NPASS Compound

Natural Product: NPC471493

Natural Product ID	NPC471493
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CFXLQLVVACEBGI-VHMPTJLLSA-N
IUPAC Name	n.a.
Synonyms	7Beta-D-Xylosylbaccatin Iii
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL252932
PubChem CID	44445497
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 2.3275 5.2681 2.1986 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6838 4.3631 1.1796 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9609 4.5085 -0.0449 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7928 3.3741 1.5636 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.5433 0.5777 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2305 2.3704 0.7321 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8794 3.0926 -0.1775 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2133 4.3078 -0.7007 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2199 2.6207 -0.6396 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2729 2.8627 -2.0373 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3740 1.1282 -0.4740 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6666 0.4988 0.6652 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1215 1.5439 1.6181 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5306 1.0823 2.8673 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3282 2.3999 2.0170 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6546 -0.1384 1.4699 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.6167 0.3065 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5966 -0.3493 -0.6070 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7227 -0.1723 0.1802 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8720 1.1817 0.7481 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7708 1.2164 1.5774 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8230 -1.1337 1.3538 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9043 -0.5555 -0.6986 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0567 -0.4843 0.0657 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0887 0.1964 -0.5554 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4891 1.2506 0.2099 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4519 0.9834 1.1440 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4813 -0.4478 1.6194 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6039 -1.4323 0.4720 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2993 -0.6787 -0.7925 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2228 -1.4552 -1.9197 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9356 -1.8914 0.3518 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4385 -0.7454 2.4739 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7324 -2.0816 -0.9174 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5401 -2.3544 -1.6909 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3804 -1.1156 -1.8540 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2466 -2.2537 -2.2165 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5798 -2.9817 -1.2005 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1372 -0.4575 -2.9806 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3349 0.5527 -3.7221 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4262 1.0702 -3.4562 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4171 1.1157 -4.9069 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5490 -1.7214 0.0398 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8057 -2.7481 0.9517 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2238 -2.6513 2.0688 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6805 -3.8742 0.6719 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8805 -4.8603 1.6149 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7064 -5.9414 1.3840 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3725 -6.0757 0.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1811 -5.0970 -0.7698 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3411 -4.0021 -0.5286 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 5.0707 2.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9157 5.0586 3.1851 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1955 6.3412 1.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5677 2.8533 -0.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8982 4.9888 0.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4983 4.1476 -1.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0549 4.8819 -1.1959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0657 3.2200 -0.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5464 3.7972 -2.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4985 0.9835 -0.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1122 0.5908 -1.4039 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4769 1.3181 3.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7111 0.0232 3.0404 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0627 1.5922 3.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2792 2.0001 1.6616 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1642 3.4768 1.8296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4632 2.3807 3.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5184 -0.1626 1.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2938 -0.8806 1.3476 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7549 0.6843 -1.0168 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5524 -0.6748 2.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9277 -1.3604 1.5272 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3607 -2.1057 1.1870 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9639 -0.0399 -1.6478 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7717 0.5625 -1.5505 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4819 1.3142 0.8391 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2194 1.6036 2.0490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4267 -0.5467 2.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9276 -2.2836 0.6419 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1614 0.0349 -0.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3792 -0.8606 -2.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2091 -1.9273 -0.6027 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6838 -1.4695 3.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9233 -2.6088 0.0067 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6388 -2.3155 -1.5655 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7359 -2.7851 -2.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3021 -2.1958 -2.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8833 -2.6987 -3.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5169 0.9712 -4.7353 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1375 2.1507 -5.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1525 0.4540 -5.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3517 -4.7457 2.5593 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8579 -6.7074 2.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0278 -6.9138 -0.0296 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6852 -5.1721 -1.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2157 -3.2597 -1.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 7 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 12 16 1 1 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 19 22 1 1 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 23 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 6 39 40 1 0 40 41 2 0 40 42 1 0 17 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 20 5 1 0 30 25 1 0 38 35 1 0 51 46 1 0 13 6 1 0 36 18 1 0 1 52 1 0 1 53 1 0 1 54 1 0 5 55 1 6 8 56 1 0 8 57 1 0 8 58 1 0 9 59 1 1 10 60 1 0 11 61 1 0 11 62 1 0 14 63 1 0 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 17 70 1 1 18 71 1 6 22 72 1 0 22 73 1 0 22 74 1 0 23 75 1 6 25 76 1 6 27 77 1 0 27 78 1 0 28 79 1 1 29 80 1 1 30 81 1 6 31 82 1 0 32 83 1 0 33 84 1 0 34 85 1 0 34 86 1 0 35 87 1 6 37 88 1 0 37 89 1 0 42 90 1 0 42 91 1 0 42 92 1 0 47 93 1 0 48 94 1 0 49 95 1 0 50 96 1 0 51 97 1 0 M END

Standard InCHIKey	CFXLQLVVACEBGI-VHMPTJLLSA-N
Standard InCHI	InChI=1S/C36H46O15/c1-16-20(39)13-36(45)30(50-31(44)19-10-8-7-9-11-19)28-34(6,29(43)27(48-17(2)37)24(16)33(36,4)5)22(12-23-35(28,15-47-23)51-18(3)38)49-32-26(42)25(41)21(40)14-46-32/h7-11,20-23,25-28,30,32,39-42,45H,12-15H2,1-6H3/t20-,21+,22-,23+,25-,26+,27+,28-,30-,32+,34+,35-,36+/m0/s1
SMILES	CC(=O)O[C@@H]1C2=C(C)[C@@H](O)C[C@@](C2(C)C)(O)[C@H]([C@H]2[C@@](C1=O)(C)[C@@H](O[C@H]1OC[C@H]([C@@H]([C@H]1O)O)O)C[C@@H]1[C@]2(CO1)OC(=O)C)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	718.28	Volume:	690.635 ? Van der Waals volume.
Dense:	1.04	LogP:	1.033 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.396 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.002 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	224.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.15	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.039	Fsp³:	0.667
MCE-18:	169.2 ? 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:	0.737	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.046	Promiscuous compounds:	0.211

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.609	MDCK Permeability:	-4.889
Pgp-inhibitor:	0.022	Pgp-substrate:	1.0
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):	0.0
20% Bioavailability (F20%):	0.793	30% Bioavailability (F30%):	0.898
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.979
Plasma Protein Binding (PPB):	70.066%	Volume Distribution (VD):	-0.449
Fu:	26.438% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.001
BSEP inhibitor:	0.842

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	0.036
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.876 ? 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):

3.192

Half-life (T1/2):

3.982

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.205
Human Hepatotoxicity (H-HT):	0.377	Drug-induced Liver Injury (DILI):	0.917
AMES Toxicity:	0.869	Rat Oral Acute Toxicity:	0.367
Maximum Recommended Daily Dose:	0.77	Skin Sensitization:	1.0
Carcinogencity:	0.207	Eye Corrosion:	0.0
Eye Irritation:	0.01	Respiratory Toxicity:	0.073
Drug-induced Neurotoxicity:	0.631	Ototoxicity:	0.845
Hematotoxicity:	0.719	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.527
A549 Cytotoxicity:	0.514	Hek293 Cytotoxicity:	0.316
BCF:	0.428 ? 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:	3.185 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.939 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.954 ? 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
NPO32766	luteibacter sp.	Species	Rhodanobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[18001087]

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	5

Activity Type	# Activity
Cell line	5

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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	<	10000.0	nM	DrugMatrix in vitro pharmacology data
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	<	10000.0	nM	DrugMatrix in vitro pharmacology data
NPT547	Cell line	BGC-823	Homo sapiens	IC50	<	10000.0	nM	DrugMatrix in vivo data: Pathology
NPT81	Cell line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[15165132]
NPT179	Cell line	A2780	Homo sapiens	IC50	<	10000.0	nM	PMID[17346076]

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 NPC471493 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	9827
0.1-0.2	35771
0.2-0.3	3915
0.3-0.4	281
0.4-0.5	43
0.5-0.6	13
0.6-0.7	7
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	Natural Product ID
0.6981	Remote Similarity	NPC116862
0.6852	Remote Similarity	NPC472391
0.6789	Remote Similarity	NPC479185
0.6778	Remote Similarity	NPC155329
0.6778	Remote Similarity	NPC114357
0.6667	Remote Similarity	NPC479184
0.663	Remote Similarity	NPC259144
0.5914	Remote Similarity	NPC38696
0.5841	Remote Similarity	NPC289383
0.5826	Remote Similarity	NPC479173
0.569	Remote Similarity	NPC479186
0.5652	Remote Similarity	NPC472392
0.5648	Remote Similarity	NPC473490
0.5593	Remote Similarity	NPC472375
0.5521	Remote Similarity	NPC197037
0.5521	Remote Similarity	NPC229545
0.5521	Remote Similarity	NPC134685
0.5455	Remote Similarity	NPC219419
0.5408	Remote Similarity	NPC11588
0.5243	Remote Similarity	NPC479175

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3571
0.1-0.2	5480
0.2-0.3	86
0.3-0.4	3
0.4-0.5	9
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
0.5315	Remote Similarity	NPD8435	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