NPASS Compound

Natural Product: NPC270306

Natural Product ID	NPC270306
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Epiocotillol
IUPAC Name	(3R,5R,8R,9R,10R,13R,14R,17S)-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms	3-Epiocotillol II
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL375698
PubChem CID	12313664
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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 85 89 0 0 0 0 0 0 0 0999 V2000 6.0636 1.5727 -1.0987 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4655 0.5088 -0.1590 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1547 0.7962 1.1800 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9877 0.6523 -0.0853 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5297 1.5390 1.0392 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0986 1.9158 0.7171 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2586 0.6330 0.7896 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3422 0.1365 2.1834 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7569 -0.2968 -0.2641 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8664 -1.5196 -0.3526 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4743 -0.9824 -0.8942 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0416 -0.2047 0.2071 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3834 0.3485 0.1430 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3592 1.4739 1.1564 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9153 1.5393 1.6796 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1581 0.9972 0.4788 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1844 2.0342 -0.5781 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5446 -0.5661 0.3183 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6103 -1.3174 1.5848 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7194 -1.5206 -0.8416 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2398 -1.5963 -1.0066 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7049 -0.7421 0.1483 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0704 -0.1724 -0.1288 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5203 0.6879 1.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1444 0.6001 -1.4081 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9672 -1.2412 -0.2020 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7253 0.2211 0.2431 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2149 -0.6283 -0.2083 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5464 -1.7022 0.7448 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6058 -1.1512 -1.6054 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0622 -1.4200 -1.7196 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9331 -0.8206 -0.6882 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2085 -0.6197 -1.2739 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7250 1.2726 -2.1239 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6360 2.5635 -0.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1567 1.5200 -1.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6033 0.4167 2.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1736 0.4079 1.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1665 1.9206 1.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6770 1.2263 -1.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1195 2.4957 0.9295 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7043 1.1766 2.0338 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6980 2.7146 1.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1208 2.1713 -0.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1025 1.0165 2.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5926 -0.6320 2.4582 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3112 -0.2217 2.5243 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6038 0.2392 -1.2500 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2265 -2.3022 -1.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6029 -1.9166 0.6678 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0735 -1.7929 -1.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1944 -0.2998 -1.7316 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9603 -0.8210 1.1547 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5242 0.8157 -0.8799 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5925 2.4481 0.6881 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0519 1.2942 2.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9005 0.8321 2.5399 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6094 2.5561 1.9244 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2219 2.3764 -0.8464 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3015 1.7813 -1.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2657 2.9693 -0.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0498 -2.3464 1.4193 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6407 -1.5127 2.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2924 -0.8270 2.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2738 -2.5013 -0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2910 -1.0557 -1.7649 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5255 -1.1614 -1.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5785 -2.6524 -0.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8046 -1.3722 1.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9813 1.6591 1.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3176 0.1364 1.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6116 0.8777 1.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3523 1.3744 -1.4772 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1111 1.1831 -1.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2147 -0.0596 -2.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6312 -1.9498 0.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5760 -2.1441 1.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1558 -1.4445 1.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0383 -2.6068 0.2723 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0642 -2.0868 -1.8484 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2394 -0.3931 -2.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2912 -2.5251 -1.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3940 -1.0426 -2.7282 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1602 -1.5032 0.1811 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7664 -1.4293 -1.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 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 6 13 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 22 27 1 0 9 28 1 0 28 29 1 1 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 2 1 0 28 4 1 0 16 7 1 0 27 18 1 0 16 12 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 6 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 6 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 1 13 54 1 6 14 55 1 0 14 56 1 0 15 57 1 0 15 58 1 0 17 59 1 0 17 60 1 0 17 61 1 0 19 62 1 0 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 22 69 1 1 24 70 1 0 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 25 75 1 0 26 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 31 83 1 0 32 84 1 1 33 85 1 0 M END

Standard InCHIKey	RQBNSDSKUAGBOI-WODPVNBQSA-N
Standard InCHI	InChI=1S/C30H52O3/c1-25(2)21-12-17-29(7)22(27(21,5)15-13-23(25)31)10-9-19-20(11-16-28(19,29)6)30(8)18-14-24(33-30)26(3,4)32/h19-24,31-32H,9-18H2,1-8H3/t19-,20+,21+,22-,23-,24-,27+,28-,29-,30+/m1/s1
SMILES	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@H](CC[C@@]34C)[C@]3(C)CC[C@H](C(C)(C)O)O3)[C@@]2(C)CC[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	460.39	Volume:	511.024 ? Van der Waals volume.
Dense:	0.901	LogP:	4.8 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.419 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.73 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	25.0
TPSA:	49.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.48	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.776	Fsp³:	1.0
MCE-18:	105.3 ? 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:	0.885	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.525	Promiscuous compounds:	0.307

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.116	MDCK Permeability:	-4.885
Pgp-inhibitor:	0.981	Pgp-substrate:	0.026
PAMPA:	0.042 ? 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%):	0.018	30% Bioavailability (F30%):	0.006
50% Bioavailability (F50%):	0.644

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.743	MRP1:	0.937
Plasma Protein Binding (PPB):	96.682%	Volume Distribution (VD):	-0.181
Fu:	4.316% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.949	BCRP inhibitor:	0.123
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.052	CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.991	CYP2D6-substrate:	0.295
CYP3A4-inhibitor:	0.929	CYP3A4-substrate:	0.19
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.404
HLM stability:	0.863 ? 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):

14.806

Half-life (T1/2):

1.053

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.208
Human Hepatotoxicity (H-HT):	0.505	Drug-induced Liver Injury (DILI):	0.053
AMES Toxicity:	0.357	Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.542	Skin Sensitization:	0.911
Carcinogencity:	0.838	Eye Corrosion:	0.039
Eye Irritation:	0.68	Respiratory Toxicity:	0.61
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.61
Hematotoxicity:	0.177	Drug-induced Nephrotoxicity:	0.634
Genotoxicity:	0.297	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.143	Hek293 Cytotoxicity:	0.46
BCF:	1.914 ? 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:	3.733 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.968 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.439 ? 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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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	8

Activity Type	# Activity
Cell line	8

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
NPT91	Cell line	KB	Homo sapiens	IC50	=	43400.0	nM	PMID[20022253]
NPT111	Cell line	K562	Homo sapiens	IC50	=	48500.0	nM	Open TG-GATES in vivo data: Organ Weight
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	57900.0	nM	Open TG-GATES in vivo data: Organ Weight
NPT407	Cell line	COLO 205	Homo sapiens	IC50	=	67500.0	nM	Open TG-GATES in vivo data: Organ Weight
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[17850214]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[17190469]
NPT81	Cell line	A549	Homo sapiens	IC50	>	50000.0	nM	DrugMatrix in vivo data: Biochemistry
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[18077363]

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 NPC270306 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	22921
0.1-0.2	23368
0.2-0.3	3046
0.3-0.4	375
0.4-0.5	93
0.5-0.6	33
0.6-0.7	13
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC91387
1.0	High Similarity	NPC231680
0.8333	Intermediate Similarity	NPC133596
0.8333	Intermediate Similarity	NPC11907
0.7455	Intermediate Similarity	NPC64081
0.6897	Remote Similarity	NPC245029
0.6897	Remote Similarity	NPC31302
0.6786	Remote Similarity	NPC58631
0.678	Remote Similarity	NPC190940
0.678	Remote Similarity	NPC292458
0.678	Remote Similarity	NPC217559
0.678	Remote Similarity	NPC268578
0.6613	Remote Similarity	NPC111582
0.625	Remote Similarity	NPC103782
0.6032	Remote Similarity	NPC250687
0.6032	Remote Similarity	NPC48824
0.6032	Remote Similarity	NPC148740
0.6032	Remote Similarity	NPC102156
0.5938	Remote Similarity	NPC80700
0.5873	Remote Similarity	NPC474574
0.5846	Remote Similarity	NPC254572
0.5846	Remote Similarity	NPC229407
0.5846	Remote Similarity	NPC269267
0.5833	Remote Similarity	NPC201725
0.5797	Remote Similarity	NPC114378
0.5758	Remote Similarity	NPC311642
0.5758	Remote Similarity	NPC164289
0.5758	Remote Similarity	NPC100366
0.5758	Remote Similarity	NPC471747
0.5758	Remote Similarity	NPC242771
0.5636	Remote Similarity	NPC232112
0.5517	Remote Similarity	NPC480925
0.5517	Remote Similarity	NPC48079
0.5484	Remote Similarity	NPC81074
0.5484	Remote Similarity	NPC477282
0.5246	Remote Similarity	NPC245869
0.5231	Remote Similarity	NPC477577
0.5161	Remote Similarity	NPC285761
0.5161	Remote Similarity	NPC34930
0.5152	Remote Similarity	NPC477285
0.5139	Remote Similarity	NPC479791
0.5085	Remote Similarity	NPC142712
0.5082	Remote Similarity	NPC97534
0.5082	Remote Similarity	NPC195155
0.5079	Remote Similarity	NPC602784
0.5077	Remote Similarity	NPC49599
0.5077	Remote Similarity	NPC49627
0.5077	Remote Similarity	NPC477508
0.5077	Remote Similarity	NPC603388
0.5075	Remote Similarity	NPC131665
0.5075	Remote Similarity	NPC255387

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC270306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7293
0.1-0.2	1796
0.2-0.3	59
0.3-0.4	1
0.4-0.5	1
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