NPASS Compound

Natural Product: NPC193382

Natural Product ID	NPC193382
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cannogenol-3-O-Alpha-L-Rhamnoside
IUPAC Name	3-[(3S,5R,8R,9S,10R,13R,14S,17R)-14-hydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL400877
PubChem CID	21123891
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 82 87 0 0 0 0 0 0 0 0999 V2000 7.9428 0.4360 -1.1377 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9206 0.1893 -0.0195 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1421 1.2694 0.9989 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0237 1.3220 2.0228 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0736 0.1807 1.6583 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6213 0.4464 0.2411 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6841 0.2015 -0.6115 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.3980 -0.1692 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4764 0.2664 -0.6283 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0922 -0.1596 -2.0375 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5917 -0.0800 -2.2381 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1376 -1.1692 -1.4398 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0980 -2.4190 -2.2491 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6990 -2.3280 -3.4994 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7800 -1.4145 -0.2337 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1149 -2.2429 0.8172 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0887 -1.5016 1.3152 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0530 -1.2868 0.1940 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4749 -0.6772 -1.0301 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5016 -0.8839 -2.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8248 -0.2675 -1.8197 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2475 -0.1687 -0.3938 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3805 -1.1624 -0.2022 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7596 1.2248 -0.1177 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6329 1.9609 0.5717 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7536 0.8919 1.1823 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2091 -0.4410 0.6446 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7333 -1.1438 1.7606 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0276 1.3213 0.5975 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1655 1.8355 0.0951 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2215 1.7729 1.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3975 2.1841 0.8791 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6990 1.2013 2.2106 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3445 0.9143 1.9856 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3037 -0.0974 0.2579 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0223 0.1275 2.5680 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3259 2.5042 1.8280 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3178 0.9239 1.7001 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8939 0.8204 -0.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4979 1.1952 -1.8005 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0561 -0.5139 -1.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2101 -0.7891 0.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2763 2.2281 0.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3942 1.2240 3.0622 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6590 -0.7507 1.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 1.5236 0.1258 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6039 1.3612 -0.5815 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4929 -1.1591 -2.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5464 0.5555 -2.7308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3840 -0.1267 -3.3104 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2580 0.8854 -1.8048 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4356 -3.3192 -1.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9940 -2.6278 -2.4484 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0333 -1.9444 -4.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6390 -2.0034 -0.6294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1787 -3.2037 0.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8577 -2.4551 1.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7515 -0.5699 1.8014 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5892 -2.1501 2.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4635 -2.2920 -0.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3829 0.4465 -0.9283 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6147 -1.9803 -2.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0616 -0.4984 -3.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7998 0.7595 -2.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5849 -0.8069 -2.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2501 -1.7989 0.6862 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3695 -0.7147 -0.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4047 -1.9003 -1.0626 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8659 1.7614 -1.1124 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0548 2.6167 -0.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0842 2.6319 1.3320 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7201 1.1456 0.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8730 0.9875 2.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1604 -0.9027 2.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2471 2.2318 -0.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2568 -0.2033 2.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6768 1.4156 2.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5111 0.6902 0.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6181 -0.2339 1.3036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2079 0.6438 3.3959 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7281 3.0713 1.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1040 1.4163 1.3630 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 6 13 14 1 0 12 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 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 24 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 15 35 1 0 5 36 1 0 4 37 1 0 3 38 1 0 7 2 1 0 35 9 1 0 19 12 1 0 27 22 1 0 34 29 1 0 27 18 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 1 3 43 1 6 4 44 1 1 5 45 1 6 6 46 1 1 9 47 1 6 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 13 52 1 0 13 53 1 0 14 54 1 0 15 55 1 6 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 6 19 61 1 1 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 6 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 28 74 1 0 30 75 1 0 34 76 1 0 34 77 1 0 35 78 1 0 35 79 1 0 36 80 1 0 37 81 1 0 38 82 1 0 M END

Standard InCHIKey	WPVGSIBYLZQSIK-XUAZSLIYSA-N
Standard InCHI	InChI=1S/C29H44O9/c1-15-23(32)24(33)25(34)26(37-15)38-18-5-9-28(14-30)17(12-18)3-4-21-20(28)6-8-27(2)19(7-10-29(21,27)35)16-11-22(31)36-13-16/h11,15,17-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t15-,17+,18-,19+,20-,21+,23-,24+,25+,26-,27+,28+,29-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(CO)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.3	Volume:	532.64 ? Van der Waals volume.
Dense:	1.007	LogP:	0.85 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.549 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.884 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	32.0
TPSA:	145.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.266	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.193	Fsp³:	0.897
MCE-18:	110.618 ? 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:	0.819	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? 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:	0.149	Promiscuous compounds:	0.218

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.142	MDCK Permeability:	-5.186
Pgp-inhibitor:	0.0	Pgp-substrate:	0.928
PAMPA:	0.999 ? 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):	0.384
20% Bioavailability (F20%):	0.465	30% Bioavailability (F30%):	0.856
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.475	MRP1:	0.165
Plasma Protein Binding (PPB):	72.549%	Volume Distribution (VD):	-0.456
Fu:	26.611% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.315
BSEP inhibitor:	0.012

ADMET: Metabolism

CYP1A2-inhibitor:	0.366	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.946	CYP3A4-substrate:	0.561
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.026
HLM stability:	0.001 ? 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):

1.786

Half-life (T1/2):

3.845

ADMET: Toxicity

hERG Blockers:	0.164	hERG Blockers (10um):	0.715
Human Hepatotoxicity (H-HT):	0.668	Drug-induced Liver Injury (DILI):	0.878
AMES Toxicity:	0.802	Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.769	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.976
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.843
Hematotoxicity:	0.686	Drug-induced Nephrotoxicity:	0.978
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.781
A549 Cytotoxicity:	0.35	Hek293 Cytotoxicity:	0.951
BCF:	0.648 ? 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:	3.187 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.485 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.754 ? 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
NPO587	Saussurea stella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17844995]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO587	Saussurea stella	Species	Asteraceae	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
IC50	2
Inhibition	1

Activity Type	# Activity
Cell line	1
Non-molecular	2

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
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	28.0	nM	PMID[18076141]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	77.0	nM	PMID[17844995]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	82.4	%	PMID[24033101]

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 NPC193382 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	13754
0.1-0.2	29701
0.2-0.3	5480
0.3-0.4	699
0.4-0.5	48
0.5-0.6	80
0.6-0.7	51
0.7-0.8	1
0.8-0.85	8
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76572
0.9041	High Similarity	NPC77299
0.9041	High Similarity	NPC480906
0.8514	High Similarity	NPC99620
0.8289	Intermediate Similarity	NPC469750
0.8205	Intermediate Similarity	NPC471353
0.8148	Intermediate Similarity	NPC32177
0.8148	Intermediate Similarity	NPC469756
0.8148	Intermediate Similarity	NPC275901
0.8052	Intermediate Similarity	NPC5311
0.8049	Intermediate Similarity	NPC480910
0.8049	Intermediate Similarity	NPC480909
0.7857	Intermediate Similarity	NPC486135
0.7857	Intermediate Similarity	NPC486137
0.7831	Intermediate Similarity	NPC240070
0.775	Intermediate Similarity	NPC305574
0.7722	Intermediate Similarity	NPC480914
0.7692	Intermediate Similarity	NPC196429
0.7595	Intermediate Similarity	NPC157376
0.7595	Intermediate Similarity	NPC142066
0.7595	Intermediate Similarity	NPC603972
0.7381	Intermediate Similarity	NPC30483
0.7381	Intermediate Similarity	NPC470897
0.7349	Intermediate Similarity	NPC480907
0.7342	Intermediate Similarity	NPC99728
0.7342	Intermediate Similarity	NPC87250
0.7342	Intermediate Similarity	NPC244402
0.7342	Intermediate Similarity	NPC50305
0.7333	Intermediate Similarity	NPC486136
0.7317	Intermediate Similarity	NPC483822
0.7294	Intermediate Similarity	NPC236973
0.716	Intermediate Similarity	NPC17896
0.716	Intermediate Similarity	NPC469755
0.716	Intermediate Similarity	NPC284406
0.716	Intermediate Similarity	NPC197707
0.716	Intermediate Similarity	NPC251866
0.716	Intermediate Similarity	NPC480915
0.7093	Intermediate Similarity	NPC292467
0.7045	Intermediate Similarity	NPC486143
0.7045	Intermediate Similarity	NPC486142
0.7045	Intermediate Similarity	NPC486149
0.7011	Intermediate Similarity	NPC188234
0.6914	Remote Similarity	NPC471633
0.6905	Remote Similarity	NPC179412
0.6905	Remote Similarity	NPC471356
0.6829	Remote Similarity	NPC84987
0.6778	Remote Similarity	NPC232785
0.6778	Remote Similarity	NPC486139
0.6703	Remote Similarity	NPC486146
0.6667	Remote Similarity	NPC199428
0.6667	Remote Similarity	NPC125077
0.6667	Remote Similarity	NPC109448
0.6667	Remote Similarity	NPC310341
0.6596	Remote Similarity	NPC486144
0.6596	Remote Similarity	NPC486145
0.6596	Remote Similarity	NPC486147
0.6596	Remote Similarity	NPC486148
0.6552	Remote Similarity	NPC72260
0.6522	Remote Similarity	NPC329986
0.6522	Remote Similarity	NPC140092
0.6452	Remote Similarity	NPC486138
0.6452	Remote Similarity	NPC276838
0.6429	Remote Similarity	NPC309034
0.6421	Remote Similarity	NPC475590
0.6395	Remote Similarity	NPC250556
0.6333	Remote Similarity	NPC27363
0.6289	Remote Similarity	NPC120390
0.6289	Remote Similarity	NPC74259
0.6289	Remote Similarity	NPC475419
0.6279	Remote Similarity	NPC84949
0.6279	Remote Similarity	NPC480562
0.6279	Remote Similarity	NPC74945
0.6279	Remote Similarity	NPC31354
0.6279	Remote Similarity	NPC69576
0.625	Remote Similarity	NPC471354
0.625	Remote Similarity	NPC27507
0.6237	Remote Similarity	NPC469749
0.6234	Remote Similarity	NPC222875
0.6234	Remote Similarity	NPC25177
0.6224	Remote Similarity	NPC474908
0.6224	Remote Similarity	NPC486134
0.6224	Remote Similarity	NPC486141
0.6207	Remote Similarity	NPC77319
0.6207	Remote Similarity	NPC471351
0.6207	Remote Similarity	NPC471355
0.6118	Remote Similarity	NPC473852
0.6087	Remote Similarity	NPC32793
0.6087	Remote Similarity	NPC116075
0.604	Remote Similarity	NPC474423
0.6023	Remote Similarity	NPC83287
0.6022	Remote Similarity	NPC475629
0.6	Remote Similarity	NPC158344
0.6	Remote Similarity	NPC486150
0.5957	Remote Similarity	NPC208193
0.5955	Remote Similarity	NPC9499
0.5955	Remote Similarity	NPC471360
0.5955	Remote Similarity	NPC469751
0.5955	Remote Similarity	NPC93883
0.5955	Remote Similarity	NPC471361
0.5955	Remote Similarity	NPC86159
0.5955	Remote Similarity	NPC469752
0.5955	Remote Similarity	NPC469754
0.5955	Remote Similarity	NPC70542
0.5914	Remote Similarity	NPC475556
0.5914	Remote Similarity	NPC311706
0.5914	Remote Similarity	NPC486130
0.5897	Remote Similarity	NPC480913
0.5862	Remote Similarity	NPC219085
0.5851	Remote Similarity	NPC231518
0.5851	Remote Similarity	NPC486127
0.5851	Remote Similarity	NPC488944
0.5814	Remote Similarity	NPC474418
0.5789	Remote Similarity	NPC55532
0.5778	Remote Similarity	NPC484202
0.5769	Remote Similarity	NPC286809
0.5684	Remote Similarity	NPC264336
0.567	Remote Similarity	NPC146857
0.567	Remote Similarity	NPC247190
0.5591	Remote Similarity	NPC173555
0.5556	Remote Similarity	NPC476221
0.5556	Remote Similarity	NPC243196
0.5556	Remote Similarity	NPC477709
0.5556	Remote Similarity	NPC486132
0.5556	Remote Similarity	NPC486131
0.5521	Remote Similarity	NPC610296
0.5506	Remote Similarity	NPC486129
0.55	Remote Similarity	NPC479360
0.55	Remote Similarity	NPC486128
0.55	Remote Similarity	NPC479359
0.55	Remote Similarity	NPC488943
0.55	Remote Similarity	NPC488942
0.5495	Remote Similarity	NPC146456
0.5484	Remote Similarity	NPC329905
0.5474	Remote Similarity	NPC40749
0.5444	Remote Similarity	NPC486126
0.5444	Remote Similarity	NPC479356
0.5444	Remote Similarity	NPC479355
0.5437	Remote Similarity	NPC117445
0.5437	Remote Similarity	NPC308262
0.54	Remote Similarity	NPC475219
0.5385	Remote Similarity	NPC10823
0.5376	Remote Similarity	NPC193893
0.5375	Remote Similarity	NPC268829
0.5375	Remote Similarity	NPC295110
0.5347	Remote Similarity	NPC488938
0.5347	Remote Similarity	NPC488937
0.5306	Remote Similarity	NPC59288
0.5288	Remote Similarity	NPC486140
0.5288	Remote Similarity	NPC329675
0.5288	Remote Similarity	NPC194716
0.5275	Remote Similarity	NPC34390
0.5269	Remote Similarity	NPC277374
0.5258	Remote Similarity	NPC479353
0.5258	Remote Similarity	NPC479354
0.5238	Remote Similarity	NPC486133
0.5217	Remote Similarity	NPC480908
0.5217	Remote Similarity	NPC604978
0.5204	Remote Similarity	NPC488941
0.5204	Remote Similarity	NPC488940
0.5189	Remote Similarity	NPC488945
0.5189	Remote Similarity	NPC488946
0.5185	Remote Similarity	NPC187302
0.5161	Remote Similarity	NPC88668
0.5161	Remote Similarity	NPC180079
0.5122	Remote Similarity	NPC196931
0.5122	Remote Similarity	NPC10232
0.5119	Remote Similarity	NPC196471
0.5109	Remote Similarity	NPC6108
0.5109	Remote Similarity	NPC89514
0.5109	Remote Similarity	NPC99080
0.5104	Remote Similarity	NPC5883
0.5102	Remote Similarity	NPC608063
0.5094	Remote Similarity	NPC329784

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC193382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5773
0.1-0.2	3219
0.2-0.3	136
0.3-0.4	7
0.4-0.5	5
0.5-0.6	5
0.6-0.7	4
0.7-0.8	1
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
0.716	Intermediate Similarity	NPD7319	Approved
0.6552	Remote Similarity	NPD8294	Phase 4
0.6395	Remote Similarity	NPD7507	Pre-clinical
0.6023	Remote Similarity	NPD7327	Approved
0.6023	Remote Similarity	NPD7328	Phase 4
0.5851	Remote Similarity	NPD8033	Approved
0.5789	Remote Similarity	NPD8377	Phase 4
0.5591	Remote Similarity	NPD8296	Phase 4
0.5161	Remote Similarity	NPD8335	Phase 4
0.5106	Remote Similarity	NPD8380	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