NPASS Compound

Natural Product: NPC37193

Natural Product ID	NPC37193
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GRCYPVCUUUYXBK-UWDRNDSISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 103109 0 0 0 0 0 0 0 0999 V2000 4.5986 -1.8124 1.1648 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1475 -0.4313 0.7647 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2103 0.2972 -0.0369 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7649 1.7327 -0.1631 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3758 1.7613 -0.7151 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4438 0.7864 -0.0142 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9829 -0.4764 -0.0219 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2131 0.8911 -0.6349 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2349 1.4174 0.2371 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4584 2.6022 -0.3833 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9545 2.5308 -0.2926 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5124 1.3160 -1.0200 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7630 1.6958 -2.4641 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7893 0.9386 -0.3045 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8932 1.9228 -0.6205 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0751 1.5630 0.2152 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6122 0.1634 -0.0663 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3593 0.2202 -1.3881 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4562 -0.2902 1.0799 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6630 -1.3223 1.8712 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2836 -1.3275 1.2647 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5298 -0.8527 -0.1538 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2514 -0.3989 -0.7720 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1753 -1.4297 -0.4233 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9898 -1.1312 -1.2815 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 0.2401 -0.9851 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7970 0.3157 0.3797 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5221 0.5475 -1.9734 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9896 -1.9261 -0.9378 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7502 -0.9089 0.7161 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9081 -0.3812 1.0943 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0123 -1.1878 0.6042 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2588 -0.9689 0.7839 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4564 -2.2208 -0.0829 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0710 -2.1277 -0.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3090 1.5271 -2.0714 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5763 2.4770 -1.0172 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4626 0.1721 0.5112 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3180 -0.4696 -0.3576 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4843 0.4036 -0.7695 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3927 0.7015 0.4064 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2129 -0.3785 1.4801 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0016 -1.6693 0.7113 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1166 -2.8051 1.7122 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8733 -4.0207 1.0983 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7308 -1.6701 0.1917 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3039 -0.4388 2.3343 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2228 1.9661 0.9150 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1803 -0.1795 -1.8205 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7680 -2.3266 1.6559 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0554 -2.3622 0.3252 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3964 -1.6829 1.9293 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9472 0.1591 1.6812 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1929 -0.1506 -1.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7521 2.2511 0.8220 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9516 2.7922 -0.5399 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3996 1.1445 1.0562 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6523 1.6324 1.2246 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1420 3.4966 0.1978 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1765 2.7925 -1.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2924 2.5578 0.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3626 3.4242 -0.7933 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7640 1.9974 -2.8764 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4079 2.5775 -2.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1357 0.8150 -3.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5863 0.9998 0.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6061 2.9597 -0.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1619 1.8451 -1.6885 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8633 1.6528 1.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9049 2.2709 -0.0045 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0587 -0.6510 -1.9876 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4526 0.2208 -1.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0383 1.1313 -1.9718 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6284 0.5398 1.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0867 -2.3505 1.7057 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6720 -1.1550 2.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6549 -0.6367 1.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8449 -2.3412 1.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3681 -0.3546 -1.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5679 -2.4178 -0.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9737 -1.2898 0.6584 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1551 -1.8433 -1.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3058 -1.1683 -2.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5356 0.6622 1.1527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3681 -0.6375 0.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5914 -0.0566 -2.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6018 -2.7848 -0.6096 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0750 0.5297 1.6910 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6424 -3.0385 0.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6882 -2.1334 -1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0829 0.5774 -2.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6383 1.9915 -1.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7585 -0.7161 -1.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0884 1.3697 -1.1330 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4358 0.6002 0.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2804 -0.1997 2.0516 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7949 -1.8316 -0.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1608 -2.7814 2.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4222 -2.6651 2.5426 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2997 -4.6262 1.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0898 0.0884 3.1673 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7839 2.6494 0.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6238 -0.8918 -2.2282 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 6 22 29 1 6 19 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 5 36 1 0 4 37 1 0 3 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 7 2 1 0 27 9 1 0 35 30 1 0 46 39 1 0 26 12 1 0 23 14 1 0 22 17 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 1 3 54 1 6 4 55 1 1 5 56 1 6 6 57 1 1 9 58 1 1 10 59 1 0 10 60 1 0 11 61 1 0 11 62 1 0 13 63 1 0 13 64 1 0 13 65 1 0 14 66 1 1 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 18 71 1 0 18 72 1 0 18 73 1 0 19 74 1 1 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 23 79 1 6 24 80 1 0 24 81 1 0 25 82 1 0 25 83 1 0 27 84 1 0 27 85 1 0 28 86 1 0 29 87 1 0 31 88 1 0 35 89 1 0 35 90 1 0 36 91 1 0 37 92 1 0 39 93 1 6 40 94 1 6 41 95 1 6 42 96 1 1 43 97 1 6 44 98 1 0 44 99 1 0 45100 1 0 47101 1 0 48102 1 0 49103 1 0 M END

Standard InCHIKey	GRCYPVCUUUYXBK-UWDRNDSISA-N
Standard InCHI	InChI=1S/C35H54O14/c1-16-29(49-31-27(41)25(39)24(38)22(14-36)48-31)26(40)28(42)30(46-16)47-18-4-8-32(2)20-5-9-33(3)19(17-12-23(37)45-15-17)7-11-35(33,44)21(20)6-10-34(32,43)13-18/h12,16,18-22,24-31,36,38-44H,4-11,13-15H2,1-3H3/t16-,18-,19+,20-,21+,22+,24+,25-,26-,27+,28+,29-,30+,31-,32+,33+,34-,35-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)C1=CC(=O)OC1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

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
NPO17901	Ipomoea squamosa	Species	Convolvulaceae	Eukaryota	leaves	Suriname rainforest	n.a.	PMID[15844934]
NPO19836	Symphytum caucasicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12165	Comanthosphace japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17901	Ipomoea squamosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19836	Symphytum caucasicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12467	Cephalanthus occidentalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12467	Cephalanthus occidentalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19836	Symphytum caucasicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18535	Psoralea drupacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12165	Comanthosphace japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18535	Psoralea drupacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12467	Cephalanthus occidentalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19836	Symphytum caucasicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17901	Ipomoea squamosa	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

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 NPC37193 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	16426
0.1-0.2	27978
0.2-0.3	4465
0.3-0.4	792
0.4-0.5	63
0.5-0.6	64
0.6-0.7	50
0.7-0.8	0
0.8-0.85	1
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC84987
0.878	High Similarity	NPC32793
0.878	High Similarity	NPC116075
0.8554	High Similarity	NPC475556
0.8554	High Similarity	NPC311706
0.8452	Intermediate Similarity	NPC475629
0.7875	Intermediate Similarity	NPC99728
0.7875	Intermediate Similarity	NPC87250
0.7875	Intermediate Similarity	NPC244402
0.7875	Intermediate Similarity	NPC50305
0.7816	Intermediate Similarity	NPC264336
0.7791	Intermediate Similarity	NPC236973
0.7791	Intermediate Similarity	NPC32177
0.7791	Intermediate Similarity	NPC469756
0.7791	Intermediate Similarity	NPC275901
0.7727	Intermediate Similarity	NPC59288
0.7701	Intermediate Similarity	NPC188234
0.7317	Intermediate Similarity	NPC158344
0.7059	Intermediate Similarity	NPC157376
0.7059	Intermediate Similarity	NPC142066
0.7059	Intermediate Similarity	NPC603972
0.6882	Remote Similarity	NPC469749
0.686	Remote Similarity	NPC5311
0.686	Remote Similarity	NPC77299
0.686	Remote Similarity	NPC17896
0.686	Remote Similarity	NPC469755
0.686	Remote Similarity	NPC284406
0.686	Remote Similarity	NPC480906
0.686	Remote Similarity	NPC197707
0.686	Remote Similarity	NPC251866
0.6809	Remote Similarity	NPC146857
0.6782	Remote Similarity	NPC480914
0.6706	Remote Similarity	NPC474418
0.6667	Remote Similarity	NPC480907
0.6667	Remote Similarity	NPC329675
0.6632	Remote Similarity	NPC247190
0.6596	Remote Similarity	NPC486143
0.6596	Remote Similarity	NPC125077
0.6596	Remote Similarity	NPC486135
0.6596	Remote Similarity	NPC486142
0.6596	Remote Similarity	NPC486137
0.6596	Remote Similarity	NPC486149
0.6526	Remote Similarity	NPC232785
0.6526	Remote Similarity	NPC486139
0.6517	Remote Similarity	NPC77319
0.6517	Remote Similarity	NPC471351
0.6517	Remote Similarity	NPC471355
0.6404	Remote Similarity	NPC243196
0.6364	Remote Similarity	NPC219085
0.6344	Remote Similarity	NPC30483
0.6344	Remote Similarity	NPC470897
0.6337	Remote Similarity	NPC194716
0.6292	Remote Similarity	NPC34390
0.6238	Remote Similarity	NPC120390
0.6222	Remote Similarity	NPC76572
0.6222	Remote Similarity	NPC193382
0.6211	Remote Similarity	NPC480910
0.6211	Remote Similarity	NPC240070
0.6211	Remote Similarity	NPC480909
0.6211	Remote Similarity	NPC486130
0.6211	Remote Similarity	NPC608063
0.62	Remote Similarity	NPC486144
0.62	Remote Similarity	NPC486145
0.62	Remote Similarity	NPC486147
0.62	Remote Similarity	NPC475590
0.62	Remote Similarity	NPC486136
0.62	Remote Similarity	NPC486148
0.6154	Remote Similarity	NPC146456
0.6146	Remote Similarity	NPC486127
0.6105	Remote Similarity	NPC292467
0.6067	Remote Similarity	NPC99620
0.596	Remote Similarity	NPC329986
0.596	Remote Similarity	NPC140092
0.596	Remote Similarity	NPC486146
0.5938	Remote Similarity	NPC40749
0.5934	Remote Similarity	NPC469750
0.5922	Remote Similarity	NPC74259
0.59	Remote Similarity	NPC486138
0.59	Remote Similarity	NPC276838
0.5851	Remote Similarity	NPC471354
0.5851	Remote Similarity	NPC27507
0.5842	Remote Similarity	NPC486132
0.5842	Remote Similarity	NPC486131
0.5824	Remote Similarity	NPC309034
0.5816	Remote Similarity	NPC610296
0.5784	Remote Similarity	NPC486128
0.5758	Remote Similarity	NPC208193
0.5745	Remote Similarity	NPC9499
0.5745	Remote Similarity	NPC471360
0.5745	Remote Similarity	NPC469751
0.5745	Remote Similarity	NPC471361
0.5745	Remote Similarity	NPC86159
0.5745	Remote Similarity	NPC469752
0.5745	Remote Similarity	NPC469754
0.5745	Remote Similarity	NPC70542
0.5714	Remote Similarity	NPC486140
0.5701	Remote Similarity	NPC474423
0.5619	Remote Similarity	NPC475419
0.5591	Remote Similarity	NPC6108
0.5591	Remote Similarity	NPC89514
0.5566	Remote Similarity	NPC474908
0.5566	Remote Similarity	NPC486134
0.5566	Remote Similarity	NPC486141
0.5532	Remote Similarity	NPC10823
0.5514	Remote Similarity	NPC486133
0.5514	Remote Similarity	NPC486150
0.55	Remote Similarity	NPC231518
0.55	Remote Similarity	NPC488944
0.5484	Remote Similarity	NPC196429
0.5474	Remote Similarity	NPC180079
0.5474	Remote Similarity	NPC83287
0.5422	Remote Similarity	NPC97487
0.5405	Remote Similarity	NPC486152
0.5385	Remote Similarity	NPC475219
0.5333	Remote Similarity	NPC488943
0.5333	Remote Similarity	NPC488942
0.5306	Remote Similarity	NPC72260
0.5283	Remote Similarity	NPC329636
0.5263	Remote Similarity	NPC480915
0.5258	Remote Similarity	NPC471353
0.5238	Remote Similarity	NPC476221
0.5238	Remote Similarity	NPC477709
0.5233	Remote Similarity	NPC72772
0.5229	Remote Similarity	NPC329784
0.5189	Remote Similarity	NPC479360
0.5189	Remote Similarity	NPC479359
0.5149	Remote Similarity	NPC27363
0.5138	Remote Similarity	NPC117445
0.5138	Remote Similarity	NPC308262
0.5116	Remote Similarity	NPC10232
0.5102	Remote Similarity	NPC471359
0.5102	Remote Similarity	NPC305574
0.5053	Remote Similarity	NPC471633
0.5045	Remote Similarity	NPC488945
0.5045	Remote Similarity	NPC488946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC37193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6307
0.1-0.2	2737
0.2-0.3	81
0.3-0.4	12
0.4-0.5	8
0.5-0.6	4
0.6-0.7	1
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
0.686	Remote Similarity	NPD7319	Approved
0.55	Remote Similarity	NPD8033	Approved
0.5474	Remote Similarity	NPD7327	Approved
0.5474	Remote Similarity	NPD7328	Phase 4
0.5306	Remote Similarity	NPD8294	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