NPASS Compound

Natural Product: NPC225156

Natural Product ID	NPC225156
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZVVVPJJQRQNTAT-URLMMPGGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46173762
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 82 88 0 0 0 0 0 0 0 0999 V2000 5.4511 0.4787 1.8117 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3059 1.1252 1.1990 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6774 2.3700 0.5907 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7282 2.3024 -0.9326 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3058 2.0192 -1.3304 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6408 2.7330 -2.2720 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3349 2.4044 -2.5393 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6727 1.3636 -1.8742 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4080 0.6623 -0.9152 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6976 0.9601 -0.6282 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5243 0.2399 0.3561 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7997 -0.7201 1.2417 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9700 -2.1544 0.8745 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1909 -2.6949 0.5692 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3197 -4.0498 0.2406 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1580 -4.8424 0.2325 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9475 -4.3112 0.5337 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8573 -2.9742 0.8526 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7916 -5.0982 0.5238 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4413 -4.4163 0.4237 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0182 -3.9774 1.5732 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2141 -3.2952 1.5027 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8476 -3.0404 0.3012 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2317 -3.5068 -0.8320 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0375 -4.1918 -0.7935 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0671 -2.2681 0.2595 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1389 -0.8827 0.6564 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3763 0.1701 -0.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3143 0.0776 -0.8524 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7170 1.2049 -1.3621 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1924 2.4653 -1.0467 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2826 2.6056 -0.2103 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8547 1.4625 0.2790 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0575 1.5036 1.1658 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8380 0.6178 2.3351 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0103 -0.5541 2.0726 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6469 -0.2049 2.4207 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8054 3.8401 0.1420 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8269 4.4201 -0.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6179 3.6470 -1.5387 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6316 1.1046 -2.2019 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3256 -6.1855 -0.0989 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6276 3.1085 -3.4951 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2396 4.1694 -4.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9870 1.3121 2.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0997 -0.2477 2.5417 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0830 0.0587 1.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6986 2.6288 0.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9948 3.1809 0.9073 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4197 1.5227 -1.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0330 3.3089 -1.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1417 3.5442 -2.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8601 -0.1300 -0.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3026 -0.3679 -0.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7303 -0.4539 1.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1560 -0.6407 2.3156 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0617 -2.0579 0.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2908 -4.4586 0.0028 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -2.5073 1.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5607 -4.1532 2.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6506 -2.9822 2.4559 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6980 -3.3313 -1.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5681 -4.5492 -1.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4571 -2.3310 -0.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9033 -2.8209 0.8110 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2355 -0.6066 0.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8961 -0.8554 -1.1355 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1501 2.5571 1.5647 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9863 1.2401 0.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8153 0.2409 2.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3919 1.2059 3.1627 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4224 -0.6724 3.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6048 0.8896 2.5712 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9175 -0.4230 1.6215 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8012 3.8698 -0.5401 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9891 5.4661 -0.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5778 4.3833 -1.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9269 4.0581 -2.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8132 -6.8973 0.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3986 5.0330 -3.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5592 4.4579 -5.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2166 3.8412 -4.6303 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 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 17 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 26 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 1 0 34 35 1 0 35 36 1 0 36 37 1 0 32 38 1 0 38 39 1 0 31 40 1 0 30 41 1 0 16 42 1 0 7 43 1 0 43 44 1 0 11 2 1 0 18 13 2 0 25 20 1 0 36 27 1 0 10 5 1 0 33 28 2 0 41 8 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 6 52 1 0 9 53 1 0 11 54 1 6 12 55 1 0 12 56 1 0 14 57 1 0 15 58 1 0 18 59 1 0 21 60 1 0 22 61 1 0 24 62 1 0 25 63 1 0 26 64 1 0 26 65 1 0 27 66 1 6 29 67 1 0 34 68 1 0 34 69 1 0 35 70 1 0 35 71 1 0 37 72 1 0 37 73 1 0 37 74 1 0 39 75 1 0 39 76 1 0 39 77 1 0 40 78 1 0 42 79 1 0 44 80 1 0 44 81 1 0 44 82 1 0 M END

Standard InCHIKey	ZVVVPJJQRQNTAT-URLMMPGGSA-N
Standard InCHI	InChI=1S/C36H38N2O6/c1-37-13-11-23-18-32(41-3)33-19-26(23)28(37)16-22-7-10-30(39)31(17-22)43-24-8-5-21(6-9-24)15-29-27-20-34(44-33)35(40)36(42-4)25(27)12-14-38(29)2/h5-10,17-20,28-29,39-40H,11-16H2,1-4H3/t28-,29+/m0/s1
SMILES	CN1CCc2cc(c3cc2[C@@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@@H]1c2cc(c(c(c2CCN1C)OC)O)O3)O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.27	Volume:	614.414 ? Van der Waals volume.
Dense:	0.967	LogP:	3.092 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.754 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.909 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	42.0
TPSA:	83.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	2.0	Rings:	8.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.27	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.988	Fsp³:	0.333
MCE-18:	130.0 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.995	Fluc inhibitor:	0.016 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.862 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.959 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.198

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.21	MDCK Permeability:	-4.898
Pgp-inhibitor:	0.207	Pgp-substrate:	0.847
PAMPA:	0.003 ? 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%):	0.922	30% Bioavailability (F30%):	0.835
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965	MRP1:	0.993
Plasma Protein Binding (PPB):	72.939%	Volume Distribution (VD):	-0.153
Fu:	29.913% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.883
OATP1B3 inhibitor:	0.897	BCRP inhibitor:	0.669
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.044
CYP2B6-substrate:	0.979	CYP2C8-inhibitor:	0.001
HLM stability:	0.014 ? 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):

12.313

Half-life (T1/2):

2.448

ADMET: Toxicity

hERG Blockers:	0.832	hERG Blockers (10um):	0.853
Human Hepatotoxicity (H-HT):	0.421	Drug-induced Liver Injury (DILI):	0.005
AMES Toxicity:	0.639	Rat Oral Acute Toxicity:	0.886
Maximum Recommended Daily Dose:	0.986	Skin Sensitization:	0.5
Carcinogencity:	0.697	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.944
Drug-induced Neurotoxicity:	0.84	Ototoxicity:	0.231
Hematotoxicity:	0.032	Drug-induced Nephrotoxicity:	0.313
Genotoxicity:	0.962	RPMI-8226 Immunitoxicity:	0.072
A549 Cytotoxicity:	0.355	Hek293 Cytotoxicity:	0.609
BCF:	1.621 ? 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:	4.358 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.483 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.876 ? 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
NPO547	Thalictrum lucidum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO547	Thalictrum lucidum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO547	Thalictrum lucidum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO547	Thalictrum lucidum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO547	Thalictrum lucidum	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 NPC225156 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	28981
0.1-0.2	19368
0.2-0.3	1236
0.3-0.4	137
0.4-0.5	44
0.5-0.6	43
0.6-0.7	26
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
0.7606	Intermediate Similarity	NPC317272
0.7606	Intermediate Similarity	NPC268503
0.7534	Intermediate Similarity	NPC256012
0.7534	Intermediate Similarity	NPC610965
0.7407	Intermediate Similarity	NPC212237
0.7375	Intermediate Similarity	NPC181796
0.7375	Intermediate Similarity	NPC290005
0.7375	Intermediate Similarity	NPC54654
0.7375	Intermediate Similarity	NPC7715
0.7375	Intermediate Similarity	NPC328155
0.7375	Intermediate Similarity	NPC222661
0.7375	Intermediate Similarity	NPC285931
0.7342	Intermediate Similarity	NPC185639
0.7342	Intermediate Similarity	NPC251735
0.7342	Intermediate Similarity	NPC49075
0.7342	Intermediate Similarity	NPC223690
0.7342	Intermediate Similarity	NPC9532
0.7342	Intermediate Similarity	NPC599951
0.7108	Intermediate Similarity	NPC611658
0.6923	Remote Similarity	NPC240841
0.6905	Remote Similarity	NPC24260
0.6829	Remote Similarity	NPC274716
0.6829	Remote Similarity	NPC167116
0.6829	Remote Similarity	NPC609821
0.6709	Remote Similarity	NPC610959
0.6329	Remote Similarity	NPC480592
0.6322	Remote Similarity	NPC8836
0.631	Remote Similarity	NPC601503
0.6265	Remote Similarity	NPC608819
0.6196	Remote Similarity	NPC41122
0.6196	Remote Similarity	NPC318805
0.619	Remote Similarity	NPC600054
0.619	Remote Similarity	NPC601504
0.6145	Remote Similarity	NPC290582
0.6145	Remote Similarity	NPC217748
0.6145	Remote Similarity	NPC182052
0.6145	Remote Similarity	NPC271013
0.6145	Remote Similarity	NPC42663
0.6145	Remote Similarity	NPC15414
0.6071	Remote Similarity	NPC279228
0.6064	Remote Similarity	NPC201508
0.6	Remote Similarity	NPC247639
0.6	Remote Similarity	NPC311973
0.6	Remote Similarity	NPC239824
0.6	Remote Similarity	NPC25084
0.5976	Remote Similarity	NPC603603
0.5957	Remote Similarity	NPC60295
0.593	Remote Similarity	NPC116465
0.587	Remote Similarity	NPC206900
0.5843	Remote Similarity	NPC601489
0.5843	Remote Similarity	NPC604804
0.5833	Remote Similarity	NPC603853
0.5778	Remote Similarity	NPC605743
0.5747	Remote Similarity	NPC254441
0.5732	Remote Similarity	NPC76682
0.5732	Remote Similarity	NPC10908
0.5732	Remote Similarity	NPC63646
0.5732	Remote Similarity	NPC317145
0.5732	Remote Similarity	NPC198498
0.5732	Remote Similarity	NPC115284
0.5591	Remote Similarity	NPC480586
0.5591	Remote Similarity	NPC480590
0.5567	Remote Similarity	NPC175890
0.5506	Remote Similarity	NPC229373
0.5476	Remote Similarity	NPC276890
0.5465	Remote Similarity	NPC480591
0.5455	Remote Similarity	NPC286119
0.5412	Remote Similarity	NPC227060
0.5405	Remote Similarity	NPC185838
0.5402	Remote Similarity	NPC73492
0.5402	Remote Similarity	NPC299990
0.5402	Remote Similarity	NPC480587
0.5368	Remote Similarity	NPC82457
0.5366	Remote Similarity	NPC30779
0.5349	Remote Similarity	NPC12424
0.5349	Remote Similarity	NPC129518
0.5349	Remote Similarity	NPC251580
0.5269	Remote Similarity	NPC275680
0.5269	Remote Similarity	NPC22115
0.5217	Remote Similarity	NPC16357
0.5217	Remote Similarity	NPC302245
0.5195	Remote Similarity	NPC135538
0.5195	Remote Similarity	NPC24233
0.5152	Remote Similarity	NPC191132
0.5146	Remote Similarity	NPC475654
0.5111	Remote Similarity	NPC600872
0.5068	Remote Similarity	NPC314682
0.5051	Remote Similarity	NPC85381

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC225156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4717
0.1-0.2	4324
0.2-0.3	100
0.3-0.4	3
0.4-0.5	0
0.5-0.6	3
0.6-0.7	2
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
0.6237	Remote Similarity	NPD8054	Phase 4
0.6129	Remote Similarity	NPD8053	Approved
0.5732	Remote Similarity	NPD8099	Discontinued
0.5465	Remote Similarity	NPD8156	Discontinued
0.5402	Remote Similarity	NPD8095	Phase 1

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