NPASS Compound

Natural Product: NPC532684

Natural Product ID	NPC532684
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},9~{R},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{S})-9-acetoxy-1-isopropenyl-5~{a},5~{b},8,8,11~{a}-pentamethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysene-3~{a}-carboxylic acid
IUPAC Name	(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},9~{R},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{S})-9-acetoxy-1-isopropenyl-5~{a},5~{b},8,8,11~{a}-pentamethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysene-3~{a}-carboxylic acid
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 86 90 0 0 0 0 0 0 0 0999 V2000 -4.2477 1.7899 -3.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9615 1.5675 -2.1064 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9749 2.5161 -1.5384 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5313 0.5273 -1.2787 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4357 1.1008 -0.1594 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8502 -0.0664 0.6495 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5963 -0.9298 0.6552 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0975 -2.3524 0.6256 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3193 -2.6473 0.6028 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2126 -3.4303 0.6220 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8967 -0.6897 1.9380 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4437 -1.1040 1.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7304 -0.3329 0.7818 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7945 1.0488 1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4273 -0.7832 -0.4240 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7049 -0.7850 -1.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2518 -0.5292 -1.7308 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3616 -0.1966 -0.4356 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8666 -0.3812 -0.5490 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3387 -1.7570 -0.7448 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3295 0.4210 -1.7829 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8220 0.3514 -1.9405 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5967 0.1510 -0.6831 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8390 0.8605 -0.7671 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0490 0.2519 -0.5901 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3663 0.9240 -0.6628 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0489 -0.9940 -0.3424 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8760 0.7050 0.5250 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1648 2.2148 0.5184 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5532 0.1896 1.7985 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4382 0.3913 0.6025 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9598 -0.2488 1.8659 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4554 0.0208 1.9382 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2554 -0.7221 0.7843 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1543 -2.1479 1.1256 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8580 -0.5507 -0.6165 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9614 1.1625 -3.9290 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7609 2.6095 -3.8942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2699 2.7754 -0.5007 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9515 2.0969 -1.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9616 3.4901 -2.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3735 0.1226 -1.9603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9334 1.8369 0.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3391 1.5892 -0.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1039 0.2230 1.6779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7089 -0.6222 0.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4293 -4.2326 0.0101 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3761 -1.4022 2.6853 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0914 0.2905 2.4168 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4834 -2.1710 1.5625 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9701 -0.9584 2.8845 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4631 1.0253 2.3682 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2141 1.8143 0.7501 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8102 1.4762 1.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3873 -1.9348 -0.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2672 -0.1207 -2.4316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8275 -1.7623 -2.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3706 -1.3554 -2.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0672 0.3230 -2.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2701 0.9375 -0.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5353 -2.5135 -0.9957 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0317 -1.8795 -1.6366 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9202 -2.1997 0.0926 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9315 1.4372 -1.7480 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9067 -0.1086 -2.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1428 -0.3855 -2.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1407 1.3493 -2.3648 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8610 -0.8857 -0.4607 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7819 0.9982 0.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0598 0.2037 -1.1885 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3597 1.8728 -1.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9720 2.4821 -0.1580 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2977 2.6088 1.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2247 2.6865 0.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6463 0.3032 1.6303 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2358 -0.8143 2.0707 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3137 0.9653 2.5842 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8996 1.3931 0.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3800 0.3428 2.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2492 -1.2724 2.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0413 -0.2343 2.9098 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4214 1.1208 1.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8776 -2.5329 1.2902 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7451 -2.8124 0.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5689 -2.2529 2.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1283 -1.4685 -1.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 8 9 2 0 8 10 1 0 7 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 2 0 23 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 1 15 36 1 0 36 4 1 0 36 7 1 0 34 13 1 0 34 18 1 0 31 19 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 6 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 14 52 1 0 14 53 1 0 14 54 1 0 15 55 1 1 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 1 20 61 1 0 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 23 68 1 1 26 69 1 0 26 70 1 0 26 71 1 0 29 72 1 0 29 73 1 0 29 74 1 0 30 75 1 0 30 76 1 0 30 77 1 0 31 78 1 6 32 79 1 0 32 80 1 0 33 81 1 0 33 82 1 0 35 83 1 0 35 84 1 0 35 85 1 0 36 86 1 6 M END

Standard InCHIKey	ACWNTJJUZAIOLW-UHYWUVHCSA-N
Standard InCHI	InChI=1S/C32H50O4/c1-19(2)21-11-16-32(27(34)35)18-17-30(7)22(26(21)32)9-10-24-29(6)14-13-25(36-20(3)33)28(4,5)23(29)12-15-31(24,30)8/h21-26H,1,9-18H2,2-8H3,(H,34,35)/t21-,22+,23-,24+,25+,26-,29-,30+,31+,32-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](OC(C)=O)C(C)(C)[C@@H]5CC[C@]43C)[C@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.37	Volume:	546.497 ? Van der Waals volume.
Dense:	0.912	LogP:	3.286 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.09 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.283 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	28.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.32	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.725	Fsp³:	0.875
MCE-18:	105.3 ? 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:	0.972	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.42	Promiscuous compounds:	0.27

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.281	MDCK Permeability:	-4.984
Pgp-inhibitor:	0.286	Pgp-substrate:	0.0
PAMPA:	0.249 ? 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%):	0.375	30% Bioavailability (F30%):	0.254
50% Bioavailability (F50%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108	MRP1:	0.93
Plasma Protein Binding (PPB):	97.508%	Volume Distribution (VD):	-0.292
Fu:	2.474% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.669	BCRP inhibitor:	0.007
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.696	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.052	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.298
HLM stability:	0.01 ? 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):

3.575

Half-life (T1/2):

0.763

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.05
Human Hepatotoxicity (H-HT):	0.542	Drug-induced Liver Injury (DILI):	0.685
AMES Toxicity:	0.225	Rat Oral Acute Toxicity:	0.305
Maximum Recommended Daily Dose:	0.185	Skin Sensitization:	0.959
Carcinogencity:	0.852	Eye Corrosion:	0.481
Eye Irritation:	0.758	Respiratory Toxicity:	0.732
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.446
Hematotoxicity:	0.665	Drug-induced Nephrotoxicity:	0.799
Genotoxicity:	0.629	RPMI-8226 Immunitoxicity:	0.019
A549 Cytotoxicity:	0.102	Hek293 Cytotoxicity:	0.136
BCF:	1.202 ? 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:	3.944 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.46 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.952 ? 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
NPO16051	Beilschmiedia erythrophloia	Species	Lauraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19072217]
NPO16051	Beilschmiedia erythrophloia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16051	Beilschmiedia erythrophloia	Species	Lauraceae	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

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

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 NPC532684 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	22363
0.1-0.2	22973
0.2-0.3	3842
0.3-0.4	515
0.4-0.5	81
0.5-0.6	54
0.6-0.7	18
0.7-0.8	0
0.8-0.85	0
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	NPC4309
0.8983	High Similarity	NPC160506
0.7302	Intermediate Similarity	NPC271974
0.7302	Intermediate Similarity	NPC247312
0.7143	Intermediate Similarity	NPC31031
0.6883	Remote Similarity	NPC248287
0.6883	Remote Similarity	NPC234548
0.6866	Remote Similarity	NPC478841
0.6866	Remote Similarity	NPC488166
0.6709	Remote Similarity	NPC8102
0.6709	Remote Similarity	NPC66894
0.6613	Remote Similarity	NPC68828
0.6562	Remote Similarity	NPC192744
0.6515	Remote Similarity	NPC201655
0.6462	Remote Similarity	NPC264317
0.6462	Remote Similarity	NPC294438
0.631	Remote Similarity	NPC205392
0.631	Remote Similarity	NPC105942
0.6286	Remote Similarity	NPC600907
0.6119	Remote Similarity	NPC488164
0.6119	Remote Similarity	NPC264005
0.6094	Remote Similarity	NPC305835
0.6094	Remote Similarity	NPC246445
0.5882	Remote Similarity	NPC488506
0.5882	Remote Similarity	NPC220498
0.5821	Remote Similarity	NPC119743
0.5821	Remote Similarity	NPC98270
0.5783	Remote Similarity	NPC475138
0.5775	Remote Similarity	NPC486704
0.5775	Remote Similarity	NPC474728
0.5735	Remote Similarity	NPC5280
0.5714	Remote Similarity	NPC16377
0.5652	Remote Similarity	NPC24772
0.5652	Remote Similarity	NPC261616
0.5652	Remote Similarity	NPC213832
0.5634	Remote Similarity	NPC601275
0.5581	Remote Similarity	NPC101863
0.5556	Remote Similarity	NPC488165
0.5507	Remote Similarity	NPC80590
0.5493	Remote Similarity	NPC151191
0.5479	Remote Similarity	NPC608379
0.5465	Remote Similarity	NPC51947
0.5435	Remote Similarity	NPC204392
0.5429	Remote Similarity	NPC211162
0.5429	Remote Similarity	NPC183374
0.5429	Remote Similarity	NPC304194
0.5426	Remote Similarity	NPC275668
0.5417	Remote Similarity	NPC475061
0.5375	Remote Similarity	NPC486709
0.5366	Remote Similarity	NPC88744
0.5352	Remote Similarity	NPC195395
0.5352	Remote Similarity	NPC168231
0.5294	Remote Similarity	NPC84868
0.5286	Remote Similarity	NPC611062
0.527	Remote Similarity	NPC120840
0.5224	Remote Similarity	NPC475509
0.5224	Remote Similarity	NPC488509
0.5211	Remote Similarity	NPC291373
0.5205	Remote Similarity	NPC474719
0.519	Remote Similarity	NPC606354
0.5181	Remote Similarity	NPC486699
0.5139	Remote Similarity	NPC471901
0.5139	Remote Similarity	NPC277399
0.5119	Remote Similarity	NPC486695
0.5114	Remote Similarity	NPC486700
0.5114	Remote Similarity	NPC275312
0.507	Remote Similarity	NPC30583
0.507	Remote Similarity	NPC481227
0.5068	Remote Similarity	NPC2783
0.5068	Remote Similarity	NPC30522
0.5067	Remote Similarity	NPC169933
0.5067	Remote Similarity	NPC600004
0.5063	Remote Similarity	NPC602512
0.506	Remote Similarity	NPC486706
0.506	Remote Similarity	NPC486705
0.5059	Remote Similarity	NPC290349
0.5055	Remote Similarity	NPC488205

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC532684 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5654
0.1-0.2	3406
0.2-0.3	81
0.3-0.4	4
0.4-0.5	2
0.5-0.6	0
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8983	High Similarity	NPD8035	Phase 2
0.6795	Remote Similarity	NPD8034	Phase 2
0.6462	Remote Similarity	NPD7520	Phase 1

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