NPASS Compound

Natural Product: NPC548566

Natural Product ID	NPC548566
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ergost-5-en-3-ol
IUPAC Name	(8~{S},9~{S},10~{R},13~{R},14~{S},17~{R})-10,13-dimethyl-17-[(1~{R},4~{S})-1,4,5-trimethylhexyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthren-3-ol
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 77 80 0 0 0 0 0 0 0 0999 V2000 -7.1477 0.8761 -0.5986 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8123 -0.5856 -0.5170 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6521 -1.2876 0.5057 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3337 -0.6341 -0.0077 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9858 -2.1284 0.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4869 0.0733 -1.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0252 0.1975 -0.7675 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5263 0.9607 0.3861 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9440 0.3973 1.6817 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1246 1.4504 0.2914 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7984 2.2197 1.5493 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4528 1.5369 2.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1121 1.1852 0.8267 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3773 0.4642 0.8552 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4315 1.3646 1.5059 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6670 0.5311 1.5651 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9651 -0.2822 0.5687 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2017 -1.0937 0.6654 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0014 -0.8369 -0.5996 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2706 -0.4019 -0.1977 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4024 0.2827 -1.4206 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9824 0.0252 -1.8234 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1278 -0.4289 -0.6460 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8876 -1.9249 -0.8656 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8469 0.3226 -0.5851 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7975 -0.1989 -1.5104 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5124 0.5827 -1.3995 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0180 0.5177 0.0443 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2090 -0.9080 0.3829 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0555 1.2410 -1.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2105 0.9948 -0.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5274 1.4774 0.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8171 -1.0554 -1.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4828 -0.5817 0.7973 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1238 -1.5636 1.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1303 -2.1816 0.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3982 -0.2489 0.9945 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5361 -2.6817 -0.7173 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9127 -2.3167 0.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3673 -2.5357 1.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9301 1.0904 -1.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6726 -0.4872 -1.9894 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5489 -1.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6791 -0.8963 -0.6910 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1186 1.9543 0.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1455 0.4505 2.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2075 -0.6743 1.6601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8009 0.9217 2.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1002 2.1972 -0.5597 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5974 2.3587 2.2548 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4262 3.2599 1.3003 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0117 2.2298 2.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2338 0.6379 2.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2833 2.1626 0.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4343 -0.4682 1.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1128 1.7155 2.4880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6563 2.1974 0.7925 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3349 0.5767 2.4161 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7815 -0.8454 1.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9709 -2.1854 0.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1532 -1.7351 -1.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5249 -0.7634 0.6846 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0045 0.3329 -2.3603 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5365 1.2653 -0.9283 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9708 -0.6731 -2.6581 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5652 1.0093 -2.1754 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3580 -2.0840 -1.8472 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8672 -2.4316 -0.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2804 -2.3647 -0.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0704 1.3795 -0.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1659 -0.0728 -2.5423 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5542 -1.2575 -1.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1911 0.1722 -2.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7394 1.6424 -1.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7567 -1.3604 0.7538 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3785 -1.4851 -0.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9317 -1.1433 1.1593 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 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 28 10 1 0 28 13 1 0 25 14 1 0 23 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 1 5 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 8 45 1 6 9 46 1 0 9 47 1 0 9 48 1 0 10 49 1 6 11 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 6 14 55 1 1 15 56 1 0 15 57 1 0 16 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 24 67 1 0 24 68 1 0 24 69 1 0 25 70 1 6 26 71 1 0 26 72 1 0 27 73 1 0 27 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 M END

Standard InCHIKey	SGNBVLSWZMBQTH-AUZDMFNXSA-N
Standard InCHI	InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20+,22?,23-,24+,25-,26-,27-,28+/m0/s1
SMILES	CC(C)[C@@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	400.37	Volume:	464.772 ? Van der Waals volume.
Dense:	0.861	LogP:	7.557 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.078 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.017 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	20.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.47	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.35	Fsp³:	0.929
MCE-18:	69.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.842	Fluc inhibitor:	0.016 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.627	Promiscuous compounds:	0.009

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.369	MDCK Permeability:	-5.005
Pgp-inhibitor:	0.001	Pgp-substrate:	0.044
PAMPA:	0.083 ? 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%):	0.04	30% Bioavailability (F30%):	0.702
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258	MRP1:	0.042
Plasma Protein Binding (PPB):	75.881%	Volume Distribution (VD):	-0.068
Fu:	27.032% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.742
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.883	CYP2C19-substrate:	0.422
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.519
CYP2D6-inhibitor:	0.012	CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.914 ? 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):

15.084

Half-life (T1/2):

0.603

ADMET: Toxicity

hERG Blockers:	0.273	hERG Blockers (10um):	0.58
Human Hepatotoxicity (H-HT):	0.666	Drug-induced Liver Injury (DILI):	0.161
AMES Toxicity:	0.144	Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.372	Skin Sensitization:	0.951
Carcinogencity:	0.825	Eye Corrosion:	0.621
Eye Irritation:	0.964	Respiratory Toxicity:	0.764
Drug-induced Neurotoxicity:	0.095	Ototoxicity:	0.572
Hematotoxicity:	0.457	Drug-induced Nephrotoxicity:	0.594
Genotoxicity:	0.005	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.389	Hek293 Cytotoxicity:	0.453
BCF:	3.286 ? 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:	4.818 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.321 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.629 ? 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
NPO46434	Cymbopogon jwarancusa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37714225]
NPO23593	Drynaria quercifolia	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23593	Drynaria quercifolia	Species	Polypodiaceae	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
NPO46434	Cymbopogon jwarancusa	Hydroalcoholic extract	n.a.	0.78	n.a.	n.a.	%	PMID[37714225]

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 NPC548566 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	23897
0.1-0.2	21793
0.2-0.3	3722
0.3-0.4	276
0.4-0.5	66
0.5-0.6	53
0.6-0.7	18
0.7-0.8	1
0.8-0.85	9
0.85-0.9	6
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC162742
1.0	High Similarity	NPC304309
1.0	High Similarity	NPC470228
0.8936	High Similarity	NPC230301
0.8913	High Similarity	NPC34019
0.8542	High Similarity	NPC198968
0.8542	High Similarity	NPC285893
0.8511	High Similarity	NPC22105
0.8511	High Similarity	NPC107059
0.8333	Intermediate Similarity	NPC136188
0.8333	Intermediate Similarity	NPC28657
0.8333	Intermediate Similarity	NPC474216
0.8163	Intermediate Similarity	NPC134847
0.8	Intermediate Similarity	NPC241290
0.8	Intermediate Similarity	NPC164840
0.8	Intermediate Similarity	NPC484739
0.8	Intermediate Similarity	NPC209944
0.8	Intermediate Similarity	NPC155986
0.7843	Intermediate Similarity	NPC321381
0.7692	Intermediate Similarity	NPC59453
0.7647	Intermediate Similarity	NPC264245
0.76	Intermediate Similarity	NPC154330
0.7547	Intermediate Similarity	NPC603646
0.7451	Intermediate Similarity	NPC113733
0.7407	Intermediate Similarity	NPC473943
0.74	Intermediate Similarity	NPC600590
0.7358	Intermediate Similarity	NPC472265
0.7273	Intermediate Similarity	NPC488870
0.7091	Intermediate Similarity	NPC155011
0.7059	Intermediate Similarity	NPC221758
0.6981	Remote Similarity	NPC51014
0.6964	Remote Similarity	NPC47761
0.6727	Remote Similarity	NPC33913
0.6604	Remote Similarity	NPC328313
0.6545	Remote Similarity	NPC328714
0.6538	Remote Similarity	NPC81306
0.6491	Remote Similarity	NPC243985
0.6491	Remote Similarity	NPC280710
0.6491	Remote Similarity	NPC240650
0.6429	Remote Similarity	NPC318495
0.64	Remote Similarity	NPC96319
0.6379	Remote Similarity	NPC474164
0.6316	Remote Similarity	NPC477522
0.625	Remote Similarity	NPC87604
0.6066	Remote Similarity	NPC601043
0.6066	Remote Similarity	NPC605412
0.6034	Remote Similarity	NPC474752
0.6034	Remote Similarity	NPC474683
0.5965	Remote Similarity	NPC145879
0.5893	Remote Similarity	NPC28862
0.5862	Remote Similarity	NPC1272
0.5862	Remote Similarity	NPC470614
0.5818	Remote Similarity	NPC151519
0.5714	Remote Similarity	NPC20688
0.569	Remote Similarity	NPC31564
0.5645	Remote Similarity	NPC474970
0.5614	Remote Similarity	NPC76879
0.5593	Remote Similarity	NPC474778
0.5593	Remote Similarity	NPC474733
0.55	Remote Similarity	NPC474759
0.55	Remote Similarity	NPC44083
0.5439	Remote Similarity	NPC109546
0.5439	Remote Similarity	NPC247325
0.5439	Remote Similarity	NPC317458
0.5439	Remote Similarity	NPC47982
0.5424	Remote Similarity	NPC26959
0.5397	Remote Similarity	NPC474189
0.5345	Remote Similarity	NPC84694
0.5345	Remote Similarity	NPC143182
0.5345	Remote Similarity	NPC20610
0.5345	Remote Similarity	NPC609126
0.5312	Remote Similarity	NPC176012
0.5254	Remote Similarity	NPC317927
0.5246	Remote Similarity	NPC474732
0.5246	Remote Similarity	NPC58063
0.5238	Remote Similarity	NPC475032
0.5231	Remote Similarity	NPC5985
0.5224	Remote Similarity	NPC235126
0.5224	Remote Similarity	NPC309493
0.5224	Remote Similarity	NPC242419
0.5217	Remote Similarity	NPC22140
0.5217	Remote Similarity	NPC243728
0.5172	Remote Similarity	NPC189972
0.5167	Remote Similarity	NPC476082
0.5167	Remote Similarity	NPC470383
0.5161	Remote Similarity	NPC7505
0.5161	Remote Similarity	NPC475789
0.5161	Remote Similarity	NPC82986
0.5161	Remote Similarity	NPC268406
0.5156	Remote Similarity	NPC474349
0.5152	Remote Similarity	NPC91604
0.5147	Remote Similarity	NPC147835
0.5147	Remote Similarity	NPC253645
0.5147	Remote Similarity	NPC85001
0.5147	Remote Similarity	NPC95920
0.5143	Remote Similarity	NPC3715
0.5082	Remote Similarity	NPC153987
0.5082	Remote Similarity	NPC474634
0.5077	Remote Similarity	NPC475033
0.5077	Remote Similarity	NPC599942
0.5072	Remote Similarity	NPC486119

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC548566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7737
0.1-0.2	1238
0.2-0.3	135
0.3-0.4	33
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD7339	Approved
0.8333	Intermediate Similarity	NPD6942	Phase 4
0.7059	Intermediate Similarity	NPD4786	Phase 1
0.64	Remote Similarity	NPD3701	Pre-clinical
0.5818	Remote Similarity	NPD3667	Phase 4

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