NPASS Compound

Natural Product: NPC481017

Natural Product ID	NPC481017
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FZYTXXDTFJSGHX-JZKCPRDQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	127037781
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

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 84 0 0 0 0 0 0 0 0999 V2000 6.7924 -1.3486 -3.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8425 -0.6255 -2.0700 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7325 -0.9908 -1.1342 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3966 -0.6945 -1.7083 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3447 -0.1964 -2.8596 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2375 -0.9441 -1.0307 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9294 -0.6715 -1.5535 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2078 0.2745 -0.6503 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6735 1.3651 -0.1120 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7173 2.1141 0.7580 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0559 1.0318 1.5899 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7940 0.1007 0.7879 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2262 0.5132 0.7839 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3690 1.5536 1.9519 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1837 -0.5409 1.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2889 -1.8216 0.5679 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3006 -2.7440 1.2227 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9522 -2.3630 2.2969 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5577 -4.0601 0.6655 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9109 -4.4634 -0.4174 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6269 1.2772 -0.4088 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1597 1.3149 -0.5469 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9511 1.0338 -1.6967 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9750 -0.1043 -1.7402 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1771 -0.3113 -0.5162 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3659 -1.7552 -0.4478 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0258 -1.8499 0.7963 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7911 -2.7991 1.7510 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0680 -3.6683 1.5418 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5987 -2.7292 3.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2254 -1.8206 -1.5187 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5499 -1.2736 -2.2121 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2521 -1.6829 -3.4617 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3234 3.0373 1.6046 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0202 4.3902 1.6491 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1339 4.7974 0.8633 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6759 5.3542 2.5571 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0823 6.7206 2.3124 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8068 -1.6998 -3.6716 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4342 -0.6570 -4.1568 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1291 -2.2351 -3.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9017 0.4737 -2.2364 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7992 -0.8987 -1.5649 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8388 -0.3303 -0.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8407 -2.0308 -0.7964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0437 -0.2372 -2.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6825 1.7469 -0.2556 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0581 2.5298 0.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3595 1.5186 2.4534 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9426 0.4472 2.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8027 -0.8614 1.4073 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8732 2.4963 1.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2061 1.1033 2.9155 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4725 1.8551 1.9657 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9159 -0.7104 2.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2268 -0.1204 1.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3395 -2.3853 0.6868 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5248 -1.8122 -0.4893 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6667 -3.0326 2.7468 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8186 -1.4146 2.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2652 -4.7093 1.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1793 -3.8338 -0.9158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0912 -5.4284 -0.8365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4135 2.3713 -0.1836 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5846 0.3096 -0.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4466 1.9125 -1.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6317 1.8489 0.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7568 0.7703 -2.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4908 1.9384 -2.1507 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2661 0.1684 -2.5753 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3885 -2.5181 -0.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5317 -1.6856 3.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6608 -2.8943 2.7512 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2255 -3.4152 3.7785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5238 -0.9447 -4.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9847 -2.5319 -3.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2779 -2.1543 -3.6426 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7734 5.4045 2.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4514 5.0396 3.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6088 7.2215 1.4723 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0130 6.6294 1.9632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0515 7.3358 3.2345 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 13 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 26 31 1 0 24 32 1 0 32 33 1 0 10 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 1 0 31 7 1 0 25 8 1 6 25 12 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 2 43 1 0 3 44 1 0 3 45 1 0 7 46 1 6 9 47 1 0 10 48 1 6 11 49 1 0 11 50 1 0 12 51 1 1 14 52 1 0 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 1 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 24 70 1 6 26 71 1 6 30 72 1 0 30 73 1 0 30 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 37 78 1 0 37 79 1 0 38 80 1 0 38 81 1 0 38 82 1 0 M END

Standard InCHIKey	FZYTXXDTFJSGHX-JZKCPRDQSA-N
Standard InCHI	InChI=1S/C30H44O8/c1-9-12-26(33)37-27-22-16-21(36-25(32)11-3)17-23-29(7,14-13-18(4)10-2)19(5)15-24(34-8)30(22,23)28(38-27)35-20(6)31/h10,16,19,21,23-24,27-28H,2,4,9,11-15,17H2,1,3,5-8H3/t19-,21+,23+,24+,27+,28-,29-,30-/m1/s1
SMILES	CCCC(=O)O[C@@H]1C2=C[C@@H](C[C@H]3[C@](C)(CCC(=C)C=C)[C@H](C)C[C@@H]([C@@]23[C@H](OC(=O)C)O1)OC)OC(=O)CC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	532.3	Volume:	556.27 ? Van der Waals volume.
Dense:	0.957	LogP:	3.999 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.517 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.455 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	20.0
TPSA:	97.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.151	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.769	Fsp³:	0.7
MCE-18:	88.196 ? 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:	0.542	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.376	Promiscuous compounds:	0.687

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.777	MDCK Permeability:	-4.739
Pgp-inhibitor:	0.975	Pgp-substrate:	0.891
PAMPA:	0.08 ? 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%):	0.993	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.399	MRP1:	0.995
Plasma Protein Binding (PPB):	85.74%	Volume Distribution (VD):	-0.192
Fu:	14.56% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.953
OATP1B3 inhibitor:	0.479	BCRP inhibitor:	0.709
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.295	CYP1A2-substrate:	0.709
CYP2C19-inhibitor:	0.892	CYP2C19-substrate:	0.29
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.007	CYP3A4-substrate:	0.696
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

8.627

Half-life (T1/2):

0.763

ADMET: Toxicity

hERG Blockers:	0.123	hERG Blockers (10um):	0.523
Human Hepatotoxicity (H-HT):	0.392	Drug-induced Liver Injury (DILI):	0.519
AMES Toxicity:	0.849	Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.97	Skin Sensitization:	0.979
Carcinogencity:	0.736	Eye Corrosion:	0.003
Eye Irritation:	0.075	Respiratory Toxicity:	0.855
Drug-induced Neurotoxicity:	0.77	Ototoxicity:	0.508
Hematotoxicity:	0.489	Drug-induced Nephrotoxicity:	0.742
Genotoxicity:	0.837	RPMI-8226 Immunitoxicity:	0.271
A549 Cytotoxicity:	0.274	Hek293 Cytotoxicity:	0.311
BCF:	0.903 ? 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:	3.867 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.673 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.102 ? 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
NPO40063	Casearia graveolens	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26474353]
NPO40063	Casearia graveolens	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31916761]

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
EC50	1

Activity Type	# Activity
Cell line	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
NPT681	Cell line	PC-12	Rattus norvegicus	EC50	>	45000.0	nM	PMID[26474353]

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 NPC481017 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	23266
0.1-0.2	24940
0.2-0.3	1513
0.3-0.4	30
0.4-0.5	46
0.5-0.6	26
0.6-0.7	14
0.7-0.8	0
0.8-0.85	3
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9649	High Similarity	NPC472186
0.9483	High Similarity	NPC488649
0.9138	High Similarity	NPC481019
0.8966	High Similarity	NPC481020
0.8871	High Similarity	NPC472187
0.8793	High Similarity	NPC481018
0.8475	Intermediate Similarity	NPC171598
0.8305	Intermediate Similarity	NPC472189
0.8197	Intermediate Similarity	NPC318917
0.7937	Intermediate Similarity	NPC471366
0.7937	Intermediate Similarity	NPC476800
0.7937	Intermediate Similarity	NPC488237
0.7903	Intermediate Similarity	NPC471362
0.7903	Intermediate Similarity	NPC471372
0.7778	Intermediate Similarity	NPC472188
0.7692	Intermediate Similarity	NPC473545
0.7273	Intermediate Similarity	NPC471365
0.7231	Intermediate Similarity	NPC488236
0.6923	Remote Similarity	NPC600724
0.6571	Remote Similarity	NPC488963
0.6571	Remote Similarity	NPC48548
0.6515	Remote Similarity	NPC606965
0.6418	Remote Similarity	NPC132395
0.6418	Remote Similarity	NPC471364
0.6324	Remote Similarity	NPC479935
0.6286	Remote Similarity	NPC7644
0.6176	Remote Similarity	NPC479934
0.6176	Remote Similarity	NPC488651
0.6176	Remote Similarity	NPC488648
0.6143	Remote Similarity	NPC473204
0.6081	Remote Similarity	NPC127933
0.6	Remote Similarity	NPC479943
0.597	Remote Similarity	NPC603601
0.5811	Remote Similarity	NPC488219
0.5753	Remote Similarity	NPC217921
0.5753	Remote Similarity	NPC88013
0.5753	Remote Similarity	NPC135015
0.5733	Remote Similarity	NPC488221
0.5733	Remote Similarity	NPC488220
0.5733	Remote Similarity	NPC488216
0.5634	Remote Similarity	NPC479936
0.5634	Remote Similarity	NPC488235
0.5616	Remote Similarity	NPC479940
0.5595	Remote Similarity	NPC488962
0.5526	Remote Similarity	NPC125423
0.5455	Remote Similarity	NPC40728
0.5443	Remote Similarity	NPC486752
0.5417	Remote Similarity	NPC479939
0.5362	Remote Similarity	NPC488650
0.5362	Remote Similarity	NPC481022
0.5342	Remote Similarity	NPC479937
0.5333	Remote Similarity	NPC475889
0.5333	Remote Similarity	NPC7613
0.5333	Remote Similarity	NPC479942
0.5333	Remote Similarity	NPC238397
0.527	Remote Similarity	NPC479938
0.5263	Remote Similarity	NPC479941
0.5132	Remote Similarity	NPC609715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7371
0.1-0.2	1759
0.2-0.3	20
0.3-0.4	0
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