NPASS Compound

Natural Product: NPC479043

Natural Product ID	NPC479043
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CCDFIURNRKYDLL-YWRXPCAZSA-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 2D 101105 0 0 0 0 0 0 0 0999 V2000 7.7929 4.9139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3834 4.4009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9738 3.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4608 5.2974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5643 3.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3063 4.1917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3038 1.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 1.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3557 -2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5048 -3.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -3.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 -3.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 -2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8943 -1.2135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6443 -2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0582 -3.8933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1443 -2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 0.0855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 -0.8787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2029 -0.3656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8131 1.0046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3520 -1.3298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 -1.5484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2029 -2.0614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4634 -3.5386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3520 -1.0972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7615 -1.6103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9106 -0.6461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6501 0.8311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2406 1.3442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0915 0.3800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3038 -4.3246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5643 -5.8018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4152 -6.7660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9738 -6.3149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2343 -7.7921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6439 -8.3051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7929 -7.3409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5325 -5.8637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1229 -5.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5241 0.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3442 2.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 1.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8173 0.5402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2082 -0.0214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9320 1.5439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2025 5.4269 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2799 6.3234 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3060 3.5043 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0644 3.0644 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0460 5.8624 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6549 2.5513 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9478 6.7069 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7973 5.9784 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9993 4.9600 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8158 2.8825 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8578 2.6401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6004 -0.7041 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5048 -1.5484 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6538 -4.4409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4689 -2.3277 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6878 -4.7348 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6548 -5.2888 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9422 -4.4926 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6338 -5.2888 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6673 -3.6096 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9320 -2.6139 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2548 0.0151 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6331 -2.6954 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1443 -4.0126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8486 -1.1882 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 1.0497 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5010 -2.2940 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3162 -0.1808 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0095 0.0184 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2001 -3.0447 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3201 -1.1591 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7992 1.7953 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1621 2.8421 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 1.4948 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0853 -8.7563 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9043 -9.7823 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2025 -7.8540 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6815 -4.8995 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0445 -3.8527 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0159 0.4364 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8615 2.0548 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3673 -0.8986 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6560 3.6844 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8384 2.0865 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0741 2.7056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1607 2.4042 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2686 0.8630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9283 2.6586 0.0000 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 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 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 17 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 16 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 15 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 11 46 1 6 46 47 1 0 47 48 1 0 47 49 1 0 10 50 1 0 50 51 1 0 51 52 2 0 51 53 1 0 23 8 1 0 36 31 1 0 45 40 1 0 47 9 1 0 17 11 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 0 2 58 1 0 3 59 1 6 4 60 1 0 4 61 1 0 4 62 1 0 8 63 1 6 9 64 1 6 10 65 1 6 12 66 1 6 13 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 6 16 73 1 6 18 74 1 0 18 75 1 0 22 76 1 0 22 77 1 0 22 78 1 0 23 79 1 6 27 80 1 0 27 81 1 0 27 82 1 0 32 83 1 0 33 84 1 0 34 85 1 0 35 86 1 0 36 87 1 0 41 88 1 0 42 89 1 0 43 90 1 0 44 91 1 0 45 92 1 0 48 93 1 0 48 94 1 0 48 95 1 0 49 96 1 0 49 97 1 0 49 98 1 0 53 99 1 0 53100 1 0 53101 1 0 M END

Standard InCHIKey	CCDFIURNRKYDLL-YWRXPCAZSA-N
Standard InCHI	InChI=1S/C40H48O13/c1-9-22(2)35(44)51-31-30-33(48-25(5)42)40(53-38(30,7)8)23(3)20-29(50-36(45)27-16-12-10-13-17-27)32(52-37(46)28-18-14-11-15-19-28)39(40,21-47-24(4)41)34(31)49-26(6)43/h10-19,22-23,29-34H,9,20-21H2,1-8H3/t22-,23+,29-,30-,31+,32-,33+,34+,39-,40+/m0/s1
SMILES	CC[C@H](C)C(=O)O[C@@H]1[C@H]2[C@H]([C@@]3([C@H](C)C[C@@H]([C@@H]([C@@]3(COC(=O)C)[C@@H]1OC(=O)C)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC2(C)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	736.31	Volume:	740.249 ? Van der Waals volume.
Dense:	0.995	LogP:	4.904 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.887 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.687 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	32.0
TPSA:	167.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.223	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.172	Fsp³:	0.55
MCE-18:	174.194 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.702	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.178 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.242	Promiscuous compounds:	0.12

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.164	MDCK Permeability:	-4.826
Pgp-inhibitor:	1.0	Pgp-substrate:	0.284
PAMPA:	0.274 ? 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):	0.0
20% Bioavailability (F20%):	0.231	30% Bioavailability (F30%):	0.772
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.63	MRP1:	1.0
Plasma Protein Binding (PPB):	90.398%	Volume Distribution (VD):	-0.228
Fu:	11.827% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.935	BCRP inhibitor:	0.002
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

3.988

Half-life (T1/2):

0.555

ADMET: Toxicity

hERG Blockers:	0.072	hERG Blockers (10um):	0.425
Human Hepatotoxicity (H-HT):	0.062	Drug-induced Liver Injury (DILI):	0.906
AMES Toxicity:	0.684	Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.373	Skin Sensitization:	0.999
Carcinogencity:	0.757	Eye Corrosion:	0.0
Eye Irritation:	0.156	Respiratory Toxicity:	0.053
Drug-induced Neurotoxicity:	0.761	Ototoxicity:	0.155
Hematotoxicity:	0.138	Drug-induced Nephrotoxicity:	0.694
Genotoxicity:	0.471	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.228	Hek293 Cytotoxicity:	0.435
BCF:	0.72 ? 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:	3.72 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.384 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.991 ? 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
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	Species	Celastraceae	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	1

Activity Type	# Activity
Cell line	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
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	80.11	%	PMID[31713425]

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 NPC479043 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	15390
0.1-0.2	32380
0.2-0.3	1513
0.3-0.4	390
0.4-0.5	103
0.5-0.6	48
0.6-0.7	25
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8906	High Similarity	NPC137718
0.8594	High Similarity	NPC51314
0.8333	Intermediate Similarity	NPC148062
0.8308	Intermediate Similarity	NPC473060
0.791	Intermediate Similarity	NPC147880
0.7333	Intermediate Similarity	NPC479040
0.7042	Intermediate Similarity	NPC147217
0.6901	Remote Similarity	NPC90257
0.6901	Remote Similarity	NPC69357
0.6667	Remote Similarity	NPC483845
0.6667	Remote Similarity	NPC4341
0.6622	Remote Similarity	NPC483844
0.6571	Remote Similarity	NPC481047
0.6571	Remote Similarity	NPC481045
0.6533	Remote Similarity	NPC252314
0.6486	Remote Similarity	NPC471107
0.6438	Remote Similarity	NPC191082
0.641	Remote Similarity	NPC481488
0.64	Remote Similarity	NPC479044
0.6364	Remote Similarity	NPC483848
0.6316	Remote Similarity	NPC472569
0.6316	Remote Similarity	NPC16912
0.6282	Remote Similarity	NPC481489
0.6267	Remote Similarity	NPC254558
0.6216	Remote Similarity	NPC479047
0.6216	Remote Similarity	NPC291638
0.6104	Remote Similarity	NPC11685
0.6104	Remote Similarity	NPC472570
0.6076	Remote Similarity	NPC483849
0.6053	Remote Similarity	NPC471100
0.6053	Remote Similarity	NPC605884
0.6026	Remote Similarity	NPC184747
0.5921	Remote Similarity	NPC139067
0.5897	Remote Similarity	NPC609924
0.5875	Remote Similarity	NPC481050
0.5844	Remote Similarity	NPC473088
0.5802	Remote Similarity	NPC483887
0.5802	Remote Similarity	NPC158020
0.5802	Remote Similarity	NPC481486
0.5714	Remote Similarity	NPC67777
0.5696	Remote Similarity	NPC57628
0.5679	Remote Similarity	NPC609221
0.5676	Remote Similarity	NPC66761
0.5676	Remote Similarity	NPC483843
0.5676	Remote Similarity	NPC476094
0.5658	Remote Similarity	NPC483902
0.5658	Remote Similarity	NPC472577
0.5541	Remote Similarity	NPC473081
0.5526	Remote Similarity	NPC90614
0.5513	Remote Similarity	NPC43241
0.5467	Remote Similarity	NPC475429
0.5467	Remote Similarity	NPC211137
0.5465	Remote Similarity	NPC75600
0.5465	Remote Similarity	NPC483884
0.5455	Remote Similarity	NPC17877
0.5333	Remote Similarity	NPC270498
0.5325	Remote Similarity	NPC241951
0.5325	Remote Similarity	NPC483862
0.5316	Remote Similarity	NPC483842
0.5316	Remote Similarity	NPC177340
0.5301	Remote Similarity	NPC479042
0.5256	Remote Similarity	NPC483886
0.525	Remote Similarity	NPC473758
0.5244	Remote Similarity	NPC70716
0.5244	Remote Similarity	NPC97667
0.5185	Remote Similarity	NPC41481
0.5185	Remote Similarity	NPC306146
0.5185	Remote Similarity	NPC483841
0.5181	Remote Similarity	NPC282239
0.5181	Remote Similarity	NPC473613
0.5181	Remote Similarity	NPC471102
0.5181	Remote Similarity	NPC481490
0.5176	Remote Similarity	NPC608007
0.5132	Remote Similarity	NPC195647
0.5116	Remote Similarity	NPC473109
0.5114	Remote Similarity	NPC473115
0.5063	Remote Similarity	NPC281717
0.5062	Remote Similarity	NPC471104
0.506	Remote Similarity	NPC106895
0.506	Remote Similarity	NPC95265

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4032
0.1-0.2	4967
0.2-0.3	151
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