NPASS Compound

Natural Product: NPC488078

Natural Product ID	NPC488078
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VDWFCLJACQFUBC-WXFKVRFKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 11.8693 0.4304 -2.3832 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1403 0.3672 -3.5962 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7795 0.6024 -3.6638 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0161 0.9128 -2.5571 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6648 1.1498 -2.6098 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0414 1.0705 -3.8472 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7874 0.7597 -4.9757 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1493 0.5274 -4.8822 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8447 0.2214 -6.0346 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8405 1.4592 -1.4303 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3000 1.4902 -0.1956 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5268 1.7897 0.9926 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1079 1.7625 2.0978 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2083 2.0927 0.9204 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3141 2.3681 1.9440 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8600 1.1529 2.6684 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8471 0.2830 3.3277 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0876 -0.9019 3.9797 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2302 -1.5708 2.9295 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3016 -0.4499 2.4136 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2885 -0.9170 1.6502 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0424 -0.7670 1.7148 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8138 -1.4920 0.7761 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1920 -1.3997 0.7747 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8767 -0.6107 1.6707 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1356 0.0964 2.5825 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7300 0.0093 2.5914 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0703 0.7675 3.5444 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1559 2.1407 3.1434 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7925 0.8878 3.4837 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2368 -0.5690 1.6083 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8808 0.1466 2.4184 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9107 -1.3172 0.6493 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1955 -2.0809 -0.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7351 -2.9229 -1.2677 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0506 -3.2822 -1.4006 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5043 -4.0446 -2.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6307 -4.4639 -3.4633 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3065 -4.1120 -3.3407 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8828 -3.3657 -2.2744 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3546 -4.4893 -4.2743 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0735 -5.2301 -4.5584 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8812 -2.0693 -0.0885 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3004 -1.2354 0.6219 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8057 -0.1647 -0.1624 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2116 -0.2055 -0.5655 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4107 0.9272 -1.5952 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0250 2.2157 -0.9135 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6863 2.0787 -0.2419 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2702 3.3576 0.4312 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1104 3.7114 1.4680 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6866 1.0270 0.6649 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9500 2.5946 0.0341 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7143 0.9497 -2.0473 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7305 -1.3664 -1.0678 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1874 0.3674 1.6820 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5381 -2.6036 3.5079 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -1.8254 4.4090 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4575 0.9145 4.4287 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8560 -0.0375 -2.5717 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9644 1.4674 -1.9955 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3628 -0.1911 -1.6236 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5402 0.9638 -1.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9743 1.2502 -3.9363 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3275 0.6881 -5.9590 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8197 -0.0388 -5.9485 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7829 1.6818 -1.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3723 1.2663 -0.0644 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3924 2.8689 1.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7354 3.1139 2.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0926 1.4247 3.4636 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5699 -0.2309 2.6747 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4855 -0.5169 4.8091 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8771 -1.9238 2.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0430 0.1114 3.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2828 -2.1121 0.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8352 2.6331 3.2286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4584 2.1954 2.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8752 2.6245 3.8300 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4517 0.9128 4.4497 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7512 -3.0024 -0.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5376 -4.3155 -2.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8346 -3.0901 -2.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4010 -5.3982 -4.7037 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7534 -5.9631 -4.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1306 0.0909 -0.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8271 0.1688 0.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7206 0.7220 -2.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8833 3.0255 -1.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9358 1.9138 -1.0636 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1804 4.1324 -0.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2508 3.1867 0.8624 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8361 4.6320 1.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8951 2.4108 -0.2047 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3248 0.7150 -1.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2420 -1.8626 -0.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5993 -2.3517 3.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6651 -2.0619 3.6678 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8905 1.7217 4.6275 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 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 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 26 30 1 0 25 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 38 39 1 0 39 40 2 0 39 41 1 0 38 42 1 0 34 43 1 0 33 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 47 54 1 0 46 55 1 0 20 56 1 0 19 57 1 0 18 58 1 0 17 59 1 0 8 3 1 0 56 16 1 0 27 22 1 0 40 35 1 0 52 45 1 0 43 24 1 0 1 60 1 0 1 61 1 0 1 62 1 0 4 63 1 0 6 64 1 0 7 65 1 0 9 66 1 0 10 67 1 0 11 68 1 0 15 69 1 0 15 70 1 0 16 71 1 1 17 72 1 6 18 73 1 1 19 74 1 6 20 75 1 1 23 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 36 81 1 0 37 82 1 0 40 83 1 0 41 84 1 0 42 85 1 0 45 86 1 6 46 87 1 1 47 88 1 6 48 89 1 6 49 90 1 6 50 91 1 0 50 92 1 0 51 93 1 0 53 94 1 0 54 95 1 0 55 96 1 0 57 97 1 0 58 98 1 0 59 99 1 0 M END

Standard InCHIKey	VDWFCLJACQFUBC-WXFKVRFKSA-N
Standard InCHI	InChI=1S/C38H40O21/c1-52-19-9-14(3-6-17(19)41)4-8-24(43)54-13-23-27(45)31(49)32(50)37(58-23)56-21-11-20-25(28(46)35(21)53-2)29(47)36(34(55-20)15-5-7-16(40)18(42)10-15)59-38-33(51)30(48)26(44)22(12-39)57-38/h3-11,22-23,26-27,30-33,37-42,44-46,48-51H,12-13H2,1-2H3/b8-4+/t22-,23-,26+,27-,30+,31+,32-,33-,37-,38+/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc3c(c(c2OC)O)c(=O)c(c(c2ccc(c(c2)O)O)o3)O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	832.21	Volume:	764.786 ? Van der Waals volume.
Dense:	1.088	LogP:	0.884 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.224 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.831 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	38.0
TPSA:	334.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.046	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.207	Fsp³:	0.368
MCE-18:	145.538 ? 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:	1
Colloidal aggregators:	0.707	Fluc inhibitor:	0.368 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.827 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.667 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.052	Promiscuous compounds:	0.515

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.35	MDCK Permeability:	-5.435
Pgp-inhibitor:	0.0	Pgp-substrate:	0.029
PAMPA:	0.987 ? 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):	0.992
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.052
Plasma Protein Binding (PPB):	82.495%	Volume Distribution (VD):	-0.055
Fu:	14.299% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.039
BSEP inhibitor:	0.001

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:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.187 ? 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):

1.351

Half-life (T1/2):

4.521

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.136
Human Hepatotoxicity (H-HT):	0.631	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.965	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.044	Skin Sensitization:	1.0
Carcinogencity:	0.045	Eye Corrosion:	0.0
Eye Irritation:	0.031	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.971
Hematotoxicity:	0.128	Drug-induced Nephrotoxicity:	0.778
Genotoxicity:	0.841	RPMI-8226 Immunitoxicity:	0.217
A549 Cytotoxicity:	0.987	Hek293 Cytotoxicity:	0.663
BCF:	0.627 ? 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:	3.328 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.003 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.266 ? 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
NPO40820	Corispermum marschallii	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[30109803]

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	3

Activity Type	# Activity
Cell line	3

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
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	36600.0	nM	PMID[30109803]
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	46700.0	nM	PMID[30109803]
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	23200.0	nM	PMID[30109803]

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 NPC488078 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	18401
0.1-0.2	27030
0.2-0.3	3125
0.3-0.4	879
0.4-0.5	302
0.5-0.6	89
0.6-0.7	23
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.901	High Similarity	NPC488079
0.7264	Intermediate Similarity	NPC470416
0.7083	Intermediate Similarity	NPC488071
0.6695	Remote Similarity	NPC21359
0.6695	Remote Similarity	NPC460984
0.6667	Remote Similarity	NPC223426
0.6606	Remote Similarity	NPC81042
0.6574	Remote Similarity	NPC36138
0.6535	Remote Similarity	NPC488072
0.6404	Remote Similarity	NPC139571
0.6372	Remote Similarity	NPC217520
0.6337	Remote Similarity	NPC21666
0.6293	Remote Similarity	NPC295625
0.6271	Remote Similarity	NPC470720
0.6262	Remote Similarity	NPC488073
0.6198	Remote Similarity	NPC25946
0.6186	Remote Similarity	NPC470719
0.6186	Remote Similarity	NPC470717
0.6182	Remote Similarity	NPC85751
0.6182	Remote Similarity	NPC19240
0.6161	Remote Similarity	NPC214621
0.6161	Remote Similarity	NPC34267
0.614	Remote Similarity	NPC480796
0.614	Remote Similarity	NPC472993
0.614	Remote Similarity	NPC477895
0.604	Remote Similarity	NPC24043
0.598	Remote Similarity	NPC42773
0.598	Remote Similarity	NPC45522
0.5966	Remote Similarity	NPC470713
0.5882	Remote Similarity	NPC27640
0.5877	Remote Similarity	NPC603856
0.5825	Remote Similarity	NPC471405
0.5825	Remote Similarity	NPC117260
0.578	Remote Similarity	NPC233994
0.5766	Remote Similarity	NPC483415
0.5766	Remote Similarity	NPC488364
0.5728	Remote Similarity	NPC603655
0.5726	Remote Similarity	NPC480472
0.5714	Remote Similarity	NPC483416
0.5673	Remote Similarity	NPC201292
0.5636	Remote Similarity	NPC156869
0.5631	Remote Similarity	NPC136042
0.5625	Remote Similarity	NPC211532
0.5625	Remote Similarity	NPC483414
0.562	Remote Similarity	NPC474093
0.562	Remote Similarity	NPC104910
0.5614	Remote Similarity	NPC473073
0.5577	Remote Similarity	NPC84362
0.5556	Remote Similarity	NPC116864
0.5556	Remote Similarity	NPC244776
0.5556	Remote Similarity	NPC476865
0.5536	Remote Similarity	NPC126784
0.5536	Remote Similarity	NPC241423
0.5536	Remote Similarity	NPC488074
0.5526	Remote Similarity	NPC486577
0.5514	Remote Similarity	NPC476868
0.5512	Remote Similarity	NPC480470
0.5505	Remote Similarity	NPC254540
0.55	Remote Similarity	NPC277532
0.5487	Remote Similarity	NPC470443
0.5455	Remote Similarity	NPC470716
0.5431	Remote Similarity	NPC470445
0.5424	Remote Similarity	NPC599948
0.5421	Remote Similarity	NPC101026
0.5421	Remote Similarity	NPC488077
0.5421	Remote Similarity	NPC476869
0.5417	Remote Similarity	NPC470715
0.5417	Remote Similarity	NPC164704
0.5398	Remote Similarity	NPC153755
0.5391	Remote Similarity	NPC270675
0.5391	Remote Similarity	NPC195685
0.5385	Remote Similarity	NPC470446
0.537	Remote Similarity	NPC602805
0.537	Remote Similarity	NPC605784
0.5345	Remote Similarity	NPC80068
0.5344	Remote Similarity	NPC223860
0.5333	Remote Similarity	NPC145038
0.5333	Remote Similarity	NPC475179
0.5333	Remote Similarity	NPC56077
0.5333	Remote Similarity	NPC487501
0.5333	Remote Similarity	NPC281131
0.5333	Remote Similarity	NPC253662
0.5333	Remote Similarity	NPC179950
0.5333	Remote Similarity	NPC88789
0.5333	Remote Similarity	NPC491374
0.5283	Remote Similarity	NPC488080
0.5283	Remote Similarity	NPC45638
0.5283	Remote Similarity	NPC169977
0.5254	Remote Similarity	NPC470450
0.525	Remote Similarity	NPC470451
0.5234	Remote Similarity	NPC599850
0.5214	Remote Similarity	NPC483413
0.5203	Remote Similarity	NPC470718
0.5185	Remote Similarity	NPC157816
0.5182	Remote Similarity	NPC203050
0.5182	Remote Similarity	NPC225434
0.5167	Remote Similarity	NPC121703
0.5164	Remote Similarity	NPC470712
0.514	Remote Similarity	NPC305811
0.514	Remote Similarity	NPC271692
0.514	Remote Similarity	NPC105025
0.514	Remote Similarity	NPC10205
0.5138	Remote Similarity	NPC120099
0.5135	Remote Similarity	NPC211594
0.5133	Remote Similarity	NPC11411
0.5126	Remote Similarity	NPC472994
0.5094	Remote Similarity	NPC289667
0.5085	Remote Similarity	NPC483412
0.5085	Remote Similarity	NPC477629
0.5082	Remote Similarity	NPC292019
0.5082	Remote Similarity	NPC202908
0.5047	Remote Similarity	NPC297987
0.5044	Remote Similarity	NPC480466
0.5043	Remote Similarity	NPC37668
0.5041	Remote Similarity	NPC480441

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4643
0.1-0.2	4446
0.2-0.3	48
0.3-0.4	8
0.4-0.5	4
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
0.5085	Remote Similarity	NPD7251	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