NPASS Compound

Natural Product: NPC518500

Natural Product ID	NPC518500
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	9,21,25-trimethoxy-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-dodecaen-10-ol
IUPAC Name	9,21,25-trimethoxy-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-dodecaen-10-ol
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 85 91 0 0 0 0 0 0 0 0999 V2000 -2.0244 4.1346 -2.8051 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9361 3.5615 -1.5365 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7482 3.0964 -0.9657 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4556 3.1703 -1.6293 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5964 2.6747 -0.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5322 2.1425 0.2662 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2944 2.0937 0.8865 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8321 2.5560 0.2992 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0382 2.4970 0.9375 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0229 1.5513 0.7774 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8203 0.2108 0.9607 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8375 -0.7122 0.7925 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0680 -0.2113 0.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3058 1.1570 0.2354 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2781 2.0433 0.4093 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4616 3.3953 0.2294 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6636 3.9995 -0.1359 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2409 -1.1138 0.2543 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7253 -2.4894 -0.0729 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8500 -2.8682 1.0142 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6525 -4.3114 0.9021 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5999 -2.1578 0.9997 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7170 -2.8212 0.0029 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3783 -2.2242 -0.1739 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3551 -2.5062 0.6938 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8782 -1.9032 0.4554 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0673 -1.0595 -0.6044 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0348 -0.7947 -1.4541 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1901 -1.3733 -1.2450 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2813 -0.4797 -0.8163 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5151 -0.8549 -0.3600 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8828 -2.1718 -0.4948 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0152 -3.1130 -1.0845 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0742 -3.3279 -2.4935 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1013 -2.6513 -0.0707 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4137 -4.0205 -0.2410 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9932 -1.7917 0.5109 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6050 -0.4465 0.6430 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4066 0.0342 0.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9734 1.4640 0.3631 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6650 1.6017 1.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9417 2.2292 1.1064 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7830 2.1382 2.5227 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3045 1.8700 0.7571 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6043 0.4985 1.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9566 4.7612 -2.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1380 3.3305 -3.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1442 4.7409 -3.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5109 3.5920 -2.6119 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 2.7643 -1.5436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2054 1.6648 1.8978 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8563 -0.1453 1.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3047 1.5052 -0.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4552 3.6782 0.6028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9686 3.6991 -1.1446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5616 5.1054 -0.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7456 -1.1619 1.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9310 -0.7113 -0.5178 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1199 -2.4291 -0.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5573 -3.2247 -0.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9944 -4.7163 1.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6600 -4.7703 1.0413 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3419 -4.5883 -0.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1329 -2.2297 2.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5165 -3.8538 0.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2331 -2.9386 -0.9692 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4292 -3.1571 1.5452 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7243 -2.0899 1.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1721 -0.1336 -2.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9961 -1.1486 -1.9325 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0717 -3.7210 -2.7778 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7938 -4.1393 -2.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2474 -2.4142 -3.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1638 -4.2896 -0.8712 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9484 -2.1088 0.8564 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9421 1.9363 -0.6495 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3800 0.6132 1.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7288 2.2724 1.9531 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2751 3.0561 2.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2359 1.2085 2.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7607 2.1212 3.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9623 2.5951 1.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5110 1.9697 -0.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6153 0.4369 2.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6071 0.2044 0.8981 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 35 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 8 3 1 0 15 10 1 0 29 24 1 0 39 31 1 0 41 6 1 0 22 12 1 0 45 38 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 5 50 1 0 7 51 1 0 11 52 1 0 14 53 1 0 17 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 25 67 1 0 26 68 1 0 28 69 1 0 29 70 1 0 34 71 1 0 34 72 1 0 34 73 1 0 36 74 1 0 37 75 1 0 40 76 1 0 41 77 1 0 41 78 1 0 43 79 1 0 43 80 1 0 43 81 1 0 44 82 1 0 44 83 1 0 45 84 1 0 45 85 1 0 M END

Standard InCHIKey	DQFIZQYILFTDPW-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C37H40N2O6/c1-38-14-12-24-20-32(42-4)34-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(19-30(40)36(37)43-5)13-15-39(2)29(35)17-23-8-11-31(41-3)33(18-23)45-34/h6-11,18-21,28-29,40H,12-17H2,1-5H3
SMILES	COC1=CC=C2C=C1OC1=CC3=C(C=C1OC)CCN(C)C3CC1=CC=C(C=C1)OC1=C(OC)C(O)=CC3=C1C(C2)N(C)CC3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.29	Volume:	631.71 ? Van der Waals volume.
Dense:	0.963	LogP:	3.344 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.176 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.216 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	42.0
TPSA:	72.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	8.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.271	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.783	Fsp³:	0.351
MCE-18:	129.48 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.997	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.722 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.908 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.161

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.82	MDCK Permeability:	-4.765
Pgp-inhibitor:	0.407	Pgp-substrate:	0.626
PAMPA:	0.01 ? 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%):	0.057	30% Bioavailability (F30%):	0.056
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997	MRP1:	0.992
Plasma Protein Binding (PPB):	69.787%	Volume Distribution (VD):	-0.113
Fu:	30.815% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.174
OATP1B3 inhibitor:	0.95	BCRP inhibitor:	0.699
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.279
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.025
CYP2B6-substrate:	0.995	CYP2C8-inhibitor:	0.001
HLM stability:	0.069 ? 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):

7.423

Half-life (T1/2):

2.543

ADMET: Toxicity

hERG Blockers:	0.911	hERG Blockers (10um):	0.879
Human Hepatotoxicity (H-HT):	0.339	Drug-induced Liver Injury (DILI):	0.002
AMES Toxicity:	0.672	Rat Oral Acute Toxicity:	0.536
Maximum Recommended Daily Dose:	0.916	Skin Sensitization:	0.958
Carcinogencity:	0.8	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.957
Drug-induced Neurotoxicity:	0.454	Ototoxicity:	0.872
Hematotoxicity:	0.039	Drug-induced Nephrotoxicity:	0.048
Genotoxicity:	0.075	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.191	Hek293 Cytotoxicity:	0.816
BCF:	1.781 ? 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:	4.377 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.709 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.016 ? 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
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[20593839]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18410	Cyclea racemosa	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 NPC518500 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	28524
0.1-0.2	19758
0.2-0.3	1308
0.3-0.4	125
0.4-0.5	31
0.5-0.6	49
0.6-0.7	36
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239824
0.942	High Similarity	NPC311973
0.7763	Intermediate Similarity	NPC254441
0.75	Intermediate Similarity	NPC279228
0.7397	Intermediate Similarity	NPC76682
0.7397	Intermediate Similarity	NPC10908
0.7397	Intermediate Similarity	NPC63646
0.7397	Intermediate Similarity	NPC317145
0.7397	Intermediate Similarity	NPC198498
0.7397	Intermediate Similarity	NPC115284
0.7368	Intermediate Similarity	NPC290582
0.7368	Intermediate Similarity	NPC217748
0.7368	Intermediate Similarity	NPC182052
0.7368	Intermediate Similarity	NPC271013
0.7368	Intermediate Similarity	NPC42663
0.7368	Intermediate Similarity	NPC15414
0.7368	Intermediate Similarity	NPC480587
0.7308	Intermediate Similarity	NPC116465
0.7308	Intermediate Similarity	NPC223690
0.7308	Intermediate Similarity	NPC9532
0.72	Intermediate Similarity	NPC603603
0.7089	Intermediate Similarity	NPC185639
0.7089	Intermediate Similarity	NPC251735
0.7089	Intermediate Similarity	NPC49075
0.7089	Intermediate Similarity	NPC599951
0.7067	Intermediate Similarity	NPC276890
0.6923	Remote Similarity	NPC73492
0.6923	Remote Similarity	NPC299990
0.6883	Remote Similarity	NPC12424
0.6883	Remote Similarity	NPC129518
0.6883	Remote Similarity	NPC251580
0.6857	Remote Similarity	NPC247639
0.6857	Remote Similarity	NPC25084
0.6795	Remote Similarity	NPC603853
0.6667	Remote Similarity	NPC24260
0.6667	Remote Similarity	NPC611658
0.6548	Remote Similarity	NPC212237
0.6543	Remote Similarity	NPC286119
0.6506	Remote Similarity	NPC181796
0.6506	Remote Similarity	NPC290005
0.6506	Remote Similarity	NPC54654
0.6506	Remote Similarity	NPC7715
0.6506	Remote Similarity	NPC328155
0.6506	Remote Similarity	NPC222661
0.6506	Remote Similarity	NPC285931
0.6437	Remote Similarity	NPC480586
0.642	Remote Similarity	NPC608819
0.6386	Remote Similarity	NPC274716
0.6386	Remote Similarity	NPC229373
0.6386	Remote Similarity	NPC167116
0.6386	Remote Similarity	NPC609821
0.6329	Remote Similarity	NPC227060
0.6197	Remote Similarity	NPC317439
0.6184	Remote Similarity	NPC317272
0.6184	Remote Similarity	NPC268503
0.6154	Remote Similarity	NPC256012
0.6154	Remote Similarity	NPC610965
0.6104	Remote Similarity	NPC30779
0.6076	Remote Similarity	NPC480592
0.6067	Remote Similarity	NPC480590
0.6049	Remote Similarity	NPC240841
0.6	Remote Similarity	NPC41376
0.5862	Remote Similarity	NPC16357
0.5862	Remote Similarity	NPC302245
0.5854	Remote Similarity	NPC610959
0.5824	Remote Similarity	NPC82457
0.5753	Remote Similarity	NPC135538
0.5753	Remote Similarity	NPC24233
0.5682	Remote Similarity	NPC195538
0.5652	Remote Similarity	NPC206900
0.5618	Remote Similarity	NPC243454
0.5581	Remote Similarity	NPC600872
0.5556	Remote Similarity	NPC8836
0.5556	Remote Similarity	NPC485712
0.5526	Remote Similarity	NPC104196
0.5484	Remote Similarity	NPC11296
0.5484	Remote Similarity	NPC274661
0.5474	Remote Similarity	NPC475597
0.5474	Remote Similarity	NPC41122
0.5474	Remote Similarity	NPC318805
0.5444	Remote Similarity	NPC475479
0.5444	Remote Similarity	NPC323537
0.5444	Remote Similarity	NPC601489
0.5444	Remote Similarity	NPC604804
0.5412	Remote Similarity	NPC480591
0.5402	Remote Similarity	NPC475393
0.5402	Remote Similarity	NPC600054
0.5402	Remote Similarity	NPC601504
0.5385	Remote Similarity	NPC275680
0.5385	Remote Similarity	NPC22115
0.5352	Remote Similarity	NPC213206
0.5352	Remote Similarity	NPC188163
0.5352	Remote Similarity	NPC328750
0.5275	Remote Similarity	NPC139783
0.5275	Remote Similarity	NPC65312
0.5275	Remote Similarity	NPC611798
0.5269	Remote Similarity	NPC10871
0.5269	Remote Similarity	NPC239584
0.5263	Remote Similarity	NPC485711
0.5248	Remote Similarity	NPC475654
0.5211	Remote Similarity	NPC314682
0.52	Remote Similarity	NPC147390
0.52	Remote Similarity	NPC428
0.5169	Remote Similarity	NPC601503
0.5158	Remote Similarity	NPC281581
0.5135	Remote Similarity	NPC185838
0.5102	Remote Similarity	NPC48490
0.5056	Remote Similarity	NPC112248
0.5054	Remote Similarity	NPC249996
0.5054	Remote Similarity	NPC605743
0.5051	Remote Similarity	NPC201508

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC518500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4685
0.1-0.2	4359
0.2-0.3	91
0.3-0.4	8
0.4-0.5	1
0.5-0.6	3
0.6-0.7	1
0.7-0.8	2
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
0.7397	Intermediate Similarity	NPD8099	Discontinued
0.7013	Intermediate Similarity	NPD8156	Discontinued
0.6709	Remote Similarity	NPD8095	Phase 1
0.5579	Remote Similarity	NPD8053	Approved
0.5352	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5204	Remote Similarity	NPD8054	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