NPASS Compound

Natural Product: NPC474164

Natural Product ID	NPC474164
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Veramiline
IUPAC Name	(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms	Veramiline
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL463130
PubChem CID	15559023
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002732] 22,26-epiminocholestanes

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 74 78 0 0 0 0 0 0 0 0999 V2000 6.8195 2.2592 0.2277 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4356 2.2307 0.8875 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3730 2.4945 -0.1258 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2708 1.4656 -0.1372 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7927 0.0706 -0.2842 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0057 -0.1303 0.4783 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1927 0.8752 1.5037 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7712 -0.9509 0.1739 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4021 -2.2990 -0.0146 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5074 -0.7266 -0.5565 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5898 -0.8489 -2.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1262 -0.8484 -2.4379 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6935 -1.0810 -1.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3327 -1.5417 -0.1910 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2407 -1.2268 1.1632 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7628 -1.4385 1.1406 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3173 -0.2030 0.4234 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4815 0.1075 -0.7587 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3013 0.5693 -1.9692 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4963 1.3327 -1.5416 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2154 0.9512 -0.5103 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7902 -0.2697 0.2104 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4949 -0.3301 1.5504 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7740 1.0652 2.0865 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8997 1.6053 1.2308 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3923 1.7741 -0.1558 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9060 0.6422 1.2290 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2659 -1.4516 -0.5920 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4696 -3.0153 -0.3702 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4599 1.4580 0.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2863 3.2548 0.3171 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6552 2.0812 -0.8707 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4769 2.9833 1.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8861 3.4708 0.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8352 2.6515 -1.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5854 1.7395 -0.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7373 1.5598 0.8365 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0644 -0.0754 -1.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8467 -0.2396 -0.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3280 0.9213 2.1645 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0916 0.6030 2.0703 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6311 -0.7967 1.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4322 -2.6438 -1.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4896 -2.1756 0.2776 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0169 -3.0522 0.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2187 0.3509 -0.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0615 0.0190 -2.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1272 -1.7508 -2.3868 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0031 -1.7383 -3.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1356 0.0252 -3.0429 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4226 -1.9107 -1.3807 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1441 -1.9170 1.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0251 -0.2102 1.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9595 -2.3662 0.6101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0476 -1.4514 2.2171 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1625 0.6278 1.1793 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7816 0.9643 -0.5607 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5174 -0.2869 -2.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6867 1.2666 -2.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7968 2.2406 -2.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5003 -0.7773 1.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0088 -0.9388 2.3027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1634 0.9371 3.1112 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8746 1.6801 2.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2791 2.5853 1.6174 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0629 2.8496 -0.2625 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2147 1.6749 -0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6976 0.9099 0.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6271 -2.3314 -0.5537 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5182 -1.1690 -1.6576 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2686 -1.8018 -0.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5459 -3.4220 -0.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1391 -3.3258 -1.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6787 -3.5549 0.5943 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 5 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 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 22 28 1 0 14 29 1 0 7 2 1 0 14 10 1 0 18 13 1 0 22 17 1 0 26 21 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 4 36 1 0 4 37 1 0 5 38 1 0 6 39 1 0 7 40 1 0 7 41 1 0 8 42 1 0 9 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 25 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 29 74 1 0 M END

Standard InCHIKey	SWTXHUUBYZNDAJ-BXTYSGRPSA-N
Standard InCHI	InChI=1S/C27H45NO/c1-17-5-10-25(28-16-17)18(2)22-8-9-23-21-7-6-19-15-20(29)11-13-26(19,3)24(21)12-14-27(22,23)4/h6,17-18,20-25,28-29H,5,7-16H2,1-4H3/t17-,18-,20-,21-,22+,23-,24-,25-,26-,27+/m0/s1
SMILES	CC1CCC(NC1)C(C)C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	399.35	Volume:	449.916 ? Van der Waals volume.
Dense:	0.888	LogP:	4.709 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.209 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.951 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	32.26 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.562	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.683	Fsp³:	0.926
MCE-18:	83.077 ? 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:	0.691	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.011 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.022

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.187	MDCK Permeability:	-5.005
Pgp-inhibitor:	0.004	Pgp-substrate:	0.019
PAMPA:	0.579 ? 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%):	0.0	30% Bioavailability (F30%):	0.01
50% Bioavailability (F50%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992	MRP1:	1.0
Plasma Protein Binding (PPB):	57.508%	Volume Distribution (VD):	0.114
Fu:	41.983% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.231	BCRP inhibitor:	0.008
BSEP inhibitor:	0.823

ADMET: Metabolism

CYP1A2-inhibitor:	0.079	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.179
CYP2D6-inhibitor:	0.047	CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.975	CYP3A4-substrate:	0.425
CYP2B6-substrate:	0.057	CYP2C8-inhibitor:	0.008
HLM stability:	0.826 ? 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):

16.624

Half-life (T1/2):

0.883

ADMET: Toxicity

hERG Blockers:	0.617	hERG Blockers (10um):	0.792
Human Hepatotoxicity (H-HT):	0.868	Drug-induced Liver Injury (DILI):	0.099
AMES Toxicity:	0.056	Rat Oral Acute Toxicity:	0.281
Maximum Recommended Daily Dose:	0.88	Skin Sensitization:	0.04
Carcinogencity:	0.166	Eye Corrosion:	0.002
Eye Irritation:	0.019	Respiratory Toxicity:	0.931
Drug-induced Neurotoxicity:	0.531	Ototoxicity:	0.962
Hematotoxicity:	0.13	Drug-induced Nephrotoxicity:	0.325
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.42	Hek293 Cytotoxicity:	0.554
BCF:	2.38 ? 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:	4.71 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.773 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.452 ? 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
NPO33146	eclipta alba	Species	n.a.	Eukaryota	n.a.	suriname rainforest1	n.a.	PMID[9784152]

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
IC12	3

Activity Type	# Activity
Organism	3

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
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	3.0	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	4.0	ug ml-1	PMID[24900724]

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 NPC474164 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	25164
0.1-0.2	22387
0.2-0.3	2041
0.3-0.4	157
0.4-0.5	55
0.5-0.6	32
0.6-0.7	20
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
0.7833	Intermediate Similarity	NPC176012
0.6833	Remote Similarity	NPC12035
0.6552	Remote Similarity	NPC107059
0.6441	Remote Similarity	NPC136188
0.6441	Remote Similarity	NPC28657
0.6379	Remote Similarity	NPC162742
0.6379	Remote Similarity	NPC304309
0.6379	Remote Similarity	NPC470228
0.6333	Remote Similarity	NPC134847
0.6271	Remote Similarity	NPC22105
0.6271	Remote Similarity	NPC34019
0.6271	Remote Similarity	NPC600590
0.623	Remote Similarity	NPC155986
0.6167	Remote Similarity	NPC474216
0.6167	Remote Similarity	NPC154330
0.6129	Remote Similarity	NPC321381
0.6066	Remote Similarity	NPC230301
0.6066	Remote Similarity	NPC113733
0.6066	Remote Similarity	NPC198968
0.6066	Remote Similarity	NPC285893
0.6	Remote Similarity	NPC221758
0.5968	Remote Similarity	NPC241290
0.5968	Remote Similarity	NPC164840
0.5968	Remote Similarity	NPC484739
0.5968	Remote Similarity	NPC209944
0.5968	Remote Similarity	NPC264245
0.5781	Remote Similarity	NPC472265
0.5781	Remote Similarity	NPC33913
0.5781	Remote Similarity	NPC59453
0.5775	Remote Similarity	NPC147835
0.5775	Remote Similarity	NPC253645
0.5775	Remote Similarity	NPC85001
0.5775	Remote Similarity	NPC95920
0.5714	Remote Similarity	NPC51014
0.5692	Remote Similarity	NPC603646
0.5625	Remote Similarity	NPC328714
0.5606	Remote Similarity	NPC243985
0.5606	Remote Similarity	NPC473943
0.5606	Remote Similarity	NPC280710
0.5606	Remote Similarity	NPC240650
0.5606	Remote Similarity	NPC155011
0.5538	Remote Similarity	NPC318495
0.5522	Remote Similarity	NPC47761
0.5522	Remote Similarity	NPC488870
0.5455	Remote Similarity	NPC477522
0.5424	Remote Similarity	NPC96319
0.5397	Remote Similarity	NPC328313
0.5373	Remote Similarity	NPC174117
0.5286	Remote Similarity	NPC601043
0.5286	Remote Similarity	NPC605412
0.5185	Remote Similarity	NPC296686
0.5075	Remote Similarity	NPC1272
0.5075	Remote Similarity	NPC470614

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7445
0.1-0.2	1578
0.2-0.3	113
0.3-0.4	8
0.4-0.5	1
0.5-0.6	1
0.6-0.7	3
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
0.6441	Remote Similarity	NPD6942	Phase 4
0.6066	Remote Similarity	NPD7339	Approved
0.6	Remote Similarity	NPD4786	Phase 1
0.5424	Remote Similarity	NPD3701	Pre-clinical

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