NPASS Compound

Natural Product: NPC478703

Natural Product ID	NPC478703
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GWOWIVFDQIIGNT-QUAHOIDUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 97102 0 0 0 0 0 0 0 0999 V2000 9.7752 -2.0064 -1.0715 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6122 -0.6188 -0.9305 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5886 -0.0222 -0.2413 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6232 -0.7675 0.3838 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5671 -0.1950 1.0956 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4977 1.1822 1.1701 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4185 1.8015 1.9199 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1647 2.1061 1.1840 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3252 3.0713 0.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2465 2.7471 -0.8557 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6596 1.5340 -0.4905 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5587 1.1465 -1.0177 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5189 0.9219 0.5094 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8230 0.0878 1.5595 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1475 -1.0947 0.9229 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7806 -1.0875 0.6397 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1825 -2.1460 -0.0100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2463 -2.0745 -0.3642 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7116 -1.1095 -1.2168 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0983 -1.0231 -1.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5107 0.0761 -2.4374 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7052 1.3912 -1.8217 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9942 2.4990 -2.9045 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3467 3.6228 -2.0633 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6817 3.1584 -0.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7340 3.8601 0.2559 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9253 1.7047 -1.0081 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3456 0.8767 0.0963 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5489 1.3486 0.8736 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3063 2.0288 2.0406 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3212 2.4836 2.8413 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6196 2.2498 2.4587 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8773 1.5594 1.2703 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8378 1.1176 0.4931 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2096 1.3567 0.9337 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6536 0.6891 -0.2288 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6537 2.7107 3.2738 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8795 -1.9501 -0.9182 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4446 -2.9311 -0.0545 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0669 -2.9976 0.2377 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5457 -3.9495 1.0950 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2224 -3.8695 0.5642 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6028 -4.0582 0.4616 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9694 -3.2245 -0.3763 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3396 -3.2567 -0.1020 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9242 -2.1721 0.5560 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0913 -4.3445 -0.4777 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4650 -4.4080 -0.2584 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4211 -4.3173 -1.0326 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4608 1.9337 0.5464 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5172 1.3529 -0.1663 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4932 2.1186 -0.8007 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5454 3.5115 -0.8114 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8738 -2.5312 -1.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6939 -2.2601 -1.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9586 -2.4027 -0.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6958 -1.8459 0.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8676 -0.8812 1.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7447 2.7783 2.4029 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1195 1.1827 2.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4468 2.5723 1.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2590 4.1312 0.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2662 2.8652 -0.4811 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2963 0.2433 0.0651 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5167 -0.2363 2.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0053 0.7378 1.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2280 -0.2334 0.9462 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0604 -0.4057 -1.6716 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7051 0.1532 -3.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4257 -0.2566 -2.9756 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8186 1.7783 -1.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 2.6906 -3.4956 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9043 2.2379 -3.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7791 1.6625 -1.8232 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5498 0.6836 0.8259 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7797 -0.0913 -0.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2937 2.2584 2.4120 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1038 3.0242 3.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0341 0.5763 -0.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6596 1.0445 -0.5571 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9811 0.9433 -1.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6127 -0.4118 -0.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6295 2.5781 2.9562 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9506 -1.9461 -1.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9040 -4.8859 1.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0274 -3.3936 -0.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0375 -3.8226 1.4616 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7623 -5.1370 0.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0055 -2.1879 0.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9955 -5.1673 -0.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6939 -4.6978 0.7941 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0059 -3.4350 -0.4687 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6656 -5.2363 -0.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4678 3.0214 0.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0171 3.9402 0.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1644 3.8272 -1.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5076 3.9117 -0.9735 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 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 32 37 1 0 20 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 39 42 1 0 42 43 1 0 17 44 2 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 1 0 44 49 1 0 6 50 1 0 50 51 2 0 51 52 1 0 52 53 1 0 51 3 1 0 13 8 1 0 46 15 1 0 40 18 1 0 27 22 1 0 34 29 1 0 1 54 1 0 1 55 1 0 1 56 1 0 4 57 1 0 5 58 1 0 7 59 1 0 7 60 1 0 8 61 1 1 9 62 1 0 9 63 1 0 13 64 1 6 14 65 1 0 14 66 1 0 16 67 1 0 19 68 1 0 21 69 1 0 21 70 1 0 22 71 1 1 23 72 1 0 23 73 1 0 27 74 1 6 28 75 1 0 28 76 1 0 30 77 1 0 31 78 1 0 34 79 1 0 36 80 1 0 36 81 1 0 36 82 1 0 37 83 1 0 38 84 1 0 41 85 1 0 43 86 1 0 43 87 1 0 43 88 1 0 46 89 1 0 48 90 1 0 48 91 1 0 48 92 1 0 49 93 1 0 50 94 1 0 53 95 1 0 53 96 1 0 53 97 1 0 M END

Standard InCHIKey	GWOWIVFDQIIGNT-QUAHOIDUSA-N
Standard InCHI	InChI=1S/C41H44O12/c1-47-33-9-7-22(17-35(33)49-3)10-26-20-52-41(46)29(26)13-25-15-31(39(44)37(19-25)51-5)30-14-24(18-36(50-4)38(30)43)11-27-21-53-40(45)28(27)12-23-6-8-32(42)34(16-23)48-2/h6-9,14-19,26-29,42-44H,10-13,20-21H2,1-5H3/t26-,27-,28+,29+/m0/s1
SMILES	COc1ccc(C[C@H]2COC(=O)[C@@H]2Cc2cc(c3cc(C[C@H]4COC(=O)[C@@H]4Cc4ccc(c(c4)OC)O)cc(c3O)OC)c(c(c2)OC)O)cc1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	728.28	Volume:	734.925 ? Van der Waals volume.
Dense:	0.991	LogP:	3.235 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.837 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.43 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	36.0
TPSA:	159.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.388	Fsp³:	0.366
MCE-18:	122.143 ? 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:	0.972	Fluc inhibitor:	0.219 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.14 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.429 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.264	Promiscuous compounds:	0.202

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.236	MDCK Permeability:	-4.809
Pgp-inhibitor:	0.607	Pgp-substrate:	0.059
PAMPA:	0.003 ? 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):	0.004
20% Bioavailability (F20%):	0.92	30% Bioavailability (F30%):	0.506
50% Bioavailability (F50%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	97.748%	Volume Distribution (VD):	-0.342
Fu:	1.803% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.017
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

2.943

Half-life (T1/2):

2.874

ADMET: Toxicity

hERG Blockers:	0.245	hERG Blockers (10um):	0.708
Human Hepatotoxicity (H-HT):	0.997	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.861	Rat Oral Acute Toxicity:	0.447
Maximum Recommended Daily Dose:	0.968	Skin Sensitization:	0.936
Carcinogencity:	0.673	Eye Corrosion:	0.0
Eye Irritation:	0.131	Respiratory Toxicity:	0.263
Drug-induced Neurotoxicity:	0.81	Ototoxicity:	0.972
Hematotoxicity:	0.837	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.722
A549 Cytotoxicity:	0.953	Hek293 Cytotoxicity:	0.934
BCF:	1.089 ? 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:	4.685 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.605 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.363 ? 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
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	flower	n.a.	PMID[15481244]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30676026]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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
Ratio CC50/IC50	1
CC50	1

Activity Type	# Activity
Cell line	1
Organism	1
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
NPT165	Cell line	HeLa	Homo sapiens	CC50	>	50000.0	nM	PMID[30676026]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	IC50	=	45700.0	nM	PMID[30676026]
NPT2	Others	Unspecified	n.a.	Ratio CC50/IC50	>	1.1	n.a.	PMID[30676026]

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 NPC478703 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	19631
0.1-0.2	26550
0.2-0.3	3160
0.3-0.4	395
0.4-0.5	67
0.5-0.6	34
0.6-0.7	8
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478704
0.8448	Intermediate Similarity	NPC300776
0.8448	Intermediate Similarity	NPC176814
0.8448	Intermediate Similarity	NPC4982
0.8448	Intermediate Similarity	NPC606629
0.7414	Intermediate Similarity	NPC68779
0.7414	Intermediate Similarity	NPC108598
0.7258	Intermediate Similarity	NPC106920
0.7258	Intermediate Similarity	NPC15811
0.7231	Intermediate Similarity	NPC282291
0.7231	Intermediate Similarity	NPC166137
0.6984	Remote Similarity	NPC5310
0.6935	Remote Similarity	NPC273657
0.6618	Remote Similarity	NPC216223
0.6552	Remote Similarity	NPC223807
0.6154	Remote Similarity	NPC299706
0.6154	Remote Similarity	NPC115466
0.6154	Remote Similarity	NPC61604
0.6129	Remote Similarity	NPC211386
0.5972	Remote Similarity	NPC478705
0.5942	Remote Similarity	NPC145569
0.5846	Remote Similarity	NPC205915
0.5634	Remote Similarity	NPC487679
0.5634	Remote Similarity	NPC487678
0.5588	Remote Similarity	NPC102908
0.5538	Remote Similarity	NPC487680
0.5507	Remote Similarity	NPC110699
0.5507	Remote Similarity	NPC106055
0.5493	Remote Similarity	NPC31751
0.5484	Remote Similarity	NPC227217
0.5484	Remote Similarity	NPC117780
0.5429	Remote Similarity	NPC100675
0.5429	Remote Similarity	NPC601691
0.5352	Remote Similarity	NPC485282
0.5352	Remote Similarity	NPC485283
0.5352	Remote Similarity	NPC485281
0.5312	Remote Similarity	NPC607444
0.5231	Remote Similarity	NPC110958
0.5231	Remote Similarity	NPC19890
0.5217	Remote Similarity	NPC176586
0.5217	Remote Similarity	NPC210354
0.5211	Remote Similarity	NPC293757
0.5211	Remote Similarity	NPC668
0.5181	Remote Similarity	NPC245615
0.5161	Remote Similarity	NPC31344
0.5161	Remote Similarity	NPC317769
0.5161	Remote Similarity	NPC72796
0.5143	Remote Similarity	NPC191158
0.5143	Remote Similarity	NPC177644
0.5139	Remote Similarity	NPC610284
0.5128	Remote Similarity	NPC158635
0.5128	Remote Similarity	NPC229882
0.5067	Remote Similarity	NPC120852

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3981
0.1-0.2	4989
0.2-0.3	174
0.3-0.4	5
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