NPASS Compound

Natural Product: NPC514529

Natural Product ID	NPC514529
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(+)-O,O-Dimethyltubocurine
IUPAC Name	9,10,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-dodecaene
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 88 94 0 0 0 0 0 0 0 0999 V2000 -3.0524 4.6263 -1.0984 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7957 3.6893 -0.0988 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5114 3.2024 0.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4252 3.6112 -0.6086 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8220 3.0953 -0.3389 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0160 2.1648 0.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1009 1.7864 1.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3584 2.2785 1.1397 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4580 1.8506 1.9028 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4491 1.0675 1.3316 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1001 -0.0621 0.6538 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0427 -0.8581 0.0786 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3689 -0.5287 0.1755 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7502 0.6129 0.8583 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7814 1.4086 1.4357 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1220 2.5564 2.1247 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4428 3.0011 2.2951 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4495 -1.3546 -0.4390 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7966 -2.3862 -1.3293 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6856 -3.0314 -0.6591 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0718 -3.4284 0.6596 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5819 -2.0765 -0.6487 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3315 -2.6809 -0.1289 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0664 -2.1607 -0.6653 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -2.1706 0.1799 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2565 -1.6993 -0.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3827 -1.2108 -1.5419 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2965 -1.1996 -2.3700 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9099 -1.6717 -1.9274 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6471 -0.7524 -1.9041 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7280 -0.8133 -1.0486 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5173 -1.9350 -1.0148 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1840 -2.9963 -1.8789 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3284 -4.0477 -1.5453 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6092 -2.0657 -0.1809 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3548 -3.2456 -0.2148 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4724 -3.4731 0.5863 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9268 -1.0313 0.6548 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1327 0.1101 0.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0445 0.2124 -0.2206 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3018 1.5300 -0.1530 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3521 1.5855 0.9964 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3535 2.4852 -0.0935 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5509 3.3723 -1.1598 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1621 2.5463 1.0437 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5088 1.1944 1.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8371 5.6681 -0.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1645 4.6152 -1.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5301 4.4001 -2.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5401 4.3444 -1.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6930 3.4221 -0.9314 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0290 1.0635 2.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0601 -0.3134 0.5802 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7951 0.8996 0.9510 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5012 4.0585 2.5773 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9561 2.9021 1.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9854 2.4044 3.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0593 -0.6655 -1.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1332 -1.7979 0.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4602 -1.8983 -2.2551 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5213 -3.1716 -1.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1514 -3.7463 0.6257 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9896 -2.6490 1.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5298 -4.3231 1.0317 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4554 -1.7736 -1.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3674 -3.7941 -0.3557 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3085 -2.6870 1.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0515 -2.5624 1.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0884 -1.7341 0.4429 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3877 -0.8229 -3.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7389 -1.6445 -2.6250 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9922 -4.0581 -0.5036 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4513 -4.1203 -2.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8987 -5.0081 -1.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2510 -3.6409 1.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1749 -2.6275 0.4593 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0107 -4.3661 0.1544 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7812 -1.1186 1.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7311 1.6871 -1.0897 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7569 2.2059 1.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2009 0.5757 1.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9364 4.3011 -1.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3691 2.8421 -2.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6491 3.6393 -1.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0832 3.1344 0.7843 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6422 3.0867 1.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6220 1.1697 1.7232 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0442 0.9956 2.5757 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 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 13 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 27 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 35 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 8 3 1 0 15 10 1 0 29 24 1 0 40 31 1 0 42 6 1 0 22 12 1 0 46 39 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 0 5 51 1 0 7 52 1 0 11 53 1 0 14 54 1 0 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 21 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 25 68 1 0 26 69 1 0 28 70 1 0 29 71 1 0 34 72 1 0 34 73 1 0 34 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 38 78 1 0 41 79 1 0 42 80 1 0 42 81 1 0 44 82 1 0 44 83 1 0 44 84 1 0 45 85 1 0 45 86 1 0 46 87 1 0 46 88 1 0 M END

Standard InCHIKey	BWFWPNFEEDTSFC-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-38-36-26(21-35(43-5)37(38)44-6)14-16-40(2)30(36)18-24-9-12-31(41-3)33(19-24)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3
SMILES	COC1=CC=C2C=C1OC1=CC3=C(C=C1OC)CCN(C)C3CC1=CC=C(C=C1)OC1=C(OC)C(OC)=CC3=C1C(C2)N(C)CC3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.3	Volume:	649.006 ? Van der Waals volume.
Dense:	0.959	LogP:	3.716 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.455 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.749 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	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:	0.238	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.73	Fsp³:	0.368
MCE-18:	129.0 ? 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:	0.993	Fluc inhibitor:	0.036 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.593 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.849 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.33

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.628	MDCK Permeability:	-4.719
Pgp-inhibitor:	0.885	Pgp-substrate:	0.298
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%):	0.02	30% Bioavailability (F30%):	0.012
50% Bioavailability (F50%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997	MRP1:	0.99
Plasma Protein Binding (PPB):	71.56%	Volume Distribution (VD):	0.171
Fu:	26.657% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.082
OATP1B3 inhibitor:	0.953	BCRP inhibitor:	0.841
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.991	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.108
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.142 ? 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):

8.261

Half-life (T1/2):

2.828

ADMET: Toxicity

hERG Blockers:	0.934	hERG Blockers (10um):	0.886
Human Hepatotoxicity (H-HT):	0.355	Drug-induced Liver Injury (DILI):	0.003
AMES Toxicity:	0.642	Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.917	Skin Sensitization:	0.931
Carcinogencity:	0.844	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.948
Drug-induced Neurotoxicity:	0.619	Ototoxicity:	0.889
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.051
Genotoxicity:	0.057	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.145	Hek293 Cytotoxicity:	0.799
BCF:	2.234 ? 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:	4.492 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.011 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.353 ? 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
NPO46703	Paraquilegia anemonoides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC514529 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	34197
0.1-0.2	14917
0.2-0.3	495
0.3-0.4	114
0.4-0.5	30
0.5-0.6	40
0.6-0.7	27
0.7-0.8	1
0.8-0.85	5
0.85-0.9	1
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC76682
0.9355	High Similarity	NPC10908
0.9355	High Similarity	NPC63646
0.9355	High Similarity	NPC317145
0.9355	High Similarity	NPC198498
0.9355	High Similarity	NPC115284
0.9231	High Similarity	NPC480587
0.8906	High Similarity	NPC276890
0.8116	Intermediate Similarity	NPC73492
0.8116	Intermediate Similarity	NPC299990
0.8028	Intermediate Similarity	NPC223690
0.8028	Intermediate Similarity	NPC9532
0.8	Intermediate Similarity	NPC317439
0.7941	Intermediate Similarity	NPC227060
0.7887	Intermediate Similarity	NPC239824
0.7826	Intermediate Similarity	NPC12424
0.7826	Intermediate Similarity	NPC129518
0.7826	Intermediate Similarity	NPC251580
0.7778	Intermediate Similarity	NPC185639
0.7778	Intermediate Similarity	NPC251735
0.7778	Intermediate Similarity	NPC49075
0.7778	Intermediate Similarity	NPC599951
0.7714	Intermediate Similarity	NPC603853
0.7619	Intermediate Similarity	NPC247639
0.7619	Intermediate Similarity	NPC25084
0.75	Intermediate Similarity	NPC279228
0.7397	Intermediate Similarity	NPC311973
0.7361	Intermediate Similarity	NPC290582
0.7361	Intermediate Similarity	NPC217748
0.7361	Intermediate Similarity	NPC182052
0.7361	Intermediate Similarity	NPC271013
0.7361	Intermediate Similarity	NPC42663
0.7361	Intermediate Similarity	NPC15414
0.7297	Intermediate Similarity	NPC116465
0.7	Intermediate Similarity	NPC480586
0.6842	Remote Similarity	NPC254441
0.6835	Remote Similarity	NPC24260
0.6806	Remote Similarity	NPC41376
0.679	Remote Similarity	NPC480590
0.6709	Remote Similarity	NPC475479
0.6709	Remote Similarity	NPC323537
0.6625	Remote Similarity	NPC485712
0.6582	Remote Similarity	NPC16357
0.6582	Remote Similarity	NPC302245
0.6582	Remote Similarity	NPC195538
0.6538	Remote Similarity	NPC229373
0.65	Remote Similarity	NPC212237
0.65	Remote Similarity	NPC243454
0.6486	Remote Similarity	NPC603603
0.642	Remote Similarity	NPC611658
0.6329	Remote Similarity	NPC274716
0.6329	Remote Similarity	NPC167116
0.6329	Remote Similarity	NPC609821
0.6265	Remote Similarity	NPC10871
0.625	Remote Similarity	NPC181796
0.625	Remote Similarity	NPC290005
0.625	Remote Similarity	NPC54654
0.625	Remote Similarity	NPC7715
0.625	Remote Similarity	NPC328155
0.625	Remote Similarity	NPC222661
0.625	Remote Similarity	NPC285931
0.6092	Remote Similarity	NPC475597
0.5938	Remote Similarity	NPC213206
0.5938	Remote Similarity	NPC188163
0.5938	Remote Similarity	NPC328750
0.593	Remote Similarity	NPC206900
0.593	Remote Similarity	NPC281581
0.589	Remote Similarity	NPC317272
0.589	Remote Similarity	NPC268503
0.5875	Remote Similarity	NPC475393
0.5867	Remote Similarity	NPC256012
0.5867	Remote Similarity	NPC610965
0.5862	Remote Similarity	NPC485711
0.5811	Remote Similarity	NPC30779
0.5781	Remote Similarity	NPC314682
0.5698	Remote Similarity	NPC239584
0.5696	Remote Similarity	NPC480591
0.5679	Remote Similarity	NPC286119
0.5679	Remote Similarity	NPC112248
0.5647	Remote Similarity	NPC249996
0.5568	Remote Similarity	NPC82457
0.5556	Remote Similarity	NPC41122
0.5556	Remote Similarity	NPC318805
0.5556	Remote Similarity	NPC608819
0.5465	Remote Similarity	NPC8836
0.5417	Remote Similarity	NPC104196
0.5412	Remote Similarity	NPC302275
0.5393	Remote Similarity	NPC11296
0.5393	Remote Similarity	NPC274661
0.5385	Remote Similarity	NPC480592
0.5375	Remote Similarity	NPC240841
0.5349	Remote Similarity	NPC139783
0.5349	Remote Similarity	NPC65312
0.5349	Remote Similarity	NPC611798
0.5287	Remote Similarity	NPC275680
0.5287	Remote Similarity	NPC22115
0.5185	Remote Similarity	NPC610959
0.5161	Remote Similarity	NPC234318
0.5155	Remote Similarity	NPC475654
0.5119	Remote Similarity	NPC600054
0.5119	Remote Similarity	NPC601504
0.5055	Remote Similarity	NPC254581

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC514529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5071
0.1-0.2	3949
0.2-0.3	116
0.3-0.4	6
0.4-0.5	3
0.5-0.6	2
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
0.9355	High Similarity	NPD8099	Discontinued
0.8507	High Similarity	NPD8156	Discontinued
0.7606	Intermediate Similarity	NPD8095	Phase 1
0.5938	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5326	Remote Similarity	NPD8053	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