NPASS Compound

Natural Product: NPC171758

Natural Product ID	NPC171758
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BINHPQIJJAQCCK-CONSDPRKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related 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 91 97 0 0 0 0 0 0 0 0999 V2000 -2.1056 -0.3341 -3.9323 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3916 -1.1291 -2.8518 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2551 -1.4093 -1.8050 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3250 -2.2772 -1.9577 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7169 -2.9446 -0.6781 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6410 -2.8888 0.3673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5285 -3.9590 1.2227 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5438 -3.9442 2.1848 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7051 -2.8544 2.2545 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8190 -1.7605 1.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7983 -1.7949 0.4392 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0663 -0.7268 -0.5624 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3320 0.0106 -0.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2341 1.4555 -0.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3306 2.1030 0.5052 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3868 3.4426 0.7251 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3088 4.2300 0.3583 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2322 3.6228 -0.2108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1821 2.2406 -0.4350 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1337 4.4026 -0.5838 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1326 3.9982 -0.1358 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8875 3.2172 -0.9734 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1244 2.7961 -0.5672 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6125 3.1422 0.6524 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8480 3.9315 1.4900 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5991 4.3686 1.1056 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9202 2.6693 1.1132 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3675 1.4411 0.4084 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3500 0.3662 0.3074 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1894 0.3243 1.0125 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2976 -0.7087 0.8302 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5674 -1.7135 -0.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7598 -1.6680 -0.7848 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6378 -0.6357 -0.5950 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9265 -0.5682 -1.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0974 0.8346 -1.8372 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9963 1.8106 -0.8153 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3357 2.3504 -0.5517 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6833 -2.7645 -0.2656 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0032 -3.7737 -1.1959 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0897 -0.7426 1.5669 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3751 5.6054 0.5880 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5076 6.1818 1.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2883 -2.8606 3.2400 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5732 -3.3896 3.0343 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4048 -5.0087 3.0629 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2863 -6.1148 2.9620 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4267 0.4639 -4.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4505 -0.9760 -4.7671 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0060 0.1773 -3.5287 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0487 -2.0727 -3.3524 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4747 -0.6338 -2.4930 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0894 -3.0257 -2.7501 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2373 -1.7442 -2.3584 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9465 -4.0253 -0.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6524 -2.5396 -0.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2063 -4.8249 1.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2045 -0.0796 -0.6583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0692 -0.1775 -1.0718 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8157 -0.4446 0.6623 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1937 1.5094 0.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2414 3.9478 1.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2981 1.8298 -0.8966 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5191 2.9432 -1.9349 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7042 2.1848 -1.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2705 4.1904 2.4553 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0100 4.9741 1.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8278 2.5218 2.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6969 3.4660 1.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1843 0.9922 1.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9862 1.1099 1.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0038 -2.4486 -1.5011 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7909 -0.7805 -0.6177 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0046 -1.3263 -2.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1141 0.9333 -2.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3728 0.9910 -2.6751 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9439 2.2247 -1.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3169 3.3941 -0.2192 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7654 1.6831 0.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1857 -4.4872 -1.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9312 -4.2880 -0.8371 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2620 -3.3567 -2.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4370 6.0467 0.5880 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6782 5.6454 2.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3815 7.2358 1.4434 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7260 -3.8383 2.0389 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8282 -4.1582 3.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3623 -2.6056 3.1574 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2403 -6.5585 1.9369 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0521 -6.8961 3.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3338 -5.7508 3.1194 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 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 32 39 1 0 39 40 1 0 31 41 1 0 17 42 1 0 42 43 1 0 9 44 1 0 44 45 1 0 8 46 1 0 46 47 1 0 12 3 1 0 19 14 1 0 26 21 1 0 37 28 1 0 11 6 1 0 34 29 1 0 41 10 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 2 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 7 57 1 0 12 58 1 6 13 59 1 0 13 60 1 0 15 61 1 0 16 62 1 0 19 63 1 0 22 64 1 0 23 65 1 0 25 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 28 70 1 1 30 71 1 0 33 72 1 0 35 73 1 0 35 74 1 0 36 75 1 0 36 76 1 0 38 77 1 0 38 78 1 0 38 79 1 0 40 80 1 0 40 81 1 0 40 82 1 0 43 83 1 0 43 84 1 0 43 85 1 0 45 86 1 0 45 87 1 0 45 88 1 0 47 89 1 0 47 90 1 0 47 91 1 0 M END

Standard InCHIKey	BINHPQIJJAQCCK-CONSDPRKSA-N
Standard InCHI	InChI=1S/C39H44N2O6/c1-7-41-17-15-27-22-36(44-5)38(45-6)39-37(27)31(41)19-25-10-13-32(42-3)34(20-25)46-28-11-8-24(9-12-28)18-30-29-23-35(47-39)33(43-4)21-26(29)14-16-40(30)2/h8-13,20-23,30-31H,7,14-19H2,1-6H3/t30-,31-/m0/s1
SMILES	CCN1CCc2cc(c(c3c2[C@@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@H]1c2cc(c(cc2CCN1C)OC)O3)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.32	Volume:	666.302 ? Van der Waals volume.
Dense:	0.955	LogP:	3.881 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.331 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.058 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	61.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	8.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.223	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.758	Fsp³:	0.385
MCE-18:	128.556 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.998	Fluc inhibitor:	0.07 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.597 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.925 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.235

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.561	MDCK Permeability:	-4.702
Pgp-inhibitor:	0.946	Pgp-substrate:	0.927
PAMPA:	0.0 ? 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):	0.0
20% Bioavailability (F20%):	0.409	30% Bioavailability (F30%):	0.434
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.942	MRP1:	0.993
Plasma Protein Binding (PPB):	78.844%	Volume Distribution (VD):	0.144
Fu:	19.712% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.761
OATP1B3 inhibitor:	0.941	BCRP inhibitor:	0.954
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.994	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.785
CYP2B6-substrate:	0.998	CYP2C8-inhibitor:	0.242
HLM stability:	0.546 ? 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):

9.361

Half-life (T1/2):

2.072

ADMET: Toxicity

hERG Blockers:	0.912	hERG Blockers (10um):	0.87
Human Hepatotoxicity (H-HT):	0.531	Drug-induced Liver Injury (DILI):	0.007
AMES Toxicity:	0.587	Rat Oral Acute Toxicity:	0.698
Maximum Recommended Daily Dose:	0.966	Skin Sensitization:	0.676
Carcinogencity:	0.804	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.893
Drug-induced Neurotoxicity:	0.925	Ototoxicity:	0.501
Hematotoxicity:	0.084	Drug-induced Nephrotoxicity:	0.28
Genotoxicity:	0.479	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.145	Hek293 Cytotoxicity:	0.709
BCF:	2.184 ? 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:	4.694 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.214 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.577 ? 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
NPO19097	Asparagus umbellatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12105	Chondrodendron microphyllum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15528	Cyclea peltata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18271	Lucuma mammosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19375	Phellandrium aquaticum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16804	Ruscus colchicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19640	Solanum cyananthum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16804	Ruscus colchicus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19640	Solanum cyananthum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12105	Chondrodendron microphyllum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15528	Cyclea peltata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19097	Asparagus umbellatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18271	Lucuma mammosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19375	Phellandrium aquaticum	n.a.	n.a.	n.a.	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 NPC171758 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	32144
0.1-0.2	16984
0.2-0.3	490
0.3-0.4	109
0.4-0.5	36
0.5-0.6	34
0.6-0.7	29
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9077	High Similarity	NPC76682
0.9077	High Similarity	NPC10908
0.9077	High Similarity	NPC63646
0.9077	High Similarity	NPC317145
0.9077	High Similarity	NPC198498
0.9077	High Similarity	NPC115284
0.8657	High Similarity	NPC276890
0.8169	Intermediate Similarity	NPC480587
0.7917	Intermediate Similarity	NPC73492
0.7917	Intermediate Similarity	NPC299990
0.7639	Intermediate Similarity	NPC12424
0.7639	Intermediate Similarity	NPC129518
0.7639	Intermediate Similarity	NPC251580
0.7534	Intermediate Similarity	NPC603853
0.75	Intermediate Similarity	NPC227060
0.7424	Intermediate Similarity	NPC247639
0.7424	Intermediate Similarity	NPC25084
0.7368	Intermediate Similarity	NPC185639
0.7368	Intermediate Similarity	NPC251735
0.7368	Intermediate Similarity	NPC49075
0.7368	Intermediate Similarity	NPC599951
0.7237	Intermediate Similarity	NPC311973
0.72	Intermediate Similarity	NPC290582
0.72	Intermediate Similarity	NPC217748
0.72	Intermediate Similarity	NPC182052
0.72	Intermediate Similarity	NPC271013
0.72	Intermediate Similarity	NPC42663
0.72	Intermediate Similarity	NPC15414
0.7143	Intermediate Similarity	NPC116465
0.7143	Intermediate Similarity	NPC223690
0.7143	Intermediate Similarity	NPC9532
0.7105	Intermediate Similarity	NPC279228
0.697	Remote Similarity	NPC317439
0.6795	Remote Similarity	NPC239824
0.6709	Remote Similarity	NPC254441
0.6667	Remote Similarity	NPC195538
0.6667	Remote Similarity	NPC480590
0.6585	Remote Similarity	NPC475479
0.6585	Remote Similarity	NPC243454
0.6585	Remote Similarity	NPC323537
0.6506	Remote Similarity	NPC24260
0.6506	Remote Similarity	NPC485712
0.6447	Remote Similarity	NPC41376
0.642	Remote Similarity	NPC229373
0.6364	Remote Similarity	NPC603603
0.6279	Remote Similarity	NPC480586
0.6265	Remote Similarity	NPC16357
0.6265	Remote Similarity	NPC302245
0.619	Remote Similarity	NPC212237
0.6163	Remote Similarity	NPC10871
0.6145	Remote Similarity	NPC181796
0.6145	Remote Similarity	NPC290005
0.6145	Remote Similarity	NPC54654
0.6145	Remote Similarity	NPC7715
0.6145	Remote Similarity	NPC328155
0.6145	Remote Similarity	NPC222661
0.6145	Remote Similarity	NPC285931
0.6118	Remote Similarity	NPC611658
0.6024	Remote Similarity	NPC274716
0.6024	Remote Similarity	NPC167116
0.6024	Remote Similarity	NPC609821
0.5843	Remote Similarity	NPC281581
0.5795	Remote Similarity	NPC239584
0.5783	Remote Similarity	NPC475393
0.5778	Remote Similarity	NPC485711
0.5714	Remote Similarity	NPC30779
0.5652	Remote Similarity	NPC41122
0.5652	Remote Similarity	NPC318805
0.561	Remote Similarity	NPC480591
0.5595	Remote Similarity	NPC286119
0.5588	Remote Similarity	NPC213206
0.5588	Remote Similarity	NPC188163
0.5588	Remote Similarity	NPC328750
0.5584	Remote Similarity	NPC317272
0.5584	Remote Similarity	NPC268503
0.557	Remote Similarity	NPC256012
0.557	Remote Similarity	NPC610965
0.5568	Remote Similarity	NPC249996
0.5495	Remote Similarity	NPC206900
0.5495	Remote Similarity	NPC82457
0.5484	Remote Similarity	NPC475597
0.5441	Remote Similarity	NPC314682
0.5393	Remote Similarity	NPC8836
0.5333	Remote Similarity	NPC104196
0.5326	Remote Similarity	NPC11296
0.5326	Remote Similarity	NPC274661
0.5294	Remote Similarity	NPC608819
0.5233	Remote Similarity	NPC112248
0.5222	Remote Similarity	NPC275680
0.5222	Remote Similarity	NPC22115
0.5122	Remote Similarity	NPC480592
0.5119	Remote Similarity	NPC240841
0.5111	Remote Similarity	NPC139783
0.5111	Remote Similarity	NPC65312
0.5111	Remote Similarity	NPC611798

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC171758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4700
0.1-0.2	4305
0.2-0.3	122
0.3-0.4	17
0.4-0.5	2
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9077	High Similarity	NPD8099	Discontinued
0.8824	High Similarity	NPD8156	Discontinued
0.7432	Intermediate Similarity	NPD8095	Phase 1
0.5588	Remote Similarity	NPD4664	Clinical (unspecified phase)

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