NPASS Compound

Natural Product: NPC472570

Natural Product ID	NPC472570
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JLOITWJNBYVRLW-YFNVFCEMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3577214
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 1.8185 -0.7538 4.2479 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0653 0.3193 3.5493 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7590 1.3953 4.1296 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6942 0.1486 2.2588 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0175 1.0685 1.4709 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2717 0.5643 0.0631 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0312 1.6278 -0.6536 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3824 1.7626 -0.3104 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3161 1.7110 -1.3485 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9393 1.5359 -2.5274 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7539 1.8673 -1.0620 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3828 2.9992 -0.4973 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9484 3.6483 0.6513 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8047 4.7086 0.6128 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1318 5.1627 -0.5115 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3163 5.2847 1.8854 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0787 3.0597 -0.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8274 1.7646 -0.7141 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0486 0.5159 -0.7550 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6347 0.4017 -2.1013 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9606 -0.7838 -2.6250 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8246 -1.6635 -1.4092 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5836 -1.7763 -0.8783 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8830 -0.7756 0.1788 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2122 -0.7339 0.5822 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7056 -1.1201 1.8184 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8300 -1.5358 2.6594 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0945 -1.0956 2.2316 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0942 -0.7596 1.3554 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4341 -0.7124 1.7473 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7706 -1.0126 3.0552 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7902 -1.3486 3.9368 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4647 -1.3892 3.5269 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4692 -2.0000 -1.8791 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1811 -3.0846 -2.2158 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9697 -4.0293 -1.4613 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0990 -3.1506 -3.3384 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6421 -0.7645 -0.4365 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0111 -0.9242 -0.6530 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8607 -1.5824 0.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 -2.0489 1.2729 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2719 -1.7510 0.0075 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8699 -1.2485 -1.1144 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2466 -1.4073 -1.3371 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9545 -2.0822 -0.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3991 -2.6074 0.7599 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0277 -2.4207 0.9302 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2938 -1.0287 -3.2292 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0188 -1.1549 -3.7363 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9908 1.7925 0.2399 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4873 1.9514 -1.9759 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3642 -1.7517 4.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8540 -0.5866 5.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 -0.8259 3.9070 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0085 1.1505 1.9682 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4237 2.0480 1.5582 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9177 1.4193 -1.7629 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3181 1.1004 -1.6281 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0895 2.8528 -1.4485 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9650 1.8337 0.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8377 3.6009 -1.3495 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6332 5.1253 2.7295 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2899 4.8176 2.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4970 6.3742 1.8060 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3382 3.7759 -1.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5398 3.6917 0.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3362 -2.6320 -1.5347 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5687 -2.7971 -0.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4017 -1.2209 1.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8559 -0.5413 0.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2262 -0.4464 1.0566 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8123 -0.9779 3.3689 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0537 -1.5861 4.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6959 -1.6532 4.2230 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6011 -2.1648 -3.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8564 -3.9364 -3.1423 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5097 -3.3716 -4.2656 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4368 -1.2457 0.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -0.7018 -1.8943 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6923 -1.0074 -2.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0181 -2.2187 -0.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9824 -3.1376 1.4971 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6139 -2.8464 1.8462 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5107 -2.1329 -3.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2803 -0.9065 -4.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1543 -0.4912 -2.9025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9772 -0.6447 -3.6731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0454 -2.2438 -3.9358 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4139 -0.7494 -4.7101 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3268 2.8716 0.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8590 1.2667 -0.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8462 1.4640 1.2419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7998 2.8813 -2.0536 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 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 23 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 22 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 21 48 1 0 21 49 1 0 18 50 1 0 18 51 1 6 24 6 1 0 33 28 1 0 47 42 1 0 19 6 1 0 38 19 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 16 62 1 0 16 63 1 0 16 64 1 0 17 65 1 0 17 66 1 0 22 67 1 6 23 68 1 1 24 69 1 1 29 70 1 0 30 71 1 0 31 72 1 0 32 73 1 0 33 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 38 78 1 1 43 79 1 0 44 80 1 0 45 81 1 0 46 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	JLOITWJNBYVRLW-YFNVFCEMSA-N
Standard InCHI	InChI=1S/C37H42O14/c1-20(38)45-19-36-29(48-23(4)41)26(46-21(2)39)18-35(7,44)37(36)30(49-32(42)24-14-10-8-11-15-24)27(34(5,6)51-37)28(47-22(3)40)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)C)C[C@]([C@@]32OC([C@H]([C@@H]([C@@H]1OC(=O)c1ccccc1)OC(=O)C)[C@H]3OC(=O)c1ccccc1)(C)C)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.26	Volume:	697.151 ? Van der Waals volume.
Dense:	1.019	LogP:	2.77 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.848 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.508 ? 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:	6.01	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:	0.323	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:	0.209 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.085	Promiscuous compounds:	0.099

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.309	MDCK Permeability:	-4.702
Pgp-inhibitor:	1.0	Pgp-substrate:	0.556
PAMPA:	0.179 ? 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%):	0.021	30% Bioavailability (F30%):	0.593
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277	MRP1:	1.0
Plasma Protein Binding (PPB):	76.32%	Volume Distribution (VD):	-0.384
Fu:	21.47% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.004
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.363
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.023
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.002
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):

1.322

Half-life (T1/2):

1.263

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.249
Human Hepatotoxicity (H-HT):	0.06	Drug-induced Liver Injury (DILI):	0.784
AMES Toxicity:	0.801	Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.208	Skin Sensitization:	0.995
Carcinogencity:	0.74	Eye Corrosion:	0.0
Eye Irritation:	0.228	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.405	Ototoxicity:	0.201
Hematotoxicity:	0.098	Drug-induced Nephrotoxicity:	0.588
Genotoxicity:	0.384	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.295	Hek293 Cytotoxicity:	0.47
BCF:	0.612 ? 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:	3.609 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.298 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.753 ? 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
Ratio IC50	6
Ki	1

Activity Type	# Activity
Individual protein	8

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	=	79.7	%	PMID[1965200]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	70.3	n.a.	PMID[16643044]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	22.4	n.a.	PMID[26555243]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	16.4	n.a.	PMID[26814680]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	25.6	n.a.	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	12.7	n.a.	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	3.9	n.a.	PMID[16933872]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	780.0	nM	PMID[20384296]

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 NPC472570 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	13377
0.1-0.2	34152
0.2-0.3	1638
0.3-0.4	483
0.4-0.5	124
0.5-0.6	47
0.6-0.7	25
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC16912
0.8788	High Similarity	NPC472569
0.8788	High Similarity	NPC11685
0.8676	High Similarity	NPC481489
0.8286	Intermediate Similarity	NPC481488
0.7361	Intermediate Similarity	NPC95265
0.7123	Intermediate Similarity	NPC97667
0.6986	Remote Similarity	NPC57628
0.68	Remote Similarity	NPC282239
0.6761	Remote Similarity	NPC281717
0.6761	Remote Similarity	NPC483886
0.6753	Remote Similarity	NPC488917
0.6712	Remote Similarity	NPC471104
0.6709	Remote Similarity	NPC610134
0.6667	Remote Similarity	NPC70716
0.6623	Remote Similarity	NPC481486
0.6579	Remote Similarity	NPC472568
0.6579	Remote Similarity	NPC481490
0.6575	Remote Similarity	NPC472572
0.6494	Remote Similarity	NPC479042
0.6364	Remote Similarity	NPC471102
0.631	Remote Similarity	NPC294512
0.6301	Remote Similarity	NPC473060
0.6235	Remote Similarity	NPC483868
0.6216	Remote Similarity	NPC163719
0.6216	Remote Similarity	NPC147880
0.6216	Remote Similarity	NPC200471
0.6216	Remote Similarity	NPC95810
0.6216	Remote Similarity	NPC472575
0.619	Remote Similarity	NPC30171
0.6104	Remote Similarity	NPC479043
0.6026	Remote Similarity	NPC106895
0.593	Remote Similarity	NPC176413
0.593	Remote Similarity	NPC483885
0.5921	Remote Similarity	NPC148062
0.5867	Remote Similarity	NPC472577
0.5802	Remote Similarity	NPC481487
0.5789	Remote Similarity	NPC90257
0.5789	Remote Similarity	NPC69357
0.5714	Remote Similarity	NPC147217
0.5714	Remote Similarity	NPC137718
0.5658	Remote Similarity	NPC51314
0.5625	Remote Similarity	NPC96903
0.5595	Remote Similarity	NPC610927
0.5568	Remote Similarity	NPC479045
0.5529	Remote Similarity	NPC301368
0.5529	Remote Similarity	NPC84815
0.55	Remote Similarity	NPC252314
0.5467	Remote Similarity	NPC481047
0.5467	Remote Similarity	NPC481045
0.5465	Remote Similarity	NPC148896
0.5455	Remote Similarity	NPC483902
0.5443	Remote Similarity	NPC171207
0.5385	Remote Similarity	NPC483845
0.5375	Remote Similarity	NPC483844
0.5357	Remote Similarity	NPC6815
0.5341	Remote Similarity	NPC253738
0.5316	Remote Similarity	NPC471101
0.525	Remote Similarity	NPC473088
0.519	Remote Similarity	NPC479047
0.519	Remote Similarity	NPC191082
0.519	Remote Similarity	NPC291638
0.5181	Remote Similarity	NPC483848
0.5128	Remote Similarity	NPC90614
0.5128	Remote Similarity	NPC483879
0.5125	Remote Similarity	NPC483846
0.5119	Remote Similarity	NPC294803
0.5119	Remote Similarity	NPC481062
0.5119	Remote Similarity	NPC481058
0.5119	Remote Similarity	NPC481060
0.5116	Remote Similarity	NPC479040
0.51	Remote Similarity	NPC316841
0.5062	Remote Similarity	NPC471100
0.5062	Remote Similarity	NPC605884
0.5059	Remote Similarity	NPC488912
0.5059	Remote Similarity	NPC488910
0.5059	Remote Similarity	NPC488908
0.5059	Remote Similarity	NPC488906
0.5053	Remote Similarity	NPC6981

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3676
0.1-0.2	5309
0.2-0.3	165
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