NPASS Compound

Natural Product: NPC92022

Natural Product ID	NPC92022
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RDQLYDRUPXDRSE-YZQFCQQCSA-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 89 92 0 0 0 0 0 0 0 0999 V2000 5.4382 2.5648 -1.3132 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4960 1.5355 -1.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0560 0.3020 -0.8577 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5842 -0.0506 -0.9306 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1669 -0.6160 0.3581 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7733 -1.0574 0.5884 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7611 -1.5814 2.0332 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6632 -0.1835 0.2477 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6235 0.1568 -1.2186 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1494 -0.0627 -1.6645 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5423 0.2528 -0.4041 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4944 1.7332 -0.1275 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9434 -0.1590 -0.2777 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7076 -0.6345 -1.2368 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1170 -0.9908 -0.8732 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6537 0.0838 0.0162 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1525 0.0672 0.1515 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7876 0.8646 -0.9922 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7340 -1.3159 0.1776 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4982 0.7891 1.4021 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4931 0.4973 2.0065 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6051 1.8593 1.8813 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2352 1.2977 2.1338 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9533 0.0413 1.3573 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3234 -1.1837 2.1486 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5010 -0.0072 1.0855 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6369 0.0851 2.0584 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1761 0.0537 1.9351 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2847 -0.5401 0.6269 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1201 -1.9568 0.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1139 0.8450 -2.7237 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4045 0.3989 -3.9916 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4324 -0.8410 -4.1995 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6918 1.2814 -5.1497 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0318 -1.7019 0.7006 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8856 -1.6071 1.7844 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9464 -0.5780 2.5150 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7650 -2.7573 2.1030 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9028 1.8917 -0.9682 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2396 3.0807 -1.1472 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8817 0.9560 -0.7128 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7520 2.5391 -0.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9443 3.5667 -1.2447 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9438 2.4143 -2.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7605 -0.5049 -0.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5513 -0.8413 -1.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1006 0.8236 -1.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3951 0.1751 1.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6528 -2.0165 -0.0090 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8353 -2.1353 2.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0311 -0.8157 2.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5661 -2.3639 2.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8596 0.8005 0.7892 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2101 -0.5191 -1.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7772 1.2383 -1.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0383 -1.0801 -2.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4870 2.1333 0.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2895 2.0254 0.5886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8010 2.2296 -1.0962 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3217 -0.7548 -2.2178 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7392 -1.1153 -1.7826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0676 -1.9908 -0.3984 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3807 1.0646 -0.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8339 1.0586 -0.6699 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7621 0.3136 -1.9384 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2628 1.8351 -1.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2655 -1.4995 -0.7976 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4389 -1.3961 1.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9891 -2.1118 0.2759 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0087 2.3325 2.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5755 2.6709 1.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5028 2.0756 1.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1018 1.1599 3.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7414 -1.1365 3.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0072 -2.0977 1.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3916 -1.2272 2.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0497 0.1980 3.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1737 1.1194 1.9339 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2521 -0.4186 2.8178 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6766 -2.4924 -0.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0364 -2.0765 -0.1705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3740 -2.4752 1.4073 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2779 2.2898 -5.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1872 0.8133 -6.0415 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7812 1.2766 -5.4098 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7054 -2.3434 2.5424 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0345 -3.3537 1.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2270 -3.3813 2.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8815 1.1812 -0.7421 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 1 10 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 5 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 2 39 1 0 39 40 2 0 39 41 1 0 29 8 1 0 29 11 1 0 26 13 1 0 24 16 1 0 1 42 1 0 1 43 1 0 1 44 1 0 3 45 1 0 4 46 1 0 4 47 1 0 5 48 1 1 6 49 1 6 7 50 1 0 7 51 1 0 7 52 1 0 8 53 1 1 9 54 1 0 9 55 1 0 10 56 1 6 12 57 1 0 12 58 1 0 12 59 1 0 14 60 1 0 15 61 1 0 15 62 1 0 16 63 1 6 18 64 1 0 18 65 1 0 18 66 1 0 19 67 1 0 19 68 1 0 19 69 1 0 22 70 1 0 22 71 1 0 23 72 1 0 23 73 1 0 25 74 1 0 25 75 1 0 25 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 34 83 1 0 34 84 1 0 34 85 1 0 38 86 1 0 38 87 1 0 38 88 1 0 41 89 1 0 M END

Standard InCHIKey	RDQLYDRUPXDRSE-YZQFCQQCSA-N
Standard InCHI	InChI=1S/C34H48O7/c1-19(30(38)39)10-12-26(40-21(3)35)20(2)25-18-29(41-22(4)36)34(9)24-11-13-27-31(5,6)28(37)15-16-32(27,7)23(24)14-17-33(25,34)8/h10-11,14,20,25-27,29H,12-13,15-18H2,1-9H3,(H,38,39)/b19-10+/t20-,25+,26-,27-,29-,32+,33+,34+/m0/s1
SMILES	C/C(=CC[C@@H]([C@@H](C)[C@H]1C[C@@H]([C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C)OC(=O)C)OC(=O)C)/C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.34	Volume:	605.47 ? Van der Waals volume.
Dense:	0.939	LogP:	3.096 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.816 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.454 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	25.0
TPSA:	106.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.272	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.318	Fsp³:	0.706
MCE-18:	86.897 ? 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:	0.91	Fluc inhibitor:	0.032 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.081 ? 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:	0.434	Promiscuous compounds:	0.374

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.298	MDCK Permeability:	-5.033
Pgp-inhibitor:	0.995	Pgp-substrate:	0.001
PAMPA:	0.772 ? 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):	0.004
20% Bioavailability (F20%):	0.454	30% Bioavailability (F30%):	0.802
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.993
Plasma Protein Binding (PPB):	82.811%	Volume Distribution (VD):	-0.254
Fu:	17.219% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.012
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.057	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.016	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.867
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.987 ? 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):

4.178

Half-life (T1/2):

0.618

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.039
Human Hepatotoxicity (H-HT):	0.735	Drug-induced Liver Injury (DILI):	0.91
AMES Toxicity:	0.157	Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.441	Skin Sensitization:	0.962
Carcinogencity:	0.521	Eye Corrosion:	0.002
Eye Irritation:	0.038	Respiratory Toxicity:	0.319
Drug-induced Neurotoxicity:	0.25	Ototoxicity:	0.8
Hematotoxicity:	0.686	Drug-induced Nephrotoxicity:	0.862
Genotoxicity:	0.968	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.092	Hek293 Cytotoxicity:	0.081
BCF:	0.5 ? 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:	3.466 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.294 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.52 ? 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
NPO40519	Ganoderma orbiforme BCC 22325	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40520	Ganoderma sp. BCC 60695	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40518	Ganoderma australe BCC 22314	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]

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
MIC	1
IC50	1

Activity Type	# Activity
Cell line	1
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
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	87000.0	nM	PMID[28504879]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	25.0	ug.mL-1	PMID[28504879]

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 NPC92022 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	23049
0.1-0.2	23605
0.2-0.3	2951
0.3-0.4	174
0.4-0.5	44
0.5-0.6	21
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
0.7857	Intermediate Similarity	NPC85742
0.7857	Intermediate Similarity	NPC22421
0.7778	Intermediate Similarity	NPC137552
0.7778	Intermediate Similarity	NPC99411
0.7746	Intermediate Similarity	NPC58410
0.7606	Intermediate Similarity	NPC478312
0.7105	Intermediate Similarity	NPC166120
0.7067	Intermediate Similarity	NPC478299
0.6795	Remote Similarity	NPC489805
0.6625	Remote Similarity	NPC478310
0.6104	Remote Similarity	NPC276127
0.6104	Remote Similarity	NPC478307
0.6026	Remote Similarity	NPC136044
0.5949	Remote Similarity	NPC39082
0.5949	Remote Similarity	NPC610107
0.5897	Remote Similarity	NPC141401
0.5897	Remote Similarity	NPC69982
0.5823	Remote Similarity	NPC489791
0.575	Remote Similarity	NPC478297
0.5732	Remote Similarity	NPC478311
0.5625	Remote Similarity	NPC478300
0.5556	Remote Similarity	NPC478301
0.5476	Remote Similarity	NPC478309
0.5422	Remote Similarity	NPC478305
0.5422	Remote Similarity	NPC52776
0.5412	Remote Similarity	NPC76162
0.5385	Remote Similarity	NPC87552
0.5366	Remote Similarity	NPC489802
0.5357	Remote Similarity	NPC610168
0.5294	Remote Similarity	NPC478304
0.5294	Remote Similarity	NPC231673
0.506	Remote Similarity	NPC285702
0.506	Remote Similarity	NPC166745
0.506	Remote Similarity	NPC235464

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC92022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6585
0.1-0.2	2505
0.2-0.3	60
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