NPASS Compound

Natural Product: NPC154712

Natural Product ID	NPC154712
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GFLIQEABBVFGSA-VDKFYWIMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6479440
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 84 0 0 0 0 0 0 0 0999 V2000 3.5256 -1.7992 1.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4128 -1.7609 -0.0604 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6679 -2.0779 -0.7601 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8627 -1.2418 -0.5552 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7925 0.1579 -0.8985 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0520 1.1757 -0.0995 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4608 0.8757 1.2971 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9562 2.5562 -0.5216 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6158 2.8504 -1.6875 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2425 3.5709 0.3680 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6841 -0.5490 -0.5325 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5069 -0.3818 -1.9819 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0217 -0.5681 -2.3122 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3638 -0.8730 -1.0189 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1175 -2.3330 -0.8691 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3129 -0.3968 0.0608 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8562 0.0393 1.2240 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5650 0.1153 1.6338 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4043 -0.4870 0.5573 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8830 -0.3291 0.7537 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6002 -1.6161 0.4003 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2086 -0.0111 2.1944 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6868 0.0399 2.4408 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5050 0.5432 1.3067 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7793 1.2604 0.2330 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6193 1.0975 -1.0463 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8455 2.7709 0.5221 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 0.8226 -0.0667 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1540 0.5392 -1.5151 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9217 -0.2218 -1.8259 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8910 -0.0222 -0.7725 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4263 1.4027 -0.8126 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3645 -0.4608 0.7874 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6326 -0.7991 1.9126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5850 -2.2160 1.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3218 -2.5033 1.7830 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7172 -2.6339 -0.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9833 -3.1305 -0.4528 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4515 -2.2312 -1.8508 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6925 -1.6955 -1.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2724 -1.3360 0.4944 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4961 0.4315 -1.9204 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8160 1.7934 1.8197 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5769 0.5379 1.8492 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3242 0.1662 1.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5395 4.5050 0.0811 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2575 0.3345 -0.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7071 0.6980 -2.2625 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1246 -0.9576 -2.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9637 -1.4837 -2.9672 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5990 0.2445 -2.8953 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3627 -2.7699 0.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9085 -2.6475 -1.1468 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7703 -2.8705 -1.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5802 0.3795 1.9545 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8647 1.1341 1.9485 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6654 -0.5203 2.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2181 -1.6036 0.6405 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2006 -1.5461 -0.5124 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8521 -2.4411 0.2028 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1739 -2.0310 1.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7616 -0.7928 2.8387 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8177 1.0178 2.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8263 0.6535 3.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0854 -0.9632 2.7401 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2524 1.2692 1.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5856 1.6293 -0.7986 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1948 1.6329 -1.8916 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9006 0.0538 -1.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9973 3.2580 0.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6993 2.8900 1.6158 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8286 3.1798 0.2048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7195 1.6917 0.2075 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0139 -0.0241 -1.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1633 1.5338 -2.0476 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4975 0.2048 -2.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1135 -1.2974 -2.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0724 2.0350 -1.4877 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5938 1.5041 -1.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3414 1.9098 0.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8206 -0.8820 1.5677 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 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 2 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 24 33 1 0 16 11 1 0 31 19 1 0 31 14 1 0 28 20 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 10 46 1 0 11 47 1 1 12 48 1 0 12 49 1 0 13 50 1 0 13 51 1 0 15 52 1 0 15 53 1 0 15 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 19 58 1 6 21 59 1 0 21 60 1 0 21 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 23 65 1 0 24 66 1 1 26 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 27 72 1 0 28 73 1 1 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 M END

Standard InCHIKey	GFLIQEABBVFGSA-VDKFYWIMSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-19(9-8-10-20(2)26(32)33)21-13-17-29(6)22(21)11-12-24-28(5)16-15-25(31)27(3,4)23(28)14-18-30(24,29)7/h10-11,19,21,23-25,31H,8-9,12-18H2,1-7H3,(H,32,33)/b20-10+/t19-,21-,23+,24+,25+,28+,29+,30+/m1/s1
SMILES	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1CC[C@@]2(C)C1=CC[C@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@]21C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	511.671 ? Van der Waals volume.
Dense:	0.892	LogP:	4.903 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.025 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.153 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.335	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.728	Fsp³:	0.833
MCE-18:	81.455 ? 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:	0.703	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.529	Promiscuous compounds:	0.167

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.494	MDCK Permeability:	-5.04
Pgp-inhibitor:	0.137	Pgp-substrate:	0.002
PAMPA:	0.994 ? 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):	0.004
20% Bioavailability (F20%):	0.435	30% Bioavailability (F30%):	0.561
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.397
Plasma Protein Binding (PPB):	91.348%	Volume Distribution (VD):	-0.468
Fu:	7.982% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.026
BSEP inhibitor:	0.895

ADMET: Metabolism

CYP1A2-inhibitor:	0.122	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.708
CYP2C9-inhibitor:	0.285	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.742	CYP3A4-substrate:	0.112
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.979
HLM stability:	0.411 ? 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):

5.727

Half-life (T1/2):

0.59

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.023
Human Hepatotoxicity (H-HT):	0.754	Drug-induced Liver Injury (DILI):	0.524
AMES Toxicity:	0.184	Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.309	Skin Sensitization:	0.985
Carcinogencity:	0.483	Eye Corrosion:	0.288
Eye Irritation:	0.941	Respiratory Toxicity:	0.921
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.631
Hematotoxicity:	0.403	Drug-induced Nephrotoxicity:	0.881
Genotoxicity:	0.157	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.255	Hek293 Cytotoxicity:	0.105
BCF:	1.945 ? 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:	4.871 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.159 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.618 ? 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
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	barks	n.a.	n.a.	PMID[15620248]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25515	Garcinia speciosa	Species	Clusiaceae	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

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

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 NPC154712 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	21438
0.1-0.2	23514
0.2-0.3	3712
0.3-0.4	880
0.4-0.5	235
0.5-0.6	46
0.6-0.7	27
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
0.6923	Remote Similarity	NPC477872
0.6866	Remote Similarity	NPC472240
0.6866	Remote Similarity	NPC262858
0.6716	Remote Similarity	NPC112866
0.6471	Remote Similarity	NPC479293
0.6471	Remote Similarity	NPC479294
0.6232	Remote Similarity	NPC51700
0.6232	Remote Similarity	NPC88716
0.6232	Remote Similarity	NPC68160
0.6087	Remote Similarity	NPC480946
0.6087	Remote Similarity	NPC187722
0.6087	Remote Similarity	NPC130577
0.6087	Remote Similarity	NPC142415
0.6087	Remote Similarity	NPC102683
0.6	Remote Similarity	NPC7260
0.6	Remote Similarity	NPC182797
0.6	Remote Similarity	NPC210037
0.6	Remote Similarity	NPC120968
0.6	Remote Similarity	NPC171203
0.6	Remote Similarity	NPC307426
0.6	Remote Similarity	NPC98442
0.6	Remote Similarity	NPC242468
0.6	Remote Similarity	NPC227467
0.6	Remote Similarity	NPC273621
0.6	Remote Similarity	NPC52169
0.6	Remote Similarity	NPC488562
0.6	Remote Similarity	NPC606443
0.5857	Remote Similarity	NPC610937
0.5833	Remote Similarity	NPC202728
0.5833	Remote Similarity	NPC158059
0.5833	Remote Similarity	NPC293564
0.5694	Remote Similarity	NPC18872
0.5694	Remote Similarity	NPC290614
0.5694	Remote Similarity	NPC480720
0.5692	Remote Similarity	NPC27765
0.5692	Remote Similarity	NPC120098
0.5692	Remote Similarity	NPC122418
0.5692	Remote Similarity	NPC491014
0.5634	Remote Similarity	NPC274330
0.5616	Remote Similarity	NPC228784
0.5616	Remote Similarity	NPC324341
0.5616	Remote Similarity	NPC601810
0.5556	Remote Similarity	NPC212948
0.5556	Remote Similarity	NPC195019
0.5455	Remote Similarity	NPC290598
0.5455	Remote Similarity	NPC30590
0.5417	Remote Similarity	NPC198664
0.5362	Remote Similarity	NPC235341
0.5342	Remote Similarity	NPC146554
0.5286	Remote Similarity	NPC95594
0.5278	Remote Similarity	NPC477579
0.527	Remote Similarity	NPC61543
0.527	Remote Similarity	NPC293048
0.527	Remote Similarity	NPC225585
0.5217	Remote Similarity	NPC101475
0.52	Remote Similarity	NPC29765
0.5185	Remote Similarity	NPC603645
0.5143	Remote Similarity	NPC40394
0.5143	Remote Similarity	NPC291379
0.5139	Remote Similarity	NPC40552
0.5139	Remote Similarity	NPC246708
0.5135	Remote Similarity	NPC142361
0.5135	Remote Similarity	NPC270768
0.5135	Remote Similarity	NPC59263
0.5135	Remote Similarity	NPC210106
0.5135	Remote Similarity	NPC229281
0.5135	Remote Similarity	NPC121798
0.5135	Remote Similarity	NPC474684
0.5135	Remote Similarity	NPC234346
0.5132	Remote Similarity	NPC263393
0.5132	Remote Similarity	NPC483384
0.5067	Remote Similarity	NPC138536
0.5065	Remote Similarity	NPC130520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC154712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6184
0.1-0.2	2886
0.2-0.3	74
0.3-0.4	3
0.4-0.5	3
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