NPASS Compound

Natural Product: NPC36138

Natural Product ID	NPC36138
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Methoxykaempferol-3-O-Beta-D-6''-(P-Coumaroyl)Glucopyranoside
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037059
PubChem CID	70696488
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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 73 77 0 0 0 0 0 0 0 0999 V2000 -9.1049 -3.5957 0.4542 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0398 -3.4101 1.3704 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2259 -2.2831 1.3276 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5196 -1.1379 2.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6991 -0.0342 1.9780 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5327 -0.0104 1.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2527 -1.1598 0.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0797 -2.2803 0.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7399 -3.4177 -0.1748 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1051 -1.1443 -0.2523 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8318 -2.1790 -0.9008 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3026 0.0077 -0.2726 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6353 1.1195 0.4390 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8875 2.3714 0.4906 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1458 3.2812 1.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5510 4.4964 1.6397 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6408 4.8739 0.6848 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3571 4.0205 -0.3490 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9858 2.7656 -0.4433 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0257 6.1292 0.7981 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7672 1.0378 1.1602 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1561 -0.0487 -1.0419 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8873 -0.5067 -0.5036 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6341 -1.9281 -0.8866 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7786 -2.2807 -1.1153 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7453 -1.1842 -1.3768 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3610 0.1007 -0.6584 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1932 1.2347 -1.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5556 1.0246 -0.9100 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5373 1.9150 -1.3050 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1661 2.9220 -1.9519 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9526 1.7042 -0.9888 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3224 0.6473 -0.3127 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7099 0.4023 0.0198 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0058 -0.7546 0.7444 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3113 -1.0534 1.0971 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3334 -0.2053 0.7328 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0547 0.9350 0.0204 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7484 1.2349 -0.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6464 -0.4732 1.0682 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0544 0.3341 -0.9781 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0059 -1.5423 -0.8564 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8778 -3.1558 -2.2377 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0990 -2.8056 0.1352 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6731 -1.1412 2.8081 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0030 -3.0108 0.7034 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3284 -4.6882 0.3203 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7613 -3.2430 -0.5447 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9303 0.8678 2.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1505 -3.6361 -1.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8681 2.9783 2.2862 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7868 5.1648 2.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6363 4.2952 -1.1234 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7633 2.1395 -1.2922 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5749 6.9649 0.9873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0018 -0.5250 0.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2156 -2.2029 -1.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1931 -2.9465 -0.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8292 -1.0162 -2.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -0.0277 0.4172 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8505 2.1645 -0.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0048 1.3171 -2.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6603 2.4284 -1.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5565 -0.0551 0.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1856 -1.3924 1.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5231 -1.9663 1.6656 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8202 1.6450 -0.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5447 2.1426 -0.8976 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1852 -1.1211 0.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0403 -2.5064 -0.7111 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5732 -4.0597 -1.9727 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4330 -3.6469 -0.2586 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5672 -0.8892 3.7827 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 8 9 1 0 7 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 17 20 1 0 13 21 1 0 12 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 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 27 41 1 0 26 42 1 0 25 43 1 0 24 44 1 0 4 45 1 0 8 3 1 0 19 14 1 0 41 23 1 0 21 6 1 0 39 34 1 0 1 46 1 0 1 47 1 0 1 48 1 0 5 49 1 0 9 50 1 0 15 51 1 0 16 52 1 0 18 53 1 0 19 54 1 0 20 55 1 0 23 56 1 1 24 57 1 6 25 58 1 1 26 59 1 6 27 60 1 1 28 61 1 0 28 62 1 0 32 63 1 0 33 64 1 0 35 65 1 0 36 66 1 0 38 67 1 0 39 68 1 0 40 69 1 0 42 70 1 0 43 71 1 0 44 72 1 0 45 73 1 0 M END

Standard InCHIKey	QSWRVQDERAITMT-OXJVYKMDSA-N
Standard InCHI	InChI=1S/C31H28O14/c1-41-29-18(34)12-19-22(24(29)37)25(38)30(28(43-19)15-5-9-17(33)10-6-15)45-31-27(40)26(39)23(36)20(44-31)13-42-21(35)11-4-14-2-7-16(32)8-3-14/h2-12,20,23,26-27,31-34,36-37,39-40H,13H2,1H3/b11-4+/t20-,23-,26+,27-,31+/m1/s1
SMILES	COc1c(cc2c(c1O)c(=O)c(c(c1ccc(cc1)O)o2)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(cc2)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.15	Volume:	590.739 ? Van der Waals volume.
Dense:	1.057	LogP:	1.92 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.914 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.473 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	32.0
TPSA:	225.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.259	Fsp³:	0.226
MCE-18:	107.684 ? 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:	0.744	Fluc inhibitor:	0.714 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.924 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.867 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.057	Promiscuous compounds:	0.605

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.139	MDCK Permeability:	-5.272
Pgp-inhibitor:	0.028	Pgp-substrate:	0.028
PAMPA:	0.942 ? 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):	0.003
20% Bioavailability (F20%):	0.475	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.004
Plasma Protein Binding (PPB):	90.461%	Volume Distribution (VD):	-0.102
Fu:	6.938% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.139
BSEP inhibitor:	0.959

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.512
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.605
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.98 ? 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):

2.363

Half-life (T1/2):

3.259

ADMET: Toxicity

hERG Blockers:	0.076	hERG Blockers (10um):	0.418
Human Hepatotoxicity (H-HT):	0.571	Drug-induced Liver Injury (DILI):	0.896
AMES Toxicity:	0.801	Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.551	Skin Sensitization:	0.998
Carcinogencity:	0.228	Eye Corrosion:	0.0
Eye Irritation:	0.278	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.029	Ototoxicity:	0.72
Hematotoxicity:	0.029	Drug-induced Nephrotoxicity:	0.215
Genotoxicity:	0.961	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.481	Hek293 Cytotoxicity:	0.92
BCF:	0.824 ? 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:	3.654 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.626 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.301 ? 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
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	Flowers	Santana do Riacho, State Minas Gerais, Brazil	n.a.	PMID[22506638]
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	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

Activity Type	# Activity
Activity	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	1.279	mM	PMID[22506638]

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 NPC36138 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	14012
0.1-0.2	30640
0.2-0.3	4021
0.3-0.4	726
0.4-0.5	296
0.5-0.6	105
0.6-0.7	34
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9101	High Similarity	NPC470416
0.8333	Intermediate Similarity	NPC85751
0.8333	Intermediate Similarity	NPC19240
0.7766	Intermediate Similarity	NPC223426
0.7766	Intermediate Similarity	NPC470450
0.7732	Intermediate Similarity	NPC217520
0.7684	Intermediate Similarity	NPC214621
0.7684	Intermediate Similarity	NPC34267
0.7629	Intermediate Similarity	NPC477895
0.7204	Intermediate Similarity	NPC473571
0.7204	Intermediate Similarity	NPC110941
0.7143	Intermediate Similarity	NPC81042
0.7059	Intermediate Similarity	NPC139571
0.701	Intermediate Similarity	NPC470447
0.6939	Remote Similarity	NPC470449
0.68	Remote Similarity	NPC470455
0.6771	Remote Similarity	NPC470125
0.6742	Remote Similarity	NPC488080
0.6742	Remote Similarity	NPC169977
0.6667	Remote Similarity	NPC80068
0.6634	Remote Similarity	NPC96605
0.6634	Remote Similarity	NPC280642
0.6598	Remote Similarity	NPC488074
0.6574	Remote Similarity	NPC488079
0.6574	Remote Similarity	NPC488078
0.6566	Remote Similarity	NPC270675
0.6566	Remote Similarity	NPC195685
0.6535	Remote Similarity	NPC218161
0.65	Remote Similarity	NPC477629
0.6465	Remote Similarity	NPC476620
0.6449	Remote Similarity	NPC474093
0.6449	Remote Similarity	NPC104910
0.6429	Remote Similarity	NPC488073
0.6429	Remote Similarity	NPC126784
0.6429	Remote Similarity	NPC241423
0.6327	Remote Similarity	NPC129264
0.6286	Remote Similarity	NPC480796
0.6286	Remote Similarity	NPC472993
0.6275	Remote Similarity	NPC470445
0.6214	Remote Similarity	NPC470446
0.6214	Remote Similarity	NPC472994
0.6195	Remote Similarity	NPC25946
0.6139	Remote Similarity	NPC104883
0.6139	Remote Similarity	NPC488679
0.61	Remote Similarity	NPC153755
0.6095	Remote Similarity	NPC599948
0.6038	Remote Similarity	NPC470451
0.6022	Remote Similarity	NPC305811
0.5979	Remote Similarity	NPC116864
0.5979	Remote Similarity	NPC244776
0.5957	Remote Similarity	NPC42773
0.5957	Remote Similarity	NPC45522
0.5943	Remote Similarity	NPC121703
0.5859	Remote Similarity	NPC471079
0.5851	Remote Similarity	NPC10205
0.5833	Remote Similarity	NPC101026
0.5833	Remote Similarity	NPC488077
0.5825	Remote Similarity	NPC270448
0.58	Remote Similarity	NPC173582
0.58	Remote Similarity	NPC265885
0.58	Remote Similarity	NPC181465
0.58	Remote Similarity	NPC215710
0.58	Remote Similarity	NPC473438
0.58	Remote Similarity	NPC253788
0.5763	Remote Similarity	NPC473554
0.5743	Remote Similarity	NPC65563
0.5743	Remote Similarity	NPC470949
0.5726	Remote Similarity	NPC21359
0.5726	Remote Similarity	NPC460984
0.5714	Remote Similarity	NPC291153
0.5701	Remote Similarity	NPC603856
0.57	Remote Similarity	NPC609888
0.5652	Remote Similarity	NPC241781
0.5645	Remote Similarity	NPC475179
0.5636	Remote Similarity	NPC470712
0.5636	Remote Similarity	NPC164704
0.5619	Remote Similarity	NPC205824
0.5614	Remote Similarity	NPC156785
0.5614	Remote Similarity	NPC474522
0.5565	Remote Similarity	NPC470720
0.5556	Remote Similarity	NPC478277
0.5556	Remote Similarity	NPC478276
0.5556	Remote Similarity	NPC478275
0.5556	Remote Similarity	NPC92815
0.5521	Remote Similarity	NPC24043
0.55	Remote Similarity	NPC172807
0.5478	Remote Similarity	NPC162394
0.5421	Remote Similarity	NPC476472
0.5421	Remote Similarity	NPC294815
0.5421	Remote Similarity	NPC16194
0.5398	Remote Similarity	NPC470716
0.5398	Remote Similarity	NPC470718
0.5385	Remote Similarity	NPC470444
0.5385	Remote Similarity	NPC186816
0.5377	Remote Similarity	NPC37668
0.5377	Remote Similarity	NPC473327
0.5368	Remote Similarity	NPC111929
0.5368	Remote Similarity	NPC320283
0.5368	Remote Similarity	NPC41121
0.5361	Remote Similarity	NPC46420
0.5357	Remote Similarity	NPC470715
0.5345	Remote Similarity	NPC470717
0.534	Remote Similarity	NPC67326
0.5333	Remote Similarity	NPC296018
0.5327	Remote Similarity	NPC101399
0.5327	Remote Similarity	NPC221288
0.5327	Remote Similarity	NPC217822
0.5327	Remote Similarity	NPC11847
0.5327	Remote Similarity	NPC198938
0.5327	Remote Similarity	NPC194836
0.5327	Remote Similarity	NPC91493
0.5327	Remote Similarity	NPC605081
0.5312	Remote Similarity	NPC77672
0.5312	Remote Similarity	NPC133671
0.5312	Remote Similarity	NPC135391
0.5312	Remote Similarity	NPC78263
0.5312	Remote Similarity	NPC250069
0.5288	Remote Similarity	NPC203259
0.5288	Remote Similarity	NPC33054
0.5288	Remote Similarity	NPC176740
0.5288	Remote Similarity	NPC471725
0.5288	Remote Similarity	NPC134532
0.5288	Remote Similarity	NPC156869
0.5288	Remote Similarity	NPC602582
0.5259	Remote Similarity	NPC470713
0.5253	Remote Similarity	NPC175107
0.5242	Remote Similarity	NPC487502
0.5238	Remote Similarity	NPC266960
0.5229	Remote Similarity	NPC260504
0.5229	Remote Similarity	NPC89809
0.5189	Remote Similarity	NPC472992
0.5185	Remote Similarity	NPC486577
0.5182	Remote Similarity	NPC483767
0.5182	Remote Similarity	NPC483769
0.5182	Remote Similarity	NPC483768
0.5182	Remote Similarity	NPC483766
0.5179	Remote Similarity	NPC189564
0.5175	Remote Similarity	NPC277532
0.5167	Remote Similarity	NPC480472
0.5152	Remote Similarity	NPC471405
0.5138	Remote Similarity	NPC471669
0.5122	Remote Similarity	NPC231787
0.51	Remote Similarity	NPC204937
0.5053	Remote Similarity	NPC54802
0.5053	Remote Similarity	NPC197304
0.505	Remote Similarity	NPC476869
0.505	Remote Similarity	NPC476866
0.5049	Remote Similarity	NPC477848
0.5043	Remote Similarity	NPC488734
0.5043	Remote Similarity	NPC488735
0.5043	Remote Similarity	NPC488739
0.5043	Remote Similarity	NPC488732
0.5043	Remote Similarity	NPC488738

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC36138 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3808
0.1-0.2	5258
0.2-0.3	72
0.3-0.4	7
0.4-0.5	4
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
0.5288	Remote Similarity	NPD6797	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