NPASS Compound

Natural Product: NPC222845

Natural Product ID	NPC222845
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Alpha,16Alpha-Dihydroxylanosta-7,9(11),24-Trien-21-Oic Acid
IUPAC Name	(2R)-2-[(3R,5R,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL496839
PubChem CID	16083192
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 80 83 0 0 0 0 0 0 0 0999 V2000 8.9342 -1.3604 -0.3494 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7344 -0.9153 0.3823 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9609 0.0326 -0.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7341 0.4795 0.6595 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5445 0.2441 -0.1956 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2162 0.6526 0.4563 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1222 0.3045 -0.5356 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2290 -1.2146 -0.7410 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7577 -1.5377 -1.9651 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8179 -1.7352 -0.5366 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0122 -0.5660 -0.8850 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7391 0.5846 -0.1582 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3767 0.5657 1.2848 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1463 1.8257 -0.7965 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3078 1.8400 -0.5021 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0191 0.7616 -0.2861 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3684 -0.5600 -0.3307 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9876 -1.6465 0.1081 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3797 -1.4967 0.6523 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0523 -0.4981 -0.2519 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4756 0.8586 0.0062 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5749 1.3100 1.4391 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1613 1.8410 -0.8992 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6114 1.9052 -0.5004 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2594 0.5976 -0.7313 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5360 -0.5997 -0.2294 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9124 -1.7453 -1.1936 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1025 -1.0589 1.0996 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5495 0.4830 -2.1093 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0794 -0.3165 -2.3627 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2697 2.0780 0.7538 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1713 2.8035 0.2854 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3422 2.7061 1.5623 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3906 -1.5444 1.6851 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6674 -1.7569 -1.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4302 -2.2094 0.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6759 -0.5227 -0.4490 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1687 0.5227 -1.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8510 1.5160 0.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6575 -0.1569 1.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6843 0.8573 -1.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5280 -0.8045 -0.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1254 -0.0053 1.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4253 0.8213 -1.4868 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8369 -1.6987 0.0514 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3450 -2.3297 -1.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6735 -2.0404 0.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6593 -2.5571 -1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2186 0.2408 1.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1093 1.5227 1.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4393 -0.1972 1.5009 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3016 1.8002 -1.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5736 2.7679 -0.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7998 2.7984 -0.4650 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5207 -2.5952 0.0791 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8636 -2.4997 0.5607 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3828 -1.2313 1.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7163 -0.7638 -1.3010 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5759 1.4167 1.8383 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8816 0.7074 2.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1185 2.3446 1.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7758 2.8583 -0.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1419 1.4165 -1.9371 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0852 2.6404 -1.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7793 2.3554 0.4945 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2734 0.6232 -0.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0120 -1.8446 -1.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4425 -2.6942 -0.8424 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6527 -1.4906 -2.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3113 -0.2274 1.7957 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5288 -1.8746 1.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1236 -1.4849 0.8687 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2679 1.1074 -2.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3204 -1.3002 -2.8385 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9446 0.3373 -2.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8596 0.0545 -2.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3720 3.6983 1.7945 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1347 -2.3158 1.9815 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4321 -2.0835 1.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3487 -0.8017 2.5131 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 8 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 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 11 30 1 6 6 31 1 0 31 32 2 0 31 33 1 0 2 34 1 0 12 7 1 0 21 16 1 0 17 11 1 0 26 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 1 7 44 1 6 8 45 1 1 9 46 1 0 10 47 1 0 10 48 1 0 13 49 1 0 13 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 18 55 1 0 19 56 1 0 19 57 1 0 20 58 1 6 22 59 1 0 22 60 1 0 22 61 1 0 23 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 25 66 1 1 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	XSLKAKROJKMHIT-HBZKPHNJSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-18(2)9-8-10-19(26(33)34)25-22(31)17-30(7)21-11-12-23-27(3,4)24(32)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,13,19,22-25,31-32H,8,10,12,14-17H2,1-7H3,(H,33,34)/t19-,22-,23+,24-,25+,28-,29-,30+/m1/s1
SMILES	CC(=CCC[C@H]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	517.825 ? Van der Waals volume.
Dense:	0.908	LogP:	4.359 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.477 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.242 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.413	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.068	Fsp³:	0.767
MCE-18:	82.189 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.803	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.098 ? 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:	0.393	Promiscuous compounds:	0.142

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.499	MDCK Permeability:	-5.054
Pgp-inhibitor:	0.0	Pgp-substrate:	0.485
PAMPA:	1.0 ? 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%):	0.068	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416	MRP1:	0.996
Plasma Protein Binding (PPB):	88.349%	Volume Distribution (VD):	-0.319
Fu:	9.234% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.946	BCRP inhibitor:	0.008
BSEP inhibitor:	0.231

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.97	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.538
HLM stability:	0.017 ? 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):

7.506

Half-life (T1/2):

0.929

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.145
Human Hepatotoxicity (H-HT):	0.51	Drug-induced Liver Injury (DILI):	0.172
AMES Toxicity:	0.261	Rat Oral Acute Toxicity:	0.401
Maximum Recommended Daily Dose:	0.195	Skin Sensitization:	0.982
Carcinogencity:	0.543	Eye Corrosion:	0.011
Eye Irritation:	0.417	Respiratory Toxicity:	0.717
Drug-induced Neurotoxicity:	0.124	Ototoxicity:	0.667
Hematotoxicity:	0.342	Drug-induced Nephrotoxicity:	0.725
Genotoxicity:	0.391	RPMI-8226 Immunitoxicity:	0.099
A549 Cytotoxicity:	0.243	Hek293 Cytotoxicity:	0.13
BCF:	1.237 ? 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:	3.919 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.552 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.833 ? 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
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)91122-1]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[16933889]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27996259]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	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
Activity	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
NPT168	Cell line	P388	Mus musculus	Activity	>	125.0	ug ml-1	PMID[20368407]

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 NPC222845 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	18290
0.1-0.2	27253
0.2-0.3	3877
0.3-0.4	348
0.4-0.5	31
0.5-0.6	30
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC296577
0.8833	High Similarity	NPC48647
0.8065	Intermediate Similarity	NPC45324
0.8065	Intermediate Similarity	NPC162001
0.7937	Intermediate Similarity	NPC484975
0.7937	Intermediate Similarity	NPC186810
0.7937	Intermediate Similarity	NPC321301
0.746	Intermediate Similarity	NPC84271
0.746	Intermediate Similarity	NPC102414
0.7231	Intermediate Similarity	NPC66429
0.6765	Remote Similarity	NPC484967
0.6667	Remote Similarity	NPC76895
0.6618	Remote Similarity	NPC469406
0.6522	Remote Similarity	NPC484968
0.6418	Remote Similarity	NPC247406
0.625	Remote Similarity	NPC484969
0.6232	Remote Similarity	NPC470375
0.6232	Remote Similarity	NPC470376
0.6027	Remote Similarity	NPC288464
0.6027	Remote Similarity	NPC477813
0.6027	Remote Similarity	NPC607198
0.6	Remote Similarity	NPC77168
0.5915	Remote Similarity	NPC477812
0.589	Remote Similarity	NPC263347
0.5857	Remote Similarity	NPC212948
0.5846	Remote Similarity	NPC205455
0.5833	Remote Similarity	NPC152897
0.5753	Remote Similarity	NPC155676
0.5753	Remote Similarity	NPC141401
0.5694	Remote Similarity	NPC214697
0.5556	Remote Similarity	NPC203035
0.5405	Remote Similarity	NPC123854
0.5362	Remote Similarity	NPC231310
0.5352	Remote Similarity	NPC233836
0.5352	Remote Similarity	NPC159046
0.5352	Remote Similarity	NPC187376
0.5333	Remote Similarity	NPC7165
0.527	Remote Similarity	NPC608955
0.5224	Remote Similarity	NPC72507
0.5211	Remote Similarity	NPC475772
0.5205	Remote Similarity	NPC48866
0.5143	Remote Similarity	NPC202389
0.5139	Remote Similarity	NPC484974
0.5139	Remote Similarity	NPC23434
0.5135	Remote Similarity	NPC45269
0.5135	Remote Similarity	NPC138536
0.5128	Remote Similarity	NPC469432
0.5072	Remote Similarity	NPC6707
0.5072	Remote Similarity	NPC147568
0.5068	Remote Similarity	NPC173272
0.5067	Remote Similarity	NPC482518
0.5065	Remote Similarity	NPC489791

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC222845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6082
0.1-0.2	2992
0.2-0.3	74
0.3-0.4	2
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