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2327 1.5088 2.5496 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5589 3.0738 1.6741 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0641 3.4429 2.9496 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0069 0.5465 -1.5770 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9054 1.5084 -2.3632 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 -0.8371 -2.1089 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1656 -1.7746 -0.9474 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6520 -1.8903 -0.6982 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6495 -3.1654 -1.2149 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0570 -4.1782 -0.1534 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7552 -3.4723 -0.0993 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9626 -1.0646 -3.0109 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1563 -2.3020 -0.8377 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6938 1.4976 -1.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8673 2.6193 -2.3518 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6880 2.8129 -0.5862 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6548 1.4594 -1.9100 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7054 -0.5180 -0.8447 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6911 -1.3916 0.4049 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1708 0.2993 0.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3609 -2.3331 -1.8954 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4268 -0.8514 -2.3448 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8874 -3.2271 0.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1253 -1.9796 2.6178 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8950 -0.3738 1.7470 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 -2.1626 2.8795 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2318 0.5041 3.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8948 1.4994 2.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3996 1.4280 1.7344 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3350 0.5859 0.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1958 -0.5760 -1.1232 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8623 0.7372 -1.6505 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3279 3.8848 -1.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1796 4.2691 -0.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0306 3.0845 -2.9493 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3188 -0.1840 2.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4590 -2.0178 2.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -2.6487 1.9530 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0649 -0.1333 1.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1374 1.7333 -1.7386 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1599 3.2698 -1.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7249 2.9305 -0.5837 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0651 4.5350 3.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4774 2.9338 3.7321 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1177 3.0994 3.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9405 -1.0724 -2.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8059 -1.7077 0.3990 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0362 -2.9039 -0.8933 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2367 -1.1392 -1.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4888 -3.5050 -2.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0682 -5.2431 -0.3987 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8437 -3.8842 0.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8644 -4.0946 -0.3248 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3254 -1.9706 -2.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4856 -2.9359 -1.5141 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 3 5 1 0 5 6 2 0 5 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 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 18 21 1 0 21 22 2 0 21 23 1 0 24 23 1 1 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 31 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 30 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 40 41 1 1 40 42 1 0 42 43 1 0 43 44 1 0 39 45 1 0 9 46 1 6 15 9 1 0 24 17 1 0 44 27 1 0 12 10 1 0 25 13 1 0 40 28 1 0 44 42 1 0 29 24 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 4 51 1 0 4 52 1 0 4 53 1 0 8 54 1 0 8 55 1 0 10 56 1 6 11 57 1 0 11 58 1 0 12 59 1 1 14 60 1 0 14 61 1 0 14 62 1 0 15 63 1 1 16 64 1 0 16 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 25 69 1 1 26 70 1 0 26 71 1 0 29 72 1 1 32 73 1 0 32 74 1 0 32 75 1 0 36 76 1 0 36 77 1 0 36 78 1 0 39 79 1 6 41 80 1 0 41 81 1 0 41 82 1 0 42 83 1 6 43 84 1 0 43 85 1 0 44 86 1 6 45 87 1 0 46 88 1 0 M END

Standard InCHIKey	KDKIOCIPCJDWMT-BPPFJZGASA-N
Standard InCHI	InChI=1S/C36H42O10/c1-7-14(2)30(40)45-13-35(43)22-10-21(22)33(4)23(35)11-20-18(12-37)32(42)46-36(20)24(33)9-17-16-8-19(16)34(5)26(17)27(36)25(28(38)29(34)39)15(3)31(41)44-6/h7,16,19,21-24,27,29,37,39,43H,8-13H2,1-6H3/b14-7+,25-15+/t16-,19-,21-,22+,23+,24+,27+,29+,33+,34+,35-,36+/m1/s1
SMILES	C/C=C(C)/C(=O)OC[C@]1([C@H]2C[C@H]2[C@@]2(C)[C@@H]1CC1=C(CO)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

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.28	Volume:	629.571 ? Van der Waals volume.
Dense:	1.007	LogP:	1.775 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.223 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.937 ? 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:	6.723	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:	0.5	Fluc inhibitor:	0.078 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.565 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.179	Promiscuous compounds:	0.588

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.106	MDCK Permeability:	-4.811
Pgp-inhibitor:	0.016	Pgp-substrate:	0.107
PAMPA:	0.973 ? 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):	0.028
20% Bioavailability (F20%):	0.958	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	0.981
Plasma Protein Binding (PPB):	77.178%	Volume Distribution (VD):	-0.021
Fu:	24.962% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.189
BSEP inhibitor:	0.936

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.404
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.981
HLM stability:	0.033 ? 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):

2.464

Half-life (T1/2):

1.724

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.059
Human Hepatotoxicity (H-HT):	0.873	Drug-induced Liver Injury (DILI):	0.715
AMES Toxicity:	0.651	Rat Oral Acute Toxicity:	0.405
Maximum Recommended Daily Dose:	0.925	Skin Sensitization:	0.995
Carcinogencity:	0.805	Eye Corrosion:	0.0
Eye Irritation:	0.02	Respiratory Toxicity:	0.39
Drug-induced Neurotoxicity:	0.048	Ototoxicity:	0.934
Hematotoxicity:	0.837	Drug-induced Nephrotoxicity:	0.99
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.243
A549 Cytotoxicity:	0.194	Hek293 Cytotoxicity:	0.423
BCF:	0.617 ? 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:	3.845 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.929 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.067 ? 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	=	770.0	nM	PMID[27997206]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	21.0	nM	PMID[27997206]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	37.0	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 NPC486811 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	20423
0.1-0.2	28830
0.2-0.3	546
0.3-0.4	17
0.4-0.5	12
0.5-0.6	6
0.6-0.7	6
0.7-0.8	0
0.8-0.85	1
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC220757
0.9259	High Similarity	NPC196921
0.8987	High Similarity	NPC275236
0.8875	High Similarity	NPC15095
0.878	High Similarity	NPC486799
0.8571	High Similarity	NPC19772
0.8452	Intermediate Similarity	NPC35109
0.7912	Intermediate Similarity	NPC486798
0.7816	Intermediate Similarity	NPC59488
0.7683	Intermediate Similarity	NPC486809
0.7634	Intermediate Similarity	NPC486810
0.75	Intermediate Similarity	NPC34963
0.75	Intermediate Similarity	NPC186637
0.7416	Intermediate Similarity	NPC299570
0.7368	Intermediate Similarity	NPC290020
0.7234	Intermediate Similarity	NPC164241
0.7021	Intermediate Similarity	NPC241935
0.7021	Intermediate Similarity	NPC486803
0.69	Remote Similarity	NPC58029
0.6875	Remote Similarity	NPC486797
0.6837	Remote Similarity	NPC279478
0.6629	Remote Similarity	NPC17938
0.6437	Remote Similarity	NPC486812
0.604	Remote Similarity	NPC469673
0.5761	Remote Similarity	NPC263046
0.5682	Remote Similarity	NPC309497
0.5682	Remote Similarity	NPC611150
0.5294	Remote Similarity	NPC469381
0.5248	Remote Similarity	NPC254823
0.5049	Remote Similarity	NPC486807

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486811 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7093
0.1-0.2	2000
0.2-0.3	57
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