NPASS Compound

Natural Product: NPC472569

Natural Product ID	NPC472569
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VLDOGFDAFSEYTM-YFNVFCEMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3577213
PubChem CID	n.a.
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 93 97 0 0 0 0 0 0 0 0999 V2000 -1.6003 -3.3983 4.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6511 -2.4143 4.0770 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2741 -1.9732 4.8118 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7565 -1.9799 2.7659 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1537 -1.0562 2.2489 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0855 -0.6719 0.7954 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9745 0.3584 0.3990 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5643 0.8817 1.5980 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6208 2.2238 1.8994 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1556 3.0900 1.1196 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2340 2.7334 3.1634 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0940 -0.2218 -0.4408 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2142 0.6818 -0.4407 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6679 1.3194 -1.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0602 1.0855 -2.6516 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7926 2.2336 -1.6069 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2095 2.8481 -2.7624 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2863 3.7235 -2.7840 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9488 3.9781 -1.6153 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5527 3.3784 -0.4517 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4656 2.4969 -0.4398 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4956 -1.5887 -0.0291 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3305 -2.5151 -0.1772 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0142 -1.8356 -0.1626 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2171 -1.2623 -1.4532 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5104 -1.4603 -1.8312 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2648 -1.9230 -0.6253 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5657 -0.9156 0.4161 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4082 0.0140 0.7537 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4674 1.1912 -0.0214 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8536 2.4298 0.4609 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1668 2.4677 1.6786 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9162 3.6465 -0.3285 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5920 3.7003 -1.6597 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6738 4.8889 -2.3475 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0804 6.0532 -1.7259 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4099 6.0269 -0.3968 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3191 4.8229 0.2673 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7167 -0.1589 0.1995 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8397 -0.1632 1.0092 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8219 -0.9095 2.0221 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9792 0.6947 0.6455 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1466 -2.7879 0.0057 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0478 -3.9052 -0.8667 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3231 -5.1596 -0.3423 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6498 -5.3422 0.8487 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2207 -6.3341 -1.2517 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6210 -2.5782 -2.8582 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1207 -0.2435 -2.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4897 -3.6273 0.8149 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4632 -3.1244 -1.4495 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9299 -4.1245 3.8724 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5095 -2.9281 5.0442 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1269 -4.0087 5.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0252 -0.1007 2.8296 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1584 -1.4418 2.4503 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5287 1.2028 -0.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8655 1.9697 3.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9077 3.5975 2.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4653 3.1460 3.8481 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7683 -0.2363 -1.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7140 2.6762 -3.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6046 4.2046 -3.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7805 4.6497 -1.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0799 3.5775 0.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2147 2.0644 0.5177 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2987 -1.9262 -0.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9946 -1.6474 0.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1510 -2.5095 -0.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7531 -1.5057 1.3636 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6781 0.3740 1.7945 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2799 2.8032 -2.1341 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4212 4.9373 -3.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1530 7.0066 -2.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7288 6.9329 0.0914 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5834 4.8218 1.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6631 0.1284 -0.0401 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6011 0.9677 1.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5932 1.5709 0.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4256 -3.0586 1.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1211 -6.5351 -1.3783 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5876 -6.0352 -2.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7466 -7.2258 -0.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6992 -3.1114 -3.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9465 -2.1853 -3.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4750 -3.2716 -2.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 0.1504 -2.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4640 -0.4582 -3.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2884 0.4728 -2.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3060 -3.3934 1.5606 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8490 -4.5903 0.3430 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6176 -3.8981 1.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7989 -2.4807 -2.1168 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 1 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 7 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 12 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 28 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 27 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 26 48 1 0 26 49 1 0 23 50 1 0 23 51 1 6 29 6 1 0 38 33 1 0 24 6 1 0 21 16 1 0 43 24 1 0 1 52 1 0 1 53 1 0 1 54 1 0 5 55 1 0 5 56 1 0 7 57 1 6 11 58 1 0 11 59 1 0 11 60 1 0 12 61 1 6 17 62 1 0 18 63 1 0 19 64 1 0 20 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 27 69 1 6 28 70 1 1 29 71 1 1 34 72 1 0 35 73 1 0 36 74 1 0 37 75 1 0 38 76 1 0 42 77 1 0 42 78 1 0 42 79 1 0 43 80 1 1 47 81 1 0 47 82 1 0 47 83 1 0 48 84 1 0 48 85 1 0 48 86 1 0 49 87 1 0 49 88 1 0 49 89 1 0 50 90 1 0 50 91 1 0 50 92 1 0 51 93 1 0 M END

Standard InCHIKey	VLDOGFDAFSEYTM-YFNVFCEMSA-N
Standard InCHI	InChI=1S/C37H42O14/c1-20(38)45-19-36-29(47-22(3)40)26(49-32(42)24-14-10-8-11-15-24)18-35(7,44)37(36)30(48-23(4)41)27(34(5,6)51-37)28(46-21(2)39)31(36)50-33(43)25-16-12-9-13-17-25/h8-17,26-31,44H,18-19H2,1-7H3/t26-,27+,28-,29-,30+,31-,35-,36-,37-/m0/s1
SMILES	CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)c3ccccc3)C[C@]([C@@]32OC([C@H]([C@@H]([C@@H]1OC(=O)c1ccccc1)OC(=O)C)[C@H]3OC(=O)C)(C)C)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.26	Volume:	697.151 ? Van der Waals volume.
Dense:	1.019	LogP:	2.965 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.935 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.67 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	32.0
TPSA:	187.26 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.012	Fsp³:	0.514
MCE-18:	180.107 ? 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:	0.33	Fluc inhibitor:	0.01 ? 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:	0.202 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.085	Promiscuous compounds:	0.107

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.285	MDCK Permeability:	-4.733
Pgp-inhibitor:	1.0	Pgp-substrate:	0.136
PAMPA:	0.102 ? 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%):	0.009	30% Bioavailability (F30%):	0.343
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.541	MRP1:	1.0
Plasma Protein Binding (PPB):	76.897%	Volume Distribution (VD):	-0.469
Fu:	22.535% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.974	BCRP inhibitor:	0.004
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.291	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.996 ? 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):

1.511

Half-life (T1/2):

1.304

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.263
Human Hepatotoxicity (H-HT):	0.067	Drug-induced Liver Injury (DILI):	0.83
AMES Toxicity:	0.83	Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.316	Skin Sensitization:	0.998
Carcinogencity:	0.83	Eye Corrosion:	0.0
Eye Irritation:	0.263	Respiratory Toxicity:	0.021
Drug-induced Neurotoxicity:	0.432	Ototoxicity:	0.167
Hematotoxicity:	0.048	Drug-induced Nephrotoxicity:	0.634
Genotoxicity:	0.669	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.284	Hek293 Cytotoxicity:	0.474
BCF:	0.618 ? 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:	3.578 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.177 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.683 ? 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
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	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

Activity Type	# Activity
Activity	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
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	73.8	%	PubChem BioAssay data set

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 NPC472569 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	11721
0.1-0.2	35614
0.2-0.3	1813
0.3-0.4	497
0.4-0.5	124
0.5-0.6	52
0.6-0.7	22
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC16912
0.9104	High Similarity	NPC481488
0.8788	High Similarity	NPC11685
0.8788	High Similarity	NPC472570
0.8676	High Similarity	NPC481489
0.7761	Intermediate Similarity	NPC483886
0.7465	Intermediate Similarity	NPC57628
0.7361	Intermediate Similarity	NPC70716
0.726	Intermediate Similarity	NPC472568
0.7027	Intermediate Similarity	NPC471102
0.6892	Remote Similarity	NPC97667
0.6842	Remote Similarity	NPC481486
0.6761	Remote Similarity	NPC281717
0.6753	Remote Similarity	NPC488917
0.6712	Remote Similarity	NPC471104
0.6667	Remote Similarity	NPC95265
0.6579	Remote Similarity	NPC282239
0.6494	Remote Similarity	NPC479042
0.6316	Remote Similarity	NPC479043
0.6301	Remote Similarity	NPC473060
0.6216	Remote Similarity	NPC147880
0.619	Remote Similarity	NPC30171
0.6154	Remote Similarity	NPC481490
0.6133	Remote Similarity	NPC472572
0.6133	Remote Similarity	NPC137718
0.6118	Remote Similarity	NPC176413
0.6118	Remote Similarity	NPC483885
0.6118	Remote Similarity	NPC479045
0.6098	Remote Similarity	NPC610134
0.6081	Remote Similarity	NPC51314
0.6	Remote Similarity	NPC90257
0.6	Remote Similarity	NPC69357
0.5921	Remote Similarity	NPC471101
0.5921	Remote Similarity	NPC148062
0.5789	Remote Similarity	NPC163719
0.5789	Remote Similarity	NPC200471
0.5789	Remote Similarity	NPC95810
0.5789	Remote Similarity	NPC472575
0.5747	Remote Similarity	NPC294512
0.5714	Remote Similarity	NPC147217
0.5696	Remote Similarity	NPC252314
0.5682	Remote Similarity	NPC483868
0.5658	Remote Similarity	NPC472577
0.5641	Remote Similarity	NPC171207
0.5625	Remote Similarity	NPC106895
0.5584	Remote Similarity	NPC483845
0.557	Remote Similarity	NPC483844
0.5556	Remote Similarity	NPC483848
0.5488	Remote Similarity	NPC294803
0.5488	Remote Similarity	NPC481062
0.5488	Remote Similarity	NPC481058
0.5488	Remote Similarity	NPC481060
0.5467	Remote Similarity	NPC481047
0.5467	Remote Similarity	NPC481045
0.5443	Remote Similarity	NPC473088
0.5432	Remote Similarity	NPC96903
0.5422	Remote Similarity	NPC481487
0.5385	Remote Similarity	NPC4341
0.5376	Remote Similarity	NPC6981
0.5325	Remote Similarity	NPC90614
0.5294	Remote Similarity	NPC479040
0.5256	Remote Similarity	NPC483902
0.5233	Remote Similarity	NPC125106
0.5233	Remote Similarity	NPC472573
0.5233	Remote Similarity	NPC610927
0.519	Remote Similarity	NPC479047
0.519	Remote Similarity	NPC191082
0.519	Remote Similarity	NPC291638
0.5181	Remote Similarity	NPC51602
0.5176	Remote Similarity	NPC479049
0.5172	Remote Similarity	NPC301368
0.5172	Remote Similarity	NPC84815
0.5128	Remote Similarity	NPC483862
0.5125	Remote Similarity	NPC483846
0.5119	Remote Similarity	NPC481064
0.5119	Remote Similarity	NPC483849
0.5114	Remote Similarity	NPC180668
0.5114	Remote Similarity	NPC10904
0.5114	Remote Similarity	NPC148896
0.5065	Remote Similarity	NPC66761
0.5065	Remote Similarity	NPC483843
0.5065	Remote Similarity	NPC476094
0.5062	Remote Similarity	NPC471100
0.5062	Remote Similarity	NPC605884

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3507
0.1-0.2	5477
0.2-0.3	166
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