NPASS Compound

Natural Product: NPC226407

Natural Product ID	NPC226407
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KKCYUJUITAANCB-WWCCTYCASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102408531
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 96100 0 0 0 0 0 0 0 0999 V2000 -8.0023 -2.6155 -3.8264 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8700 -3.7123 -2.9567 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7243 -3.7871 -2.1762 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7263 -2.8187 -2.2286 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5804 -2.8784 -1.4598 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5452 -1.7868 -1.5583 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8471 -0.7441 -0.5465 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8004 -1.3572 0.8595 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8526 -0.1850 1.6119 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8234 0.6163 1.1020 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0742 2.0492 1.4091 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5819 2.2929 2.6829 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8482 3.5879 3.0478 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6156 4.6493 2.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1130 4.3673 0.9093 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8361 3.0601 0.5214 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9020 5.4440 0.0657 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4008 5.2664 -1.2277 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8988 5.9476 2.5671 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3510 3.8498 4.3053 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5846 2.7914 5.2003 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7936 0.3235 -0.3731 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4101 -0.1741 -0.7223 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5356 0.8975 -0.4949 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7609 0.6101 -0.7820 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3320 1.5655 -1.8046 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3625 2.4811 -1.1774 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4798 1.7042 -0.4689 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9334 0.3842 -0.0907 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6062 -0.4792 0.8932 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9220 -0.7910 0.6562 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0195 -0.0010 0.8066 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9071 1.1669 1.2390 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3578 -0.5293 0.4554 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4097 0.2265 0.6118 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7798 -0.1610 0.3063 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8287 0.7085 0.5374 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1354 0.3346 0.2220 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4208 -0.8964 -0.3232 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3821 -1.7690 -0.5565 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0688 -1.3941 -0.2394 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7538 -1.2133 -0.6200 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5997 0.5854 0.3564 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5609 1.5762 -1.3845 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7905 3.4061 -0.3258 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8332 0.9162 -2.9278 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4010 -3.9367 -0.5977 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3713 -4.9264 -0.5127 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5048 -4.8315 -1.2986 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4920 -5.8090 -1.2329 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2204 -6.0133 0.3534 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0451 -6.0755 1.1527 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0016 -2.5711 -4.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8035 -1.6388 -3.3418 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2434 -2.7653 -4.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8456 -1.9852 -2.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5820 -2.2811 -1.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5090 -1.4394 -2.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8140 -0.2331 -0.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6398 -1.9915 1.0959 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8026 -1.7958 1.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8701 0.3598 1.6194 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7656 1.4706 3.3838 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4327 2.8887 -0.4544 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3036 5.1964 -1.2452 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6792 6.1264 -1.9064 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8769 4.3872 -1.7180 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7659 6.3536 2.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6252 2.3737 5.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1572 3.2469 6.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1751 1.9661 4.7627 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9985 1.1663 -1.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2800 -0.4855 -1.7553 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2041 -1.0233 -0.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8343 -0.4120 -1.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5111 2.2273 -2.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8431 3.0238 -2.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7721 2.3630 0.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8426 -0.1911 -1.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0548 -1.4867 0.9315 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4998 -0.0799 1.9512 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4449 -1.5187 0.0816 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2624 1.2397 1.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5977 1.6725 0.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9420 1.0245 0.4105 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6246 -2.7362 -0.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2805 -2.1149 -0.4406 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0754 -1.0776 -1.5782 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0003 2.4697 -1.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9475 3.0668 0.0999 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0541 1.6028 -3.5973 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5054 -4.0024 0.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9056 -6.2245 -2.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1560 -6.8182 1.9472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1422 -6.1952 0.5541 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9946 -5.0804 1.6673 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 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 15 17 1 0 17 18 1 0 14 19 1 0 13 20 1 0 20 21 1 0 10 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 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 29 43 1 0 28 44 1 0 27 45 1 0 26 46 1 0 5 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 48 51 1 0 51 52 1 0 49 3 1 0 22 7 1 0 43 25 1 0 16 11 1 0 41 36 1 0 1 53 1 0 1 54 1 0 1 55 1 0 4 56 1 0 6 57 1 0 6 58 1 0 7 59 1 6 8 60 1 0 8 61 1 0 10 62 1 1 12 63 1 0 16 64 1 0 18 65 1 0 18 66 1 0 18 67 1 0 19 68 1 0 21 69 1 0 21 70 1 0 21 71 1 0 22 72 1 6 23 73 1 0 23 74 1 0 25 75 1 6 26 76 1 6 27 77 1 6 28 78 1 1 29 79 1 6 30 80 1 0 30 81 1 0 34 82 1 0 35 83 1 0 37 84 1 0 38 85 1 0 40 86 1 0 41 87 1 0 42 88 1 0 44 89 1 0 45 90 1 0 46 91 1 0 47 92 1 0 50 93 1 0 52 94 1 0 52 95 1 0 52 96 1 0 M END

Standard InCHIKey	KKCYUJUITAANCB-WWCCTYCASA-N
Standard InCHI	InChI=1S/C37H44O15/c1-45-25-12-20(13-26(46-2)31(25)40)11-22-16-50-36(21-14-27(47-3)32(41)28(15-21)48-4)24(22)17-51-37-35(44)34(43)33(42)29(52-37)18-49-30(39)10-7-19-5-8-23(38)9-6-19/h5-10,12-15,22,24,29,33-38,40-44H,11,16-18H2,1-4H3/b10-7+/t22-,24-,29+,33+,34-,35+,36+,37+/m0/s1
SMILES	COc1cc(C[C@H]2CO[C@H](c3cc(c(c(c3)OC)O)OC)[C@H]2CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c3ccc(cc3)O)O2)O)O)O)cc(c1O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	728.27	Volume:	708.578 ? Van der Waals volume.
Dense:	1.028	LogP:	2.065 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.157 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.141 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	31.0
TPSA:	212.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.795	Fsp³:	0.432
MCE-18:	113.547 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.844	Fluc inhibitor:	0.687 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.068 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.632 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.064	Promiscuous compounds:	0.216

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.053	MDCK Permeability:	-5.416
Pgp-inhibitor:	0.804	Pgp-substrate:	0.075
PAMPA:	0.007 ? 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):	0.001
20% Bioavailability (F20%):	0.275	30% Bioavailability (F30%):	0.463
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.642
Plasma Protein Binding (PPB):	93.134%	Volume Distribution (VD):	-0.405
Fu:	7.201% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.024
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.021	CYP1A2-substrate:	0.849
CYP2C19-inhibitor:	0.91	CYP2C19-substrate:	0.708
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.387
CYP3A4-inhibitor:	0.022	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.531 ? 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):

2.996

Half-life (T1/2):

3.305

ADMET: Toxicity

hERG Blockers:	0.153	hERG Blockers (10um):	0.394
Human Hepatotoxicity (H-HT):	0.683	Drug-induced Liver Injury (DILI):	0.828
AMES Toxicity:	0.726	Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.417	Skin Sensitization:	0.996
Carcinogencity:	0.22	Eye Corrosion:	0.0
Eye Irritation:	0.015	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.113	Ototoxicity:	0.916
Hematotoxicity:	0.196	Drug-induced Nephrotoxicity:	0.607
Genotoxicity:	0.412	RPMI-8226 Immunitoxicity:	0.288
A549 Cytotoxicity:	0.617	Hek293 Cytotoxicity:	0.848
BCF:	0.835 ? 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:	3.885 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.286 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.762 ? 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
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252914]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19251412]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37375900]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3369	Anemone narcissiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2175	Hyperbaena columbica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8349	Uga sinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26375	Viburnum grandifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9165	Asclepias curassavica	Species	Apocynaceae	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 NPC226407 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	13169
0.1-0.2	31095
0.2-0.3	4698
0.3-0.4	730
0.4-0.5	132
0.5-0.6	27
0.6-0.7	5
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
0.6506	Remote Similarity	NPC472713
0.6506	Remote Similarity	NPC606627
0.6353	Remote Similarity	NPC252402
0.6353	Remote Similarity	NPC102934
0.6163	Remote Similarity	NPC67467
0.5955	Remote Similarity	NPC472711
0.5882	Remote Similarity	NPC288416
0.5773	Remote Similarity	NPC11411
0.5684	Remote Similarity	NPC186073
0.5618	Remote Similarity	NPC34293
0.5517	Remote Similarity	NPC479473
0.5517	Remote Similarity	NPC275721
0.5517	Remote Similarity	NPC479468
0.5517	Remote Similarity	NPC479474
0.55	Remote Similarity	NPC125823
0.55	Remote Similarity	NPC7145
0.55	Remote Similarity	NPC143480
0.5455	Remote Similarity	NPC300262
0.5417	Remote Similarity	NPC21516
0.534	Remote Similarity	NPC201148
0.534	Remote Similarity	NPC59516
0.5208	Remote Similarity	NPC472612
0.5176	Remote Similarity	NPC485282
0.5176	Remote Similarity	NPC485283
0.5176	Remote Similarity	NPC485281
0.5161	Remote Similarity	NPC252114
0.5158	Remote Similarity	NPC10205
0.5155	Remote Similarity	NPC226005
0.5155	Remote Similarity	NPC476869
0.5155	Remote Similarity	NPC476866
0.5056	Remote Similarity	NPC470572
0.5055	Remote Similarity	NPC287597

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC226407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4683
0.1-0.2	4379
0.2-0.3	82
0.3-0.4	5
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
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
		NPD

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