NPASS Compound

Natural Product: NPC476864

Natural Product ID	NPC476864
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-(3,4-dihydroxyphenyl)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-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	122181703
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 81 84 0 0 0 0 0 0 0 0999 V2000 9.4523 1.5191 -1.2019 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2693 2.3301 -1.9573 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3662 2.8911 -1.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6356 2.6447 -0.0223 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7891 1.8256 0.6957 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6725 1.2404 0.1217 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8264 0.3848 0.9513 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7480 -0.2245 0.5344 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9714 -1.0566 1.4391 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3547 -1.1788 2.6248 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8269 -1.7257 1.0654 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0732 -2.5356 1.9493 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8756 -3.1410 1.2671 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3586 -4.0197 0.1373 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0840 -3.4383 -1.2135 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6872 -2.9433 -1.4029 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0674 -2.5807 -0.0481 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0712 -2.1006 0.8064 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1947 -1.5321 -0.2840 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1415 -1.5185 -0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -0.3440 -0.3380 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1983 -0.2798 -0.0881 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9000 -1.3200 0.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1985 -2.4526 0.7690 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8245 -2.5699 0.5360 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3161 -1.2608 0.7289 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1066 -0.2374 0.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5336 -0.2437 0.7774 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0655 -1.2638 1.2878 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3186 0.8406 0.5089 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7091 0.9059 0.7651 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9394 1.9461 1.8214 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9495 3.3453 1.2776 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7690 3.4351 0.0284 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3839 2.1023 -0.2770 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4636 1.0767 -0.3694 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1320 2.1730 -1.6044 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2253 2.4230 -2.6259 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8258 4.3347 0.2419 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6619 3.7921 0.9847 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0892 1.6871 2.5877 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1149 0.6893 -0.8939 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9206 -3.9325 -1.9829 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0184 -2.4222 -1.4843 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7885 -5.2958 0.1788 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7576 3.2408 0.5296 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1888 3.7116 -2.1242 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5936 1.0835 -1.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0816 2.5413 -3.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9953 1.6289 1.7372 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0899 0.2212 2.0107 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4539 -0.0863 -0.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6920 -3.3535 2.3822 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7830 -1.8851 2.8002 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3025 -3.7658 1.9729 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4581 -4.1773 0.2136 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2963 -4.2400 -1.9650 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7032 -2.0312 -2.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5635 -3.4413 0.3984 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6951 0.6556 -0.3562 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7106 -3.2860 1.2020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3223 -3.4843 0.7946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8212 -2.1282 1.1738 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6796 0.6452 0.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0274 -0.0789 1.2177 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0802 1.8567 2.5481 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3575 4.0070 2.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2006 3.8439 -0.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1252 1.8555 0.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9440 2.9342 -1.5787 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6176 1.1985 -1.8208 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8783 1.5397 -2.9530 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1946 4.6470 -0.6314 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4122 3.6033 0.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2276 2.4969 3.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5417 0.5712 -1.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1002 -3.5592 -2.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5320 -1.5586 -1.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1733 -5.3730 0.9249 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6687 3.5354 1.5090 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9782 4.6623 -2.3506 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 4 46 1 0 3 47 1 0 6 1 1 0 18 13 1 0 25 20 1 0 36 31 1 0 1 48 1 0 2 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 1 14 56 1 1 15 57 1 6 16 58 1 6 17 59 1 1 22 60 1 0 24 61 1 0 25 62 1 0 26 63 1 0 27 64 1 0 31 65 1 1 32 66 1 1 33 67 1 1 34 68 1 6 35 69 1 1 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 47 81 1 0 M END

Standard InCHIKey	NRNLHCNVJHJROX-SKXWEYSTSA-N
Standard InCHI	InChI=1S/C30H34O17/c31-11-19-23(37)25(39)28(42)30(45-19)47-22(36)8-4-14-2-6-18(17(34)10-14)44-29-27(41)26(40)24(38)20(46-29)12-43-21(35)7-3-13-1-5-15(32)16(33)9-13/h1-10,19-20,23-34,37-42H,11-12H2/b7-3+,8-4+/t19-,20-,23-,24-,25+,26+,27-,28-,29-,30+/m1/s1
SMILES	C1=CC(=C(C=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)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.18	Volume:	616.279 ? Van der Waals volume.
Dense:	1.081	LogP:	0.192 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.893 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.491 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	28.0
TPSA:	282.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	4.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.072	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.805	Fsp³:	0.4
MCE-18:	104.286 ? 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:	1
Colloidal aggregators:	0.734	Fluc inhibitor:	0.725 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.218 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.652 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.439	Promiscuous compounds:	0.478

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.529	MDCK Permeability:	-5.162
Pgp-inhibitor:	0.0	Pgp-substrate:	0.024
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):	0.987
20% Bioavailability (F20%):	0.999	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):	72.85%	Volume Distribution (VD):	-0.212
Fu:	23.793% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.001

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:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.015 ? 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):

1.332

Half-life (T1/2):

4.316

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.18
Human Hepatotoxicity (H-HT):	0.511	Drug-induced Liver Injury (DILI):	0.969
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.03	Skin Sensitization:	1.0
Carcinogencity:	0.034	Eye Corrosion:	0.0
Eye Irritation:	0.034	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.987
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.919
Genotoxicity:	0.673	RPMI-8226 Immunitoxicity:	0.105
A549 Cytotoxicity:	0.824	Hek293 Cytotoxicity:	0.193
BCF:	0.56 ? 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:	3.346 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.054 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.459 ? 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
ED50	1
Activity	1

Activity Type	# Activity
Others	2

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.	ED50	=	13.3	nM	PMID[26143931]
NPT1	Others	Radical scavenging activity	n.a.	Activity	=	99.8	%	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 NPC476864 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	16761
0.1-0.2	27642
0.2-0.3	3902
0.3-0.4	1209
0.4-0.5	264
0.5-0.6	49
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9028	High Similarity	NPC476866
0.875	High Similarity	NPC476867
0.8667	High Similarity	NPC476865
0.8649	High Similarity	NPC476868
0.7681	Intermediate Similarity	NPC202700
0.7564	Intermediate Similarity	NPC476869
0.6765	Remote Similarity	NPC232880
0.6753	Remote Similarity	NPC157898
0.675	Remote Similarity	NPC291296
0.6667	Remote Similarity	NPC100389
0.6667	Remote Similarity	NPC476871
0.6585	Remote Similarity	NPC157816
0.6364	Remote Similarity	NPC133984
0.6322	Remote Similarity	NPC488081
0.6173	Remote Similarity	NPC219677
0.6154	Remote Similarity	NPC229784
0.6111	Remote Similarity	NPC481303
0.6104	Remote Similarity	NPC470572
0.6047	Remote Similarity	NPC488082
0.6	Remote Similarity	NPC157554
0.5977	Remote Similarity	NPC476870
0.5949	Remote Similarity	NPC477293
0.5875	Remote Similarity	NPC473924
0.5875	Remote Similarity	NPC186406
0.5875	Remote Similarity	NPC287597
0.5814	Remote Similarity	NPC204937
0.5802	Remote Similarity	NPC291153
0.5694	Remote Similarity	NPC11724
0.5682	Remote Similarity	NPC205195
0.5612	Remote Similarity	NPC603856
0.5568	Remote Similarity	NPC226005
0.5556	Remote Similarity	NPC262182
0.5556	Remote Similarity	NPC477294
0.5556	Remote Similarity	NPC599948
0.5529	Remote Similarity	NPC292443
0.5517	Remote Similarity	NPC471405
0.5495	Remote Similarity	NPC83743
0.549	Remote Similarity	NPC227297
0.5443	Remote Similarity	NPC186418
0.5402	Remote Similarity	NPC10205
0.5395	Remote Similarity	NPC476873
0.5357	Remote Similarity	NPC34293
0.5301	Remote Similarity	NPC88043
0.5287	Remote Similarity	NPC225307
0.5281	Remote Similarity	NPC220942
0.5256	Remote Similarity	NPC59324
0.5233	Remote Similarity	NPC232228
0.5213	Remote Similarity	NPC11411
0.5208	Remote Similarity	NPC3460
0.519	Remote Similarity	NPC52097
0.5185	Remote Similarity	NPC128403
0.5185	Remote Similarity	NPC484983
0.5172	Remote Similarity	NPC168358
0.5169	Remote Similarity	NPC28637
0.5161	Remote Similarity	NPC479767
0.5149	Remote Similarity	NPC214621
0.5149	Remote Similarity	NPC34267
0.5149	Remote Similarity	NPC81042
0.5138	Remote Similarity	NPC484984
0.5132	Remote Similarity	NPC604356
0.5116	Remote Similarity	NPC310064
0.5062	Remote Similarity	NPC37074
0.506	Remote Similarity	NPC479473
0.506	Remote Similarity	NPC275721
0.506	Remote Similarity	NPC288416
0.506	Remote Similarity	NPC479468
0.506	Remote Similarity	NPC479474
0.5053	Remote Similarity	NPC300262
0.505	Remote Similarity	NPC484979

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476864 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4974
0.1-0.2	4072
0.2-0.3	90
0.3-0.4	12
0.4-0.5	2
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