NPASS Compound

Natural Product: NPC481322

Natural Product ID	NPC481322
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PYUUJQUMSQBUIN-NCNQYBFESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 -6.0000 2.4859 -0.1271 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3828 1.3811 0.1653 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0717 0.0618 -0.0832 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9885 -1.0090 -0.0845 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8867 -0.4671 -0.9759 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8514 -1.5053 -1.3220 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0291 -1.8522 -0.1189 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1144 -0.7784 0.3568 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2208 -0.7851 1.8946 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7444 0.4828 -0.1000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9584 1.5261 -0.3056 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4902 1.6225 -0.1437 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 0.3427 0.2622 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5249 0.3739 -0.1363 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8155 0.5601 -1.5568 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0711 1.6405 0.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5375 1.7431 0.5568 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3220 0.5164 0.2712 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6608 -0.7772 0.5896 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1658 -1.2261 1.9764 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2138 -1.8690 -0.3387 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1800 -0.7362 0.6098 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5189 -2.0706 0.3789 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0480 -1.9870 0.7464 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3318 -0.9068 -0.0447 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4116 -1.4132 -1.4404 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8423 0.5148 -1.0504 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9204 2.2843 1.8119 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1697 0.7094 -0.3579 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0074 1.2563 0.7463 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6199 2.6688 1.1310 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5615 -0.1180 -2.2651 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4918 1.0800 -2.6315 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2329 -1.0147 -3.0441 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5044 3.4391 0.0514 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9893 2.4673 -0.5412 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5293 0.0401 -1.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8270 -0.1628 0.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6583 -1.2657 0.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4135 -1.8849 -0.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4516 -2.4422 -1.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3137 -1.3035 -2.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5749 -2.8358 -0.2970 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8126 -2.0876 0.6734 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3045 -0.7496 2.1924 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9100 -1.7463 2.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -0.0097 2.3659 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3827 2.5044 -0.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6532 2.4211 0.6451 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 2.0758 -1.0608 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1168 0.3628 1.4001 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3986 1.5052 -1.8067 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9043 0.7136 -2.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4010 -0.2295 -2.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6518 2.4836 -0.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6056 1.6796 1.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9006 2.5281 -0.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2777 0.6041 0.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2707 -0.2922 2.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1952 -1.6423 1.8666 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4648 -1.9126 2.4497 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2687 -1.5558 -1.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2866 -2.0088 -0.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7259 -2.8318 -0.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8900 -0.5111 1.6910 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7434 -2.5590 -0.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9655 -2.7482 1.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0437 -1.7866 1.8304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6866 -3.0070 0.4834 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0023 -0.7311 -2.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0057 -2.4437 -1.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4664 -1.5962 -1.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5490 1.1847 -1.1535 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7800 3.2788 1.8031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2882 1.5283 -1.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1678 0.6061 1.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6870 2.5963 1.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4905 3.2957 0.2390 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4461 3.0793 1.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5834 -0.7846 -3.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 27 1 0 17 28 1 0 10 29 1 0 29 30 1 0 30 31 1 0 5 32 1 6 32 33 2 0 32 34 1 0 30 2 1 0 29 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 9 45 1 0 9 46 1 0 9 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 1 15 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 6 18 58 1 1 20 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 21 64 1 0 22 65 1 1 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 26 70 1 0 26 71 1 0 26 72 1 0 27 73 1 0 28 74 1 0 29 75 1 6 30 76 1 1 31 77 1 0 31 78 1 0 31 79 1 0 34 80 1 0 M END

Standard InCHIKey	PYUUJQUMSQBUIN-NCNQYBFESA-N
Standard InCHI	InChI=1S/C30H46O4/c1-17-10-13-30(25(33)34)15-14-28(6)19(23(30)18(17)2)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h8,18,20-24,31-32H,1,9-16H2,2-7H3,(H,33,34)/t18-,20+,21-,22+,23-,24-,27-,28+,29+,30-/m0/s1
SMILES	C=C1CC[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]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.486 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.094 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.046 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
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:	0.412	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.103	Fsp³:	0.833
MCE-18:	104.945 ? 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:	0.888	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.114 ? 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:	0.332	Promiscuous compounds:	0.089

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.568	MDCK Permeability:	-5.119
Pgp-inhibitor:	0.004	Pgp-substrate:	0.022
PAMPA:	0.998 ? 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%):	0.81	30% Bioavailability (F30%):	0.525
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.627	MRP1:	0.984
Plasma Protein Binding (PPB):	94.544%	Volume Distribution (VD):	-0.388
Fu:	5.43% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.98	BCRP inhibitor:	0.121
BSEP inhibitor:	0.916

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.023
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.001 ? 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):

3.557

Half-life (T1/2):

0.973

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.034
Human Hepatotoxicity (H-HT):	0.569	Drug-induced Liver Injury (DILI):	0.697
AMES Toxicity:	0.256	Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.188	Skin Sensitization:	0.759
Carcinogencity:	0.703	Eye Corrosion:	0.018
Eye Irritation:	0.671	Respiratory Toxicity:	0.615
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.795
Hematotoxicity:	0.483	Drug-induced Nephrotoxicity:	0.936
Genotoxicity:	0.345	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.071	Hek293 Cytotoxicity:	0.062
BCF:	1.069 ? 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:	3.682 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.34 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.63 ? 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
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27797185]
NPO4734	Syzygium nervosum	Species	Myrtaceae	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 NPC481322 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	23026
0.1-0.2	22680
0.2-0.3	3379
0.3-0.4	498
0.4-0.5	183
0.5-0.6	57
0.6-0.7	22
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC25299
0.8615	High Similarity	NPC20235
0.8615	High Similarity	NPC299996
0.7727	Intermediate Similarity	NPC71074
0.7727	Intermediate Similarity	NPC37221
0.7727	Intermediate Similarity	NPC605937
0.7143	Intermediate Similarity	NPC127689
0.7059	Intermediate Similarity	NPC84319
0.7059	Intermediate Similarity	NPC52021
0.7059	Intermediate Similarity	NPC599947
0.6957	Remote Similarity	NPC472149
0.6857	Remote Similarity	NPC259733
0.6857	Remote Similarity	NPC158371
0.6857	Remote Similarity	NPC207922
0.662	Remote Similarity	NPC32407
0.662	Remote Similarity	NPC263548
0.662	Remote Similarity	NPC606320
0.6575	Remote Similarity	NPC481318
0.6316	Remote Similarity	NPC481320
0.6267	Remote Similarity	NPC479743
0.625	Remote Similarity	NPC300351
0.6234	Remote Similarity	NPC481319
0.6222	Remote Similarity	NPC479740
0.6222	Remote Similarity	NPC479741
0.6027	Remote Similarity	NPC231063
0.6027	Remote Similarity	NPC282395
0.6027	Remote Similarity	NPC173744
0.6027	Remote Similarity	NPC88116
0.6027	Remote Similarity	NPC204961
0.6027	Remote Similarity	NPC73004
0.6027	Remote Similarity	NPC110308
0.6027	Remote Similarity	NPC609452
0.5946	Remote Similarity	NPC87095
0.589	Remote Similarity	NPC51700
0.589	Remote Similarity	NPC88716
0.589	Remote Similarity	NPC306541
0.589	Remote Similarity	NPC68160
0.5867	Remote Similarity	NPC247139
0.5753	Remote Similarity	NPC96916
0.5733	Remote Similarity	NPC305464
0.5733	Remote Similarity	NPC19376
0.5733	Remote Similarity	NPC25848
0.5696	Remote Similarity	NPC230151
0.5652	Remote Similarity	NPC324798
0.5652	Remote Similarity	NPC479742
0.5616	Remote Similarity	NPC43686
0.5513	Remote Similarity	NPC116457
0.5513	Remote Similarity	NPC174663
0.5432	Remote Similarity	NPC188833
0.5432	Remote Similarity	NPC96693
0.5405	Remote Similarity	NPC609710
0.5395	Remote Similarity	NPC61543
0.5395	Remote Similarity	NPC293048
0.5395	Remote Similarity	NPC225585
0.5395	Remote Similarity	NPC481360
0.5376	Remote Similarity	NPC479739
0.5333	Remote Similarity	NPC480946
0.5333	Remote Similarity	NPC187722
0.5333	Remote Similarity	NPC130577
0.5333	Remote Similarity	NPC142415
0.5333	Remote Similarity	NPC102683
0.5326	Remote Similarity	NPC488214
0.5325	Remote Similarity	NPC202728
0.5325	Remote Similarity	NPC158059
0.5325	Remote Similarity	NPC293564
0.5263	Remote Similarity	NPC182797
0.5263	Remote Similarity	NPC52169
0.5263	Remote Similarity	NPC488562
0.5256	Remote Similarity	NPC88847
0.5256	Remote Similarity	NPC201657
0.5195	Remote Similarity	NPC106112
0.5195	Remote Similarity	NPC261935
0.5195	Remote Similarity	NPC111214
0.519	Remote Similarity	NPC130520
0.5132	Remote Similarity	NPC477289
0.5128	Remote Similarity	NPC256247
0.5128	Remote Similarity	NPC173089
0.5128	Remote Similarity	NPC145667
0.5128	Remote Similarity	NPC477288
0.5125	Remote Similarity	NPC157113
0.5067	Remote Similarity	NPC488506
0.5067	Remote Similarity	NPC220498
0.5065	Remote Similarity	NPC307282
0.5065	Remote Similarity	NPC307335
0.5065	Remote Similarity	NPC74855
0.5063	Remote Similarity	NPC35239
0.5063	Remote Similarity	NPC485589
0.506	Remote Similarity	NPC54909
0.506	Remote Similarity	NPC233012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6682
0.1-0.2	2413
0.2-0.3	50
0.3-0.4	5
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