NPASS Compound

Natural Product: NPC85593

Natural Product ID	NPC85593
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Polystanin D
IUPAC Name	[(3R,5R,9R,10R,13S,14S,17S)-17-[(2S,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2392322
PubChem CID	71529900
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 93 97 0 0 0 0 0 0 0 0999 V2000 -4.3170 -3.2527 1.0987 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2497 -1.9000 0.8195 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1551 -1.7826 -0.5930 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5255 -1.3896 -0.8590 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6081 -0.0575 -0.4626 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1976 0.4584 -0.2950 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4886 -0.6291 -1.1139 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1379 -0.3002 -1.3894 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4716 -1.1670 -2.4865 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0160 -0.8694 -2.4498 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0535 0.2508 -1.4816 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9901 -0.3055 -0.4898 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7815 -1.7393 -0.1158 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8940 0.4896 0.7170 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4159 0.1547 1.4346 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5610 -0.1344 0.4843 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2542 0.6158 -0.7469 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0644 1.5890 -1.1015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3056 1.9801 -0.3632 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8374 0.6374 0.1174 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9030 0.1114 1.1230 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7761 0.9323 2.3817 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5265 -1.2119 1.6162 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5149 -1.7559 0.6343 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7198 -0.8426 0.4516 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2969 0.6184 0.3696 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8136 1.4258 1.5041 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9166 1.2266 -0.9076 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2712 -1.2013 -0.8011 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5486 -1.6430 -1.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3147 -1.7513 -0.0365 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9349 -1.9717 -2.4194 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3794 1.4037 -2.3163 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4258 0.0905 0.7920 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6205 1.4691 1.2887 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4734 1.3377 2.4291 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3866 2.1399 1.8632 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2998 2.4122 0.3632 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7117 -0.4207 0.5128 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2148 -3.7047 0.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4544 -3.7688 0.6387 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2881 -3.4335 2.1914 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1285 -2.7480 -1.1054 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0545 0.5071 -1.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9057 0.3984 0.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0431 1.4331 -0.7977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0196 -0.4557 -2.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2172 0.7471 -1.7595 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6578 -2.2367 -2.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9647 -0.9443 -3.4264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2399 -0.5318 -3.5190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6892 -1.6951 -2.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1759 -2.3755 -0.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7732 -2.2988 -0.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5190 -1.8863 0.9753 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6715 0.1984 1.4847 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0258 1.5515 0.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6779 1.1508 1.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3089 -0.5455 2.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6148 -1.2034 0.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9034 2.2276 -1.9819 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1011 2.6835 0.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9861 2.4717 -1.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7277 -0.0349 -0.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1013 0.3374 3.0685 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4988 1.9672 2.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7538 0.8681 2.9451 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6805 -1.9276 1.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9446 -1.1393 2.6172 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9046 -2.6984 1.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0166 -1.9932 -0.3142 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4490 -0.9598 1.2702 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8298 1.8368 1.2167 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2067 2.3035 1.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0708 0.8070 2.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0047 2.3272 -0.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9249 0.7981 -1.0805 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2666 1.0479 -1.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1021 -2.6010 -2.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8827 -1.0182 -3.0190 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9047 -2.4628 -2.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5842 2.3401 -1.8305 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5162 1.5550 -3.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0959 1.1431 -3.1692 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9881 -0.5360 1.5710 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7486 2.2715 2.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7485 2.6235 1.1031 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8502 1.5197 2.6023 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7543 3.0202 2.4849 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1394 3.4550 0.7672 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3899 2.2644 0.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8835 2.4364 -0.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9417 -0.1098 -0.4010 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 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 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 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 11 33 1 6 5 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 34 39 1 0 7 3 1 0 12 8 1 0 21 16 1 0 17 11 1 0 26 20 1 0 1 40 1 0 1 41 1 0 1 42 1 0 3 43 1 6 5 44 1 6 6 45 1 0 6 46 1 0 7 47 1 6 8 48 1 6 9 49 1 0 9 50 1 0 10 51 1 0 10 52 1 0 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 6 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 6 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 25 72 1 1 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 28 77 1 0 28 78 1 0 32 79 1 0 32 80 1 0 32 81 1 0 33 82 1 0 33 83 1 0 33 84 1 0 34 85 1 1 36 86 1 0 37 87 1 0 37 88 1 0 37 89 1 0 38 90 1 0 38 91 1 0 38 92 1 0 39 93 1 0 M END

Standard InCHIKey	TYDCQDCBJWPAQE-VPERIMHQSA-N
Standard InCHI	InChI=1S/C33H54O6/c1-19(34)38-26-14-15-31(6)22-13-17-32(7)21(20-18-24(39-28(20)37-9)27(35)30(4,5)36)12-16-33(32,8)23(22)10-11-25(31)29(26,2)3/h10,20-22,24-28,35-36H,11-18H2,1-9H3/t20-,21-,22-,24+,25-,26+,27-,28-,31+,32-,33+/m0/s1
SMILES	CO[C@H]1O[C@H](C[C@H]1[C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)OC(=O)C)C)[C@@H](C(O)(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	546.39	Volume:	584.01 ? Van der Waals volume.
Dense:	0.936	LogP:	4.093 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.774 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.299 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	26.0
TPSA:	85.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.323	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.159	Fsp³:	0.909
MCE-18:	104.127 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.9	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.227	Promiscuous compounds:	0.655

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.118	MDCK Permeability:	-4.879
Pgp-inhibitor:	0.988	Pgp-substrate:	0.328
PAMPA:	0.341 ? 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):	0.0
20% Bioavailability (F20%):	0.067	30% Bioavailability (F30%):	0.115
50% Bioavailability (F50%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023	MRP1:	0.819
Plasma Protein Binding (PPB):	84.208%	Volume Distribution (VD):	-0.256
Fu:	10.621% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.339
BSEP inhibitor:	0.985

ADMET: Metabolism

CYP1A2-inhibitor:	0.174	CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.865	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.853	CYP3A4-substrate:	0.943
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.437 ? 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):

9.867

Half-life (T1/2):

0.662

ADMET: Toxicity

hERG Blockers:	0.099	hERG Blockers (10um):	0.319
Human Hepatotoxicity (H-HT):	0.74	Drug-induced Liver Injury (DILI):	0.635
AMES Toxicity:	0.66	Rat Oral Acute Toxicity:	0.588
Maximum Recommended Daily Dose:	0.605	Skin Sensitization:	0.908
Carcinogencity:	0.748	Eye Corrosion:	0.007
Eye Irritation:	0.466	Respiratory Toxicity:	0.366
Drug-induced Neurotoxicity:	0.198	Ototoxicity:	0.724
Hematotoxicity:	0.498	Drug-induced Nephrotoxicity:	0.771
Genotoxicity:	0.966	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.283	Hek293 Cytotoxicity:	0.398
BCF:	2.089 ? 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:	4.485 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.912 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.41 ? 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
NPO3063	Aphanamixis grandifolia	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23772699]
NPO3063	Aphanamixis grandifolia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3063	Aphanamixis grandifolia	Species	Meliaceae	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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	1800.0	nM	DrugMatrix in vitro pharmacology data

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 NPC85593 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	18223
0.1-0.2	24628
0.2-0.3	6280
0.3-0.4	638
0.4-0.5	58
0.5-0.6	21
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31430
0.875	High Similarity	NPC101450
0.7465	Intermediate Similarity	NPC5358
0.7465	Intermediate Similarity	NPC216260
0.7297	Intermediate Similarity	NPC121566
0.7297	Intermediate Similarity	NPC100955
0.6667	Remote Similarity	NPC189282
0.6667	Remote Similarity	NPC237402
0.6203	Remote Similarity	NPC63023
0.6203	Remote Similarity	NPC95243
0.5844	Remote Similarity	NPC484789
0.5844	Remote Similarity	NPC484801
0.5844	Remote Similarity	NPC484786
0.5844	Remote Similarity	NPC484787
0.5844	Remote Similarity	NPC484788
0.5783	Remote Similarity	NPC470064
0.5783	Remote Similarity	NPC470043
0.5769	Remote Similarity	NPC471293
0.5769	Remote Similarity	NPC324598
0.5532	Remote Similarity	NPC250089
0.5532	Remote Similarity	NPC157530
0.5309	Remote Similarity	NPC484791
0.5309	Remote Similarity	NPC484790
0.5258	Remote Similarity	NPC14630
0.5253	Remote Similarity	NPC488573
0.5253	Remote Similarity	NPC488572
0.5172	Remote Similarity	NPC470060
0.5172	Remote Similarity	NPC470059
0.5122	Remote Similarity	NPC471896
0.5116	Remote Similarity	NPC484792
0.5057	Remote Similarity	NPC470055

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7033
0.1-0.2	2004
0.2-0.3	111
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