NPASS Compound

Natural Product: NPC75600

Natural Product ID	NPC75600
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FOVSOBBPLQBYPS-RQSHUPDLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL234334
PubChem CID	10941522
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 92 97 0 0 0 0 0 0 0 0999 V2000 0.7962 -2.6026 -1.4789 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6996 -1.9506 -0.1500 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6592 -2.0008 0.4363 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3940 -0.7030 0.4867 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0435 0.2739 -0.5748 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4355 0.4732 -0.8152 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6270 0.4858 -2.3099 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1722 1.5788 -2.8195 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2212 1.8715 -4.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4492 1.1641 -4.9528 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0221 2.9781 -4.7353 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8719 1.8419 -0.3433 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3423 1.9870 -0.1231 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0476 0.7720 0.3523 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6726 -0.4485 -0.5211 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2584 -0.5542 -0.0824 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2735 -0.2451 1.3026 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4882 0.2456 1.6596 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4268 -0.8154 2.2302 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4131 1.3314 2.7239 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4910 -1.5400 -0.1386 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3520 -2.1548 -1.0343 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3423 -1.6602 -2.2147 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2199 -3.2748 -0.7135 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0533 -3.8301 -1.6537 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8870 -4.9023 -1.3544 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8804 -5.4246 -0.0839 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0558 -4.8822 0.8640 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2207 -3.8035 0.5527 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0866 2.2429 0.7492 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7674 3.3425 0.7345 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8099 3.9891 -0.3424 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5692 3.7362 1.8847 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3908 4.8386 1.7957 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1665 5.2381 2.8836 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1280 4.5402 4.0695 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3067 3.4327 4.1672 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5566 3.0631 3.0843 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7540 -0.1258 -1.7418 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7771 0.6422 -2.2932 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0531 1.7216 -1.7074 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4774 0.1825 -3.5002 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7986 -0.9700 0.3398 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7379 -0.6840 1.2821 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3417 -0.1462 2.3594 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1632 -0.9511 1.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0945 -0.6564 2.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4201 -0.9671 1.8393 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8236 -1.5483 0.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8890 -1.8218 -0.2639 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5817 -1.5322 -0.0338 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 -3.6966 -1.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6404 -2.2199 -2.0554 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1664 -2.6021 -2.0481 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3650 -2.5446 0.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6918 -2.4345 1.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2711 -2.7104 -0.1814 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2787 -0.2373 1.4841 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4718 1.2510 -0.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6549 0.7868 -2.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2977 -0.3935 -2.8398 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3987 3.5718 -3.8549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8663 2.6138 -5.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3339 3.6439 -5.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6235 2.5786 -1.1650 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5342 2.8287 0.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8417 2.2717 -1.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1163 0.9351 0.3681 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8782 -0.2659 -1.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4406 -0.6825 1.8007 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0176 -1.8261 2.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5761 -0.6739 3.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9704 2.2435 2.4272 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3791 1.5335 3.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9320 1.0188 3.6816 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0902 -3.4526 -2.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5482 -5.3477 -2.0846 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5397 -6.2609 0.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0735 -5.3107 1.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5942 -3.4181 1.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4555 5.4117 0.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8114 6.1001 2.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7278 4.8438 4.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2997 2.8998 5.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9191 2.1974 3.1672 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8658 1.0205 -4.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8174 -0.4060 -4.1568 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3015 -0.5111 -3.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7679 -0.2046 3.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1774 -0.7496 2.5765 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8682 -1.7937 0.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8912 -1.7856 -0.8285 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 6 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 6 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 17 18 1 0 18 19 1 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 12 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 5 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 4 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 16 2 1 0 29 24 1 0 38 33 1 0 51 46 1 0 16 6 1 0 18 14 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 1 3 56 1 0 3 57 1 0 4 58 1 1 5 59 1 1 7 60 1 0 7 61 1 0 11 62 1 0 11 63 1 0 11 64 1 0 12 65 1 6 13 66 1 0 13 67 1 0 14 68 1 1 15 69 1 6 19 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 20 75 1 0 25 76 1 0 26 77 1 0 27 78 1 0 28 79 1 0 29 80 1 0 34 81 1 0 35 82 1 0 36 83 1 0 37 84 1 0 38 85 1 0 42 86 1 0 42 87 1 0 42 88 1 0 47 89 1 0 48 90 1 0 49 91 1 0 51 92 1 0 M END

Standard InCHIKey	FOVSOBBPLQBYPS-RQSHUPDLSA-N
Standard InCHI	InChI=1S/C39H41NO11/c1-23-19-30(48-36(45)28-17-12-18-40-21-28)33(47-25(3)42)38(22-46-24(2)41)31(49-34(43)26-13-8-6-9-14-26)20-29-32(39(23,38)51-37(29,4)5)50-35(44)27-15-10-7-11-16-27/h6-18,21,23,29-33H,19-20,22H2,1-5H3/t23-,29-,30+,31+,32-,33+,38-,39-/m1/s1
SMILES	C[C@@H]1C[C@@H]([C@@H]([C@@]2(COC(=O)C)[C@H](C[C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1cccnc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	699.27	Volume:	702.54 ? Van der Waals volume.
Dense:	0.995	LogP:	3.553 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.176 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.07 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	37.0
TPSA:	153.62 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.215	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.891	Fsp³:	0.436
MCE-18:	180.107 ? 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:	0.628	Fluc inhibitor:	0.035 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.45 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.022	Promiscuous compounds:	0.005

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.354	MDCK Permeability:	-4.918
Pgp-inhibitor:	0.956	Pgp-substrate:	0.004
PAMPA:	0.24 ? 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%):	0.0	30% Bioavailability (F30%):	0.006
50% Bioavailability (F50%):	0.548

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.734	MRP1:	1.0
Plasma Protein Binding (PPB):	95.0%	Volume Distribution (VD):	-0.329
Fu:	4.794% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.905	BCRP inhibitor:	0.002
BSEP inhibitor:	0.937

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.59
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.47
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.214	CYP3A4-substrate:	0.931
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.616

Half-life (T1/2):

1.135

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.649
Human Hepatotoxicity (H-HT):	0.029	Drug-induced Liver Injury (DILI):	0.961
AMES Toxicity:	0.707	Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.249	Skin Sensitization:	0.998
Carcinogencity:	0.896	Eye Corrosion:	0.0
Eye Irritation:	0.147	Respiratory Toxicity:	0.037
Drug-induced Neurotoxicity:	0.919	Ototoxicity:	0.218
Hematotoxicity:	0.044	Drug-induced Nephrotoxicity:	0.664
Genotoxicity:	0.187	RPMI-8226 Immunitoxicity:	0.092
A549 Cytotoxicity:	0.564	Hek293 Cytotoxicity:	0.713
BCF:	0.88 ? 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:	4.041 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.107 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.955 ? 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
NPO10749	Capnella thyrsoidea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11536	Xanthocephalum benthamianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8518	Colchicum luteum	Species	Colchicaceae	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	2
Imax	1

Activity Type	# Activity
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	710.0	nM	PMID[17850057]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	707.95	nM	PMID[17850057]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Imax	=	85.8	%	PMID[17850057]

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 NPC75600 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	16288
0.1-0.2	31664
0.2-0.3	1420
0.3-0.4	300
0.4-0.5	101
0.5-0.6	57
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC483884
0.8169	Intermediate Similarity	NPC191082
0.7671	Intermediate Similarity	NPC4341
0.759	Intermediate Similarity	NPC483885
0.7333	Intermediate Similarity	NPC67777
0.72	Intermediate Similarity	NPC479047
0.72	Intermediate Similarity	NPC291638
0.6962	Remote Similarity	NPC184747
0.6883	Remote Similarity	NPC139067
0.6883	Remote Similarity	NPC177340
0.6782	Remote Similarity	NPC176413
0.6709	Remote Similarity	NPC479044
0.6591	Remote Similarity	NPC294512
0.6456	Remote Similarity	NPC43241
0.6316	Remote Similarity	NPC270498
0.631	Remote Similarity	NPC483887
0.631	Remote Similarity	NPC158020
0.6222	Remote Similarity	NPC479045
0.6047	Remote Similarity	NPC608007
0.5952	Remote Similarity	NPC70716
0.5952	Remote Similarity	NPC95265
0.5897	Remote Similarity	NPC473081
0.5897	Remote Similarity	NPC200592
0.5897	Remote Similarity	NPC610542
0.5862	Remote Similarity	NPC88593
0.5843	Remote Similarity	NPC473089
0.5806	Remote Similarity	NPC483868
0.5802	Remote Similarity	NPC17877
0.5778	Remote Similarity	NPC127026
0.5778	Remote Similarity	NPC483890
0.5765	Remote Similarity	NPC97667
0.5682	Remote Similarity	NPC6815
0.5682	Remote Similarity	NPC14499
0.5667	Remote Similarity	NPC56953
0.5663	Remote Similarity	NPC137718
0.561	Remote Similarity	NPC51314
0.5604	Remote Similarity	NPC473115
0.5581	Remote Similarity	NPC127720
0.5542	Remote Similarity	NPC246480
0.5542	Remote Similarity	NPC147880
0.5529	Remote Similarity	NPC41481
0.5506	Remote Similarity	NPC212768
0.55	Remote Similarity	NPC195647
0.5476	Remote Similarity	NPC27377
0.5465	Remote Similarity	NPC479043
0.5455	Remote Similarity	NPC479042
0.5444	Remote Similarity	NPC488900
0.5444	Remote Similarity	NPC488899
0.5412	Remote Similarity	NPC471100
0.5412	Remote Similarity	NPC605884
0.5385	Remote Similarity	NPC610927
0.5368	Remote Similarity	NPC479046
0.5349	Remote Similarity	NPC472574
0.5349	Remote Similarity	NPC92293
0.5333	Remote Similarity	NPC479049
0.5333	Remote Similarity	NPC4421
0.5326	Remote Similarity	NPC479041
0.5294	Remote Similarity	NPC148062
0.5287	Remote Similarity	NPC266265
0.5238	Remote Similarity	NPC473060
0.5233	Remote Similarity	NPC171207
0.5233	Remote Similarity	NPC473673
0.5204	Remote Similarity	NPC488902
0.5204	Remote Similarity	NPC488903
0.5176	Remote Similarity	NPC48017
0.5169	Remote Similarity	NPC473613
0.5161	Remote Similarity	NPC6576
0.5161	Remote Similarity	NPC610134
0.5111	Remote Similarity	NPC609309
0.5059	Remote Similarity	NPC483902
0.5059	Remote Similarity	NPC472577
0.5057	Remote Similarity	NPC254558
0.5057	Remote Similarity	NPC471107
0.5056	Remote Similarity	NPC96903
0.5054	Remote Similarity	NPC479048
0.5054	Remote Similarity	NPC611111

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC75600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2803
0.1-0.2	6208
0.2-0.3	136
0.3-0.4	3
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