NPASS Compound

Natural Product: NPC97667

Natural Product ID	NPC97667
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SUKGHCPJNGDNSA-LLKZBMCISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL191573
PubChem CID	636819
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 80 83 0 0 0 0 0 0 0 0999 V2000 -1.3795 0.7440 5.3432 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5094 0.1864 4.2476 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7225 0.1570 4.3415 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1039 -0.2833 3.1546 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8774 -0.8272 1.9682 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2919 -0.1596 0.7796 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0910 0.3214 1.0994 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2207 1.7879 1.4003 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2818 2.7040 0.7260 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1288 2.1882 1.0614 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1089 0.9623 0.1995 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4704 0.5757 -0.2651 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4794 0.2191 0.7739 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3412 -0.4253 -1.3631 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0148 -1.0748 -1.4931 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2181 -1.2694 -0.2671 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5800 -2.5446 0.2939 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2385 -3.6260 0.3850 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4137 -3.5381 -0.0485 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1964 -4.9173 0.9785 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1355 -2.3738 -2.1072 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5875 -2.7145 -3.3074 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0650 -1.8248 -3.9086 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7356 -4.0659 -3.9059 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0129 1.7453 -0.8732 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4502 1.3882 -0.9555 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2020 2.5714 -0.7601 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5109 3.7954 -1.3051 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5776 2.5625 -1.4414 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1381 3.0668 0.6491 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0942 3.5841 1.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0754 3.2609 2.6979 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1170 4.5063 0.9468 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9808 -0.0201 -0.0002 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0937 -0.7978 0.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3303 -1.2097 1.4021 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0307 -1.1847 -0.8301 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1230 -1.9590 -0.4995 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0482 -2.3646 -1.4376 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8251 -1.9525 -2.7409 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7373 -1.1776 -3.0889 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8273 -0.7851 -2.1355 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7918 1.4444 5.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8491 -0.0539 5.9310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2135 1.3558 4.9057 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6638 -1.6009 1.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0359 -1.6229 2.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5662 -0.2033 1.9490 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1263 1.9591 2.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3035 2.0297 1.1860 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4365 3.7156 1.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2497 2.0089 2.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7155 -0.8859 0.7104 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5075 0.6522 0.5433 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2863 0.5800 1.7816 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5954 -0.0009 -2.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1809 -1.1680 -1.1982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4031 -0.5173 -2.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8378 -1.3981 -0.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1859 -5.7899 0.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3057 -4.9874 1.0654 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2998 -4.9983 1.9750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -4.3975 -3.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0776 -4.7507 -3.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4984 -4.0797 -4.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8236 1.4147 -1.3650 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1804 4.4301 -1.9480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7614 4.5326 -0.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3427 3.5813 -1.9734 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4115 2.5827 -0.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6183 1.7535 -2.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7285 3.4968 -2.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0094 4.4287 1.6206 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6754 5.5290 0.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3919 4.2264 -0.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2799 -2.2716 0.5284 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8950 -2.9643 -1.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4981 -2.2207 -3.5542 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5596 -0.8530 -4.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9784 -0.1884 -2.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 1 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 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 12 25 1 6 11 26 1 6 26 27 1 0 27 28 1 0 27 29 1 0 10 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 7 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 16 6 1 0 42 37 1 0 11 6 1 0 27 9 1 0 1 43 1 0 1 44 1 0 1 45 1 0 5 46 1 0 5 47 1 0 7 48 1 1 8 49 1 0 8 50 1 0 9 51 1 6 10 52 1 1 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 6 16 59 1 6 20 60 1 0 20 61 1 0 20 62 1 0 24 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 28 67 1 0 28 68 1 0 28 69 1 0 29 70 1 0 29 71 1 0 29 72 1 0 33 73 1 0 33 74 1 0 33 75 1 0 38 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 M END

Standard InCHIKey	SUKGHCPJNGDNSA-LLKZBMCISA-N
Standard InCHI	InChI=1S/C30H38O12/c1-16(31)37-15-29-23(41-26(35)20-11-9-8-10-12-20)13-21-24(39-18(3)33)30(29,42-27(21,5)6)28(7,36)14-22(38-17(2)32)25(29)40-19(4)34/h8-12,21-25,36H,13-15H2,1-7H3/t21-,22+,23+,24-,25+,28+,29-,30+/m1/s1
SMILES	CC(=O)OC[C@@]12[C@H](C[C@@H]3[C@H]([C@@]2([C@](C)(C[C@@H]([C@@H]1OC(=O)C)OC(=O)C)O)OC3(C)C)OC(=O)C)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	590.24	Volume:	577.601 ? Van der Waals volume.
Dense:	1.022	LogP:	2.495 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.708 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.052 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	25.0
TPSA:	160.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.365	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.88	Fsp³:	0.633
MCE-18:	155.714 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.173	Fluc inhibitor:	0.036 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.034 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.099	Promiscuous compounds:	0.299

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.068	MDCK Permeability:	-4.683
Pgp-inhibitor:	0.997	Pgp-substrate:	0.488
PAMPA:	0.279 ? 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%):	0.109	30% Bioavailability (F30%):	0.5
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209	MRP1:	1.0
Plasma Protein Binding (PPB):	58.821%	Volume Distribution (VD):	-0.376
Fu:	36.104% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.957	BCRP inhibitor:	0.004
BSEP inhibitor:	0.988

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.872 ? 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):

1.841

Half-life (T1/2):

1.309

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.18
Human Hepatotoxicity (H-HT):	0.076	Drug-induced Liver Injury (DILI):	0.601
AMES Toxicity:	0.914	Rat Oral Acute Toxicity:	0.416
Maximum Recommended Daily Dose:	0.263	Skin Sensitization:	0.998
Carcinogencity:	0.885	Eye Corrosion:	0.01
Eye Irritation:	0.586	Respiratory Toxicity:	0.036
Drug-induced Neurotoxicity:	0.367	Ototoxicity:	0.18
Hematotoxicity:	0.12	Drug-induced Nephrotoxicity:	0.575
Genotoxicity:	0.717	RPMI-8226 Immunitoxicity:	0.068
A549 Cytotoxicity:	0.168	Hek293 Cytotoxicity:	0.427
BCF:	0.539 ? 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:	3.537 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.146 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.591 ? 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
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974580]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26437	Maytenus jelskii	Species	Celastraceae	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

Activity Type	# Activity
Ki	1
Activity	5

Activity Type	# Activity
Cell line	2
Others	4

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
NPT886	Cell line	NIH3T3	Mus musculus	Ki	=	4392.0	nM	DrugMatrix in vitro pharmacology data
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[18955522]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[2292689]
NPT2	Others	Unspecified	n.a.	Activity	=	31.1	%	PMID[18578517]
NPT2	Others	Unspecified	n.a.	Activity	=	75.4	%	PMID[14695811]
NPT2	Others	Unspecified	n.a.	Activity	=	95.1	%	PMID[23992864]

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 NPC97667 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	12920
0.1-0.2	34312
0.2-0.3	1963
0.3-0.4	476
0.4-0.5	100
0.5-0.6	42
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9385	High Similarity	NPC70716
0.9385	High Similarity	NPC95265
0.9104	High Similarity	NPC479042
0.7973	Intermediate Similarity	NPC610134
0.7922	Intermediate Similarity	NPC294512
0.7595	Intermediate Similarity	NPC483868
0.7571	Intermediate Similarity	NPC171207
0.7468	Intermediate Similarity	NPC176413
0.7468	Intermediate Similarity	NPC483885
0.7468	Intermediate Similarity	NPC479045
0.7361	Intermediate Similarity	NPC11685
0.7361	Intermediate Similarity	NPC16912
0.7123	Intermediate Similarity	NPC472570
0.7067	Intermediate Similarity	NPC481489
0.7042	Intermediate Similarity	NPC479047
0.7042	Intermediate Similarity	NPC291638
0.6892	Remote Similarity	NPC472569
0.6883	Remote Similarity	NPC6815
0.6806	Remote Similarity	NPC4341
0.68	Remote Similarity	NPC96903
0.6757	Remote Similarity	NPC479044
0.6753	Remote Similarity	NPC481488
0.6711	Remote Similarity	NPC282239
0.6711	Remote Similarity	NPC472568
0.6625	Remote Similarity	NPC479041
0.6575	Remote Similarity	NPC191082
0.65	Remote Similarity	NPC479048
0.6486	Remote Similarity	NPC43241
0.6456	Remote Similarity	NPC479049
0.6447	Remote Similarity	NPC57628
0.6282	Remote Similarity	NPC471102
0.6267	Remote Similarity	NPC139067
0.6267	Remote Similarity	NPC177340
0.6154	Remote Similarity	NPC184747
0.6104	Remote Similarity	NPC41481
0.6076	Remote Similarity	NPC481490
0.6053	Remote Similarity	NPC67777
0.6053	Remote Similarity	NPC158663
0.6	Remote Similarity	NPC17877
0.6	Remote Similarity	NPC281717
0.5926	Remote Similarity	NPC481487
0.5833	Remote Similarity	NPC56953
0.5769	Remote Similarity	NPC471104
0.5765	Remote Similarity	NPC75600
0.5765	Remote Similarity	NPC483884
0.575	Remote Similarity	NPC106895
0.5676	Remote Similarity	NPC195647
0.5658	Remote Similarity	NPC483879
0.5641	Remote Similarity	NPC270590
0.5641	Remote Similarity	NPC27377
0.561	Remote Similarity	NPC609309
0.5584	Remote Similarity	NPC483902
0.5584	Remote Similarity	NPC472577
0.5584	Remote Similarity	NPC483886
0.5581	Remote Similarity	NPC483870
0.5542	Remote Similarity	NPC481486
0.5513	Remote Similarity	NPC48017
0.5513	Remote Similarity	NPC147880
0.5476	Remote Similarity	NPC488917
0.5467	Remote Similarity	NPC473081
0.5467	Remote Similarity	NPC200592
0.5467	Remote Similarity	NPC610542
0.5455	Remote Similarity	NPC483869
0.5443	Remote Similarity	NPC471101
0.5432	Remote Similarity	NPC266265
0.5375	Remote Similarity	NPC473673
0.5375	Remote Similarity	NPC471100
0.5375	Remote Similarity	NPC605884
0.5316	Remote Similarity	NPC246480
0.5301	Remote Similarity	NPC476970
0.5263	Remote Similarity	NPC270498
0.525	Remote Similarity	NPC148062
0.5244	Remote Similarity	NPC479043
0.5227	Remote Similarity	NPC127026
0.5227	Remote Similarity	NPC483890
0.519	Remote Similarity	NPC473060
0.5125	Remote Similarity	NPC483883
0.5125	Remote Similarity	NPC151585
0.5122	Remote Similarity	NPC92293
0.5114	Remote Similarity	NPC184817
0.5062	Remote Similarity	NPC147217
0.5062	Remote Similarity	NPC137718

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC97667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3362
0.1-0.2	5586
0.2-0.3	201
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