NPASS Compound

Natural Product: NPC190940

Natural Product ID	NPC190940
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Epiocotillol Ii Acetate
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-yl] acetate
Synonyms	3-Epiocotillol II acetate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL224087
PubChem CID	44421636
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 90 94 0 0 0 0 0 0 0 0999 V2000 9.1610 -1.1124 -0.0855 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8026 -1.1097 0.5062 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6448 -1.2193 1.7475 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7126 -0.9868 -0.3052 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3559 -0.9732 0.1724 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6532 -2.0955 -0.5060 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2191 -1.7820 -0.9009 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5789 -0.7916 0.0778 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7119 -1.3795 1.4338 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3385 0.5043 -0.1158 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8284 1.5475 0.8468 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4112 1.8610 0.4378 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5365 0.6719 0.2928 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0342 0.2873 1.6492 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1936 -0.5184 -0.3865 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2823 -1.6889 -0.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0965 -1.3784 -0.9133 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 -0.0679 -0.4444 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7746 0.4943 -1.2231 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7348 1.9817 -0.8343 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3783 2.2345 -0.2188 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6131 1.0255 -0.6097 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2143 1.1779 -2.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1320 -0.0710 -1.0149 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1894 -1.5282 -1.3727 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0868 0.6500 -1.9732 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3565 0.7292 -1.1520 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0074 -0.1310 0.0439 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8607 0.2225 1.2371 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4465 -0.6451 2.4074 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2909 -0.1604 0.8955 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8151 1.5746 1.5292 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6653 0.1891 0.2425 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8107 0.3801 -0.1724 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3853 0.7329 -1.5525 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4582 1.3739 0.8011 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1161 -1.2539 -1.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8228 -1.8767 0.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6234 -0.1195 0.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4427 -1.0781 1.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7303 -3.0299 0.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1698 -2.3579 -1.4765 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6721 -2.7611 -0.7638 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1491 -1.4219 -1.9457 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1184 -0.7082 2.2050 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7502 -1.7789 1.8594 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3855 -2.2892 1.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0109 0.8843 -1.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4215 2.4768 0.6521 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9481 1.2992 1.8961 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4238 2.5509 -0.4308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9851 2.4827 1.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7711 0.9741 2.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3889 -0.7230 1.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8717 0.4448 2.3934 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2954 -0.1996 -1.4699 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2373 -2.2583 0.5586 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7064 -2.4331 -1.1293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7488 -2.1831 -0.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1206 -1.4764 -2.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9668 -0.1167 0.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5542 0.3988 -2.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8736 2.6285 -1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5334 2.1151 -0.0745 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8916 3.1145 -0.7362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4144 2.4906 0.8323 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8985 1.9198 -2.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2963 0.2632 -2.6545 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7982 1.6558 -2.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1143 -2.1116 -0.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4554 -1.8193 -2.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1896 -1.7803 -1.8529 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2516 0.0714 -2.8864 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7541 1.6857 -2.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5660 1.7743 -0.8107 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1892 0.3052 -1.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1734 -1.2042 -0.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9217 -1.6526 2.2270 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3679 -0.7931 2.4086 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8692 -0.2606 3.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8408 -0.4260 1.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8270 0.6584 0.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2527 -1.0891 0.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6335 1.6762 2.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8171 -0.1390 -2.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1153 1.5369 -1.5178 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4952 1.0407 -2.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4217 2.3658 0.2756 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9825 1.3744 1.7785 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5555 1.1543 0.8919 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 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 19 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 28 33 1 0 10 34 1 0 34 35 1 0 34 36 1 0 34 5 1 0 15 8 1 0 22 18 1 0 33 24 1 0 22 13 1 0 1 37 1 0 1 38 1 0 1 39 1 0 5 40 1 1 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 9 45 1 0 9 46 1 0 9 47 1 0 10 48 1 6 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 14 53 1 0 14 54 1 0 14 55 1 0 15 56 1 6 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 1 19 62 1 6 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 23 67 1 0 23 68 1 0 23 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 28 77 1 6 30 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 31 82 1 0 31 83 1 0 32 84 1 0 35 85 1 0 35 86 1 0 35 87 1 0 36 88 1 0 36 89 1 0 36 90 1 0 M END

Standard InCHIKey	MYKPKZPRXSYQEQ-DGCVXKJQSA-N
Standard InCHI	InChI=1S/C32H54O4/c1-20(33)35-25-14-16-29(6)23(27(25,2)3)13-18-31(8)24(29)11-10-21-22(12-17-30(21,31)7)32(9)19-15-26(36-32)28(4,5)34/h21-26,34H,10-19H2,1-9H3/t21-,22+,23+,24-,25-,26-,29+,30-,31-,32+/m1/s1
SMILES	CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC[C@@H]2[C@H](CC[C@@]32C)[C@]2(C)CC[C@H](C(C)(C)O)O2)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.4	Volume:	551.77 ? Van der Waals volume.
Dense:	0.911	LogP:	5.369 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.246 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.362 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	26.0
TPSA:	55.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.411	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.806	Fsp³:	0.969
MCE-18:	106.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.937	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.529	Promiscuous compounds:	0.422

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982	MDCK Permeability:	-4.875
Pgp-inhibitor:	1.0	Pgp-substrate:	0.004
PAMPA:	0.021 ? 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%):	0.128	30% Bioavailability (F30%):	0.161
50% Bioavailability (F50%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232	MRP1:	0.883
Plasma Protein Binding (PPB):	90.28%	Volume Distribution (VD):	-0.293
Fu:	8.618% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.771
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.042	CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.884	CYP2D6-substrate:	0.316
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.728
HLM stability:	0.957 ? 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):

10.847

Half-life (T1/2):

0.464

ADMET: Toxicity

hERG Blockers:	0.173	hERG Blockers (10um):	0.403
Human Hepatotoxicity (H-HT):	0.623	Drug-induced Liver Injury (DILI):	0.38
AMES Toxicity:	0.396	Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	0.587	Skin Sensitization:	0.991
Carcinogencity:	0.927	Eye Corrosion:	0.413
Eye Irritation:	0.878	Respiratory Toxicity:	0.597
Drug-induced Neurotoxicity:	0.111	Ototoxicity:	0.383
Hematotoxicity:	0.498	Drug-induced Nephrotoxicity:	0.52
Genotoxicity:	0.751	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.085	Hek293 Cytotoxicity:	0.527
BCF:	2.473 ? 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:	4.731 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.807 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.581 ? 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]
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	4

Activity Type	# Activity
Cell line	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
NPT91	Cell line	KB	Homo sapiens	IC50	=	44800.0	nM	PMID[26000707]
NPT111	Cell line	K562	Homo sapiens	IC50	=	41600.0	nM	PMID[25080196]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	47500.0	nM	PMID[18491867]
NPT407	Cell line	COLO 205	Homo sapiens	IC50	=	54200.0	nM	PMID[18491867]

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 NPC190940 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	21455
0.1-0.2	23824
0.2-0.3	4212
0.3-0.4	280
0.4-0.5	35
0.5-0.6	23
0.6-0.7	21
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8448	Intermediate Similarity	NPC103782
0.7778	Intermediate Similarity	NPC114378
0.7458	Intermediate Similarity	NPC477285
0.7213	Intermediate Similarity	NPC286719
0.7213	Intermediate Similarity	NPC477286
0.7193	Intermediate Similarity	NPC488509
0.6833	Remote Similarity	NPC245029
0.6833	Remote Similarity	NPC31302
0.678	Remote Similarity	NPC91387
0.678	Remote Similarity	NPC231680
0.678	Remote Similarity	NPC270306
0.6721	Remote Similarity	NPC292458
0.6721	Remote Similarity	NPC217559
0.6721	Remote Similarity	NPC268578
0.6721	Remote Similarity	NPC488510
0.6452	Remote Similarity	NPC133596
0.6452	Remote Similarity	NPC11907
0.6324	Remote Similarity	NPC56777
0.625	Remote Similarity	NPC250687
0.625	Remote Similarity	NPC48824
0.625	Remote Similarity	NPC148740
0.625	Remote Similarity	NPC102156
0.623	Remote Similarity	NPC302280
0.619	Remote Similarity	NPC13494
0.6154	Remote Similarity	NPC212453
0.6061	Remote Similarity	NPC488503
0.6061	Remote Similarity	NPC269267
0.597	Remote Similarity	NPC311642
0.597	Remote Similarity	NPC164289
0.597	Remote Similarity	NPC100366
0.597	Remote Similarity	NPC471747
0.597	Remote Similarity	NPC242771
0.5909	Remote Similarity	NPC155531
0.589	Remote Similarity	NPC201607
0.5846	Remote Similarity	NPC488508
0.5821	Remote Similarity	NPC215968
0.5735	Remote Similarity	NPC477283
0.5588	Remote Similarity	NPC254572
0.5588	Remote Similarity	NPC229407
0.5556	Remote Similarity	NPC479791
0.5455	Remote Similarity	NPC61107
0.5441	Remote Similarity	NPC80700
0.5373	Remote Similarity	NPC5280
0.5362	Remote Similarity	NPC111582
0.5362	Remote Similarity	NPC180204
0.5362	Remote Similarity	NPC477287
0.5303	Remote Similarity	NPC220379
0.5231	Remote Similarity	NPC305835
0.5217	Remote Similarity	NPC168231
0.5152	Remote Similarity	NPC84868

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6820
0.1-0.2	2256
0.2-0.3	71
0.3-0.4	2
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