NPASS Compound

Natural Product: NPC470444

Natural Product ID	NPC470444
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-Alpha-L-Rhamnopyranosyl-(1->2)-Beta-D-Glucopyranoside
IUPAC Name	3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037044
PubChem CID	70683918
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 76 80 0 0 0 0 0 0 0 0999 V2000 -3.9707 -2.2122 1.4794 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6424 -1.9155 2.1356 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7709 -2.2508 3.5925 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9287 -0.9944 4.3822 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7763 -0.0536 4.1023 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2860 -0.1344 2.7002 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3623 -0.5696 1.9206 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2423 -1.0061 2.4766 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -0.3931 1.8009 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9872 -0.4871 2.7998 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2425 -0.6196 1.9777 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2151 -1.9113 1.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9720 -2.2082 0.6988 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1339 -1.1281 0.5203 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4462 -0.3035 -0.5254 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7993 0.4558 -1.4076 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2281 0.0111 -2.5556 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4175 0.8505 -3.3924 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5414 2.1237 -3.1801 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0136 2.6422 -2.0432 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6906 1.8288 -1.1402 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1890 2.3503 -0.1138 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0971 3.9964 -1.7870 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7726 4.8038 -2.6945 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3354 4.2763 -3.8462 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2240 2.9263 -4.0980 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9916 5.1398 -4.6994 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8821 6.1602 -2.4421 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1173 7.0436 -2.9265 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4730 4.4889 -0.6342 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2723 -1.3770 -2.9497 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6826 -1.8409 -3.8714 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6629 -3.1287 -4.3514 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2851 -4.0432 -3.9648 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 -3.6104 -3.0655 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2060 -2.2976 -2.5797 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3482 -5.3497 -4.4184 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3013 -1.7820 0.1418 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0914 -0.7812 -0.7693 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3671 -0.5491 2.7985 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9984 0.7021 3.5245 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2756 1.2406 4.3174 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9237 -1.3444 5.7372 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6983 -2.9782 4.0826 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0309 -3.2385 1.0933 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8318 -2.0874 2.1642 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1700 -1.5121 0.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8699 -2.5811 1.6747 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6878 -2.8761 3.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9120 -0.5027 4.2038 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0165 -0.2370 4.8878 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0185 0.8586 2.3096 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6430 0.6432 1.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8604 -1.3684 3.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2671 0.2037 1.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5145 -2.7059 1.8832 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1119 -1.5618 0.2696 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6674 2.4928 -5.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6825 5.8231 -4.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5208 7.6417 -2.0669 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2985 7.7466 -3.6905 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 6.4311 -3.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4654 4.6360 -0.5067 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4352 -1.1246 -4.1788 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 -3.4264 -5.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9915 -4.3137 -2.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0066 -2.0269 -1.9203 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1839 -5.6650 -5.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4433 -2.7290 -0.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2997 -1.6022 0.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8636 -0.1999 -0.8667 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4140 -1.3968 3.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0472 1.4977 2.9632 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2489 1.7712 3.4973 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3436 -0.6601 6.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9221 -3.7005 4.6915 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 24 28 1 0 28 29 1 0 23 30 1 0 17 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 12 38 1 0 38 39 1 0 11 40 1 0 10 41 1 0 5 42 1 0 4 43 1 0 3 44 1 0 7 2 1 0 14 9 1 0 21 16 1 0 26 19 1 0 36 31 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 3 49 1 0 4 50 1 0 5 51 1 0 6 52 1 0 9 53 1 0 10 54 1 0 11 55 1 0 12 56 1 0 14 57 1 0 26 58 1 0 27 59 1 0 29 60 1 0 29 61 1 0 29 62 1 0 30 63 1 0 32 64 1 0 33 65 1 0 35 66 1 0 36 67 1 0 37 68 1 0 38 69 1 0 38 70 1 0 39 71 1 0 40 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 M END

Standard InCHIKey	LMYJHVXWGCYGHW-DRHZGDJGSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-16(32)20(36)22(38)27(40-9)44-26-21(37)17(33)14(8-29)42-28(26)43-25-19(35)15-13(7-12(31)24(39-2)18(15)34)41-23(25)10-3-5-11(30)6-4-10/h3-7,9,14,16-17,20-22,26-34,36-38H,8H2,1-2H3/t9-,14+,16-,17+,20+,21-,22+,26+,27-,28-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=C(C3=O)C(=C(C(=C4)O)OC)O)C5=CC=C(C=C5)O)CO)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	-0.457 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.463 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.004 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.775	Fsp³:	0.464
MCE-18:	122.073 ? 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:	0.186	Fluc inhibitor:	0.067 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.819 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.89 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.247	Promiscuous compounds:	0.396

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.351	MDCK Permeability:	-5.181
Pgp-inhibitor:	0.0	Pgp-substrate:	0.98
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):	0.876
20% Bioavailability (F20%):	0.433	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.943
Plasma Protein Binding (PPB):	75.568%	Volume Distribution (VD):	-0.178
Fu:	24.005% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.821	BCRP inhibitor:	0.569
BSEP inhibitor:	0.026

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.16	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.983
HLM stability:	0.003 ? 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):

1.511

Half-life (T1/2):

3.672

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.363
Human Hepatotoxicity (H-HT):	0.447	Drug-induced Liver Injury (DILI):	0.651
AMES Toxicity:	0.563	Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.312	Skin Sensitization:	0.341
Carcinogencity:	0.175	Eye Corrosion:	0.0
Eye Irritation:	0.111	Respiratory Toxicity:	0.027
Drug-induced Neurotoxicity:	0.108	Ototoxicity:	0.951
Hematotoxicity:	0.027	Drug-induced Nephrotoxicity:	0.023
Genotoxicity:	0.509	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.13	Hek293 Cytotoxicity:	0.77
BCF:	0.371 ? 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:	2.863 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.619 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.643 ? 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	=	1.529	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 NPC470444 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	20161
0.1-0.2	25046
0.2-0.3	3777
0.3-0.4	454
0.4-0.5	240
0.5-0.6	121
0.6-0.7	35
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8095	Intermediate Similarity	NPC163242
0.8095	Intermediate Similarity	NPC272068
0.7816	Intermediate Similarity	NPC240306
0.7647	Intermediate Similarity	NPC473682
0.7473	Intermediate Similarity	NPC220173
0.7412	Intermediate Similarity	NPC170052
0.7412	Intermediate Similarity	NPC135846
0.7386	Intermediate Similarity	NPC155877
0.7253	Intermediate Similarity	NPC32641
0.7253	Intermediate Similarity	NPC256188
0.7229	Intermediate Similarity	NPC488080
0.7229	Intermediate Similarity	NPC169977
0.7209	Intermediate Similarity	NPC476215
0.7065	Intermediate Similarity	NPC35119
0.6947	Remote Similarity	NPC602448
0.6923	Remote Similarity	NPC473571
0.6923	Remote Similarity	NPC110941
0.6907	Remote Similarity	NPC473072
0.6907	Remote Similarity	NPC488075
0.6774	Remote Similarity	NPC480471
0.6774	Remote Similarity	NPC488076
0.6742	Remote Similarity	NPC254855
0.6742	Remote Similarity	NPC94610
0.6737	Remote Similarity	NPC473071
0.663	Remote Similarity	NPC304741
0.6596	Remote Similarity	NPC12013
0.6596	Remote Similarity	NPC11432
0.6596	Remote Similarity	NPC477613
0.6556	Remote Similarity	NPC95866
0.6458	Remote Similarity	NPC142142
0.6437	Remote Similarity	NPC305811
0.6364	Remote Similarity	NPC42773
0.6364	Remote Similarity	NPC45522
0.6344	Remote Similarity	NPC470405
0.6277	Remote Similarity	NPC65003
0.6275	Remote Similarity	NPC25523
0.6224	Remote Similarity	NPC470447
0.6222	Remote Similarity	NPC101026
0.6222	Remote Similarity	NPC488077
0.6222	Remote Similarity	NPC224530
0.6162	Remote Similarity	NPC221342
0.6162	Remote Similarity	NPC476470
0.6146	Remote Similarity	NPC126784
0.6146	Remote Similarity	NPC241423
0.6139	Remote Similarity	NPC89052
0.6042	Remote Similarity	NPC255157
0.6042	Remote Similarity	NPC259896
0.602	Remote Similarity	NPC122467
0.6	Remote Similarity	NPC292929
0.5979	Remote Similarity	NPC488073
0.5946	Remote Similarity	NPC25946
0.59	Remote Similarity	NPC195257
0.5889	Remote Similarity	NPC24043
0.5859	Remote Similarity	NPC482026
0.5833	Remote Similarity	NPC480445
0.5818	Remote Similarity	NPC209550
0.5816	Remote Similarity	NPC64425
0.5743	Remote Similarity	NPC76831
0.573	Remote Similarity	NPC111929
0.573	Remote Similarity	NPC320283
0.573	Remote Similarity	NPC41121
0.5729	Remote Similarity	NPC139320
0.5714	Remote Similarity	NPC219043
0.5714	Remote Similarity	NPC115674
0.5686	Remote Similarity	NPC470449
0.5673	Remote Similarity	NPC203145
0.5667	Remote Similarity	NPC77672
0.5667	Remote Similarity	NPC133671
0.5667	Remote Similarity	NPC135391
0.5667	Remote Similarity	NPC78263
0.5667	Remote Similarity	NPC250069
0.566	Remote Similarity	NPC480441
0.5652	Remote Similarity	NPC216496
0.5652	Remote Similarity	NPC473554
0.5641	Remote Similarity	NPC266960
0.5638	Remote Similarity	NPC116458
0.5638	Remote Similarity	NPC246943
0.5625	Remote Similarity	NPC192539
0.5577	Remote Similarity	NPC470455
0.5577	Remote Similarity	NPC14187
0.5575	Remote Similarity	NPC480472
0.5566	Remote Similarity	NPC48984
0.5566	Remote Similarity	NPC173837
0.5543	Remote Similarity	NPC46420
0.5534	Remote Similarity	NPC470445
0.5514	Remote Similarity	NPC303694
0.551	Remote Similarity	NPC173582
0.551	Remote Similarity	NPC265885
0.551	Remote Similarity	NPC181465
0.551	Remote Similarity	NPC215710
0.551	Remote Similarity	NPC473438
0.551	Remote Similarity	NPC253788
0.55	Remote Similarity	NPC61904
0.55	Remote Similarity	NPC488074
0.5487	Remote Similarity	NPC175429
0.5478	Remote Similarity	NPC21359
0.5478	Remote Similarity	NPC460984
0.5455	Remote Similarity	NPC488734
0.5455	Remote Similarity	NPC65563
0.5455	Remote Similarity	NPC470949
0.5455	Remote Similarity	NPC488735
0.5455	Remote Similarity	NPC488739
0.5455	Remote Similarity	NPC488732
0.5455	Remote Similarity	NPC488738
0.5455	Remote Similarity	NPC605592
0.5446	Remote Similarity	NPC480444
0.5437	Remote Similarity	NPC89127
0.5398	Remote Similarity	NPC138990
0.5385	Remote Similarity	NPC36138
0.5333	Remote Similarity	NPC288084
0.5333	Remote Similarity	NPC470450
0.5327	Remote Similarity	NPC189564
0.5326	Remote Similarity	NPC249281
0.5319	Remote Similarity	NPC472459
0.5312	Remote Similarity	NPC223747
0.5312	Remote Similarity	NPC136761
0.5269	Remote Similarity	NPC297987
0.5269	Remote Similarity	NPC265530
0.5263	Remote Similarity	NPC488737
0.5263	Remote Similarity	NPC219904
0.5258	Remote Similarity	NPC203050
0.5258	Remote Similarity	NPC225434
0.5229	Remote Similarity	NPC470712
0.5229	Remote Similarity	NPC164704
0.5221	Remote Similarity	NPC470717
0.5214	Remote Similarity	NPC480470
0.5213	Remote Similarity	NPC27640
0.5208	Remote Similarity	NPC120099
0.52	Remote Similarity	NPC471748
0.5196	Remote Similarity	NPC472992
0.5185	Remote Similarity	NPC470416
0.5181	Remote Similarity	NPC607702
0.5175	Remote Similarity	NPC470720
0.5161	Remote Similarity	NPC127546
0.5161	Remote Similarity	NPC57625
0.5161	Remote Similarity	NPC173637
0.5161	Remote Similarity	NPC317489
0.5161	Remote Similarity	NPC223424
0.5161	Remote Similarity	NPC600591
0.5152	Remote Similarity	NPC8856
0.5152	Remote Similarity	NPC239549
0.5146	Remote Similarity	NPC483414
0.5143	Remote Similarity	NPC476472
0.5143	Remote Similarity	NPC294815
0.5143	Remote Similarity	NPC16194
0.5133	Remote Similarity	NPC470713
0.5126	Remote Similarity	NPC231787
0.5106	Remote Similarity	NPC145038
0.5106	Remote Similarity	NPC8573
0.5106	Remote Similarity	NPC56077
0.5106	Remote Similarity	NPC281131
0.5106	Remote Similarity	NPC64305
0.5106	Remote Similarity	NPC253662
0.5106	Remote Similarity	NPC179950
0.5106	Remote Similarity	NPC88789
0.5106	Remote Similarity	NPC491374
0.5104	Remote Similarity	NPC488071
0.5102	Remote Similarity	NPC488072
0.51	Remote Similarity	NPC29958
0.5098	Remote Similarity	NPC186816
0.5096	Remote Similarity	NPC473327
0.5088	Remote Similarity	NPC162394
0.5088	Remote Similarity	NPC488740
0.5088	Remote Similarity	NPC488736
0.5088	Remote Similarity	NPC488733
0.5086	Remote Similarity	NPC480443
0.5052	Remote Similarity	NPC609478
0.5049	Remote Similarity	NPC253521
0.5049	Remote Similarity	NPC113836
0.5047	Remote Similarity	NPC470446

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470444 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5593
0.1-0.2	3476
0.2-0.3	71
0.3-0.4	6
0.4-0.5	3
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