NPASS Compound

Natural Product: NPC64435

Natural Product ID	NPC64435
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HZJDPVVMWCISAC-RDJJTCITSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102004832
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 -6.4100 0.1508 -2.2223 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0585 -0.2399 -0.8113 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1369 -1.1209 -0.2149 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4557 -2.1268 0.6964 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3729 -1.4331 1.4638 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3122 -0.9133 0.5521 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8636 0.3432 0.8982 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4800 0.3311 1.1162 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9868 1.7216 1.4927 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4430 2.6626 0.4327 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5990 2.6907 -0.7947 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1699 2.8996 -0.3665 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1958 1.8342 0.6490 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2449 0.6145 -0.0141 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3848 -0.1237 -0.2330 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6442 0.2611 0.1686 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7836 -0.5109 -0.0681 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6343 -1.7066 -0.7317 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7456 -2.4619 -0.9639 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6573 -3.5500 -1.5602 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9686 -1.9602 -0.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0729 -0.7599 0.1530 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3286 -0.2032 0.6450 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3438 1.0326 1.3029 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4966 1.5852 1.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6951 0.9179 1.6091 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7237 -0.2932 0.9710 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5219 -0.8379 0.4946 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8863 1.4434 2.0738 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9515 -0.0834 0.3417 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3714 -2.1128 -1.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2729 -1.3389 -0.9012 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0202 -1.7377 -1.3094 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4544 -1.3752 -2.5822 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2766 -3.3229 -1.8078 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6522 1.7304 1.7102 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0844 4.1782 0.0922 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6655 1.4752 -1.4711 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6244 3.9082 1.0088 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8096 -0.8561 -0.7449 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8015 -2.2659 2.4259 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9209 -3.1218 -0.1117 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0157 -0.3187 0.4874 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9953 -0.6260 -2.9006 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5160 0.2182 -2.3106 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9241 1.1414 -2.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0026 0.6785 -0.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7027 -1.6749 -0.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2039 -2.6001 1.3635 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8422 -0.5930 2.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4306 -1.6005 0.5473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3294 -0.2969 2.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9297 -0.0618 0.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4909 1.9186 2.4777 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4746 2.3206 0.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9502 3.4922 -1.4811 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5295 2.7319 -1.2358 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2029 2.1758 1.0418 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8206 1.1860 0.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8356 -2.5480 -0.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3760 1.5131 1.4072 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4441 2.5421 2.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6232 -0.8681 0.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5632 -1.8006 -0.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1707 2.3458 1.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3579 -2.2246 -3.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5364 -1.1034 -2.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0656 -0.5240 -3.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4474 -3.6159 -2.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2997 4.2080 1.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0823 1.4400 -2.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4634 4.3478 0.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9534 -2.6024 2.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2975 -3.9982 0.0914 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9674 -0.5273 0.2614 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 22 30 1 0 18 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 31 35 1 0 13 36 1 0 12 37 1 0 11 38 1 0 10 39 1 0 6 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 40 2 1 0 36 9 1 0 32 15 1 0 30 17 1 0 28 23 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 1 3 48 1 6 4 49 1 1 5 50 1 1 6 51 1 6 8 52 1 0 8 53 1 0 9 54 1 1 10 55 1 6 11 56 1 6 12 57 1 6 13 58 1 1 16 59 1 0 21 60 1 0 24 61 1 0 25 62 1 0 27 63 1 0 28 64 1 0 29 65 1 0 34 66 1 0 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	HZJDPVVMWCISAC-RDJJTCITSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-10-19(31)22(34)24(36)27(40-10)39-9-17-20(32)23(35)25(37)28(43-17)42-16-8-15-18(21(33)26(16)38-2)13(30)7-14(41-15)11-3-5-12(29)6-4-11/h3-8,10,17,19-20,22-25,27-29,31-37H,9H2,1-2H3/t10-,17+,19-,20+,22+,23-,24+,25+,27+,28+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc4c(c(=O)cc(c5ccc(cc5)O)o4)c(c3OC)O)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:	0.557 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.025 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.763 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	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:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.708	Fsp³:	0.464
MCE-18:	118.585 ? 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:	0.579	Fluc inhibitor:	0.267 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.843 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.675 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.057	Promiscuous compounds:	0.425

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.288	MDCK Permeability:	-5.305
Pgp-inhibitor:	0.001	Pgp-substrate:	0.884
PAMPA:	0.998 ? 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):	0.411
20% Bioavailability (F20%):	0.17	30% Bioavailability (F30%):	0.904
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.29
Plasma Protein Binding (PPB):	84.567%	Volume Distribution (VD):	-0.012
Fu:	12.65% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.191
BSEP inhibitor:	0.011

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:	0.011
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.983
HLM stability:	0.006 ? 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):

1.621

Half-life (T1/2):

4.217

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.17
Human Hepatotoxicity (H-HT):	0.349	Drug-induced Liver Injury (DILI):	0.795
AMES Toxicity:	0.808	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.037	Skin Sensitization:	0.942
Carcinogencity:	0.052	Eye Corrosion:	0.0
Eye Irritation:	0.125	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.935
Hematotoxicity:	0.065	Drug-induced Nephrotoxicity:	0.28
Genotoxicity:	0.719	RPMI-8226 Immunitoxicity:	0.156
A549 Cytotoxicity:	0.248	Hek293 Cytotoxicity:	0.551
BCF:	0.379 ? 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:	2.892 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.392 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.504 ? 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
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21899269]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20096	Cirsium japonicum	Species	Asteraceae	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 NPC64435 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	17219
0.1-0.2	28262
0.2-0.3	3288
0.3-0.4	667
0.4-0.5	288
0.5-0.6	88
0.6-0.7	28
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.878	High Similarity	NPC204693
0.7882	Intermediate Similarity	NPC44931
0.7738	Intermediate Similarity	NPC172807
0.7326	Intermediate Similarity	NPC211594
0.7253	Intermediate Similarity	NPC483707
0.7229	Intermediate Similarity	NPC105025
0.7191	Intermediate Similarity	NPC22062
0.7191	Intermediate Similarity	NPC473634
0.7191	Intermediate Similarity	NPC138811
0.7093	Intermediate Similarity	NPC99957
0.7	Intermediate Similarity	NPC210073
0.6854	Remote Similarity	NPC254540
0.6706	Remote Similarity	NPC93337
0.6702	Remote Similarity	NPC209296
0.6559	Remote Similarity	NPC473571
0.6559	Remote Similarity	NPC110941
0.6495	Remote Similarity	NPC101636
0.6452	Remote Similarity	NPC473512
0.6452	Remote Similarity	NPC129827
0.6383	Remote Similarity	NPC186816
0.6364	Remote Similarity	NPC201292
0.6279	Remote Similarity	NPC331652
0.625	Remote Similarity	NPC186807
0.6224	Remote Similarity	NPC473073
0.617	Remote Similarity	NPC173582
0.617	Remote Similarity	NPC265885
0.617	Remote Similarity	NPC181465
0.617	Remote Similarity	NPC215710
0.617	Remote Similarity	NPC473438
0.617	Remote Similarity	NPC253788
0.6154	Remote Similarity	NPC602805
0.6146	Remote Similarity	NPC475366
0.6105	Remote Similarity	NPC65563
0.6105	Remote Similarity	NPC470949
0.6082	Remote Similarity	NPC470443
0.6023	Remote Similarity	NPC58053
0.602	Remote Similarity	NPC473623
0.6	Remote Similarity	NPC298171
0.6	Remote Similarity	NPC67105
0.5979	Remote Similarity	NPC126784
0.5979	Remote Similarity	NPC241423
0.596	Remote Similarity	NPC488089
0.5938	Remote Similarity	NPC233994
0.5889	Remote Similarity	NPC45638
0.5825	Remote Similarity	NPC11468
0.5816	Remote Similarity	NPC64051
0.5773	Remote Similarity	NPC203259
0.5773	Remote Similarity	NPC33054
0.5773	Remote Similarity	NPC176740
0.5773	Remote Similarity	NPC471725
0.5773	Remote Similarity	NPC134532
0.5773	Remote Similarity	NPC602582
0.5769	Remote Similarity	NPC120163
0.5761	Remote Similarity	NPC609451
0.5758	Remote Similarity	NPC211532
0.5758	Remote Similarity	NPC488364
0.5743	Remote Similarity	NPC476472
0.5743	Remote Similarity	NPC294815
0.5743	Remote Similarity	NPC16194
0.5729	Remote Similarity	NPC187379
0.5688	Remote Similarity	NPC298666
0.5652	Remote Similarity	NPC27942
0.5644	Remote Similarity	NPC142142
0.5644	Remote Similarity	NPC270675
0.5644	Remote Similarity	NPC195685
0.5612	Remote Similarity	NPC303913
0.56	Remote Similarity	NPC65711
0.5567	Remote Similarity	NPC295613
0.5567	Remote Similarity	NPC473657
0.5566	Remote Similarity	NPC472993
0.5545	Remote Similarity	NPC473327
0.5543	Remote Similarity	NPC27640
0.5532	Remote Similarity	NPC605067
0.5514	Remote Similarity	NPC473644
0.551	Remote Similarity	NPC15358
0.551	Remote Similarity	NPC227508
0.5495	Remote Similarity	NPC39360
0.5495	Remote Similarity	NPC19709
0.5495	Remote Similarity	NPC29763
0.5495	Remote Similarity	NPC210003
0.5481	Remote Similarity	NPC472994
0.5463	Remote Similarity	NPC311850
0.5455	Remote Similarity	NPC65003
0.5435	Remote Similarity	NPC146792
0.5385	Remote Similarity	NPC114740
0.5385	Remote Similarity	NPC470449
0.5376	Remote Similarity	NPC46420
0.5376	Remote Similarity	NPC24043
0.537	Remote Similarity	NPC25523
0.5368	Remote Similarity	NPC181616
0.5354	Remote Similarity	NPC39834
0.5347	Remote Similarity	NPC46202
0.5347	Remote Similarity	NPC284277
0.5347	Remote Similarity	NPC475497
0.5319	Remote Similarity	NPC117260
0.5315	Remote Similarity	NPC68592
0.5294	Remote Similarity	NPC469622
0.5294	Remote Similarity	NPC483415
0.5288	Remote Similarity	NPC470447
0.5253	Remote Similarity	NPC471079
0.5243	Remote Similarity	NPC483416
0.5243	Remote Similarity	NPC229409
0.5217	Remote Similarity	NPC473043
0.5213	Remote Similarity	NPC610763
0.5204	Remote Similarity	NPC477848
0.52	Remote Similarity	NPC47923
0.5196	Remote Similarity	NPC488073
0.5196	Remote Similarity	NPC488074
0.5172	Remote Similarity	NPC262222
0.5161	Remote Similarity	NPC108831
0.5161	Remote Similarity	NPC182634
0.5149	Remote Similarity	NPC475155
0.5146	Remote Similarity	NPC12013
0.5146	Remote Similarity	NPC483414
0.5146	Remote Similarity	NPC11432
0.5146	Remote Similarity	NPC477613
0.5143	Remote Similarity	NPC475382
0.5143	Remote Similarity	NPC477629
0.5133	Remote Similarity	NPC198199
0.5106	Remote Similarity	NPC259152
0.5104	Remote Similarity	NPC488071
0.5053	Remote Similarity	NPC181712
0.5052	Remote Similarity	NPC606560
0.5049	Remote Similarity	NPC606547
0.5047	Remote Similarity	NPC135358
0.5046	Remote Similarity	NPC189564
0.5044	Remote Similarity	NPC488086

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC64435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5053
0.1-0.2	4017
0.2-0.3	68
0.3-0.4	7
0.4-0.5	0
0.5-0.6	4
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
0.6702	Remote Similarity	NPD7054	Phase 4
0.5825	Remote Similarity	NPD7472	Pre-clinical
0.5773	Remote Similarity	NPD6797	Phase 2
0.5588	Remote Similarity	NPD7251	Phase 2
0.5234	Remote Similarity	NPD7808	Phase 3

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