NPASS Compound

Natural Product: NPC173089

Natural Product ID	NPC173089
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Oxo-23-Hydroxyurs-12-En-28-Oic Acid
IUPAC Name	(1S,2R,4aS,6aR,6aS,6bR,8aR,9R,12aR,14bS)-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-oxo-1,2,3,4,5,6,6a,7,8,8a,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1773215
PubChem CID	14396856
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 80 84 0 0 0 0 0 0 0 0999 V2000 -5.5597 -1.2270 2.2851 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7961 -0.0215 1.7991 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5487 0.5807 0.6481 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0551 0.0364 -0.6941 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6763 0.6011 -0.9310 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0150 -0.1405 -2.0524 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5584 0.1078 -2.2141 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7925 -0.1423 -0.8964 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9631 -1.6332 -0.6959 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5050 0.6883 0.0834 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8467 1.5930 0.7685 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5985 1.8760 0.6514 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2115 0.5528 0.2498 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6583 0.4939 0.5358 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3471 1.7749 0.1578 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7817 0.4159 2.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9507 -0.3882 2.5345 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0376 -0.3002 1.5530 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1118 0.2081 1.7302 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7334 -0.9151 0.2219 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6292 -0.3578 -0.8274 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0048 -2.3942 0.3837 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7779 -3.1297 -0.7522 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2703 -0.7258 -0.0378 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9470 -0.7410 -1.5148 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4425 -0.9885 -1.6383 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6707 0.2080 -1.0763 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8457 1.2474 -2.1500 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9466 0.5990 0.3689 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3740 -0.4200 1.3582 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5101 -0.2769 2.5935 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8524 2.0076 -1.3754 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9958 2.5094 -1.4937 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7771 2.8372 -1.6814 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5671 -1.3117 1.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0107 -2.1446 1.9649 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6223 -1.2806 3.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7664 0.7101 2.6183 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5380 1.6868 0.6569 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6145 0.2828 0.7223 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7765 0.4492 -1.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1016 -1.0497 -0.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4902 0.2726 -2.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3472 -1.1782 -2.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1811 -0.6201 -2.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4352 1.1488 -2.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3746 -2.0704 0.0989 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5989 -2.1113 -1.6567 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0250 -1.9503 -0.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3527 2.2396 1.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0460 2.2983 1.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6916 2.6630 -0.1233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7468 -0.2015 0.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2060 1.9832 0.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6630 2.6311 0.3138 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7747 1.8085 -0.8372 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8779 -0.0910 2.4986 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8104 1.4248 2.5052 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3210 0.0791 3.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6864 -1.4286 2.8126 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6029 -0.9294 -0.7660 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2436 -0.5312 -1.8369 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9231 0.7030 -0.6440 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0596 -2.5457 0.7031 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3867 -2.7717 1.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2867 -3.9865 -0.6631 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7455 -1.6033 0.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3113 0.1065 -2.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4234 -1.6523 -1.9386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3084 -1.1084 -2.7316 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2874 -1.9117 -1.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5397 0.7563 -3.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2507 2.1473 -2.0379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8843 1.5302 -2.2723 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2981 1.5683 0.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4738 -1.4452 1.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4463 -0.3215 2.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7369 0.6187 3.1849 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6644 -1.2249 3.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9021 3.8260 -1.4244 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 7 8 1 0 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 10 29 1 0 29 30 1 0 30 31 1 0 5 32 1 6 32 33 2 0 32 34 1 0 30 2 1 0 29 5 1 0 27 8 1 0 27 13 1 0 24 14 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 6 43 1 0 6 44 1 0 7 45 1 0 7 46 1 0 9 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 1 15 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 24 67 1 1 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 1 30 76 1 6 31 77 1 0 31 78 1 0 31 79 1 0 34 80 1 0 M END

Standard InCHIKey	RWFVBIQKMCLKMM-CARKBDGISA-N
Standard InCHI	InChI=1S/C30H46O4/c1-18-9-14-30(25(33)34)16-15-28(5)20(24(30)19(18)2)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h7,18-19,21-22,24,31H,8-17H2,1-6H3,(H,33,34)/t18-,19+,21-,22-,24+,26+,27+,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.57 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.156 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.358 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.466	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.894	Fsp³:	0.867
MCE-18:	101.786 ? 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:	0.771	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.034 ? 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:	0.325	Promiscuous compounds:	0.085

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.569	MDCK Permeability:	-5.087
Pgp-inhibitor:	0.03	Pgp-substrate:	0.003
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%):	0.153	30% Bioavailability (F30%):	0.01
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.858	MRP1:	0.916
Plasma Protein Binding (PPB):	91.813%	Volume Distribution (VD):	-0.44
Fu:	8.183% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.348	BCRP inhibitor:	0.803
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.176	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.987	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? 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):

3.501

Half-life (T1/2):

0.806

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.024
Human Hepatotoxicity (H-HT):	0.721	Drug-induced Liver Injury (DILI):	0.533
AMES Toxicity:	0.231	Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.205	Skin Sensitization:	0.915
Carcinogencity:	0.92	Eye Corrosion:	0.008
Eye Irritation:	0.474	Respiratory Toxicity:	0.658
Drug-induced Neurotoxicity:	0.031	Ototoxicity:	0.7
Hematotoxicity:	0.763	Drug-induced Nephrotoxicity:	0.872
Genotoxicity:	0.81	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.077	Hek293 Cytotoxicity:	0.144
BCF:	0.752 ? 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:	3.496 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.035 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.335 ? 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
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	twig	n.a.	PMID[21309591]
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21309591]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418278]
NPO26573	Artemisia umbelliformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28	Cutleria multifida	Species	Cutleriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4636	Onopordum anatolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3731	Salix japonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5560	Castor fiber	Species	Castoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26573	Artemisia umbelliformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28	Cutleria multifida	Species	Cutleriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26307	Viburnum ayavacense	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6515	Juglans sinensis	Species	Juglandaceae	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
Inhibition	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	77.9	%	PMID[21309591]

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 NPC173089 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	19438
0.1-0.2	25717
0.2-0.3	3759
0.3-0.4	638
0.4-0.5	203
0.5-0.6	67
0.6-0.7	21
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8361	Intermediate Similarity	NPC274050
0.8361	Intermediate Similarity	NPC162632
0.7424	Intermediate Similarity	NPC158141
0.7353	Intermediate Similarity	NPC148964
0.7313	Intermediate Similarity	NPC477288
0.7273	Intermediate Similarity	NPC51700
0.7273	Intermediate Similarity	NPC88716
0.7273	Intermediate Similarity	NPC68160
0.7164	Intermediate Similarity	NPC61543
0.7164	Intermediate Similarity	NPC293048
0.7164	Intermediate Similarity	NPC225585
0.6812	Remote Similarity	NPC32407
0.6812	Remote Similarity	NPC263548
0.6812	Remote Similarity	NPC606320
0.6714	Remote Similarity	NPC485589
0.6667	Remote Similarity	NPC71074
0.6667	Remote Similarity	NPC605937
0.6571	Remote Similarity	NPC87095
0.6486	Remote Similarity	NPC230151
0.6429	Remote Similarity	NPC38754
0.6377	Remote Similarity	NPC274330
0.6377	Remote Similarity	NPC477289
0.6351	Remote Similarity	NPC485586
0.6351	Remote Similarity	NPC485588
0.6216	Remote Similarity	NPC6255
0.6125	Remote Similarity	NPC57362
0.6111	Remote Similarity	NPC305464
0.6111	Remote Similarity	NPC19376
0.6111	Remote Similarity	NPC25848
0.6076	Remote Similarity	NPC476890
0.6076	Remote Similarity	NPC476889
0.6049	Remote Similarity	NPC177246
0.5949	Remote Similarity	NPC485585
0.5946	Remote Similarity	NPC477290
0.5797	Remote Similarity	NPC161496
0.5753	Remote Similarity	NPC37221
0.5732	Remote Similarity	NPC485882
0.56	Remote Similarity	NPC610635
0.5529	Remote Similarity	NPC485587
0.5526	Remote Similarity	NPC127689
0.5467	Remote Similarity	NPC293564
0.5467	Remote Similarity	NPC479077
0.5465	Remote Similarity	NPC173569
0.5455	Remote Similarity	NPC117663
0.5444	Remote Similarity	NPC479744
0.5405	Remote Similarity	NPC182797
0.5405	Remote Similarity	NPC263272
0.5405	Remote Similarity	NPC52169
0.5405	Remote Similarity	NPC195019
0.5405	Remote Similarity	NPC488562
0.5395	Remote Similarity	NPC193750
0.5342	Remote Similarity	NPC267691
0.5342	Remote Similarity	NPC201655
0.5342	Remote Similarity	NPC242631
0.5326	Remote Similarity	NPC178093
0.527	Remote Similarity	NPC480946
0.527	Remote Similarity	NPC187722
0.527	Remote Similarity	NPC130577
0.527	Remote Similarity	NPC142415
0.527	Remote Similarity	NPC102683
0.5263	Remote Similarity	NPC202728
0.5263	Remote Similarity	NPC158059
0.5263	Remote Similarity	NPC40092
0.5263	Remote Similarity	NPC136697
0.5256	Remote Similarity	NPC20235
0.5256	Remote Similarity	NPC299996
0.525	Remote Similarity	NPC600880
0.5217	Remote Similarity	NPC304110
0.5217	Remote Similarity	NPC82477
0.5217	Remote Similarity	NPC27518
0.5217	Remote Similarity	NPC611516
0.5213	Remote Similarity	NPC479745
0.52	Remote Similarity	NPC270768
0.52	Remote Similarity	NPC59263
0.52	Remote Similarity	NPC210106
0.52	Remote Similarity	NPC229281
0.52	Remote Similarity	NPC121798
0.52	Remote Similarity	NPC474511
0.52	Remote Similarity	NPC234346
0.52	Remote Similarity	NPC479079
0.5195	Remote Similarity	NPC191412
0.5195	Remote Similarity	NPC114159
0.5195	Remote Similarity	NPC6818
0.5161	Remote Similarity	NPC479747
0.5161	Remote Similarity	NPC479746
0.5139	Remote Similarity	NPC3915
0.5132	Remote Similarity	NPC1753
0.5132	Remote Similarity	NPC88116
0.5128	Remote Similarity	NPC25299
0.5128	Remote Similarity	NPC481322
0.5128	Remote Similarity	NPC62516
0.5122	Remote Similarity	NPC93744
0.5122	Remote Similarity	NPC476888
0.5111	Remote Similarity	NPC475457
0.5065	Remote Similarity	NPC291028
0.5065	Remote Similarity	NPC298554
0.5063	Remote Similarity	NPC187933
0.5063	Remote Similarity	NPC324063
0.5063	Remote Similarity	NPC157113

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC173089 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5509
0.1-0.2	3564
0.2-0.3	68
0.3-0.4	7
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