NPASS Compound

Natural Product: NPC149400

Natural Product ID	NPC149400
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UJJOTHZQHRLIPY-JJBBQBTFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448906
PubChem CID	11342225
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 95101 0 0 0 0 0 0 0 0999 V2000 8.1541 3.2639 1.1140 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8634 2.7049 0.5605 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2223 1.6411 -0.4608 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9888 0.8783 -0.8860 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1623 0.4906 0.3206 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7573 -0.9688 0.2033 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6562 -1.8106 1.1179 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3915 -0.9890 0.7994 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1104 0.4680 1.1834 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6522 0.7132 0.8534 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1125 -0.6520 0.6284 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1695 -0.7490 -0.0971 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2698 -0.3184 0.8826 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5555 -0.3682 0.0472 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8282 -1.8357 -0.1640 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2226 -2.0583 -0.6072 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5117 -3.4094 -1.1786 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3660 -4.0363 -1.9054 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0459 -3.8707 -1.1883 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7769 -2.3856 -1.1113 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8894 -1.7270 -2.4483 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4313 -2.1929 -0.4589 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7083 -2.7265 -1.2548 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9423 -2.7093 -0.3369 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2802 -1.2625 -0.1603 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4484 -0.6343 -1.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5663 -3.2767 -2.0816 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6086 0.1997 0.6973 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1892 1.2993 0.0505 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6335 1.1740 -0.2289 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5431 2.2161 0.2942 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9280 3.2042 1.2527 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5507 3.5214 0.6495 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9286 4.6351 1.4433 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8137 2.3843 0.8444 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6704 4.3588 1.2697 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6813 1.6299 0.8687 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8442 1.1082 -1.6315 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9738 1.2134 0.4076 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9526 0.6592 1.4432 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1015 2.0277 1.6706 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4608 2.7469 2.0526 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9806 3.1378 0.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0157 4.3365 1.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2655 3.4719 0.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6276 2.1312 -1.3538 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9692 0.9749 0.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4123 1.4440 -1.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3388 -0.0596 -1.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7974 -1.3341 -0.8242 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1330 -2.7306 1.4190 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6215 -2.0321 0.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8193 -1.1898 2.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2895 -1.6572 1.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2828 0.6428 2.2629 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6260 1.2918 -0.1053 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1596 1.2692 1.6763 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0737 -1.1864 1.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2359 -0.0652 -0.9549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0801 0.6740 1.2947 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3792 -1.1185 1.6434 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2995 0.0801 -0.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6346 -2.3359 0.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8885 -1.9361 0.2759 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4931 -1.2505 -1.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8509 -4.1355 -0.4062 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2633 -3.6303 -2.9325 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5436 -5.1261 -2.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1761 -4.2325 -0.1340 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3039 -4.4400 -1.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5042 -2.3701 -3.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9557 -1.4880 -2.6358 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3367 -0.7789 -2.5185 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4643 -2.7545 0.5051 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6056 -3.7640 -1.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8586 -2.0467 -2.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6159 -3.2110 0.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7271 -3.2437 -0.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2672 0.1327 -1.5395 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8022 -1.4381 -2.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5615 -0.1472 -1.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1006 -2.4609 -1.9163 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6216 1.4537 -0.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9807 0.1832 0.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9540 2.8487 -0.5473 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7758 2.7715 2.2452 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6318 3.7274 -0.4197 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8829 4.8060 1.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9961 4.3722 2.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4904 5.5913 1.3256 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3226 4.9845 0.5749 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4712 1.6736 0.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7985 0.9390 -1.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0818 2.5017 1.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5887 2.1661 2.6522 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 1 0 6 7 1 0 6 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 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 27 1 0 14 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 33 35 1 0 32 36 1 0 31 37 1 0 30 38 1 0 9 39 1 0 5 40 1 1 40 41 1 0 41 2 1 0 39 5 1 0 25 8 1 0 35 29 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 6 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 6 50 1 6 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 1 9 55 1 1 10 56 1 0 10 57 1 0 11 58 1 1 12 59 1 6 13 60 1 0 13 61 1 0 14 62 1 6 15 63 1 1 16 64 1 0 16 65 1 0 17 66 1 1 18 67 1 0 18 68 1 0 19 69 1 0 19 70 1 0 21 71 1 0 21 72 1 0 21 73 1 0 22 74 1 1 23 75 1 0 23 76 1 0 24 77 1 0 24 78 1 0 26 79 1 0 26 80 1 0 26 81 1 0 27 82 1 0 29 83 1 6 30 84 1 1 31 85 1 6 32 86 1 1 33 87 1 6 34 88 1 0 34 89 1 0 34 90 1 0 36 91 1 0 37 92 1 0 38 93 1 0 41 94 1 0 41 95 1 0 M END

Standard InCHIKey	UJJOTHZQHRLIPY-JJBBQBTFSA-N
Standard InCHI	InChI=1S/C33H54O8/c1-16-6-11-33(38-15-16)17(2)26-25(41-33)14-22-20-13-24(40-30-29(37)28(36)27(35)18(3)39-30)23-12-19(34)7-9-31(23,4)21(20)8-10-32(22,26)5/h16-30,34-37H,6-15H2,1-5H3/t16-,17-,18+,19-,20+,21-,22-,23+,24-,25-,26-,27+,28-,29+,30-,31+,32-,33+/m0/s1
SMILES	C[C@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5C[C@@H]([C@H]6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.38	Volume:	589.751 ? Van der Waals volume.
Dense:	0.981	LogP:	4.221 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.138 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.493 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	36.0
TPSA:	117.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.367	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.881	Fsp³:	1.0
MCE-18:	173.182 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.772	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.052 ? 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:	0.204	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.47	MDCK Permeability:	-5.093
Pgp-inhibitor:	0.043	Pgp-substrate:	0.548
PAMPA:	0.878 ? 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%):	0.046	30% Bioavailability (F30%):	0.329
50% Bioavailability (F50%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.101
Plasma Protein Binding (PPB):	66.417%	Volume Distribution (VD):	-0.339
Fu:	29.882% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.809
BSEP inhibitor:	0.935

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:	0.032
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.909
HLM stability:	0.049 ? 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):

5.503

Half-life (T1/2):

2.963

ADMET: Toxicity

hERG Blockers:	0.081	hERG Blockers (10um):	0.2
Human Hepatotoxicity (H-HT):	0.492	Drug-induced Liver Injury (DILI):	0.687
AMES Toxicity:	0.491	Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.3	Skin Sensitization:	0.998
Carcinogencity:	0.302	Eye Corrosion:	0.001
Eye Irritation:	0.236	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.932
Hematotoxicity:	0.1	Drug-induced Nephrotoxicity:	0.653
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.149
A549 Cytotoxicity:	0.33	Hek293 Cytotoxicity:	0.665
BCF:	1.978 ? 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:	3.53 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.608 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.184 ? 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
NPO4703	Solanum hispidum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15217270]
NPO4703	Solanum hispidum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4703	Solanum hispidum	Species	Solanaceae	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
MIC	4

Activity Type	# Activity
Organism	4

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
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	400.0	ug.mL-1	PMID[24972008]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	25.0	ug.mL-1	PubChem BioAssay data set
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	50.0	ug.mL-1	PMID[18303847]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	400.0	ug.mL-1	DOI[10.1016/j.cropro.2012.12.021]

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 NPC149400 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	26271
0.1-0.2	21109
0.2-0.3	2138
0.3-0.4	171
0.4-0.5	76
0.5-0.6	63
0.6-0.7	17
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC144790
0.88	High Similarity	NPC131693
0.88	High Similarity	NPC475436
0.8732	High Similarity	NPC277715
0.8082	Intermediate Similarity	NPC88962
0.7468	Intermediate Similarity	NPC485594
0.7439	Intermediate Similarity	NPC312678
0.7439	Intermediate Similarity	NPC253268
0.7195	Intermediate Similarity	NPC485591
0.6988	Remote Similarity	NPC179859
0.6988	Remote Similarity	NPC473851
0.6875	Remote Similarity	NPC473774
0.6875	Remote Similarity	NPC481419
0.6875	Remote Similarity	NPC481417
0.6528	Remote Similarity	NPC296734
0.6463	Remote Similarity	NPC481420
0.6463	Remote Similarity	NPC481421
0.6452	Remote Similarity	NPC485603
0.6389	Remote Similarity	NPC248944
0.6389	Remote Similarity	NPC7479
0.6389	Remote Similarity	NPC257296
0.6237	Remote Similarity	NPC485605
0.6	Remote Similarity	NPC291547
0.6	Remote Similarity	NPC24960
0.6	Remote Similarity	NPC485593
0.6	Remote Similarity	NPC174024
0.5955	Remote Similarity	NPC477451
0.5934	Remote Similarity	NPC306131
0.5934	Remote Similarity	NPC200802
0.5914	Remote Similarity	NPC485595
0.5889	Remote Similarity	NPC222731
0.587	Remote Similarity	NPC485590
0.5795	Remote Similarity	NPC481424
0.5795	Remote Similarity	NPC481422
0.5761	Remote Similarity	NPC19400
0.5745	Remote Similarity	NPC470432
0.5745	Remote Similarity	NPC230507
0.5684	Remote Similarity	NPC70204
0.5625	Remote Similarity	NPC113044
0.5625	Remote Similarity	NPC283829
0.5625	Remote Similarity	NPC14704
0.5625	Remote Similarity	NPC161676
0.5618	Remote Similarity	NPC181845
0.5579	Remote Similarity	NPC6295
0.5556	Remote Similarity	NPC297348
0.5556	Remote Similarity	NPC325828
0.5556	Remote Similarity	NPC249204
0.5556	Remote Similarity	NPC48339
0.5556	Remote Similarity	NPC177834
0.5556	Remote Similarity	NPC141769
0.5556	Remote Similarity	NPC477547
0.5521	Remote Similarity	NPC195297
0.5517	Remote Similarity	NPC481418
0.5495	Remote Similarity	NPC294686
0.5495	Remote Similarity	NPC234352
0.5455	Remote Similarity	NPC470433
0.5455	Remote Similarity	NPC273290
0.5455	Remote Similarity	NPC46190
0.5455	Remote Similarity	NPC232044
0.5455	Remote Similarity	NPC171073
0.5455	Remote Similarity	NPC602423
0.5444	Remote Similarity	NPC481425
0.5444	Remote Similarity	NPC481426
0.5361	Remote Similarity	NPC141433
0.5347	Remote Similarity	NPC300557
0.5325	Remote Similarity	NPC227260
0.5319	Remote Similarity	NPC206003
0.5319	Remote Similarity	NPC473610
0.5294	Remote Similarity	NPC480555
0.5294	Remote Similarity	NPC150372
0.5263	Remote Similarity	NPC211354
0.5263	Remote Similarity	NPC107188
0.525	Remote Similarity	NPC305808
0.525	Remote Similarity	NPC481427
0.5244	Remote Similarity	NPC235126
0.5244	Remote Similarity	NPC242419
0.5243	Remote Similarity	NPC294129
0.5213	Remote Similarity	NPC250393
0.5155	Remote Similarity	NPC107962
0.5146	Remote Similarity	NPC485604
0.5143	Remote Similarity	NPC269297
0.5143	Remote Similarity	NPC222202
0.5094	Remote Similarity	NPC475333
0.5094	Remote Similarity	NPC32361
0.5094	Remote Similarity	NPC224098
0.5094	Remote Similarity	NPC208383
0.506	Remote Similarity	NPC161035
0.506	Remote Similarity	NPC170438
0.5053	Remote Similarity	NPC473616

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC149400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7595
0.1-0.2	1477
0.2-0.3	70
0.3-0.4	4
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
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
0.6389	Remote Similarity	NPD6928	Phase 2
0.5556	Remote Similarity	NPD8171	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