NPASS Compound

Natural Product: NPC164165

Natural Product ID	NPC164165
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ARANEVHRNOGYRH-CDEVUMFDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	9915548
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 81 86 0 0 0 0 0 0 0 0999 V2000 7.2505 -0.5755 -2.8506 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6646 -0.8873 -1.4838 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6148 -0.3991 -0.3817 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0687 -1.0616 0.8896 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5727 -1.0570 0.9156 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9214 -0.1927 -0.1025 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5100 -0.1847 -1.3454 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5926 -0.5642 -0.2949 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7377 0.4853 -0.0154 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8617 0.0914 1.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8697 1.1798 1.3818 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0079 1.4507 0.1552 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0915 2.8733 -0.2155 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8483 3.6305 -0.1860 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5067 0.5771 -0.9751 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3510 0.6187 -2.1853 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6492 1.3146 -2.0527 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3161 1.2847 -0.7209 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3966 1.0354 0.4504 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5015 -0.3890 0.9246 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8748 -0.6087 1.4664 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9914 -0.0481 0.6359 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6494 1.0677 1.4440 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9329 -1.1841 0.3335 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3589 -0.9081 0.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0556 -1.5867 1.5692 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4131 -1.0918 1.6504 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2797 -1.5584 2.4394 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5147 -0.0751 0.7337 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2847 0.0677 0.0797 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7445 -1.5462 -1.1232 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5906 -0.7033 -1.6416 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5785 0.4589 -0.6983 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6492 1.2768 -1.1573 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3999 -2.8824 -1.3184 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9488 0.9096 -1.2316 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1717 -0.6767 2.1954 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6362 -0.3839 1.9572 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9100 -0.8139 -0.5941 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6103 0.4749 -2.8594 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0697 -1.2745 -3.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4284 -0.7372 -3.5900 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5065 -1.9610 -1.3486 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5083 0.6986 -0.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4926 -2.0877 0.8883 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2286 -2.1047 0.7813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9117 0.8639 0.2366 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3170 1.3881 0.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5497 0.1037 2.0435 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4788 -0.9247 1.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2772 1.0905 2.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4920 2.1201 1.5375 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0400 3.3350 -0.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4945 -0.4909 -0.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2506 1.1400 -2.9897 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4810 -0.4154 -2.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5429 2.3562 -2.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3388 0.8335 -2.8156 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6874 2.3474 -0.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7136 1.6585 1.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7635 -0.5138 1.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2542 -1.1530 0.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9779 -1.7232 1.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9022 -0.1891 2.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8519 1.9403 0.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5171 0.7296 2.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9216 1.4298 2.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6150 -2.1248 0.8846 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6405 -2.4072 2.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4227 -0.0526 -1.0218 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9949 1.1335 0.2030 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6810 -1.3939 -1.7083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6860 -1.3013 -1.6879 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9346 -0.3934 -2.6779 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4286 1.6288 -2.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9669 -3.4087 -0.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2818 0.2569 -2.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1412 1.9354 -1.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8619 -0.8457 2.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5084 -0.7107 2.2288 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3166 -0.1952 -1.2805 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 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 2 0 12 15 1 0 15 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 1 0 22 23 1 0 22 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 24 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 31 35 1 0 15 36 1 0 5 37 1 0 4 38 1 0 3 39 1 0 7 2 1 0 36 9 1 0 19 12 1 0 33 22 1 0 33 18 1 0 30 25 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 6 3 44 1 1 4 45 1 6 5 46 1 6 6 47 1 1 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 13 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 26 69 1 0 30 70 1 0 30 71 1 0 31 72 1 0 32 73 1 0 32 74 1 0 34 75 1 0 35 76 1 0 36 77 1 0 36 78 1 0 37 79 1 0 38 80 1 0 39 81 1 0 M END

Standard InCHIKey	ARANEVHRNOGYRH-CDEVUMFDSA-N
Standard InCHI	InChI=1S/C29H42O10/c1-14-23(33)24(34)25(35)26(38-14)39-17-5-8-28(13-30)16(10-17)3-4-19-18(28)6-7-27(2)22(15-9-21(32)37-12-15)20(31)11-29(19,27)36/h9,13-14,16-20,22-26,31,33-36H,3-8,10-12H2,1-2H3/t14-,16?,17?,18?,19?,20?,22?,23-,24+,25+,26-,27?,28?,29?/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC1CCC2(C=O)C(CCC3C2CCC2(C)C(C4=CC(=O)OC4)C(CC32O)O)C1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	550.28	Volume:	538.794 ? Van der Waals volume.
Dense:	1.021	LogP:	0.785 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.334 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.992 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	162.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.19	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.396	Fsp³:	0.862
MCE-18:	114.074 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.394	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.053 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.075	Promiscuous compounds:	0.02

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.043	MDCK Permeability:	-5.101
Pgp-inhibitor:	0.0	Pgp-substrate:	0.011
PAMPA:	0.986 ? 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):	0.869
20% Bioavailability (F20%):	0.005	30% Bioavailability (F30%):	0.721
50% Bioavailability (F50%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075	MRP1:	0.877
Plasma Protein Binding (PPB):	64.751%	Volume Distribution (VD):	-0.391
Fu:	34.443% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.433
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.0
BSEP inhibitor:	0.109

ADMET: Metabolism

CYP1A2-inhibitor:	0.071	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.017	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.26	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.151	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.002 ? 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):

1.524

Half-life (T1/2):

4.66

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.344
Human Hepatotoxicity (H-HT):	0.789	Drug-induced Liver Injury (DILI):	0.449
AMES Toxicity:	0.896	Rat Oral Acute Toxicity:	0.706
Maximum Recommended Daily Dose:	0.974	Skin Sensitization:	0.944
Carcinogencity:	0.422	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.364
Drug-induced Neurotoxicity:	0.069	Ototoxicity:	0.99
Hematotoxicity:	0.338	Drug-induced Nephrotoxicity:	0.858
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.589
A549 Cytotoxicity:	0.173	Hek293 Cytotoxicity:	0.726
BCF:	0.53 ? 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:	3.56 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.372 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.259 ? 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
NPO17873	Adonis vernalis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17873	Adonis vernalis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17873	Adonis vernalis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17873	Adonis vernalis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17873	Adonis vernalis	Species	Ranunculaceae	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 NPC164165 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	14774
0.1-0.2	30021
0.2-0.3	4527
0.3-0.4	318
0.4-0.5	99
0.5-0.6	71
0.6-0.7	35
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8267	Intermediate Similarity	NPC469750
0.7284	Intermediate Similarity	NPC179412
0.7284	Intermediate Similarity	NPC471356
0.725	Intermediate Similarity	NPC480914
0.7089	Intermediate Similarity	NPC99620
0.6829	Remote Similarity	NPC76572
0.6829	Remote Similarity	NPC193382
0.6707	Remote Similarity	NPC479356
0.6707	Remote Similarity	NPC479355
0.6707	Remote Similarity	NPC480915
0.6705	Remote Similarity	NPC231518
0.6705	Remote Similarity	NPC488944
0.6591	Remote Similarity	NPC188234
0.6588	Remote Similarity	NPC193893
0.6386	Remote Similarity	NPC196429
0.6374	Remote Similarity	NPC232785
0.6374	Remote Similarity	NPC486139
0.6353	Remote Similarity	NPC250556
0.631	Remote Similarity	NPC5311
0.631	Remote Similarity	NPC17896
0.631	Remote Similarity	NPC469755
0.631	Remote Similarity	NPC284406
0.631	Remote Similarity	NPC99080
0.631	Remote Similarity	NPC197707
0.631	Remote Similarity	NPC251866
0.6279	Remote Similarity	NPC471353
0.6277	Remote Similarity	NPC479360
0.6277	Remote Similarity	NPC479359
0.6264	Remote Similarity	NPC125077
0.6222	Remote Similarity	NPC240070
0.6129	Remote Similarity	NPC329986
0.6129	Remote Similarity	NPC140092
0.6118	Remote Similarity	NPC77299
0.6118	Remote Similarity	NPC480906
0.6071	Remote Similarity	NPC99728
0.6071	Remote Similarity	NPC87250
0.6071	Remote Similarity	NPC244402
0.6071	Remote Similarity	NPC50305
0.6064	Remote Similarity	NPC486138
0.6064	Remote Similarity	NPC276838
0.593	Remote Similarity	NPC157376
0.593	Remote Similarity	NPC142066
0.593	Remote Similarity	NPC603972
0.5862	Remote Similarity	NPC24839
0.5824	Remote Similarity	NPC30483
0.5824	Remote Similarity	NPC470897
0.5778	Remote Similarity	NPC480907
0.5761	Remote Similarity	NPC236973
0.573	Remote Similarity	NPC9499
0.573	Remote Similarity	NPC471360
0.573	Remote Similarity	NPC469751
0.573	Remote Similarity	NPC471361
0.573	Remote Similarity	NPC86159
0.573	Remote Similarity	NPC469752
0.573	Remote Similarity	NPC469754
0.573	Remote Similarity	NPC70542
0.5698	Remote Similarity	NPC471633
0.5644	Remote Similarity	NPC486150
0.5618	Remote Similarity	NPC77319
0.5618	Remote Similarity	NPC471351
0.5618	Remote Similarity	NPC471355
0.5591	Remote Similarity	NPC32177
0.5591	Remote Similarity	NPC292467
0.5591	Remote Similarity	NPC469756
0.5591	Remote Similarity	NPC275901
0.5579	Remote Similarity	NPC486143
0.5579	Remote Similarity	NPC486142
0.5579	Remote Similarity	NPC486149
0.5532	Remote Similarity	NPC480910
0.5532	Remote Similarity	NPC480909
0.5506	Remote Similarity	NPC199428
0.5506	Remote Similarity	NPC104585
0.5506	Remote Similarity	NPC109448
0.5506	Remote Similarity	NPC310341
0.5435	Remote Similarity	NPC72260
0.5417	Remote Similarity	NPC486135
0.5417	Remote Similarity	NPC486137
0.5385	Remote Similarity	NPC220217
0.5326	Remote Similarity	NPC471354
0.5326	Remote Similarity	NPC27507
0.5306	Remote Similarity	NPC486146
0.53	Remote Similarity	NPC488943
0.53	Remote Similarity	NPC488942
0.5281	Remote Similarity	NPC84987
0.5281	Remote Similarity	NPC309034
0.5269	Remote Similarity	NPC298783
0.5263	Remote Similarity	NPC27363
0.5248	Remote Similarity	NPC486144
0.5248	Remote Similarity	NPC486145
0.5248	Remote Similarity	NPC486147
0.5248	Remote Similarity	NPC486148
0.5217	Remote Similarity	NPC305574
0.5213	Remote Similarity	NPC5883
0.5204	Remote Similarity	NPC469749
0.52	Remote Similarity	NPC475219
0.5165	Remote Similarity	NPC84949
0.5165	Remote Similarity	NPC480562
0.5165	Remote Similarity	NPC74945
0.5165	Remote Similarity	NPC31354
0.5165	Remote Similarity	NPC69576
0.5158	Remote Similarity	NPC33934
0.5149	Remote Similarity	NPC488938
0.5149	Remote Similarity	NPC488937
0.5111	Remote Similarity	NPC219085
0.5104	Remote Similarity	NPC40749
0.5102	Remote Similarity	NPC208193
0.5098	Remote Similarity	NPC475590
0.5098	Remote Similarity	NPC486136
0.5053	Remote Similarity	NPC173555
0.5052	Remote Similarity	NPC32793
0.5052	Remote Similarity	NPC116075

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC164165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6091
0.1-0.2	2940
0.2-0.3	101
0.3-0.4	5
0.4-0.5	8
0.5-0.6	2
0.6-0.7	3
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
0.6705	Remote Similarity	NPD8033	Approved
0.6353	Remote Similarity	NPD7507	Pre-clinical
0.631	Remote Similarity	NPD7319	Approved
0.5435	Remote Similarity	NPD8294	Phase 4
0.5053	Remote Similarity	NPD8296	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