NPASS Compound

Natural Product: NPC478657

Natural Product ID	NPC478657
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OFGUCAFZXULUSI-LODAOABASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44575942
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 5.1130 -2.3137 0.6573 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9773 -1.3807 -0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6214 -2.0984 -1.7045 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7397 -0.0991 -0.3302 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2022 0.6261 0.8741 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7194 0.9460 0.7259 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6963 2.4666 0.4413 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9730 0.7615 1.9959 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7081 -0.0036 1.9624 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8869 -0.0041 0.7443 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4906 -1.4543 0.4284 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6590 0.5371 -0.4128 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0832 1.2332 -1.3851 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3531 1.5629 -1.4600 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0643 0.6783 -0.5216 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5715 0.8508 -0.5186 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0147 2.1553 0.0421 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9958 0.8757 -1.9981 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4621 0.6689 -2.1570 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8886 -0.5727 -1.4638 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5346 -0.6465 0.0007 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4591 0.0714 0.9074 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7179 -2.1396 0.3563 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0414 -2.5020 0.1115 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0825 -0.3584 0.1728 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6220 -0.3910 1.5775 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3195 0.1862 1.9228 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4572 0.7459 0.8485 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0767 2.1641 1.2190 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2513 -0.7815 -1.6782 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7344 0.5109 -3.5150 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1265 0.3228 -0.4969 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5276 -1.0837 -0.7956 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5852 -3.2673 0.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5716 -1.9370 1.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1468 -2.5717 0.8807 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5350 -3.2010 -1.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1123 -1.8234 -2.6669 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7111 -1.8659 -1.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6966 0.4797 -1.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7915 -0.3682 -0.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3157 -0.0484 1.7525 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8236 1.5006 1.0576 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7589 2.9120 0.7822 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5963 2.9604 0.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8004 2.6417 -0.6493 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8811 1.7359 2.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6821 0.2135 2.6962 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1203 0.3001 2.8821 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9711 -1.0803 2.2233 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5390 -1.6688 0.7281 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5879 -1.7025 -0.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0719 -2.1629 1.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7024 1.6078 -2.2164 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7309 1.3279 -2.5029 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5595 2.6476 -1.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9200 -0.3761 -0.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9838 2.4810 -0.4375 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3032 2.9445 -0.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1948 2.1871 1.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7562 1.9072 -2.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4625 0.1186 -2.5769 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1020 1.4992 -1.8158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3448 -1.4336 -1.9530 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3500 1.1416 0.9973 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4694 -0.4479 1.9111 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5042 -0.1086 0.5159 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4201 -2.3183 1.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0681 -2.7621 -0.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4470 -2.9902 0.8825 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5850 -1.2389 -0.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6278 -1.4802 1.8931 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4814 0.0217 2.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5178 0.9693 2.7184 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6803 -0.5531 2.4985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5667 2.0782 2.1443 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9320 2.7652 1.5926 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3959 2.7376 0.4317 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4663 -0.4283 -2.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7429 1.4323 -3.9091 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5604 0.9107 -1.3645 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3738 -1.2731 -1.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9531 -1.8670 -0.3111 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 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 20 30 1 0 19 31 1 0 12 32 1 0 32 33 1 0 33 2 1 0 32 6 1 0 28 10 1 0 28 15 1 0 25 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 7 45 1 0 7 46 1 0 8 47 1 0 8 48 1 0 9 49 1 0 9 50 1 0 11 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 6 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 1 20 64 1 6 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 24 70 1 0 25 71 1 6 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 31 80 1 0 32 81 1 6 33 82 1 0 33 83 1 0 M END

Standard InCHIKey	OFGUCAFZXULUSI-LODAOABASA-N
Standard InCHI	InChI=1S/C30H50O3/c1-25(2)12-13-26(3)14-15-29(6)19(20(26)16-25)8-9-23-27(4)17-21(32)24(33)28(5,18-31)22(27)10-11-30(23,29)7/h8,20-24,31-33H,9-18H2,1-7H3/t20-,21+,22+,23+,24-,26+,27-,28-,29+,30+/m0/s1
SMILES	CC1(C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O)O)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.38	Volume:	508.388 ? Van der Waals volume.
Dense:	0.902	LogP:	4.19 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.969 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.821 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.415	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.901	Fsp³:	0.933
MCE-18:	104.897 ? 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:	0.912	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.435	Promiscuous compounds:	0.083

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212	MDCK Permeability:	-4.949
Pgp-inhibitor:	0.736	Pgp-substrate:	0.016
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):	0.001
20% Bioavailability (F20%):	0.765	30% Bioavailability (F30%):	0.095
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983	MRP1:	0.682
Plasma Protein Binding (PPB):	94.512%	Volume Distribution (VD):	0.05
Fu:	5.421% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.413	BCRP inhibitor:	0.764
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.026	CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.496	CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.593	CYP3A4-substrate:	0.898
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.679
HLM stability:	0.706 ? 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):

7.867

Half-life (T1/2):

0.645

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.157
Human Hepatotoxicity (H-HT):	0.602	Drug-induced Liver Injury (DILI):	0.254
AMES Toxicity:	0.349	Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.15	Skin Sensitization:	0.877
Carcinogencity:	0.784	Eye Corrosion:	0.046
Eye Irritation:	0.659	Respiratory Toxicity:	0.403
Drug-induced Neurotoxicity:	0.048	Ototoxicity:	0.722
Hematotoxicity:	0.525	Drug-induced Nephrotoxicity:	0.815
Genotoxicity:	0.18	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.159	Hek293 Cytotoxicity:	0.229
BCF:	2.448 ? 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:	4.319 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.372 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.02 ? 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
NPO27814	Commiphora merkeri	Species	Burseraceae	Eukaryota	Roots	n.a.	n.a.	PMID[2607349]
NPO27814	Commiphora merkeri	Species	Burseraceae	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	2

Activity Type	# Activity
Organism	2

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
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	28.0	%	PMID[2607349]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	37.0	%	PMID[2607349]

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 NPC478657 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	27914
0.1-0.2	18983
0.2-0.3	2183
0.3-0.4	577
0.4-0.5	137
0.5-0.6	50
0.6-0.7	9
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
0.7368	Intermediate Similarity	NPC196753
0.6552	Remote Similarity	NPC290598
0.6552	Remote Similarity	NPC30590
0.6406	Remote Similarity	NPC136313
0.6212	Remote Similarity	NPC231063
0.6212	Remote Similarity	NPC282395
0.6119	Remote Similarity	NPC145667
0.6032	Remote Similarity	NPC230295
0.6032	Remote Similarity	NPC98386
0.6	Remote Similarity	NPC601696
0.5968	Remote Similarity	NPC101475
0.5797	Remote Similarity	NPC201657
0.5781	Remote Similarity	NPC53744
0.5735	Remote Similarity	NPC173744
0.5735	Remote Similarity	NPC88116
0.5735	Remote Similarity	NPC204961
0.5735	Remote Similarity	NPC73004
0.5735	Remote Similarity	NPC609452
0.5672	Remote Similarity	NPC172361
0.5652	Remote Similarity	NPC32407
0.5652	Remote Similarity	NPC263548
0.5652	Remote Similarity	NPC606320
0.5645	Remote Similarity	NPC142754
0.5634	Remote Similarity	NPC20235
0.5634	Remote Similarity	NPC299996
0.5625	Remote Similarity	NPC253807
0.5625	Remote Similarity	NPC158662
0.5571	Remote Similarity	NPC247139
0.5556	Remote Similarity	NPC488518
0.5469	Remote Similarity	NPC34177
0.5397	Remote Similarity	NPC474488
0.5385	Remote Similarity	NPC235341
0.5385	Remote Similarity	NPC195334
0.5373	Remote Similarity	NPC231431
0.5362	Remote Similarity	NPC84319
0.5362	Remote Similarity	NPC52021
0.5362	Remote Similarity	NPC599947
0.5352	Remote Similarity	NPC9613
0.5342	Remote Similarity	NPC479743
0.5303	Remote Similarity	NPC3915
0.5286	Remote Similarity	NPC110308
0.525	Remote Similarity	NPC68419
0.5231	Remote Similarity	NPC311078
0.5217	Remote Similarity	NPC213412
0.5217	Remote Similarity	NPC191965
0.5152	Remote Similarity	NPC471899
0.5152	Remote Similarity	NPC475862
0.5147	Remote Similarity	NPC246708
0.5143	Remote Similarity	NPC306541
0.5143	Remote Similarity	NPC481361
0.5139	Remote Similarity	NPC263393
0.5125	Remote Similarity	NPC258130
0.5077	Remote Similarity	NPC474989
0.5077	Remote Similarity	NPC470620
0.5075	Remote Similarity	NPC253402
0.5075	Remote Similarity	NPC470588
0.5072	Remote Similarity	NPC137306
0.5072	Remote Similarity	NPC479525
0.507	Remote Similarity	NPC472149
0.507	Remote Similarity	NPC37221

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8139
0.1-0.2	981
0.2-0.3	28
0.3-0.4	1
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
0.5143	Remote Similarity	NPD7645	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