NPASS Compound

Natural Product: NPC484801

Natural Product ID	NPC484801
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FPBISNWLDZZHDD-BPOUPGCLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	134147841
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001460] Vitamin D and derivatives

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 8.0292 -0.3458 -1.1601 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6382 -0.4117 0.2784 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4172 -0.1039 0.6975 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3435 0.3268 -0.2026 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3527 1.2533 0.4226 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0994 0.4246 0.6977 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9457 0.9233 -0.1637 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7425 2.4227 0.0224 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2500 2.6814 0.0831 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2581 1.3982 -0.5216 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1221 1.4734 -1.9581 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6621 1.0917 -0.3216 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5588 1.9067 -0.8483 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0187 1.7754 -0.7614 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4009 0.4572 -0.1554 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8029 0.0407 -0.5147 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9793 -0.3541 -1.9432 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6876 1.2751 -0.2838 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2447 -1.0846 0.3593 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1269 -1.5545 1.2379 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8530 -1.8338 0.4429 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3850 -0.6121 -0.3152 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0406 -0.9727 -1.7154 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1426 -0.0911 0.4405 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1811 -1.2018 0.5291 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2274 -0.9391 0.1178 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5933 0.4577 0.3069 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5023 0.8025 1.7613 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2724 -0.6357 1.1954 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5583 -0.9428 0.2459 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0802 -1.7092 1.2564 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6418 -2.9974 1.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6272 -0.7444 -0.6652 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6916 -0.8432 1.2380 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5365 0.6109 -1.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1730 -0.5520 -1.8346 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7637 -1.1551 -1.3490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2170 -0.1786 1.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8374 0.8006 -1.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1618 2.0827 -0.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7521 1.6764 1.3777 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8919 0.4123 1.7619 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1696 0.6046 -1.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2126 2.9883 -0.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1953 2.8313 0.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1246 2.9052 1.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0302 3.5585 -0.5694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8061 1.8210 -2.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4442 0.4962 -2.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8358 2.2828 -2.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2252 2.8091 -1.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4011 2.6402 -0.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5057 1.8051 -1.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4501 0.6639 0.9602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5580 -1.3524 -2.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6920 0.4274 -2.6767 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0933 -0.4794 -2.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7257 0.9604 -0.1694 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3055 1.8711 0.5791 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5753 1.8932 -1.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6809 -1.9199 -0.2320 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9538 -0.9363 2.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4389 -2.5670 1.6308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1181 -2.1988 1.1832 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0829 -2.6807 -0.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2857 -2.0603 -1.8987 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9144 -0.9467 -1.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4172 -0.3094 -2.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5922 0.2107 1.4315 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2227 -1.5754 1.5961 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5090 -2.1096 -0.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 -1.5572 0.8370 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4768 -1.3246 -0.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7247 -0.1365 2.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2398 1.5393 2.1253 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 1.1716 2.0811 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9770 0.1833 1.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8093 -1.4722 -0.3995 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5495 -3.0940 1.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0059 -3.6623 0.5409 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1063 -3.4197 2.2920 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1679 -1.7548 0.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5190 -0.0846 1.2993 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2837 -1.0875 2.2297 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 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 0 10 11 1 6 10 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 16 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 19 29 1 0 6 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 2 34 1 0 33 4 1 0 27 7 1 0 27 10 1 0 24 12 1 0 22 15 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 6 42 1 1 7 43 1 6 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 11 48 1 0 11 49 1 0 11 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 1 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 18 60 1 0 19 61 1 6 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 1 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 28 74 1 0 28 75 1 0 28 76 1 0 29 77 1 0 30 78 1 0 32 79 1 0 32 80 1 0 32 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 M END

Standard InCHIKey	FPBISNWLDZZHDD-BPOUPGCLSA-N
Standard InCHI	InChI=1S/C31H50O3/c1-19(2)17-20-18-21(27(33-8)34-20)22-11-15-31(7)24-9-10-25-28(3,4)26(32)13-14-29(25,5)23(24)12-16-30(22,31)6/h9,17,20-23,25-27,32H,10-16,18H2,1-8H3/t20?,21-,22-,23-,25-,26+,27?,29+,30-,31+/m0/s1
SMILES	CC(=CC1C[C@@H]([C@@H]2CC[C@]3(C)C4=CC[C@H]5C(C)(C)[C@@H](CC[C@]5(C)[C@H]4CC[C@@]23C)O)C(OC)O1)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.38	Volume:	523.047 ? Van der Waals volume.
Dense:	0.899	LogP:	5.748 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.407 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.005 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	26.0
TPSA:	38.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.44	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.099	Fsp³:	0.871
MCE-18:	95.586 ? 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:	0.894	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.235	Promiscuous compounds:	0.098

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.181	MDCK Permeability:	-4.863
Pgp-inhibitor:	0.626	Pgp-substrate:	0.591
PAMPA:	0.802 ? 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%):	0.495	30% Bioavailability (F30%):	0.182
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.853	MRP1:	0.936
Plasma Protein Binding (PPB):	93.867%	Volume Distribution (VD):	0.066
Fu:	5.994% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.759
BSEP inhibitor:	0.907

ADMET: Metabolism

CYP1A2-inhibitor:	0.613	CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.215
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.937
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.654
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.948
HLM stability:	0.998 ? 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):

14.559

Half-life (T1/2):

0.638

ADMET: Toxicity

hERG Blockers:	0.157	hERG Blockers (10um):	0.446
Human Hepatotoxicity (H-HT):	0.642	Drug-induced Liver Injury (DILI):	0.408
AMES Toxicity:	0.605	Rat Oral Acute Toxicity:	0.659
Maximum Recommended Daily Dose:	0.721	Skin Sensitization:	0.941
Carcinogencity:	0.783	Eye Corrosion:	0.002
Eye Irritation:	0.279	Respiratory Toxicity:	0.904
Drug-induced Neurotoxicity:	0.331	Ototoxicity:	0.563
Hematotoxicity:	0.395	Drug-induced Nephrotoxicity:	0.28
Genotoxicity:	0.679	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.477	Hek293 Cytotoxicity:	0.543
BCF:	2.81 ? 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:	4.627 ? 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:	5.441 ? 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
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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

Activity Type	# Activity
Non-molecular	3

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[27494664]

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 NPC484801 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	20666
0.1-0.2	24309
0.2-0.3	4273
0.3-0.4	487
0.4-0.5	78
0.5-0.6	22
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC484789
1.0	High Similarity	NPC484786
1.0	High Similarity	NPC484787
1.0	High Similarity	NPC484788
0.871	High Similarity	NPC484791
0.871	High Similarity	NPC484790
0.7969	Intermediate Similarity	NPC324598
0.7846	Intermediate Similarity	NPC5358
0.7846	Intermediate Similarity	NPC216260
0.746	Intermediate Similarity	NPC470049
0.6324	Remote Similarity	NPC486523
0.6176	Remote Similarity	NPC470077
0.6176	Remote Similarity	NPC125399
0.6176	Remote Similarity	NPC486522
0.6047	Remote Similarity	NPC250089
0.6047	Remote Similarity	NPC157530
0.6029	Remote Similarity	NPC470224
0.6	Remote Similarity	NPC63023
0.6	Remote Similarity	NPC121566
0.6	Remote Similarity	NPC100955
0.6	Remote Similarity	NPC95243
0.5972	Remote Similarity	NPC471293
0.597	Remote Similarity	NPC30166
0.5909	Remote Similarity	NPC14630
0.5844	Remote Similarity	NPC85593
0.5844	Remote Similarity	NPC31430
0.5714	Remote Similarity	NPC488572
0.5694	Remote Similarity	NPC210268
0.5694	Remote Similarity	NPC190604
0.5616	Remote Similarity	NPC472240
0.5616	Remote Similarity	NPC262858
0.5488	Remote Similarity	NPC101450
0.5429	Remote Similarity	NPC328052
0.5362	Remote Similarity	NPC1319
0.527	Remote Similarity	NPC142361
0.527	Remote Similarity	NPC474684
0.525	Remote Similarity	NPC189282
0.525	Remote Similarity	NPC237402
0.5205	Remote Similarity	NPC470047
0.5205	Remote Similarity	NPC470046
0.5132	Remote Similarity	NPC605437
0.5122	Remote Similarity	NPC609156
0.5053	Remote Similarity	NPC488573

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC484801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7596
0.1-0.2	1493
0.2-0.3	57
0.3-0.4	3
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