NPASS Compound

Natural Product: NPC167469

Natural Product ID	NPC167469
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LLRJOEHNJYWWTF-PMQFEAPASA-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] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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 96102 0 0 0 0 0 0 0 0999 V2000 -1.2966 0.6057 1.9848 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8268 0.0345 0.6625 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3067 -1.3711 0.5959 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0839 -1.5990 -0.1982 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 -0.4588 -0.4071 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2422 0.9011 -0.4463 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2659 0.9168 -0.4229 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8215 0.6275 -1.7975 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2869 0.8772 -1.7734 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9100 0.9549 -0.4246 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3219 0.0260 0.6070 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0037 0.3160 1.9214 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2503 1.1053 1.8210 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1664 0.7895 0.6753 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0968 1.9697 0.4941 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9731 -0.4497 0.8920 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2981 -1.5678 0.0838 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5708 -0.8472 -1.0289 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3763 0.5836 -0.5964 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8575 1.3985 -1.6220 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3888 -0.3316 0.4638 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4361 -0.4622 1.2479 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6364 -0.2767 0.4662 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8452 -0.3213 0.8339 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2650 -0.0259 -0.8286 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8714 -0.0904 -0.9129 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2739 -0.8547 2.6350 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8889 -0.5436 0.5103 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1171 -0.7513 -0.0647 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9967 0.4365 0.3266 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0024 0.0144 1.3971 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9603 -0.9445 0.6777 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0639 -1.8889 -0.1063 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7617 -1.8911 0.3912 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7176 -0.1436 -0.1638 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0753 -0.2457 0.1421 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8756 -0.7375 -1.0364 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3403 -0.7086 -0.6526 C 0 0 2 0 0 0 0 0 0 0 0 0 10.6629 0.6434 -0.1068 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4408 1.5355 -0.1883 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4673 0.9801 0.6284 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9656 0.5058 1.2515 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0951 -0.9344 -1.7936 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4727 -2.0770 -1.2460 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7319 1.1325 1.7346 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6658 0.9772 -0.7428 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1762 0.5046 1.9419 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5742 -0.0470 2.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4950 1.6655 2.1124 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1054 -2.0441 0.1549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1656 -1.7886 1.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5173 -2.4103 0.3279 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3002 -2.1122 -1.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3158 -0.6022 -1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6520 1.5038 0.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5261 1.4964 -1.3666 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5633 1.9563 -0.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3242 1.3579 -2.4791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6610 -0.4168 -2.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8056 0.1510 -2.4512 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4822 1.8753 -2.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9034 1.9680 0.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6462 -1.0122 0.3372 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3109 0.9102 2.5832 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9715 2.1855 1.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8271 0.9906 2.7629 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0049 2.4586 -0.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8070 2.7426 1.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1305 1.6840 0.7885 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9611 -0.7267 1.9788 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1178 -2.2228 -0.3238 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6680 -2.2178 0.6926 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2466 -0.9060 -1.9349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6456 -1.3533 -1.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4062 2.2498 -1.7231 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4344 -0.6786 2.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5240 0.8405 -1.3772 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5876 -0.9880 -1.5378 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7087 -1.6034 2.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0769 -0.8146 -1.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3921 1.2467 0.8125 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5338 -0.4452 2.2656 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5995 -1.4723 1.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0154 -1.4861 -1.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5064 -2.8997 -0.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1567 -0.9647 0.9979 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6949 -0.1609 -1.9509 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4806 -1.5098 0.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4651 1.1100 -0.6761 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6979 2.5271 0.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1226 1.6849 -1.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7001 -0.1281 1.4258 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8744 -0.3442 -1.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6892 -2.1325 -1.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5960 1.3318 2.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9872 1.2380 -1.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 16 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 12 27 1 0 5 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 31 45 1 0 30 46 1 0 7 2 1 0 19 10 1 0 26 21 1 0 34 29 1 0 41 36 1 0 11 2 1 0 19 14 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 6 6 55 1 0 6 56 1 0 7 57 1 1 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 1 11 63 1 6 12 64 1 1 13 65 1 0 13 66 1 0 15 67 1 0 15 68 1 0 15 69 1 0 16 70 1 1 17 71 1 0 17 72 1 0 18 73 1 0 18 74 1 0 20 75 1 0 22 76 1 0 26 77 1 0 26 78 1 0 27 79 1 0 29 80 1 6 30 81 1 1 31 82 1 1 32 83 1 1 33 84 1 0 33 85 1 0 36 86 1 1 37 87 1 6 38 88 1 1 39 89 1 6 40 90 1 0 40 91 1 0 42 92 1 0 43 93 1 0 44 94 1 0 45 95 1 0 46 96 1 0 M END

Standard InCHIKey	LLRJOEHNJYWWTF-PMQFEAPASA-N
Standard InCHI	InChI=1S/C33H50O13/c1-31-7-5-17(45-29-28(40)26(38)22(14-44-29)46-30-27(39)25(37)21(35)13-43-30)10-16(31)3-4-19-24(31)20(34)11-32(2)18(6-8-33(19,32)41)15-9-23(36)42-12-15/h9,16-22,24-30,34-35,37-41H,3-8,10-14H2,1-2H3/t16-,17+,18-,19-,20-,21-,22-,24-,25+,26-,27-,28-,29+,30+,31+,32-,33+/m1/s1
SMILES	C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2[C@@H](C[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1)O)O[C@H]1[C@@H]([C@@H]([C@@H](CO1)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.33	Volume:	628.429 ? Van der Waals volume.
Dense:	1.041	LogP:	0.181 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.907 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.431 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	38.0
TPSA:	204.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.148	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.66	Fsp³:	0.909
MCE-18:	132.889 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.66	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.112	Promiscuous compounds:	0.328

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.405	MDCK Permeability:	-5.255
Pgp-inhibitor:	0.0	Pgp-substrate:	0.99
PAMPA:	1.0 ? 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):	0.009
20% Bioavailability (F20%):	0.328	30% Bioavailability (F30%):	0.118
50% Bioavailability (F50%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.677
Plasma Protein Binding (PPB):	57.054%	Volume Distribution (VD):	-0.531
Fu:	43.064% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.94	BCRP inhibitor:	0.006
BSEP inhibitor:	0.101

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.02	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.063
HLM stability:	0.002 ? 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):

1.196

Half-life (T1/2):

2.78

ADMET: Toxicity

hERG Blockers:	0.103	hERG Blockers (10um):	0.394
Human Hepatotoxicity (H-HT):	0.812	Drug-induced Liver Injury (DILI):	0.382
AMES Toxicity:	0.91	Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.472	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.961
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.954
Hematotoxicity:	0.762	Drug-induced Nephrotoxicity:	0.975
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.86
A549 Cytotoxicity:	0.882	Hek293 Cytotoxicity:	0.975
BCF:	0.548 ? 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:	3.164 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.557 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.813 ? 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
NPO8732	Thermopsis fabacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8732	Thermopsis fabacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8732	Thermopsis fabacea	Species	Fabaceae	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

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

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 NPC167469 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	14891
0.1-0.2	29926
0.2-0.3	4276
0.3-0.4	560
0.4-0.5	111
0.5-0.6	81
0.6-0.7	13
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
0.6966	Remote Similarity	NPC30483
0.6966	Remote Similarity	NPC470897
0.6512	Remote Similarity	NPC99620
0.6364	Remote Similarity	NPC5311
0.6263	Remote Similarity	NPC486144
0.6263	Remote Similarity	NPC486145
0.6263	Remote Similarity	NPC486147
0.6263	Remote Similarity	NPC486148
0.61	Remote Similarity	NPC475590
0.6078	Remote Similarity	NPC474908
0.6023	Remote Similarity	NPC158344
0.6	Remote Similarity	NPC236973
0.6	Remote Similarity	NPC469750
0.598	Remote Similarity	NPC475419
0.5934	Remote Similarity	NPC76572
0.5934	Remote Similarity	NPC193382
0.5922	Remote Similarity	NPC486134
0.5922	Remote Similarity	NPC486141
0.5889	Remote Similarity	NPC219085
0.5833	Remote Similarity	NPC292467
0.5824	Remote Similarity	NPC77299
0.5824	Remote Similarity	NPC480906
0.5816	Remote Similarity	NPC486143
0.5816	Remote Similarity	NPC486142
0.5816	Remote Similarity	NPC486149
0.5784	Remote Similarity	NPC486136
0.5761	Remote Similarity	NPC199428
0.5761	Remote Similarity	NPC109448
0.5761	Remote Similarity	NPC310341
0.5761	Remote Similarity	NPC480914
0.5755	Remote Similarity	NPC474423
0.5732	Remote Similarity	NPC160583
0.5604	Remote Similarity	NPC471633
0.5556	Remote Similarity	NPC264336
0.5543	Remote Similarity	NPC196429
0.5521	Remote Similarity	NPC480907
0.551	Remote Similarity	NPC32177
0.551	Remote Similarity	NPC469756
0.551	Remote Similarity	NPC275901
0.5455	Remote Similarity	NPC188234
0.5455	Remote Similarity	NPC480910
0.5455	Remote Similarity	NPC240070
0.5455	Remote Similarity	NPC480909
0.5421	Remote Similarity	NPC486150
0.5392	Remote Similarity	NPC486146
0.5385	Remote Similarity	NPC479360
0.5385	Remote Similarity	NPC479359
0.5368	Remote Similarity	NPC83287
0.5364	Remote Similarity	NPC286809
0.5361	Remote Similarity	NPC72260
0.5347	Remote Similarity	NPC59288
0.5347	Remote Similarity	NPC486135
0.5347	Remote Similarity	NPC486137
0.5319	Remote Similarity	NPC157376
0.5319	Remote Similarity	NPC142066
0.5319	Remote Similarity	NPC603972
0.5312	Remote Similarity	NPC179412
0.5312	Remote Similarity	NPC471356
0.5312	Remote Similarity	NPC471353
0.5294	Remote Similarity	NPC232785
0.5294	Remote Similarity	NPC486139
0.5288	Remote Similarity	NPC486131
0.5269	Remote Similarity	NPC99728
0.5269	Remote Similarity	NPC87250
0.5269	Remote Similarity	NPC244402
0.5269	Remote Similarity	NPC50305
0.5263	Remote Similarity	NPC84949
0.5263	Remote Similarity	NPC480562
0.5263	Remote Similarity	NPC74945
0.5263	Remote Similarity	NPC31354
0.5263	Remote Similarity	NPC69576
0.5263	Remote Similarity	NPC604978
0.5248	Remote Similarity	NPC610296
0.5238	Remote Similarity	NPC486128
0.5234	Remote Similarity	NPC120390
0.5234	Remote Similarity	NPC74259
0.5208	Remote Similarity	NPC250556
0.5158	Remote Similarity	NPC17896
0.5158	Remote Similarity	NPC469755
0.5158	Remote Similarity	NPC284406
0.5158	Remote Similarity	NPC197707
0.5158	Remote Similarity	NPC251866
0.5158	Remote Similarity	NPC480915
0.5155	Remote Similarity	NPC484202
0.5155	Remote Similarity	NPC93883
0.5155	Remote Similarity	NPC305574
0.5149	Remote Similarity	NPC608063
0.5091	Remote Similarity	NPC488945
0.5091	Remote Similarity	NPC488946
0.5053	Remote Similarity	NPC84987
0.505	Remote Similarity	NPC40749
0.5049	Remote Similarity	NPC125077
0.5049	Remote Similarity	NPC55532
0.5049	Remote Similarity	NPC208193

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC167469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6070
0.1-0.2	2958
0.2-0.3	104
0.3-0.4	6
0.4-0.5	7
0.5-0.6	5
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
0.5368	Remote Similarity	NPD7327	Approved
0.5368	Remote Similarity	NPD7328	Phase 4
0.5361	Remote Similarity	NPD8294	Phase 4
0.5208	Remote Similarity	NPD7507	Pre-clinical
0.5158	Remote Similarity	NPD7319	Approved

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