NPASS Compound

Natural Product: NPC160508

Natural Product ID	NPC160508
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VCYHETOWRGYJEE-FLDQDSGZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5319785
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 92 98 0 0 0 0 0 0 0 0999 V2000 6.7050 -1.5652 -0.2018 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3947 -1.8250 0.2569 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3961 -2.5609 1.4806 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1351 -2.5710 2.2553 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9682 -2.1606 1.4594 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7247 -2.6968 1.6919 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6119 -2.3268 0.9609 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7722 -1.3898 -0.0307 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0377 -0.8538 -0.2565 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1408 -1.2034 0.4515 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5008 -0.6855 0.3012 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7757 0.3312 -0.7278 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9769 1.5787 -0.6311 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5066 2.2113 -1.7892 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7063 3.3232 -1.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3605 3.8231 -0.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8185 3.2195 0.6826 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6207 2.1049 0.5979 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4988 4.9703 -0.3386 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1195 4.5821 -0.4868 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1521 3.2621 -0.3156 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4314 2.7682 -0.4396 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4024 3.6537 -0.7384 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1220 4.9952 -0.9097 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8268 5.5221 -0.7887 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5313 6.8628 -0.9597 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5929 7.7373 -1.2716 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5404 1.2960 -0.2484 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7856 0.6405 0.0031 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6782 -0.8123 -0.4551 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9144 -1.4877 -0.5255 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0568 -0.6466 0.0042 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5718 -0.2195 1.3745 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3390 0.5426 1.3152 N 0 0 0 0 0 4 0 0 0 0 0 0 -2.4253 -0.0034 2.2916 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6554 1.8904 1.7811 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0538 -2.7640 -0.9656 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9284 -3.4338 -1.3631 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7153 -2.7841 -1.2958 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5624 -1.4663 -0.8400 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2833 -0.9540 -0.8181 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5361 -3.4306 -1.6982 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1302 -3.3225 -3.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0371 -4.7324 -1.8173 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3141 -5.3312 -1.8583 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6401 -2.8979 1.2332 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7427 -3.8453 2.2521 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6406 -1.4909 -1.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2263 -0.7037 0.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3157 -2.4922 -0.0389 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2080 -2.1007 2.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7360 -3.6248 1.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9519 -3.5527 2.7747 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2445 -1.8552 3.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5784 -3.4522 2.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1440 -0.1193 -1.0516 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7474 -0.2025 1.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8560 0.6027 -0.6654 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6250 -0.0560 -1.7814 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7632 1.8383 -2.7715 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3245 3.8376 -2.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5581 3.6082 1.6431 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9957 1.6155 1.4772 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6382 2.5764 -0.0792 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4042 3.2546 -0.8530 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9279 5.6697 -1.1459 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1056 8.6968 -1.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2754 7.3441 -2.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0844 8.0097 -0.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1750 0.9396 -1.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6910 0.9597 0.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5766 1.0652 -0.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9420 -1.3198 0.1911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3506 0.1541 -0.6577 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4430 -1.1468 1.9848 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3722 0.4243 1.7949 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2010 0.7351 3.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5022 -0.4046 1.8259 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8998 -0.8592 2.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3149 2.4479 1.1076 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0802 1.8448 2.8235 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7014 2.4399 1.8712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0486 -3.2220 -0.9923 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9768 -3.4104 -3.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3780 -2.3014 -3.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6629 -4.1080 -3.6459 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5914 -5.5741 -0.8075 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2780 -6.3294 -2.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0523 -4.7369 -2.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3875 -3.4229 3.2370 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1059 -4.7479 2.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -4.1745 2.4443 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 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 16 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 25 26 1 0 26 27 1 0 22 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 31 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 39 42 1 0 42 43 1 0 38 44 1 0 44 45 1 0 7 46 1 0 46 47 1 0 11 2 1 0 18 13 1 0 25 20 1 0 34 29 1 0 10 5 1 0 40 30 1 0 41 8 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 6 55 1 0 9 56 1 0 11 57 1 0 12 58 1 0 12 59 1 0 14 60 1 0 15 61 1 0 17 62 1 0 18 63 1 0 21 64 1 0 23 65 1 0 24 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 29 72 1 6 32 73 1 0 32 74 1 0 33 75 1 0 33 76 1 0 35 77 1 0 35 78 1 0 35 79 1 0 36 80 1 0 36 81 1 0 36 82 1 0 37 83 1 0 43 84 1 0 43 85 1 0 43 86 1 0 45 87 1 0 45 88 1 0 45 89 1 0 47 90 1 0 47 91 1 0 47 92 1 0 M CHG 1 34 1 M END

Standard InCHIKey	VCYHETOWRGYJEE-FLDQDSGZSA-N
Standard InCHI	InChI=1S/C39H45N2O6/c1-40-16-14-26-21-33(43-5)35-23-29(26)30(40)18-24-8-11-28(12-9-24)46-34-20-25(10-13-32(34)42-4)19-31-37-27(15-17-41(31,2)3)22-36(44-6)38(45-7)39(37)47-35/h8-13,20-23,30-31H,14-19H2,1-7H3/q+1/t30?,31-/m0/s1
SMILES	CN1CCc2cc(c3cc2C1Cc1ccc(cc1)Oc1cc(ccc1OC)C[C@H]1c2c(CC[N+]1(C)C)cc(c(c2O3)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	637.33	Volume:	667.62 ? Van der Waals volume.
Dense:	0.955	LogP:	2.846 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.939 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.441 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	42.0
TPSA:	58.62 ? 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:	0.218	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.948	Fsp³:	0.385
MCE-18:	135.148 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.406 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.567 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.093

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982	MDCK Permeability:	-4.798
Pgp-inhibitor:	0.17	Pgp-substrate:	0.999
PAMPA:	0.018 ? 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):	0.084
20% Bioavailability (F20%):	0.99	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147	MRP1:	0.971
Plasma Protein Binding (PPB):	54.236%	Volume Distribution (VD):	-0.304
Fu:	49.558% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.089
OATP1B3 inhibitor:	0.185	BCRP inhibitor:	0.447
BSEP inhibitor:	0.97

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.795	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.99	CYP3A4-substrate:	0.847
CYP2B6-substrate:	0.994	CYP2C8-inhibitor:	0.0
HLM stability:	0.017 ? 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):

6.959

Half-life (T1/2):

2.187

ADMET: Toxicity

hERG Blockers:	0.854	hERG Blockers (10um):	0.702
Human Hepatotoxicity (H-HT):	0.19	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.102	Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.994	Skin Sensitization:	0.597
Carcinogencity:	0.735	Eye Corrosion:	0.0
Eye Irritation:	0.015	Respiratory Toxicity:	0.995
Drug-induced Neurotoxicity:	0.756	Ototoxicity:	0.442
Hematotoxicity:	0.02	Drug-induced Nephrotoxicity:	0.06
Genotoxicity:	0.141	RPMI-8226 Immunitoxicity:	0.065
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.609
BCF:	2.462 ? 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:	4.801 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.665 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.053 ? 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
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[20030508]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3728032]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12178	Pinellia pedatisecta	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12178	Pinellia pedatisecta	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12178	Pinellia pedatisecta	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12178	Pinellia pedatisecta	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12178	Pinellia pedatisecta	Species	Araceae	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 NPC160508 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	33776
0.1-0.2	15531
0.2-0.3	344
0.3-0.4	84
0.4-0.5	54
0.5-0.6	41
0.6-0.7	25
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	Natural Product ID
0.6835	Remote Similarity	NPC76682
0.6835	Remote Similarity	NPC10908
0.6835	Remote Similarity	NPC63646
0.6835	Remote Similarity	NPC317145
0.6835	Remote Similarity	NPC198498
0.6835	Remote Similarity	NPC115284
0.6543	Remote Similarity	NPC276890
0.6316	Remote Similarity	NPC247639
0.6316	Remote Similarity	NPC25084
0.618	Remote Similarity	NPC195538
0.6118	Remote Similarity	NPC603853
0.6092	Remote Similarity	NPC311973
0.6047	Remote Similarity	NPC290582
0.6047	Remote Similarity	NPC217748
0.6047	Remote Similarity	NPC73492
0.6047	Remote Similarity	NPC182052
0.6047	Remote Similarity	NPC271013
0.6047	Remote Similarity	NPC299990
0.6047	Remote Similarity	NPC42663
0.6047	Remote Similarity	NPC15414
0.6047	Remote Similarity	NPC480587
0.6023	Remote Similarity	NPC116465
0.6	Remote Similarity	NPC12424
0.6	Remote Similarity	NPC129518
0.6	Remote Similarity	NPC251580
0.5977	Remote Similarity	NPC279228
0.5934	Remote Similarity	NPC243454
0.5843	Remote Similarity	NPC185639
0.5843	Remote Similarity	NPC251735
0.5843	Remote Similarity	NPC49075
0.5843	Remote Similarity	NPC599951
0.5745	Remote Similarity	NPC10871
0.573	Remote Similarity	NPC239824
0.5698	Remote Similarity	NPC227060
0.5698	Remote Similarity	NPC603603
0.5667	Remote Similarity	NPC254441
0.5667	Remote Similarity	NPC223690
0.5667	Remote Similarity	NPC9532
0.5455	Remote Similarity	NPC41122
0.5455	Remote Similarity	NPC318805
0.5435	Remote Similarity	NPC229373
0.5393	Remote Similarity	NPC480591
0.5361	Remote Similarity	NPC480586
0.5361	Remote Similarity	NPC480590
0.5316	Remote Similarity	NPC317439
0.5263	Remote Similarity	NPC212237
0.5263	Remote Similarity	NPC475479
0.5227	Remote Similarity	NPC41376
0.5213	Remote Similarity	NPC181796
0.5213	Remote Similarity	NPC290005
0.5213	Remote Similarity	NPC54654
0.5213	Remote Similarity	NPC7715
0.5213	Remote Similarity	NPC328155
0.5213	Remote Similarity	NPC222661
0.5213	Remote Similarity	NPC285931
0.5208	Remote Similarity	NPC24260
0.5208	Remote Similarity	NPC611658
0.5158	Remote Similarity	NPC16357
0.5158	Remote Similarity	NPC302245
0.5152	Remote Similarity	NPC82457
0.5116	Remote Similarity	NPC30779
0.5104	Remote Similarity	NPC323537
0.5102	Remote Similarity	NPC239584
0.5054	Remote Similarity	NPC475393
0.5054	Remote Similarity	NPC286119
0.5052	Remote Similarity	NPC485712

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC160508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5392
0.1-0.2	3694
0.2-0.3	52
0.3-0.4	4
0.4-0.5	1
0.5-0.6	0
0.6-0.7	5
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
0.7303	Intermediate Similarity	NPD8053	Approved
0.7033	Intermediate Similarity	NPD8054	Phase 4
0.6835	Remote Similarity	NPD8099	Discontinued
0.6625	Remote Similarity	NPD8252	Phase 4
0.6543	Remote Similarity	NPD8251	Approved
0.631	Remote Similarity	NPD8156	Discontinued
0.6047	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