NPASS Compound

Natural Product: NPC485735

Natural Product ID	NPC485735
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XREDRJVZJRMVHB-GRYPTCQRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	3044018
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 88 91 0 0 0 0 0 0 0 0999 V2000 10.8345 -0.8912 0.4926 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4158 -1.3547 0.6515 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4289 -0.3325 0.1182 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0112 -0.8163 0.2868 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0495 0.2381 -0.2614 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6374 -0.2267 -0.1010 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6345 0.8125 -0.6364 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8908 1.0527 -2.0666 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7926 -0.0975 -2.9553 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6157 -0.8321 -3.3630 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6192 -1.4442 -2.4788 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7487 -0.4495 -1.8217 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 0.7461 -2.1966 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1488 -0.7574 -0.8232 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0002 0.1873 -0.1805 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9535 0.9079 -1.0825 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2316 0.0990 -1.3501 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8012 -1.0612 -2.2550 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7969 -0.4779 -0.0968 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1187 0.2090 1.0637 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8069 -0.0737 2.3568 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0402 0.3257 2.6611 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0220 1.1153 1.8554 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7972 0.9793 0.3803 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2802 -0.3879 0.0292 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0143 -0.8587 -1.1368 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0612 -0.0838 -1.3219 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1055 -0.1892 -2.4041 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1219 0.9683 -0.3050 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0924 1.7205 -0.0497 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0701 2.0111 -0.1773 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5607 -0.0569 4.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8542 1.1300 4.6977 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6901 -0.2570 1.0979 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5626 0.6988 1.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7697 2.1340 1.5507 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6918 0.0999 1.7503 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4644 -1.8490 0.0149 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8378 0.2128 0.6394 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4511 -1.3458 1.3162 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3006 -1.1755 -0.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1580 -1.5727 1.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2706 -2.3294 0.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6288 -0.0873 -0.9368 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5971 0.6043 0.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8820 -1.7053 -0.3799 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8250 -1.0540 1.3330 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2360 1.1703 0.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3239 0.3475 -1.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3859 -0.3569 0.9920 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4824 -1.1555 -0.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8193 1.7850 -0.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6677 0.4850 -0.3057 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9314 1.5531 -2.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2529 1.9372 -2.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5680 -0.9138 -2.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3538 0.2506 -3.9458 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0657 -0.1196 -4.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9514 -1.6235 -4.1662 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9811 -2.1453 -3.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0668 -2.1487 -1.7238 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1777 1.9412 -0.8101 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4716 0.9664 -2.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9086 0.7360 -1.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9942 -0.7063 -2.9529 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6228 -1.4172 -2.8851 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4535 -1.8923 -1.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1187 1.2812 0.8702 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3032 -0.6329 3.1129 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0582 2.1744 2.1681 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0450 0.6967 2.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5713 -1.0576 0.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7609 -1.6958 -1.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6815 -0.8679 -3.1694 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3547 0.8114 -2.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0384 -0.6372 -2.0324 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5867 2.5505 -0.8426 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7495 -0.5481 4.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4607 -0.6920 3.9551 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1680 1.8255 4.5241 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5575 -1.3167 1.3545 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3757 2.7327 0.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1822 2.6615 1.7267 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2783 2.0968 2.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4110 -0.1307 2.8202 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5225 0.8058 1.8080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9507 -0.8787 1.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2041 -2.3568 0.4590 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 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 15 14 1 6 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 27 29 1 0 29 30 2 0 24 31 1 6 22 32 1 0 32 33 1 0 20 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 19 38 1 6 34 15 1 0 35 15 1 0 25 19 1 0 29 24 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 2 43 1 0 3 44 1 0 3 45 1 0 4 46 1 0 4 47 1 0 5 48 1 0 5 49 1 0 6 50 1 0 6 51 1 0 7 52 1 0 7 53 1 0 8 54 1 0 8 55 1 0 9 56 1 0 9 57 1 0 10 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 16 62 1 0 16 63 1 0 17 64 1 6 18 65 1 0 18 66 1 0 18 67 1 0 20 68 1 6 21 69 1 0 23 70 1 0 23 71 1 0 25 72 1 1 26 73 1 0 28 74 1 0 28 75 1 0 28 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 33 80 1 0 34 81 1 1 36 82 1 0 36 83 1 0 36 84 1 0 37 85 1 0 37 86 1 0 37 87 1 0 38 88 1 0 M END

Standard InCHIKey	XREDRJVZJRMVHB-GRYPTCQRSA-N
Standard InCHI	InChI=1S/C32H50O6/c1-6-7-8-9-10-11-12-13-14-15-26(34)38-31-18-22(3)32(37)24(27(31)29(31,4)5)17-23(20-33)19-30(36)25(32)16-21(2)28(30)35/h16-17,22,24-25,27,33,36-37H,6-15,18-20H2,1-5H3/t22-,24+,25-,27-,30-,31+,32-/m1/s1
SMILES	CCCCCCCCCCCC(=O)O[C@@]12C[C@@H](C)[C@]3([C@@H](C=C(C[C@]4([C@H]3C=C(C)C4=O)O)CO)[C@@H]1C2(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	530.36	Volume:	569.998 ? Van der Waals volume.
Dense:	0.93	LogP:	5.149 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.28 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.794 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	20.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.177	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.817	Fsp³:	0.812
MCE-18:	75.034 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.351	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.231	Promiscuous compounds:	0.662

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.033	MDCK Permeability:	-4.688
Pgp-inhibitor:	0.001	Pgp-substrate:	0.732
PAMPA:	0.3 ? 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):	0.107
20% Bioavailability (F20%):	0.955	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.995
Plasma Protein Binding (PPB):	95.556%	Volume Distribution (VD):	0.635
Fu:	5.599% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.88
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.078
BSEP inhibitor:	0.977

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.057	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.485
CYP3A4-inhibitor:	0.292	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.04 ? 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):

4.741

Half-life (T1/2):

0.89

ADMET: Toxicity

hERG Blockers:	0.267	hERG Blockers (10um):	0.532
Human Hepatotoxicity (H-HT):	0.634	Drug-induced Liver Injury (DILI):	0.234
AMES Toxicity:	0.127	Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.335	Skin Sensitization:	0.967
Carcinogencity:	0.462	Eye Corrosion:	0.11
Eye Irritation:	0.773	Respiratory Toxicity:	0.883
Drug-induced Neurotoxicity:	0.059	Ototoxicity:	0.479
Hematotoxicity:	0.493	Drug-induced Nephrotoxicity:	0.4
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.479	Hek293 Cytotoxicity:	0.214
BCF:	2.129 ? 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:	5.332 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.688 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.126 ? 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
NPO40934	Stillingia loranthacea	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31599155]

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
CC50	1

Activity Type	# Activity
Cell line	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
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	=	24600.0	nM	PMID[31599155]

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 NPC485735 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	15530
0.1-0.2	32588
0.2-0.3	1568
0.3-0.4	70
0.4-0.5	31
0.5-0.6	31
0.6-0.7	15
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC485736
1.0	High Similarity	NPC277477
1.0	High Similarity	NPC479003
0.8889	High Similarity	NPC485732
0.8136	Intermediate Similarity	NPC153036
0.8095	Intermediate Similarity	NPC485733
0.7869	Intermediate Similarity	NPC158523
0.7846	Intermediate Similarity	NPC482454
0.7727	Intermediate Similarity	NPC17138
0.7727	Intermediate Similarity	NPC101825
0.7727	Intermediate Similarity	NPC215643
0.7727	Intermediate Similarity	NPC265499
0.7619	Intermediate Similarity	NPC71889
0.7619	Intermediate Similarity	NPC475937
0.7612	Intermediate Similarity	NPC221511
0.7286	Intermediate Similarity	NPC151216
0.7286	Intermediate Similarity	NPC89227
0.7246	Intermediate Similarity	NPC485731
0.7206	Intermediate Similarity	NPC170212
0.7123	Intermediate Similarity	NPC472760
0.7	Intermediate Similarity	NPC477091
0.6957	Remote Similarity	NPC275696
0.6957	Remote Similarity	NPC255081
0.6712	Remote Similarity	NPC479000
0.6667	Remote Similarity	NPC153651
0.662	Remote Similarity	NPC5991
0.662	Remote Similarity	NPC196500
0.662	Remote Similarity	NPC471108
0.662	Remote Similarity	NPC5989
0.6575	Remote Similarity	NPC22628
0.6575	Remote Similarity	NPC600005
0.6462	Remote Similarity	NPC91189
0.6269	Remote Similarity	NPC96739
0.6197	Remote Similarity	NPC609113
0.6143	Remote Similarity	NPC171905
0.6	Remote Similarity	NPC174471
0.5974	Remote Similarity	NPC609983
0.5946	Remote Similarity	NPC474872
0.5926	Remote Similarity	NPC180640
0.5867	Remote Similarity	NPC603912
0.5854	Remote Similarity	NPC185876
0.5854	Remote Similarity	NPC19336
0.5833	Remote Similarity	NPC474871
0.5833	Remote Similarity	NPC260786
0.5802	Remote Similarity	NPC138641
0.5802	Remote Similarity	NPC611243
0.5652	Remote Similarity	NPC156252
0.5641	Remote Similarity	NPC484333
0.5513	Remote Similarity	NPC183540
0.5479	Remote Similarity	NPC472397
0.5432	Remote Similarity	NPC159692
0.5333	Remote Similarity	NPC157252
0.5333	Remote Similarity	NPC472758
0.5309	Remote Similarity	NPC222307
0.5301	Remote Similarity	NPC469647
0.5301	Remote Similarity	NPC469648
0.527	Remote Similarity	NPC478681
0.5263	Remote Similarity	NPC471125
0.5195	Remote Similarity	NPC145182
0.5122	Remote Similarity	NPC602538
0.5119	Remote Similarity	NPC482199
0.5119	Remote Similarity	NPC482197
0.5116	Remote Similarity	NPC479001
0.5116	Remote Similarity	NPC479002
0.5114	Remote Similarity	NPC283875
0.5063	Remote Similarity	NPC471128
0.5063	Remote Similarity	NPC471126

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC485735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6346
0.1-0.2	2759
0.2-0.3	45
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