NPASS Compound

Natural Product: NPC477628

Natural Product ID	NPC477628
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	apigenin-4''-O-(2''''-O-p-coumaroyl)-beta-D-glucopyranoside
IUPAC Name	[(2R,3S,4R,5R,6S)-2-[4-(5,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44583918
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-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 68 72 0 0 0 0 0 0 0 0999 V2000 7.8314 1.1146 3.3104 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1025 0.8441 3.7664 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8825 -0.0821 3.1126 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3409 -0.7067 2.0095 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0540 -0.4254 1.5570 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2734 0.4922 2.2001 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9261 0.8389 1.7917 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3033 0.3065 0.7530 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9286 0.7653 0.4651 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3719 1.6318 1.1838 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1972 0.2649 -0.6013 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8691 0.7131 -0.8727 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8678 1.2013 -2.3073 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8853 0.0311 -3.2628 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1270 -1.2763 -2.6047 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4283 -1.5331 -1.4680 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8802 -0.4344 -0.8218 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2348 -0.0299 -1.5676 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5413 0.0252 -1.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9341 -0.3399 0.0695 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2670 -0.2751 0.4319 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1944 0.1547 -0.4682 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8372 0.5285 -1.7366 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4959 0.4561 -2.0795 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5978 0.2038 -0.0261 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6134 0.6211 -0.8554 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9268 0.6465 -0.3797 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8651 1.0237 -1.1207 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1943 0.2550 0.9115 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4819 0.2600 1.4382 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7160 -0.1405 2.7427 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6540 -0.5486 3.5248 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3812 -0.5475 2.9859 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1353 -0.1488 1.6820 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9259 -0.1565 1.1967 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8758 -0.9536 4.8375 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5411 0.6680 0.6550 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7794 -2.3755 -3.6167 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4369 -2.2116 -4.8111 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9683 0.2684 -4.1414 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6556 1.8877 -2.5474 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1771 -0.3799 3.5497 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2352 1.8511 3.8451 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5192 1.3495 4.6455 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9662 -1.4381 1.4989 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6757 -0.9481 0.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3819 1.5935 2.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7946 -0.4237 0.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5496 1.4621 -0.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6951 1.8993 -2.4495 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9788 -0.0293 -3.8934 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2256 -1.4287 -2.3931 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6549 -0.7497 0.1996 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2331 -0.6899 0.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5621 -0.5674 1.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5439 0.8736 -2.4753 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2446 0.7615 -3.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4352 0.9324 -1.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7091 -0.1274 3.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5329 -0.8608 3.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7021 -1.5384 4.9868 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8806 1.6392 0.7046 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0074 -3.3779 -3.2116 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6718 -2.3695 -3.8100 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1972 -2.8247 -4.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7298 0.0917 -5.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7786 2.6897 -3.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9084 -0.4072 2.8656 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 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 22 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 32 36 1 0 30 37 1 0 15 38 1 0 38 39 1 0 14 40 1 0 13 41 1 0 3 42 1 0 6 1 1 0 17 12 1 0 24 19 1 0 35 25 1 0 34 29 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 7 47 1 0 8 48 1 0 12 49 1 1 13 50 1 1 14 51 1 6 15 52 1 1 17 53 1 1 20 54 1 0 21 55 1 0 23 56 1 0 24 57 1 0 26 58 1 0 31 59 1 0 33 60 1 0 36 61 1 0 37 62 1 0 38 63 1 0 38 64 1 0 39 65 1 0 40 66 1 0 41 67 1 0 42 68 1 0 M END

Standard InCHIKey	FITSQGVBTPBMCU-CMAQPADGSA-N
Standard InCHI	InChI=1S/C30H26O12/c31-14-24-27(37)28(38)29(42-25(36)10-3-15-1-6-17(32)7-2-15)30(41-24)39-19-8-4-16(5-9-19)22-13-21(35)26-20(34)11-18(33)12-23(26)40-22/h1-13,24,27-34,37-38H,14H2/b10-3+/t24-,27-,28+,29-,30-/m0/s1
SMILES	C1=CC(=CC=C1/C=C/C(=O)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2OC3=CC=C(C=C3)C4=CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.14	Volume:	555.862 ? Van der Waals volume.
Dense:	1.04	LogP:	2.083 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.86 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	196.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.138	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.104	Fsp³:	0.2
MCE-18:	101.611 ? 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:	0.927	Fluc inhibitor:	0.975 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.955 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.968 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.415	Promiscuous compounds:	0.54

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.354	MDCK Permeability:	-5.249
Pgp-inhibitor:	0.003	Pgp-substrate:	0.058
PAMPA:	0.918 ? 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):	0.183
20% Bioavailability (F20%):	0.879	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	92.84%	Volume Distribution (VD):	-0.142
Fu:	6.881% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.36
BSEP inhibitor:	0.802

ADMET: Metabolism

CYP1A2-inhibitor:	0.128	CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.016	CYP2C9-substrate:	0.408
CYP2D6-inhibitor:	0.262	CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.535 ? 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):

2.272

Half-life (T1/2):

2.254

ADMET: Toxicity

hERG Blockers:	0.074	hERG Blockers (10um):	0.409
Human Hepatotoxicity (H-HT):	0.531	Drug-induced Liver Injury (DILI):	0.958
AMES Toxicity:	0.834	Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.548	Skin Sensitization:	0.975
Carcinogencity:	0.282	Eye Corrosion:	0.0
Eye Irritation:	0.876	Respiratory Toxicity:	0.092
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.367
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.279
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.544	Hek293 Cytotoxicity:	0.898
BCF:	1.082 ? 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:	4.048 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.175 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.811 ? 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
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872152]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31994397]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	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	1
Ki	1

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT967	Individual protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	23950	nM	PMID[16872152]
NPT967	Individual protein	Xanthine dehydrogenase	Homo sapiens	Ki	=	14350	nM	PMID[16872152]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC477628 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	13643
0.1-0.2	31294
0.2-0.3	3791
0.3-0.4	786
0.4-0.5	264
0.5-0.6	57
0.6-0.7	17
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8202	Intermediate Similarity	NPC260504
0.8202	Intermediate Similarity	NPC89809
0.7841	Intermediate Similarity	NPC472992
0.75	Intermediate Similarity	NPC470712
0.7391	Intermediate Similarity	NPC472991
0.6947	Remote Similarity	NPC477629
0.6832	Remote Similarity	NPC470718
0.6635	Remote Similarity	NPC470713
0.6437	Remote Similarity	NPC143851
0.6311	Remote Similarity	NPC470715
0.63	Remote Similarity	NPC218161
0.6139	Remote Similarity	NPC483767
0.6139	Remote Similarity	NPC483769
0.6139	Remote Similarity	NPC483768
0.6139	Remote Similarity	NPC483766
0.6087	Remote Similarity	NPC80188
0.6061	Remote Similarity	NPC210961
0.6	Remote Similarity	NPC221288
0.6	Remote Similarity	NPC164704
0.6	Remote Similarity	NPC194836
0.6	Remote Similarity	NPC91493
0.6	Remote Similarity	NPC605081
0.5914	Remote Similarity	NPC224530
0.5842	Remote Similarity	NPC205824
0.5841	Remote Similarity	NPC199172
0.5769	Remote Similarity	NPC483765
0.5743	Remote Similarity	NPC139060
0.5676	Remote Similarity	NPC162394
0.5638	Remote Similarity	NPC191306
0.563	Remote Similarity	NPC249560
0.5588	Remote Similarity	NPC104883
0.5588	Remote Similarity	NPC488679
0.5534	Remote Similarity	NPC101399
0.5534	Remote Similarity	NPC217822
0.5534	Remote Similarity	NPC11847
0.5534	Remote Similarity	NPC198938
0.5521	Remote Similarity	NPC136761
0.5521	Remote Similarity	NPC309025
0.5495	Remote Similarity	NPC76047
0.5495	Remote Similarity	NPC295625
0.5487	Remote Similarity	NPC470720
0.5446	Remote Similarity	NPC122809
0.5431	Remote Similarity	NPC25946
0.5417	Remote Similarity	NPC601710
0.5398	Remote Similarity	NPC470717
0.5385	Remote Similarity	NPC35924
0.5385	Remote Similarity	NPC270675
0.5385	Remote Similarity	NPC195685
0.5361	Remote Similarity	NPC88023
0.5347	Remote Similarity	NPC65003
0.5254	Remote Similarity	NPC21359
0.5254	Remote Similarity	NPC460984
0.5244	Remote Similarity	NPC231772
0.5243	Remote Similarity	NPC61904
0.5234	Remote Similarity	NPC484301
0.5189	Remote Similarity	NPC85751
0.5189	Remote Similarity	NPC19240
0.5185	Remote Similarity	NPC96605
0.5185	Remote Similarity	NPC280642
0.5182	Remote Similarity	NPC473278
0.5179	Remote Similarity	NPC470716
0.5158	Remote Similarity	NPC149011
0.5152	Remote Similarity	NPC170052
0.5152	Remote Similarity	NPC135846
0.513	Remote Similarity	NPC470719
0.51	Remote Similarity	NPC4390
0.5096	Remote Similarity	NPC253521
0.5096	Remote Similarity	NPC113836
0.5093	Remote Similarity	NPC223426
0.5093	Remote Similarity	NPC472994
0.5052	Remote Similarity	NPC216496
0.505	Remote Similarity	NPC8856
0.5049	Remote Similarity	NPC304741
0.5047	Remote Similarity	NPC76831
0.5046	Remote Similarity	NPC478277
0.5046	Remote Similarity	NPC478276
0.5046	Remote Similarity	NPC478275
0.5046	Remote Similarity	NPC92815
0.5045	Remote Similarity	NPC477895

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477628 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4108
0.1-0.2	4951
0.2-0.3	79
0.3-0.4	11
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