NPASS Compound

Natural Product: NPC40092

Natural Product ID	NPC40092
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FFPKNVKIBUBHMY-CCEBUSCFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	51041097
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 84 88 0 0 0 0 0 0 0 0999 V2000 5.6667 -1.9239 -1.6172 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8649 -0.6384 -1.7422 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6584 0.4674 -1.1237 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3270 0.8296 0.2774 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9046 1.2990 0.3936 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3534 1.2227 1.7755 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8993 1.2377 1.9929 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0997 0.3846 0.9853 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4854 -1.0172 1.4596 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6847 0.7354 -0.3083 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9203 1.2655 -1.2316 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5334 1.5542 -1.0838 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0875 0.4962 -0.1655 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5973 0.4434 -0.1539 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2863 1.6587 0.3380 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0726 0.2463 -1.5895 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4654 -0.3189 -1.7081 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7766 -1.5002 -0.9060 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2844 -1.3604 0.5195 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3409 -0.7049 1.3307 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2081 -2.8304 0.9773 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5346 -3.3126 0.8428 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9362 -0.8100 0.6020 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4722 -0.5861 2.0130 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9323 -0.5784 2.0161 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3876 0.5546 1.1313 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6218 1.8051 1.9464 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1609 -1.6616 -0.8419 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5971 -0.6801 -3.0737 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0531 1.5382 -2.3686 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0986 0.5438 -0.6420 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5794 -0.8188 -0.9458 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5317 -1.5366 -1.7684 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9311 2.7494 0.0557 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5946 3.6607 0.8717 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.1916 -1.1886 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2384 -1.9258 -0.6690 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4012 -2.0228 -2.4451 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0307 -2.8149 -1.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6100 -0.4418 -2.8090 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5226 1.3573 -1.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7613 0.2522 -1.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9923 1.7055 0.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5629 0.0217 1.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7894 2.1115 2.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8417 0.3687 2.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7168 0.8919 3.0374 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5767 2.2977 1.9833 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1829 -1.8193 0.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5845 -1.0607 1.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0666 -1.0988 2.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3759 1.5399 -2.2340 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7152 2.5822 -0.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7849 -0.4625 -0.6403 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1386 1.9266 -0.3615 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8104 1.5850 1.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6143 2.5362 0.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4184 -0.3684 -2.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2572 1.2832 -2.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2722 0.4410 -1.5531 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3735 -2.4142 -1.3962 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7757 0.1686 0.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2018 -1.3803 1.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0050 -0.3374 2.3156 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8799 -2.9472 2.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6236 -3.3575 0.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4998 -4.2901 0.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2322 -1.5992 0.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8563 0.2839 2.5211 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7281 -1.4639 2.6431 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7218 -0.4241 3.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6062 -1.5637 1.6156 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0909 1.7169 2.9168 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6906 1.8758 2.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3009 2.7324 1.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5927 -1.4924 -1.7164 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0247 0.0130 -3.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3809 1.4727 -3.0792 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3303 1.1082 -1.6073 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8552 -1.4831 -0.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4991 -1.2170 -1.5258 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5673 -2.6357 -1.6106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7929 -1.3611 -2.8327 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7154 4.1042 -1.3759 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 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 18 28 1 0 17 29 1 0 12 30 1 0 10 31 1 0 31 32 1 0 32 33 1 0 5 34 1 6 34 35 2 0 34 36 1 0 32 2 1 0 31 5 1 0 26 8 1 0 26 13 1 0 23 14 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 6 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 9 49 1 0 9 50 1 0 9 51 1 0 11 52 1 0 12 53 1 1 13 54 1 6 15 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 18 61 1 6 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 23 68 1 6 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 29 77 1 0 30 78 1 0 31 79 1 6 32 80 1 1 33 81 1 0 33 82 1 0 33 83 1 0 36 84 1 0 M END

Standard InCHIKey	FFPKNVKIBUBHMY-CCEBUSCFSA-N
Standard InCHI	InChI=1S/C30H48O6/c1-16-7-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)13-19(32)23-26(3)14-20(33)24(34)27(4,15-31)21(26)8-9-29(23,28)6/h13,16-17,19-24,31-34H,7-12,14-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21-,22+,23-,24+,26+,27+,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=C[C@H]([C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O)O)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.35	Volume:	532.122 ? Van der Waals volume.
Dense:	0.948	LogP:	2.298 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.416 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.973 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	118.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.363	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.273	Fsp³:	0.9
MCE-18:	108.07 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.536	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.225 ? 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:	0.254	Promiscuous compounds:	0.175

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.642	MDCK Permeability:	-5.103
Pgp-inhibitor:	0.003	Pgp-substrate:	0.149
PAMPA:	1.0 ? 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):	0.081
20% Bioavailability (F20%):	0.761	30% Bioavailability (F30%):	0.382
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.536	MRP1:	0.864
Plasma Protein Binding (PPB):	80.399%	Volume Distribution (VD):	-0.449
Fu:	14.723% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.442	BCRP inhibitor:	0.052
BSEP inhibitor:	0.769

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.03	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.012
HLM stability:	0.037 ? 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):

3.125

Half-life (T1/2):

1.946

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.03
Human Hepatotoxicity (H-HT):	0.657	Drug-induced Liver Injury (DILI):	0.592
AMES Toxicity:	0.283	Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.111	Skin Sensitization:	0.87
Carcinogencity:	0.647	Eye Corrosion:	0.002
Eye Irritation:	0.531	Respiratory Toxicity:	0.484
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.921
Hematotoxicity:	0.433	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.301	RPMI-8226 Immunitoxicity:	0.031
A549 Cytotoxicity:	0.027	Hek293 Cytotoxicity:	0.045
BCF:	0.495 ? 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:	3.205 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.759 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.825 ? 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
NPO25572	Symplocos lancifolia	Species	Symplocaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21288041]
NPO25572	Symplocos lancifolia	Species	Symplocaceae	Eukaryota	leaves	Bac Quang, Ha Giang Province, in Vietnam	n.a.	PMID[21288041]
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27797185]
NPO25572	Symplocos lancifolia	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25572	Symplocos lancifolia	Species	Symplocaceae	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
IC50	3
Inhibition	8
GI	1

Activity Type	# Activity
Cell line	12

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
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[27797185]
NPT465	Cell line	NCI-N87	Homo sapiens	IC50	>	10000.0	nM	PMID[27797185]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	<	50.0	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	GI	<	5.0	%	PMID[27797185]

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 NPC40092 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	22289
0.1-0.2	24471
0.2-0.3	2638
0.3-0.4	318
0.4-0.5	93
0.5-0.6	33
0.6-0.7	7
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	Natural Product ID
0.7761	Intermediate Similarity	NPC481318
0.7576	Intermediate Similarity	NPC32407
0.7576	Intermediate Similarity	NPC263548
0.7576	Intermediate Similarity	NPC606320
0.7424	Intermediate Similarity	NPC481314
0.7246	Intermediate Similarity	NPC117663
0.6812	Remote Similarity	NPC305464
0.6812	Remote Similarity	NPC19376
0.6812	Remote Similarity	NPC25848
0.6765	Remote Similarity	NPC479079
0.6571	Remote Similarity	NPC479077
0.6429	Remote Similarity	NPC71074
0.6429	Remote Similarity	NPC605937
0.5972	Remote Similarity	NPC61543
0.5972	Remote Similarity	NPC293048
0.5972	Remote Similarity	NPC225585
0.5972	Remote Similarity	NPC88116
0.5972	Remote Similarity	NPC37221
0.5867	Remote Similarity	NPC20235
0.5867	Remote Similarity	NPC299996
0.5811	Remote Similarity	NPC247139
0.5769	Remote Similarity	NPC481319
0.5753	Remote Similarity	NPC231063
0.5753	Remote Similarity	NPC282395
0.5753	Remote Similarity	NPC173744
0.5753	Remote Similarity	NPC204961
0.5753	Remote Similarity	NPC73004
0.5753	Remote Similarity	NPC609452
0.5676	Remote Similarity	NPC87095
0.5641	Remote Similarity	NPC481320
0.5584	Remote Similarity	NPC481315
0.557	Remote Similarity	NPC80566
0.5526	Remote Similarity	NPC481316
0.5526	Remote Similarity	NPC607666
0.5526	Remote Similarity	NPC608261
0.5526	Remote Similarity	NPC611078
0.5405	Remote Similarity	NPC51700
0.5405	Remote Similarity	NPC88716
0.5405	Remote Similarity	NPC68160
0.5385	Remote Similarity	NPC479743
0.5263	Remote Similarity	NPC173089
0.5195	Remote Similarity	NPC610635
0.5067	Remote Similarity	NPC274330
0.5065	Remote Similarity	NPC477288
0.5063	Remote Similarity	NPC600832
0.5062	Remote Similarity	NPC230151

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC40092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6157
0.1-0.2	2939
0.2-0.3	51
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