NPASS Compound

Natural Product: NPC475880

Natural Product ID	NPC475880
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sargachromanol H
IUPAC Name	(4R,7Z,10E)-4-hydroxy-13-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydrochromen-2-yl]-2,6,10-trimethyltrideca-7,10-dien-5-one
Synonyms	Sargachromanol H
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL517913
PubChem CID	11384853
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0001546] Vitamin E 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 71 72 0 0 0 0 0 0 0 0999 V2000 -6.3277 -2.5292 1.3931 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4574 -1.2589 0.6350 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4873 -1.0767 -0.2744 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6090 0.1035 -0.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6798 1.0996 -0.7526 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6597 0.9411 0.1368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5502 -0.2664 0.8437 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4755 -0.3044 1.7142 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1569 0.1124 1.2967 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2668 1.2129 0.3086 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6128 1.9333 0.4592 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5249 0.6487 2.5867 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4944 -1.1350 0.8362 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1007 -1.0487 0.3424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9443 -0.1776 -0.8424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1853 0.8888 -0.8823 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1303 1.6750 -2.1712 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5868 1.3765 0.2429 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0580 1.4117 0.0042 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6248 1.0344 -1.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1215 1.1066 -1.2540 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5325 2.0504 -2.3454 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5644 -0.2850 -1.5141 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1061 -0.5402 -2.5610 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3438 -1.3425 -0.5141 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1570 -1.1496 0.7373 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6325 -1.1758 0.5888 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2112 -0.9679 2.0035 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2734 -0.1881 -0.3054 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6622 -2.6103 -1.0666 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6555 0.2908 -1.9023 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5666 -2.4493 2.1680 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3077 -2.6851 1.9174 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1368 -3.3991 0.7522 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2271 -1.8482 -0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7530 2.0364 -1.2918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2482 0.7811 -0.7124 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4523 1.9663 0.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6816 2.3281 1.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6841 2.7644 -0.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1156 -0.2402 3.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7156 1.3518 2.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2828 1.1458 3.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1424 -1.5553 0.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5801 -1.8731 1.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8663 -2.0983 -0.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3425 -0.9176 1.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5289 -0.4899 -1.7500 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 2.5110 -2.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0072 1.0113 -3.0504 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1368 2.1644 -2.3352 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4380 0.8549 1.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2441 2.4591 0.4059 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6664 1.7785 0.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0850 0.6601 -1.9453 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5575 1.4393 -0.2723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7286 3.0752 -1.9456 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7449 2.1773 -3.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4468 1.7392 -2.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2871 -1.4311 -0.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8925 -0.1547 1.1810 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8513 -1.9742 1.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9271 -2.2255 0.2856 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0677 -1.8749 2.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2645 -0.6857 1.8546 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6749 -0.1058 2.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8126 0.7831 -0.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4884 -0.6729 -1.3018 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3326 0.0338 0.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4598 -3.3092 -0.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3302 1.0422 -1.7500 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 9 12 1 0 9 13 1 0 13 14 1 0 14 15 1 0 15 16 2 3 16 17 1 0 16 18 1 0 18 19 1 0 19 20 2 3 20 21 1 0 21 22 1 0 21 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 25 30 1 0 4 31 1 0 7 2 1 0 11 6 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 5 36 1 0 10 37 1 0 10 38 1 0 11 39 1 0 11 40 1 0 12 41 1 0 12 42 1 0 12 43 1 0 13 44 1 0 13 45 1 0 14 46 1 0 14 47 1 0 15 48 1 0 17 49 1 0 17 50 1 0 17 51 1 0 18 52 1 0 18 53 1 0 19 54 1 0 20 55 1 0 21 56 1 0 22 57 1 0 22 58 1 0 22 59 1 0 25 60 1 0 26 61 1 0 26 62 1 0 27 63 1 0 28 64 1 0 28 65 1 0 28 66 1 0 29 67 1 0 29 68 1 0 29 69 1 0 30 70 1 0 31 71 1 0 M END

Standard InCHIKey	CHKKJDHXYINKDR-NTNCAPJNSA-N
Standard InCHI	InChI=1S/C27H40O4/c1-18(2)15-24(29)25(30)20(4)11-7-9-19(3)10-8-13-27(6)14-12-22-17-23(28)16-21(5)26(22)31-27/h7,10-11,16-18,20,24,28-29H,8-9,12-15H2,1-6H3/b11-7-,19-10+/t20?,24-,27-/m1/s1
SMILES	CC1=CC(=CC2=C1OC(CC2)(C)CCC=C(C)CC=CC(C)C(=O)C(CC(C)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	428.29	Volume:	477.777 ? Van der Waals volume.
Dense:	0.896	LogP:	5.66 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.26 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.859 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	14.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.444	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.353	Fsp³:	0.593
MCE-18:	56.512 ? 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:	0.769	Fluc inhibitor:	0.013 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.096 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.248 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.251	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.075	MDCK Permeability:	-4.717
Pgp-inhibitor:	0.054	Pgp-substrate:	0.0
PAMPA:	0.065 ? 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%):	0.041	30% Bioavailability (F30%):	0.117
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.932	MRP1:	0.996
Plasma Protein Binding (PPB):	94.734%	Volume Distribution (VD):	0.445
Fu:	5.069% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.026
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.715	CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.835	CYP2C19-substrate:	0.163
CYP2C9-inhibitor:	0.983	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.407	CYP2D6-substrate:	0.284
CYP3A4-inhibitor:	0.199	CYP3A4-substrate:	0.119
CYP2B6-substrate:	0.6	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):

6.128

Half-life (T1/2):

0.978

ADMET: Toxicity

hERG Blockers:	0.257	hERG Blockers (10um):	0.582
Human Hepatotoxicity (H-HT):	0.665	Drug-induced Liver Injury (DILI):	0.033
AMES Toxicity:	0.212	Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.484	Skin Sensitization:	0.573
Carcinogencity:	0.313	Eye Corrosion:	0.001
Eye Irritation:	0.306	Respiratory Toxicity:	0.517
Drug-induced Neurotoxicity:	0.234	Ototoxicity:	0.772
Hematotoxicity:	0.176	Drug-induced Nephrotoxicity:	0.269
Genotoxicity:	0.129	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.088	Hek293 Cytotoxicity:	0.424
BCF:	2.318 ? 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:	5.235 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.8 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.281 ? 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
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	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
IC50	2
Activity	1
MIC	6

Activity Type	# Activity
Individual protein	1
Others	2
Organism	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual protein	Isocitrate lyase	Candida albicans	IC50	>	200.0	ug.mL-1	PMID[20624681]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[1479376]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PubChem BioAssay data set
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[18077363]
NPT1	Others	Radical scavenging activity	n.a.	Activity	=	87.8	%	PMID[20143840]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[25646964]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PubChem BioAssay data set
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[9392875]
NPT2	Others	Unspecified	n.a.	IC50	=	4600.0	nM	PMID[22691179]

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 NPC475880 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	7801
0.1-0.2	39540
0.2-0.3	2404
0.3-0.4	73
0.4-0.5	7
0.5-0.6	21
0.6-0.7	10
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
0.75	Intermediate Similarity	NPC474246
0.7313	Intermediate Similarity	NPC606596
0.6486	Remote Similarity	NPC609807
0.64	Remote Similarity	NPC59654
0.6282	Remote Similarity	NPC474143
0.6232	Remote Similarity	NPC69539
0.6184	Remote Similarity	NPC271832
0.6111	Remote Similarity	NPC32152
0.6111	Remote Similarity	NPC147896
0.6081	Remote Similarity	NPC610467
0.6053	Remote Similarity	NPC474131
0.6026	Remote Similarity	NPC603704
0.5974	Remote Similarity	NPC600119
0.5974	Remote Similarity	NPC601388
0.5921	Remote Similarity	NPC232295
0.5921	Remote Similarity	NPC611336
0.5897	Remote Similarity	NPC196621
0.5844	Remote Similarity	NPC204535
0.5844	Remote Similarity	NPC46586
0.575	Remote Similarity	NPC474130
0.5714	Remote Similarity	NPC276962
0.5714	Remote Similarity	NPC190086
0.5625	Remote Similarity	NPC610755
0.5443	Remote Similarity	NPC185634
0.5316	Remote Similarity	NPC483461
0.5256	Remote Similarity	NPC483459
0.5256	Remote Similarity	NPC483457
0.5256	Remote Similarity	NPC483456
0.5256	Remote Similarity	NPC483458
0.5244	Remote Similarity	NPC474237
0.5139	Remote Similarity	NPC187993
0.5139	Remote Similarity	NPC238176
0.5119	Remote Similarity	NPC609153

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3688
0.1-0.2	5419
0.2-0.3	40
0.3-0.4	2
0.4-0.5	1
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