NPASS Compound

Natural Product: NPC501651

Natural Product ID	NPC501651
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(3~{S},5~{R},8~{R},9~{S},10~{S},12~{S},13~{S},14~{S},17~{R})-3-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-11-oxo-2,3,4,5,6,7,8,9,12,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthren-17-yl]-2~{H}-furan-5-one
IUPAC Name	3-[(3~{S},5~{R},8~{R},9~{S},10~{S},12~{S},13~{S},14~{S},17~{R})-3-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-11-oxo-2,3,4,5,6,7,8,9,12,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthren-17-yl]-2~{H}-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 84 89 0 0 0 0 0 0 0 0999 V2000 -8.1953 2.5454 -0.8620 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2808 1.5084 -1.0016 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5805 1.3714 0.1718 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6905 0.0010 0.7946 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0196 -0.3301 1.0695 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1106 -1.0065 -0.1428 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2095 -1.9378 0.6841 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3528 -0.4912 -1.1456 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4695 0.5097 -0.8382 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4305 -0.0350 -0.1311 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2119 0.0097 -0.7960 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2917 0.8470 0.0602 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6497 -0.0938 1.0537 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3076 -1.0203 0.3647 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4654 -2.2375 1.2877 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2052 -1.5039 -0.9453 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2695 -0.8241 -2.1628 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7022 -0.3557 -2.1242 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3865 -0.9626 -0.8896 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6627 -0.3274 0.2659 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4165 -0.3851 1.5277 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0103 0.1713 2.5244 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6777 -1.1366 1.5478 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5027 -2.5042 1.3814 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5368 -0.5938 0.4219 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8710 -1.3094 0.4114 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7017 0.8559 0.4095 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4533 1.5153 1.4727 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1578 1.0721 2.4665 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6992 2.1875 3.2359 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4239 2.0894 4.2596 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2847 3.3509 2.6546 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5008 3.0148 1.5413 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1903 1.1741 -0.9661 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3958 0.2173 -1.8187 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8523 -0.8437 -0.9244 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3744 -2.0694 -1.4103 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7284 -1.4183 -0.9108 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 1.6182 -0.0244 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4816 1.7749 1.1935 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7572 2.6616 -1.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8429 2.2921 0.0129 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6834 3.5016 -0.5696 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9163 2.1114 0.9251 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0876 0.0341 1.7220 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4211 0.4476 1.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8961 -1.6946 -0.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4710 -2.3630 -0.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8148 -2.7172 1.1868 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6616 -1.2960 1.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0481 0.8888 -1.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2816 0.4843 -1.7861 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5428 1.3993 -0.5404 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8182 1.6225 0.6494 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4894 -0.7425 1.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2252 0.3990 1.9213 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5955 -2.5293 1.5424 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9417 -1.9761 2.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8896 -3.0918 0.7573 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0075 -2.6090 -1.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4273 -0.0043 -2.4768 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2151 -1.5540 -3.0253 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6471 0.7502 -1.9002 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2659 -0.5706 -3.0426 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0835 -2.0308 -0.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3817 0.7376 0.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -0.9974 2.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1298 -2.9200 0.7701 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9196 -1.9991 1.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 -0.5988 0.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0259 -1.9588 -0.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6633 1.3114 0.4613 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3190 0.0315 2.6818 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8749 3.4536 0.5973 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4784 3.4297 1.7234 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2774 1.0692 -1.0960 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9333 2.2377 -1.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6312 0.7922 -2.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1036 -0.1640 -2.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5908 -2.0146 -2.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1154 -1.8270 -1.8630 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1006 -1.9988 -0.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9922 2.5564 -0.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9745 0.9979 1.4933 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 4 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 1 14 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 2 0 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 27 34 1 0 34 35 1 0 35 36 1 0 36 37 1 6 16 38 1 0 9 39 1 0 39 40 1 0 39 3 1 0 38 11 1 0 20 14 1 0 36 25 1 0 36 19 1 0 33 28 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 1 4 45 1 1 5 46 1 0 6 47 1 6 7 48 1 0 7 49 1 0 7 50 1 0 9 51 1 6 11 52 1 6 12 53 1 0 12 54 1 0 13 55 1 0 13 56 1 0 15 57 1 0 15 58 1 0 15 59 1 0 16 60 1 6 17 61 1 0 17 62 1 0 18 63 1 0 18 64 1 0 19 65 1 6 20 66 1 6 23 67 1 1 24 68 1 0 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 6 29 73 1 0 33 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 35 78 1 0 35 79 1 0 37 80 1 0 38 81 1 0 38 82 1 0 39 83 1 6 40 84 1 0 M END

Standard InCHIKey	TYVPUZUDLFQZOP-CRIZSVAQSA-N
Standard InCHI	InChI=1S/C30H44O10/c1-14-22(32)25(37-4)24(34)27(39-14)40-17-7-9-28(2)16(12-17)5-6-19-21(28)23(33)26(35)29(3)18(8-10-30(19,29)36)15-11-20(31)38-13-15/h11,14,16-19,21-22,24-27,32,34-36H,5-10,12-13H2,1-4H3/t14-,16+,17-,18+,19+,21+,22-,24+,25-,26+,27+,28-,29-,30-/m0/s1
SMILES	CO[C@H]1[C@@H](O)[C@H](C)O[C@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3C(=O)[C@@H](O)[C@]3(C)[C@@H](C5=CC(=O)OC5)CC[C@]43O)C2)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	564.29	Volume:	556.09 ? Van der Waals volume.
Dense:	1.015	LogP:	1.114 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.789 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.476 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	151.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.29	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.457	Fsp³:	0.867
MCE-18:	114.214 ? 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:	0.612	Fluc inhibitor:	0.014 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? 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:	0.134	Promiscuous compounds:	0.506

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.566	MDCK Permeability:	-5.176
Pgp-inhibitor:	0.022	Pgp-substrate:	0.93
PAMPA:	0.999 ? 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):	0.006
20% Bioavailability (F20%):	0.087	30% Bioavailability (F30%):	0.047
50% Bioavailability (F50%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.615
Plasma Protein Binding (PPB):	48.286%	Volume Distribution (VD):	-0.429
Fu:	55.149% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.974
OATP1B3 inhibitor:	0.43	BCRP inhibitor:	0.129
BSEP inhibitor:	0.794

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
HLM stability:	0.385 ? 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):

3.181

Half-life (T1/2):

3.323

ADMET: Toxicity

hERG Blockers:	0.093	hERG Blockers (10um):	0.473
Human Hepatotoxicity (H-HT):	0.49	Drug-induced Liver Injury (DILI):	0.838
AMES Toxicity:	0.89	Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.923	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.997
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.787
Hematotoxicity:	0.898	Drug-induced Nephrotoxicity:	0.989
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.908
A549 Cytotoxicity:	0.503	Hek293 Cytotoxicity:	0.966
BCF:	0.5 ? 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:	3.219 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.802 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.865 ? 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
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9481	Strophanthus divaricatus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9481	Strophanthus divaricatus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9481	Strophanthus divaricatus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9481	Strophanthus divaricatus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11771	Strophanthus kombe	Species	Apocynaceae	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 NPC501651 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	11819
0.1-0.2	33330
0.2-0.3	4394
0.3-0.4	138
0.4-0.5	136
0.5-0.6	28
0.6-0.7	8
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	Natural Product ID
0.7349	Intermediate Similarity	NPC199428
0.7349	Intermediate Similarity	NPC109448
0.7349	Intermediate Similarity	NPC310341
0.6667	Remote Similarity	NPC250556
0.6628	Remote Similarity	NPC479356
0.6628	Remote Similarity	NPC479355
0.6591	Remote Similarity	NPC305574
0.6559	Remote Similarity	NPC55532
0.6196	Remote Similarity	NPC5883
0.6136	Remote Similarity	NPC486129
0.6067	Remote Similarity	NPC486126
0.5824	Remote Similarity	NPC84949
0.5824	Remote Similarity	NPC480562
0.5824	Remote Similarity	NPC74945
0.5824	Remote Similarity	NPC31354
0.5824	Remote Similarity	NPC69576
0.567	Remote Similarity	NPC486151
0.5667	Remote Similarity	NPC99620
0.5667	Remote Similarity	NPC479351
0.5667	Remote Similarity	NPC479352
0.5532	Remote Similarity	NPC179412
0.5532	Remote Similarity	NPC93883
0.5532	Remote Similarity	NPC471356
0.5532	Remote Similarity	NPC471353
0.5361	Remote Similarity	NPC173555
0.5326	Remote Similarity	NPC471633
0.5248	Remote Similarity	NPC486143
0.5248	Remote Similarity	NPC486142
0.5248	Remote Similarity	NPC486149
0.5213	Remote Similarity	NPC5311
0.5213	Remote Similarity	NPC469750
0.5213	Remote Similarity	NPC99080
0.5208	Remote Similarity	NPC483822
0.5208	Remote Similarity	NPC484202
0.5158	Remote Similarity	NPC76572
0.5158	Remote Similarity	NPC193382
0.5102	Remote Similarity	NPC72260
0.505	Remote Similarity	NPC480910
0.505	Remote Similarity	NPC480909

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC501651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5094
0.1-0.2	3921
0.2-0.3	120
0.3-0.4	4
0.4-0.5	3
0.5-0.6	7
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
0.6667	Remote Similarity	NPD7507	Pre-clinical
0.5761	Remote Similarity	NPD8335	Phase 4
0.5368	Remote Similarity	NPD8380	Approved
0.5361	Remote Similarity	NPD8296	Phase 4
0.5347	Remote Similarity	NPD8378	Pre-clinical
0.5347	Remote Similarity	NPD8379	Approved
0.5102	Remote Similarity	NPD8294	Phase 4
0.5098	Remote Similarity	NPD8377	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