NPASS Compound

Natural Product: NPC111582

Natural Product ID	NPC111582
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	12Beta-Acetoxy-20(S),24(R)-Epoxy-3Alpha,25-Dihydroxydammarane
IUPAC Name	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-3-hydroxy-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-12-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL225562
PubChem CID	44421640
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 91 95 0 0 0 0 0 0 0 0999 V2000 1.6773 1.9370 3.8177 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5327 2.0470 2.3131 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0959 2.9802 1.6916 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7995 1.1488 1.6151 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5914 1.1378 0.1872 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8768 1.4820 0.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8081 0.3863 -0.2045 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1886 0.5261 0.4056 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2593 0.4041 1.8839 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7405 1.8960 0.0500 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6760 1.8644 -1.1430 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8872 1.0754 -0.7049 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5020 -0.3117 -0.2411 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1341 -0.6870 1.0555 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1001 -1.2621 -1.2982 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0331 -0.4819 -0.3258 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5884 -1.9033 -0.0544 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2170 -2.0354 -0.6686 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2404 -1.0153 -0.1230 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8929 -1.4858 1.2502 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0621 -0.9819 -1.0261 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3372 -0.4458 -2.4001 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6899 -2.2548 -1.1881 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0892 -1.7851 -1.5000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0432 -0.2235 -1.4510 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0256 -0.1334 -0.3371 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3938 0.3043 -1.1687 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4848 1.7917 -1.3568 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4980 -0.3372 -1.9730 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7249 0.1837 -1.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1414 0.4772 0.1389 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9309 -0.2140 1.2280 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3529 0.3027 1.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9588 -1.7050 1.0637 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2963 0.0991 2.4383 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8411 0.0326 0.1281 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8171 1.0827 -1.7134 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7268 2.3347 4.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7739 0.8354 4.0278 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5417 2.5040 4.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 1.9733 -0.1597 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2280 2.0877 0.9296 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9009 2.2351 -0.7851 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0733 0.4709 -1.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2441 0.8906 2.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3382 -0.5945 2.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5131 1.0343 2.3765 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9405 2.6494 -0.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3667 2.2719 0.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2204 1.5360 -2.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0402 2.9313 -1.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3131 1.5992 0.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4690 0.2734 1.5456 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1087 -1.2396 0.8973 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5419 -1.3237 1.7090 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3311 -2.2469 -0.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3950 -1.4165 -2.1251 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0320 -0.8559 -1.7035 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7697 -0.3349 -1.4215 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2673 -2.5661 -0.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6412 -2.1949 0.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2934 -2.0861 -1.7518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8304 -3.0445 -0.3392 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1587 -1.8942 1.3474 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4658 -2.4398 1.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9906 -0.7525 2.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2915 -0.9619 -3.1904 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2538 0.6482 -2.4656 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3726 -0.6853 -2.7845 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2707 -2.7737 -2.0997 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6204 -2.9615 -0.3686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4015 -2.0716 -2.5239 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7502 -2.1627 -0.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6851 0.1815 -2.3794 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5143 -0.7490 0.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3821 2.0617 -1.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5427 2.3846 -0.4514 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6325 2.1583 -1.9965 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4875 -0.0287 -3.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5228 -1.4237 -1.8935 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5059 -0.6093 -1.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1713 1.0561 -1.7113 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2489 1.5677 0.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0399 -0.3885 1.7725 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7143 0.3308 0.1846 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3565 1.3071 1.6671 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9137 -2.0787 0.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9168 -2.1682 2.0864 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0657 -2.0918 0.5307 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1282 1.0754 2.5215 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4578 1.8503 -1.5989 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 0 13 15 1 0 13 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 31 36 1 0 12 37 1 0 26 5 1 0 36 27 1 0 19 7 1 0 26 21 1 0 16 8 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 6 6 42 1 0 6 43 1 0 7 44 1 6 9 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 12 52 1 1 14 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 15 58 1 0 16 59 1 6 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 20 64 1 0 20 65 1 0 20 66 1 0 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 0 23 71 1 0 24 72 1 0 24 73 1 0 25 74 1 6 26 75 1 1 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 29 80 1 0 30 81 1 0 30 82 1 0 31 83 1 1 33 84 1 0 33 85 1 0 33 86 1 0 34 87 1 0 34 88 1 0 34 89 1 0 35 90 1 0 37 91 1 0 M END

Standard InCHIKey	YJMRWBFGYRRLNZ-SYURTPLQSA-N
Standard InCHI	InChI=1S/C32H54O5/c1-19(33)36-21-18-23-29(6)14-12-24(34)27(2,3)22(29)11-16-30(23,7)31(8)15-10-20(26(21)31)32(9)17-13-25(37-32)28(4,5)35/h20-26,34-35H,10-18H2,1-9H3/t20-,21+,22-,23+,24+,25+,26-,29-,30+,31+,32-/m0/s1
SMILES	CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@H](C(C)(C)[C@@H]3CC[C@@]2(C)[C@]2(C)CC[C@@H]([C@@H]12)[C@]1(C)CC[C@H](C(C)(C)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.4	Volume:	560.56 ? Van der Waals volume.
Dense:	0.925	LogP:	4.451 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.117 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.385 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	26.0
TPSA:	75.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.43	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.024	Fsp³:	0.969
MCE-18:	109.333 ? 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:	0.946	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:	0.239	Promiscuous compounds:	0.525

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.352	MDCK Permeability:	-5.039
Pgp-inhibitor:	0.936	Pgp-substrate:	0.018
PAMPA:	0.668 ? 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%):	0.013	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.807

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.716	MRP1:	0.973
Plasma Protein Binding (PPB):	92.685%	Volume Distribution (VD):	-0.372
Fu:	7.188% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.632
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.993	CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.991	CYP3A4-substrate:	0.872
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.99 ? 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):

11.571

Half-life (T1/2):

0.803

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.154
Human Hepatotoxicity (H-HT):	0.487	Drug-induced Liver Injury (DILI):	0.168
AMES Toxicity:	0.587	Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.545	Skin Sensitization:	0.967
Carcinogencity:	0.897	Eye Corrosion:	0.124
Eye Irritation:	0.695	Respiratory Toxicity:	0.659
Drug-induced Neurotoxicity:	0.028	Ototoxicity:	0.45
Hematotoxicity:	0.437	Drug-induced Nephrotoxicity:	0.666
Genotoxicity:	0.428	RPMI-8226 Immunitoxicity:	0.072
A549 Cytotoxicity:	0.157	Hek293 Cytotoxicity:	0.293
BCF:	1.161 ? 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:	3.671 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.381 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.568 ? 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	=	36500.0	nM	PMID[12662101]
NPT111	Cell line	K562	Homo sapiens	IC50	=	27500.0	nM	PMID[12662101]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	34200.0	nM	PMID[26920799]
NPT407	Cell line	COLO 205	Homo sapiens	IC50	=	36700.0	nM	PMID[26920799]

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 NPC111582 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	20612
0.1-0.2	23864
0.2-0.3	5011
0.3-0.4	307
0.4-0.5	44
0.5-0.6	10
0.6-0.7	8
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
0.7581	Intermediate Similarity	NPC286719
0.7581	Intermediate Similarity	NPC477286
0.6912	Remote Similarity	NPC56777
0.6613	Remote Similarity	NPC91387
0.6613	Remote Similarity	NPC231680
0.6613	Remote Similarity	NPC64081
0.6613	Remote Similarity	NPC270306
0.6567	Remote Similarity	NPC477283
0.6438	Remote Similarity	NPC201607
0.6119	Remote Similarity	NPC470070
0.5714	Remote Similarity	NPC477287
0.5588	Remote Similarity	NPC133596
0.5588	Remote Similarity	NPC11907
0.5507	Remote Similarity	NPC477285
0.5455	Remote Similarity	NPC486500
0.5373	Remote Similarity	NPC486502
0.5362	Remote Similarity	NPC190940
0.5294	Remote Similarity	NPC486499
0.5286	Remote Similarity	NPC474574
0.5068	Remote Similarity	NPC215968

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC111582 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7061
0.1-0.2	2025
0.2-0.3	63
0.3-0.4	1
0.4-0.5	0
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