NPASS Compound

Natural Product: NPC482197

Natural Product ID	NPC482197
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KYIPVUWVVGXMKA-DAYCDKTJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 90 93 0 0 0 0 0 0 0 0999 V2000 10.9321 -0.7123 -0.2612 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6861 -0.4883 0.5870 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6921 -1.5741 0.2858 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4194 -1.4679 1.0618 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6725 -0.1564 0.7951 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3300 -0.0395 -0.6215 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0965 0.0608 -1.0607 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9552 0.0657 -0.1965 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7281 0.1709 -0.7014 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5441 0.1804 0.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6365 0.0889 1.3930 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3107 0.2897 -0.4178 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9332 0.3113 0.3171 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5528 -1.0150 0.0371 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0043 -1.9756 1.1022 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0577 -0.9310 0.0584 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4958 0.0362 -0.9629 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9595 0.2008 -1.1628 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9905 -0.5009 -0.7743 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9421 -1.7734 0.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8982 -2.5874 -0.5696 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5723 -2.3053 0.0441 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7474 -3.3676 -0.5406 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5498 -4.4118 -0.7793 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1905 -5.7438 -1.3676 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9222 -4.0485 -0.3860 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8298 -4.7854 -0.0087 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9023 -2.3737 -1.9607 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3228 0.0080 -1.1818 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1552 1.1750 -1.9213 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9724 1.4191 -0.6659 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8272 2.0442 -1.3417 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7776 3.5584 -1.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0702 1.3600 -2.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7298 1.5227 0.0678 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7479 2.4536 1.1422 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7059 3.1150 1.6884 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4262 2.9318 1.2333 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9676 4.0548 2.8368 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9102 5.1343 2.3916 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3138 4.7085 3.2910 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3646 -0.3472 1.3170 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8361 -0.5633 0.4001 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9390 -0.0188 -1.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9467 -1.7832 -0.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9595 -0.5149 1.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3213 0.5135 0.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1731 -2.5446 0.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5113 -1.6050 -0.8091 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6149 -1.5212 2.1517 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7593 -2.2873 0.7674 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4208 0.6497 1.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8466 -0.0505 1.4814 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1835 -0.0398 -1.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9718 0.1416 -2.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0100 -0.0121 0.8671 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6502 0.2486 -1.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5876 0.2695 1.3950 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2272 -1.4513 -0.9342 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6099 -1.3782 1.9849 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1023 -2.5171 0.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7438 -2.6373 1.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1146 -0.3340 -1.9621 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1703 1.1119 -1.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6264 -1.4473 1.0711 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9465 -2.1985 0.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7028 -2.6270 1.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6978 -3.3949 -0.7718 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9171 -6.5011 -0.9862 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1478 -6.0216 -1.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2685 -5.7601 -2.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8312 -2.5439 -2.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9581 0.1652 -0.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7888 -0.7932 -1.8270 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8972 1.8021 -1.7127 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7820 2.1694 -0.3969 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0537 3.7702 -2.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5274 4.0529 -0.8578 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7522 3.9599 -1.3571 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0275 1.4995 -2.3872 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3428 1.8166 -3.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2730 0.2959 -2.5652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4516 3.4982 3.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8887 5.0980 2.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0843 5.0436 1.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4575 6.1592 2.5187 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 4.4800 2.6325 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2172 5.8331 3.3220 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5460 4.4100 4.3332 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8033 -0.7274 2.0346 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 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 24 26 1 0 26 27 2 0 21 28 1 6 19 29 1 0 29 30 1 0 17 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 35 36 1 1 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 39 41 1 0 16 42 1 1 35 13 1 0 22 16 1 0 35 31 1 0 26 21 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 7 55 1 0 8 56 1 0 9 57 1 0 13 58 1 1 14 59 1 6 15 60 1 0 15 61 1 0 15 62 1 0 17 63 1 6 18 64 1 0 20 65 1 0 20 66 1 0 22 67 1 1 23 68 1 0 25 69 1 0 25 70 1 0 25 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 30 75 1 0 31 76 1 1 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 39 83 1 0 40 84 1 0 40 85 1 0 40 86 1 0 41 87 1 0 41 88 1 0 41 89 1 0 42 90 1 0 M END

Standard InCHIKey	KYIPVUWVVGXMKA-DAYCDKTJSA-N
Standard InCHI	InChI=1S/C34H48O8/c1-8-9-10-11-12-13-14-15-26(36)41-29-22(5)33(40)24(27-31(6,7)34(27,29)42-30(38)20(2)3)17-23(19-35)18-32(39)25(33)16-21(4)28(32)37/h12-17,20,22,24-25,27,29,35,39-40H,8-11,18-19H2,1-7H3/b13-12-,15-14+/t22-,24+,25-,27-,29-,32-,33-,34-/m1/s1
SMILES	CCCCC/C=CC=CC(=O)O[C@@H]1[C@@H](C)[C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C)C3=O)O)CO)[C@@H]2C(C)(C)[C@]12OC(=O)C(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	584.33	Volume:	614.261 ? Van der Waals volume.
Dense:	0.951	LogP:	3.925 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.921 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.844 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	23.0
TPSA:	130.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.113	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.285	Fsp³:	0.676
MCE-18:	82.281 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.544	Fluc inhibitor:	0.023 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.276	Promiscuous compounds:	0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.217	MDCK Permeability:	-4.919
Pgp-inhibitor:	0.945	Pgp-substrate:	0.579
PAMPA:	0.367 ? 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):	0.036
20% Bioavailability (F20%):	0.946	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.981
Plasma Protein Binding (PPB):	96.289%	Volume Distribution (VD):	0.19
Fu:	3.48% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.599
OATP1B3 inhibitor:	0.549	BCRP inhibitor:	0.002
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.022
CYP2C9-inhibitor:	0.038	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.991
CYP3A4-inhibitor:	0.125	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.968 ? 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):

5.729

Half-life (T1/2):

0.992

ADMET: Toxicity

hERG Blockers:	0.224	hERG Blockers (10um):	0.51
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.12
AMES Toxicity:	0.417	Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.565	Skin Sensitization:	1.0
Carcinogencity:	0.141	Eye Corrosion:	0.046
Eye Irritation:	0.548	Respiratory Toxicity:	0.766
Drug-induced Neurotoxicity:	0.107	Ototoxicity:	0.734
Hematotoxicity:	0.379	Drug-induced Nephrotoxicity:	0.902
Genotoxicity:	0.021	RPMI-8226 Immunitoxicity:	0.168
A549 Cytotoxicity:	0.611	Hek293 Cytotoxicity:	0.634
BCF:	1.025 ? 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:	4.026 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.771 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.951 ? 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
NPO40844	Euphorbia cupanii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181921]

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
EC50	1
Ratio CC50/EC50	1

Activity Type	# Activity
Organism	1
Others	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
NPT20632	Organism	Chikungunya virus	Chikungunya virus	EC50	<	800.0	nM	PMID[31181921]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	>	12.0	n.a.	PMID[31181921]

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 NPC482197 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	17281
0.1-0.2	31240
0.2-0.3	1115
0.3-0.4	102
0.4-0.5	58
0.5-0.6	27
0.6-0.7	20
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC482199
0.9189	High Similarity	NPC482198
0.8378	Intermediate Similarity	NPC145238
0.8243	Intermediate Similarity	NPC484333
0.75	Intermediate Similarity	NPC472397
0.7403	Intermediate Similarity	NPC478999
0.7229	Intermediate Similarity	NPC479001
0.7229	Intermediate Similarity	NPC479002
0.72	Intermediate Similarity	NPC471125
0.716	Intermediate Similarity	NPC482219
0.7105	Intermediate Similarity	NPC145182
0.6951	Remote Similarity	NPC482200
0.6883	Remote Similarity	NPC275696
0.6883	Remote Similarity	NPC255081
0.6842	Remote Similarity	NPC472758
0.68	Remote Similarity	NPC171905
0.6795	Remote Similarity	NPC5991
0.6795	Remote Similarity	NPC196500
0.6795	Remote Similarity	NPC471108
0.6795	Remote Similarity	NPC5989
0.675	Remote Similarity	NPC22628
0.6585	Remote Similarity	NPC482221
0.6543	Remote Similarity	NPC600005
0.6506	Remote Similarity	NPC482220
0.65	Remote Similarity	NPC471126
0.641	Remote Similarity	NPC157252
0.6364	Remote Similarity	NPC601392
0.6296	Remote Similarity	NPC471128
0.6111	Remote Similarity	NPC601559
0.6044	Remote Similarity	NPC283875
0.6024	Remote Similarity	NPC243902
0.5952	Remote Similarity	NPC236918
0.5952	Remote Similarity	NPC156745
0.5926	Remote Similarity	NPC482454
0.5862	Remote Similarity	NPC482222
0.5682	Remote Similarity	NPC153651
0.5667	Remote Similarity	NPC138641
0.5667	Remote Similarity	NPC611243
0.5632	Remote Similarity	NPC472759
0.5618	Remote Similarity	NPC472398
0.5618	Remote Similarity	NPC600915
0.5529	Remote Similarity	NPC485732
0.5529	Remote Similarity	NPC608501
0.5443	Remote Similarity	NPC158523
0.5333	Remote Similarity	NPC472760
0.5333	Remote Similarity	NPC484334
0.5281	Remote Similarity	NPC609983
0.5208	Remote Similarity	NPC22571
0.5165	Remote Similarity	NPC600879
0.5119	Remote Similarity	NPC485736
0.5119	Remote Similarity	NPC277477
0.5119	Remote Similarity	NPC479003
0.5119	Remote Similarity	NPC485735
0.506	Remote Similarity	NPC482406
0.5057	Remote Similarity	NPC488610
0.5053	Remote Similarity	NPC185876
0.5053	Remote Similarity	NPC19336
0.5052	Remote Similarity	NPC603807

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6577
0.1-0.2	2556
0.2-0.3	17
0.3-0.4	0
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