NPASS Compound

Natural Product: NPC187933

Natural Product ID	NPC187933
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta,6Beta,19Alpha-Trihydroxyurs-12-En-23-Oxo-28-Oic Acid
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-1,10-dihydroxy-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL463636
PubChem CID	14314241
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 81 85 0 0 0 0 0 0 0 0999 V2000 5.8715 -0.7045 2.8177 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2569 -1.1418 1.8681 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9119 -0.2848 0.6646 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5884 -0.9808 -0.5211 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4854 1.0587 0.9240 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6996 1.1451 0.1985 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6628 2.2273 0.5532 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1933 2.0225 0.5191 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7786 0.7427 -0.2364 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4311 -0.3411 0.5690 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9447 -1.6488 0.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5039 -1.7866 0.5726 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6931 -0.7362 -0.1458 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3030 0.6214 -0.1694 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5814 1.4303 -1.2424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8491 1.0866 -1.3010 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4710 0.1913 -0.5396 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6957 -0.5819 0.5044 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5887 0.2126 1.7983 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3521 -1.8697 0.8453 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3543 -2.3941 -0.1092 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3704 -1.4412 -0.6322 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9238 -0.0161 -0.7570 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7387 0.9499 0.0792 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2166 2.3611 -0.1749 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6732 0.7230 1.4260 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1743 0.8449 -0.4058 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6694 -0.5279 -0.1154 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6209 -1.5209 0.2389 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0103 1.9206 0.2655 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8125 -1.9915 -1.9617 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3420 -3.0524 -2.4050 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7743 -1.3051 -2.7289 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4477 -1.2524 -1.5487 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3611 0.9257 -1.6008 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9261 -2.1661 1.8369 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8326 -1.3154 -1.2742 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1274 -1.9043 -0.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3630 -0.3278 -0.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8203 1.1854 1.9976 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5801 1.7320 -0.5815 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9879 2.7017 -0.4212 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8285 3.0709 1.2918 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7116 2.8987 0.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8020 1.8781 1.5685 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0305 -0.2309 1.6209 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8228 -1.5836 -1.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5481 -2.5167 0.3475 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4462 -1.7358 1.6586 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2093 -2.8002 0.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9846 1.1344 0.7873 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 2.5219 -0.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0780 1.3715 -2.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4425 1.6176 -2.0376 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3784 -0.0208 2.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8094 1.2701 1.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3440 -0.1721 2.5554 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8770 -1.8085 1.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6218 -2.7144 1.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9063 -3.0344 -0.9314 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9398 -3.1945 0.4473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1645 0.2961 -1.8209 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8576 3.0139 0.4897 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2042 2.4771 0.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4110 2.6880 -1.2006 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3659 1.5238 1.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1710 1.1001 -1.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2709 -0.8787 -1.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3951 -0.4737 0.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3625 -1.5420 1.3153 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0499 -2.5452 0.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0673 1.6358 0.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7235 2.0857 1.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8343 2.8823 -0.2710 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2784 -1.8666 -3.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5968 -1.2825 -1.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8356 -2.3014 -1.6870 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9691 -0.6596 -2.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4614 1.0464 -1.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2199 0.1231 -2.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0190 1.9349 -1.9766 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 6 3 5 1 0 5 6 1 0 5 7 1 0 7 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 2 0 17 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 24 25 1 0 24 26 1 1 24 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 22 31 1 6 31 32 2 0 31 33 1 0 13 34 1 6 9 35 1 6 10 3 1 0 18 13 1 0 29 22 1 0 14 9 1 0 23 17 1 0 2 36 1 0 4 37 1 0 4 38 1 0 4 39 1 0 5 40 1 1 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 10 46 1 1 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 14 51 1 1 15 52 1 0 15 53 1 0 16 54 1 0 19 55 1 0 19 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 21 60 1 0 21 61 1 0 23 62 1 6 25 63 1 0 25 64 1 0 25 65 1 0 26 66 1 0 27 67 1 6 28 68 1 0 28 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 M END

Standard InCHIKey	ZXRXQOHNSRCNHE-LTFXOGOQSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-18-9-14-30(24(33)34)16-15-27(4)19(23(30)29(18,6)35)7-8-21-25(2)12-11-22(32)26(3,17-31)20(25)10-13-28(21,27)5/h7,17-18,20-23,32,35H,8-16H2,1-6H3,(H,33,34)/t18-,20-,21-,22+,23-,25+,26+,27-,28-,29-,30+/m1/s1
SMILES	O=C[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@@H](CC1)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	2.803 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.687 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.333 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.36	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.11	Fsp³:	0.867
MCE-18:	108.571 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.635	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.041 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.324	Promiscuous compounds:	0.047

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.578	MDCK Permeability:	-5.144
Pgp-inhibitor:	0.0	Pgp-substrate:	0.013
PAMPA:	1.0 ? 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%):	0.273	30% Bioavailability (F30%):	0.011
50% Bioavailability (F50%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225	MRP1:	0.984
Plasma Protein Binding (PPB):	86.112%	Volume Distribution (VD):	-0.427
Fu:	11.281% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.061	BCRP inhibitor:	0.007
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.345	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.153	CYP3A4-substrate:	0.39
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.029
HLM stability:	0.021 ? 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):

3.796

Half-life (T1/2):

0.983

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.726	Drug-induced Liver Injury (DILI):	0.635
AMES Toxicity:	0.727	Rat Oral Acute Toxicity:	0.673
Maximum Recommended Daily Dose:	0.596	Skin Sensitization:	0.998
Carcinogencity:	0.974	Eye Corrosion:	0.004
Eye Irritation:	0.324	Respiratory Toxicity:	0.933
Drug-induced Neurotoxicity:	0.102	Ototoxicity:	0.605
Hematotoxicity:	0.667	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.074
A549 Cytotoxicity:	0.466	Hek293 Cytotoxicity:	0.31
BCF:	0.559 ? 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:	3.552 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.113 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.423 ? 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
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np1003593]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919590]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	Twigs	Yangming mountain, Taiwan	2008-APR	PMID[20873721]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[4421158]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	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
Activity	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
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	93.0	%	PMID[20873721]
NPT397	Cell line	NCI-H460	Homo sapiens	Activity	=	103.0	%	PMID[20873721]
NPT139	Cell line	HT-29	Homo sapiens	Activity	=	91.0	%	PMID[20873721]
NPT404	Cell line	CCRF-CEM	Homo sapiens	Activity	=	88.0	%	PMID[20873721]

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 NPC187933 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	21387
0.1-0.2	24174
0.2-0.3	3459
0.3-0.4	544
0.4-0.5	192
0.5-0.6	49
0.6-0.7	22
0.7-0.8	0
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8308	Intermediate Similarity	NPC202728
0.8308	Intermediate Similarity	NPC158059
0.8308	Intermediate Similarity	NPC136697
0.8182	Intermediate Similarity	NPC191412
0.8182	Intermediate Similarity	NPC114159
0.8182	Intermediate Similarity	NPC6818
0.7246	Intermediate Similarity	NPC298554
0.7183	Intermediate Similarity	NPC157113
0.7143	Intermediate Similarity	NPC118519
0.7143	Intermediate Similarity	NPC132824
0.7042	Intermediate Similarity	NPC137072
0.7042	Intermediate Similarity	NPC62516
0.7042	Intermediate Similarity	NPC148964
0.7	Intermediate Similarity	NPC259733
0.7	Intermediate Similarity	NPC158371
0.7	Intermediate Similarity	NPC207922
0.6901	Remote Similarity	NPC247139
0.6667	Remote Similarity	NPC35239
0.662	Remote Similarity	NPC235053
0.6579	Remote Similarity	NPC96693
0.6579	Remote Similarity	NPC54909
0.6579	Remote Similarity	NPC233012
0.6575	Remote Similarity	NPC118964
0.6528	Remote Similarity	NPC256247
0.6486	Remote Similarity	NPC284865
0.6316	Remote Similarity	NPC603658
0.6267	Remote Similarity	NPC147232
0.6267	Remote Similarity	NPC222047
0.6267	Remote Similarity	NPC116457
0.6154	Remote Similarity	NPC327179
0.6027	Remote Similarity	NPC182797
0.6027	Remote Similarity	NPC51700
0.6027	Remote Similarity	NPC121798
0.6027	Remote Similarity	NPC88716
0.6027	Remote Similarity	NPC234346
0.6027	Remote Similarity	NPC68160
0.6027	Remote Similarity	NPC52169
0.6027	Remote Similarity	NPC488562
0.5946	Remote Similarity	NPC61543
0.5946	Remote Similarity	NPC293048
0.5946	Remote Similarity	NPC225585
0.589	Remote Similarity	NPC480946
0.589	Remote Similarity	NPC187722
0.589	Remote Similarity	NPC130577
0.589	Remote Similarity	NPC142415
0.589	Remote Similarity	NPC102683
0.5867	Remote Similarity	NPC293564
0.5811	Remote Similarity	NPC270768
0.5811	Remote Similarity	NPC59263
0.5811	Remote Similarity	NPC210106
0.5811	Remote Similarity	NPC229281
0.5732	Remote Similarity	NPC600756
0.5513	Remote Similarity	NPC127689
0.5513	Remote Similarity	NPC130520
0.5484	Remote Similarity	NPC482049
0.5484	Remote Similarity	NPC482050
0.5443	Remote Similarity	NPC174663
0.5435	Remote Similarity	NPC482052
0.5395	Remote Similarity	NPC606443
0.5376	Remote Similarity	NPC25491
0.5366	Remote Similarity	NPC188833
0.5263	Remote Similarity	NPC274330
0.5263	Remote Similarity	NPC482051
0.5195	Remote Similarity	NPC275809
0.5195	Remote Similarity	NPC171203
0.5195	Remote Similarity	NPC307426
0.5195	Remote Similarity	NPC98442
0.5195	Remote Similarity	NPC242468
0.519	Remote Similarity	NPC9613
0.519	Remote Similarity	NPC263393
0.5132	Remote Similarity	NPC477872
0.5128	Remote Similarity	NPC38754
0.5128	Remote Similarity	NPC88116
0.5128	Remote Similarity	NPC472149
0.5128	Remote Similarity	NPC71074
0.5128	Remote Similarity	NPC37221
0.5128	Remote Similarity	NPC481360
0.5128	Remote Similarity	NPC605937
0.5128	Remote Similarity	NPC609452
0.5065	Remote Similarity	NPC198664
0.5063	Remote Similarity	NPC173089
0.5063	Remote Similarity	NPC228784
0.5063	Remote Similarity	NPC324341
0.5063	Remote Similarity	NPC32407
0.5063	Remote Similarity	NPC263548
0.5063	Remote Similarity	NPC601810
0.5063	Remote Similarity	NPC606320

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC187933 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6313
0.1-0.2	2780
0.2-0.3	52
0.3-0.4	3
0.4-0.5	2
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