NPASS Compound

Natural Product: NPC476066

Natural Product ID	NPC476066
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Orizabin Xi
IUPAC Name	n.a.
Synonyms	Orizabin XI
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL524302
PubChem CID	10931187
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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 167171 0 0 0 0 0 0 0 0999 V2000 -9.3057 -2.6751 3.6016 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9803 -1.2139 3.4830 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5616 -0.8931 3.8769 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5253 -1.6124 3.0339 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6407 -1.2671 1.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6025 -1.9384 0.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7415 -3.4565 0.8776 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5985 -4.1195 0.1061 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2899 -3.9370 0.8203 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1303 -4.9441 1.9391 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8247 -6.3251 1.3454 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5152 -6.2280 0.5565 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3848 -5.8809 1.4565 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -5.3199 0.7227 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4105 -4.0000 0.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5817 -3.2702 -0.4058 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7217 -3.7704 -0.4433 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3275 -1.9895 -0.8510 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3016 -1.1201 -1.3697 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0176 -0.5376 -0.1355 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9262 -0.0786 0.8520 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0189 0.7567 0.2855 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4927 0.4380 -0.9215 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4801 0.0266 -1.9887 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2841 1.0673 -2.4315 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3847 1.4898 -3.7399 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7002 0.8948 -4.5981 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2957 2.6219 -4.0423 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2606 2.9567 -5.5213 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7285 2.2640 -3.6974 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1803 1.0552 -4.5052 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5288 3.3460 -3.9893 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3403 1.4473 -1.4355 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0618 2.0702 -0.4502 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8803 3.5667 -0.5740 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6008 4.2280 0.5831 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9681 3.6631 0.8287 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1215 2.3311 0.6166 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5755 1.8558 -0.5647 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8767 0.5448 -0.8100 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2597 0.3592 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0 0 0 0 5.1440 -1.1743 0.4976 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5342 -1.3270 1.9487 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9318 -1.9676 2.0455 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7405 -1.2639 0.9657 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2348 -1.6809 -0.3587 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8858 -2.0070 -0.3280 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3448 -0.4801 -1.3032 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1200 -1.3032 1.1678 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9021 -0.1963 1.4709 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2718 0.8839 1.5532 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3326 -0.2514 1.6817 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0175 -1.3613 1.5936 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4764 -1.4399 1.8050 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0612 0.9968 2.0165 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4614 -1.8366 3.3046 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6683 -2.0667 2.7067 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4873 -3.2678 4.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5890 -3.0839 2.6128 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1891 -2.8521 4.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6347 -0.6698 4.2203 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1480 -0.8049 2.4579 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0 3 84 1 0 4 85 1 0 4 86 1 0 5 87 1 0 5 88 1 0 6 89 1 0 7 90 1 0 7 91 1 0 8 92 1 0 8 93 1 0 9 94 1 0 9 95 1 0 10 96 1 0 10 97 1 0 11 98 1 0 11 99 1 0 12100 1 0 12101 1 0 13102 1 0 13103 1 0 14104 1 0 14105 1 0 15106 1 0 15107 1 0 19108 1 0 20109 1 0 21110 1 0 23111 1 0 24112 1 0 28113 1 0 29114 1 0 29115 1 0 29116 1 0 30117 1 0 31118 1 0 31119 1 0 31120 1 0 32121 1 0 34122 1 0 35123 1 0 36124 1 0 37125 1 0 39126 1 0 41127 1 0 42128 1 0 43129 1 0 44130 1 0 46131 1 0 48132 1 0 48133 1 0 48134 1 0 49135 1 0 50136 1 0 51137 1 0 51138 1 0 55139 1 0 56140 1 0 56141 1 0 56142 1 0 57143 1 0 57144 1 0 57145 1 0 58146 1 0 59147 1 0 60148 1 0 60149 1 0 60150 1 0 62151 1 0 63152 1 0 64153 1 0 65154 1 0 66155 1 0 68156 1 0 68157 1 0 68158 1 0 73159 1 0 74160 1 0 74161 1 0 74162 1 0 75163 1 0 75164 1 0 75165 1 0 76166 1 0 77167 1 0 M END

Standard InCHIKey	FFQUDPZHNMMQRQ-RICBYGKESA-N
Standard InCHI	InChI=1S/C54H90O23/c1-11-13-19-22-33-23-20-17-15-14-16-18-21-24-35(56)72-46-43(75-51-41(62)40(61)42(31(9)68-51)73-49(64)27(5)12-2)32(10)69-54(47(46)74-50(65)28(6)29(7)55)77-45-39(60)37(58)34(25-66-48(63)26(3)4)71-53(45)76-44-38(59)36(57)30(8)67-52(44)70-33/h12,26,28-34,36-47,51-55,57-62H,11,13-25H2,1-10H3/b27-12+/t28-,29-,30+,31+,32-,33-,34+,36+,37+,38-,39-,40+,41+,42+,43-,44+,45+,46+,47+,51-,52-,53-,54-/m0/s1
SMILES	CCCCCC1CCCCCCCCCC(=O)OC2C(C(OC(C2OC(=O)C(C)C(C)O)OC3C(C(C(OC3OC4C(C(C(OC4O1)C)O)O)COC(=O)C(C)C)O)O)C)OC5C(C(C(C(O5)C)OC(=O)C(=CC)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1106.59	Volume:	1088.75 ? Van der Waals volume.
Dense:	1.016	LogP:	4.554 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.56 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.079 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	47.0
TPSA:	320.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.057	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.782	Fsp³:	0.889
MCE-18:	113.882 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.251	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.185 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.505	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.977	MDCK Permeability:	-5.054
Pgp-inhibitor:	0.0	Pgp-substrate:	0.988
PAMPA:	0.999 ? 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):	0.941
20% Bioavailability (F20%):	0.786	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	1.0
Plasma Protein Binding (PPB):	88.006%	Volume Distribution (VD):	-0.062
Fu:	7.525% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.937	BCRP inhibitor:	0.003
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.644
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.048
HLM stability:	0.062 ? 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):

0.801

Half-life (T1/2):

3.435

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.459
Human Hepatotoxicity (H-HT):	0.447	Drug-induced Liver Injury (DILI):	0.892
AMES Toxicity:	0.171	Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.409	Skin Sensitization:	0.916
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.162	Ototoxicity:	1.0
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.096
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.332
A549 Cytotoxicity:	0.214	Hek293 Cytotoxicity:	0.616
BCF:	0.435 ? 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:	3.422 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.469 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.374 ? 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
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	Roots	Mexican	n.a.	PMID[10479311]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	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
MIC	4
IC50	1
ED50	1

Activity Type	# Activity
Cell line	2
Organism	4

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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[9548875]
NPT91	Cell line	KB	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[29126728]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[21623630]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	DrugMatrix in vitro pharmacology data
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[20439609]

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 NPC476066 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	21963
0.1-0.2	25102
0.2-0.3	2605
0.3-0.4	61
0.4-0.5	34
0.5-0.6	55
0.6-0.7	18
0.7-0.8	0
0.8-0.85	6
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC475525
0.963	High Similarity	NPC475540
0.9286	High Similarity	NPC473605
0.9286	High Similarity	NPC475375
0.9167	High Similarity	NPC475164
0.8902	High Similarity	NPC478730
0.8471	Intermediate Similarity	NPC478732
0.8372	Intermediate Similarity	NPC475270
0.8372	Intermediate Similarity	NPC475327
0.8353	Intermediate Similarity	NPC476087
0.8353	Intermediate Similarity	NPC475667
0.8256	Intermediate Similarity	NPC478731
0.7528	Intermediate Similarity	NPC238264
0.7528	Intermediate Similarity	NPC477345
0.7447	Intermediate Similarity	NPC475241
0.7416	Intermediate Similarity	NPC186992
0.7303	Intermediate Similarity	NPC173328
0.7111	Intermediate Similarity	NPC297768
0.6786	Remote Similarity	NPC606819
0.6703	Remote Similarity	NPC478733
0.6667	Remote Similarity	NPC478734
0.663	Remote Similarity	NPC60849
0.6559	Remote Similarity	NPC479058
0.6413	Remote Similarity	NPC477344
0.6277	Remote Similarity	NPC479061
0.6264	Remote Similarity	NPC477349
0.6263	Remote Similarity	NPC478728
0.6237	Remote Similarity	NPC158302
0.6211	Remote Similarity	NPC479060
0.6186	Remote Similarity	NPC115013
0.6146	Remote Similarity	NPC119583
0.6105	Remote Similarity	NPC267592
0.6064	Remote Similarity	NPC479059
0.6042	Remote Similarity	NPC477319
0.602	Remote Similarity	NPC290012
0.6	Remote Similarity	NPC269318
0.5979	Remote Similarity	NPC143421
0.596	Remote Similarity	NPC224953
0.5918	Remote Similarity	NPC483170
0.5914	Remote Similarity	NPC113745
0.5914	Remote Similarity	NPC477320
0.5914	Remote Similarity	NPC477323
0.5914	Remote Similarity	NPC477325
0.5914	Remote Similarity	NPC609436
0.587	Remote Similarity	NPC281563
0.5833	Remote Similarity	NPC109887
0.5816	Remote Similarity	NPC307400
0.5816	Remote Similarity	NPC27289
0.5814	Remote Similarity	NPC479056
0.58	Remote Similarity	NPC479057
0.58	Remote Similarity	NPC126685
0.5789	Remote Similarity	NPC89843
0.5745	Remote Similarity	NPC22742
0.5745	Remote Similarity	NPC477346
0.5729	Remote Similarity	NPC477326
0.5714	Remote Similarity	NPC44682
0.57	Remote Similarity	NPC238056
0.5686	Remote Similarity	NPC44782
0.5644	Remote Similarity	NPC183888
0.5644	Remote Similarity	NPC184915
0.5588	Remote Similarity	NPC163409
0.5588	Remote Similarity	NPC123204
0.5577	Remote Similarity	NPC478727
0.5567	Remote Similarity	NPC600446
0.5567	Remote Similarity	NPC605013
0.5543	Remote Similarity	NPC477350
0.5484	Remote Similarity	NPC146380
0.5446	Remote Similarity	NPC610996
0.5392	Remote Similarity	NPC169345
0.5392	Remote Similarity	NPC477317
0.5392	Remote Similarity	NPC477318
0.5351	Remote Similarity	NPC600721
0.5351	Remote Similarity	NPC605872
0.5347	Remote Similarity	NPC472204
0.5347	Remote Similarity	NPC294748
0.534	Remote Similarity	NPC259294
0.5306	Remote Similarity	NPC477332
0.53	Remote Similarity	NPC146992
0.53	Remote Similarity	NPC85759
0.53	Remote Similarity	NPC478725
0.5248	Remote Similarity	NPC478723
0.5248	Remote Similarity	NPC478724
0.5234	Remote Similarity	NPC477348
0.5221	Remote Similarity	NPC611287
0.5214	Remote Similarity	NPC472352
0.5204	Remote Similarity	NPC604005
0.5204	Remote Similarity	NPC605014
0.5158	Remote Similarity	NPC475425
0.5149	Remote Similarity	NPC478722
0.5146	Remote Similarity	NPC478726
0.5143	Remote Similarity	NPC472200

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7236
0.1-0.2	1863
0.2-0.3	51
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