NPASS Compound

Natural Product: NPC43589

Natural Product ID	NPC43589
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Porsapogenin 9
IUPAC Name	[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6S)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-[(2E,6S)-2,6-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyocta-2,7-dienoyl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	Porsapogenin 9
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506883
PubChem CID	44566622
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

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0 0 0 0 0 0 0 0 0 0 12.0332 -4.2229 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.3354 -2.9329 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6186 -1.1952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.5730 -1.7162 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.8179 0.3589 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.8458 -5.7092 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3607 -6.7551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0372 -4.8613 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2997 -7.4356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8354 -7.8157 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.6544 -4.8613 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5634 -0.8086 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.0664 0.9512 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8478 3.8161 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9169 3.6096 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0529 3.0999 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7507 5.3912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.8729 1.7894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7741 3.9252 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 19.2291 3.5959 0.0000 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 2 0 9 7 1 1 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 19 31 1 0 31 32 2 0 19 33 1 0 15 34 1 0 11 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 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 45 46 1 0 43 47 1 6 42 48 1 1 42 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 1 52 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 57 59 1 0 56 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 68 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 78 81 1 0 77 82 1 0 71 83 1 0 70 84 1 0 63 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 86 89 1 0 85 90 1 0 35 91 1 0 35 92 1 0 5 93 1 0 93 94 1 0 94 95 1 0 95 96 1 0 94 97 1 0 93 98 1 0 98 99 1 0 99100 1 0 100101 1 0 101102 1 0 101103 1 0 103104 1 0 104105 1 0 105106 1 0 104107 1 0 107108 1 0 108109 1 0 109110 1 0 110111 1 0 111112 1 0 110113 1 0 113114 1 0 114115 1 0 115116 1 0 114117 1 0 113118 1 0 103119 1 0 119120 1 0 120121 1 0 121122 1 0 122123 1 0 123124 1 0 124125 1 0 123126 1 0 122127 1 0 127128 1 0 95 3 1 0 105 99 1 0 115108 1 0 124120 1 0 45 9 1 0 57 51 1 0 87 61 1 0 37 9 1 0 43 38 1 0 72 66 1 0 79 74 1 0 27 21 1 0 52 41 1 0 1129 1 0 2130 1 0 2131 1 0 3132 1 6 5133 1 6 10134 1 0 10135 1 0 11136 1 6 16137 1 0 17138 1 0 17139 1 0 18140 1 0 18141 1 0 21142 1 6 23143 1 6 24144 1 0 24145 1 0 24146 1 0 25147 1 1 26148 1 6 27149 1 1 28150 1 0 29151 1 0 30152 1 0 31153 1 0 32154 1 0 32155 1 0 33156 1 0 33157 1 0 33158 1 0 34159 1 0 34160 1 0 34161 1 0 36162 1 0 36163 1 0 37164 1 1 39165 1 0 40166 1 0 40167 1 0 41168 1 6 44169 1 0 44170 1 0 45171 1 1 46172 1 0 47173 1 0 47174 1 0 47175 1 0 48176 1 0 48177 1 0 48178 1 0 49179 1 0 49180 1 0 50181 1 0 50182 1 0 51183 1 6 53184 1 0 53185 1 0 53186 1 0 54187 1 0 54188 1 0 55189 1 0 55190 1 0 56191 1 6 58192 1 0 58193 1 0 58194 1 0 59195 1 0 59196 1 0 59197 1 0 61198 1 6 63199 1 6 64200 1 0 64201 1 0 66202 1 1 68203 1 1 69204 1 0 69205 1 0 69206 1 0 70207 1 1 71208 1 1 72209 1 6 74210 1 1 76211 1 0 76212 1 0 77213 1 6 78214 1 1 79215 1 6 80216 1 0 81217 1 0 82218 1 0 83219 1 0 84220 1 0 85221 1 1 86222 1 6 87223 1 1 88224 1 0 89225 1 0 90226 1 0 91227 1 0 91228 1 0 91229 1 0 92230 1 0 92231 1 0 92232 1 0 93233 1 1 94234 1 6 95235 1 1 96236 1 0 97237 1 0 99238 1 1 101239 1 6 102240 1 0 102241 1 0 102242 1 0 103243 1 1 104244 1 6 105245 1 6 106246 1 0 108247 1 1 110248 1 1 111249 1 0 111250 1 0 112251 1 0 113252 1 6 114253 1 1 115254 1 6 116255 1 0 117256 1 0 118257 1 0 120258 1 6 122259 1 1 123260 1 6 124261 1 1 125262 1 0 126263 1 0 127264 1 0 127265 1 0 128266 1 0 M END

Standard InCHIKey	CDUBMGLWDMHRDS-AHQAUBLKSA-N
Standard InCHI	InChI=1S/C86H138O42/c1-14-82(10,128-76-64(108)55(99)48(92)33(3)114-76)21-15-16-32(2)70(110)121-47-26-86(79(111)127-78-69(59(103)52(96)40(28-88)119-78)126-75-65(109)67(124-74-63(107)56(100)51(95)39(27-87)117-74)66(35(5)116-75)123-73-61(105)53(97)41(29-89)118-73)37(24-80(47,6)7)36-17-18-44-83(11)22-20-46(81(8,9)43(83)19-23-84(44,12)85(36,13)25-45(86)91)122-72-62(106)57(101)54(98)42(120-72)31-113-77-68(58(102)49(93)34(4)115-77)125-71-60(104)50(94)38(90)30-112-71/h14,16-17,33-35,37-69,71-78,87-109H,1,15,18-31H2,2-13H3/b32-16+/t33-,34-,35+,37+,38-,39-,40-,41+,42-,43+,44-,45-,46+,47+,48-,49+,50+,51-,52-,53+,54-,55+,56+,57+,58+,59+,60-,61-,62-,63-,64-,65-,66+,67+,68-,69-,71+,72+,73+,74+,75+,76+,77-,78+,82-,83+,84-,85-,86-/m1/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@@]23C[C@H](OC(=O)/C(=C/CC[C@](O[C@@H]4O[C@H](C)[C@H]([C@@H]([C@H]4O)O)O)(C=C)C)/C)C(C[C@H]3C3=CC[C@H]4[C@@]([C@@]3(C[C@H]2O)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](C)[C@@H]([C@@H]([C@H]3O[C@@H]3OC[C@H]([C@@H]([C@H]3O)O)O)O)O)[C@H]([C@@H]([C@H]2O)O)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O[C@@H]1O[C@H]([C@@H]([C@H]1O)O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1842.87	Volume:	1740.784 ? Van der Waals volume.
Dense:	1.059	LogP:	0.367 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.184 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.534 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	28.0	Rigid Bonds:	77.0
TPSA:	656.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	42.0
H-Bond Donor:	23.0	Rings:	13.0
Heavy Atoms:	42.0

MedChem Properties

QED Drug-Likeness Score:	0.017	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	8.221	Fsp³:	0.907
MCE-18:	293.707 ? 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:	0.695	Fluc inhibitor:	0.313 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.457	Promiscuous compounds:	0.222

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.465	MDCK Permeability:	-4.538
Pgp-inhibitor:	0.0	Pgp-substrate:	0.556
PAMPA:	1.0 ? 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):	0.993
20% Bioavailability (F20%):	0.812	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	53.792%	Volume Distribution (VD):	-0.234
Fu:	21.691% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.946
HLM stability:	0.002 ? 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):

-1.918

Half-life (T1/2):

5.996

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.548	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.999	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.759	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.087	RPMI-8226 Immunitoxicity:	0.742
A549 Cytotoxicity:	0.995	Hek293 Cytotoxicity:	0.495
BCF:	0.628 ? 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:	3.558 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.581 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.25 ? 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
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12181	Albizia julibrissin	Species	Fabaceae	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	1

Activity Type	# Activity
Cell line	1

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
NPT91	Cell line	KB	Homo sapiens	IC50	=	1600.0	nM	PMID[19371071]

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 NPC43589 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	25553
0.1-0.2	20969
0.2-0.3	2250
0.3-0.4	637
0.4-0.5	339
0.5-0.6	65
0.6-0.7	10
0.7-0.8	0
0.8-0.85	8
0.85-0.9	6
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC311178
0.947	High Similarity	NPC300655
0.9394	High Similarity	NPC233223
0.9394	High Similarity	NPC183816
0.9318	High Similarity	NPC484829
0.9191	High Similarity	NPC222951
0.9143	High Similarity	NPC324933
0.8897	High Similarity	NPC196874
0.8889	High Similarity	NPC45606
0.8681	High Similarity	NPC319719
0.8621	High Similarity	NPC265699
0.8613	High Similarity	NPC329878
0.8542	High Similarity	NPC322904
0.8417	Intermediate Similarity	NPC220838
0.8345	Intermediate Similarity	NPC100612
0.8333	Intermediate Similarity	NPC329893
0.831	Intermediate Similarity	NPC478559
0.831	Intermediate Similarity	NPC478560
0.8129	Intermediate Similarity	NPC484830
0.8082	Intermediate Similarity	NPC113620
0.8	Intermediate Similarity	NPC484831
0.7885	Intermediate Similarity	NPC187497
0.7829	Intermediate Similarity	NPC488204
0.7628	Intermediate Similarity	NPC174336
0.7584	Intermediate Similarity	NPC475444
0.7584	Intermediate Similarity	NPC473679
0.7436	Intermediate Similarity	NPC488201
0.7419	Intermediate Similarity	NPC488203
0.7172	Intermediate Similarity	NPC475177
0.7133	Intermediate Similarity	NPC13989
0.7044	Intermediate Similarity	NPC488202
0.6768	Remote Similarity	NPC488513
0.6692	Remote Similarity	NPC105800
0.6687	Remote Similarity	NPC488620
0.6642	Remote Similarity	NPC207738
0.6626	Remote Similarity	NPC488200
0.6569	Remote Similarity	NPC123522
0.625	Remote Similarity	NPC286457
0.6119	Remote Similarity	NPC232237
0.6096	Remote Similarity	NPC470876
0.6012	Remote Similarity	NPC488618
0.5976	Remote Similarity	NPC488619
0.5973	Remote Similarity	NPC309223
0.5962	Remote Similarity	NPC489208
0.5921	Remote Similarity	NPC102505
0.5921	Remote Similarity	NPC488514
0.5909	Remote Similarity	NPC33012
0.5882	Remote Similarity	NPC489209
0.5844	Remote Similarity	NPC8524
0.5816	Remote Similarity	NPC104137
0.5816	Remote Similarity	NPC26626
0.5811	Remote Similarity	NPC473452
0.5734	Remote Similarity	NPC172365
0.5686	Remote Similarity	NPC220160
0.5655	Remote Similarity	NPC482013
0.5652	Remote Similarity	NPC164389
0.5588	Remote Similarity	NPC472270
0.5588	Remote Similarity	NPC112492
0.557	Remote Similarity	NPC85154
0.5563	Remote Similarity	NPC481079
0.5519	Remote Similarity	NPC70809
0.5497	Remote Similarity	NPC13998
0.5473	Remote Similarity	NPC603137
0.5412	Remote Similarity	NPC23020
0.5352	Remote Similarity	NPC488517
0.5319	Remote Similarity	NPC488526
0.5319	Remote Similarity	NPC148603
0.5287	Remote Similarity	NPC224381
0.528	Remote Similarity	NPC480421
0.527	Remote Similarity	NPC610204
0.526	Remote Similarity	NPC475514
0.5253	Remote Similarity	NPC250247
0.525	Remote Similarity	NPC480422
0.5238	Remote Similarity	NPC210729
0.5238	Remote Similarity	NPC82931
0.5229	Remote Similarity	NPC21691
0.5226	Remote Similarity	NPC484059
0.5226	Remote Similarity	NPC484060
0.5221	Remote Similarity	NPC1046
0.5203	Remote Similarity	NPC185466
0.52	Remote Similarity	NPC470911
0.519	Remote Similarity	NPC482010
0.5181	Remote Similarity	NPC297950
0.5166	Remote Similarity	NPC135904
0.5163	Remote Similarity	NPC4749
0.5159	Remote Similarity	NPC302543
0.5139	Remote Similarity	NPC123796
0.5132	Remote Similarity	NPC283417
0.5132	Remote Similarity	NPC200049
0.5116	Remote Similarity	NPC485563
0.5105	Remote Similarity	NPC173859
0.5105	Remote Similarity	NPC305267
0.5102	Remote Similarity	NPC295823
0.5102	Remote Similarity	NPC174720
0.5102	Remote Similarity	NPC475467
0.5097	Remote Similarity	NPC265841
0.5096	Remote Similarity	NPC136768
0.5068	Remote Similarity	NPC37134
0.5067	Remote Similarity	NPC473824
0.5067	Remote Similarity	NPC610461
0.5064	Remote Similarity	NPC271610
0.5034	Remote Similarity	NPC470915
0.5034	Remote Similarity	NPC606553
0.5032	Remote Similarity	NPC470518
0.5032	Remote Similarity	NPC57484
0.5032	Remote Similarity	NPC473386

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC43589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8012
0.1-0.2	1107
0.2-0.3	29
0.3-0.4	2
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