NPASS Compound

Natural Product: NPC52169

Natural Product ID	NPC52169
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,4Ar,6As,6Br,10S,12Ar,14Bs)-10-Hydroxy-2-(Hydroxymethyl)-2,6A,6B,9,9,12A-Hexamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-4A-Carboxylic Acid
IUPAC Name	(2S,4aR,6aS,6bR,10S,12aR,14bS)-10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1733823
PubChem CID	23641088
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 82 86 0 0 0 0 0 0 0 0999 V2000 -4.7271 2.1371 0.3617 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7932 0.6267 0.0634 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9897 0.5590 -0.9190 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5599 0.0855 -0.5562 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7354 1.2835 -0.9528 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3805 1.0515 -1.4792 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7184 -0.2618 -1.1262 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9384 -1.1332 -2.3747 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3470 -0.8544 0.1096 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9557 0.0031 1.2869 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5432 0.0917 1.3716 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3400 0.0532 0.3194 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8219 0.1433 0.5152 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4783 1.4109 0.2111 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9588 1.2525 0.6173 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6401 2.5264 0.1616 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5768 0.1197 -0.1839 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8958 -1.1715 0.0737 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3973 -1.0780 -0.1224 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9887 -1.1475 -1.5486 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4961 -1.2649 -1.6648 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7481 -0.0876 -1.0283 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1449 1.1721 -1.8181 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8445 -2.2941 0.5417 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0500 -2.1875 1.4815 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2391 -3.5272 0.0844 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1460 1.1240 2.0840 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6479 2.2687 2.7056 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8361 -1.0452 0.0727 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0956 -2.3335 -0.7462 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2957 -1.4363 1.4494 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1075 -0.3821 2.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3037 0.0079 1.3042 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1624 -1.0641 1.0957 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1175 2.3801 1.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6107 2.7505 -0.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7919 2.3532 0.7090 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8714 0.8661 -0.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1105 -0.4530 -1.3215 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8350 1.3413 -1.6877 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9102 -0.3211 -1.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7418 2.0907 -0.1902 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3644 1.7780 -1.7787 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4562 1.1800 -2.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7546 1.9338 -1.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9999 -1.1243 -2.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4506 -0.6202 -3.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4815 -2.1067 -2.3298 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8805 -1.8471 0.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2785 -0.3766 2.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2864 1.0498 1.2435 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0061 0.1968 2.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0149 -0.0214 1.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5849 1.7190 -0.8431 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0913 2.2248 0.8576 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9721 2.4114 -0.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9258 3.3655 0.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5114 2.6806 0.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6314 0.0529 0.1078 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4495 0.3826 -1.2579 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3076 -1.9488 -0.5891 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0509 -1.4715 1.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3740 -2.1583 -1.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4698 -0.4310 -2.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1772 -2.1803 -1.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3017 -1.3706 -2.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2496 2.0593 -1.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4382 1.4421 -2.6087 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0854 0.9486 -2.4103 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0318 -4.3819 0.5552 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2631 1.1733 2.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8244 0.1911 2.5392 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1714 3.0457 2.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7713 -2.1640 -1.5939 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 -3.0522 -0.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1814 -2.8985 -0.9339 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5421 -1.8156 2.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0209 -2.3219 1.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5142 -0.7940 3.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5060 0.4842 2.3925 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8846 0.7466 1.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8842 -1.6370 0.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 19 24 1 1 24 25 2 0 24 26 1 0 15 27 1 0 27 28 1 0 9 29 1 0 29 30 1 6 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 2 1 0 29 4 1 0 22 7 1 0 22 12 1 0 19 13 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 8 46 1 0 8 47 1 0 8 48 1 0 9 49 1 0 10 50 1 0 10 51 1 0 11 52 1 0 13 53 1 1 14 54 1 0 14 55 1 0 16 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 23 67 1 0 23 68 1 0 23 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 28 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 32 79 1 0 32 80 1 0 33 81 1 1 34 82 1 0 M END

Standard InCHIKey	CZWBKSDPBWNHGO-XZTHESQKSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-25(2)21-9-12-29(6)22(27(21,4)11-10-23(25)32)8-7-19-20-17-26(3,18-31)13-15-30(20,24(33)34)16-14-28(19,29)5/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21?,22?,23-,26-,27-,28+,29+,30-/m0/s1
SMILES	CC1(C)C2CC[C@]3(C)C(CC=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]34C)C(=O)O)CO)[C@@]2(C)CC[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.011 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.059 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.655 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.418	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.811	Fsp³:	0.9
MCE-18:	105.368 ? 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:	0.553	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.325	Promiscuous compounds:	0.064

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.323	MDCK Permeability:	-4.946
Pgp-inhibitor:	0.001	Pgp-substrate:	0.376
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):	0.001
20% Bioavailability (F20%):	0.941	30% Bioavailability (F30%):	0.074
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.705	MRP1:	0.993
Plasma Protein Binding (PPB):	87.145%	Volume Distribution (VD):	-0.23
Fu:	10.834% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.209	BCRP inhibitor:	0.011
BSEP inhibitor:	0.832

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.243	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.481	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.148
HLM stability:	0.0 ? 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):

4.617

Half-life (T1/2):

0.879

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.069
Human Hepatotoxicity (H-HT):	0.845	Drug-induced Liver Injury (DILI):	0.048
AMES Toxicity:	0.126	Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.606	Skin Sensitization:	0.976
Carcinogencity:	0.899	Eye Corrosion:	0.0
Eye Irritation:	0.532	Respiratory Toxicity:	0.718
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.801
Hematotoxicity:	0.116	Drug-induced Nephrotoxicity:	0.749
Genotoxicity:	0.056	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.291	Hek293 Cytotoxicity:	0.21
BCF:	1.12 ? 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:	3.932 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.526 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.8 ? 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
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	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
Potency	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	89125.1	nM	PubChem BioAssay data set

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 NPC52169 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	21552
0.1-0.2	23562
0.2-0.3	3541
0.3-0.4	757
0.4-0.5	263
0.5-0.6	98
0.6-0.7	42
0.7-0.8	0
0.8-0.85	0
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC182797
1.0	High Similarity	NPC488562
0.8667	High Similarity	NPC121798
0.8667	High Similarity	NPC234346
0.85	High Similarity	NPC480946
0.85	High Similarity	NPC130577
0.85	High Similarity	NPC142415
0.85	High Similarity	NPC102683
0.7656	Intermediate Similarity	NPC472149
0.75	Intermediate Similarity	NPC270768
0.75	Intermediate Similarity	NPC59263
0.75	Intermediate Similarity	NPC210106
0.7344	Intermediate Similarity	NPC187722
0.7344	Intermediate Similarity	NPC198664
0.7273	Intermediate Similarity	NPC298554
0.7231	Intermediate Similarity	NPC51700
0.7231	Intermediate Similarity	NPC88716
0.7231	Intermediate Similarity	NPC68160
0.7231	Intermediate Similarity	NPC606443
0.7121	Intermediate Similarity	NPC609452
0.7015	Intermediate Similarity	NPC202728
0.7015	Intermediate Similarity	NPC158059
0.7015	Intermediate Similarity	NPC293564
0.6812	Remote Similarity	NPC130520
0.6567	Remote Similarity	NPC274330
0.6522	Remote Similarity	NPC228784
0.6522	Remote Similarity	NPC324341
0.6522	Remote Similarity	NPC601810
0.6479	Remote Similarity	NPC324063
0.6471	Remote Similarity	NPC282616
0.6471	Remote Similarity	NPC229281
0.6471	Remote Similarity	NPC64872
0.6471	Remote Similarity	NPC171203
0.6471	Remote Similarity	NPC84319
0.6471	Remote Similarity	NPC25906
0.6471	Remote Similarity	NPC307426
0.6471	Remote Similarity	NPC98442
0.6471	Remote Similarity	NPC52021
0.6471	Remote Similarity	NPC242468
0.6471	Remote Similarity	NPC599947
0.6418	Remote Similarity	NPC477872
0.6377	Remote Similarity	NPC61543
0.6377	Remote Similarity	NPC293048
0.6377	Remote Similarity	NPC225585
0.6377	Remote Similarity	NPC158141
0.6301	Remote Similarity	NPC474727
0.6286	Remote Similarity	NPC136697
0.6232	Remote Similarity	NPC7260
0.6232	Remote Similarity	NPC210037
0.6232	Remote Similarity	NPC275809
0.6232	Remote Similarity	NPC120968
0.6232	Remote Similarity	NPC227467
0.6232	Remote Similarity	NPC273621
0.6232	Remote Similarity	NPC112866
0.6197	Remote Similarity	NPC191412
0.6197	Remote Similarity	NPC114159
0.6197	Remote Similarity	NPC6818
0.6184	Remote Similarity	NPC603645
0.6143	Remote Similarity	NPC231063
0.6143	Remote Similarity	NPC282395
0.6143	Remote Similarity	NPC130278
0.6143	Remote Similarity	NPC110308
0.6111	Remote Similarity	NPC127689
0.6027	Remote Similarity	NPC187933
0.6027	Remote Similarity	NPC116457
0.5972	Remote Similarity	NPC263393
0.5972	Remote Similarity	NPC91010
0.597	Remote Similarity	NPC604575
0.5946	Remote Similarity	NPC6255
0.5915	Remote Similarity	NPC106112
0.5915	Remote Similarity	NPC261935
0.5915	Remote Similarity	NPC88116
0.5882	Remote Similarity	NPC488215
0.5857	Remote Similarity	NPC610937
0.5833	Remote Similarity	NPC29765
0.5775	Remote Similarity	NPC195019
0.575	Remote Similarity	NPC204407
0.5694	Remote Similarity	NPC18872
0.5694	Remote Similarity	NPC290614
0.5694	Remote Similarity	NPC481360
0.5679	Remote Similarity	NPC28198
0.5679	Remote Similarity	NPC476123
0.5679	Remote Similarity	NPC606107
0.5672	Remote Similarity	NPC101475
0.5616	Remote Similarity	NPC200752
0.5616	Remote Similarity	NPC120840
0.56	Remote Similarity	NPC222047
0.5556	Remote Similarity	NPC37038
0.5541	Remote Similarity	NPC118519
0.5541	Remote Similarity	NPC474963
0.5513	Remote Similarity	NPC188833
0.5507	Remote Similarity	NPC159168
0.5488	Remote Similarity	NPC283849
0.5479	Remote Similarity	NPC71074
0.5479	Remote Similarity	NPC37221
0.5479	Remote Similarity	NPC605937
0.5455	Remote Similarity	NPC290598
0.5455	Remote Similarity	NPC27765
0.5455	Remote Similarity	NPC198621
0.5455	Remote Similarity	NPC30590
0.5455	Remote Similarity	NPC216940
0.5455	Remote Similarity	NPC122418
0.5455	Remote Similarity	NPC491014
0.5441	Remote Similarity	NPC311078
0.5405	Remote Similarity	NPC259733
0.5405	Remote Similarity	NPC158371
0.5405	Remote Similarity	NPC207922
0.5405	Remote Similarity	NPC173089
0.5362	Remote Similarity	NPC235341
0.5362	Remote Similarity	NPC253807
0.5362	Remote Similarity	NPC40394
0.5362	Remote Similarity	NPC158662
0.5357	Remote Similarity	NPC286347
0.5352	Remote Similarity	NPC280654
0.5352	Remote Similarity	NPC161751
0.5352	Remote Similarity	NPC474972
0.5352	Remote Similarity	NPC600543
0.5349	Remote Similarity	NPC18982
0.5349	Remote Similarity	NPC284807
0.5342	Remote Similarity	NPC307282
0.5342	Remote Similarity	NPC156981
0.5333	Remote Similarity	NPC132824
0.5333	Remote Similarity	NPC610635
0.5325	Remote Similarity	NPC96580
0.5294	Remote Similarity	NPC100383
0.5287	Remote Similarity	NPC475627
0.5287	Remote Similarity	NPC191410
0.527	Remote Similarity	NPC38754
0.527	Remote Similarity	NPC73489
0.527	Remote Similarity	NPC173744
0.527	Remote Similarity	NPC204961
0.527	Remote Similarity	NPC73004
0.5263	Remote Similarity	NPC137072
0.5263	Remote Similarity	NPC25299
0.5263	Remote Similarity	NPC481322
0.5263	Remote Similarity	NPC148964
0.5227	Remote Similarity	NPC475472
0.5224	Remote Similarity	NPC120098
0.5211	Remote Similarity	NPC72638
0.5205	Remote Similarity	NPC18064
0.52	Remote Similarity	NPC32407
0.52	Remote Similarity	NPC263548
0.52	Remote Similarity	NPC606320
0.5195	Remote Similarity	NPC296164
0.5195	Remote Similarity	NPC157113
0.5195	Remote Similarity	NPC174663
0.5172	Remote Similarity	NPC294112
0.5172	Remote Similarity	NPC473538
0.5169	Remote Similarity	NPC270667
0.5169	Remote Similarity	NPC164194
0.5143	Remote Similarity	NPC472608
0.5139	Remote Similarity	NPC246708
0.5132	Remote Similarity	NPC247139
0.5125	Remote Similarity	NPC54909
0.5111	Remote Similarity	NPC262970
0.507	Remote Similarity	NPC238992
0.507	Remote Similarity	NPC95594
0.5068	Remote Similarity	NPC242631
0.5068	Remote Similarity	NPC477579
0.5067	Remote Similarity	NPC271614
0.5067	Remote Similarity	NPC111214
0.5055	Remote Similarity	NPC136877
0.5055	Remote Similarity	NPC12288

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC52169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6194
0.1-0.2	2897
0.2-0.3	52
0.3-0.4	4
0.4-0.5	2
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