NPASS Compound

Natural Product: NPC483844

Natural Product ID	NPC483844
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BQHQKRNENCCQIT-NMJVBZPESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	134138683
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 88 91 0 0 0 0 0 0 0 0999 V2000 -3.3494 -2.5862 -0.9109 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1770 -3.0606 -0.1217 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5243 -3.5573 1.2521 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3507 -2.6001 2.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1436 -1.7283 2.3003 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0650 -1.0458 0.9219 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2782 -0.1882 0.8339 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3572 0.5284 -0.4082 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4243 1.3778 -0.6719 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2952 1.4737 0.2309 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5703 2.1457 -1.9288 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 -0.1410 0.8418 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3283 -0.7076 0.1586 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0363 -1.6492 -0.9647 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4597 -1.6620 -1.3361 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9843 -2.1879 -0.0530 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0272 -3.0438 0.4695 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0885 -3.0594 -0.3607 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1456 -4.0713 -1.4275 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3526 -3.2252 0.4958 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6309 -2.5055 -2.4468 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0804 -2.0435 -3.6731 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3406 -0.8020 -3.7683 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2616 -2.9428 -4.8530 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1507 0.3895 -0.2524 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3927 0.6631 0.2950 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7705 -0.1206 1.1940 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1790 1.8207 -0.1900 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4899 1.9279 0.5570 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4099 3.0974 0.0710 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4859 1.7244 -1.6651 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1436 1.1162 0.2415 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0700 2.3199 0.9224 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2560 2.2477 2.1431 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3410 3.6080 0.3141 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2501 4.7539 1.0648 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5047 5.9781 0.4910 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8542 6.0937 -0.8357 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9485 4.9429 -1.6008 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6882 3.7041 -1.0105 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3163 -0.6725 3.2414 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4096 -0.4443 4.2628 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5990 -1.1718 4.3853 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7130 0.6992 5.1811 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7977 -3.4028 -1.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2303 -2.3166 -0.2536 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1237 -1.7837 -1.6418 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8275 -3.9962 -0.6697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6006 -3.9045 1.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9500 -4.4996 1.5027 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2995 -2.0242 2.5869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2334 -3.2091 3.3160 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2346 -2.3004 2.4978 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2262 -0.6348 1.1110 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1095 0.6376 1.5926 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7315 3.2256 -1.7610 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7774 1.9565 -2.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5224 1.7717 -2.4075 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3881 0.1036 1.9155 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9325 -1.2074 0.9544 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6856 -1.6042 -1.8201 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7339 -0.6466 -1.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2349 -4.5557 -1.7404 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8720 -4.9006 -1.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6104 -3.5921 -2.3396 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1777 -2.5975 0.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7253 -4.2881 0.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1206 -3.1331 1.5778 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2499 -3.0357 -5.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6862 -3.9211 -4.5675 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9245 -2.4517 -5.5749 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4901 1.3786 1.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3460 1.5790 -0.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7104 2.9987 0.8288 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0614 3.9971 0.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5833 3.2359 -0.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9676 3.1036 1.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6706 2.1202 -2.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4187 2.3015 -1.8361 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7324 0.6689 -1.9006 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0165 4.7092 2.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4311 6.8833 1.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0564 7.0659 -1.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2213 5.0502 -2.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7752 2.8410 -1.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2716 1.0312 5.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4248 0.4157 5.9635 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1531 1.5349 4.6041 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 1 0 6 7 1 6 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 6 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 17 18 1 0 18 19 1 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 13 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 12 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 5 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 16 2 1 0 40 35 1 0 16 6 1 0 18 14 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 6 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 1 7 54 1 0 7 55 1 0 11 56 1 0 11 57 1 0 11 58 1 0 12 59 1 1 13 60 1 1 14 61 1 6 15 62 1 6 19 63 1 0 19 64 1 0 19 65 1 0 20 66 1 0 20 67 1 0 20 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 29 72 1 0 29 73 1 0 29 74 1 0 30 75 1 0 30 76 1 0 30 77 1 0 31 78 1 0 31 79 1 0 31 80 1 0 36 81 1 0 37 82 1 0 38 83 1 0 39 84 1 0 40 85 1 0 44 86 1 0 44 87 1 0 44 88 1 0 M END

Standard InCHIKey	BQHQKRNENCCQIT-NMJVBZPESA-N
Standard InCHI	InChI=1S/C33H44O11/c1-18-15-16-23(40-20(3)35)32(17-39-19(2)34)27(43-28(37)22-13-11-10-12-14-22)25(42-29(38)30(5,6)7)24-26(41-21(4)36)33(18,32)44-31(24,8)9/h10-14,18,23-27H,15-17H2,1-9H3/t18-,23+,24-,25-,26-,27-,32+,33-/m1/s1
SMILES	C[C@@H]1CC[C@@H]([C@@]2(COC(=O)C)[C@@H]([C@@H]([C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)C)OC(=O)C(C)(C)C)OC(=O)c1ccccc1)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	616.29	Volume:	620.699 ? Van der Waals volume.
Dense:	0.993	LogP:	3.015 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.969 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.492 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	25.0
TPSA:	140.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.322	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.893	Fsp³:	0.667
MCE-18:	158.4 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.411	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.036 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.205	Promiscuous compounds:	0.059

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.034	MDCK Permeability:	-4.723
Pgp-inhibitor:	0.999	Pgp-substrate:	0.197
PAMPA:	0.272 ? 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):	0.0
20% Bioavailability (F20%):	0.037	30% Bioavailability (F30%):	0.479
50% Bioavailability (F50%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11	MRP1:	0.998
Plasma Protein Binding (PPB):	80.944%	Volume Distribution (VD):	-0.464
Fu:	19.909% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.637
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.133
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.662
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.947
CYP3A4-inhibitor:	0.057	CYP3A4-substrate:	0.074
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):

5.472

Half-life (T1/2):

0.419

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.266
Human Hepatotoxicity (H-HT):	0.265	Drug-induced Liver Injury (DILI):	0.7
AMES Toxicity:	0.476	Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.176	Skin Sensitization:	0.937
Carcinogencity:	0.557	Eye Corrosion:	0.011
Eye Irritation:	0.321	Respiratory Toxicity:	0.036
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.329
Hematotoxicity:	0.184	Drug-induced Nephrotoxicity:	0.491
Genotoxicity:	0.714	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.042	Hek293 Cytotoxicity:	0.085
BCF:	0.783 ? 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:	3.8 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.861 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.198 ? 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
NPO40494	Maytenus bilocularis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27120798]

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
FC	2
Inhibition	1

Activity Type	# Activity
Others	1
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	FC	=	1.5	n.a.	PMID[27120798]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	25.6	%	PMID[27120798]
NPT2	Others	Unspecified	n.a.	FC	=	123.7	n.a.	PMID[27120798]

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 NPC483844 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	15915
0.1-0.2	31866
0.2-0.3	1553
0.3-0.4	362
0.4-0.5	90
0.5-0.6	41
0.6-0.7	20
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9194	High Similarity	NPC90257
0.9194	High Similarity	NPC69357
0.8889	High Similarity	NPC483845
0.8382	Intermediate Similarity	NPC483848
0.8	Intermediate Similarity	NPC483849
0.7164	Intermediate Similarity	NPC66761
0.7164	Intermediate Similarity	NPC483843
0.6912	Remote Similarity	NPC211137
0.6912	Remote Similarity	NPC476094
0.6901	Remote Similarity	NPC483842
0.6857	Remote Similarity	NPC473060
0.6857	Remote Similarity	NPC17877
0.6709	Remote Similarity	NPC473115
0.6667	Remote Similarity	NPC475429
0.6667	Remote Similarity	NPC137718
0.6667	Remote Similarity	NPC148062
0.6622	Remote Similarity	NPC479043
0.6622	Remote Similarity	NPC481059
0.662	Remote Similarity	NPC51314
0.6528	Remote Similarity	NPC147880
0.6486	Remote Similarity	NPC306146
0.6486	Remote Similarity	NPC483841
0.64	Remote Similarity	NPC252314
0.6351	Remote Similarity	NPC473758
0.6125	Remote Similarity	NPC479040
0.6081	Remote Similarity	NPC48017
0.6	Remote Similarity	NPC483846
0.5977	Remote Similarity	NPC488902
0.5977	Remote Similarity	NPC488903
0.5974	Remote Similarity	NPC57628
0.5926	Remote Similarity	NPC488900
0.5926	Remote Similarity	NPC488899
0.5921	Remote Similarity	NPC473088
0.5867	Remote Similarity	NPC246480
0.5811	Remote Similarity	NPC90614
0.5789	Remote Similarity	NPC147217
0.5658	Remote Similarity	NPC4341
0.5658	Remote Similarity	NPC479047
0.5658	Remote Similarity	NPC291638
0.561	Remote Similarity	NPC4421
0.557	Remote Similarity	NPC472569
0.557	Remote Similarity	NPC16912
0.5541	Remote Similarity	NPC481047
0.5541	Remote Similarity	NPC481045
0.5479	Remote Similarity	NPC474608
0.5455	Remote Similarity	NPC191082
0.5443	Remote Similarity	NPC479044
0.5422	Remote Similarity	NPC212768
0.5375	Remote Similarity	NPC11685
0.5375	Remote Similarity	NPC472570
0.5316	Remote Similarity	NPC254558
0.5316	Remote Similarity	NPC471107
0.5301	Remote Similarity	NPC481486
0.527	Remote Similarity	NPC283375
0.527	Remote Similarity	NPC183122
0.525	Remote Similarity	NPC41481
0.5195	Remote Similarity	NPC241951
0.5195	Remote Similarity	NPC483847
0.5195	Remote Similarity	NPC483862
0.5185	Remote Similarity	NPC609924
0.5181	Remote Similarity	NPC481489
0.5125	Remote Similarity	NPC171207
0.5125	Remote Similarity	NPC471100
0.5125	Remote Similarity	NPC605884
0.5122	Remote Similarity	NPC184747
0.5119	Remote Similarity	NPC481488
0.5063	Remote Similarity	NPC163719
0.5063	Remote Similarity	NPC95810

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3844
0.1-0.2	5162
0.2-0.3	144
0.3-0.4	0
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