NPASS Compound

Natural Product: NPC95810

Natural Product ID	NPC95810
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SHBOGBUJSDTFTG-PWRWEZGUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1796006
PubChem CID	56677247
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 85 0 0 0 0 0 0 0 0999 V2000 1.1195 -4.9336 1.5561 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8279 -3.5019 1.7758 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0246 -3.0074 2.8931 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3429 -2.7124 0.7624 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0424 -1.3308 0.9080 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3750 -1.0196 0.5073 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4466 -0.0648 -0.7005 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8214 0.1226 -0.9968 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3366 -0.2177 -2.2567 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5183 -0.6867 -3.0786 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7454 -0.0231 -2.5557 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1643 -0.3944 -3.8367 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4846 -0.2338 -4.1782 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4088 0.2821 -3.2972 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9701 0.6370 -2.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6390 0.4957 -1.6484 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8501 1.1299 -0.0962 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6698 0.8945 -0.0764 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9856 -0.5557 0.0528 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3532 -0.7161 0.3677 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2466 -1.3171 -0.5334 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7341 -1.6885 -1.6240 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6572 -1.5231 -0.2882 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4202 -2.1089 -1.2669 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7789 -2.3444 -1.1059 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4004 -1.9906 0.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6541 -1.3992 1.0562 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2846 -1.1666 0.8828 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3235 1.3371 -1.3534 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0983 1.8006 1.0135 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9607 3.2211 0.4608 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3299 3.5517 -0.1432 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1813 2.4486 -0.6784 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3069 2.4549 -2.1839 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4963 2.7408 -0.2121 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3997 1.6568 1.4843 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6270 1.5704 2.8742 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6360 1.6239 3.6520 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9835 1.4206 3.4543 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3241 1.1486 1.2282 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8979 -0.0321 1.5480 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4744 -0.4634 2.9591 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3896 -0.0795 1.5198 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1597 -5.2149 1.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3970 -5.5347 2.1646 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9476 -5.2412 0.4973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2824 -1.0833 1.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0152 -1.8886 0.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9813 -0.4782 -1.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4956 -0.8034 -4.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8026 -0.5289 -5.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4369 0.3845 -3.6258 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6607 1.0426 -1.3358 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3119 0.7800 -0.6649 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8312 -0.9937 -0.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9982 -2.4193 -2.2205 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3464 -2.8150 -1.9161 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4587 -2.1888 0.1457 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1657 -1.1265 1.9684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7522 -0.7049 1.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4348 1.3043 -1.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1067 2.3237 -1.7149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1799 0.5233 -2.1200 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3652 1.7983 1.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8675 3.3829 -0.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1792 3.8680 1.3686 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1367 4.2469 -1.0188 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8814 4.2404 0.5705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8344 3.3715 -2.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9351 1.5175 -2.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3771 2.5204 -2.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1730 2.4535 -0.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1621 2.2751 4.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7759 1.4718 2.7089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0263 0.5103 4.0898 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3743 -1.5639 3.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3156 -0.2179 3.6763 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6208 0.1090 3.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8754 0.8586 1.2356 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7888 -0.8800 0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8302 -0.3249 2.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 18 29 1 6 18 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 1 30 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 17 40 1 1 40 41 1 0 41 42 1 0 41 43 1 0 19 5 1 0 28 23 1 0 41 6 1 0 16 11 1 0 33 17 1 0 1 44 1 0 1 45 1 0 1 46 1 0 5 47 1 1 6 48 1 6 7 49 1 6 12 50 1 0 13 51 1 0 14 52 1 0 15 53 1 0 16 54 1 0 19 55 1 6 24 56 1 0 25 57 1 0 26 58 1 0 27 59 1 0 28 60 1 0 29 61 1 0 29 62 1 0 29 63 1 0 30 64 1 1 31 65 1 0 31 66 1 0 32 67 1 0 32 68 1 0 34 69 1 0 34 70 1 0 34 71 1 0 35 72 1 0 39 73 1 0 39 74 1 0 39 75 1 0 42 76 1 0 42 77 1 0 42 78 1 0 43 79 1 0 43 80 1 0 43 81 1 0 M END

Standard InCHIKey	SHBOGBUJSDTFTG-PWRWEZGUSA-N
Standard InCHI	InChI=1S/C33H38O10/c1-19(34)39-23-17-18-31(5,38)33-26(41-28(36)21-13-9-7-10-14-21)24(30(3,4)43-33)25(40-20(2)35)27(32(23,33)6)42-29(37)22-15-11-8-12-16-22/h7-16,23-27,38H,17-18H2,1-6H3/t23-,24+,25+,26+,27-,31-,32-,33-/m0/s1
SMILES	CC(=O)O[C@@H]1[C@@H]2[C@@H](OC(=O)c3ccccc3)[C@]3([C@@]([C@H]1OC(=O)c1ccccc1)(C)[C@H](CC[C@]3(C)O)OC(=O)C)OC2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.25	Volume:	598.079 ? Van der Waals volume.
Dense:	0.994	LogP:	2.702 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.786 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.175 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	134.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.386	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.606	Fsp³:	0.515
MCE-18:	168.72 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.298	Fluc inhibitor:	0.021 ? 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:	0.03 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.124	Promiscuous compounds:	0.123

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.423	MDCK Permeability:	-4.806
Pgp-inhibitor:	1.0	Pgp-substrate:	0.614
PAMPA:	0.682 ? 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%):	0.925	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	72.698%	Volume Distribution (VD):	-0.366
Fu:	23.024% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.042
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.682
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.238
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.342	CYP3A4-substrate:	0.342
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

4.062

Half-life (T1/2):

0.736

ADMET: Toxicity

hERG Blockers:	0.077	hERG Blockers (10um):	0.632
Human Hepatotoxicity (H-HT):	0.087	Drug-induced Liver Injury (DILI):	0.389
AMES Toxicity:	0.193	Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.459	Skin Sensitization:	0.844
Carcinogencity:	0.394	Eye Corrosion:	0.003
Eye Irritation:	0.603	Respiratory Toxicity:	0.183
Drug-induced Neurotoxicity:	0.132	Ototoxicity:	0.302
Hematotoxicity:	0.04	Drug-induced Nephrotoxicity:	0.313
Genotoxicity:	0.511	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.033	Hek293 Cytotoxicity:	0.158
BCF:	0.656 ? 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:	3.558 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.441 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.69 ? 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
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	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
MIC	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
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[18183025]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	25.0	ug.mL-1	PMID[17126018]

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 NPC95810 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	12549
0.1-0.2	34704
0.2-0.3	1940
0.3-0.4	474
0.4-0.5	120
0.5-0.6	43
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC163719
0.8286	Intermediate Similarity	NPC301368
0.8286	Intermediate Similarity	NPC84815
0.7945	Intermediate Similarity	NPC253738
0.7639	Intermediate Similarity	NPC125106
0.7639	Intermediate Similarity	NPC472573
0.7576	Intermediate Similarity	NPC200471
0.7576	Intermediate Similarity	NPC472575
0.7397	Intermediate Similarity	NPC610927
0.7143	Intermediate Similarity	NPC57628
0.6912	Remote Similarity	NPC483886
0.6667	Remote Similarity	NPC87448
0.6571	Remote Similarity	NPC291599
0.6557	Remote Similarity	NPC470154
0.6479	Remote Similarity	NPC472572
0.6471	Remote Similarity	NPC66761
0.6471	Remote Similarity	NPC483843
0.6429	Remote Similarity	NPC281717
0.6216	Remote Similarity	NPC472570
0.6098	Remote Similarity	NPC30171
0.6	Remote Similarity	NPC211137
0.6	Remote Similarity	NPC476094
0.5823	Remote Similarity	NPC4421
0.5789	Remote Similarity	NPC472569
0.5789	Remote Similarity	NPC16912
0.5769	Remote Similarity	NPC470153
0.5733	Remote Similarity	NPC171207
0.5696	Remote Similarity	NPC481486
0.5694	Remote Similarity	NPC118080
0.5616	Remote Similarity	NPC97947
0.5616	Remote Similarity	NPC483862
0.56	Remote Similarity	NPC270590
0.557	Remote Similarity	NPC481489
0.5556	Remote Similarity	NPC70403
0.5556	Remote Similarity	NPC475429
0.5556	Remote Similarity	NPC177940
0.5556	Remote Similarity	NPC481047
0.5556	Remote Similarity	NPC481045
0.5542	Remote Similarity	NPC148896
0.5526	Remote Similarity	NPC471104
0.55	Remote Similarity	NPC481488
0.5488	Remote Similarity	NPC611111
0.5467	Remote Similarity	NPC90257
0.5467	Remote Similarity	NPC69357
0.5432	Remote Similarity	NPC212768
0.5405	Remote Similarity	NPC90614
0.5395	Remote Similarity	NPC158663
0.5385	Remote Similarity	NPC11685
0.5375	Remote Similarity	NPC481062
0.5375	Remote Similarity	NPC481058
0.5375	Remote Similarity	NPC481060
0.5316	Remote Similarity	NPC127720
0.5244	Remote Similarity	NPC603877
0.5238	Remote Similarity	NPC56953
0.52	Remote Similarity	NPC241951
0.5195	Remote Similarity	NPC471101
0.5185	Remote Similarity	NPC294803
0.5132	Remote Similarity	NPC163087
0.5128	Remote Similarity	NPC473758
0.5125	Remote Similarity	NPC96903
0.5125	Remote Similarity	NPC481063
0.5068	Remote Similarity	NPC283375
0.5065	Remote Similarity	NPC483845
0.5063	Remote Similarity	NPC483844
0.506	Remote Similarity	NPC608007

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC95810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3789
0.1-0.2	5204
0.2-0.3	155
0.3-0.4	2
0.4-0.5	0
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