NPASS Compound

Natural Product: NPC480796

Natural Product ID	NPC480796
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VXLLQWICTXGVKP-JHLKCIRISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21769760
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 73 77 0 0 0 0 0 0 0 0999 V2000 -10.0433 1.0711 -3.0041 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4943 0.9301 -1.6779 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6194 0.7785 -0.6250 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2355 0.7592 -0.8347 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3347 0.6096 0.1941 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8823 0.4775 1.4653 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2404 0.4954 1.6794 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1373 0.6452 0.6476 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5106 0.6650 0.8494 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8995 0.5837 0.0230 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2845 0.6949 -1.1294 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8183 0.6611 -1.2378 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3364 0.7747 -2.3906 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9993 0.5150 -0.1576 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6041 0.4739 -0.2522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1951 -0.7343 -1.0519 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8602 -1.9405 -0.4413 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2284 -2.2588 0.8752 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2426 -2.2907 0.7475 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8666 -1.1955 -0.0681 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1633 -0.0965 0.7329 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4013 0.4741 0.9942 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4658 1.5792 1.8485 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6822 2.1391 2.1041 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8637 1.6688 1.5592 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8318 0.5831 0.7151 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5731 0.0180 0.4620 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8970 0.0801 0.1623 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1182 0.5651 0.3582 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2436 -0.0758 -0.3112 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9516 -1.1744 -1.1254 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9377 -1.8554 -1.8044 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2512 -1.4579 -1.6902 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5867 -0.3847 -0.9026 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5538 0.2719 -0.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2827 -2.1266 -2.3661 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1998 1.6488 1.1929 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0797 2.2212 1.8083 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1757 3.2106 2.5672 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4225 2.2316 1.4655 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7734 3.2548 2.9628 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1596 -0.8636 -1.2010 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6493 -3.5420 0.2906 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6970 -1.4423 1.9009 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8820 -3.0406 -1.2808 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6898 2.1207 -3.1539 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2341 0.3703 -3.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9103 0.9510 -3.7101 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8706 0.8653 -1.8317 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1733 0.3570 2.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6207 0.3909 2.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1201 0.9846 0.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2645 0.4630 0.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8865 0.8147 -2.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1155 0.5031 0.7468 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3109 1.4292 -0.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6074 -0.6165 -2.0675 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9166 -1.6571 -0.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5679 -3.3012 1.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -2.1887 1.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8217 -1.6113 -0.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5303 1.9401 2.2703 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5842 -0.8361 -0.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9345 -1.5300 -1.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7154 -2.7035 -2.4332 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6235 -0.0426 -0.7901 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8456 1.1055 0.3707 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4385 -2.0316 -3.3628 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5203 3.2215 1.2175 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3669 4.1125 2.5811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2447 -4.0148 0.9313 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5308 -1.8093 2.7902 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5495 -2.8888 -1.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 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 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 29 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 24 41 1 0 20 42 1 0 19 43 1 0 18 44 1 0 17 45 1 0 8 3 1 0 42 16 1 0 27 22 1 0 35 30 1 0 38 25 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 6 50 1 0 7 51 1 0 9 52 1 0 10 53 1 0 11 54 1 0 15 55 1 0 15 56 1 0 16 57 1 6 17 58 1 1 18 59 1 1 19 60 1 1 20 61 1 6 23 62 1 0 27 63 1 0 31 64 1 0 32 65 1 0 34 66 1 0 35 67 1 0 36 68 1 0 40 69 1 0 41 70 1 0 43 71 1 0 44 72 1 0 45 73 1 0 M END

Standard InCHIKey	VXLLQWICTXGVKP-JHLKCIRISA-N
Standard InCHI	InChI=1S/C31H28O14/c1-41-20-10-14(2-8-18(20)33)3-9-23(35)42-13-22-25(36)27(38)29(40)31(45-22)43-17-11-19(34)24-21(12-17)44-30(28(39)26(24)37)15-4-6-16(32)7-5-15/h2-12,22,25,27,29,31-34,36,38-40H,13H2,1H3/b9-3+/t22-,25-,27+,29-,31-/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc(c3c(c2)oc(c2ccc(cc2)O)c(c3=O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.15	Volume:	590.739 ? Van der Waals volume.
Dense:	1.057	LogP:	1.391 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.562 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.86 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	32.0
TPSA:	225.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.222	Fsp³:	0.226
MCE-18:	107.684 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.793	Fluc inhibitor:	0.994 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.954 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.993 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.055	Promiscuous compounds:	0.597

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.372	MDCK Permeability:	-5.287
Pgp-inhibitor:	0.101	Pgp-substrate:	0.048
PAMPA:	0.934 ? 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):	0.607
20% Bioavailability (F20%):	0.569	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.052
Plasma Protein Binding (PPB):	90.441%	Volume Distribution (VD):	-0.199
Fu:	8.224% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.95
BSEP inhibitor:	0.81

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.593
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.544 ? 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):

2.148

Half-life (T1/2):

3.44

ADMET: Toxicity

hERG Blockers:	0.048	hERG Blockers (10um):	0.387
Human Hepatotoxicity (H-HT):	0.388	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.795	Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.401	Skin Sensitization:	0.976
Carcinogencity:	0.164	Eye Corrosion:	0.0
Eye Irritation:	0.605	Respiratory Toxicity:	0.044
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.439
Hematotoxicity:	0.025	Drug-induced Nephrotoxicity:	0.405
Genotoxicity:	0.914	RPMI-8226 Immunitoxicity:	0.186
A549 Cytotoxicity:	0.608	Hek293 Cytotoxicity:	0.733
BCF:	0.8 ? 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:	3.721 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.684 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.29 ? 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
NPO22334	Gnaphalium cheiranthifolium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7623048]
NPO40801	Buddleia coriacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7623048]
NPO40926	Scheelea princeps	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7623048]
NPO22334	Gnaphalium cheiranthifolium	Species	n.a.	n.a.	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
ID50	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
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	ID50	=	0.44	mM	PMID[7623048]

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 NPC480796 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	17077
0.1-0.2	27620
0.2-0.3	3881
0.3-0.4	912
0.4-0.5	270
0.5-0.6	69
0.6-0.7	21
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC80068
0.8333	Intermediate Similarity	NPC472993
0.7423	Intermediate Similarity	NPC270675
0.7423	Intermediate Similarity	NPC195685
0.7228	Intermediate Similarity	NPC599948
0.703	Intermediate Similarity	NPC472994
0.699	Remote Similarity	NPC470416
0.6635	Remote Similarity	NPC603856
0.6344	Remote Similarity	NPC108831
0.6344	Remote Similarity	NPC182634
0.6311	Remote Similarity	NPC139060
0.6286	Remote Similarity	NPC36138
0.6283	Remote Similarity	NPC470720
0.6277	Remote Similarity	NPC323593
0.6277	Remote Similarity	NPC203500
0.6239	Remote Similarity	NPC217520
0.6195	Remote Similarity	NPC470717
0.619	Remote Similarity	NPC85751
0.619	Remote Similarity	NPC19240
0.6162	Remote Similarity	NPC477848
0.614	Remote Similarity	NPC488079
0.614	Remote Similarity	NPC488078
0.6038	Remote Similarity	NPC188815
0.6038	Remote Similarity	NPC477629
0.6019	Remote Similarity	NPC214621
0.6019	Remote Similarity	NPC34267
0.6	Remote Similarity	NPC477895
0.5982	Remote Similarity	NPC139571
0.598	Remote Similarity	NPC67105
0.5926	Remote Similarity	NPC223426
0.59	Remote Similarity	NPC601586
0.5816	Remote Similarity	NPC471405
0.5798	Remote Similarity	NPC25946
0.5776	Remote Similarity	NPC471030
0.5739	Remote Similarity	NPC295625
0.5727	Remote Similarity	NPC81042
0.5714	Remote Similarity	NPC473278
0.57	Remote Similarity	NPC486578
0.567	Remote Similarity	NPC238376
0.5667	Remote Similarity	NPC199172
0.566	Remote Similarity	NPC64051
0.5641	Remote Similarity	NPC470719
0.5636	Remote Similarity	NPC135358
0.5612	Remote Similarity	NPC277205
0.5612	Remote Similarity	NPC37919
0.5603	Remote Similarity	NPC474093
0.5603	Remote Similarity	NPC104910
0.56	Remote Similarity	NPC285197
0.5536	Remote Similarity	NPC121703
0.5524	Remote Similarity	NPC275454
0.5524	Remote Similarity	NPC227508
0.5492	Remote Similarity	NPC21359
0.5492	Remote Similarity	NPC460984
0.5472	Remote Similarity	NPC233994
0.5463	Remote Similarity	NPC488364
0.5417	Remote Similarity	NPC291153
0.54	Remote Similarity	NPC291296
0.54	Remote Similarity	NPC10205
0.5392	Remote Similarity	NPC476869
0.5391	Remote Similarity	NPC164704
0.5385	Remote Similarity	NPC476865
0.5377	Remote Similarity	NPC44931
0.5347	Remote Similarity	NPC27942
0.5321	Remote Similarity	NPC211532
0.5294	Remote Similarity	NPC307938
0.5278	Remote Similarity	NPC186816
0.5273	Remote Similarity	NPC476620
0.5242	Remote Similarity	NPC35924
0.5238	Remote Similarity	NPC172807
0.5234	Remote Similarity	NPC11411
0.5229	Remote Similarity	NPC46202
0.5227	Remote Similarity	NPC143799
0.5189	Remote Similarity	NPC479767
0.514	Remote Similarity	NPC187379
0.5135	Remote Similarity	NPC209296
0.5135	Remote Similarity	NPC229409
0.5133	Remote Similarity	NPC101636
0.5133	Remote Similarity	NPC298171
0.5128	Remote Similarity	NPC470715
0.5098	Remote Similarity	NPC46420
0.5098	Remote Similarity	NPC84265
0.5093	Remote Similarity	NPC300262
0.5091	Remote Similarity	NPC153755
0.5089	Remote Similarity	NPC486577
0.5088	Remote Similarity	NPC470450
0.5051	Remote Similarity	NPC157898
0.505	Remote Similarity	NPC476405
0.5048	Remote Similarity	NPC488082
0.5048	Remote Similarity	NPC476868
0.5046	Remote Similarity	NPC22062
0.5046	Remote Similarity	NPC133984
0.5046	Remote Similarity	NPC473634
0.5046	Remote Similarity	NPC138811
0.5042	Remote Similarity	NPC470716
0.5041	Remote Similarity	NPC470713
0.5039	Remote Similarity	NPC473554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4022
0.1-0.2	5047
0.2-0.3	67
0.3-0.4	9
0.4-0.5	4
0.5-0.6	1
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
0.5135	Remote Similarity	NPD7054	Phase 4

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