NPASS Compound

Natural Product: NPC481314

Natural Product ID	NPC481314
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UPOWCSINRYQITP-NUXQCMEFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	132577488
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 4.9307 -0.7098 2.7849 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9424 0.3775 1.7739 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4784 1.6889 2.3220 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7230 0.0681 0.5237 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2034 -1.0399 -0.2891 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7462 -1.3288 -0.2672 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1683 -1.1222 -1.6378 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7029 -1.2842 -1.7788 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9262 -0.3800 -0.7997 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2462 1.0202 -1.3318 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5463 -0.6673 0.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7684 -1.0357 1.4960 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7041 -1.2016 1.4635 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2048 -0.2628 0.4109 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6859 -0.0487 0.4134 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5126 -1.3036 0.4876 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0351 0.7139 1.7045 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3843 1.4056 1.6097 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5321 2.3174 0.4653 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3374 1.4538 -0.7909 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4830 0.5514 -1.0527 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3337 2.5006 -1.9134 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3172 3.4177 -1.7639 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9997 0.8291 -0.7396 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6732 0.0886 -2.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1368 0.0688 -2.0795 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5547 -0.6545 -0.8719 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7954 -2.1247 -1.2293 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7667 2.9074 0.4882 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5475 2.0450 2.8573 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2335 -1.0302 2.7265 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9799 -0.5931 0.8004 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5292 0.7048 1.2311 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6089 -2.8100 -0.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6436 -3.5062 0.0901 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4029 -3.4621 0.0901 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8288 -0.5525 3.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0706 -1.7275 2.3677 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0620 -0.6204 3.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3959 1.5188 2.9328 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7201 2.2643 2.8595 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7979 2.3147 1.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7092 1.0037 -0.0875 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7785 -0.0955 0.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8283 -1.9518 -0.0317 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5187 -0.8433 -1.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5986 -0.1991 -2.0599 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6271 -1.9459 -2.2710 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4851 -0.9327 -2.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4360 -2.3366 -1.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0672 1.0518 -2.4436 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3375 1.2098 -1.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6170 1.7913 -0.9020 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2152 -1.2621 2.5001 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8774 -2.2721 1.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7776 0.7482 0.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3667 -1.2267 1.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8754 -2.1075 0.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0160 -1.5784 -0.4535 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2530 1.4162 1.9850 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2685 -0.0358 2.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1987 0.6235 1.5977 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6918 3.0544 0.4655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2334 -0.0966 -1.8984 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3444 1.1916 -1.4059 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8590 -0.0261 -0.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2845 3.0861 -1.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4724 2.0797 -2.9038 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5935 4.2447 -1.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2561 1.6839 -0.6904 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1146 -0.8868 -2.1328 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9769 0.7226 -2.8588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9702 -0.4787 -3.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8871 1.1458 -2.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4909 -2.2290 -2.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8898 -2.3265 -1.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2322 -2.8199 -0.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3751 2.5395 1.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6839 1.3115 3.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5406 -1.1748 3.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1979 -1.2494 1.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8955 1.0890 2.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7561 1.4671 0.4972 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2769 -4.1754 0.8175 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 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 19 29 1 0 18 30 1 0 13 31 1 0 11 32 1 0 32 33 1 0 6 34 1 1 34 35 2 0 34 36 1 0 33 2 1 0 32 6 1 0 27 9 1 0 27 14 1 0 24 15 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 0 5 46 1 0 7 47 1 0 7 48 1 0 8 49 1 0 8 50 1 0 10 51 1 0 10 52 1 0 10 53 1 0 12 54 1 0 13 55 1 6 14 56 1 1 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 6 19 63 1 1 21 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 23 69 1 0 24 70 1 1 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 28 75 1 0 28 76 1 0 28 77 1 0 29 78 1 0 30 79 1 0 31 80 1 0 32 81 1 1 33 82 1 0 33 83 1 0 36 84 1 0 M END

Standard InCHIKey	UPOWCSINRYQITP-NUXQCMEFSA-N
Standard InCHI	InChI=1S/C30H48O6/c1-25(2)9-11-30(24(35)36)12-10-28(5)17(18(30)14-25)13-19(32)22-26(3)15-20(33)23(34)27(4,16-31)21(26)7-8-29(22,28)6/h13,18-23,31-34H,7-12,14-16H2,1-6H3,(H,35,36)/t18-,19+,20+,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1
SMILES	CC1(C)CC[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]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.35	Volume:	532.122 ? Van der Waals volume.
Dense:	0.948	LogP:	2.269 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.294 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.82 ? 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:	0.361	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.189	Fsp³:	0.9
MCE-18:	110.772 ? 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:	0.608	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? 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:	0.27	Promiscuous compounds:	0.202

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.569	MDCK Permeability:	-5.05
Pgp-inhibitor:	0.0	Pgp-substrate:	0.023
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):	0.041
20% Bioavailability (F20%):	0.657	30% Bioavailability (F30%):	0.178
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.431	MRP1:	0.898
Plasma Protein Binding (PPB):	84.025%	Volume Distribution (VD):	-0.378
Fu:	12.043% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.468	BCRP inhibitor:	0.003
BSEP inhibitor:	0.646

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.032
HLM stability:	0.385 ? 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):

3.013

Half-life (T1/2):

1.703

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.038
Human Hepatotoxicity (H-HT):	0.692	Drug-induced Liver Injury (DILI):	0.565
AMES Toxicity:	0.266	Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.137	Skin Sensitization:	0.847
Carcinogencity:	0.642	Eye Corrosion:	0.002
Eye Irritation:	0.381	Respiratory Toxicity:	0.467
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.931
Hematotoxicity:	0.359	Drug-induced Nephrotoxicity:	0.958
Genotoxicity:	0.27	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.022	Hek293 Cytotoxicity:	0.036
BCF:	0.687 ? 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:	3.424 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.059 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.123 ? 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
GI	1
Inhibition	6

Activity Type	# Activity
Cell line	10

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	GI	<	5.0	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	74.9	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	69.9	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	68.1	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	65.6	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	57.7	%	PMID[27797185]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	53.7	%	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 NPC481314 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	22742
0.1-0.2	24194
0.2-0.3	2432
0.3-0.4	318
0.4-0.5	107
0.5-0.6	49
0.6-0.7	9
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
0.7538	Intermediate Similarity	NPC231063
0.7538	Intermediate Similarity	NPC282395
0.7424	Intermediate Similarity	NPC40092
0.7246	Intermediate Similarity	NPC481315
0.7206	Intermediate Similarity	NPC481316
0.7101	Intermediate Similarity	NPC481318
0.6618	Remote Similarity	NPC307282
0.6522	Remote Similarity	NPC110308
0.6522	Remote Similarity	NPC609452
0.6486	Remote Similarity	NPC80566
0.6377	Remote Similarity	NPC84319
0.6377	Remote Similarity	NPC52021
0.6377	Remote Similarity	NPC599947
0.6286	Remote Similarity	NPC88116
0.6111	Remote Similarity	NPC201657
0.5972	Remote Similarity	NPC145667
0.5915	Remote Similarity	NPC270768
0.5915	Remote Similarity	NPC59263
0.5915	Remote Similarity	NPC210106
0.5833	Remote Similarity	NPC173744
0.5833	Remote Similarity	NPC204961
0.5833	Remote Similarity	NPC73004
0.5753	Remote Similarity	NPC32407
0.5753	Remote Similarity	NPC263548
0.5753	Remote Similarity	NPC606320
0.5676	Remote Similarity	NPC247139
0.5616	Remote Similarity	NPC106112
0.5616	Remote Similarity	NPC261935
0.5616	Remote Similarity	NPC472149
0.5616	Remote Similarity	NPC481360
0.56	Remote Similarity	NPC607666
0.56	Remote Similarity	NPC608261
0.56	Remote Similarity	NPC611078
0.5526	Remote Similarity	NPC20235
0.5526	Remote Similarity	NPC299996
0.5526	Remote Similarity	NPC117663
0.5479	Remote Similarity	NPC32118
0.5443	Remote Similarity	NPC481319
0.5405	Remote Similarity	NPC130278
0.5405	Remote Similarity	NPC37221
0.5342	Remote Similarity	NPC480946
0.5342	Remote Similarity	NPC474806
0.5342	Remote Similarity	NPC130577
0.5342	Remote Similarity	NPC142415
0.5342	Remote Similarity	NPC102683
0.5342	Remote Similarity	NPC133579
0.5316	Remote Similarity	NPC481320
0.5263	Remote Similarity	NPC91010
0.5256	Remote Similarity	NPC479743
0.52	Remote Similarity	NPC271614
0.52	Remote Similarity	NPC158141
0.5132	Remote Similarity	NPC305464
0.5132	Remote Similarity	NPC19376
0.5132	Remote Similarity	NPC25848
0.5132	Remote Similarity	NPC298554
0.5128	Remote Similarity	NPC600832
0.5067	Remote Similarity	NPC282616
0.5067	Remote Similarity	NPC275809
0.5067	Remote Similarity	NPC121798
0.5067	Remote Similarity	NPC64872
0.5067	Remote Similarity	NPC37038
0.5067	Remote Similarity	NPC25906
0.5067	Remote Similarity	NPC234346
0.5065	Remote Similarity	NPC88847

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6255
0.1-0.2	2847
0.2-0.3	43
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