NPASS Compound

Natural Product: NPC128635

Natural Product ID	NPC128635
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QRQNIQMEGHMTGW-MNMACOOLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44257882
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 10.4187 -2.3025 -0.8536 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1673 -2.9302 -0.7305 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9839 -2.2022 -0.6506 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7557 -2.7900 -0.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5958 -2.0367 -0.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6424 -0.6355 -0.4962 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8943 -0.0977 -0.6169 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0552 -0.8376 -0.6945 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4085 0.1418 -0.4135 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4282 1.5136 -0.4531 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2609 2.2767 -0.3756 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2471 3.5264 -0.4089 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0751 1.5809 -0.2562 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1045 0.2059 -0.2207 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8874 -0.4572 -0.0995 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3268 0.1742 -0.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3438 1.5810 -0.0518 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8532 2.2443 -0.1713 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8779 3.6298 -0.2117 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6163 2.3381 0.0348 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1605 2.5494 -1.3508 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6279 2.8776 -1.2445 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8635 3.5910 0.0698 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5113 2.7041 1.2209 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2263 3.4521 2.5034 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0615 4.1764 2.4891 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5067 1.7924 0.9238 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1575 4.7861 0.0387 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4016 1.7228 -1.3510 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9250 1.4620 -2.1856 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5140 -0.5004 0.1045 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7651 -1.8671 0.1625 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3635 -2.2950 1.4895 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3833 -3.4066 1.2875 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4726 -2.7992 0.4304 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8525 -2.2431 -0.7983 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4357 -2.9490 -2.0334 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8157 -2.9466 -2.0182 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5070 -2.3043 -0.9167 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3922 -3.8048 0.1501 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8420 -3.8430 2.5049 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0422 -1.2149 2.0501 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2362 -0.4576 -0.2979 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1944 -3.0623 -1.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6187 -1.7777 0.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4545 -1.5547 -1.6721 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7027 -3.8876 -0.4956 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6236 -2.5183 -0.3578 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0017 0.9708 -0.6557 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0106 -0.3348 -0.7893 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3489 2.0816 -0.5465 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9355 -1.5413 -0.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5580 4.1876 -0.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3521 3.3603 0.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6665 3.4317 -1.8404 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9101 3.5849 -2.0636 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9533 3.8469 0.0805 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4369 2.0913 1.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1004 2.6564 3.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0866 4.0533 2.8374 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5107 4.0861 3.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6859 5.5249 -0.3630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2014 1.8462 -0.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2884 1.6603 -2.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8076 -2.4162 0.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6254 -2.6497 2.2097 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9195 -4.2155 0.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0522 -2.0262 1.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2248 -1.1801 -0.9023 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0508 -2.5082 -2.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1054 -4.0110 -1.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2210 -3.8473 -2.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0732 -3.8702 0.8791 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3910 -4.6916 2.7308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5630 -0.6951 1.4149 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 6 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 22 29 1 0 21 30 1 0 16 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 14 43 1 0 8 3 1 0 43 9 1 0 18 13 1 0 27 20 1 0 39 32 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 5 48 1 0 7 49 1 0 8 50 1 0 10 51 1 0 15 52 1 0 19 53 1 0 20 54 1 1 21 55 1 0 22 56 1 6 23 57 1 1 24 58 1 0 25 59 1 0 25 60 1 0 26 61 1 0 28 62 1 0 29 63 1 0 30 64 1 0 32 65 1 6 33 66 1 0 34 67 1 6 35 68 1 1 36 69 1 0 37 70 1 0 37 71 1 0 38 72 1 0 40 73 1 0 41 74 1 0 42 75 1 0 M END

Standard InCHIKey	QRQNIQMEGHMTGW-MNMACOOLSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-39-11-4-2-10(3-5-11)13-6-12(31)18-14(40-13)7-15(42-28-26(38)24(36)21(33)17(9-30)43-28)19(22(18)34)27-25(37)23(35)20(32)16(8-29)41-27/h2-7,16-17,20-21,23-30,32-38H,8-9H2,1H3/t16?,17?,20-,21-,23+,24+,25?,26?,27+,28-/m1/s1
SMILES	COc1ccc(cc1)c1cc(=O)c2c(cc(c(c2O)[C@H]2C([C@H]([C@@H](C(CO)O2)O)O)O)O[C@H]2C([C@H]([C@@H](C(CO)O2)O)O)O)o1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	0.101 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.175 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.53 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.139	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.667	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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.61	Fluc inhibitor:	0.084 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.899 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.948 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.115	Promiscuous compounds:	0.162

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.409	MDCK Permeability:	-5.161
Pgp-inhibitor:	0.0	Pgp-substrate:	0.933
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):	1.0
20% Bioavailability (F20%):	0.945	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.848
Plasma Protein Binding (PPB):	82.929%	Volume Distribution (VD):	0.112
Fu:	17.044% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.161
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.026
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.324	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.022 ? 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):

2.332

Half-life (T1/2):

4.532

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.102
Human Hepatotoxicity (H-HT):	0.582	Drug-induced Liver Injury (DILI):	0.922
AMES Toxicity:	0.728	Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.059	Skin Sensitization:	0.706
Carcinogencity:	0.156	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.988
Hematotoxicity:	0.124	Drug-induced Nephrotoxicity:	0.384
Genotoxicity:	0.444	RPMI-8226 Immunitoxicity:	0.15
A549 Cytotoxicity:	0.11	Hek293 Cytotoxicity:	0.328
BCF:	0.364 ? 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:	2.915 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.807 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.631 ? 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
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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 NPC128635 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	21651
0.1-0.2	24245
0.2-0.3	2745
0.3-0.4	914
0.4-0.5	231
0.5-0.6	54
0.6-0.7	10
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
0.8333	Intermediate Similarity	NPC602537
0.8214	Intermediate Similarity	NPC607513
0.7356	Intermediate Similarity	NPC603300
0.7229	Intermediate Similarity	NPC10807
0.7229	Intermediate Similarity	NPC161881
0.6905	Remote Similarity	NPC95090
0.6905	Remote Similarity	NPC27408
0.6824	Remote Similarity	NPC186807
0.6786	Remote Similarity	NPC58053
0.6559	Remote Similarity	NPC257566
0.6354	Remote Similarity	NPC150767
0.6044	Remote Similarity	NPC22832
0.6044	Remote Similarity	NPC243930
0.6042	Remote Similarity	NPC606373
0.6023	Remote Similarity	NPC143851
0.5978	Remote Similarity	NPC607707
0.5955	Remote Similarity	NPC93337
0.5934	Remote Similarity	NPC609451
0.5889	Remote Similarity	NPC105025
0.587	Remote Similarity	NPC605067
0.5843	Remote Similarity	NPC39360
0.5843	Remote Similarity	NPC29763
0.5843	Remote Similarity	NPC210003
0.5714	Remote Similarity	NPC304745
0.5714	Remote Similarity	NPC181712
0.5714	Remote Similarity	NPC45638
0.57	Remote Similarity	NPC124155
0.5667	Remote Similarity	NPC45618
0.5652	Remote Similarity	NPC201292
0.5638	Remote Similarity	NPC311830
0.5625	Remote Similarity	NPC472607
0.5604	Remote Similarity	NPC146792
0.5604	Remote Similarity	NPC189142
0.5604	Remote Similarity	NPC77660
0.5543	Remote Similarity	NPC610763
0.5495	Remote Similarity	NPC261866
0.5474	Remote Similarity	NPC88023
0.5474	Remote Similarity	NPC309025
0.5474	Remote Similarity	NPC602805
0.5437	Remote Similarity	NPC475382
0.5376	Remote Similarity	NPC58716
0.5368	Remote Similarity	NPC601144
0.5361	Remote Similarity	NPC211594
0.5319	Remote Similarity	NPC182045
0.5312	Remote Similarity	NPC111249
0.5288	Remote Similarity	NPC256760
0.5275	Remote Similarity	NPC328740
0.5275	Remote Similarity	NPC289774
0.5269	Remote Similarity	NPC168822
0.5263	Remote Similarity	NPC191306
0.5208	Remote Similarity	NPC284960
0.5208	Remote Similarity	NPC80188
0.5208	Remote Similarity	NPC486578
0.5161	Remote Similarity	NPC289667
0.5161	Remote Similarity	NPC110349
0.5158	Remote Similarity	NPC472459
0.5155	Remote Similarity	NPC220169
0.5149	Remote Similarity	NPC22062
0.5149	Remote Similarity	NPC473634
0.5149	Remote Similarity	NPC138811
0.5106	Remote Similarity	NPC259152
0.5098	Remote Similarity	NPC204693
0.5098	Remote Similarity	NPC131745
0.5096	Remote Similarity	NPC483707
0.5054	Remote Similarity	NPC53545
0.5052	Remote Similarity	NPC148710
0.505	Remote Similarity	NPC47923
0.5049	Remote Similarity	NPC46202
0.5048	Remote Similarity	NPC488089

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC128635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4933
0.1-0.2	4126
0.2-0.3	70
0.3-0.4	17
0.4-0.5	4
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