NPASS Compound

Natural Product: NPC477629

Natural Product ID	NPC477629
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-(6''''-O-p-coumaroyl)-beta-D-glucopyranoside
IUPAC Name	[(2S,3R,4R,5S,6R)-6-[4-(5,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44583919
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 8.3685 2.1611 -1.7797 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6922 2.4205 -2.1046 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6934 2.0712 -1.2110 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3487 1.4715 -0.0146 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0020 1.2225 0.2849 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0074 1.5639 -0.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6073 1.3215 -0.3138 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1050 0.7674 0.7597 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6640 0.5609 0.9558 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8501 0.9244 0.0681 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1771 -0.0244 2.0937 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8198 -0.2650 2.3736 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1561 -1.1533 1.3753 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8019 -2.5370 1.2955 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1430 -3.2405 0.1535 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6643 -3.1347 0.0939 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0779 -1.8706 0.6681 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8397 -1.3496 1.7089 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1743 -2.1777 1.1950 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3967 -1.6315 0.8890 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5865 -0.6382 -0.0352 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8579 -0.1131 -0.3117 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9772 -0.5946 0.3554 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8085 -1.5865 1.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5427 -2.0963 1.5447 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2695 -0.0237 0.0400 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4084 -0.4603 0.6607 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6447 0.1108 0.3347 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7067 -0.2759 0.8938 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7089 1.1076 -0.6073 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9256 1.7005 -0.9576 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9627 2.6880 -1.8955 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7898 3.1003 -2.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5972 2.5088 -2.1457 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5173 1.4982 -1.1934 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3906 0.9429 -0.8631 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8268 4.1216 -3.4690 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0668 1.2423 -0.3163 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2924 -3.1470 -1.2718 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5272 -4.5976 0.1127 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1620 -2.4352 1.0072 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0279 2.3273 -1.5273 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5984 2.4429 -2.4951 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9929 2.8891 -3.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0817 1.1844 0.7048 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7297 0.7546 1.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8558 1.6230 -1.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7797 0.4472 1.5364 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2227 0.6518 2.4639 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7808 -0.7760 3.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2218 -0.7283 0.3398 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6239 -3.0602 2.2501 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5820 -2.8009 -0.7900 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1566 -4.0301 0.5275 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0237 -1.0732 -0.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7455 -0.2383 -0.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9994 0.6639 -1.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6658 -1.9882 1.8242 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4315 -2.8814 2.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4426 -1.2284 1.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9082 3.1378 -2.1570 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6795 2.8223 -2.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7505 5.0652 -3.0802 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2152 1.5862 0.6319 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3025 -2.2305 -1.6452 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0178 -5.1189 0.8007 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6503 -2.8570 1.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3963 3.2625 -1.6371 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 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 33 37 1 0 31 38 1 0 16 39 1 0 15 40 1 0 14 41 1 0 3 42 1 0 6 1 1 0 18 13 1 0 25 20 1 0 36 26 1 0 35 30 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 0 12 50 1 0 13 51 1 6 14 52 1 1 15 53 1 6 16 54 1 1 17 55 1 6 21 56 1 0 22 57 1 0 24 58 1 0 25 59 1 0 27 60 1 0 32 61 1 0 34 62 1 0 37 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	HIVMDOSHUCWOJU-CMAQPADGSA-N
Standard InCHI	InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-8-4-16(5-9-19)22-13-21(34)26-20(33)11-18(32)12-23(26)41-22/h1-13,24,27-33,36-38H,14H2/b10-3+/t24-,27-,28+,29-,30-/m0/s1
SMILES	C1=CC(=CC=C1/C=C/C(=O)OC[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)OC3=CC=C(C=C3)C4=CC(=O)C5=C(C=C(C=C5O4)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.14	Volume:	555.862 ? Van der Waals volume.
Dense:	1.04	LogP:	2.256 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.056 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.528 ? 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:	4.064	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:	0.893	Fluc inhibitor:	0.977 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.946 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.995 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.162	Promiscuous compounds:	0.595

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.232	MDCK Permeability:	-5.261
Pgp-inhibitor:	0.003	Pgp-substrate:	0.099
PAMPA:	0.957 ? 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):	0.075
20% Bioavailability (F20%):	0.903	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.008
Plasma Protein Binding (PPB):	96.08%	Volume Distribution (VD):	-0.213
Fu:	3.88% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.046
BSEP inhibitor:	0.798

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.29
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.97
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.98
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.682 ? 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):

2.144

Half-life (T1/2):

3.19

ADMET: Toxicity

hERG Blockers:	0.097	hERG Blockers (10um):	0.379
Human Hepatotoxicity (H-HT):	0.577	Drug-induced Liver Injury (DILI):	0.981
AMES Toxicity:	0.946	Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.639	Skin Sensitization:	0.989
Carcinogencity:	0.407	Eye Corrosion:	0.0
Eye Irritation:	0.597	Respiratory Toxicity:	0.032
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.603
Hematotoxicity:	0.034	Drug-induced Nephrotoxicity:	0.275
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.132
A549 Cytotoxicity:	0.53	Hek293 Cytotoxicity:	0.934
BCF:	1.01 ? 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:	3.991 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.99 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.692 ? 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

Activity Type	# Activity
Individual protein	1

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	>	100000	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 NPC477629 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	14919
0.1-0.2	29934
0.2-0.3	3690
0.3-0.4	827
0.4-0.5	352
0.5-0.6	104
0.6-0.7	14
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
0.8132	Intermediate Similarity	NPC260504
0.8132	Intermediate Similarity	NPC89809
0.7912	Intermediate Similarity	NPC270675
0.7912	Intermediate Similarity	NPC195685
0.7634	Intermediate Similarity	NPC85751
0.7634	Intermediate Similarity	NPC19240
0.7474	Intermediate Similarity	NPC223426
0.7474	Intermediate Similarity	NPC472994
0.7347	Intermediate Similarity	NPC477895
0.7172	Intermediate Similarity	NPC472993
0.71	Intermediate Similarity	NPC217520
0.7041	Intermediate Similarity	NPC214621
0.7041	Intermediate Similarity	NPC34267
0.6947	Remote Similarity	NPC477628
0.6869	Remote Similarity	NPC81042
0.6735	Remote Similarity	NPC80068
0.6591	Remote Similarity	NPC143851
0.65	Remote Similarity	NPC36138
0.6476	Remote Similarity	NPC139571
0.6322	Remote Similarity	NPC291153
0.6275	Remote Similarity	NPC218161
0.6162	Remote Similarity	NPC470125
0.6132	Remote Similarity	NPC470712
0.6058	Remote Similarity	NPC96605
0.6058	Remote Similarity	NPC280642
0.6038	Remote Similarity	NPC480796
0.6038	Remote Similarity	NPC473278
0.5943	Remote Similarity	NPC470416
0.5882	Remote Similarity	NPC476620
0.5876	Remote Similarity	NPC4390
0.5876	Remote Similarity	NPC211594
0.5849	Remote Similarity	NPC599948
0.5842	Remote Similarity	NPC64051
0.5789	Remote Similarity	NPC191306
0.5758	Remote Similarity	NPC187379
0.5743	Remote Similarity	NPC129264
0.5714	Remote Similarity	NPC116864
0.5714	Remote Similarity	NPC244776
0.5714	Remote Similarity	NPC172807
0.569	Remote Similarity	NPC25946
0.5686	Remote Similarity	NPC46202
0.567	Remote Similarity	NPC309025
0.5625	Remote Similarity	NPC474093
0.5625	Remote Similarity	NPC104910
0.5607	Remote Similarity	NPC603856
0.5586	Remote Similarity	NPC470718
0.5579	Remote Similarity	NPC10205
0.5577	Remote Similarity	NPC104883
0.5577	Remote Similarity	NPC488679
0.5567	Remote Similarity	NPC601710
0.5545	Remote Similarity	NPC44931
0.5543	Remote Similarity	NPC157898
0.5534	Remote Similarity	NPC153755
0.5526	Remote Similarity	NPC162394
0.5526	Remote Similarity	NPC471030
0.551	Remote Similarity	NPC88023
0.5508	Remote Similarity	NPC21359
0.5508	Remote Similarity	NPC460984
0.549	Remote Similarity	NPC22062
0.549	Remote Similarity	NPC473634
0.549	Remote Similarity	NPC138811
0.5439	Remote Similarity	NPC470713
0.5431	Remote Similarity	NPC241781
0.5429	Remote Similarity	NPC229409
0.5391	Remote Similarity	NPC156785
0.5385	Remote Similarity	NPC472992
0.5361	Remote Similarity	NPC27942
0.5294	Remote Similarity	NPC471079
0.5294	Remote Similarity	NPC609888
0.5289	Remote Similarity	NPC473554
0.5288	Remote Similarity	NPC204693
0.5285	Remote Similarity	NPC487502
0.5283	Remote Similarity	NPC210961
0.5283	Remote Similarity	NPC473623
0.5283	Remote Similarity	NPC270448
0.5278	Remote Similarity	NPC101636
0.5278	Remote Similarity	NPC298171
0.5278	Remote Similarity	NPC287889
0.5258	Remote Similarity	NPC181712
0.5243	Remote Similarity	NPC173582
0.5243	Remote Similarity	NPC265885
0.5243	Remote Similarity	NPC181465
0.5243	Remote Similarity	NPC215710
0.5243	Remote Similarity	NPC473438
0.5243	Remote Similarity	NPC253788
0.5234	Remote Similarity	NPC488089
0.5229	Remote Similarity	NPC483767
0.5229	Remote Similarity	NPC483769
0.5229	Remote Similarity	NPC483768
0.5229	Remote Similarity	NPC483766
0.5204	Remote Similarity	NPC198324
0.5196	Remote Similarity	NPC254540
0.5182	Remote Similarity	NPC478277
0.5182	Remote Similarity	NPC478276
0.5182	Remote Similarity	NPC478275
0.5182	Remote Similarity	NPC92815
0.5155	Remote Similarity	NPC64305
0.5152	Remote Similarity	NPC204937
0.514	Remote Similarity	NPC37668
0.514	Remote Similarity	NPC483707
0.514	Remote Similarity	NPC209296
0.514	Remote Similarity	NPC473327
0.5133	Remote Similarity	NPC470715
0.5128	Remote Similarity	NPC474522
0.5104	Remote Similarity	NPC331652
0.51	Remote Similarity	NPC476869
0.51	Remote Similarity	NPC476866
0.5096	Remote Similarity	NPC67326
0.5093	Remote Similarity	NPC205824
0.5093	Remote Similarity	NPC221288
0.5093	Remote Similarity	NPC194836
0.5093	Remote Similarity	NPC472991
0.5093	Remote Similarity	NPC91493
0.5093	Remote Similarity	NPC605081
0.5085	Remote Similarity	NPC488079
0.5085	Remote Similarity	NPC488078
0.5059	Remote Similarity	NPC231772
0.5052	Remote Similarity	NPC39360
0.5052	Remote Similarity	NPC29763
0.5052	Remote Similarity	NPC210003
0.5051	Remote Similarity	NPC476867
0.5049	Remote Similarity	NPC472876
0.5048	Remote Similarity	NPC203259
0.5048	Remote Similarity	NPC33054
0.5048	Remote Similarity	NPC210073
0.5048	Remote Similarity	NPC176740
0.5048	Remote Similarity	NPC471725
0.5048	Remote Similarity	NPC134532
0.5048	Remote Similarity	NPC156869
0.5048	Remote Similarity	NPC602582
0.5043	Remote Similarity	NPC470716

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3943
0.1-0.2	5115
0.2-0.3	77
0.3-0.4	11
0.4-0.5	2
0.5-0.6	2
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
0.514	Remote Similarity	NPD7054	Phase 4
0.5048	Remote Similarity	NPD6797	Phase 2

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