NPASS Compound

Natural Product: NPC562220

Natural Product ID	NPC562220
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1~{S},9~{S})-4,5,12,13-tetramethoxy-6-[[(1~{S})-6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1~{H}-isoquinolin-7-yl]oxy]-17-methyl-17-azatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2,4,6,10,12,14-hexaene
IUPAC Name	(1~{S},9~{S})-4,5,12,13-tetramethoxy-6-[[(1~{S})-6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1~{H}-isoquinolin-7-yl]oxy]-17-methyl-17-azatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2,4,6,10,12,14-hexaene
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 95101 0 0 0 0 0 0 0 0999 V2000 6.6313 4.6095 3.3536 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4362 4.5516 2.6226 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3071 3.7105 1.5186 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3936 2.9279 1.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 2.0969 0.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1268 1.9913 -0.6902 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1348 1.1038 -1.8382 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9213 -0.3271 -1.6595 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7125 -0.8903 -1.1125 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4922 -0.2999 -0.9541 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3997 -0.9926 -0.4102 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1802 -0.3260 -0.2794 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0208 -0.7330 -0.8003 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0640 -1.1388 0.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9406 -1.0598 1.4656 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2675 -1.2161 2.1898 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1028 -0.0099 2.1531 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9136 1.0498 3.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6741 2.1823 3.0376 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4685 3.2279 3.9374 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4297 3.0964 4.8885 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6941 2.3265 2.1133 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4731 3.4806 2.1009 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5157 3.6279 1.1574 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9147 1.3063 1.2152 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1233 0.1528 1.2407 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4411 -0.8949 0.2260 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4064 -2.0021 0.2531 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2586 -1.5559 -0.5569 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3886 -1.5556 -1.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3637 -1.1524 -2.7766 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5413 -1.1689 -4.1493 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7243 -1.5780 -4.7776 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2089 -0.7525 -2.1788 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1713 -0.3432 -2.9998 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0301 0.9997 -3.4251 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9762 -2.3212 1.5751 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9645 -2.9262 2.4099 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5906 -2.2962 -0.0379 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5708 -3.0513 0.5012 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7237 -4.3829 0.8903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8264 -2.9450 -0.1824 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8548 -2.2416 -0.7108 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2098 -2.8185 -0.9403 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5581 -2.5066 -2.3804 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3255 -1.1615 -2.7892 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4546 -1.0086 -3.9232 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0851 2.7726 -0.3069 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1491 3.6328 0.7843 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4757 5.0326 2.7574 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9316 3.5576 3.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5110 5.1336 4.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3345 2.9583 1.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1204 1.4857 -0.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1307 1.2987 -2.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4156 1.4528 -2.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7441 -0.6256 -0.8906 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3220 0.7074 -1.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2072 -1.7528 1.8492 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6072 0.0044 1.6761 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0194 -1.5483 3.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1133 0.9195 3.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4061 4.0228 5.5031 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4373 2.9588 4.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6506 2.1974 5.4972 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2192 2.7672 1.2738 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1443 3.6700 0.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0383 4.5964 1.3746 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7035 1.4117 0.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5511 -0.4779 -0.7902 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4172 -1.3456 0.5020 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8324 -2.9322 -0.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3309 -1.8858 -2.3538 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0317 -2.6005 -4.4131 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5593 -0.8879 -4.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5568 -1.6117 -5.8734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5989 1.5209 -2.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0398 1.5049 -3.4072 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4194 1.0857 -4.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0792 -2.3087 3.3392 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5767 -3.9202 2.7805 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9427 -3.0876 1.9021 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5574 -4.4294 1.6188 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9266 -4.9825 -0.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1749 -4.7647 1.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9512 -3.9888 0.1238 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9645 -2.4885 -0.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1412 -3.9327 -0.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5853 -2.8668 -2.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8834 -3.1644 -2.9994 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4249 -1.3088 -3.7519 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8617 -1.6463 -4.7342 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5715 0.0474 -4.2780 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1607 2.7776 -0.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3211 4.2560 1.0913 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 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 19 22 2 0 22 23 1 0 23 24 1 0 22 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 2 0 34 35 1 0 35 36 1 0 28 37 1 0 37 38 1 0 11 39 2 0 39 40 1 0 40 41 1 0 39 42 1 0 42 43 2 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 6 48 1 0 48 49 2 0 49 3 1 0 46 8 1 0 43 9 1 0 34 13 1 0 29 14 1 0 37 16 1 0 26 17 1 0 1 50 1 0 1 51 1 0 1 52 1 0 4 53 1 0 5 54 1 0 7 55 1 0 7 56 1 0 8 57 1 1 10 58 1 0 15 59 1 0 15 60 1 0 16 61 1 1 18 62 1 0 21 63 1 0 21 64 1 0 21 65 1 0 24 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 27 70 1 0 27 71 1 0 28 72 1 6 30 73 1 0 33 74 1 0 33 75 1 0 33 76 1 0 36 77 1 0 36 78 1 0 36 79 1 0 38 80 1 0 38 81 1 0 38 82 1 0 41 83 1 0 41 84 1 0 41 85 1 0 42 86 1 0 44 87 1 0 44 88 1 0 45 89 1 0 45 90 1 0 47 91 1 0 47 92 1 0 47 93 1 0 48 94 1 0 49 95 1 0 M END

Standard InCHIKey	JWKKOPFFIUBLLQ-ZDCRTTOTSA-N
Standard InCHI	InChI=1S/C40H46N2O7/c1-41-14-13-24-17-35(45-5)37(21-27(24)31(41)15-23-9-11-26(43-3)12-10-23)49-39-30-19-33-28-20-36(46-6)34(44-4)18-25(28)16-32(42(33)2)29(30)22-38(47-7)40(39)48-8/h9-12,17-18,20-22,31-33H,13-16,19H2,1-8H3/t31-,32-,33-/m0/s1
SMILES	COC1=CC=C(C[C@H]2C3=CC(OC4=C5C[C@H]6C7=CC(OC)=C(OC)C=C7C[C@@H](C5=CC(OC)=C4OC)N6C)=C(OC)C=C3CCN2C)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.33	Volume:	692.388 ? Van der Waals volume.
Dense:	0.962	LogP:	3.369 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.227 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.717 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	37.0
TPSA:	71.09 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	7.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.176	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.757	Fsp³:	0.4
MCE-18:	133.25 ? 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:	0.983	Fluc inhibitor:	0.036 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.692 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.732 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.255

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87	MDCK Permeability:	-4.698
Pgp-inhibitor:	0.877	Pgp-substrate:	0.938
PAMPA:	0.0 ? 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):	0.002
20% Bioavailability (F20%):	0.874	30% Bioavailability (F30%):	0.843
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206	MRP1:	0.99
Plasma Protein Binding (PPB):	59.727%	Volume Distribution (VD):	0.034
Fu:	37.109% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	0.977	BCRP inhibitor:	0.96
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.027
CYP2B6-substrate:	0.771	CYP2C8-inhibitor:	0.189
HLM stability:	0.179 ? 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):

11.508

Half-life (T1/2):

2.113

ADMET: Toxicity

hERG Blockers:	0.902	hERG Blockers (10um):	0.835
Human Hepatotoxicity (H-HT):	0.779	Drug-induced Liver Injury (DILI):	0.2
AMES Toxicity:	0.681	Rat Oral Acute Toxicity:	0.606
Maximum Recommended Daily Dose:	0.993	Skin Sensitization:	0.387
Carcinogencity:	0.651	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.926
Drug-induced Neurotoxicity:	0.985	Ototoxicity:	0.817
Hematotoxicity:	0.271	Drug-induced Nephrotoxicity:	0.537
Genotoxicity:	0.933	RPMI-8226 Immunitoxicity:	0.162
A549 Cytotoxicity:	0.465	Hek293 Cytotoxicity:	0.862
BCF:	2.021 ? 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:	4.748 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.574 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.729 ? 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
NPO60114	Hernandia voyronii	Species	Hernandiaceae	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 NPC562220 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	35286
0.1-0.2	13843
0.2-0.3	484
0.3-0.4	116
0.4-0.5	54
0.5-0.6	53
0.6-0.7	13
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
0.6613	Remote Similarity	NPC314682
0.6486	Remote Similarity	NPC76682
0.6486	Remote Similarity	NPC10908
0.6486	Remote Similarity	NPC63646
0.6486	Remote Similarity	NPC317145
0.6486	Remote Similarity	NPC198498
0.6486	Remote Similarity	NPC115284
0.64	Remote Similarity	NPC276890
0.6377	Remote Similarity	NPC247639
0.6377	Remote Similarity	NPC25084
0.6351	Remote Similarity	NPC256012
0.6351	Remote Similarity	NPC610965
0.6104	Remote Similarity	NPC227060
0.5949	Remote Similarity	NPC603853
0.5875	Remote Similarity	NPC480587
0.5854	Remote Similarity	NPC185639
0.5854	Remote Similarity	NPC251735
0.5854	Remote Similarity	NPC49075
0.5854	Remote Similarity	NPC599951
0.5758	Remote Similarity	NPC213206
0.5758	Remote Similarity	NPC188163
0.5758	Remote Similarity	NPC328750
0.575	Remote Similarity	NPC480591
0.5732	Remote Similarity	NPC600054
0.5732	Remote Similarity	NPC601504
0.5679	Remote Similarity	NPC73492
0.5679	Remote Similarity	NPC299990
0.5663	Remote Similarity	NPC223690
0.5663	Remote Similarity	NPC9532
0.5625	Remote Similarity	NPC12424
0.5625	Remote Similarity	NPC129518
0.5625	Remote Similarity	NPC251580
0.5595	Remote Similarity	NPC229373
0.5581	Remote Similarity	NPC243454
0.5542	Remote Similarity	NPC311973
0.55	Remote Similarity	NPC603603
0.5493	Remote Similarity	NPC317439
0.5488	Remote Similarity	NPC290582
0.5488	Remote Similarity	NPC217748
0.5488	Remote Similarity	NPC182052
0.5488	Remote Similarity	NPC271013
0.5488	Remote Similarity	NPC42663
0.5488	Remote Similarity	NPC15414
0.5476	Remote Similarity	NPC116465
0.5465	Remote Similarity	NPC16357
0.5465	Remote Similarity	NPC302245
0.5465	Remote Similarity	NPC195538
0.5422	Remote Similarity	NPC279228
0.5402	Remote Similarity	NPC212237
0.5357	Remote Similarity	NPC239824
0.5333	Remote Similarity	NPC480586
0.5333	Remote Similarity	NPC480590
0.5325	Remote Similarity	NPC317272
0.5325	Remote Similarity	NPC268503
0.5294	Remote Similarity	NPC601503
0.5286	Remote Similarity	NPC185838
0.5278	Remote Similarity	NPC135538
0.5278	Remote Similarity	NPC24233
0.5227	Remote Similarity	NPC601489
0.5227	Remote Similarity	NPC604804
0.5176	Remote Similarity	NPC112248
0.5169	Remote Similarity	NPC24260
0.5169	Remote Similarity	NPC605743
0.5169	Remote Similarity	NPC611658
0.5116	Remote Similarity	NPC254441
0.5114	Remote Similarity	NPC302275

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC562220 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5160
0.1-0.2	3837
0.2-0.3	139
0.3-0.4	6
0.4-0.5	4
0.5-0.6	3
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
0.6486	Remote Similarity	NPD8099	Discontinued
0.5949	Remote Similarity	NPD8156	Discontinued
0.5875	Remote Similarity	NPD8095	Phase 1
0.5758	Remote Similarity	NPD4664	Clinical (unspecified phase)

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