NPASS Compound

Natural Product: NPC471577

Natural Product ID	NPC471577
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Segetalic Acid 28-O-Alpha-L-Arabinopyranosyl-(1->4)-Alpha-L-Arabinopyranosyl-(1->3)-Beta-D-Xylopyranosyl-(1->4)-Alpha-L-Rhamnopyranosyl-(1-> 2)-Beta-D-Fucopyranosyl Ester
IUPAC Name	[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl] (4aR,5R,6aS,6bR,8aR,9S,10S,12aR,14bS)-5,9,10-trihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL260967
PubChem CID	44451495
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 171180 0 0 0 0 0 0 0 0999 V2000 -0.0372 -2.8191 3.6356 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8235 -2.5480 2.3409 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4152 -3.5985 1.3768 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1089 -3.1762 -0.0132 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1376 -1.6834 -0.1242 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9671 -0.9924 0.6716 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6972 -1.2389 1.9879 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2467 -1.5704 0.3614 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2034 -0.8373 -0.3329 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8663 0.3156 -0.6531 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5561 -1.3460 -0.7008 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2987 -2.6460 -1.3992 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2266 -3.7584 -1.1010 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2854 -3.9492 0.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4393 -2.7370 1.2058 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4507 -1.4203 0.4823 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8459 -0.9193 0.2782 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5891 -0.7815 1.3575 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9703 -0.2991 1.2732 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2957 0.6600 0.1610 C 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-1.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1942 2.2002 -0.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0581 1.9192 2.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7684 -0.4233 3.3337 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0093 -2.0874 2.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5150 -1.2068 1.6615 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1333 0.7523 4.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8042 1.9361 2.1843 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0088 2.0019 -0.4269 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8472 -0.3981 -0.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0316 -0.9191 0.4500 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5478 1.2880 2.4616 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6855 -0.4778 2.6577 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7502 -0.6773 -0.0079 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9473 0.3986 -2.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 16.2753 0.1382 -1.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 17.2775 1.9239 0.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 15.9203 2.2875 1.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4983 2.7002 0.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 17.0942 3.6664 -1.0791 H 0 0 0 0 0 0 0 0 0 0 0 0 16.9929 1.0017 -2.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0508 2.6840 -2.2179 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5279 0.0627 -1.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0412 2.9393 -0.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9141 1.1329 0.9224 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7904 2.6830 -1.1364 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3771 1.9330 -0.8504 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8117 -3.3949 -0.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7518 -5.2309 1.4710 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 2 0 9 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 2 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 24 25 1 0 25 26 1 0 26 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 30 34 1 0 29 35 1 0 25 36 1 0 25 37 1 0 24 38 1 0 21 39 1 0 14 40 1 0 14 41 1 0 5 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 47 49 1 0 46 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 69 72 1 0 68 73 1 0 67 74 1 0 61 75 1 0 60 76 1 0 52 77 1 0 45 78 1 0 44 79 1 0 4 80 1 0 3 81 1 0 7 2 1 0 71 66 1 0 16 11 1 0 32 11 1 0 30 17 1 0 29 20 1 0 26 21 1 0 48 43 1 0 56 51 1 0 64 59 1 0 1 82 1 0 1 83 1 0 1 84 1 0 2 85 1 0 3 86 1 0 4 87 1 0 5 88 1 0 6 89 1 0 12 90 1 0 12 91 1 0 13 92 1 0 13 93 1 0 15 94 1 0 15 95 1 0 16 96 1 0 18 97 1 0 19 98 1 0 19 99 1 0 20100 1 0 22101 1 0 22102 1 0 23103 1 0 23104 1 0 24105 1 0 26106 1 0 27107 1 0 27108 1 0 28109 1 0 28110 1 0 31111 1 0 31112 1 0 32113 1 0 33114 1 0 34115 1 0 34116 1 0 34117 1 0 35118 1 0 35119 1 0 35120 1 0 36121 1 0 36122 1 0 36123 1 0 37124 1 0 38125 1 0 39126 1 0 39127 1 0 39128 1 0 40129 1 0 40130 1 0 40131 1 0 41132 1 0 41133 1 0 41134 1 0 43135 1 0 44136 1 0 45137 1 0 46138 1 0 47139 1 0 49140 1 0 49141 1 0 49142 1 0 51143 1 0 52144 1 0 53145 1 0 54146 1 0 55147 1 0 55148 1 0 57149 1 0 59150 1 0 60151 1 0 61152 1 0 62153 1 0 63154 1 0 63155 1 0 66156 1 0 67157 1 0 68158 1 0 69159 1 0 70160 1 0 70161 1 0 72162 1 0 73163 1 0 74164 1 0 75165 1 0 76166 1 0 77167 1 0 78168 1 0 79169 1 0 80170 1 0 81171 1 0 M END

Standard InCHIKey	JWHUAVGIBKOTMH-VMGBBZLZSA-N
Standard InCHI	InChI=1S/C56H90O25/c1-22-33(61)36(64)44(49(75-22)81-50(70)56-16-15-51(3,4)17-25(56)24-9-10-29-52(5)13-12-31(59)55(8,71)30(52)11-14-53(29,6)54(24,7)18-32(56)60)80-48-40(68)37(65)42(23(2)76-48)78-47-41(69)43(27(58)20-73-47)79-46-39(67)35(63)28(21-74-46)77-45-38(66)34(62)26(57)19-72-45/h9,22-23,25-49,57-69,71H,10-21H2,1-8H3/t22-,23+,25+,26+,27-,28+,29?,30-,31+,32-,33+,34+,35+,36+,37+,38-,39-,40-,41-,42+,43+,44-,45+,46+,47+,48+,49+,52-,53-,54-,55+,56-/m1/s1
SMILES	CC1C(C(C(C(O1)OC(=O)C23CCC(CC2C4=CCC5C6(CCC(C(C6CCC5(C4(CC3O)C)C)(C)O)O)C)(C)C)OC7C(C(C(C(O7)C)OC8C(C(C(CO8)O)OC9C(C(C(CO9)OC1C(C(C(CO1)O)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1162.58	Volume:	1106.05 ? Van der Waals volume.
Dense:	1.051	LogP:	-0.177 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.804 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.261 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	57.0
TPSA:	392.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	14.0	Rings:	10.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.079	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.242	Fsp³:	0.946
MCE-18:	217.578 ? 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:	0.006	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.268 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.392	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.699	MDCK Permeability:	-4.764
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.999
20% Bioavailability (F20%):	0.975	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	27.539%	Volume Distribution (VD):	-0.47
Fu:	39.324% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.246	BCRP inhibitor:	0.0
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.462	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.865	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.011	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

-0.895

Half-life (T1/2):

5.753

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.214
Human Hepatotoxicity (H-HT):	0.305	Drug-induced Liver Injury (DILI):	0.388
AMES Toxicity:	0.602	Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.24	Skin Sensitization:	0.009
Carcinogencity:	0.007	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.331	Ototoxicity:	1.0
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.067
Genotoxicity:	0.022	RPMI-8226 Immunitoxicity:	0.127
A549 Cytotoxicity:	0.021	Hek293 Cytotoxicity:	0.838
BCF:	0.469 ? 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:	3.882 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.215 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.36 ? 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
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[16880670]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[17409564]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	roots	n.a.	n.a.	PMID[18194870]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	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
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	23100.0	nM	PMID[20155932]

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 NPC471577 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	23987
0.1-0.2	22318
0.2-0.3	2777
0.3-0.4	524
0.4-0.5	166
0.5-0.6	56
0.6-0.7	20
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC473386
0.8261	Intermediate Similarity	NPC471580
0.775	Intermediate Similarity	NPC309223
0.75	Intermediate Similarity	NPC102505
0.75	Intermediate Similarity	NPC488514
0.7417	Intermediate Similarity	NPC13998
0.6829	Remote Similarity	NPC85154
0.6512	Remote Similarity	NPC144644
0.6512	Remote Similarity	NPC170407
0.6493	Remote Similarity	NPC480421
0.6466	Remote Similarity	NPC8524
0.6418	Remote Similarity	NPC33012
0.6412	Remote Similarity	NPC224381
0.6385	Remote Similarity	NPC37860
0.6316	Remote Similarity	NPC68767
0.625	Remote Similarity	NPC237191
0.6216	Remote Similarity	NPC472270
0.6216	Remote Similarity	NPC112492
0.6194	Remote Similarity	NPC293031
0.6142	Remote Similarity	NPC480423
0.6098	Remote Similarity	NPC104137
0.6098	Remote Similarity	NPC26626
0.609	Remote Similarity	NPC70809
0.6048	Remote Similarity	NPC815
0.6031	Remote Similarity	NPC470876
0.6015	Remote Similarity	NPC33068
0.5986	Remote Similarity	NPC485563
0.5954	Remote Similarity	NPC473452
0.5954	Remote Similarity	NPC286457
0.5909	Remote Similarity	NPC475514
0.5809	Remote Similarity	NPC220160
0.5809	Remote Similarity	NPC142151
0.58	Remote Similarity	NPC23020
0.5797	Remote Similarity	NPC153673
0.5781	Remote Similarity	NPC123522
0.5764	Remote Similarity	NPC297950
0.5763	Remote Similarity	NPC480420
0.5724	Remote Similarity	NPC472268
0.5693	Remote Similarity	NPC267694
0.5683	Remote Similarity	NPC110385
0.5683	Remote Similarity	NPC51099
0.5674	Remote Similarity	NPC275225
0.5606	Remote Similarity	NPC488560
0.5532	Remote Similarity	NPC480422
0.5528	Remote Similarity	NPC488526
0.5512	Remote Similarity	NPC69811
0.5403	Remote Similarity	NPC305267
0.536	Remote Similarity	NPC105800
0.5342	Remote Similarity	NPC489208
0.5338	Remote Similarity	NPC257211
0.5337	Remote Similarity	NPC488513
0.5282	Remote Similarity	NPC478825
0.528	Remote Similarity	NPC164389
0.5256	Remote Similarity	NPC472269
0.5248	Remote Similarity	NPC482010
0.5232	Remote Similarity	NPC475394
0.5227	Remote Similarity	NPC300419
0.5224	Remote Similarity	NPC480419
0.52	Remote Similarity	NPC329893
0.5185	Remote Similarity	NPC475160
0.5185	Remote Similarity	NPC473714
0.5163	Remote Similarity	NPC475584
0.5163	Remote Similarity	NPC475152
0.5143	Remote Similarity	NPC202828
0.5143	Remote Similarity	NPC119592
0.5143	Remote Similarity	NPC236638
0.5143	Remote Similarity	NPC294453
0.5141	Remote Similarity	NPC478823
0.5141	Remote Similarity	NPC51564
0.5133	Remote Similarity	NPC484831
0.5133	Remote Similarity	NPC484830
0.5106	Remote Similarity	NPC302543
0.5106	Remote Similarity	NPC476991
0.5077	Remote Similarity	NPC481079
0.5069	Remote Similarity	NPC480417
0.5064	Remote Similarity	NPC311178
0.5064	Remote Similarity	NPC478559
0.5064	Remote Similarity	NPC478560
0.5041	Remote Similarity	NPC1046
0.5036	Remote Similarity	NPC480418
0.5035	Remote Similarity	NPC481081
0.5034	Remote Similarity	NPC489209

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7779
0.1-0.2	1342
0.2-0.3	29
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