NPASS Compound

Natural Product: NPC239627

Natural Product ID	NPC239627
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UYSRWDYTMGBBHP-IWAVKSQDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5318530
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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 67 69 0 0 0 0 0 0 0 0999 V2000 -7.6497 3.5023 0.1158 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1715 2.3043 -0.4275 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7766 1.1036 0.1367 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8909 1.0167 1.2130 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5296 -0.2018 1.7378 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0681 -1.3334 1.1694 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9425 -1.2823 0.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2936 -0.0608 -0.4033 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1787 0.0014 -1.4771 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5968 -0.2911 2.8710 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1740 -0.3863 2.2214 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1862 -1.5263 1.4380 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3905 -2.1111 0.7127 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0232 -1.7401 0.4178 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3527 -0.7115 0.8589 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0303 -0.4604 0.4747 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6724 0.6743 1.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9670 0.9785 0.6894 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7251 0.1743 -0.1733 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1210 -0.9285 -0.6931 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7861 -1.2298 -0.3630 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8290 -1.7549 -1.5509 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1809 -2.8956 -2.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9798 0.5502 -0.4194 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0328 0.0937 -1.1606 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4362 1.1335 -2.1907 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0821 2.3348 -1.5635 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2570 1.8683 -0.7572 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2804 0.3760 -0.6125 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2553 0.0705 0.5331 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7886 0.5912 1.7325 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0850 -0.1978 -0.2917 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2997 2.5161 0.4594 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1796 2.9866 -0.7520 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1983 0.5158 -3.1505 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8178 -3.3241 0.0461 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7532 3.4957 1.2225 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5659 3.5739 -0.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1857 4.3918 -0.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5080 1.9239 1.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8070 -2.3037 1.5553 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3441 -2.1777 -0.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8465 0.3261 -2.3819 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7312 -1.1860 3.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6221 0.5994 3.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0351 0.5436 1.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4502 -0.4813 3.0665 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4408 -2.3939 -0.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8290 -0.0285 1.5234 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1255 1.3253 1.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4238 1.8767 1.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3750 -2.1082 -0.8054 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8034 -3.5565 -1.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2531 -2.5287 -2.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8044 -3.4684 -2.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8798 -0.8351 -1.7420 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4831 1.4853 -2.6631 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3654 3.0213 -2.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1818 2.1481 -1.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7256 -0.1119 -1.5018 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2672 0.4460 0.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3596 -1.0242 0.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1966 -0.0278 2.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2529 2.6959 0.7222 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6769 3.7260 -0.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5855 -0.0210 -3.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7851 -3.5785 0.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 1 0 11 12 1 0 12 13 2 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 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 19 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 29 32 1 0 28 33 1 0 27 34 1 0 26 35 1 0 13 36 1 0 8 3 1 0 21 16 1 0 32 25 1 0 1 37 1 0 1 38 1 0 1 39 1 0 4 40 1 0 6 41 1 0 7 42 1 0 9 43 1 0 10 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 14 48 1 0 15 49 1 0 17 50 1 0 18 51 1 0 21 52 1 0 23 53 1 0 23 54 1 0 23 55 1 0 25 56 1 6 26 57 1 6 27 58 1 6 28 59 1 6 29 60 1 6 30 61 1 0 30 62 1 0 31 63 1 0 33 64 1 0 34 65 1 0 35 66 1 0 36 67 1 0 M END

Standard InCHIKey	UYSRWDYTMGBBHP-IWAVKSQDSA-N
Standard InCHI	InChI=1S/C25H31NO10/c1-33-18-11-15(3-6-16(18)28)9-10-26-21(29)8-5-14-4-7-17(19(12-14)34-2)35-25-24(32)23(31)22(30)20(13-27)36-25/h3-8,11-12,20,22-25,27-28,30-32H,9-10,13H2,1-2H3,(H,26,29)/b8-5+/t20-,22+,23+,24-,25-/m1/s1
SMILES	COc1cc(ccc1O)CCN=C(/C=C/c1ccc(c(c1)OC)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	505.19	Volume:	493.094 ? Van der Waals volume.
Dense:	1.025	LogP:	0.963 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.453 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.431 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	20.0
TPSA:	170.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	3.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.2	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.028	Fsp³:	0.4
MCE-18:	69.0 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.717	Fluc inhibitor:	0.812 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.205 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.901 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.007	Promiscuous compounds:	0.159

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.859	MDCK Permeability:	-5.201
Pgp-inhibitor:	0.0	Pgp-substrate:	0.738
PAMPA:	0.911 ? 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):	0.979
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.005
Plasma Protein Binding (PPB):	86.995%	Volume Distribution (VD):	-0.285
Fu:	12.345% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.015
BSEP inhibitor:	0.202

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.021	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.954	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.108
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.221 ? 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):

3.345

Half-life (T1/2):

2.218

ADMET: Toxicity

hERG Blockers:	0.059	hERG Blockers (10um):	0.1
Human Hepatotoxicity (H-HT):	0.942	Drug-induced Liver Injury (DILI):	0.931
AMES Toxicity:	0.964	Rat Oral Acute Toxicity:	0.126
Maximum Recommended Daily Dose:	0.094	Skin Sensitization:	1.0
Carcinogencity:	0.426	Eye Corrosion:	0.0
Eye Irritation:	0.033	Respiratory Toxicity:	0.345
Drug-induced Neurotoxicity:	0.038	Ototoxicity:	0.952
Hematotoxicity:	0.639	Drug-induced Nephrotoxicity:	0.936
Genotoxicity:	0.526	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.767	Hek293 Cytotoxicity:	0.54
BCF:	0.513 ? 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:	3.135 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.77 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.837 ? 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
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28558206]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32031796]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[8289066]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[8450318]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917283]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26272	Heracleum wallichii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26272	Heracleum wallichii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27817	Stephania hernandifolia	Species	Menispermaceae	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 NPC239627 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	14117
0.1-0.2	30117
0.2-0.3	4339
0.3-0.4	1061
0.4-0.5	180
0.5-0.6	40
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	Natural Product ID
0.6081	Remote Similarity	NPC214869
0.5974	Remote Similarity	NPC302378
0.5921	Remote Similarity	NPC248355
0.5844	Remote Similarity	NPC55040
0.5778	Remote Similarity	NPC185307
0.573	Remote Similarity	NPC299706
0.573	Remote Similarity	NPC115466
0.573	Remote Similarity	NPC61604
0.5604	Remote Similarity	NPC470950
0.5567	Remote Similarity	NPC44507
0.5556	Remote Similarity	NPC37468
0.5521	Remote Similarity	NPC469654
0.5513	Remote Similarity	NPC178571
0.5513	Remote Similarity	NPC195749
0.5513	Remote Similarity	NPC35961
0.5474	Remote Similarity	NPC114659
0.5474	Remote Similarity	NPC139699
0.5464	Remote Similarity	NPC223335
0.5464	Remote Similarity	NPC40920
0.5435	Remote Similarity	NPC163635
0.5417	Remote Similarity	NPC140915
0.5417	Remote Similarity	NPC187028
0.5402	Remote Similarity	NPC38041
0.5402	Remote Similarity	NPC18979
0.5402	Remote Similarity	NPC22150
0.5385	Remote Similarity	NPC210015
0.5376	Remote Similarity	NPC486549
0.5376	Remote Similarity	NPC470235
0.5366	Remote Similarity	NPC604095
0.5319	Remote Similarity	NPC486546
0.5316	Remote Similarity	NPC155838
0.5269	Remote Similarity	NPC46092
0.5256	Remote Similarity	NPC270849
0.5217	Remote Similarity	NPC470413
0.5213	Remote Similarity	NPC129417
0.5213	Remote Similarity	NPC283995
0.5165	Remote Similarity	NPC93924
0.5125	Remote Similarity	NPC479029
0.5106	Remote Similarity	NPC478055
0.5063	Remote Similarity	NPC472024
0.5053	Remote Similarity	NPC486548

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC239627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3366
0.1-0.2	5577
0.2-0.3	193
0.3-0.4	11
0.4-0.5	3
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