NPASS Compound

Natural Product: NPC218636

Natural Product ID	NPC218636
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WIGKZVISOMPZRU-WGFIQVRRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11972298
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

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 75 79 0 0 0 0 0 0 0 0999 V2000 3.5029 -5.4861 1.5683 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4573 -4.5996 1.0324 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0948 -3.2594 0.8647 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0113 -2.3944 0.3495 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7101 -1.0534 0.1610 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4434 -0.6132 0.5134 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1577 0.7171 0.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0427 1.1727 0.6106 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1550 1.5244 -0.2153 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3976 1.0453 -0.5498 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4635 1.8680 -1.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7028 1.3262 -1.4206 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7387 2.0630 -1.9552 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5654 3.4111 -2.2057 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3448 3.9663 -1.9053 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2950 3.2132 -1.3624 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5952 4.1914 -2.7483 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5969 -0.2302 -0.3369 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4683 -1.4706 1.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8483 -2.8431 1.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2891 -1.0978 1.3840 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -0.7235 1.7158 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4262 -1.2458 3.0682 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6998 -0.4967 3.3340 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2806 0.2310 2.1569 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0544 -0.5061 0.8913 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1696 0.3551 -0.3522 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3142 1.0734 -0.4790 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4879 0.3499 -0.5694 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4551 0.8790 0.4599 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5504 1.6258 -0.2898 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2850 0.5440 -1.0959 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2368 -0.2449 -1.8445 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7369 -0.5717 -3.2329 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8054 -1.3114 -3.9540 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0611 0.4998 -1.8640 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0332 1.2144 -2.0611 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8710 2.4216 -1.2409 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9652 -0.1252 1.2713 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8644 -1.1787 0.7906 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9198 1.5797 2.1379 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5298 0.3898 4.4315 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6527 -2.6193 2.9199 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7128 -5.6287 0.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0666 -5.0074 2.4681 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0355 -6.4301 1.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0013 -2.7053 0.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9306 2.5511 -0.3617 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8241 0.2628 -1.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6870 1.6275 -2.1897 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2011 5.0395 -2.1058 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3711 3.6925 -1.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2916 4.5712 -2.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0832 -3.4665 1.6192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0297 0.3982 1.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3019 -1.1184 3.8794 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4463 -1.2556 3.7231 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3916 0.2538 2.3501 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8818 -1.2644 0.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9732 -0.2283 -1.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3206 1.0987 -0.3027 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3363 -0.7630 -0.5009 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9730 1.6259 1.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2061 2.2085 0.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8903 -0.0778 -0.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0046 -1.2182 -1.3509 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6276 -1.2311 -3.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0904 0.3160 -3.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0551 -1.5301 -3.3552 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5329 2.0313 -2.3058 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9674 3.3841 -1.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4685 -0.9531 1.0608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1666 2.0203 1.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7907 1.0055 4.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9582 -2.7999 1.9732 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 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 14 17 1 0 10 18 1 0 6 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 26 40 1 0 25 41 1 0 24 42 1 0 23 43 1 0 20 3 1 0 40 22 1 0 18 5 1 0 36 29 1 0 16 11 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 9 48 1 0 12 49 1 0 13 50 1 0 15 51 1 0 16 52 1 0 17 53 1 0 20 54 1 0 22 55 1 1 23 56 1 1 24 57 1 1 25 58 1 1 26 59 1 6 27 60 1 0 27 61 1 0 29 62 1 1 30 63 1 1 31 64 1 1 32 65 1 1 33 66 1 1 34 67 1 0 34 68 1 0 35 69 1 0 37 70 1 0 38 71 1 0 39 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 M END

Standard InCHIKey	WIGKZVISOMPZRU-WGFIQVRRSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-38-13-6-16-20(14(31)8-15(40-16)11-2-4-12(30)5-3-11)17(7-13)41-28-26(37)24(35)22(33)19(43-28)10-39-27-25(36)23(34)21(32)18(9-29)42-27/h2-8,18-19,21-30,32-37H,9-10H2,1H3/t18-,19-,21+,22+,23+,24+,25-,26-,27-,28+/m1/s1
SMILES	COc1cc2c(c(=O)cc(c3ccc(cc3)O)o2)c(c1)O[C@@H]1[C@@H]([C@H]([C@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	0.487 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.044 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.295 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.14	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.601	Fsp³:	0.464
MCE-18:	115.098 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.609	Fluc inhibitor:	0.258 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.861 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.445 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.071	Promiscuous compounds:	0.241

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.39	MDCK Permeability:	-5.19
Pgp-inhibitor:	0.0	Pgp-substrate:	0.778
PAMPA:	1.0 ? 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):	0.899
20% Bioavailability (F20%):	0.982	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.482
Plasma Protein Binding (PPB):	82.748%	Volume Distribution (VD):	-0.076
Fu:	17.389% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.972
OATP1B3 inhibitor:	0.984	BCRP inhibitor:	0.014
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.849 ? 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):

1.48

Half-life (T1/2):

3.076

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.52	Drug-induced Liver Injury (DILI):	0.926
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.149	Skin Sensitization:	0.999
Carcinogencity:	0.394	Eye Corrosion:	0.0
Eye Irritation:	0.301	Respiratory Toxicity:	0.093
Drug-induced Neurotoxicity:	0.033	Ototoxicity:	0.906
Hematotoxicity:	0.596	Drug-induced Nephrotoxicity:	0.559
Genotoxicity:	0.934	RPMI-8226 Immunitoxicity:	0.166
A549 Cytotoxicity:	0.957	Hek293 Cytotoxicity:	0.882
BCF:	0.38 ? 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:	3.017 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.567 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.674 ? 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
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15635251]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[24660446]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792158]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[501363]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320737]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24342	Lupinus albus	Species	Fabaceae	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 NPC218636 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	22284
0.1-0.2	22896
0.2-0.3	3346
0.3-0.4	903
0.4-0.5	301
0.5-0.6	95
0.6-0.7	19
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8659	High Similarity	NPC129827
0.8214	Intermediate Similarity	NPC473512
0.7875	Intermediate Similarity	NPC610763
0.7558	Intermediate Similarity	NPC295613
0.7159	Intermediate Similarity	NPC473657
0.7079	Intermediate Similarity	NPC15358
0.7033	Intermediate Similarity	NPC284277
0.6703	Remote Similarity	NPC44931
0.6667	Remote Similarity	NPC475366
0.6667	Remote Similarity	NPC475497
0.6591	Remote Similarity	NPC284960
0.6588	Remote Similarity	NPC110349
0.6588	Remote Similarity	NPC83283
0.6552	Remote Similarity	NPC182045
0.6452	Remote Similarity	NPC102028
0.6264	Remote Similarity	NPC61791
0.6207	Remote Similarity	NPC39360
0.6207	Remote Similarity	NPC29763
0.6207	Remote Similarity	NPC210003
0.6136	Remote Similarity	NPC93337
0.6105	Remote Similarity	NPC22062
0.6105	Remote Similarity	NPC473634
0.6105	Remote Similarity	NPC138811
0.6067	Remote Similarity	NPC105025
0.604	Remote Similarity	NPC244875
0.6022	Remote Similarity	NPC172807
0.5938	Remote Similarity	NPC210073
0.5876	Remote Similarity	NPC204693
0.5842	Remote Similarity	NPC101636
0.58	Remote Similarity	NPC488089
0.5778	Remote Similarity	NPC146792
0.5773	Remote Similarity	NPC479405
0.5714	Remote Similarity	NPC479404
0.5714	Remote Similarity	NPC213052
0.57	Remote Similarity	NPC473623
0.57	Remote Similarity	NPC209296
0.5688	Remote Similarity	NPC298666
0.567	Remote Similarity	NPC47923
0.5657	Remote Similarity	NPC488073
0.5657	Remote Similarity	NPC64051
0.5652	Remote Similarity	NPC222936
0.5612	Remote Similarity	NPC156869
0.5604	Remote Similarity	NPC95090
0.5604	Remote Similarity	NPC27408
0.5604	Remote Similarity	NPC259152
0.56	Remote Similarity	NPC65711
0.5567	Remote Similarity	NPC236191
0.5556	Remote Similarity	NPC186816
0.5545	Remote Similarity	NPC483707
0.5534	Remote Similarity	NPC298171
0.5521	Remote Similarity	NPC52353
0.551	Remote Similarity	NPC301683
0.551	Remote Similarity	NPC275454
0.5495	Remote Similarity	NPC58053
0.549	Remote Similarity	NPC270675
0.549	Remote Similarity	NPC195685
0.5484	Remote Similarity	NPC27942
0.5474	Remote Similarity	NPC293004
0.5474	Remote Similarity	NPC311830
0.5463	Remote Similarity	NPC311850
0.5446	Remote Similarity	NPC479403
0.5435	Remote Similarity	NPC168822
0.5435	Remote Similarity	NPC189142
0.5435	Remote Similarity	NPC77660
0.5421	Remote Similarity	NPC472993
0.5413	Remote Similarity	NPC488083
0.5408	Remote Similarity	NPC51774
0.54	Remote Similarity	NPC473571
0.54	Remote Similarity	NPC110941
0.5385	Remote Similarity	NPC331652
0.5376	Remote Similarity	NPC186807
0.5376	Remote Similarity	NPC45638
0.537	Remote Similarity	NPC25523
0.5366	Remote Similarity	NPC57751
0.5361	Remote Similarity	NPC211594
0.5333	Remote Similarity	NPC472994
0.5319	Remote Similarity	NPC100720
0.5319	Remote Similarity	NPC201292
0.5315	Remote Similarity	NPC68592
0.5312	Remote Similarity	NPC607707
0.5306	Remote Similarity	NPC254540
0.5301	Remote Similarity	NPC189589
0.53	Remote Similarity	NPC164047
0.53	Remote Similarity	NPC470452
0.53	Remote Similarity	NPC470453
0.5269	Remote Similarity	NPC323593
0.5269	Remote Similarity	NPC203500
0.5238	Remote Similarity	NPC208769
0.5233	Remote Similarity	NPC37074
0.5208	Remote Similarity	NPC22832
0.5208	Remote Similarity	NPC243930
0.5208	Remote Similarity	NPC601144
0.52	Remote Similarity	NPC173582
0.52	Remote Similarity	NPC265885
0.52	Remote Similarity	NPC181465
0.52	Remote Similarity	NPC215710
0.52	Remote Similarity	NPC67105
0.52	Remote Similarity	NPC473438
0.52	Remote Similarity	NPC253788
0.5196	Remote Similarity	NPC46202
0.5189	Remote Similarity	NPC135358
0.5185	Remote Similarity	NPC189564
0.5172	Remote Similarity	NPC287780
0.5172	Remote Similarity	NPC60982
0.5161	Remote Similarity	NPC261866
0.5161	Remote Similarity	NPC143851
0.5155	Remote Similarity	NPC602805
0.5149	Remote Similarity	NPC65003
0.5149	Remote Similarity	NPC65563
0.5149	Remote Similarity	NPC470949
0.5149	Remote Similarity	NPC63105
0.5133	Remote Similarity	NPC198199
0.5106	Remote Similarity	NPC297987
0.51	Remote Similarity	NPC471079
0.5096	Remote Similarity	NPC229409
0.5094	Remote Similarity	NPC470449
0.5054	Remote Similarity	NPC183357
0.5053	Remote Similarity	NPC58716
0.5053	Remote Similarity	NPC24043
0.5048	Remote Similarity	NPC600130
0.5043	Remote Similarity	NPC262222

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC218636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5543
0.1-0.2	3515
0.2-0.3	79
0.3-0.4	7
0.4-0.5	3
0.5-0.6	1
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
0.6633	Remote Similarity	NPD7472	Pre-clinical
0.57	Remote Similarity	NPD7054	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