NPASS Compound

Natural Product: NPC147880

Natural Product ID	NPC147880
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZMFWEJXNCWIVOL-FPJSXKKWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL434717
PubChem CID	11445402
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic acids 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 92 96 0 0 0 0 0 0 0 0999 V2000 -5.5982 0.8000 -1.6436 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1800 1.2917 -1.6372 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0005 2.4673 -2.0475 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1488 0.4825 -1.2019 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8729 0.9740 -1.2142 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7669 0.0532 -0.7279 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4482 0.9162 -0.8577 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6842 1.5650 0.3760 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6883 2.9451 0.5203 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4470 3.6001 -0.5490 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9401 3.6599 1.7539 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8734 5.0345 1.7408 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1166 5.7893 2.8763 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4386 5.1486 4.0707 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5057 3.7713 4.0850 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2557 3.0327 2.9245 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7137 0.2763 -1.3327 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4949 0.0133 -0.1953 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7047 0.5899 0.0749 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1753 1.4044 -0.7329 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4177 0.2518 1.2833 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9629 -0.6062 2.2546 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6822 -0.9041 3.3853 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9123 -0.3456 3.5986 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4095 0.5230 2.6491 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6780 0.8142 1.5178 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5420 -0.8187 -2.3129 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0715 -0.7336 -2.8096 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6084 -1.1982 -1.5840 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3416 -2.0272 -0.9251 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4421 -2.1848 -1.6714 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4970 -3.1747 -2.7705 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6002 -2.5193 -0.7438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7857 -2.0629 -1.7134 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3890 -2.3294 -0.3455 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5647 -1.8013 0.7813 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1644 -0.3529 0.6442 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2993 0.3945 1.1216 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3296 1.1179 2.2730 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3138 1.1462 2.9861 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5849 1.8599 2.6501 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4169 -1.8734 1.9418 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1418 -2.6167 3.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -3.2855 3.0688 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0534 -2.6585 4.2252 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7757 -1.8171 -2.7909 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1236 -1.4403 -3.9733 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3954 -0.9310 -5.2276 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4770 0.3170 -5.3359 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5949 -1.7607 -6.4433 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6299 -0.2774 -1.3889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0820 0.9592 -2.6250 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1691 1.4053 -0.8967 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8658 1.8231 -0.4695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5740 1.4908 -2.1666 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2827 1.7652 -1.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6214 5.5736 0.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0617 6.8667 2.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6293 5.7559 4.9647 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7527 3.2488 4.9951 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3136 1.9506 2.9545 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3329 1.0500 -1.8991 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9763 -1.0658 2.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2757 -1.5804 4.1070 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5162 -0.5519 4.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3927 0.9614 2.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.4867 0.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2279 -0.8100 -3.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0363 0.3543 -3.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5796 -3.5209 -3.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1487 -2.8085 -3.6245 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0408 -4.1217 -2.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3082 -2.4288 0.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7964 -3.6356 -0.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5432 -2.0641 -1.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 -3.0965 -1.9940 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4633 -3.4435 -0.1246 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4690 -2.0449 -0.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7190 -2.4631 1.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3360 -0.1768 1.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8463 1.5495 3.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3820 1.5967 1.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3451 2.9300 2.5843 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7398 -1.9894 5.0333 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0720 -3.7270 4.5711 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0629 -2.3495 3.8987 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8032 -1.8955 -2.3205 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8486 -2.6588 -3.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6380 -0.9411 -3.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1187 -2.7690 -6.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0188 -1.2518 -7.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6525 -1.8935 -6.7104 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 6 5 1 6 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 17 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 30 31 1 0 31 32 1 0 31 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 36 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 34 46 1 0 28 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 37 6 1 0 29 6 1 0 16 11 1 0 26 21 1 0 31 27 1 0 1 51 1 0 1 52 1 0 1 53 1 0 5 54 1 0 5 55 1 0 7 56 1 6 12 57 1 0 13 58 1 0 14 59 1 0 15 60 1 0 16 61 1 0 17 62 1 6 22 63 1 0 23 64 1 0 24 65 1 0 25 66 1 0 26 67 1 0 27 68 1 6 28 69 1 6 32 70 1 0 32 71 1 0 32 72 1 0 33 73 1 0 33 74 1 0 33 75 1 0 34 76 1 6 35 77 1 0 35 78 1 0 36 79 1 1 37 80 1 1 41 81 1 0 41 82 1 0 41 83 1 0 45 84 1 0 45 85 1 0 45 86 1 0 46 87 1 0 46 88 1 0 46 89 1 0 50 90 1 0 50 91 1 0 50 92 1 0 M END

Standard InCHIKey	ZMFWEJXNCWIVOL-FPJSXKKWSA-N
Standard InCHI	InChI=1S/C37H42O13/c1-20-18-27(45-22(3)39)30(46-23(4)40)36(19-44-21(2)38)32(49-34(43)26-16-12-9-13-17-26)29(48-33(42)25-14-10-8-11-15-25)28-31(47-24(5)41)37(20,36)50-35(28,6)7/h8-17,20,27-32H,18-19H2,1-7H3/t20-,27+,28-,29+,30+,31-,32+,36+,37-/m1/s1
SMILES	CC(=O)OC[C@@]12[C@@H](OC(=O)c3ccccc3)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@H]([C@]2(OC3(C)C)[C@@H](C[C@@H]([C@@H]1OC(=O)C)OC(=O)C)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	694.26	Volume:	688.361 ? Van der Waals volume.
Dense:	1.009	LogP:	3.3 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.155 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.001 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	32.0
TPSA:	167.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.273	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.99	Fsp³:	0.514
MCE-18:	171.321 ? 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:	0.445	Fluc inhibitor:	0.041 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.148 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.203	Promiscuous compounds:	0.051

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212	MDCK Permeability:	-4.641
Pgp-inhibitor:	0.998	Pgp-substrate:	0.054
PAMPA:	0.151 ? 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%):	0.002	30% Bioavailability (F30%):	0.105
50% Bioavailability (F50%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.884	MRP1:	1.0
Plasma Protein Binding (PPB):	85.26%	Volume Distribution (VD):	-0.365
Fu:	15.53% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.011
BSEP inhibitor:	0.956

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.503
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.211
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.821
CYP3A4-inhibitor:	0.021	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.936

Half-life (T1/2):

1.069

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.34
Human Hepatotoxicity (H-HT):	0.095	Drug-induced Liver Injury (DILI):	0.853
AMES Toxicity:	0.814	Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.112	Skin Sensitization:	0.993
Carcinogencity:	0.639	Eye Corrosion:	0.0
Eye Irritation:	0.099	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.519	Ototoxicity:	0.272
Hematotoxicity:	0.325	Drug-induced Nephrotoxicity:	0.727
Genotoxicity:	0.391	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.529	Hek293 Cytotoxicity:	0.558
BCF:	0.719 ? 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:	3.78 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.333 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.964 ? 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
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974580]
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Ki	3
Imax	1
Activity	5

Activity Type	# Activity
Cell line	2
Individual protein	3
Others	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	1710.0	nM	DOI[10.6019/CHEMBL1201861]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	1698.24	nM	PMID[19200744]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Imax	=	86.2	%	PMID[17850057]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell line	NIH3T3	Mus musculus	Ki	=	1710.0	nM	DOI[10.1039/C3MD20086H]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[25238443]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	DrugMatrix in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	Activity	=	29.9	%	PMID[17705462]
NPT2	Others	Unspecified	n.a.	Activity	=	73.9	%	PMID[22779787]
NPT2	Others	Unspecified	n.a.	Activity	=	93.5	%	PMID[21911291]

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 NPC147880 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	18021
0.1-0.2	29866
0.2-0.3	1387
0.3-0.4	410
0.4-0.5	91
0.5-0.6	41
0.6-0.7	25
0.7-0.8	0
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC148062
0.8871	High Similarity	NPC147217
0.8871	High Similarity	NPC137718
0.8852	High Similarity	NPC473060
0.8852	High Similarity	NPC51314
0.791	Intermediate Similarity	NPC479043
0.7746	Intermediate Similarity	NPC479040
0.7313	Intermediate Similarity	NPC483845
0.7313	Intermediate Similarity	NPC479047
0.7313	Intermediate Similarity	NPC291638
0.7231	Intermediate Similarity	NPC481047
0.7231	Intermediate Similarity	NPC481045
0.7101	Intermediate Similarity	NPC471100
0.7101	Intermediate Similarity	NPC605884
0.6901	Remote Similarity	NPC252314
0.6901	Remote Similarity	NPC11685
0.6857	Remote Similarity	NPC254558
0.6857	Remote Similarity	NPC471107
0.6812	Remote Similarity	NPC90257
0.6812	Remote Similarity	NPC4341
0.6812	Remote Similarity	NPC69357
0.6761	Remote Similarity	NPC479044
0.6667	Remote Similarity	NPC483902
0.6667	Remote Similarity	NPC472577
0.6622	Remote Similarity	NPC483849
0.6571	Remote Similarity	NPC191082
0.6528	Remote Similarity	NPC483844
0.6479	Remote Similarity	NPC43241
0.6438	Remote Similarity	NPC16912
0.6438	Remote Similarity	NPC609924
0.6389	Remote Similarity	NPC473088
0.6267	Remote Similarity	NPC483848
0.625	Remote Similarity	NPC177340
0.6216	Remote Similarity	NPC472569
0.6216	Remote Similarity	NPC472570
0.6133	Remote Similarity	NPC184747
0.6027	Remote Similarity	NPC139067
0.6	Remote Similarity	NPC475429
0.6	Remote Similarity	NPC211137
0.5974	Remote Similarity	NPC481050
0.5974	Remote Similarity	NPC481489
0.5974	Remote Similarity	NPC609221
0.5857	Remote Similarity	NPC195647
0.5833	Remote Similarity	NPC241951
0.5811	Remote Similarity	NPC67777
0.5696	Remote Similarity	NPC481488
0.5634	Remote Similarity	NPC200592
0.5634	Remote Similarity	NPC610542
0.5625	Remote Similarity	NPC608007
0.5584	Remote Similarity	NPC57628
0.5556	Remote Similarity	NPC66761
0.5556	Remote Similarity	NPC483843
0.5556	Remote Similarity	NPC476094
0.5542	Remote Similarity	NPC473115
0.5542	Remote Similarity	NPC75600
0.5542	Remote Similarity	NPC483884
0.5541	Remote Similarity	NPC17877
0.5541	Remote Similarity	NPC281717
0.5526	Remote Similarity	NPC471104
0.5513	Remote Similarity	NPC97667
0.55	Remote Similarity	NPC483887
0.55	Remote Similarity	NPC158020
0.5417	Remote Similarity	NPC473081
0.5405	Remote Similarity	NPC90614
0.5395	Remote Similarity	NPC483842
0.5325	Remote Similarity	NPC473758
0.5316	Remote Similarity	NPC70716
0.5316	Remote Similarity	NPC95265
0.5256	Remote Similarity	NPC41481
0.5238	Remote Similarity	NPC473089
0.5205	Remote Similarity	NPC270498
0.52	Remote Similarity	NPC483862
0.5122	Remote Similarity	NPC481486
0.5072	Remote Similarity	NPC216137
0.5068	Remote Similarity	NPC481066
0.5063	Remote Similarity	NPC306146
0.5063	Remote Similarity	NPC483841
0.5062	Remote Similarity	NPC282239
0.5062	Remote Similarity	NPC472568
0.5062	Remote Similarity	NPC481490

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC147880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4156
0.1-0.2	4838
0.2-0.3	156
0.3-0.4	0
0.4-0.5	0
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