NPASS Compound

Natural Product: NPC324063

Natural Product ID	NPC324063
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1R,2R,4Ar,4Bs,6Ar,9R,10As,12Ar)-2-(1,2-Dihydroxypropan-2-Yl)-9-(Hydroxymethyl)-1-(3-Methoxy-3-Oxopropyl)-1,4A,4B,9-Tetramethyl-3,4,5,6,7,8,10,10A,12,12A-Decahydro-2H-Chrysene-6A-Carboxylic Acid
IUPAC Name	(1R,2R,4aR,4bS,6aR,9R,10aS,12aR)-2-(1,2-dihydroxypropan-2-yl)-9-(hydroxymethyl)-1-(3-methoxy-3-oxopropyl)-1,4a,4b,9-tetramethyl-3,4,5,6,7,8,10,10a,12,12a-decahydro-2H-chrysene-6a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1910834
PubChem CID	54671989
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003236] 17-hydroxysteroids

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 88 91 0 0 0 0 0 0 0 0999 V2000 -3.6631 -0.0332 -3.0504 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4007 -0.0219 -1.7131 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2876 -1.4008 -1.1281 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6465 -1.4507 0.3175 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0211 -0.3883 1.1731 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2843 -0.9419 2.3461 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9990 -0.2103 2.6439 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0714 -0.3958 1.4349 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7606 0.2771 0.3022 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0398 0.5854 -0.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4255 0.2454 -0.7416 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0321 0.7072 0.5483 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3014 0.2108 1.7486 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0221 -0.7017 2.6491 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3824 -1.1690 2.2829 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7698 -0.8873 0.8171 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5603 0.5345 0.6143 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0827 1.3482 1.8216 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1130 1.2854 -0.5327 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5766 1.4172 -0.6990 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7750 2.2485 -1.9596 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8093 2.6728 -2.6282 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0701 2.5337 -2.3634 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3864 3.2851 -3.4996 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9105 -1.6747 0.3594 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2228 -1.5647 1.0028 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5105 -3.1753 0.5419 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3118 -3.4465 -0.0605 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0058 -1.6063 -1.0354 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1054 1.4574 2.5645 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1847 0.5984 0.4122 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8620 1.0599 -0.8523 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0521 -1.8632 1.1927 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1725 0.4045 1.7471 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3652 0.1515 1.5159 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8409 1.4612 2.5697 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8750 0.2062 -2.0873 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0002 1.4292 -2.7643 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6724 -0.5108 -2.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6008 0.9966 -3.4849 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3134 -0.6091 -3.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3136 -1.8146 -1.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0566 -2.0280 -1.6678 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7392 -1.5283 0.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2496 -2.4364 0.7084 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1789 -2.0255 2.1924 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8804 -0.8638 3.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2672 0.8205 2.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5160 -0.7011 3.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 1.0592 -1.5872 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4873 -0.8038 -0.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7981 0.7944 -1.6281 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9527 1.8410 0.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0766 -0.3108 3.7132 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4046 -1.6405 2.8343 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1767 -0.8485 2.9829 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4492 -2.3012 2.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8917 -1.4192 0.2900 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1885 1.2774 1.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8126 2.4295 1.6249 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7145 1.0585 2.7726 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7553 2.3552 -0.3973 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6251 1.0057 -1.5197 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2364 0.6004 -0.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0292 2.1088 0.0946 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4856 3.4096 -4.1583 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7808 4.3092 -3.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2074 2.7752 -4.0443 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0296 -1.4280 0.2171 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5241 -2.5129 1.4942 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3233 -0.8018 1.7991 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6790 -3.5339 1.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2918 -3.7033 -0.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4189 -3.5367 -1.0401 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1538 -1.6876 -1.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4225 1.2068 3.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 1.9628 1.9363 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6719 2.2115 2.6284 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2141 1.5398 1.0628 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7814 1.6674 -0.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2436 1.8276 -1.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2574 -2.4886 2.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1568 -2.2967 0.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8804 -2.1754 0.4903 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4859 1.8953 3.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5380 0.1262 -1.2165 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2039 -0.5679 -2.8103 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4617 2.1079 -2.2109 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 16 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 25 29 1 0 13 30 1 0 9 31 1 0 31 32 1 0 8 33 1 0 5 34 1 0 34 35 2 0 34 36 1 0 2 37 1 0 37 38 1 0 32 2 1 0 31 5 1 0 13 8 1 0 17 12 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 6 46 1 0 6 47 1 0 7 48 1 0 7 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 18 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 24 66 1 0 24 67 1 0 24 68 1 0 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 33 82 1 0 33 83 1 0 33 84 1 0 36 85 1 0 37 86 1 0 37 87 1 0 38 88 1 0 M END

Standard InCHIKey	SUUYXWGSSHWCRR-RIFYGRPCSA-N
Standard InCHI	InChI=1S/C31H50O7/c1-26(18-32)13-15-31(25(35)36)16-14-28(3)20(21(31)17-26)7-8-22-27(2,11-10-24(34)38-6)23(30(5,37)19-33)9-12-29(22,28)4/h7,21-23,32-33,37H,8-19H2,1-6H3,(H,35,36)/t21-,22+,23+,26+,27+,28+,29+,30?,31-/m0/s1
SMILES	CC1(CCC2(CCC3(C(=CCC4C3(CCC(C4(C)CCC(=O)OC)C(C)(CO)O)C)C2C1)C)C(=O)O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.36	Volume:	564.128 ? Van der Waals volume.
Dense:	0.947	LogP:	2.607 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.649 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.78 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	23.0
TPSA:	124.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.275	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.123	Fsp³:	0.871
MCE-18:	91.862 ? 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:	0.011	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.287 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.316	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.125	MDCK Permeability:	-4.848
Pgp-inhibitor:	0.0	Pgp-substrate:	0.037
PAMPA:	0.961 ? 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):	0.014
20% Bioavailability (F20%):	0.031	30% Bioavailability (F30%):	0.075
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172	MRP1:	1.0
Plasma Protein Binding (PPB):	76.18%	Volume Distribution (VD):	-0.391
Fu:	22.956% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.008
OATP1B3 inhibitor:	0.199	BCRP inhibitor:	0.002
BSEP inhibitor:	0.451

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.589	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.983	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.573	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.397	CYP2C8-inhibitor:	0.021
HLM stability:	0.006 ? 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):

2.325

Half-life (T1/2):

1.538

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.034
Human Hepatotoxicity (H-HT):	0.396	Drug-induced Liver Injury (DILI):	0.005
AMES Toxicity:	0.064	Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.305	Skin Sensitization:	0.284
Carcinogencity:	0.389	Eye Corrosion:	0.0
Eye Irritation:	0.012	Respiratory Toxicity:	0.146
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.969
Hematotoxicity:	0.202	Drug-induced Nephrotoxicity:	0.516
Genotoxicity:	0.004	RPMI-8226 Immunitoxicity:	0.02
A549 Cytotoxicity:	0.001	Hek293 Cytotoxicity:	0.02
BCF:	0.583 ? 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:	3.854 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.742 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.372 ? 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
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21870831]
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	stem bark	Purchased from an herbal market at Kumsan, Chungnam, Korea	2009-AUG	PMID[21870831]
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	9400.0	nM	PMID[21870831]

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 NPC324063 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	17426
0.1-0.2	27933
0.2-0.3	3859
0.3-0.4	405
0.4-0.5	192
0.5-0.6	33
0.6-0.7	8
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
0.6479	Remote Similarity	NPC182797
0.6479	Remote Similarity	NPC52169
0.6479	Remote Similarity	NPC488562
0.625	Remote Similarity	NPC121798
0.625	Remote Similarity	NPC234346
0.6164	Remote Similarity	NPC472149
0.6164	Remote Similarity	NPC609452
0.6027	Remote Similarity	NPC156981
0.5946	Remote Similarity	NPC158141
0.5811	Remote Similarity	NPC275809
0.5811	Remote Similarity	NPC37038
0.5733	Remote Similarity	NPC481360
0.5658	Remote Similarity	NPC200752
0.5556	Remote Similarity	NPC188833
0.5467	Remote Similarity	NPC480946
0.5467	Remote Similarity	NPC130577
0.5467	Remote Similarity	NPC142415
0.5467	Remote Similarity	NPC102683
0.5455	Remote Similarity	NPC298554
0.5395	Remote Similarity	NPC270768
0.5395	Remote Similarity	NPC59263
0.5395	Remote Similarity	NPC210106
0.5395	Remote Similarity	NPC282616
0.5395	Remote Similarity	NPC480934
0.5375	Remote Similarity	NPC6255
0.5325	Remote Similarity	NPC106112
0.5325	Remote Similarity	NPC261935
0.5325	Remote Similarity	NPC231063
0.5325	Remote Similarity	NPC282395
0.5325	Remote Similarity	NPC110308
0.5256	Remote Similarity	NPC480932
0.5256	Remote Similarity	NPC120840
0.5195	Remote Similarity	NPC84319
0.5195	Remote Similarity	NPC52021
0.5195	Remote Similarity	NPC599947
0.5135	Remote Similarity	NPC604575
0.5128	Remote Similarity	NPC88116
0.5125	Remote Similarity	NPC148964
0.5063	Remote Similarity	NPC173089
0.5063	Remote Similarity	NPC104545
0.5062	Remote Similarity	NPC296164

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC324063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5290
0.1-0.2	3812
0.2-0.3	45
0.3-0.4	3
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