NPASS Compound

Natural Product: NPC531365

Natural Product ID	NPC531365
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~{R},7~{a}~{R},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{S})-7-hydroxy-1-isopropenyl-5~{a},5~{b},8,8,11~{a}-pentamethyl-9-oxo-2,3,4,5,6,7,7~{a},10,11,11~{b},12,13,13~{a},13~{b}-tetradecahydro-1~{H}-cyclopenta[a]chrysene-3~{a}-carboxylic acid
IUPAC Name	(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{R},7~{a}~{R},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{S})-7-hydroxy-1-isopropenyl-5~{a},5~{b},8,8,11~{a}-pentamethyl-9-oxo-2,3,4,5,6,7,7~{a},10,11,11~{b},12,13,13~{a},13~{b}-tetradecahydro-1~{H}-cyclopenta[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]

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 84 0 0 0 0 0 0 0 0999 V2000 -4.7593 2.8200 0.0591 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6548 2.4691 -0.6037 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5002 3.3779 -0.3335 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6414 1.3790 -1.5180 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0659 0.8197 -1.7175 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1885 -0.2632 -0.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8115 -0.8770 -0.7167 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9260 -2.1566 -1.4633 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2172 -2.2705 -2.5037 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7383 -3.1878 -1.0893 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3869 -1.2005 0.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9199 -1.6157 0.7260 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.5051 0.2588 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0913 0.4958 1.3600 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4831 -0.0245 -1.0927 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5751 1.0339 -1.6800 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8156 0.3891 -1.9286 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2789 0.0098 -0.5340 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7331 -0.1411 -0.3405 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4086 -1.3530 -0.8127 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4085 1.0043 -1.1241 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8425 1.1575 -0.7750 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2314 0.8183 0.5809 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3403 1.1516 0.9710 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3879 0.0813 1.5771 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9039 -1.2581 1.9246 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5075 0.9449 2.8507 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9828 0.1834 1.1387 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9510 -0.4072 2.0320 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6397 -1.0836 3.0710 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0138 -1.3796 1.4402 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4107 -1.0296 0.0978 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4940 -2.2703 -0.7385 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8873 0.1275 -1.3985 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7109 2.3142 0.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7813 3.7012 0.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8795 3.5290 -1.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9297 4.4010 -0.1076 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8555 3.0968 0.4854 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4726 1.8730 -2.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8233 1.5952 -1.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0470 0.3313 -2.7310 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5297 0.0132 0.2924 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9640 -0.9716 -1.0933 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1737 -3.7706 -1.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6498 -0.4414 1.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9323 -2.1111 1.0206 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7485 -1.8691 1.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8817 -2.5555 0.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0161 -0.0233 2.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1416 0.9164 1.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4449 1.3527 1.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1156 -0.9280 -1.7337 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9900 1.4832 -2.5668 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3114 1.7636 -0.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7629 -0.4210 -2.6412 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4405 1.2458 -2.2608 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0462 0.9775 0.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3837 -1.3305 -1.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5160 -1.2043 -0.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1780 -2.3120 -0.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8767 1.9497 -0.9908 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3806 0.6368 -2.1945 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5182 0.5895 -1.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1200 2.2357 -0.9594 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2347 -1.3529 3.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8631 -1.4306 1.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2618 -2.1087 1.7389 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8153 1.8046 2.7313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3481 0.3587 3.7542 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5395 1.3738 2.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7704 1.3054 1.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3350 0.3565 2.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0323 -1.4009 3.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2289 -1.6062 2.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5784 -2.3647 1.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4157 -2.6921 -1.1398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1574 -2.1407 -1.6461 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9517 -3.1471 -0.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9961 -0.2625 -2.4913 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 2 0 23 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 32 33 1 6 15 34 1 0 34 4 1 0 34 7 1 0 32 13 1 0 32 18 1 0 28 19 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 6 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 14 50 1 0 14 51 1 0 14 52 1 0 15 53 1 6 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 1 20 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 26 66 1 0 26 67 1 0 26 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 6 29 73 1 1 30 74 1 0 31 75 1 0 31 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 6 M END

Standard InCHIKey	FIADIPXEFYWJQV-ODTAYCBISA-N
Standard InCHI	InChI=1S/C30H46O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-21-27(5)12-11-22(32)26(3,4)24(27)20(31)16-29(21,28)7/h18-21,23-24,31H,1,8-16H2,2-7H3,(H,33,34)/t18-,19+,20+,21+,23-,24-,27+,28+,29+,30-/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)CCC(=O)C(C)(C)[C@@H]5[C@H](O)C[C@]43C)[C@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	2.484 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.427 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.668 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.467	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.887	Fsp³:	0.867
MCE-18:	105.857 ? 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:	0.96	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:	0.345	Promiscuous compounds:	0.222

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.485	MDCK Permeability:	-5.104
Pgp-inhibitor:	0.001	Pgp-substrate:	0.001
PAMPA:	0.888 ? 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%):	0.041	30% Bioavailability (F30%):	0.03
50% Bioavailability (F50%):	0.693

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416	MRP1:	0.996
Plasma Protein Binding (PPB):	97.125%	Volume Distribution (VD):	-0.042
Fu:	2.874% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.956	BCRP inhibitor:	0.001
BSEP inhibitor:	0.946

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.59	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.821	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.001 ? 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):

5.001

Half-life (T1/2):

0.782

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.051
Human Hepatotoxicity (H-HT):	0.595	Drug-induced Liver Injury (DILI):	0.484
AMES Toxicity:	0.246	Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.333	Skin Sensitization:	0.979
Carcinogencity:	0.815	Eye Corrosion:	0.068
Eye Irritation:	0.422	Respiratory Toxicity:	0.843
Drug-induced Neurotoxicity:	0.139	Ototoxicity:	0.689
Hematotoxicity:	0.804	Drug-induced Nephrotoxicity:	0.848
Genotoxicity:	0.892	RPMI-8226 Immunitoxicity:	0.045
A549 Cytotoxicity:	0.188	Hek293 Cytotoxicity:	0.204
BCF:	0.526 ? 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:	3.223 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.589 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.051 ? 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
NPO56490	Liquidamber styraciflua	n.a.	n.a.	n.a.	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

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 NPC531365 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	20630
0.1-0.2	25293
0.2-0.3	3496
0.3-0.4	322
0.4-0.5	53
0.5-0.6	45
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474719
0.746	Intermediate Similarity	NPC193907
0.7258	Intermediate Similarity	NPC192744
0.7031	Intermediate Similarity	NPC291373
0.6923	Remote Similarity	NPC277399
0.6923	Remote Similarity	NPC201655
0.6866	Remote Similarity	NPC244356
0.6866	Remote Similarity	NPC224060
0.6866	Remote Similarity	NPC611139
0.6716	Remote Similarity	NPC601275
0.6667	Remote Similarity	NPC606727
0.6286	Remote Similarity	NPC600004
0.6286	Remote Similarity	NPC608379
0.6111	Remote Similarity	NPC603461
0.6056	Remote Similarity	NPC602147
0.6029	Remote Similarity	NPC24772
0.6029	Remote Similarity	NPC488506
0.6029	Remote Similarity	NPC220498
0.6	Remote Similarity	NPC602512
0.5972	Remote Similarity	NPC600907
0.597	Remote Similarity	NPC474482
0.5915	Remote Similarity	NPC603784
0.5882	Remote Similarity	NPC264317
0.5882	Remote Similarity	NPC294438
0.5844	Remote Similarity	NPC611262
0.5833	Remote Similarity	NPC607677
0.5821	Remote Similarity	NPC475745
0.5797	Remote Similarity	NPC488164
0.5797	Remote Similarity	NPC213832
0.5797	Remote Similarity	NPC264005
0.5714	Remote Similarity	NPC606354
0.5652	Remote Similarity	NPC472738
0.5652	Remote Similarity	NPC472739
0.5641	Remote Similarity	NPC605397
0.5556	Remote Similarity	NPC488213
0.5522	Remote Similarity	NPC246445
0.5522	Remote Similarity	NPC68828
0.5429	Remote Similarity	NPC80590
0.5417	Remote Similarity	NPC2783
0.5417	Remote Similarity	NPC151191
0.5417	Remote Similarity	NPC606726
0.5405	Remote Similarity	NPC169933
0.5405	Remote Similarity	NPC601176
0.5405	Remote Similarity	NPC606728
0.5352	Remote Similarity	NPC211162
0.5352	Remote Similarity	NPC183374
0.5342	Remote Similarity	NPC269360
0.5294	Remote Similarity	NPC23884
0.5278	Remote Similarity	NPC195395
0.527	Remote Similarity	NPC488165
0.527	Remote Similarity	NPC486704
0.5205	Remote Similarity	NPC4309
0.5205	Remote Similarity	NPC16377
0.52	Remote Similarity	NPC291028
0.52	Remote Similarity	NPC608881
0.5165	Remote Similarity	NPC487492
0.5122	Remote Similarity	NPC486709
0.5072	Remote Similarity	NPC74363
0.507	Remote Similarity	NPC119743
0.5068	Remote Similarity	NPC271974
0.5068	Remote Similarity	NPC247312
0.5067	Remote Similarity	NPC160506
0.5063	Remote Similarity	NPC607678
0.5063	Remote Similarity	NPC607679

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC531365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5224
0.1-0.2	3792
0.2-0.3	130
0.3-0.4	1
0.4-0.5	1
0.5-0.6	2
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
0.5882	Remote Similarity	NPD7520	Phase 1
0.5067	Remote Similarity	NPD8035	Phase 2

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