NPASS Compound

Natural Product: NPC28192

Natural Product ID	NPC28192
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PLKFSXFJGNZAER-HCGIPUGESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325466
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 70 73 0 0 0 0 0 0 0 0999 V2000 5.9145 2.0624 -2.4398 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8199 1.3354 -1.7446 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9008 0.8434 -0.5366 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1768 1.0210 0.1987 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7575 0.1483 0.0444 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7882 -0.3443 1.2060 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5663 -0.0153 -0.6421 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4313 -0.6809 -0.1218 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1080 -1.9442 -0.8769 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0458 -3.1058 0.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0158 -1.9094 -1.8148 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4525 -2.3185 -3.2220 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1830 -2.8477 -1.5242 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9915 -2.3231 -0.3967 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9386 -3.2128 -0.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7898 -2.9380 1.0278 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6798 -1.7340 1.7454 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7180 -0.8111 1.3955 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9115 -1.1301 0.3374 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0796 0.0699 0.1821 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2981 0.2506 0.0338 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7572 1.5409 -0.0171 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1256 2.6021 0.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5098 2.3718 0.2212 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9960 1.0901 0.2722 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3194 0.7526 0.3876 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2044 0.5836 -0.7041 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3861 3.4187 0.3134 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6937 3.9414 1.5918 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3491 3.8926 0.0260 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7348 4.1112 -0.1200 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4877 0.3877 2.0250 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6013 0.5394 3.1188 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6370 -1.7141 2.7411 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4067 -2.8896 2.6399 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8291 -3.6524 1.6001 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7436 2.2517 -1.7399 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2807 1.5269 -3.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4891 3.0610 -2.7142 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8738 1.2043 -2.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3560 2.0912 0.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9769 0.6338 -0.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2442 0.3769 1.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7476 -1.0066 0.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0493 -2.1581 -1.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9623 -3.1153 0.7567 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0945 -4.0716 -0.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1986 -3.0274 0.7876 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3548 -0.8558 -1.9567 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9583 -3.2882 -3.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4772 -2.4664 -3.8078 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1111 -1.5350 -3.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8106 -2.9927 -2.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7407 -3.8373 -1.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0180 -4.1478 -0.5937 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8393 1.7380 -0.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9786 -0.3960 -1.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2515 0.5761 -0.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9489 1.3339 -1.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9342 4.7056 1.8792 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7074 4.4208 1.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7587 3.1444 2.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2933 3.7906 0.7848 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1441 3.5855 -1.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9756 5.1885 -0.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9560 1.4113 2.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1562 0.8180 4.0394 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9679 -0.3417 3.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4380 -2.5583 2.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4359 -3.4523 3.5983 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 11 13 1 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 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 24 28 1 0 28 29 1 0 23 30 1 0 30 31 1 0 18 32 1 0 32 33 1 0 17 34 1 0 34 35 1 0 35 36 1 0 21 8 1 0 19 14 1 0 25 20 1 0 36 16 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 4 41 1 0 4 42 1 0 4 43 1 0 8 44 1 0 9 45 1 6 10 46 1 0 10 47 1 0 10 48 1 0 11 49 1 6 12 50 1 0 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 15 55 1 0 22 56 1 0 27 57 1 0 27 58 1 0 27 59 1 0 29 60 1 0 29 61 1 0 29 62 1 0 31 63 1 0 31 64 1 0 31 65 1 0 33 66 1 0 33 67 1 0 33 68 1 0 35 69 1 0 35 70 1 0 M END

Standard InCHIKey	PLKFSXFJGNZAER-HCGIPUGESA-N
Standard InCHI	InChI=1S/C28H34O8/c1-9-14(2)28(29)36-23-16(4)15(3)10-17-11-20-25(35-13-34-20)26(32-7)21(17)22-18(23)12-19(30-5)24(31-6)27(22)33-8/h9,11-12,15-16,23H,10,13H2,1-8H3/b14-9+/t15-,16-,23?/m0/s1
SMILES	C/C=C(C)/C(=O)OC1[C@@H](C)[C@@H](C)Cc2cc3c(c(c2-c2c1cc(c(c2OC)OC)OC)OC)OCO3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.23	Volume:	507.848 ? Van der Waals volume.
Dense:	0.981	LogP:	3.427 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.426 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.229 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	24.0
TPSA:	81.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.382	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.065	Fsp³:	0.464
MCE-18:	87.585 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.484	Fluc inhibitor:	0.309 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.381 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.615 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.232	Promiscuous compounds:	0.16

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.072	MDCK Permeability:	-4.805
Pgp-inhibitor:	0.868	Pgp-substrate:	0.025
PAMPA:	0.039 ? 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):	0.0
20% Bioavailability (F20%):	0.212	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.804

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.887	MRP1:	0.996
Plasma Protein Binding (PPB):	97.27%	Volume Distribution (VD):	0.149
Fu:	2.632% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.973
OATP1B3 inhibitor:	0.956	BCRP inhibitor:	0.018
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.991
CYP2C9-inhibitor:	0.73	CYP2C9-substrate:	0.44
CYP2D6-inhibitor:	0.389	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.698	CYP2C8-inhibitor:	0.391
HLM stability:	0.978 ? 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):

4.725

Half-life (T1/2):

0.734

ADMET: Toxicity

hERG Blockers:	0.165	hERG Blockers (10um):	0.539
Human Hepatotoxicity (H-HT):	0.592	Drug-induced Liver Injury (DILI):	0.83
AMES Toxicity:	0.528	Rat Oral Acute Toxicity:	0.458
Maximum Recommended Daily Dose:	0.709	Skin Sensitization:	0.793
Carcinogencity:	0.906	Eye Corrosion:	0.0
Eye Irritation:	0.114	Respiratory Toxicity:	0.57
Drug-induced Neurotoxicity:	0.824	Ototoxicity:	0.574
Hematotoxicity:	0.732	Drug-induced Nephrotoxicity:	0.813
Genotoxicity:	0.855	RPMI-8226 Immunitoxicity:	0.343
A549 Cytotoxicity:	0.449	Hek293 Cytotoxicity:	0.714
BCF:	1.828 ? 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:	4.027 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.66 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.875 ? 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
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	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 NPC28192 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	19960
0.1-0.2	28170
0.2-0.3	1443
0.3-0.4	165
0.4-0.5	31
0.5-0.6	42
0.6-0.7	21
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9636	High Similarity	NPC85141
0.8421	Intermediate Similarity	NPC76415
0.8421	Intermediate Similarity	NPC218510
0.7759	Intermediate Similarity	NPC327352
0.7759	Intermediate Similarity	NPC198129
0.7759	Intermediate Similarity	NPC252281
0.75	Intermediate Similarity	NPC322426
0.7463	Intermediate Similarity	NPC476065
0.7258	Intermediate Similarity	NPC316989
0.7193	Intermediate Similarity	NPC865
0.7101	Intermediate Similarity	NPC475229
0.7015	Intermediate Similarity	NPC126405
0.7015	Intermediate Similarity	NPC53669
0.7015	Intermediate Similarity	NPC77237
0.7015	Intermediate Similarity	NPC297271
0.7015	Intermediate Similarity	NPC16791
0.7015	Intermediate Similarity	NPC217708
0.6857	Remote Similarity	NPC63061
0.6716	Remote Similarity	NPC198461
0.6716	Remote Similarity	NPC24562
0.6567	Remote Similarity	NPC471154
0.6552	Remote Similarity	NPC326144
0.6522	Remote Similarity	NPC477885
0.6429	Remote Similarity	NPC145722
0.6429	Remote Similarity	NPC256776
0.6429	Remote Similarity	NPC185680
0.6418	Remote Similarity	NPC312763
0.6338	Remote Similarity	NPC475756
0.6324	Remote Similarity	NPC191352
0.629	Remote Similarity	NPC318286
0.6167	Remote Similarity	NPC141493
0.6129	Remote Similarity	NPC327651
0.6094	Remote Similarity	NPC321958
0.6087	Remote Similarity	NPC308739
0.6071	Remote Similarity	NPC32189
0.6034	Remote Similarity	NPC216434
0.6034	Remote Similarity	NPC103448
0.6034	Remote Similarity	NPC606558
0.597	Remote Similarity	NPC295297
0.5968	Remote Similarity	NPC184928
0.5946	Remote Similarity	NPC474606
0.5938	Remote Similarity	NPC220577
0.5921	Remote Similarity	NPC348849
0.5921	Remote Similarity	NPC238834
0.5921	Remote Similarity	NPC178195
0.5897	Remote Similarity	NPC215400
0.5846	Remote Similarity	NPC321696
0.5833	Remote Similarity	NPC224472
0.5714	Remote Similarity	NPC154971
0.5714	Remote Similarity	NPC121661
0.5694	Remote Similarity	NPC473323
0.569	Remote Similarity	NPC474295
0.5672	Remote Similarity	NPC325122
0.5652	Remote Similarity	NPC73467
0.5571	Remote Similarity	NPC252286
0.5507	Remote Similarity	NPC325720
0.5507	Remote Similarity	NPC316676
0.5479	Remote Similarity	NPC477380
0.5432	Remote Similarity	NPC230531
0.5385	Remote Similarity	NPC53722
0.5385	Remote Similarity	NPC201404
0.5385	Remote Similarity	NPC290714
0.5373	Remote Similarity	NPC304821
0.5373	Remote Similarity	NPC230538
0.5373	Remote Similarity	NPC229172
0.5373	Remote Similarity	NPC103637
0.5373	Remote Similarity	NPC36531
0.5352	Remote Similarity	NPC319749
0.5316	Remote Similarity	NPC485504
0.5286	Remote Similarity	NPC474393
0.5286	Remote Similarity	NPC474347
0.527	Remote Similarity	NPC470916
0.5256	Remote Similarity	NPC29727
0.5217	Remote Similarity	NPC473989
0.5195	Remote Similarity	NPC475592
0.5128	Remote Similarity	NPC483406
0.5075	Remote Similarity	NPC172171
0.5075	Remote Similarity	NPC239254
0.5065	Remote Similarity	NPC280778
0.5062	Remote Similarity	NPC311912

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC28192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5218
0.1-0.2	3867
0.2-0.3	64
0.3-0.4	1
0.4-0.5	0
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