NPASS Compound

Natural Product: NPC329623

Natural Product ID	NPC329623
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PASSAFHUDJPXAL-JXHLGRMOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44584131
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 76 78 0 0 0 0 0 0 0 0999 V2000 6.0447 -3.5038 0.7902 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1311 -3.0102 0.0091 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8516 -2.4418 0.3851 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0177 -1.9719 -0.5377 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7488 -1.4057 -0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3761 -0.0517 -0.6919 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3553 -0.2805 -2.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2948 1.0546 -0.4149 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7378 0.6747 -0.1588 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9097 2.0085 0.6595 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5039 2.0816 1.0907 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4387 1.6028 -0.0007 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8796 1.5718 0.5006 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6309 0.5242 0.5181 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1962 -0.8357 0.0345 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0818 -0.6042 -1.0167 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0640 0.2303 -0.2978 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2566 -1.5754 -0.4789 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6046 -2.7762 0.0858 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9809 -3.2335 1.0705 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7337 -3.5484 -0.4727 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4699 -3.9044 -1.9251 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8943 -4.8177 0.3244 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0703 3.0099 0.7955 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8165 3.2414 2.1379 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6879 3.7820 3.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8372 4.1024 2.6357 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3250 3.9932 4.4763 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 3.6650 -0.1097 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7209 2.6460 -0.9979 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3016 3.2466 -1.6836 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1974 3.4874 -3.0543 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8416 3.1533 -3.6752 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3229 4.1374 -3.7562 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2386 1.3090 2.2227 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4652 -2.4246 1.8123 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9654 -3.8968 0.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9225 -3.5337 1.8470 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3640 -3.0285 -1.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3617 -2.0528 -1.5656 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9551 -2.1233 -0.5181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6334 -1.4432 0.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4056 -0.1779 -2.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0318 -1.2981 -2.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7786 0.5077 -2.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3996 1.6783 -1.3698 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9483 0.3734 0.8705 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2067 0.0916 -0.9561 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2878 1.6835 -0.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2609 3.0489 0.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5175 1.8066 1.5980 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3114 3.1453 1.3889 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6421 0.5819 0.8952 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7402 -1.3480 0.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7480 -1.5792 -1.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5105 -0.0987 -1.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0909 -0.2406 0.7721 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6443 -2.9146 -0.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9187 -3.1128 -2.5570 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8774 -4.9068 -2.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 -3.9080 -2.0478 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9403 -5.3826 0.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7574 -5.4188 0.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0099 -4.5438 1.4107 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1180 3.3521 0.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4183 4.6207 4.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1505 4.5263 4.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1538 3.0504 5.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6078 2.3770 -1.6057 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0980 5.2103 -3.9158 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3968 3.6586 -4.7647 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2451 3.9770 -3.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9292 1.5067 2.9078 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2393 -1.4076 2.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5088 -3.0115 1.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1931 -2.9053 2.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 6 5 1 1 6 7 1 0 6 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 21 23 1 0 13 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 24 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 11 35 1 0 3 36 1 0 17 6 1 0 17 12 1 0 30 12 1 0 1 37 1 0 1 38 1 0 2 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 8 46 1 6 9 47 1 0 9 48 1 0 9 49 1 0 10 50 1 0 10 51 1 0 11 52 1 1 14 53 1 0 15 54 1 1 16 55 1 0 16 56 1 0 17 57 1 1 21 58 1 0 22 59 1 0 22 60 1 0 22 61 1 0 23 62 1 0 23 63 1 0 23 64 1 0 24 65 1 6 28 66 1 0 28 67 1 0 28 68 1 0 30 69 1 6 34 70 1 0 34 71 1 0 34 72 1 0 35 73 1 0 36 74 1 0 36 75 1 0 36 76 1 0 M END

Standard InCHIKey	PASSAFHUDJPXAL-JXHLGRMOSA-N
Standard InCHI	InChI=1S/C28H40O8/c1-9-16(4)10-11-27(8)17(5)12-23(31)28-21(13-20(14-22(27)28)35-24(32)15(2)3)25(33-18(6)29)36-26(28)34-19(7)30/h9-10,13,15,17,20,22-23,25-26,31H,1,11-12,14H2,2-8H3/b16-10+/t17-,20-,22+,23+,25+,26-,27-,28+/m1/s1
SMILES	C=C/C(=C/C[C@]1(C)[C@H](C)C[C@@H]([C@]23C(=C[C@H](C[C@@H]12)OC(=O)C(C)C)[C@@H](OC(=O)C)O[C@H]3OC(=O)C)O)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.27	Volume:	521.678 ? Van der Waals volume.
Dense:	0.967	LogP:	3.151 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.235 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.192 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	20.0
TPSA:	108.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.238	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.751	Fsp³:	0.679
MCE-18:	92.489 ? 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:	0.689	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.329	Promiscuous compounds:	0.406

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.044	MDCK Permeability:	-4.822
Pgp-inhibitor:	0.932	Pgp-substrate:	0.755
PAMPA:	0.184 ? 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):	0.006
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.994
Plasma Protein Binding (PPB):	67.355%	Volume Distribution (VD):	-0.21
Fu:	31.314% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.783	BCRP inhibitor:	0.469
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.117	CYP1A2-substrate:	0.397
CYP2C19-inhibitor:	0.01	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.981	CYP3A4-substrate:	0.219
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.974
HLM stability:	0.929 ? 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):

6.875

Half-life (T1/2):

0.981

ADMET: Toxicity

hERG Blockers:	0.077	hERG Blockers (10um):	0.335
Human Hepatotoxicity (H-HT):	0.647	Drug-induced Liver Injury (DILI):	0.866
AMES Toxicity:	0.867	Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.96	Skin Sensitization:	0.969
Carcinogencity:	0.555	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.64
Drug-induced Neurotoxicity:	0.793	Ototoxicity:	0.65
Hematotoxicity:	0.67	Drug-induced Nephrotoxicity:	0.91
Genotoxicity:	0.98	RPMI-8226 Immunitoxicity:	0.263
A549 Cytotoxicity:	0.686	Hek293 Cytotoxicity:	0.464
BCF:	0.864 ? 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:	3.839 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.656 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.157 ? 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
NPO18349	Casearia sylvestris	Species	Salicaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[11858737]
NPO18349	Casearia sylvestris	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18349	Casearia sylvestris	Species	Salicaceae	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
EC50	1
IZ	1
IC50	3

Activity Type	# Activity
Cell line	4
Organism	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
NPT91	Cell line	KB	Homo sapiens	EC50	=	1.4	ug.mL-1	PMID[11858737]
NPT4486	Cell line	LX-1	Homo sapiens	IC50	=	540.0	nM	PMID[11858737]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	710.0	nM	PMID[11858737]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	820.0	nM	PMID[11858737]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	348.0	mm2	PMID[11858737]

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 NPC329623 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	19127
0.1-0.2	26903
0.2-0.3	3679
0.3-0.4	46
0.4-0.5	35
0.5-0.6	26
0.6-0.7	12
0.7-0.8	0
0.8-0.85	6
0.85-0.9	9
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9322	High Similarity	NPC488660
0.9322	High Similarity	NPC488657
0.9167	High Similarity	NPC330003
0.9167	High Similarity	NPC470321
0.9167	High Similarity	NPC264867
0.9167	High Similarity	NPC473207
0.9138	High Similarity	NPC602188
0.8689	High Similarity	NPC201880
0.8689	High Similarity	NPC81567
0.8689	High Similarity	NPC488652
0.8689	High Similarity	NPC609711
0.8667	High Similarity	NPC488656
0.8548	High Similarity	NPC488658
0.8548	High Similarity	NPC488655
0.85	High Similarity	NPC488659
0.85	High Similarity	NPC604149
0.8281	Intermediate Similarity	NPC488964
0.8281	Intermediate Similarity	NPC184512
0.8254	Intermediate Similarity	NPC609715
0.8095	Intermediate Similarity	NPC134270
0.8095	Intermediate Similarity	NPC488654
0.8095	Intermediate Similarity	NPC609880
0.7727	Intermediate Similarity	NPC252296
0.75	Intermediate Similarity	NPC488653
0.7273	Intermediate Similarity	NPC479491
0.726	Intermediate Similarity	NPC109376
0.7164	Intermediate Similarity	NPC475889
0.7164	Intermediate Similarity	NPC7613
0.7164	Intermediate Similarity	NPC479942
0.6986	Remote Similarity	NPC116292
0.697	Remote Similarity	NPC479943
0.6765	Remote Similarity	NPC479940
0.6765	Remote Similarity	NPC7644
0.6765	Remote Similarity	NPC316974
0.6765	Remote Similarity	NPC479497
0.6667	Remote Similarity	NPC238397
0.6571	Remote Similarity	NPC479941
0.6528	Remote Similarity	NPC127933
0.6522	Remote Similarity	NPC311223
0.6479	Remote Similarity	NPC471363
0.6087	Remote Similarity	NPC488235
0.597	Remote Similarity	NPC603601
0.5946	Remote Similarity	NPC119550
0.5942	Remote Similarity	NPC600724
0.5915	Remote Similarity	NPC473204
0.5797	Remote Similarity	NPC606965
0.5758	Remote Similarity	NPC604446
0.575	Remote Similarity	NPC486751
0.5732	Remote Similarity	NPC224660
0.5634	Remote Similarity	NPC88507
0.5581	Remote Similarity	NPC320734
0.5556	Remote Similarity	NPC316708
0.5541	Remote Similarity	NPC217921
0.5541	Remote Similarity	NPC135015
0.55	Remote Similarity	NPC473399
0.55	Remote Similarity	NPC87630
0.5405	Remote Similarity	NPC311166
0.5405	Remote Similarity	NPC128795
0.5333	Remote Similarity	NPC88013
0.5256	Remote Similarity	NPC40728
0.5211	Remote Similarity	NPC98112
0.5132	Remote Similarity	NPC218158
0.5128	Remote Similarity	NPC125423
0.5122	Remote Similarity	NPC179128
0.5122	Remote Similarity	NPC473216
0.506	Remote Similarity	NPC162569
0.506	Remote Similarity	NPC35160

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7071
0.1-0.2	2051
0.2-0.3	28
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