NPASS Compound

Natural Product: NPC37221

Natural Product ID	NPC37221
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XKYZQPLLLQGSRQ-APCIVXMWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	91440115
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 82 86 0 0 0 0 0 0 0 0999 V2000 -4.5359 1.3626 2.5477 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0369 2.1899 1.3775 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0530 3.2911 1.1585 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9502 1.3876 0.0933 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3358 0.8443 -0.2751 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1681 -0.6793 -0.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7194 -0.7243 -0.8527 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1239 -2.0929 -0.7798 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6421 -1.9423 -1.1539 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9295 -0.9792 -0.2137 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8862 -1.6873 1.1291 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6646 0.3113 -0.1299 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0983 1.4895 -0.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3620 1.6491 -0.5833 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0704 0.3900 -0.0229 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5303 0.5131 0.0527 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1562 1.4985 -0.8871 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8878 1.0634 1.4537 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3567 1.2018 1.6306 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2048 0.0739 1.2079 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6755 -0.8315 0.1435 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0474 -2.2618 0.5920 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3577 -0.6387 -1.1935 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1810 -0.8438 0.0577 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6620 -1.7280 -1.0201 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2191 -2.0476 -0.5975 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4506 -0.7374 -0.7535 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3458 -0.5280 -2.2410 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4172 0.6123 0.7095 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5490 1.4507 3.0165 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1157 0.1843 0.1884 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6966 -0.2086 -2.2219 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1001 0.8181 -2.6130 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4028 -0.9158 -3.2028 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5795 2.0982 3.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5789 1.0222 2.4361 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8313 0.5773 2.8631 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0589 2.5911 1.6974 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6470 3.4880 2.0812 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7017 3.0095 0.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5153 4.2337 0.8707 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6381 2.0276 -0.7375 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6548 1.1795 -1.2767 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0926 1.0213 0.4834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2588 -1.1794 0.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8028 -1.1217 -1.1521 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5688 -2.7004 -1.5897 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2310 -2.5516 0.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1866 -2.9397 -0.9920 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5762 -1.6760 -2.2066 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6855 -2.7770 0.8929 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0457 -1.3895 1.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8577 -1.7090 1.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7107 2.3723 -0.2240 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4836 1.7568 -1.6543 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8064 2.5217 -0.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6550 0.3507 1.0312 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7805 2.5149 -0.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0361 1.3064 -1.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2474 1.5349 -0.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5214 0.2674 2.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4035 2.0215 1.6355 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6676 2.1893 1.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5403 -0.4870 2.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0262 -2.2564 1.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2921 -2.6695 1.2744 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1669 -2.9228 -0.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6474 -0.4614 -2.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9419 -1.5488 -1.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1559 0.1602 -1.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8425 -1.3169 1.0333 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6299 -1.2503 -1.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2637 -2.6601 -1.0154 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8249 -2.7463 -1.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2557 -2.4090 0.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2026 0.0200 -2.6818 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3308 -1.5026 -2.8082 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5472 0.0243 -2.5737 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7697 1.1576 1.4805 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6086 0.5736 3.5035 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2315 -0.3571 1.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1144 -0.8726 -4.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 1 10 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 20 29 1 0 19 30 1 0 12 31 1 0 7 32 1 6 32 33 2 0 32 34 1 0 31 4 1 0 31 7 1 0 27 10 1 0 27 15 1 0 24 16 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 6 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 8 47 1 0 8 48 1 0 9 49 1 0 9 50 1 0 11 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 1 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 6 20 64 1 1 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 23 70 1 0 24 71 1 1 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 30 80 1 0 31 81 1 1 34 82 1 0 M END

Standard InCHIKey	XKYZQPLLLQGSRQ-APCIVXMWSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h8,17-18,20-24,31-32H,9-16H2,1-7H3,(H,33,34)/t18-,20+,21-,22+,23+,24-,27-,28+,29+,30-/m0/s1
SMILES	CC(C)[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.791 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.346 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.536 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.427	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.913	Fsp³:	0.9
MCE-18:	104.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.785	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.039 ? 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:	0.308	Promiscuous compounds:	0.092

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.429	MDCK Permeability:	-5.051
Pgp-inhibitor:	0.004	Pgp-substrate:	0.022
PAMPA:	0.999 ? 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):	0.001
20% Bioavailability (F20%):	0.297	30% Bioavailability (F30%):	0.115
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122	MRP1:	0.974
Plasma Protein Binding (PPB):	96.162%	Volume Distribution (VD):	-0.16
Fu:	3.795% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.937	BCRP inhibitor:	0.007
BSEP inhibitor:	0.807

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.04
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.003 ? 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):

3.989

Half-life (T1/2):

1.006

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.056
Human Hepatotoxicity (H-HT):	0.618	Drug-induced Liver Injury (DILI):	0.678
AMES Toxicity:	0.257	Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.233	Skin Sensitization:	0.645
Carcinogencity:	0.799	Eye Corrosion:	0.012
Eye Irritation:	0.486	Respiratory Toxicity:	0.707
Drug-induced Neurotoxicity:	0.019	Ototoxicity:	0.762
Hematotoxicity:	0.443	Drug-induced Nephrotoxicity:	0.869
Genotoxicity:	0.271	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.053	Hek293 Cytotoxicity:	0.071
BCF:	1.41 ? 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:	3.788 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.258 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.596 ? 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
NPO3447	Beaumontia murtonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28598616]
NPO40841	Eugenia operculata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28598616]
NPO26636	Hakea amplexicaulis	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9846	Argyranthemum frutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8128	Malacosoma americanum	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13980	Euphorbia polygonifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21940	Achillea arabica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25757	Meliosma lanceolata	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26688	Pterogorgia bipinnata	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26120	Catharsius molossus	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9846	Argyranthemum frutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26636	Hakea amplexicaulis	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3447	Beaumontia murtonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26484	Reniera cratera	n.a.	n.a.	n.a.	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
IC50	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	23000.0	nM	PMID[28598616]

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 NPC37221 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	24943
0.1-0.2	21233
0.2-0.3	2941
0.3-0.4	458
0.4-0.5	165
0.5-0.6	74
0.6-0.7	25
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8387	Intermediate Similarity	NPC71074
0.8387	Intermediate Similarity	NPC605937
0.7727	Intermediate Similarity	NPC25299
0.7727	Intermediate Similarity	NPC481322
0.7424	Intermediate Similarity	NPC259733
0.7424	Intermediate Similarity	NPC158371
0.7424	Intermediate Similarity	NPC207922
0.7424	Intermediate Similarity	NPC32407
0.7424	Intermediate Similarity	NPC263548
0.7424	Intermediate Similarity	NPC606320
0.7385	Intermediate Similarity	NPC84319
0.7385	Intermediate Similarity	NPC52021
0.7385	Intermediate Similarity	NPC599947
0.7273	Intermediate Similarity	NPC472149
0.6857	Remote Similarity	NPC20235
0.6857	Remote Similarity	NPC299996
0.6765	Remote Similarity	NPC88116
0.6571	Remote Similarity	NPC247139
0.6522	Remote Similarity	NPC231063
0.6522	Remote Similarity	NPC282395
0.6522	Remote Similarity	NPC173744
0.6522	Remote Similarity	NPC204961
0.6522	Remote Similarity	NPC73004
0.6522	Remote Similarity	NPC300351
0.6522	Remote Similarity	NPC609452
0.6429	Remote Similarity	NPC305464
0.6429	Remote Similarity	NPC19376
0.6429	Remote Similarity	NPC25848
0.6377	Remote Similarity	NPC51700
0.6377	Remote Similarity	NPC88716
0.6377	Remote Similarity	NPC68160
0.6301	Remote Similarity	NPC479743
0.6286	Remote Similarity	NPC110308
0.6197	Remote Similarity	NPC87095
0.6143	Remote Similarity	NPC306541
0.6056	Remote Similarity	NPC61543
0.6056	Remote Similarity	NPC293048
0.6056	Remote Similarity	NPC225585
0.6	Remote Similarity	NPC96916
0.5972	Remote Similarity	NPC40092
0.5857	Remote Similarity	NPC43686
0.5844	Remote Similarity	NPC96693
0.5753	Remote Similarity	NPC202728
0.5753	Remote Similarity	NPC173089
0.5753	Remote Similarity	NPC158059
0.5714	Remote Similarity	NPC230151
0.5676	Remote Similarity	NPC201657
0.5641	Remote Similarity	NPC188833
0.5634	Remote Similarity	NPC274050
0.5634	Remote Similarity	NPC162632
0.5634	Remote Similarity	NPC609710
0.56	Remote Similarity	NPC127689
0.5556	Remote Similarity	NPC480946
0.5556	Remote Similarity	NPC187722
0.5556	Remote Similarity	NPC130577
0.5556	Remote Similarity	NPC142415
0.5556	Remote Similarity	NPC102683
0.5541	Remote Similarity	NPC256247
0.5541	Remote Similarity	NPC145667
0.5541	Remote Similarity	NPC293564
0.5541	Remote Similarity	NPC477288
0.5526	Remote Similarity	NPC157113
0.5526	Remote Similarity	NPC481318
0.5479	Remote Similarity	NPC307282
0.5479	Remote Similarity	NPC182797
0.5479	Remote Similarity	NPC52169
0.5479	Remote Similarity	NPC488562
0.5467	Remote Similarity	NPC35239
0.5467	Remote Similarity	NPC88847
0.5467	Remote Similarity	NPC191412
0.5467	Remote Similarity	NPC114159
0.5467	Remote Similarity	NPC6818
0.5405	Remote Similarity	NPC106112
0.5405	Remote Similarity	NPC261935
0.5405	Remote Similarity	NPC111214
0.5405	Remote Similarity	NPC481360
0.5405	Remote Similarity	NPC481314
0.5395	Remote Similarity	NPC62516
0.5342	Remote Similarity	NPC274330
0.5342	Remote Similarity	NPC477289
0.5333	Remote Similarity	NPC488214
0.5333	Remote Similarity	NPC136697
0.5325	Remote Similarity	NPC116457
0.5325	Remote Similarity	NPC117663
0.5278	Remote Similarity	NPC488506
0.5278	Remote Similarity	NPC220498
0.527	Remote Similarity	NPC270768
0.527	Remote Similarity	NPC59263
0.527	Remote Similarity	NPC210106
0.527	Remote Similarity	NPC229281
0.527	Remote Similarity	NPC121798
0.527	Remote Similarity	NPC234346
0.527	Remote Similarity	NPC606443
0.5263	Remote Similarity	NPC9613
0.5263	Remote Similarity	NPC132824
0.525	Remote Similarity	NPC54909
0.5217	Remote Similarity	NPC479747
0.5217	Remote Similarity	NPC479746
0.52	Remote Similarity	NPC38754
0.5195	Remote Similarity	NPC148964
0.5135	Remote Similarity	NPC136313
0.5128	Remote Similarity	NPC187933
0.5128	Remote Similarity	NPC174663
0.5128	Remote Similarity	NPC284865
0.507	Remote Similarity	NPC478657
0.5068	Remote Similarity	NPC49320
0.5067	Remote Similarity	NPC282616
0.5067	Remote Similarity	NPC307335
0.5067	Remote Similarity	NPC74855
0.5067	Remote Similarity	NPC488213
0.5065	Remote Similarity	NPC485589
0.5062	Remote Similarity	NPC233012
0.5059	Remote Similarity	NPC57362

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC37221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6788
0.1-0.2	2316
0.2-0.3	42
0.3-0.4	4
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