NPASS Compound

Natural Product: NPC475175

Natural Product ID	NPC475175
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17S)-8,14,17-Trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-Hydroxy-4-Methoxy-6-Methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-10,13-Dimethyl-12-[(E)-3-Phenylprop-2-Enoyl]Oxy-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-17-Yl]Ethyl] Benzoate
IUPAC Name	[(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17S)-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] benzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500083
PubChem CID	44566878
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 199209 0 0 0 0 0 0 0 0999 V2000 -0.1829 -2.4824 1.0330 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2413 -2.9103 -0.4185 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3750 -1.9168 -1.3148 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6760 -1.2831 -2.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9128 -0.9609 -1.4975 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3084 -2.0231 -0.4722 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5932 -3.1572 -0.7423 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6841 -2.1221 -0.5865 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3672 -1.7464 0.5702 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3768 -2.7687 0.8974 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7704 -2.2899 0.6023 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1782 -1.1162 1.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3950 -0.3834 0.9988 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4620 -1.1054 0.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8469 -0.8934 0.9712 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1065 0.4573 1.3580 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1076 1.3810 0.7842 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9984 2.5043 1.8865 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5108 2.5116 2.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9197 1.3998 1.4726 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0.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 17.5365 3.8712 0.1785 H 0 0 0 0 0 0 0 0 0 0 0 0 16.2174 3.0384 -0.8243 H 0 0 0 0 0 0 0 0 0 0 0 0 17.7837 3.9666 -2.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 19.7355 1.3801 -1.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 19.6546 -1.2577 1.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6323 -0.9758 -0.8932 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0430 2.1557 3.8413 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7901 2.5395 3.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6776 3.3168 2.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4121 2.7015 -1.3785 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1830 -3.1396 -0.4857 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6896 -4.1276 -0.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0443 -4.0966 -1.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1819 2.6130 1.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1813 3.1139 -0.1210 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7141 1.8224 0.9834 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 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 2 0 24 25 1 0 21 26 1 0 20 27 1 0 17 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 17 39 1 0 16 40 1 0 15 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 2 3 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 12 52 1 0 4 53 1 0 53 54 1 0 3 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 60 62 1 0 59 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 67 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 76 78 1 0 75 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 84 86 1 0 86 87 1 0 83 88 1 0 82 89 1 0 81 90 1 0 74 91 1 0 91 92 1 0 73 93 1 0 66 94 1 0 94 95 1 0 58 96 1 0 96 97 1 0 7 2 1 0 77 72 1 0 85 80 1 0 25 9 1 0 24 12 1 0 21 13 1 0 20 16 1 0 38 33 1 0 51 46 1 0 61 56 1 0 69 64 1 0 1 98 1 0 1 99 1 0 1100 1 0 2101 1 0 3102 1 0 4103 1 0 5104 1 0 5105 1 0 6106 1 0 9107 1 0 10108 1 0 10109 1 0 11110 1 0 11111 1 0 13112 1 0 14113 1 0 14114 1 0 15115 1 0 18116 1 0 18117 1 0 19118 1 0 19119 1 0 22120 1 0 22121 1 0 23122 1 0 25123 1 0 25124 1 0 26125 1 0 27126 1 0 28127 1 0 29128 1 0 29129 1 0 29130 1 0 34131 1 0 35132 1 0 36133 1 0 37134 1 0 38135 1 0 39136 1 0 40137 1 0 40138 1 0 40139 1 0 44140 1 0 45141 1 0 47142 1 0 48143 1 0 49144 1 0 50145 1 0 51146 1 0 52147 1 0 52148 1 0 52149 1 0 54150 1 0 54151 1 0 54152 1 0 56153 1 0 57154 1 0 57155 1 0 58156 1 0 59157 1 0 60158 1 0 62159 1 0 62160 1 0 62161 1 0 64162 1 0 65163 1 0 65164 1 0 66165 1 0 67166 1 0 68167 1 0 70168 1 0 70169 1 0 70170 1 0 72171 1 0 73172 1 0 74173 1 0 75174 1 0 76175 1 0 78176 1 0 78177 1 0 78178 1 0 80179 1 0 81180 1 0 82181 1 0 83182 1 0 84183 1 0 86184 1 0 86185 1 0 87186 1 0 88187 1 0 89188 1 0 90189 1 0 92190 1 0 92191 1 0 92192 1 0 93193 1 0 95194 1 0 95195 1 0 95196 1 0 97197 1 0 97198 1 0 97199 1 0 M END

Standard InCHIKey	YEUOZAYTBFZMCA-RRAJTOTRSA-N
Standard InCHI	InChI=1S/C71H102O26/c1-36-59(94-53-32-46(83-9)60(37(2)87-53)95-54-33-47(84-10)61(38(3)88-54)96-66-58(77)63(85-11)62(39(4)89-66)97-65-57(76)56(75)55(74)48(35-72)92-65)45(82-8)31-52(86-36)91-44-25-26-67(6)43(30-44)24-27-70(80)49(67)34-50(93-51(73)23-22-41-18-14-12-15-19-41)68(7)69(79,28-29-71(68,70)81)40(5)90-64(78)42-20-16-13-17-21-42/h12-24,36-40,44-50,52-63,65-66,72,74-77,79-81H,25-35H2,1-11H3/b23-22+/t36-,37-,38-,39-,40+,44+,45+,46-,47-,48-,49-,50-,52+,53+,54+,55-,56+,57-,58-,59-,60-,61-,62-,63+,65+,66+,67+,68-,69-,70+,71-/m1/s1
SMILES	CC1C(C(CC(O1)OC2CCC3(C4CC(C5(C(CCC5(C4(CC=C3C2)O)O)(C(C)OC(=O)C6=CC=CC=C6)O)C)OC(=O)C=CC7=CC=CC=C7)C)OC)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC1C(C(C(C(O1)C)OC1C(C(C(C(O1)CO)O)O)O)OC)O)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1370.67	Volume:	1344.632 ? Van der Waals volume.
Dense:	1.019	LogP:	3.548 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.361 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.785 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	65.0
TPSA:	343.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	8.0	Rings:	11.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.05	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.635	Fsp³:	0.746
MCE-18:	287.968 ? 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:	0.268	Fluc inhibitor:	0.315 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.042 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.334 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.4	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.835	MDCK Permeability:	-5.248
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):	0.995
20% Bioavailability (F20%):	0.349	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	62.707%	Volume Distribution (VD):	-0.582
Fu:	37.921% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.08	BCRP inhibitor:	0.0
BSEP inhibitor:	0.245

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.993	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.711	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.748	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):

0.806

Half-life (T1/2):

7.004

ADMET: Toxicity

hERG Blockers:	0.334	hERG Blockers (10um):	0.679
Human Hepatotoxicity (H-HT):	0.141	Drug-induced Liver Injury (DILI):	0.93
AMES Toxicity:	0.727	Rat Oral Acute Toxicity:	0.617
Maximum Recommended Daily Dose:	0.737	Skin Sensitization:	0.633
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.835	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.024
Genotoxicity:	0.41	RPMI-8226 Immunitoxicity:	0.477
A549 Cytotoxicity:	0.35	Hek293 Cytotoxicity:	0.995
BCF:	0.599 ? 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:	3.758 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.919 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.584 ? 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
NPO33108	leptadenia hastata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623046]
NPO33108	leptadenia hastata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8786361]

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
Activity	6

Activity Type	# Activity
Cell line	6

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	16.0	%	PMID[12825933]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	15.0	%	PMID[27186676]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	6.0	%	PMID[27186676]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	5.0	%	PMID[12825933]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	3.0	%	PMID[12825933]

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 NPC475175 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	12803
0.1-0.2	31469
0.2-0.3	5195
0.3-0.4	341
0.4-0.5	11
0.5-0.6	10
0.6-0.7	13
0.7-0.8	0
0.8-0.85	7
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9292	High Similarity	NPC475531
0.9292	High Similarity	NPC475198
0.8496	Intermediate Similarity	NPC473641
0.8496	Intermediate Similarity	NPC475300
0.8333	Intermediate Similarity	NPC70236
0.8306	Intermediate Similarity	NPC476090
0.8151	Intermediate Similarity	NPC473797
0.812	Intermediate Similarity	NPC475567
0.8	Intermediate Similarity	NPC475447
0.7731	Intermediate Similarity	NPC475437
0.7731	Intermediate Similarity	NPC475464
0.7583	Intermediate Similarity	NPC476092
0.7167	Intermediate Similarity	NPC475613
0.7049	Intermediate Similarity	NPC475218
0.7025	Intermediate Similarity	NPC481654
0.7008	Intermediate Similarity	NPC481660
0.6891	Remote Similarity	NPC473468
0.687	Remote Similarity	NPC102015
0.6777	Remote Similarity	NPC475536
0.6724	Remote Similarity	NPC475358
0.6724	Remote Similarity	NPC473566
0.6667	Remote Similarity	NPC165234
0.6667	Remote Similarity	NPC481659
0.6667	Remote Similarity	NPC271687
0.6639	Remote Similarity	NPC474564
0.6587	Remote Similarity	NPC473557
0.6471	Remote Similarity	NPC481650
0.6303	Remote Similarity	NPC481661
0.6303	Remote Similarity	NPC481655
0.5646	Remote Similarity	NPC481647
0.552	Remote Similarity	NPC305378
0.5328	Remote Similarity	NPC473519
0.5317	Remote Similarity	NPC473805
0.5286	Remote Similarity	NPC481648
0.5227	Remote Similarity	NPC481662
0.5164	Remote Similarity	NPC481657
0.5159	Remote Similarity	NPC481658
0.5159	Remote Similarity	NPC79250
0.5159	Remote Similarity	NPC290746

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475175 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4958
0.1-0.2	4117
0.2-0.3	72
0.3-0.4	3
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