NPASS Compound

Natural Product: NPC476866

Natural Product ID	NPC476866
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-4-[(E)-3-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-enyl]phenoxy]oxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
IUPAC Name	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-4-[(E)-3-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-enyl]phenoxy]oxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	122181705
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0003003] Hydroxycinnamic acid glycosides

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 80 83 0 0 0 0 0 0 0 0999 V2000 11.6443 -0.0527 0.3451 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8773 -0.3071 -0.2637 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9625 -0.8625 -1.5118 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8127 -1.1778 -2.1829 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6013 -0.9277 -1.5844 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4894 -0.3673 -0.3245 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1768 -0.1386 0.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9742 0.3830 1.4098 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5830 0.5730 1.8781 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3465 1.0715 3.0096 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5239 0.2074 1.0832 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2007 0.4067 1.5677 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1711 -0.0549 0.5575 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4284 0.4813 -0.8155 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9343 1.8699 -1.0500 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8105 2.1960 -0.0999 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0720 0.8819 0.1855 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9063 0.1484 1.0456 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8680 1.0903 0.7908 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4090 0.7446 0.4659 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7740 0.0459 -0.6460 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1245 -0.2477 -0.8675 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0950 0.1457 0.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7004 0.8481 1.1121 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3928 1.1611 1.3753 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4891 -0.1442 -0.2055 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9942 -0.8107 -1.2285 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4458 -1.0323 -1.3074 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8872 -1.6697 -2.2927 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2972 -0.5525 -0.3254 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7177 -0.7564 -0.3805 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0816 -1.5395 0.8373 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.5465 -1.5999 1.1237 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.2842 -0.6861 0.1910 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.5619 0.6043 0.0108 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2754 0.5098 -0.4304 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6518 1.4633 1.2778 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1743 2.7550 0.9912 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6047 -1.2645 -1.0229 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7614 -1.1762 2.4524 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6429 -2.8623 0.6257 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -0.4051 -1.5972 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9742 3.1131 -0.7234 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9527 2.8262 -0.9611 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0007 -0.4053 -1.8067 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2247 -1.0946 -2.0709 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5981 0.3853 1.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7577 -0.0384 0.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8869 -1.6108 -3.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6903 -1.1724 -2.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2968 -0.4115 -0.3599 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7822 0.6782 2.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0247 1.4747 1.8044 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1042 -0.1971 2.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3036 -1.1754 0.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5525 0.5211 -0.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4994 1.8986 -2.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1849 2.6546 0.8190 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0468 0.3286 -0.7619 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3927 -0.8123 -1.7715 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4406 1.1892 1.8437 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1010 1.7213 2.2672 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2409 0.2044 0.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3269 -1.1813 -1.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9027 -1.3326 -1.3100 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4869 -1.1875 1.7305 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9821 -2.6093 1.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2641 -0.4458 0.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1350 1.1971 -0.7619 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9828 1.0669 2.0697 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6906 1.5756 1.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1938 2.8045 1.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6094 -0.5686 -1.7211 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1084 -1.6112 3.0385 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9069 -2.9186 -0.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2194 0.1331 -2.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1384 3.1596 -0.1943 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7561 3.5683 -1.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2700 -1.3080 -1.5144 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9002 -1.5466 -1.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 34 39 1 0 33 40 1 0 32 41 1 0 21 42 1 0 16 43 1 0 15 44 1 0 14 45 1 0 3 46 1 0 6 1 1 0 18 13 1 0 25 20 1 0 36 31 1 0 1 47 1 0 2 48 1 0 4 49 1 0 5 50 1 0 7 51 1 0 8 52 1 0 12 53 1 0 12 54 1 0 13 55 1 6 14 56 1 6 15 57 1 6 16 58 1 1 17 59 1 6 22 60 1 0 24 61 1 0 25 62 1 0 26 63 1 0 27 64 1 0 31 65 1 6 32 66 1 1 33 67 1 1 34 68 1 1 35 69 1 6 37 70 1 0 37 71 1 0 38 72 1 0 39 73 1 0 40 74 1 0 41 75 1 0 42 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 46 80 1 0 M END

Standard InCHIKey	NJZKNNCKRZJHCK-OGGREQCXSA-N
Standard InCHI	InChI=1S/C30H34O16/c31-12-19-23(36)25(38)28(41)30(44-19)46-22(35)10-5-15-3-8-18(17(33)11-15)43-29-27(40)26(39)24(37)20(45-29)13-42-21(34)9-4-14-1-6-16(32)7-2-14/h1-11,19-20,23-33,36-41H,12-13H2/b9-4+,10-5+/t19-,20-,23-,24-,25+,26+,27-,28-,29-,30+/m1/s1
SMILES	C1=CC(=CC=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C=C(C=C3)/C=C/C(=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.18	Volume:	607.489 ? Van der Waals volume.
Dense:	1.07	LogP:	0.551 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.028 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.714 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	28.0
TPSA:	262.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.098	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.717	Fsp³:	0.4
MCE-18:	100.81 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.734	Fluc inhibitor:	0.807 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.198 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.646 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.423	Promiscuous compounds:	0.382

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.472	MDCK Permeability:	-5.158
Pgp-inhibitor:	0.0	Pgp-substrate:	0.054
PAMPA:	0.999 ? 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):	0.961
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	77.624%	Volume Distribution (VD):	-0.195
Fu:	21.019% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.032

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.016 ? 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):

1.164

Half-life (T1/2):

4.066

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.126
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.966
AMES Toxicity:	0.97	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	1.0
Carcinogencity:	0.047	Eye Corrosion:	0.0
Eye Irritation:	0.024	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.958
Hematotoxicity:	0.055	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.656	RPMI-8226 Immunitoxicity:	0.239
A549 Cytotoxicity:	0.413	Hek293 Cytotoxicity:	0.396
BCF:	0.588 ? 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:	3.327 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.047 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.387 ? 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
NPO33548	Clematis tashiroi	Species	Ranunculaceae	Eukaryota	aerial parts	Heping District, Taichung City, Taiwan	2012-AUG	PMID[26143931]

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
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
NPT1	Others	Radical scavenging activity	n.a.	Activity	=	7.8	%	PMID[26143931]

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 NPC476866 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	14937
0.1-0.2	28948
0.2-0.3	4311
0.3-0.4	1304
0.4-0.5	269
0.5-0.6	65
0.6-0.7	9
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9028	High Similarity	NPC476864
0.8553	High Similarity	NPC476865
0.84	Intermediate Similarity	NPC476869
0.8133	Intermediate Similarity	NPC476867
0.7821	Intermediate Similarity	NPC476868
0.7571	Intermediate Similarity	NPC202700
0.6575	Remote Similarity	NPC100389
0.6538	Remote Similarity	NPC291153
0.6522	Remote Similarity	NPC11724
0.631	Remote Similarity	NPC204937
0.6071	Remote Similarity	NPC291296
0.6071	Remote Similarity	NPC10205
0.6049	Remote Similarity	NPC157898
0.6044	Remote Similarity	NPC476871
0.6027	Remote Similarity	NPC481303
0.5972	Remote Similarity	NPC232880
0.5952	Remote Similarity	NPC225307
0.5934	Remote Similarity	NPC133984
0.593	Remote Similarity	NPC157816
0.5921	Remote Similarity	NPC52097
0.5921	Remote Similarity	NPC157554
0.5814	Remote Similarity	NPC28637
0.5806	Remote Similarity	NPC3460
0.575	Remote Similarity	NPC479473
0.575	Remote Similarity	NPC275721
0.575	Remote Similarity	NPC288416
0.575	Remote Similarity	NPC479468
0.575	Remote Similarity	NPC479474
0.5714	Remote Similarity	NPC488081
0.5663	Remote Similarity	NPC34293
0.5652	Remote Similarity	NPC300262
0.5647	Remote Similarity	NPC168358
0.5625	Remote Similarity	NPC470572
0.5618	Remote Similarity	NPC488082
0.5612	Remote Similarity	NPC484979
0.5604	Remote Similarity	NPC472876
0.5532	Remote Similarity	NPC125823
0.5532	Remote Similarity	NPC7145
0.5532	Remote Similarity	NPC143480
0.5529	Remote Similarity	NPC219677
0.5529	Remote Similarity	NPC145319
0.5506	Remote Similarity	NPC226005
0.5495	Remote Similarity	NPC262182
0.5488	Remote Similarity	NPC229784
0.5488	Remote Similarity	NPC477293
0.5481	Remote Similarity	NPC484988
0.5455	Remote Similarity	NPC471405
0.5435	Remote Similarity	NPC83743
0.5385	Remote Similarity	NPC59324
0.5385	Remote Similarity	NPC476870
0.5375	Remote Similarity	NPC186418
0.5361	Remote Similarity	NPC201148
0.5349	Remote Similarity	NPC252114
0.5349	Remote Similarity	NPC166180
0.5347	Remote Similarity	NPC599948
0.5325	Remote Similarity	NPC57751
0.5278	Remote Similarity	NPC484983
0.5275	Remote Similarity	NPC254819
0.5263	Remote Similarity	NPC604356
0.5253	Remote Similarity	NPC80068
0.5238	Remote Similarity	NPC473924
0.5238	Remote Similarity	NPC186406
0.5238	Remote Similarity	NPC287597
0.5204	Remote Similarity	NPC476620
0.5195	Remote Similarity	NPC476872
0.5176	Remote Similarity	NPC199977
0.5169	Remote Similarity	NPC281798
0.5152	Remote Similarity	NPC270675
0.5152	Remote Similarity	NPC195685
0.5119	Remote Similarity	NPC477294
0.5109	Remote Similarity	NPC205195
0.5106	Remote Similarity	NPC479767
0.51	Remote Similarity	NPC28651
0.51	Remote Similarity	NPC85751
0.51	Remote Similarity	NPC19240
0.51	Remote Similarity	NPC477629
0.5098	Remote Similarity	NPC603856
0.5091	Remote Similarity	NPC484981
0.5067	Remote Similarity	NPC313193
0.505	Remote Similarity	NPC36138

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4907
0.1-0.2	4136
0.2-0.3	91
0.3-0.4	15
0.4-0.5	1
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