NPASS Compound

Natural Product: NPC238338

Natural Product ID	NPC238338
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HNKHXYXGMFUHCQ-IGBOVQOXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10629072
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 99104 0 0 0 0 0 0 0 0999 V2000 -5.6249 -2.2408 2.7575 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8478 -2.9504 1.6754 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7343 -4.0018 1.0371 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8197 -3.7878 -0.4579 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1395 -2.3424 -0.7739 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2678 -1.3811 0.0329 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3145 -2.1140 0.7261 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6836 -0.4828 -0.8289 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0203 0.8306 -0.6109 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7037 1.3248 -1.8870 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7055 0.9947 -3.0050 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3535 1.5862 -2.6448 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2767 0.5323 -2.5618 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4300 2.3935 -1.5176 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8094 1.7096 -0.3641 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1806 2.6479 0.5670 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4751 2.6681 1.7104 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0052 3.0455 1.6131 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8291 4.5051 1.3764 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2575 4.8145 0.0460 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3105 3.8115 -0.5351 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0131 2.7691 0.5659 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9124 1.8399 0.1240 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1975 1.6987 0.6059 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6815 2.5206 1.5940 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9815 2.3690 2.0722 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7671 1.3696 1.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3223 0.5214 0.5304 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0260 0.7030 0.0817 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0762 -0.4183 0.0208 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3370 -0.6565 0.3987 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0657 -1.7306 -0.2483 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3997 -1.9510 -0.1492 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0281 -3.0418 -0.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3012 -3.9347 -1.5154 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9443 -3.7366 -1.6356 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3434 -2.6561 -1.0135 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1546 -4.6154 -2.3816 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8812 -5.0387 -2.1572 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2775 -5.2285 -2.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8066 0.1607 1.3788 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0503 1.1845 1.9636 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5087 1.9187 2.8590 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0950 0.0205 1.8775 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3097 -0.8017 3.0276 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4930 3.1958 3.0779 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2657 2.1994 0.8225 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8419 4.4006 -0.9849 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2483 5.1839 -0.8826 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9741 5.0269 2.3678 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1945 1.4531 -4.2047 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8645 0.6246 -2.1357 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4651 -2.0428 -0.5472 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8420 -4.5812 -0.9734 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2301 -5.2459 1.3346 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5682 -1.8027 2.3754 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 -1.5516 3.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9327 -3.0468 3.4865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9804 -3.4376 2.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7808 -3.9212 1.4368 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8694 -4.0933 -0.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9192 -2.2042 -1.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9088 -0.7809 0.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7149 0.8788 0.2507 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8333 2.4081 -1.7818 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6240 -0.1038 -3.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0889 2.2600 -3.4886 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3242 0.9652 -2.9847 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5824 -0.3006 -3.2238 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0296 0.2276 -1.5411 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9973 1.0878 0.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5017 1.6376 2.1752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9934 3.3263 2.4518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6230 2.8454 2.6739 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8038 5.0650 1.4979 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6510 5.7692 0.1676 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8367 3.3016 -1.3721 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2742 3.3683 1.4449 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1101 3.3206 2.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6149 0.0578 -0.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0447 -1.2808 0.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0815 -3.2022 -0.6844 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2801 -2.4837 -1.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3778 -5.5887 -2.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7556 -4.3343 -2.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6027 -5.2277 -0.9593 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5913 -6.1607 -2.5265 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7056 -0.3613 3.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3569 -0.7690 3.3413 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0161 -1.8245 2.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8175 3.7529 3.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7361 4.6741 -1.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6073 6.0796 -0.6744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1568 4.6376 3.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7562 2.3434 -4.3749 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6624 0.9825 -1.7032 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9579 -2.1096 -1.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7237 -4.1391 -0.8712 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8628 -5.3091 2.2582 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 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 1 0 23 24 1 0 24 25 2 0 25 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 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 35 39 1 0 39 40 1 0 31 41 2 0 41 42 1 0 42 43 2 0 41 44 1 0 44 45 1 0 26 46 1 0 22 47 1 0 21 48 1 0 20 49 1 0 19 50 1 0 11 51 1 0 10 52 1 0 5 53 1 0 4 54 1 0 3 55 1 0 7 2 1 0 15 9 1 0 47 18 1 0 29 24 1 0 37 32 1 0 42 27 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 1 3 60 1 1 4 61 1 6 5 62 1 6 6 63 1 1 9 64 1 1 10 65 1 1 11 66 1 6 12 67 1 6 13 68 1 0 13 69 1 0 13 70 1 0 15 71 1 1 17 72 1 0 17 73 1 0 18 74 1 1 19 75 1 6 20 76 1 1 21 77 1 6 22 78 1 1 25 79 1 0 29 80 1 0 33 81 1 0 34 82 1 0 37 83 1 0 38 84 1 0 40 85 1 0 40 86 1 0 40 87 1 0 45 88 1 0 45 89 1 0 45 90 1 0 46 91 1 0 48 92 1 0 49 93 1 0 50 94 1 0 51 95 1 0 52 96 1 0 53 97 1 0 54 98 1 0 55 99 1 0 M END

Standard InCHIKey	HNKHXYXGMFUHCQ-IGBOVQOXSA-N
Standard InCHI	InChI=1S/C35H44O20/c1-11-21(38)25(42)28(45)33(50-11)55-32-27(44)22(39)12(2)51-35(32)49-10-19-23(40)26(43)29(46)34(54-19)52-14-8-16(37)20-18(9-14)53-30(31(48-4)24(20)41)13-5-6-17(47-3)15(36)7-13/h5-9,11-12,19,21-23,25-29,32-40,42-46H,10H2,1-4H3/t11-,12-,19+,21-,22-,23+,25+,26-,27+,28+,29+,32+,33-,34+,35+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H]([C@H]([C@H](C)O[C@H]1OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc(c3c(c2)oc(c2ccc(c(c2)O)OC)c(c3=O)OC)O)O1)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	784.24	Volume:	717.29 ? Van der Waals volume.
Dense:	1.093	LogP:	-0.368 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.664 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.149 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	306.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.388	Fsp³:	0.571
MCE-18:	152.455 ? 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:	0
Colloidal aggregators:	0.608	Fluc inhibitor:	0.294 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.736 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.431 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.097	Promiscuous compounds:	0.438

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.361	MDCK Permeability:	-5.329
Pgp-inhibitor:	0.0	Pgp-substrate:	0.985
PAMPA:	1.0 ? 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):	0.926
20% Bioavailability (F20%):	0.025	30% Bioavailability (F30%):	0.872
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.167
Plasma Protein Binding (PPB):	78.336%	Volume Distribution (VD):	-0.227
Fu:	19.798% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.961
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.089
BSEP inhibitor:	0.005

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:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.879
HLM stability:	0.025 ? 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):

0.841

Half-life (T1/2):

6.042

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.17
Human Hepatotoxicity (H-HT):	0.265	Drug-induced Liver Injury (DILI):	0.952
AMES Toxicity:	0.916	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	0.979
Carcinogencity:	0.013	Eye Corrosion:	0.0
Eye Irritation:	0.017	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.988
Hematotoxicity:	0.133	Drug-induced Nephrotoxicity:	0.584
Genotoxicity:	0.167	RPMI-8226 Immunitoxicity:	0.337
A549 Cytotoxicity:	0.295	Hek293 Cytotoxicity:	0.275
BCF:	0.36 ? 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:	3.05 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.685 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.83 ? 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
NPO19496	Bidens leucantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090869]
NPO19496	Bidens leucantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19496	Bidens leucantha	Species	Asteraceae	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

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

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 NPC238338 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	20390
0.1-0.2	25411
0.2-0.3	3129
0.3-0.4	500
0.4-0.5	290
0.5-0.6	105
0.6-0.7	24
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7386	Intermediate Similarity	NPC611303
0.7368	Intermediate Similarity	NPC209296
0.701	Intermediate Similarity	NPC473327
0.69	Remote Similarity	NPC135358
0.6875	Remote Similarity	NPC186816
0.6667	Remote Similarity	NPC606657
0.66	Remote Similarity	NPC142142
0.6598	Remote Similarity	NPC22062
0.6598	Remote Similarity	NPC473634
0.6598	Remote Similarity	NPC138811
0.6571	Remote Similarity	NPC480441
0.6458	Remote Similarity	NPC251417
0.6415	Remote Similarity	NPC25523
0.6311	Remote Similarity	NPC470445
0.6273	Remote Similarity	NPC198199
0.6238	Remote Similarity	NPC470443
0.6237	Remote Similarity	NPC271692
0.6162	Remote Similarity	NPC67105
0.6106	Remote Similarity	NPC120952
0.61	Remote Similarity	NPC210073
0.6064	Remote Similarity	NPC46420
0.6058	Remote Similarity	NPC470447
0.6038	Remote Similarity	NPC14187
0.6019	Remote Similarity	NPC32641
0.6019	Remote Similarity	NPC256188
0.6	Remote Similarity	NPC44931
0.6	Remote Similarity	NPC227508
0.598	Remote Similarity	NPC126784
0.598	Remote Similarity	NPC240306
0.598	Remote Similarity	NPC241423
0.5957	Remote Similarity	NPC158674
0.5938	Remote Similarity	NPC219904
0.5905	Remote Similarity	NPC476472
0.5905	Remote Similarity	NPC294815
0.5905	Remote Similarity	NPC16194
0.5888	Remote Similarity	NPC244875
0.5865	Remote Similarity	NPC35119
0.5851	Remote Similarity	NPC249281
0.5833	Remote Similarity	NPC11468
0.5784	Remote Similarity	NPC203259
0.5784	Remote Similarity	NPC33054
0.5784	Remote Similarity	NPC176740
0.5784	Remote Similarity	NPC471725
0.5784	Remote Similarity	NPC134532
0.5784	Remote Similarity	NPC602582
0.5758	Remote Similarity	NPC276377
0.5729	Remote Similarity	NPC84362
0.5728	Remote Similarity	NPC473571
0.5728	Remote Similarity	NPC110941
0.5701	Remote Similarity	NPC287889
0.569	Remote Similarity	NPC209550
0.5686	Remote Similarity	NPC173582
0.5686	Remote Similarity	NPC265885
0.5686	Remote Similarity	NPC181465
0.5686	Remote Similarity	NPC215710
0.5686	Remote Similarity	NPC473438
0.5686	Remote Similarity	NPC253788
0.566	Remote Similarity	NPC486577
0.5657	Remote Similarity	NPC605784
0.5647	Remote Similarity	NPC270620
0.5625	Remote Similarity	NPC311850
0.5607	Remote Similarity	NPC475382
0.5607	Remote Similarity	NPC473073
0.5577	Remote Similarity	NPC204693
0.5566	Remote Similarity	NPC473623
0.5556	Remote Similarity	NPC22832
0.5556	Remote Similarity	NPC21666
0.5545	Remote Similarity	NPC89052
0.5545	Remote Similarity	NPC121703
0.5536	Remote Similarity	NPC473644
0.5534	Remote Similarity	NPC39834
0.5521	Remote Similarity	NPC289667
0.5514	Remote Similarity	NPC488089
0.55	Remote Similarity	NPC116458
0.55	Remote Similarity	NPC246943
0.5487	Remote Similarity	NPC277532
0.5481	Remote Similarity	NPC303913
0.5481	Remote Similarity	NPC150164
0.5478	Remote Similarity	NPC68592
0.5421	Remote Similarity	NPC122467
0.5421	Remote Similarity	NPC72016
0.5413	Remote Similarity	NPC298171
0.54	Remote Similarity	NPC486578
0.5357	Remote Similarity	NPC470451
0.5333	Remote Similarity	NPC65563
0.5333	Remote Similarity	NPC470949
0.5327	Remote Similarity	NPC12013
0.5327	Remote Similarity	NPC11432
0.5327	Remote Similarity	NPC477613
0.531	Remote Similarity	NPC173837
0.5306	Remote Similarity	NPC136042
0.53	Remote Similarity	NPC285197
0.5288	Remote Similarity	NPC187379
0.5273	Remote Similarity	NPC101636
0.5254	Remote Similarity	NPC470719
0.5248	Remote Similarity	NPC120099
0.5248	Remote Similarity	NPC609478
0.5238	Remote Similarity	NPC275454
0.5234	Remote Similarity	NPC46202
0.5234	Remote Similarity	NPC488073
0.5234	Remote Similarity	NPC64425
0.5234	Remote Similarity	NPC153755
0.5234	Remote Similarity	NPC488074
0.5214	Remote Similarity	NPC488086
0.5204	Remote Similarity	NPC238376
0.5185	Remote Similarity	NPC483414
0.5182	Remote Similarity	NPC195257
0.5182	Remote Similarity	NPC89127
0.5179	Remote Similarity	NPC470455
0.5169	Remote Similarity	NPC298666
0.5152	Remote Similarity	NPC297987
0.5143	Remote Similarity	NPC609888
0.5124	Remote Similarity	NPC175429
0.51	Remote Similarity	NPC27640
0.5096	Remote Similarity	NPC116864
0.5096	Remote Similarity	NPC244776
0.5096	Remote Similarity	NPC95866
0.5094	Remote Similarity	NPC67326
0.5093	Remote Similarity	NPC475366
0.5089	Remote Similarity	NPC470446
0.5089	Remote Similarity	NPC602448
0.5082	Remote Similarity	NPC262222
0.5051	Remote Similarity	NPC108831
0.5051	Remote Similarity	NPC19709
0.5051	Remote Similarity	NPC182634
0.505	Remote Similarity	NPC59534
0.5047	Remote Similarity	NPC156869
0.5046	Remote Similarity	NPC65711
0.5043	Remote Similarity	NPC292019
0.5043	Remote Similarity	NPC202908
0.5043	Remote Similarity	NPC488087
0.504	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 NPC238338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5227
0.1-0.2	3872
0.2-0.3	43
0.3-0.4	1
0.4-0.5	2
0.5-0.6	2
0.6-0.7	2
0.7-0.8	1
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
0.7368	Intermediate Similarity	NPD7054	Phase 4
0.6535	Remote Similarity	NPD7251	Phase 2
0.6442	Remote Similarity	NPD7808	Phase 3
0.5833	Remote Similarity	NPD7472	Pre-clinical
0.5784	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