NPASS Compound

Natural Product: NPC476385

Natural Product ID	NPC476385
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Campneoside I
IUPAC Name	[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-2-methoxyethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms	Campneoside I
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL590462
PubChem CID	46228759
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 87 90 0 0 0 0 0 0 0 0999 V2000 0.1821 -2.2127 4.5795 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0464 -2.0045 3.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2816 -0.5554 2.9334 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5819 -0.2860 3.2474 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3824 0.0963 2.1790 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6476 -0.9568 1.3153 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9979 -1.2148 1.3218 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4075 -2.3462 0.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8686 -2.4704 0.4853 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6659 -1.5274 -0.1044 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0574 -1.6446 -0.0375 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6278 -2.7055 0.6196 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8331 -3.6454 1.2073 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4450 -3.5251 1.1385 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4186 -4.7116 1.8676 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0269 -2.7645 0.6503 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0366 -2.0099 -0.8884 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1551 -2.9820 -1.3947 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8400 1.3072 1.4532 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3226 1.3171 1.3912 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1347 -0.1045 1.5550 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5179 -0.2734 1.4053 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1415 -1.0921 0.5085 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4253 -1.7711 -0.2707 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6173 -1.1803 0.4519 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2083 -1.9752 -0.4189 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6462 -2.1277 -0.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5461 -1.4466 0.2352 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9039 -1.6174 0.0855 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3628 -2.5029 -0.8849 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4758 -3.1927 -1.6775 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1305 -3.0052 -1.5090 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9383 -4.0693 -2.6379 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7254 -2.7038 -1.0680 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0424 1.8959 0.2014 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8102 3.0064 0.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2710 3.7269 -0.7785 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0369 2.9457 -1.6049 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6955 3.6767 -2.5829 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9394 4.3428 -2.0822 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8423 4.6465 -3.3211 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7877 5.3316 -2.5301 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1617 4.3532 -1.5576 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7354 4.9456 -0.6984 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2110 6.4968 -1.9047 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2828 4.0751 -4.4878 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2203 2.4373 2.1603 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1473 -2.2724 4.7642 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1268 -2.2203 3.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5705 -2.7121 2.6368 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3589 0.0370 3.6515 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3478 0.4138 2.6192 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 -1.4437 2.3437 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5696 -0.3125 0.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9027 -3.2950 0.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2970 -0.6643 -0.6401 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6950 -0.8984 -0.5042 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8909 -4.3131 1.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9695 -5.2069 2.6314 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4385 -3.5954 0.2522 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6632 -3.9684 -1.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8647 -2.7396 -2.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2779 -3.0474 -0.7393 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2923 1.3005 0.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0984 1.8953 2.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3627 -0.7590 0.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2090 -0.5934 1.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5358 -2.5383 -1.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2185 -0.7540 0.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6456 -1.1035 0.6785 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4542 -3.5517 -2.1362 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2542 -4.9812 -2.3398 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1188 -3.6488 -1.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2511 3.7698 1.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6708 2.7131 1.0843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9265 4.5732 -0.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0313 2.9086 -3.3432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9853 5.3773 -2.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8715 3.8399 -2.4473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9843 4.4312 -0.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5293 5.4498 -3.7190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0289 5.6347 -3.2306 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3128 3.5541 -2.1995 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6510 4.6973 -1.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0800 6.4448 -1.4832 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6217 4.7680 -4.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4694 2.8355 2.6610 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 12 16 1 0 8 17 1 0 17 18 1 0 5 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 20 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 19 47 1 0 21 3 1 0 32 27 1 0 43 37 1 0 14 9 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 1 5 52 1 1 7 53 1 0 7 54 1 0 8 55 1 0 10 56 1 0 11 57 1 0 14 58 1 0 15 59 1 0 16 60 1 0 18 61 1 0 18 62 1 0 18 63 1 0 19 64 1 6 20 65 1 1 21 66 1 6 25 67 1 0 26 68 1 0 28 69 1 0 29 70 1 0 32 71 1 0 33 72 1 0 34 73 1 0 36 74 1 0 36 75 1 0 37 76 1 1 39 77 1 6 40 78 1 0 40 79 1 0 40 80 1 0 41 81 1 6 42 82 1 6 43 83 1 6 44 84 1 0 45 85 1 0 46 86 1 0 47 87 1 0 M END

Standard InCHIKey	OBZROZJRGRPYKZ-IUKXOIARSA-N
Standard InCHI	InChI=1S/C31H40O16/c1-14-25(38)27(40)26(39)23(45-14)13-43-30-28(41)31(44-12-22(42-2)16-5-7-18(34)20(36)10-16)46-21(11-32)29(30)47-24(37)8-4-15-3-6-17(33)19(35)9-15/h3-10,14,21-23,25-36,38-41H,11-13H2,1-2H3/b8-4+/t14-,21+,22?,23-,25-,26-,27+,28+,29+,30+,31+/m0/s1
SMILES	OC[C@H]1O[C@@H](OCC(c2ccc(c(c2)O)O)OC)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)OC[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	668.23	Volume:	630.058 ? Van der Waals volume.
Dense:	1.061	LogP:	-0.545 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.39 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.159 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	26.0
TPSA:	254.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.076	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.036	Fsp³:	0.516
MCE-18:	102.766 ? 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:	1
Colloidal aggregators:	0.691	Fluc inhibitor:	0.648 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.086 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.604 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.277	Promiscuous compounds:	0.387

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.244	MDCK Permeability:	-5.36
Pgp-inhibitor:	0.0	Pgp-substrate:	0.206
PAMPA:	0.999 ? 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):	0.125
20% Bioavailability (F20%):	0.979	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.095
Plasma Protein Binding (PPB):	68.062%	Volume Distribution (VD):	-0.264
Fu:	28.578% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.578 ? 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):

3.596

Half-life (T1/2):

3.615

ADMET: Toxicity

hERG Blockers:	0.037	hERG Blockers (10um):	0.357
Human Hepatotoxicity (H-HT):	0.234	Drug-induced Liver Injury (DILI):	0.445
AMES Toxicity:	0.94	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.032	Skin Sensitization:	1.0
Carcinogencity:	0.034	Eye Corrosion:	0.0
Eye Irritation:	0.056	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.995
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.141
Genotoxicity:	0.233	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.963	Hek293 Cytotoxicity:	0.457
BCF:	0.668 ? 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:	3.346 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.078 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.412 ? 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
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	fresh stems	n.a.	n.a.	PMID[20159656]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	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

Activity Type	# Activity
Inhibition	4

Activity Type	# Activity
Cell line	4

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
NPT1460	Cell line	L929	Mus musculus	Inhibition	=	7.7	%	PMID[9677271]
NPT1460	Cell line	L929	Mus musculus	Inhibition	=	-8.8	%	PMID[18590312]
NPT1460	Cell line	L929	Mus musculus	Inhibition	=	1.9	%	PMID[22225637]
NPT1460	Cell line	L929	Mus musculus	Inhibition	=	7.5	%	PubChem BioAssay data set

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 NPC476385 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	15706
0.1-0.2	31135
0.2-0.3	2616
0.3-0.4	321
0.4-0.5	56
0.5-0.6	17
0.6-0.7	4
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
0.7619	Intermediate Similarity	NPC134405
0.6224	Remote Similarity	NPC476382
0.6162	Remote Similarity	NPC476384
0.6064	Remote Similarity	NPC476376
0.604	Remote Similarity	NPC476381
0.5957	Remote Similarity	NPC476377
0.5745	Remote Similarity	NPC222433
0.5728	Remote Similarity	NPC476380
0.5638	Remote Similarity	NPC472350
0.5638	Remote Similarity	NPC197316
0.5638	Remote Similarity	NPC89105
0.5556	Remote Similarity	NPC252292
0.5505	Remote Similarity	NPC476386
0.5385	Remote Similarity	NPC476375
0.53	Remote Similarity	NPC269141
0.5208	Remote Similarity	NPC483706
0.5196	Remote Similarity	NPC112
0.5165	Remote Similarity	NPC473285
0.5155	Remote Similarity	NPC483705
0.5152	Remote Similarity	NPC476383
0.51	Remote Similarity	NPC47471
0.5096	Remote Similarity	NPC232992

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5602
0.1-0.2	3502
0.2-0.3	44
0.3-0.4	1
0.4-0.5	0
0.5-0.6	1
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
0.5638	Remote Similarity	NPD7266	Phase 2

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