NPASS Compound

Natural Product: NPC486521

Natural Product ID	NPC486521
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GKQMMZUXYRXFOH-WPDXTOJRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 81 85 0 0 0 0 0 0 0 0999 V2000 3.3427 -0.6897 -1.3782 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2697 -0.0282 -0.0300 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6677 1.3809 -0.1539 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1195 1.4525 -0.6743 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0552 0.7715 0.2631 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9399 -0.2736 -0.3660 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1515 -0.3581 -1.8555 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1957 -1.5604 0.3814 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4367 0.9133 0.1685 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4148 2.8318 -0.5905 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9816 -0.3125 0.6361 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8707 0.3196 2.0131 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3764 0.6028 2.2331 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2272 -0.2475 1.1681 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1159 -1.6839 1.5537 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5880 0.0947 0.7781 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2672 0.9787 1.4482 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6515 1.3133 1.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2695 0.0490 0.5117 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7480 0.2162 0.3291 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1714 1.5615 -0.1723 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3755 0.0602 1.7233 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2469 -0.9034 -0.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2886 -0.8231 -1.0739 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4402 -2.1354 -0.5469 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1013 -1.8234 -1.0996 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5371 -0.4710 -0.6958 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8034 0.4478 -1.8907 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1037 -0.6523 -0.4123 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1792 -0.2888 -1.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2640 -0.6145 -1.2071 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7183 0.1039 0.0027 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5782 1.5840 -0.2179 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3907 -1.0836 -1.5458 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7123 -1.5986 -1.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2075 0.0410 -2.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0563 -0.5396 0.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6554 2.0083 0.7297 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0855 1.8254 -1.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1803 1.1437 -1.7055 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7294 0.5544 1.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2409 -0.5822 -1.9993 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9672 0.5696 -2.4004 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6227 -1.2311 -2.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9946 -2.1125 -0.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6104 -1.2917 1.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3123 -2.2142 0.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0310 3.2148 0.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9235 -1.4197 0.8010 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4551 1.2373 2.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2344 -0.4114 2.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1749 1.6874 2.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1128 0.1925 3.2257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6520 -1.8505 2.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0368 -2.3778 0.7138 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0916 -1.9841 2.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8077 1.4657 2.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5682 2.1223 0.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2276 1.6257 1.9281 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1243 -0.7244 1.3183 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5882 2.3751 0.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2378 1.7497 0.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1996 1.6486 -1.2765 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8107 -0.6519 2.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2919 1.0571 2.2470 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4575 -0.1501 1.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3102 -2.6110 0.4468 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9292 -2.8900 -1.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4054 -2.6563 -0.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1620 -1.9230 -2.2183 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0045 0.3202 -2.6652 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7387 0.1104 -2.3910 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8186 1.5048 -1.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8753 -1.7382 -0.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4433 -0.9654 -2.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2070 0.7761 -1.8171 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 -0.2496 -2.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3684 -1.7112 -1.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2017 2.2072 0.4172 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7105 1.8653 -1.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4808 1.8496 0.0016 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 0 6 8 1 0 6 9 1 0 4 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 0 20 22 1 0 20 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 9 5 1 0 32 11 1 0 32 14 1 0 29 16 1 0 27 19 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 1 3 38 1 0 3 39 1 0 4 40 1 6 5 41 1 1 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 10 48 1 0 11 49 1 1 12 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 15 54 1 0 15 55 1 0 15 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 1 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 22 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 26 70 1 0 28 71 1 0 28 72 1 0 28 73 1 0 29 74 1 1 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 M END

Standard InCHIKey	GKQMMZUXYRXFOH-WPDXTOJRSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-18(17-22(31)25-27(4,5)33-25)19-11-15-30(8)21-9-10-23-26(2,3)24(32)13-14-28(23,6)20(21)12-16-29(19,30)7/h9,18-20,22-23,25,31H,10-17H2,1-8H3/t18-,19+,20-,22+,23-,25-,28+,29+,30-/m0/s1
SMILES	C[C@@H](C[C@H]([C@H]1C(C)(C)O1)O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	505.751 ? Van der Waals volume.
Dense:	0.902	LogP:	4.7 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.935 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.595 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	49.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.377	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.952	Fsp³:	0.9
MCE-18:	97.333 ? 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:	0.979	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.318	Promiscuous compounds:	0.328

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74	MDCK Permeability:	-4.818
Pgp-inhibitor:	0.368	Pgp-substrate:	0.0
PAMPA:	0.827 ? 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%):	0.022	30% Bioavailability (F30%):	0.074
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113	MRP1:	0.12
Plasma Protein Binding (PPB):	89.298%	Volume Distribution (VD):	0.156
Fu:	12.26% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.912
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.987 ? 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):

12.367

Half-life (T1/2):

0.518

ADMET: Toxicity

hERG Blockers:	0.09	hERG Blockers (10um):	0.376
Human Hepatotoxicity (H-HT):	0.585	Drug-induced Liver Injury (DILI):	0.458
AMES Toxicity:	0.247	Rat Oral Acute Toxicity:	0.325
Maximum Recommended Daily Dose:	0.578	Skin Sensitization:	0.84
Carcinogencity:	0.854	Eye Corrosion:	0.017
Eye Irritation:	0.472	Respiratory Toxicity:	0.703
Drug-induced Neurotoxicity:	0.349	Ototoxicity:	0.53
Hematotoxicity:	0.567	Drug-induced Nephrotoxicity:	0.726
Genotoxicity:	0.681	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.174	Hek293 Cytotoxicity:	0.536
BCF:	2.605 ? 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:	4.655 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.614 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.434 ? 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
NPO22908	Walsura robusta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26936592]
NPO22908	Walsura robusta	Species	Meliaceae	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
IC50	1

Activity Type	# Activity
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1137	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	<	50.0	%	PMID[26936592]
NPT4862	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	Inhibition	>	50.0	%	PMID[26936592]
NPT4862	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	IC50	=	690.0	nM	PMID[26936592]

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 NPC486521 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	18540
0.1-0.2	24856
0.2-0.3	5813
0.3-0.4	514
0.4-0.5	77
0.5-0.6	29
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC262870
0.7581	Intermediate Similarity	NPC90652
0.7581	Intermediate Similarity	NPC155255
0.7302	Intermediate Similarity	NPC125399
0.7302	Intermediate Similarity	NPC486522
0.7231	Intermediate Similarity	NPC471224
0.7031	Intermediate Similarity	NPC260992
0.6812	Remote Similarity	NPC273669
0.6812	Remote Similarity	NPC484802
0.6812	Remote Similarity	NPC118647
0.6769	Remote Similarity	NPC470052
0.6714	Remote Similarity	NPC73506
0.6667	Remote Similarity	NPC470078
0.6667	Remote Similarity	NPC470047
0.6667	Remote Similarity	NPC470046
0.6618	Remote Similarity	NPC67831
0.6618	Remote Similarity	NPC174051
0.6575	Remote Similarity	NPC484792
0.6522	Remote Similarity	NPC479667
0.6515	Remote Similarity	NPC470417
0.6301	Remote Similarity	NPC63023
0.6301	Remote Similarity	NPC95243
0.6286	Remote Similarity	NPC605437
0.6212	Remote Similarity	NPC470223
0.6081	Remote Similarity	NPC121566
0.6081	Remote Similarity	NPC100955
0.5921	Remote Similarity	NPC189282
0.5921	Remote Similarity	NPC237402
0.5915	Remote Similarity	NPC470050
0.5915	Remote Similarity	NPC472239
0.5915	Remote Similarity	NPC470051
0.5833	Remote Similarity	NPC6190
0.5753	Remote Similarity	NPC293081
0.5714	Remote Similarity	NPC2983
0.5694	Remote Similarity	NPC317590
0.5694	Remote Similarity	NPC320026
0.5652	Remote Similarity	NPC82902
0.5634	Remote Similarity	NPC481968
0.5634	Remote Similarity	NPC481967
0.5493	Remote Similarity	NPC469994
0.5467	Remote Similarity	NPC474327
0.5429	Remote Similarity	NPC474218
0.5362	Remote Similarity	NPC30166
0.5362	Remote Similarity	NPC247220
0.5333	Remote Similarity	NPC107243
0.5333	Remote Similarity	NPC488538
0.5325	Remote Similarity	NPC57416
0.5278	Remote Similarity	NPC171441
0.527	Remote Similarity	NPC484798
0.52	Remote Similarity	NPC478557
0.52	Remote Similarity	NPC154101
0.5139	Remote Similarity	NPC470077
0.5139	Remote Similarity	NPC470049
0.5128	Remote Similarity	NPC322063
0.5065	Remote Similarity	NPC218383

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6926
0.1-0.2	2027
0.2-0.3	195
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