NPASS Compound

Natural Product: NPC200752

Natural Product ID	NPC200752
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3 Beta-O-Acetyloleanolic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aS,10S,12aS,14bS)-10-methoxycarbonyl-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	3 Beta-O-Acetyloleanolic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503071
PubChem CID	44583799
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 86 90 0 0 0 0 0 0 0 0999 V2000 -5.8911 0.0771 2.8137 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1788 0.8379 1.7002 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9643 2.2485 2.1694 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0235 0.7319 0.4660 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5502 -0.3557 -0.4786 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2108 0.0389 -1.0985 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6080 -1.0910 -1.8165 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1393 -0.9934 -2.1004 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3284 -0.6517 -0.8396 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5543 -1.9064 0.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9862 0.5226 -0.2719 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2824 1.5955 0.0177 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1721 1.7916 -0.1622 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8094 0.4177 -0.2094 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3129 0.4952 -0.2518 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8389 1.1540 -1.5133 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9247 1.2517 0.8984 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2500 0.4004 2.0956 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4411 -0.4598 1.7257 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6391 0.4130 1.8153 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5858 1.6212 2.1655 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9227 -0.0506 1.5140 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0704 0.7992 1.6047 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2227 -1.0619 0.3692 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3945 -2.5845 0.5811 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2499 -0.7201 -0.6602 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8042 -0.9026 -0.0569 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3546 -1.7279 -1.2004 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -1.8724 -1.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1439 -0.4993 -1.1471 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2237 -0.1794 -2.6089 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4249 0.6112 0.0304 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8376 0.1457 1.3862 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4927 1.1097 -2.1269 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6555 1.5273 -2.3564 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4696 1.6834 -2.8689 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7344 -0.5303 2.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3052 0.7349 3.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1976 -0.6709 3.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8782 2.8408 1.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0614 2.7231 1.7766 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8851 2.2332 3.2950 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1018 0.5024 0.6922 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0266 1.7276 -0.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3279 -0.4767 -1.2597 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4713 -1.3026 0.0615 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9451 -2.0518 -1.3814 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0916 -1.1352 -2.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8762 -1.9786 -2.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0317 -0.2476 -2.8953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0017 -1.9050 0.9471 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2086 -2.7820 -0.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6339 -2.1374 0.1231 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8032 2.5001 0.4547 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5314 2.3224 0.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4347 2.4191 -1.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5796 0.0250 0.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6406 1.9280 -1.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0744 1.7687 -2.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3903 0.4519 -2.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9519 1.5891 0.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4710 2.2106 1.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6007 1.1053 2.8887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4112 -0.1558 2.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5576 -1.2192 2.5312 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8285 0.4073 2.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5287 0.7569 0.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7783 1.8512 1.8046 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6618 -3.0845 -0.3601 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2698 -2.6835 1.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5329 -3.0022 1.1075 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9419 -1.2871 -1.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4178 0.3340 -0.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2169 -1.2316 -0.3717 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2058 -1.2950 0.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7313 -2.7794 -1.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6848 -1.4582 -2.1915 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6707 -2.3506 -0.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6083 -2.5185 -1.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2770 -0.2493 -3.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2200 -1.0559 -3.1266 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2890 0.7123 -2.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7409 1.7120 0.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1100 0.5273 2.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0900 -0.9042 1.5031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5623 2.6931 -3.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 19 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 11 32 1 0 32 33 1 0 6 34 1 6 34 35 2 0 34 36 1 0 33 2 1 0 32 6 1 0 30 9 1 0 30 14 1 0 27 15 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 0 5 46 1 0 7 47 1 0 7 48 1 0 8 49 1 0 8 50 1 0 10 51 1 0 10 52 1 0 10 53 1 0 12 54 1 0 13 55 1 0 13 56 1 0 14 57 1 1 16 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 0 18 64 1 0 19 65 1 1 23 66 1 0 23 67 1 0 23 68 1 0 25 69 1 0 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 27 75 1 1 28 76 1 0 28 77 1 0 29 78 1 0 29 79 1 0 31 80 1 0 31 81 1 0 31 82 1 0 32 83 1 1 33 84 1 0 33 85 1 0 36 86 1 0 M END

Standard InCHIKey	HDWYAPCZHCDUNP-JVZQWSIASA-N
Standard InCHI	InChI=1S/C32H50O4/c1-27(2)15-17-32(26(34)35)18-16-30(6)20(22(32)19-27)9-10-24-29(5)13-11-21(25(33)36-8)28(3,4)23(29)12-14-31(24,30)7/h9,21-24H,10-19H2,1-8H3,(H,34,35)/t21-,22+,23+,24-,29+,30-,31-,32+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](C(=O)OC)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.37	Volume:	546.497 ? Van der Waals volume.
Dense:	0.912	LogP:	4.488 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.691 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.756 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	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:	0.313	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.715	Fsp³:	0.875
MCE-18:	106.667 ? 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:	0.728	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.488	Promiscuous compounds:	0.096

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.201	MDCK Permeability:	-4.955
Pgp-inhibitor:	0.014	Pgp-substrate:	0.0
PAMPA:	0.916 ? 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%):	0.117	30% Bioavailability (F30%):	0.038
50% Bioavailability (F50%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242	MRP1:	0.468
Plasma Protein Binding (PPB):	92.965%	Volume Distribution (VD):	-0.224
Fu:	7.103% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.031
BSEP inhibitor:	0.963

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.964	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.744
HLM stability:	0.211 ? 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):

5.229

Half-life (T1/2):

0.763

ADMET: Toxicity

hERG Blockers:	0.153	hERG Blockers (10um):	0.222
Human Hepatotoxicity (H-HT):	0.698	Drug-induced Liver Injury (DILI):	0.456
AMES Toxicity:	0.045	Rat Oral Acute Toxicity:	0.37
Maximum Recommended Daily Dose:	0.854	Skin Sensitization:	0.902
Carcinogencity:	0.859	Eye Corrosion:	0.037
Eye Irritation:	0.594	Respiratory Toxicity:	0.931
Drug-induced Neurotoxicity:	0.084	Ototoxicity:	0.389
Hematotoxicity:	0.44	Drug-induced Nephrotoxicity:	0.701
Genotoxicity:	0.389	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.012	Hek293 Cytotoxicity:	0.228
BCF:	2.088 ? 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:	4.789 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.244 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.708 ? 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
NPO9267	Croton ciliatoglandulifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792405]
NPO9267	Croton ciliatoglandulifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9267	Croton ciliatoglandulifer	Species	Euphorbiaceae	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
IC50	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual protein	Cyclooxygenase-1	Ovis aries	IC50	=	1.0	nM	PMID[16792405]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	=	2200.0	nM	PMID[16792405]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC200752 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	22502
0.1-0.2	24149
0.2-0.3	2557
0.3-0.4	362
0.4-0.5	196
0.5-0.6	68
0.6-0.7	19
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
0.6812	Remote Similarity	NPC120840
0.6769	Remote Similarity	NPC604575
0.6667	Remote Similarity	NPC158141
0.6618	Remote Similarity	NPC480946
0.6618	Remote Similarity	NPC130577
0.6618	Remote Similarity	NPC142415
0.6618	Remote Similarity	NPC102683
0.6522	Remote Similarity	NPC156981
0.6338	Remote Similarity	NPC298554
0.6301	Remote Similarity	NPC296164
0.6286	Remote Similarity	NPC270768
0.6286	Remote Similarity	NPC59263
0.6286	Remote Similarity	NPC210106
0.6197	Remote Similarity	NPC110308
0.6087	Remote Similarity	NPC280654
0.6056	Remote Similarity	NPC84319
0.6056	Remote Similarity	NPC52021
0.6056	Remote Similarity	NPC599947
0.6	Remote Similarity	NPC96580
0.5974	Remote Similarity	NPC481362
0.5972	Remote Similarity	NPC231063
0.5972	Remote Similarity	NPC282395
0.5833	Remote Similarity	NPC282616
0.5833	Remote Similarity	NPC275809
0.5833	Remote Similarity	NPC37038
0.5753	Remote Similarity	NPC106112
0.5753	Remote Similarity	NPC261935
0.5753	Remote Similarity	NPC481360
0.5732	Remote Similarity	NPC283849
0.5732	Remote Similarity	NPC28198
0.5732	Remote Similarity	NPC476123
0.5714	Remote Similarity	NPC100383
0.5714	Remote Similarity	NPC474727
0.5658	Remote Similarity	NPC324063
0.5647	Remote Similarity	NPC43353
0.5616	Remote Similarity	NPC182797
0.5616	Remote Similarity	NPC52169
0.5616	Remote Similarity	NPC488562
0.56	Remote Similarity	NPC474963
0.557	Remote Similarity	NPC188833
0.5568	Remote Similarity	NPC22676
0.5506	Remote Similarity	NPC198621
0.5506	Remote Similarity	NPC216940
0.5484	Remote Similarity	NPC469945
0.5479	Remote Similarity	NPC198664
0.5455	Remote Similarity	NPC171007
0.5455	Remote Similarity	NPC190849
0.5435	Remote Similarity	NPC610795
0.5422	Remote Similarity	NPC204407
0.5405	Remote Similarity	NPC121798
0.5405	Remote Similarity	NPC234346
0.5402	Remote Similarity	NPC284807
0.5402	Remote Similarity	NPC473538
0.5357	Remote Similarity	NPC606107
0.5281	Remote Similarity	NPC475611
0.5275	Remote Similarity	NPC605663
0.5263	Remote Similarity	NPC291028
0.5263	Remote Similarity	NPC228784
0.5263	Remote Similarity	NPC324341
0.5263	Remote Similarity	NPC601810
0.5256	Remote Similarity	NPC488521
0.525	Remote Similarity	NPC600880
0.5233	Remote Similarity	NPC286347
0.5227	Remote Similarity	NPC294112
0.5217	Remote Similarity	NPC132126
0.5208	Remote Similarity	NPC180550
0.5208	Remote Similarity	NPC35405
0.52	Remote Similarity	NPC307282
0.52	Remote Similarity	NPC64872
0.52	Remote Similarity	NPC25906
0.5135	Remote Similarity	NPC267691
0.5132	Remote Similarity	NPC130278
0.5132	Remote Similarity	NPC472149
0.5132	Remote Similarity	NPC609452
0.5128	Remote Similarity	NPC608622
0.5125	Remote Similarity	NPC485588
0.5122	Remote Similarity	NPC93744
0.5122	Remote Similarity	NPC476888
0.5119	Remote Similarity	NPC476890
0.5111	Remote Similarity	NPC475472
0.5063	Remote Similarity	NPC222047
0.5054	Remote Similarity	NPC174679
0.5054	Remote Similarity	NPC279554
0.5054	Remote Similarity	NPC56713
0.5054	Remote Similarity	NPC59804
0.5052	Remote Similarity	NPC601567
0.5052	Remote Similarity	NPC606631

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC200752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6196
0.1-0.2	2923
0.2-0.3	23
0.3-0.4	7
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