NPASS Compound

Natural Product: NPC475436

Natural Product ID	NPC475436
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XASDQEOMZDFLDT-QGYWBVHWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505676
PubChem CID	44559499
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 115122 0 0 0 0 0 0 0 0999 V2000 7.1933 2.2376 -5.9869 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8537 1.4686 -4.7282 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9386 0.2874 -5.0101 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7443 -0.4035 -3.6772 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0814 0.5389 -2.7391 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4580 0.2412 -1.2702 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2012 0.2553 -0.6209 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2876 0.9335 -1.6664 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6882 0.2323 -2.7752 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0005 0.5835 -1.0469 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2811 0.9972 0.4143 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7847 0.9606 0.5771 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2788 0.2201 1.7851 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3080 0.4374 2.9380 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1207 -0.3680 2.5290 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4570 0.2433 1.3517 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6556 -0.8952 0.7207 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3596 -1.4412 1.7127 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1609 -1.6520 3.0782 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1099 -0.6101 3.5987 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7818 -1.1736 4.8154 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9631 -2.0402 5.6823 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4961 -2.0901 5.4612 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9487 -1.8204 4.0629 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9434 -3.3715 5.8250 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4622 0.6831 3.9768 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5519 -0.7217 1.6336 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5994 -1.4549 1.0662 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0803 -0.8259 -0.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5068 -1.1492 -0.5358 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8858 -2.4766 0.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4487 -2.6833 1.4429 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6831 -1.6096 1.9153 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6593 -2.8021 2.3301 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2860 -3.5016 -0.7368 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3091 -0.1690 0.0693 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0398 0.5445 -0.8369 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5339 0.3727 -0.7625 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0537 0.7997 -2.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4592 2.0960 -2.5954 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0371 2.3195 -2.1801 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7575 1.8997 -0.8785 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0602 1.6819 -3.1684 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4992 2.1714 -3.9878 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8774 -0.2372 -3.0619 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1449 1.2173 0.1516 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0295 0.5745 0.0189 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3493 2.3757 0.7346 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6017 1.0680 -0.8165 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1642 1.8656 -3.0240 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2539 2.3415 -3.6749 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3583 3.3203 -5.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1537 1.8910 -6.4449 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4148 2.0877 -6.7671 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8284 1.0146 -4.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0122 0.6785 -5.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4334 -0.3579 -5.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7578 -0.6815 -3.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1013 -1.2963 -3.8252 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8662 -0.8166 -1.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7633 -0.7866 -0.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5159 1.9832 -1.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8400 -0.5098 -1.1281 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1542 1.1728 -1.4701 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9881 2.0848 0.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2457 0.6167 2.1200 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3221 -0.8741 1.5675 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0728 1.5021 3.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8008 0.0582 3.8571 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 -1.3856 2.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6402 0.9143 1.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0614 -0.5471 -0.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3606 -1.6970 0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6040 -2.4613 1.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7427 -2.6205 3.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6763 -1.7519 4.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2546 -0.3083 5.3663 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3949 -3.0847 5.7152 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1155 -1.6883 6.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0740 -1.3987 6.1444 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5957 -0.9088 4.0107 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6124 -2.6403 3.6813 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6372 -3.6764 5.1908 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3938 0.7940 5.0922 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5456 0.7693 3.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1205 1.5411 3.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1997 -2.4769 0.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3931 -1.0763 -1.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6807 -1.1392 -1.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9845 -2.6258 -0.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8353 -3.6045 1.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5879 -3.0129 1.7357 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5527 -3.6138 3.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8857 -1.8767 2.9003 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8057 -3.5959 -1.5776 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7572 0.1317 -1.8544 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8408 -0.6753 -0.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1435 0.9484 -2.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0579 2.9220 -2.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8415 3.4190 -2.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6966 2.4402 -3.9004 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1474 1.3226 -2.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5125 0.8823 -3.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0827 2.9337 -4.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7181 -0.7668 -3.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4404 1.7698 0.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6897 0.7209 0.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3051 2.3944 1.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2877 2.9585 -0.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6222 2.8727 1.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4463 2.1415 -0.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9911 0.6513 0.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4383 0.8790 -1.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9071 3.2746 -4.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0891 2.7133 -3.0465 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 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 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 20 26 1 0 18 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 31 35 1 0 30 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 40 44 1 0 39 45 1 0 38 46 1 0 29 47 1 0 12 48 1 0 6 49 1 0 5 50 1 0 50 51 1 0 51 2 1 0 9 5 1 0 12 7 1 0 16 11 1 0 20 15 1 0 24 19 1 0 33 28 1 0 42 37 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 0 3 56 1 0 3 57 1 0 4 58 1 0 4 59 1 0 6 60 1 0 7 61 1 0 8 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 13 66 1 0 13 67 1 0 14 68 1 0 14 69 1 0 15 70 1 0 16 71 1 0 17 72 1 0 17 73 1 0 18 74 1 0 19 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 25 83 1 0 26 84 1 0 26 85 1 0 26 86 1 0 28 87 1 0 29 88 1 0 30 89 1 0 31 90 1 0 32 91 1 0 34 92 1 0 34 93 1 0 34 94 1 0 35 95 1 0 37 96 1 0 38 97 1 0 39 98 1 0 40 99 1 0 41100 1 0 43101 1 0 43102 1 0 43103 1 0 44104 1 0 45105 1 0 46106 1 0 47107 1 0 48108 1 0 48109 1 0 48110 1 0 49111 1 0 49112 1 0 49113 1 0 51114 1 0 51115 1 0 M END

Standard InCHIKey	XASDQEOMZDFLDT-QGYWBVHWSA-N
Standard InCHI	InChI=1S/C39H64O12/c1-17-7-12-39(46-16-17)18(2)28-27(51-39)15-24-22-14-26(25-13-21(40)8-10-37(25,5)23(22)9-11-38(24,28)6)49-36-33(45)34(30(42)20(4)48-36)50-35-32(44)31(43)29(41)19(3)47-35/h17-36,40-45H,7-16H2,1-6H3/t17-,18+,19-,20-,21+,22-,23+,24+,25-,26+,27+,28+,29-,30-,31+,32+,33-,34+,35+,36+,37-,38+,39-/m1/s1
SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC(C6C5(CCC(C6)O)C)OC7C(C(C(C(O7)C)O)OC8C(C(C(C(O8)C)O)O)O)O)C)C)OC1

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4703	Solanum hispidum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15217270]
NPO4703	Solanum hispidum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4703	Solanum hispidum	Species	Solanaceae	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

Activity Type	# Activity
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
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	400.0	ug.mL-1	PMID[25176189]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	200.0	ug.mL-1	PMID[18303847]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	50.0	ug.mL-1	PMID[22840694]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	200.0	ug.mL-1	DOI[10.6019/CHEMBL1201861]

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 NPC475436 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	28408
0.1-0.2	19329
0.2-0.3	1793
0.3-0.4	166
0.4-0.5	88
0.5-0.6	46
0.6-0.7	9
0.7-0.8	0
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC131693
0.88	High Similarity	NPC144790
0.88	High Similarity	NPC149400
0.8537	High Similarity	NPC312678
0.8537	High Similarity	NPC253268
0.8072	Intermediate Similarity	NPC179859
0.8072	Intermediate Similarity	NPC473851
0.775	Intermediate Similarity	NPC277715
0.7419	Intermediate Similarity	NPC485603
0.7241	Intermediate Similarity	NPC485591
0.7195	Intermediate Similarity	NPC88962
0.7	Intermediate Similarity	NPC291547
0.7	Intermediate Similarity	NPC485593
0.7	Intermediate Similarity	NPC174024
0.6848	Remote Similarity	NPC485590
0.6705	Remote Similarity	NPC485594
0.6327	Remote Similarity	NPC485605
0.6224	Remote Similarity	NPC14704
0.618	Remote Similarity	NPC473774
0.618	Remote Similarity	NPC481419
0.618	Remote Similarity	NPC481417
0.6129	Remote Similarity	NPC234352
0.6019	Remote Similarity	NPC485604
0.59	Remote Similarity	NPC485599
0.5824	Remote Similarity	NPC481420
0.5824	Remote Similarity	NPC481421
0.5802	Remote Similarity	NPC296734
0.5679	Remote Similarity	NPC248944
0.5679	Remote Similarity	NPC7479
0.5679	Remote Similarity	NPC257296
0.5631	Remote Similarity	NPC485596
0.5567	Remote Similarity	NPC477451
0.5556	Remote Similarity	NPC306131
0.5556	Remote Similarity	NPC200802
0.5545	Remote Similarity	NPC480554
0.5545	Remote Similarity	NPC485595
0.5534	Remote Similarity	NPC485597
0.551	Remote Similarity	NPC222731
0.5446	Remote Similarity	NPC480553
0.5429	Remote Similarity	NPC485598
0.5426	Remote Similarity	NPC24960
0.54	Remote Similarity	NPC19400
0.534	Remote Similarity	NPC70204
0.5288	Remote Similarity	NPC113044
0.5288	Remote Similarity	NPC283829
0.5288	Remote Similarity	NPC161676
0.5258	Remote Similarity	NPC481424
0.5258	Remote Similarity	NPC481422
0.5243	Remote Similarity	NPC470432
0.5243	Remote Similarity	NPC230507
0.5243	Remote Similarity	NPC6295
0.5229	Remote Similarity	NPC184617
0.5214	Remote Similarity	NPC480556
0.5204	Remote Similarity	NPC297348
0.5204	Remote Similarity	NPC249204
0.5204	Remote Similarity	NPC48339
0.5204	Remote Similarity	NPC177834
0.5204	Remote Similarity	NPC141769
0.5204	Remote Similarity	NPC477547
0.5192	Remote Similarity	NPC195297
0.5152	Remote Similarity	NPC294686
0.514	Remote Similarity	NPC470433
0.514	Remote Similarity	NPC46190
0.514	Remote Similarity	NPC171073
0.514	Remote Similarity	NPC602423
0.5102	Remote Similarity	NPC181845
0.5051	Remote Similarity	NPC325828
0.5048	Remote Similarity	NPC141433
0.5046	Remote Similarity	NPC300557

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7856
0.1-0.2	1237
0.2-0.3	51
0.3-0.4	3
0.4-0.5	1
0.5-0.6	2
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
0.5679	Remote Similarity	NPD6928	Phase 2
0.5051	Remote Similarity	NPD8171	Phase 2

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