NPASS Compound

Natural Product: NPC480915

Natural Product ID	NPC480915
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DIUAVTQCLBTMJM-NRJNKQAOSA-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 81 86 0 0 0 0 0 0 0 0999 V2000 7.4657 0.8182 -1.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6707 1.1473 -0.6516 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3595 0.4334 0.4918 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9346 -1.0103 0.5184 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4292 -1.0949 0.6338 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7676 0.2258 0.3051 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3772 0.7308 -0.8417 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4175 0.0697 0.0076 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6008 0.8767 0.7827 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6995 0.0746 1.6889 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2434 0.1813 1.3224 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4754 -0.9482 2.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9794 -0.9343 1.6775 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0737 -1.0632 0.1980 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4894 0.2343 -0.3716 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9002 0.3305 -1.8043 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3865 0.6243 -1.8066 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1892 -0.3986 -1.0458 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1014 -1.0652 -2.0519 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9018 0.1700 0.1291 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3539 -1.0666 0.8727 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3447 -2.1428 0.4846 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3344 -1.4816 -0.4135 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0517 -2.3987 -1.4403 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0016 1.1199 -0.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0232 2.3700 0.2651 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2034 3.0378 -0.1815 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5329 4.2531 0.0624 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9162 2.1319 -0.9204 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2231 0.9281 -0.9588 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0054 0.1988 -0.1669 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7023 1.3572 -0.7904 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8443 1.9061 -0.0113 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4806 2.9399 0.8606 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5162 -1.0471 -0.8186 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0490 -1.9505 -0.2389 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1388 -1.5075 1.9328 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5491 -1.5932 1.6298 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1253 1.0795 1.6920 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9400 1.1486 -2.8222 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3987 1.4157 -1.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7725 -0.2494 -1.9373 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7432 2.2595 -0.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4748 0.4271 0.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3121 -1.5064 -0.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0909 -1.8217 -0.1363 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8689 0.9705 1.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2885 1.4554 1.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0718 -0.9890 1.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7878 0.3744 2.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 1.1390 1.7236 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4178 -0.7521 3.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0279 -1.9257 1.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3373 -0.0080 2.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3966 -1.7736 2.2575 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2788 -1.8325 -0.0654 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8770 1.0732 0.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4070 1.1741 -2.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7619 -0.6260 -2.3571 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7795 0.8245 -2.8180 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5041 1.5953 -1.2455 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0609 -1.3987 -1.6153 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2052 -0.4609 -2.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6018 -1.9955 -2.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1608 0.6599 0.7612 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3800 -1.3161 0.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3120 -0.9377 1.9682 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9454 -2.6954 1.3250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9432 -2.8900 -0.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2565 -3.3146 -1.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2482 2.8358 0.8841 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0156 0.7357 -2.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8989 0.1533 -0.5340 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0012 1.0797 -1.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0444 2.1750 -0.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5745 2.3543 -0.7305 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0653 2.9604 1.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3862 -1.1202 -1.8930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7549 -1.0438 2.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1744 -2.4868 1.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3898 2.0318 1.5601 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 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 20 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 15 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 31 35 1 6 35 36 2 0 5 37 1 0 4 38 1 0 3 39 1 0 7 2 1 0 33 9 1 0 31 11 1 0 23 14 1 0 30 25 1 0 23 18 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 1 3 44 1 6 4 45 1 6 5 46 1 6 6 47 1 1 9 48 1 1 10 49 1 0 10 50 1 0 11 51 1 1 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 6 15 57 1 1 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 19 62 1 0 19 63 1 0 19 64 1 0 20 65 1 1 21 66 1 0 21 67 1 0 22 68 1 0 22 69 1 0 24 70 1 0 26 71 1 0 30 72 1 0 30 73 1 0 32 74 1 0 32 75 1 0 33 76 1 6 34 77 1 0 35 78 1 0 37 79 1 0 38 80 1 0 39 81 1 0 M END

Standard InCHIKey	DIUAVTQCLBTMJM-NRJNKQAOSA-N
Standard InCHI	InChI=1S/C29H42O10/c1-14-23(33)24(34)25(35)26(38-14)39-21-10-16-3-4-19-18(28(16,13-30)11-20(21)31)5-7-27(2)17(6-8-29(19,27)36)15-9-22(32)37-12-15/h9,13-14,16-21,23-26,31,33-36H,3-8,10-12H2,1-2H3/t14-,16+,17-,18+,19-,20-,21-,23-,24-,25-,26+,27-,28-,29+/m1/s1
SMILES	C[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@H](CC[C@]34O)C3=CC(=O)OC3)[C@]2(C[C@H]1O)C=O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	550.28	Volume:	538.794 ? Van der Waals volume.
Dense:	1.021	LogP:	-0.288 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.657 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.324 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	162.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.19	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.395	Fsp³:	0.862
MCE-18:	114.074 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.768	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.144	Promiscuous compounds:	0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.241	MDCK Permeability:	-5.238
Pgp-inhibitor:	0.0	Pgp-substrate:	0.975
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):	0.056
20% Bioavailability (F20%):	0.921	30% Bioavailability (F30%):	0.728
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122	MRP1:	0.978
Plasma Protein Binding (PPB):	73.98%	Volume Distribution (VD):	-0.459
Fu:	24.975% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.822
OATP1B3 inhibitor:	0.684	BCRP inhibitor:	0.005
BSEP inhibitor:	0.048

ADMET: Metabolism

CYP1A2-inhibitor:	0.214	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.109	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.033	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.04
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.45
HLM stability:	0.0 ? 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):

1.076

Half-life (T1/2):

3.56

ADMET: Toxicity

hERG Blockers:	0.041	hERG Blockers (10um):	0.275
Human Hepatotoxicity (H-HT):	0.723	Drug-induced Liver Injury (DILI):	0.687
AMES Toxicity:	0.965	Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.856	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.984
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.789
Hematotoxicity:	0.923	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.935
A549 Cytotoxicity:	0.731	Hek293 Cytotoxicity:	0.971
BCF:	0.597 ? 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:	3.242 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.66 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.095 ? 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
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933890]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	root	n.a.	PMID[19052526]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28817274]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31967821]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32649211]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548837]
NPO30295	Calotropis gigantea	Species	Apocynaceae	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
IC50	3
Ratio IC50	1
EC50	1

Activity Type	# Activity
Cell line	3
Others	2

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
NPT457	Cell line	BT-549	Homo sapiens	IC50	=	1400.0	nM	PMID[32649211]
NPT402	Cell line	Hs-578T	Homo sapiens	IC50	=	3900.0	nM	PMID[32649211]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	10000.0	nM	PMID[32649211]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	7.0	n.a.	PMID[32649211]
NPT2	Others	Unspecified	n.a.	EC50	=	2500.0	nM	PMID[32649211]

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 NPC480915 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	13303
0.1-0.2	31145
0.2-0.3	4942
0.3-0.4	233
0.4-0.5	86
0.5-0.6	98
0.6-0.7	37
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8158	Intermediate Similarity	NPC469750
0.7436	Intermediate Similarity	NPC99620
0.716	Intermediate Similarity	NPC76572
0.716	Intermediate Similarity	NPC193382
0.716	Intermediate Similarity	NPC480914
0.7125	Intermediate Similarity	NPC196429
0.7073	Intermediate Similarity	NPC88668
0.6829	Remote Similarity	NPC17896
0.6829	Remote Similarity	NPC469755
0.6829	Remote Similarity	NPC284406
0.6829	Remote Similarity	NPC197707
0.6829	Remote Similarity	NPC251866
0.6627	Remote Similarity	NPC5311
0.6588	Remote Similarity	NPC179412
0.6588	Remote Similarity	NPC471356
0.6585	Remote Similarity	NPC99728
0.6585	Remote Similarity	NPC87250
0.6585	Remote Similarity	NPC244402
0.6585	Remote Similarity	NPC50305
0.6517	Remote Similarity	NPC188234
0.6517	Remote Similarity	NPC240070
0.6429	Remote Similarity	NPC157376
0.6429	Remote Similarity	NPC77299
0.6429	Remote Similarity	NPC480906
0.6429	Remote Similarity	NPC142066
0.6429	Remote Similarity	NPC603972
0.6374	Remote Similarity	NPC125077
0.6304	Remote Similarity	NPC232785
0.6304	Remote Similarity	NPC486139
0.6279	Remote Similarity	NPC250556
0.6237	Remote Similarity	NPC329986
0.6237	Remote Similarity	NPC140092
0.619	Remote Similarity	NPC471633
0.6184	Remote Similarity	NPC196931
0.617	Remote Similarity	NPC486138
0.617	Remote Similarity	NPC276838
0.6118	Remote Similarity	NPC309034
0.6111	Remote Similarity	NPC30483
0.6111	Remote Similarity	NPC470897
0.6067	Remote Similarity	NPC480907
0.6044	Remote Similarity	NPC236973
0.6044	Remote Similarity	NPC292467
0.6023	Remote Similarity	NPC471353
0.6023	Remote Similarity	NPC277374
0.5938	Remote Similarity	NPC476221
0.5938	Remote Similarity	NPC477709
0.5889	Remote Similarity	NPC72260
0.587	Remote Similarity	NPC32177
0.587	Remote Similarity	NPC27363
0.587	Remote Similarity	NPC469756
0.587	Remote Similarity	NPC275901
0.5851	Remote Similarity	NPC486143
0.5851	Remote Similarity	NPC486142
0.5851	Remote Similarity	NPC486149
0.5814	Remote Similarity	NPC473852
0.5806	Remote Similarity	NPC480910
0.5806	Remote Similarity	NPC480909
0.5795	Remote Similarity	NPC199428
0.5795	Remote Similarity	NPC84949
0.5795	Remote Similarity	NPC109448
0.5795	Remote Similarity	NPC480562
0.5795	Remote Similarity	NPC74945
0.5795	Remote Similarity	NPC310341
0.5795	Remote Similarity	NPC31354
0.5795	Remote Similarity	NPC24839
0.5795	Remote Similarity	NPC69576
0.5795	Remote Similarity	NPC604978
0.5747	Remote Similarity	NPC84987
0.5743	Remote Similarity	NPC486150
0.573	Remote Similarity	NPC77319
0.573	Remote Similarity	NPC471351
0.573	Remote Similarity	NPC471355
0.5729	Remote Similarity	NPC486146
0.5684	Remote Similarity	NPC486135
0.5684	Remote Similarity	NPC486137
0.5667	Remote Similarity	NPC9499
0.5667	Remote Similarity	NPC471360
0.5667	Remote Similarity	NPC469751
0.5667	Remote Similarity	NPC471361
0.5667	Remote Similarity	NPC86159
0.5667	Remote Similarity	NPC469752
0.5667	Remote Similarity	NPC469754
0.5667	Remote Similarity	NPC70542
0.5625	Remote Similarity	NPC469749
0.5579	Remote Similarity	NPC610296
0.5568	Remote Similarity	NPC219085
0.5556	Remote Similarity	NPC253456
0.5556	Remote Similarity	NPC159338
0.55	Remote Similarity	NPC486144
0.55	Remote Similarity	NPC486145
0.55	Remote Similarity	NPC486147
0.55	Remote Similarity	NPC475590
0.55	Remote Similarity	NPC486148
0.5495	Remote Similarity	NPC483822
0.5495	Remote Similarity	NPC305574
0.5474	Remote Similarity	NPC32793
0.5474	Remote Similarity	NPC116075
0.5443	Remote Similarity	NPC268829
0.5443	Remote Similarity	NPC295110
0.5392	Remote Similarity	NPC120390
0.5392	Remote Similarity	NPC74259
0.5392	Remote Similarity	NPC475419
0.5385	Remote Similarity	NPC171619
0.5376	Remote Similarity	NPC488161
0.5376	Remote Similarity	NPC16569
0.5347	Remote Similarity	NPC486136
0.5341	Remote Similarity	NPC158344
0.5341	Remote Similarity	NPC474418
0.534	Remote Similarity	NPC474908
0.534	Remote Similarity	NPC486134
0.534	Remote Similarity	NPC486141
0.5326	Remote Similarity	NPC484202
0.5326	Remote Similarity	NPC93883
0.5309	Remote Similarity	NPC222875
0.5309	Remote Similarity	NPC25177
0.5275	Remote Similarity	NPC243196
0.5275	Remote Similarity	NPC10823
0.5269	Remote Similarity	NPC471354
0.5269	Remote Similarity	NPC27507
0.5253	Remote Similarity	NPC146857
0.5253	Remote Similarity	NPC247190
0.525	Remote Similarity	NPC187302
0.5217	Remote Similarity	NPC146456
0.5217	Remote Similarity	NPC180079
0.5217	Remote Similarity	NPC83287
0.5213	Remote Similarity	NPC91
0.5204	Remote Similarity	NPC55532
0.5189	Remote Similarity	NPC474423
0.5185	Remote Similarity	NPC480913
0.5155	Remote Similarity	NPC475556
0.5155	Remote Similarity	NPC311706
0.5155	Remote Similarity	NPC486130
0.5122	Remote Similarity	NPC72772
0.5104	Remote Similarity	NPC163365
0.5102	Remote Similarity	NPC475629
0.5102	Remote Similarity	NPC486127
0.5093	Remote Similarity	NPC286809
0.5055	Remote Similarity	NPC203862
0.5055	Remote Similarity	NPC484211
0.5055	Remote Similarity	NPC486129
0.5051	Remote Similarity	NPC470094
0.5051	Remote Similarity	NPC208193

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5822
0.1-0.2	3197
0.2-0.3	114
0.3-0.4	3
0.4-0.5	7
0.5-0.6	4
0.6-0.7	2
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
0.6829	Remote Similarity	NPD7319	Approved
0.6279	Remote Similarity	NPD7507	Pre-clinical
0.5889	Remote Similarity	NPD8294	Phase 4
0.5361	Remote Similarity	NPD8377	Phase 4
0.5217	Remote Similarity	NPD7327	Approved
0.5217	Remote Similarity	NPD7328	Phase 4

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