NPASS Compound

Natural Product: NPC146170

Natural Product ID	NPC146170
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MXJMQPDZBSPQBW-HIQRJBJLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21604187
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 0 0 0 0 0 0 0 0999 V2000 4.0617 0.6348 2.5275 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6543 -0.2722 1.8072 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7863 -1.0434 2.3828 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2554 -0.5714 0.4259 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4449 -0.1251 -0.4117 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5575 -0.5601 -0.2661 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9577 0.8990 -1.3839 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5519 0.3475 -1.5787 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6322 1.2332 -2.2892 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3811 1.6575 -1.6057 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8415 0.8326 -0.5055 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6074 1.7420 0.6847 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7758 -0.3300 -0.1266 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3483 -1.0437 1.1103 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0660 -1.5530 0.9168 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9752 -0.4759 0.4149 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4356 -0.8384 0.4463 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7614 -2.0547 -0.3570 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9447 -1.0839 1.8421 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4694 0.1718 2.5072 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7724 0.5711 1.8553 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5998 0.4878 0.3449 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4850 -0.5363 -0.2804 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0838 1.8507 -0.1895 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1640 0.4115 -0.0055 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8715 0.7002 -1.4253 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3975 1.1079 -1.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4792 0.1173 -0.8542 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2109 -0.9262 -1.9316 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8334 -0.2249 2.2831 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1367 0.2211 -0.1218 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7172 -0.9591 -2.2376 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4163 -2.0781 -1.8183 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3008 -0.9544 -3.5340 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4336 0.7991 3.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2282 1.2677 2.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7319 -1.0117 3.4838 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7414 -0.5328 2.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8496 -2.0656 1.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1278 -1.6715 0.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4924 0.8592 -2.3414 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9623 1.8664 -0.8809 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4208 0.7804 -3.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2494 2.1374 -2.6028 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5742 2.7263 -1.2646 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6367 1.8443 -2.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3995 2.2354 0.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3170 2.6244 0.6011 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 1.3074 1.6514 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6534 -1.0758 -0.9360 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 -0.5527 2.0618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9907 -1.9768 1.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0544 -2.4861 0.3631 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3637 -1.8576 1.9665 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9054 0.3469 1.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9154 -1.9254 -1.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7058 -2.5219 0.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9812 -2.8152 -0.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2703 -1.5609 2.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8451 -1.7689 1.7819 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7349 -0.1361 3.5551 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7410 0.9725 2.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9961 1.5998 2.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7745 -1.3670 0.4187 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4839 -0.0823 -0.5605 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0765 -0.9093 -1.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9779 2.1413 0.3856 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3103 2.6165 -0.1047 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4341 1.7126 -1.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6683 1.2480 0.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1456 -0.0455 -2.1578 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4319 1.6368 -1.7029 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2382 1.1351 -2.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2998 2.1394 -1.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0901 -0.9880 -2.6477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6164 -0.5974 -2.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0810 -1.9383 -1.5709 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5351 -1.0654 2.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1788 1.2737 0.2954 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0469 -1.6737 -4.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 13 31 1 0 8 32 1 6 32 33 2 0 32 34 1 0 31 4 1 0 31 8 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 1 7 41 1 0 7 42 1 0 9 43 1 0 9 44 1 0 10 45 1 0 10 46 1 0 12 47 1 0 12 48 1 0 12 49 1 0 13 50 1 6 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 1 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 6 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 24 69 1 0 25 70 1 1 26 71 1 0 26 72 1 0 27 73 1 0 27 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 31 79 1 1 34 80 1 0 M END

Standard InCHIKey	MXJMQPDZBSPQBW-HIQRJBJLSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-17(2)23-19(31)16-30(25(33)34)15-14-28(6)18(24(23)30)8-9-21-27(5)12-11-22(32)26(3,4)20(27)10-13-29(21,28)7/h18,20-24,32H,1,8-16H2,2-7H3,(H,33,34)/t18-,20+,21-,22+,23-,24+,27+,28-,29-,30-/m1/s1
SMILES	C=C(C)[C@@H]1C(=O)C[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.335 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.918 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.336 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.467	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.894	Fsp³:	0.867
MCE-18:	105.857 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.865	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.289	Promiscuous compounds:	0.269

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.419	MDCK Permeability:	-5.037
Pgp-inhibitor:	0.0	Pgp-substrate:	0.007
PAMPA:	0.992 ? 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%):	0.062	30% Bioavailability (F30%):	0.1
50% Bioavailability (F50%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192	MRP1:	0.979
Plasma Protein Binding (PPB):	97.322%	Volume Distribution (VD):	-0.417
Fu:	2.75% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.098
BSEP inhibitor:	0.304

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.94	CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.053	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.042
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.315
HLM stability:	0.024 ? 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):

4.806

Half-life (T1/2):

1.077

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.055
Human Hepatotoxicity (H-HT):	0.71	Drug-induced Liver Injury (DILI):	0.777
AMES Toxicity:	0.307	Rat Oral Acute Toxicity:	0.352
Maximum Recommended Daily Dose:	0.4	Skin Sensitization:	0.977
Carcinogencity:	0.921	Eye Corrosion:	0.225
Eye Irritation:	0.846	Respiratory Toxicity:	0.899
Drug-induced Neurotoxicity:	0.079	Ototoxicity:	0.585
Hematotoxicity:	0.523	Drug-induced Nephrotoxicity:	0.803
Genotoxicity:	0.848	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.147	Hek293 Cytotoxicity:	0.158
BCF:	0.674 ? 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:	3.551 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.158 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.566 ? 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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23254	Monoclea forsteri	Species	Monocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23254	Monoclea forsteri	Species	Monocleaceae	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

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

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 NPC146170 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	17479
0.1-0.2	27051
0.2-0.3	4374
0.3-0.4	728
0.4-0.5	183
0.5-0.6	28
0.6-0.7	7
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7419	Intermediate Similarity	NPC264317
0.7419	Intermediate Similarity	NPC294438
0.7143	Intermediate Similarity	NPC30583
0.6818	Remote Similarity	NPC18064
0.6818	Remote Similarity	NPC16377
0.6562	Remote Similarity	NPC472608
0.6515	Remote Similarity	NPC476071
0.6324	Remote Similarity	NPC151191
0.6269	Remote Similarity	NPC488164
0.6269	Remote Similarity	NPC264005
0.5915	Remote Similarity	NPC488165
0.589	Remote Similarity	NPC481311
0.5857	Remote Similarity	NPC2783
0.5714	Remote Similarity	NPC201655
0.5571	Remote Similarity	NPC474686
0.5571	Remote Similarity	NPC488506
0.5571	Remote Similarity	NPC220498
0.541	Remote Similarity	NPC232112
0.5352	Remote Similarity	NPC181225
0.5352	Remote Similarity	NPC213832
0.5286	Remote Similarity	NPC192744
0.5278	Remote Similarity	NPC474512
0.5231	Remote Similarity	NPC192638
0.5231	Remote Similarity	NPC25511
0.5231	Remote Similarity	NPC600137
0.5217	Remote Similarity	NPC298168
0.5217	Remote Similarity	NPC143133
0.5152	Remote Similarity	NPC97534
0.5152	Remote Similarity	NPC195155
0.5139	Remote Similarity	NPC24772
0.5139	Remote Similarity	NPC30322
0.5135	Remote Similarity	NPC475061
0.5135	Remote Similarity	NPC601275
0.5072	Remote Similarity	NPC74595
0.5072	Remote Similarity	NPC264665
0.5072	Remote Similarity	NPC68828
0.5072	Remote Similarity	NPC269396
0.5067	Remote Similarity	NPC486704

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC146170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5174
0.1-0.2	3834
0.2-0.3	132
0.3-0.4	6
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7419	Intermediate Similarity	NPD7520	Phase 1

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