NPASS Compound

Natural Product: NPC476174

Natural Product ID	NPC476174
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WQMAGDSBYCIARL-VXEOXPBSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL550926
PubChem CID	45271778
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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 80 84 0 0 0 0 0 0 0 0999 V2000 3.8658 -0.2818 2.3588 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0862 -0.3376 1.0610 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8264 0.3286 -0.0057 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1628 -0.3566 -0.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9353 0.2866 -1.3019 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1800 -0.0695 -1.4938 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8007 -1.1267 -0.6073 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9635 0.5444 -2.5507 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4540 1.4119 -3.2784 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2703 0.1564 -2.7364 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8833 -0.3938 0.9716 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7084 0.0598 1.3668 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5896 1.4803 1.9499 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0650 1.6221 2.0577 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5487 0.4730 1.3351 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0154 -0.6477 2.2100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7737 0.8648 0.5222 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9154 1.1021 1.4834 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2514 1.1784 0.7357 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3974 -0.1821 0.0922 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8180 -0.4988 -0.2646 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7880 0.5270 0.3228 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2532 -1.8481 0.2863 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0084 -0.5687 -1.7425 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8661 0.0428 -2.3299 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0722 -1.4481 -2.4897 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7332 -1.5902 -1.7588 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4254 -0.3164 -0.9982 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7832 0.7310 -1.7624 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0448 -0.0034 -0.6083 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0169 -0.9693 -1.0533 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1400 -1.2431 -0.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6161 0.0486 0.4169 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7997 0.9837 -0.7349 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4624 -1.1929 2.5641 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4195 0.6626 2.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0969 -0.2944 3.1922 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0856 -1.4446 0.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3213 0.1576 -1.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0525 1.4000 0.1504 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9413 -1.4010 -0.5868 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4800 1.0249 -1.9107 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0885 -1.9070 -0.3415 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3396 -0.6716 0.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5934 -1.6239 -1.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9415 0.6907 -3.2966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3775 0.4650 1.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4551 -0.5578 2.2858 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9846 1.5322 2.9654 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0484 2.2352 1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2284 2.5578 1.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2615 1.7236 3.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3296 -0.1865 3.1902 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8782 -1.2112 1.7382 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3177 -1.4333 2.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5758 1.9199 0.1600 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0501 0.3496 2.2551 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8350 2.0865 2.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2967 2.0070 0.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0247 1.2842 1.5252 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1084 -0.9200 0.9019 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7715 0.3142 -0.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4626 1.5560 0.0842 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8691 0.3208 1.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3220 -2.6185 -0.5172 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2366 -1.8063 0.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4851 -2.2274 0.9986 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4664 -2.4860 -2.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9124 -0.9671 -3.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7119 -2.4548 -1.0926 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9896 -1.7282 -2.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0526 1.7830 -1.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4248 0.5079 -2.7970 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4881 -1.9778 -1.2592 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6408 -0.6498 -2.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1128 -2.0302 0.5365 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9622 -1.6613 -0.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0881 1.5255 -1.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5894 1.7431 -0.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 0.3932 -1.6658 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 4 11 1 0 2 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 28 27 1 6 28 29 1 0 30 29 1 6 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 6 33 12 1 0 33 15 1 0 30 17 1 0 28 20 1 0 30 28 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 6 3 39 1 0 3 40 1 0 4 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 10 46 1 0 11 47 1 0 12 48 1 1 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 16 55 1 0 17 56 1 6 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 1 22 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 29 72 1 0 29 73 1 0 31 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	WQMAGDSBYCIARL-VXEOXPBSSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-18(15-20(31)16-19(2)25(33)34)21-9-11-28(6)23-8-7-22-26(3,4)24(32)10-12-29(22)17-30(23,29)14-13-27(21,28)5/h16,18,20-23,31H,7-15,17H2,1-6H3,(H,33,34)/b19-16+/t18-,20?,21-,22+,23+,27-,28+,29-,30+/m1/s1
SMILES	C[C@H](CC(/C=C(C)/C(=O)O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)C(=O)CC[C@]54C[C@@]35CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.056 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.801 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.176 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	25.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.455	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.646	Fsp³:	0.867
MCE-18:	137.071 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.857	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.305	Promiscuous compounds:	0.092

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.469	MDCK Permeability:	-5.026
Pgp-inhibitor:	0.007	Pgp-substrate:	0.0
PAMPA:	0.978 ? 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):	0.002
20% Bioavailability (F20%):	0.023	30% Bioavailability (F30%):	0.254
50% Bioavailability (F50%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.485
Plasma Protein Binding (PPB):	85.558%	Volume Distribution (VD):	-0.264
Fu:	15.991% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.325
BSEP inhibitor:	0.782

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.02	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.427
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.046
HLM stability:	0.003 ? 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):

2.876

Half-life (T1/2):

1.346

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.076
Human Hepatotoxicity (H-HT):	0.762	Drug-induced Liver Injury (DILI):	0.569
AMES Toxicity:	0.113	Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.625	Skin Sensitization:	0.724
Carcinogencity:	0.592	Eye Corrosion:	0.002
Eye Irritation:	0.144	Respiratory Toxicity:	0.844
Drug-induced Neurotoxicity:	0.074	Ototoxicity:	0.872
Hematotoxicity:	0.591	Drug-induced Nephrotoxicity:	0.853
Genotoxicity:	0.858	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.045	Hek293 Cytotoxicity:	0.119
BCF:	1.198 ? 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:	4.174 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.689 ? 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
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757720]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593279]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	China	n.a.	PMID[19278239]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	Ywar Taw village, Shan State of Myanmar	2006-Dec	PMID[19572611]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO41067	Trigona minor	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28783356]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	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
CD100	1
PC50	3

Activity Type	# Activity
Cell line	3
Non-molecular	1

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
NPT461	Cell line	PANC-1	Homo sapiens	CD100	=	50.0	uM	PMID[20028029]
NPT461	Cell line	PANC-1	Homo sapiens	PC50	=	28.0	uM	PMID[19572611]
NPT461	Cell line	PANC-1	Homo sapiens	PC50	=	16.8	uM	PMID[28783356]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	PC50	=	32.3	uM	PMID[27466882]

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 NPC476174 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	19473
0.1-0.2	27016
0.2-0.3	2902
0.3-0.4	343
0.4-0.5	86
0.5-0.6	25
0.6-0.7	8
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
0.7258	Intermediate Similarity	NPC85379
0.7258	Intermediate Similarity	NPC144909
0.7258	Intermediate Similarity	NPC476304
0.7188	Intermediate Similarity	NPC479653
0.7097	Intermediate Similarity	NPC16287
0.6984	Remote Similarity	NPC60350
0.6923	Remote Similarity	NPC23217
0.6833	Remote Similarity	NPC264602
0.6462	Remote Similarity	NPC476293
0.625	Remote Similarity	NPC474962
0.6176	Remote Similarity	NPC29152
0.6032	Remote Similarity	NPC282275
0.6	Remote Similarity	NPC479655
0.5938	Remote Similarity	NPC477858
0.5915	Remote Similarity	NPC479661
0.589	Remote Similarity	NPC73506
0.5857	Remote Similarity	NPC156546
0.5806	Remote Similarity	NPC255650
0.5758	Remote Similarity	NPC479660
0.5714	Remote Similarity	NPC214770
0.5714	Remote Similarity	NPC477856
0.5556	Remote Similarity	NPC479651
0.5556	Remote Similarity	NPC477857
0.5469	Remote Similarity	NPC107704
0.5441	Remote Similarity	NPC110923
0.5441	Remote Similarity	NPC74296
0.5429	Remote Similarity	NPC181743
0.5429	Remote Similarity	NPC178025
0.5385	Remote Similarity	NPC474123
0.5342	Remote Similarity	NPC607625
0.5286	Remote Similarity	NPC472744
0.5217	Remote Similarity	NPC476186
0.5139	Remote Similarity	NPC472745
0.5132	Remote Similarity	NPC287833
0.507	Remote Similarity	NPC195366
0.507	Remote Similarity	NPC114743
0.5068	Remote Similarity	NPC486364
0.5067	Remote Similarity	NPC486362

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5521
0.1-0.2	3504
0.2-0.3	125
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