NPASS Compound

Natural Product: NPC245869

Natural Product ID	NPC245869
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AOXTVVMIAYODJX-HCOAJINSSA-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 85 88 0 0 0 0 0 0 0 0999 V2000 7.8206 -1.3795 0.7225 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0831 -0.3394 1.0627 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3807 -0.2760 2.3818 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9395 0.8060 0.1172 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4413 1.0065 -0.2554 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9024 -0.2006 -0.8966 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5063 -0.2363 -1.3968 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3303 -1.6453 -1.9981 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4360 -0.0480 -0.3812 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4849 1.3003 0.3273 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0434 1.8583 0.2524 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2770 0.6052 0.2229 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3455 -0.0606 1.5586 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0348 -0.2022 -0.8462 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4725 -1.5790 -0.8836 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0199 -1.6707 -0.8825 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7383 -0.6431 -0.0844 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2239 -0.7170 -0.2235 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7393 -0.9314 -1.5984 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6551 -1.9683 0.5713 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1378 -2.1439 0.5619 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9451 -0.9607 0.8942 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3605 0.3767 0.5760 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7243 1.2831 1.7759 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0189 1.0059 -0.6156 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8643 0.3996 0.5479 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3560 1.7618 0.2278 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8533 1.7929 0.4829 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1395 0.7220 -0.2969 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1429 1.1492 -1.7377 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1607 -1.0575 0.1748 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3242 0.6109 -2.5079 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3050 1.9615 0.8028 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9034 -2.1984 1.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3205 -1.4079 -0.2345 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0027 0.7329 2.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0887 -0.5167 3.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5567 -1.0051 2.3926 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5251 0.6532 -0.8028 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3997 1.9366 -0.7936 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9852 1.1085 0.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6432 -0.4673 -1.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0112 -1.1209 -0.2252 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0311 -2.3754 -1.2548 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7852 -1.6301 -2.9499 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3801 -1.9547 -2.3051 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5875 -0.8111 0.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1044 2.0457 -0.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7999 1.2388 1.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9615 2.5324 -0.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8177 2.4133 1.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4812 0.2957 2.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3911 -1.1842 1.5091 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2663 0.2091 2.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8386 0.2599 -1.8359 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9261 -2.2715 -0.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7859 -2.0373 -1.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2667 -2.6715 -0.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4081 -1.7749 -1.9221 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5439 -0.8985 1.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8507 -1.0104 -1.5443 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4286 -1.9740 -1.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4115 -0.2535 -2.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1976 -2.8765 0.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3244 -1.7928 1.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4233 -2.6108 -0.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3417 -2.9841 1.2940 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2716 -1.0539 1.9730 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8128 2.3277 1.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9345 1.2612 2.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6753 0.9811 2.2171 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7847 0.3298 -1.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3534 1.3229 -1.4148 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6305 1.9220 -0.3584 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5511 0.2161 1.6258 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6457 2.1832 -0.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7870 2.4506 1.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5099 2.7752 0.0418 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6155 1.8397 1.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0934 0.3386 -2.4635 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3608 1.8852 -1.9881 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1037 1.7033 -1.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9331 -0.8161 0.7104 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8495 1.4356 -2.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7313 2.7188 0.5437 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 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 22 31 1 0 7 32 1 6 4 33 1 0 14 9 1 0 29 17 1 0 29 12 1 0 26 18 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 6 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 8 44 1 0 8 45 1 0 8 46 1 0 9 47 1 1 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 13 52 1 0 13 53 1 0 13 54 1 0 14 55 1 6 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 21 66 1 0 21 67 1 0 22 68 1 1 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 25 74 1 0 26 75 1 1 27 76 1 0 27 77 1 0 28 78 1 0 28 79 1 0 30 80 1 0 30 81 1 0 30 82 1 0 31 83 1 0 32 84 1 0 33 85 1 0 M END

Standard InCHIKey	AOXTVVMIAYODJX-HCOAJINSSA-N
Standard InCHI	InChI=1S/C30H52O3/c1-19(2)22(31)12-18-30(8,33)21-11-16-28(6)20(21)9-10-24-27(5)15-14-25(32)26(3,4)23(27)13-17-29(24,28)7/h20-25,31-33H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29-,30+/m1/s1
SMILES	C=C(C)[C@@H](CC[C@@](C)([C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@@]21C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	460.39	Volume:	516.944 ? Van der Waals volume.
Dense:	0.891	LogP:	4.067 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.002 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.02 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.41	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.905	Fsp³:	0.933
MCE-18:	87.931 ? 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:	0.843	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.681	Promiscuous compounds:	0.323

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.214	MDCK Permeability:	-5.005
Pgp-inhibitor:	0.005	Pgp-substrate:	0.815
PAMPA:	0.979 ? 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%):	0.834	30% Bioavailability (F30%):	0.22
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.443	MRP1:	0.98
Plasma Protein Binding (PPB):	93.606%	Volume Distribution (VD):	-0.249
Fu:	5.83% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.371
BSEP inhibitor:	0.684

ADMET: Metabolism

CYP1A2-inhibitor:	0.038	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.696	CYP2C19-substrate:	0.349
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.17	CYP3A4-substrate:	0.897
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.91
HLM stability:	0.282 ? 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):

13.006

Half-life (T1/2):

0.609

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.251
Human Hepatotoxicity (H-HT):	0.703	Drug-induced Liver Injury (DILI):	0.044
AMES Toxicity:	0.401	Rat Oral Acute Toxicity:	0.474
Maximum Recommended Daily Dose:	0.84	Skin Sensitization:	0.991
Carcinogencity:	0.871	Eye Corrosion:	0.075
Eye Irritation:	0.702	Respiratory Toxicity:	0.961
Drug-induced Neurotoxicity:	0.196	Ototoxicity:	0.627
Hematotoxicity:	0.449	Drug-induced Nephrotoxicity:	0.877
Genotoxicity:	0.68	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.753	Hek293 Cytotoxicity:	0.59
BCF:	1.721 ? 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:	3.808 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.212 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.645 ? 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
NPO40939	Syzygium corticosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30057155]

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	4

Activity Type	# Activity
Cell line	4

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
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[30057155]
NPT400	Cell line	MDA-MB-435	Homo sapiens	IC50	>	10000.0	nM	PMID[30057155]
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[30057155]
NPT377	Cell line	OVCAR-3	Homo sapiens	IC50	>	10000.0	nM	PMID[30057155]

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 NPC245869 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	27639
0.1-0.2	18618
0.2-0.3	3053
0.3-0.4	414
0.4-0.5	79
0.5-0.6	47
0.6-0.7	5
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
0.75	Intermediate Similarity	NPC285761
0.75	Intermediate Similarity	NPC34930
0.717	Intermediate Similarity	NPC301707
0.6786	Remote Similarity	NPC145143
0.6607	Remote Similarity	NPC13554
0.6481	Remote Similarity	NPC185536
0.6111	Remote Similarity	NPC480925
0.6111	Remote Similarity	NPC48079
0.5965	Remote Similarity	NPC42853
0.5789	Remote Similarity	NPC144075
0.5789	Remote Similarity	NPC91573
0.5714	Remote Similarity	NPC192638
0.5714	Remote Similarity	NPC25511
0.5714	Remote Similarity	NPC600137
0.569	Remote Similarity	NPC231256
0.569	Remote Similarity	NPC178383
0.566	Remote Similarity	NPC232112
0.5593	Remote Similarity	NPC296701
0.5593	Remote Similarity	NPC3403
0.5593	Remote Similarity	NPC218616
0.5556	Remote Similarity	NPC131665
0.5556	Remote Similarity	NPC255387
0.5517	Remote Similarity	NPC301226
0.55	Remote Similarity	NPC119355
0.5439	Remote Similarity	NPC606606
0.5424	Remote Similarity	NPC237460
0.5424	Remote Similarity	NPC248830
0.5424	Remote Similarity	NPC212241
0.5357	Remote Similarity	NPC142712
0.5345	Remote Similarity	NPC66407
0.5333	Remote Similarity	NPC80530
0.5333	Remote Similarity	NPC273410
0.5323	Remote Similarity	NPC12774
0.5263	Remote Similarity	NPC129829
0.5254	Remote Similarity	NPC104387
0.5246	Remote Similarity	NPC246956
0.5246	Remote Similarity	NPC91387
0.5246	Remote Similarity	NPC74595
0.5246	Remote Similarity	NPC231680
0.5246	Remote Similarity	NPC270306
0.5246	Remote Similarity	NPC264665
0.5246	Remote Similarity	NPC269396
0.5238	Remote Similarity	NPC479792
0.5167	Remote Similarity	NPC58631
0.5085	Remote Similarity	NPC97534
0.5085	Remote Similarity	NPC195155
0.5082	Remote Similarity	NPC5767
0.5082	Remote Similarity	NPC211009
0.5082	Remote Similarity	NPC475742
0.5082	Remote Similarity	NPC93662
0.5079	Remote Similarity	NPC49599
0.5079	Remote Similarity	NPC479789
0.5079	Remote Similarity	NPC49627
0.5077	Remote Similarity	NPC483720
0.5077	Remote Similarity	NPC476071

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC245869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8057
0.1-0.2	1012
0.2-0.3	78
0.3-0.4	2
0.4-0.5	1
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