NPASS Compound

Natural Product: NPC272075

Natural Product ID	NPC272075
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl 11-Oxo-Ursolate
IUPAC Name	methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,5,6,6a,7,8,8a,10,11,12,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3325724
PubChem CID	10552895
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 83 87 0 0 0 0 0 0 0 0999 V2000 -4.6442 3.8195 -1.5605 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8801 2.6523 -1.3313 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3922 1.3733 -1.5025 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5610 1.2091 -1.8696 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4322 0.2448 -1.2117 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1629 -1.0547 -1.4477 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2234 -1.3456 -0.4424 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5654 -1.3256 0.9158 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8596 -0.0427 1.2208 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9208 0.4518 0.1631 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5222 0.0172 0.3670 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0145 0.1985 1.5869 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3674 -0.2001 1.9033 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6439 -0.4015 3.1065 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3124 -0.3345 0.8096 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7112 0.1471 -0.5067 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6416 -0.5833 -0.6622 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1660 -0.4988 -2.0387 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3781 0.3308 -2.2725 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4296 -2.0457 -0.2884 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3341 1.6234 -0.4332 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5906 -0.1266 -1.6598 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0507 -0.1588 -1.4423 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5094 -0.5228 -0.0587 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7152 0.1289 1.0319 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9070 1.6035 1.1385 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2264 -0.4354 2.3384 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7069 -0.3043 2.5327 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5635 -0.6351 1.3894 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9879 -0.4267 0.0234 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5818 0.7692 -0.6832 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5153 -1.6172 -0.8197 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7253 0.1760 1.4621 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9269 1.0186 1.4835 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7225 -2.5406 1.1053 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1382 3.8134 -2.5528 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9436 4.6840 -1.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3731 4.0177 -0.7529 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6774 -0.9333 -2.4465 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4382 -1.8699 -1.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0542 -0.6463 -0.5405 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5603 -2.3964 -0.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4186 -1.3819 1.6552 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3641 -0.1941 2.1971 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8747 1.5765 0.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5732 0.6490 2.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4096 -1.4565 0.6440 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4029 -0.1141 -2.7469 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3876 -1.5352 -2.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1935 1.3979 -2.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8714 -0.0508 -3.2210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3210 -2.5839 -0.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4697 -2.2304 0.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4391 -2.4891 -0.8145 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9098 2.2072 -1.2114 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7261 1.8199 -0.6977 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4383 2.0434 0.5770 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2780 -1.0657 -2.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4089 0.6885 -2.4240 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5374 0.8049 -1.7085 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5198 -0.9052 -2.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2602 -1.6272 0.0476 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3175 1.9513 2.0258 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8074 2.1925 0.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9689 1.7496 1.5039 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8707 -1.4637 2.4753 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7995 0.2550 3.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9702 0.7167 2.9464 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9438 -0.9769 3.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9728 -1.6711 1.5392 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7562 0.5768 -1.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6017 0.9742 -0.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0209 1.6880 -0.6322 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5731 -1.7576 -0.5158 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8826 -2.4794 -0.5315 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4898 -1.3791 -1.8838 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6256 0.8795 2.1366 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8071 0.8869 0.8473 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2009 1.0522 2.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4616 2.0009 1.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2663 -3.2853 1.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7521 -2.3135 1.5977 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5314 -2.9832 0.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 5 3 1 6 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 1 16 21 1 1 16 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 29 33 1 0 9 34 1 0 8 35 1 0 19 5 1 0 30 24 1 0 10 5 1 0 17 11 1 0 25 15 1 0 1 36 1 0 1 37 1 0 1 38 1 0 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 8 43 1 1 9 44 1 1 10 45 1 1 12 46 1 0 15 47 1 6 18 48 1 0 18 49 1 0 19 50 1 0 19 51 1 0 20 52 1 0 20 53 1 0 20 54 1 0 21 55 1 0 21 56 1 0 21 57 1 0 22 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 24 62 1 1 26 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 29 70 1 1 31 71 1 0 31 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	SCDFHIKTAWIANR-QLTLHDMSSA-N
Standard InCHI	InChI=1S/C31H48O4/c1-18-9-14-31(26(34)35-8)16-15-29(6)20(24(31)19(18)2)17-21(32)25-28(5)12-11-23(33)27(3,4)22(28)10-13-30(25,29)7/h17-19,22-25,33H,9-16H2,1-8H3/t18-,19+,22+,23+,24+,25-,28+,29-,30-,31+/m1/s1
SMILES	COC(=O)[C@@]12CC[C@H]([C@@H]([C@H]2C2=CC(=O)[C@H]3[C@@]([C@@]2(CC1)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	484.36	Volume:	529.201 ? Van der Waals volume.
Dense:	0.915	LogP:	3.918 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.613 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.957 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	63.6 ? 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:	0.44	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.817	Fsp³:	0.871
MCE-18:	103.552 ? 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:	0.665	Fluc inhibitor:	0.032 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.379 ? 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:	0.264	Promiscuous compounds:	0.334

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.527	MDCK Permeability:	-5.072
Pgp-inhibitor:	0.381	Pgp-substrate:	0.214
PAMPA:	0.891 ? 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):	0.001
20% Bioavailability (F20%):	0.788	30% Bioavailability (F30%):	0.586
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.835	MRP1:	0.797
Plasma Protein Binding (PPB):	96.142%	Volume Distribution (VD):	-0.123
Fu:	5.273% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.742
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.643	CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.883	CYP2C19-substrate:	0.345
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.966
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.196
HLM stability:	0.085 ? 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):

9.558

Half-life (T1/2):

0.425

ADMET: Toxicity

hERG Blockers:	0.072	hERG Blockers (10um):	0.156
Human Hepatotoxicity (H-HT):	0.795	Drug-induced Liver Injury (DILI):	0.559
AMES Toxicity:	0.408	Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.645	Skin Sensitization:	0.954
Carcinogencity:	0.923	Eye Corrosion:	0.054
Eye Irritation:	0.886	Respiratory Toxicity:	0.948
Drug-induced Neurotoxicity:	0.057	Ototoxicity:	0.389
Hematotoxicity:	0.625	Drug-induced Nephrotoxicity:	0.823
Genotoxicity:	0.644	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.456	Hek293 Cytotoxicity:	0.379
BCF:	1.838 ? 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:	4.172 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.571 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.026 ? 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
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[12350142]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[15387674]
NPO2543	Anthopleura pacifica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28655	Perovskia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13905	Galaxaura filamentosa	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22067	Pogostemon stellatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2543	Anthopleura pacifica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13905	Galaxaura filamentosa	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28655	Perovskia angustifolia	Species	Lamiaceae	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
Ki	1
EC50	3

Activity Type	# Activity
Individual protein	1
Cell line	2
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1218	Individual protein	Carbonic anhydrase II	Bos taurus	Ki	>	50000.0	nM	PMID[25147151]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell line	HT-29	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[26177446]

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 NPC272075 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	17581
0.1-0.2	26744
0.2-0.3	4875
0.3-0.4	579
0.4-0.5	51
0.5-0.6	21
0.6-0.7	1
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
0.7966	Intermediate Similarity	NPC602872
0.7656	Intermediate Similarity	NPC98874
0.7581	Intermediate Similarity	NPC479748
0.7188	Intermediate Similarity	NPC214756
0.7143	Intermediate Similarity	NPC40552
0.6923	Remote Similarity	NPC295643
0.5857	Remote Similarity	NPC307335
0.5857	Remote Similarity	NPC74855
0.5833	Remote Similarity	NPC610635
0.5676	Remote Similarity	NPC471966
0.5616	Remote Similarity	NPC4036
0.5616	Remote Similarity	NPC65120
0.5616	Remote Similarity	NPC145067
0.5616	Remote Similarity	NPC233455
0.5616	Remote Similarity	NPC158030
0.5479	Remote Similarity	NPC148523
0.5429	Remote Similarity	NPC606009
0.5362	Remote Similarity	NPC95594
0.5352	Remote Similarity	NPC477579
0.5303	Remote Similarity	NPC27765
0.5303	Remote Similarity	NPC122418
0.5303	Remote Similarity	NPC491014
0.5211	Remote Similarity	NPC246708
0.52	Remote Similarity	NPC310546
0.507	Remote Similarity	NPC234617
0.5068	Remote Similarity	NPC304285
0.5063	Remote Similarity	NPC171208

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC272075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6836
0.1-0.2	2205
0.2-0.3	100
0.3-0.4	8
0.4-0.5	0
0.5-0.6	1
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
0.5616	Remote Similarity	NPD7515	Phase 2

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