NPASS Compound

Natural Product: NPC214890

Natural Product ID	NPC214890
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PPRBGLSUFCQJIB-RZNWDTDDSA-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: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 80 85 0 0 0 0 0 0 0 0999 V2000 -0.2638 -2.7218 -0.7715 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1024 -1.2737 -0.4003 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5728 -0.5967 -1.6012 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0719 -0.8285 -1.4059 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5093 0.1802 -0.3562 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5731 0.1669 0.7975 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7157 -1.1012 0.8562 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1069 -1.0036 2.0959 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4480 -1.6435 2.0272 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2520 -1.3168 0.8151 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4095 -0.5682 -0.1930 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2146 -0.4130 -1.4074 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5077 -0.2639 -1.3364 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2991 -0.2324 -0.0820 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4558 -1.1736 -0.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7374 1.1904 0.1854 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6234 1.3813 1.6874 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3218 0.6250 1.9797 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5237 -0.6087 1.1369 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2849 -1.4946 1.9363 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0793 1.5146 -0.2903 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1018 1.9207 0.4344 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2636 2.1376 -0.4129 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4278 2.5258 -0.0946 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8853 1.8376 -1.7048 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5496 1.4512 -1.6906 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8312 0.0315 0.0053 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6321 1.1165 -0.3404 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1820 1.8363 0.8741 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2022 0.9662 1.5329 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2464 0.6004 0.5035 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6575 0.0777 -0.7658 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3334 -1.4114 -0.6140 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9964 -1.9552 -1.8578 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6061 0.7916 -1.2593 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9941 1.7466 0.2265 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8702 1.6920 2.5418 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8339 2.9811 0.4031 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7615 -3.1531 -0.8505 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6923 -2.7846 -1.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8103 -3.3240 -0.0487 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2087 -1.0959 -2.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3862 0.4832 -1.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2975 -1.8192 -1.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6103 -0.6934 -2.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4098 1.1854 -0.8605 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1743 0.1505 1.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8953 1.0272 0.8636 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3708 -1.9963 0.9356 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4568 -1.4729 2.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2486 0.0603 2.3873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3853 -2.7569 2.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0317 -1.2704 2.9206 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5447 -2.2802 0.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1642 0.4594 0.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7256 -0.4232 -2.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0610 -0.1529 -2.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4410 -0.6806 -0.0326 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3405 -2.0894 0.4105 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5029 -1.5553 -1.2678 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9469 1.8576 -0.2609 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5121 2.4675 1.8852 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4783 0.9443 2.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2634 0.4085 3.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5094 1.2636 1.6366 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1191 -1.3303 2.9010 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1268 2.0876 1.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9943 2.1901 -2.3394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4741 0.4506 -2.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9493 1.8539 -0.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3415 2.1254 1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6946 0.0998 1.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9394 -0.1506 0.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4759 0.1089 -1.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2293 -1.9265 -0.2114 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5102 -1.5922 0.0754 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2441 -2.9308 -1.9032 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1104 2.2900 1.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6966 2.6445 2.4878 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6406 3.1556 -0.5466 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 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 2 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 16 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 5 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 7 2 1 0 19 10 1 0 26 21 1 0 35 28 1 0 11 2 1 0 19 14 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 5 46 1 6 6 47 1 0 6 48 1 0 7 49 1 1 8 50 1 0 8 51 1 0 9 52 1 0 9 53 1 0 10 54 1 6 11 55 1 1 12 56 1 0 13 57 1 0 15 58 1 0 15 59 1 0 15 60 1 0 16 61 1 6 17 62 1 0 17 63 1 0 18 64 1 0 18 65 1 0 20 66 1 0 22 67 1 0 26 68 1 0 26 69 1 0 28 70 1 6 29 71 1 1 30 72 1 1 31 73 1 1 32 74 1 6 33 75 1 0 33 76 1 0 34 77 1 0 36 78 1 0 37 79 1 0 38 80 1 0 M END

Standard InCHIKey	PPRBGLSUFCQJIB-RZNWDTDDSA-N
Standard InCHI	InChI=1S/C29H42O9/c1-27-8-5-17(37-26-25(34)24(33)23(32)21(13-30)38-26)12-16(27)3-4-20-19(27)6-9-28(2)18(7-10-29(20,28)35)15-11-22(31)36-14-15/h6,9,11,16-21,23-26,30,32-35H,3-5,7-8,10,12-14H2,1-2H3/t16-,17+,18-,19+,20-,21-,23-,24-,25-,26-,27+,28-,29+/m1/s1
SMILES	C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2C=C[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1)O[C@H]1[C@@H]([C@@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.28	Volume:	530.004 ? Van der Waals volume.
Dense:	1.008	LogP:	1.062 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.61 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.102 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	32.0
TPSA:	145.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.204	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.372	Fsp³:	0.828
MCE-18:	108.906 ? 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:	0.713	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.153	Promiscuous compounds:	0.328

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.222	MDCK Permeability:	-5.299
Pgp-inhibitor:	0.001	Pgp-substrate:	0.899
PAMPA:	0.993 ? 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):	0.03
20% Bioavailability (F20%):	0.737	30% Bioavailability (F30%):	0.805
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.856
Plasma Protein Binding (PPB):	70.093%	Volume Distribution (VD):	-0.558
Fu:	26.909% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.897	BCRP inhibitor:	0.006
BSEP inhibitor:	0.158

ADMET: Metabolism

CYP1A2-inhibitor:	0.014	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.88	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.313	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.577
HLM stability:	0.22 ? 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):

1.935

Half-life (T1/2):

2.443

ADMET: Toxicity

hERG Blockers:	0.231	hERG Blockers (10um):	0.617
Human Hepatotoxicity (H-HT):	0.79	Drug-induced Liver Injury (DILI):	0.484
AMES Toxicity:	0.74	Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.787	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.969
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.92
Hematotoxicity:	0.51	Drug-induced Nephrotoxicity:	0.919
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.792
A549 Cytotoxicity:	0.544	Hek293 Cytotoxicity:	0.976
BCF:	0.741 ? 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:	3.19 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.497 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.954 ? 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
NPO28744	Murraya crenulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28744	Murraya crenulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28744	Murraya crenulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28744	Murraya crenulata	Species	Rutaceae	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 NPC214890 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	14977
0.1-0.2	28071
0.2-0.3	5279
0.3-0.4	1294
0.4-0.5	100
0.5-0.6	88
0.6-0.7	40
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
0.7692	Intermediate Similarity	NPC5311
0.725	Intermediate Similarity	NPC77299
0.725	Intermediate Similarity	NPC480906
0.7059	Intermediate Similarity	NPC30483
0.7059	Intermediate Similarity	NPC470897
0.6977	Remote Similarity	NPC236973
0.6951	Remote Similarity	NPC480914
0.679	Remote Similarity	NPC99620
0.6782	Remote Similarity	NPC292467
0.6747	Remote Similarity	NPC76572
0.6747	Remote Similarity	NPC193382
0.6742	Remote Similarity	NPC486143
0.6742	Remote Similarity	NPC486142
0.6742	Remote Similarity	NPC486149
0.6705	Remote Similarity	NPC240070
0.6628	Remote Similarity	NPC480907
0.6591	Remote Similarity	NPC32177
0.6591	Remote Similarity	NPC469756
0.6591	Remote Similarity	NPC275901
0.6556	Remote Similarity	NPC208193
0.6517	Remote Similarity	NPC480910
0.6517	Remote Similarity	NPC480909
0.6413	Remote Similarity	NPC486146
0.6395	Remote Similarity	NPC471353
0.6374	Remote Similarity	NPC486135
0.6374	Remote Similarity	NPC486137
0.6333	Remote Similarity	NPC188234
0.6316	Remote Similarity	NPC486144
0.6316	Remote Similarity	NPC486145
0.6316	Remote Similarity	NPC486147
0.6316	Remote Similarity	NPC486148
0.6235	Remote Similarity	NPC469750
0.6146	Remote Similarity	NPC475590
0.6129	Remote Similarity	NPC232785
0.6129	Remote Similarity	NPC486139
0.6118	Remote Similarity	NPC84987
0.6087	Remote Similarity	NPC231518
0.6087	Remote Similarity	NPC488944
0.6044	Remote Similarity	NPC40749
0.6023	Remote Similarity	NPC179412
0.6023	Remote Similarity	NPC471356
0.6022	Remote Similarity	NPC125077
0.602	Remote Similarity	NPC120390
0.602	Remote Similarity	NPC74259
0.602	Remote Similarity	NPC475419
0.5979	Remote Similarity	NPC486136
0.596	Remote Similarity	NPC117445
0.596	Remote Similarity	NPC474908
0.596	Remote Similarity	NPC308262
0.596	Remote Similarity	NPC486134
0.596	Remote Similarity	NPC486141
0.5895	Remote Similarity	NPC329986
0.5895	Remote Similarity	NPC140092
0.5833	Remote Similarity	NPC486138
0.5833	Remote Similarity	NPC276838
0.5784	Remote Similarity	NPC474423
0.5747	Remote Similarity	NPC196429
0.5745	Remote Similarity	NPC488941
0.5745	Remote Similarity	NPC488940
0.5714	Remote Similarity	NPC479360
0.5714	Remote Similarity	NPC479359
0.5714	Remote Similarity	NPC488943
0.5714	Remote Similarity	NPC488942
0.5638	Remote Similarity	NPC486130
0.5632	Remote Similarity	NPC471633
0.5612	Remote Similarity	NPC475219
0.5579	Remote Similarity	NPC264336
0.5579	Remote Similarity	NPC486127
0.5556	Remote Similarity	NPC488938
0.5556	Remote Similarity	NPC488937
0.5506	Remote Similarity	NPC157376
0.5506	Remote Similarity	NPC142066
0.5506	Remote Similarity	NPC603972
0.5474	Remote Similarity	NPC32793
0.5474	Remote Similarity	NPC116075
0.5455	Remote Similarity	NPC99728
0.5455	Remote Similarity	NPC87250
0.5455	Remote Similarity	NPC244402
0.5455	Remote Similarity	NPC50305
0.5444	Remote Similarity	NPC199428
0.5444	Remote Similarity	NPC109448
0.5444	Remote Similarity	NPC310341
0.5437	Remote Similarity	NPC486150
0.5417	Remote Similarity	NPC475629
0.5408	Remote Similarity	NPC488939
0.5385	Remote Similarity	NPC488945
0.5385	Remote Similarity	NPC488946
0.5376	Remote Similarity	NPC72260
0.5361	Remote Similarity	NPC59288
0.5333	Remote Similarity	NPC17896
0.5333	Remote Similarity	NPC469755
0.5333	Remote Similarity	NPC284406
0.5333	Remote Similarity	NPC197707
0.5333	Remote Similarity	NPC251866
0.5333	Remote Similarity	NPC480915
0.5326	Remote Similarity	NPC305574
0.5319	Remote Similarity	NPC173555
0.5312	Remote Similarity	NPC475556
0.5312	Remote Similarity	NPC479353
0.5312	Remote Similarity	NPC479354
0.5312	Remote Similarity	NPC311706
0.5306	Remote Similarity	NPC469749
0.53	Remote Similarity	NPC486132
0.53	Remote Similarity	NPC486131
0.5275	Remote Similarity	NPC84949
0.5275	Remote Similarity	NPC480562
0.5275	Remote Similarity	NPC74945
0.5275	Remote Similarity	NPC31354
0.5275	Remote Similarity	NPC69576
0.5269	Remote Similarity	NPC471354
0.5269	Remote Similarity	NPC27507
0.5248	Remote Similarity	NPC486128
0.5217	Remote Similarity	NPC77319
0.5217	Remote Similarity	NPC471351
0.5217	Remote Similarity	NPC471355
0.5189	Remote Similarity	NPC488947
0.5161	Remote Similarity	NPC483822
0.5161	Remote Similarity	NPC9499
0.5161	Remote Similarity	NPC471360
0.5161	Remote Similarity	NPC469751
0.5161	Remote Similarity	NPC93883
0.5161	Remote Similarity	NPC471361
0.5161	Remote Similarity	NPC86159
0.5161	Remote Similarity	NPC469752
0.5161	Remote Similarity	NPC469754
0.5161	Remote Similarity	NPC70542
0.51	Remote Similarity	NPC146857
0.51	Remote Similarity	NPC247190
0.5093	Remote Similarity	NPC286809
0.5055	Remote Similarity	NPC309034
0.5054	Remote Similarity	NPC146456
0.5052	Remote Similarity	NPC27363
0.5048	Remote Similarity	NPC486140

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC214890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6071
0.1-0.2	2963
0.2-0.3	92
0.3-0.4	10
0.4-0.5	8
0.5-0.6	5
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
0.6087	Remote Similarity	NPD8033	Approved
0.5376	Remote Similarity	NPD8294	Phase 4
0.5333	Remote Similarity	NPD7319	Approved
0.5319	Remote Similarity	NPD8296	Phase 4
0.5217	Remote Similarity	NPD8335	Phase 4
0.5161	Remote Similarity	NPD8380	Approved

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