NPASS Compound

Natural Product: NPC605937

Natural Product ID	NPC605937
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HFGSQOYIOKBQOW-XOYVNYDSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL391534
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 82 86 0 0 0 0 0 0 0 0999 V2000 -2.8189 2.1943 -1.2395 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6886 1.1245 -0.6364 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0024 1.1238 -1.4580 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7527 2.4008 -1.2820 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7916 -0.0403 -0.9146 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2343 -0.6056 0.3610 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8359 -1.2101 0.1698 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0091 -2.5214 -0.5230 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4546 -2.6796 -1.6360 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7455 -3.5496 0.0080 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2122 -1.3405 1.5014 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7289 -1.5250 1.5494 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9910 -0.4538 0.7618 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2339 0.8002 1.6151 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6616 -0.3757 -0.5440 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9290 -0.4530 -1.6277 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5210 -0.6158 -1.7489 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1448 -0.1164 -0.4725 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6532 -0.1836 -0.5768 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2134 -1.4520 -1.0803 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0042 0.8082 -1.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3457 1.3859 -1.6628 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0235 1.1954 -2.9007 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2881 0.9940 -0.6067 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1899 0.0101 -1.0924 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7092 0.5604 0.7038 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4592 -0.6193 1.2169 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9340 1.6697 1.7603 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2245 0.4353 0.6212 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6428 -0.0270 1.9340 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1390 0.0489 1.9231 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4893 -0.6400 0.7331 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8079 -2.1170 1.0032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1140 -0.2393 -0.7322 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2656 2.6620 -2.1450 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8145 1.8440 -1.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7385 3.0234 -0.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0966 1.4165 0.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7681 0.9095 -2.5203 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8565 2.2511 -1.2993 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4984 2.8645 -0.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5052 3.1197 -2.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8224 0.2571 -0.7260 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8246 -0.8801 -1.6494 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8771 -1.4986 0.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3037 0.0421 1.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1252 -4.2951 -0.5473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6146 -0.5638 2.1812 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6322 -2.3005 1.9452 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5234 -2.5476 1.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5020 -1.5086 2.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8742 0.5297 2.6262 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3243 0.9264 1.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8369 1.7085 1.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5005 -0.3808 -2.5976 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -1.6279 -2.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8624 0.0415 -2.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9499 0.9956 -0.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4823 -1.4714 -2.1695 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4316 -2.2371 -1.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0921 -1.8539 -0.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8681 0.2851 -2.6962 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1960 1.5984 -1.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2308 2.5147 -1.6384 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8144 1.7575 -2.9730 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9814 1.8488 -0.4000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9573 -0.2428 -2.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1273 -1.1102 0.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8874 -1.4361 1.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2123 -0.3493 2.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9347 1.2345 2.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9217 2.1034 1.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1229 2.4400 1.6344 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8702 1.5216 0.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0498 -0.9776 2.3203 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9621 0.7164 2.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8941 1.1274 1.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8464 -0.4052 2.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3095 -2.3702 1.9880 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4142 -2.7983 0.2650 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8792 -2.2647 1.2882 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 -0.6058 -1.7677 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 3 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 2 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 22 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 1 15 34 1 0 34 2 1 0 34 7 1 0 32 13 1 0 32 18 1 0 29 19 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 6 4 40 1 0 4 41 1 0 4 42 1 0 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 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 6 20 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 22 64 1 1 23 65 1 0 24 66 1 1 25 67 1 0 27 68 1 0 27 69 1 0 27 70 1 0 28 71 1 0 28 72 1 0 28 73 1 0 29 74 1 6 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 34 82 1 6 M END

Standard InCHIKey	HFGSQOYIOKBQOW-XOYVNYDSSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-17-10-13-30(25(33)34)15-14-28(6)19(23(30)18(17)2)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h8,17-18,20-24,31-32H,9-16H2,1-7H3,(H,33,34)/t17-,18+,20+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
SMILES	C[C@H]1[C@H](C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.693 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.267 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.925 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	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:	0.405	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.907	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:	0.785	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.065 ? 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:	0.314	Promiscuous compounds:	0.089

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.569	MDCK Permeability:	-5.09
Pgp-inhibitor:	0.004	Pgp-substrate:	0.038
PAMPA:	0.999 ? 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):	0.005
20% Bioavailability (F20%):	0.732	30% Bioavailability (F30%):	0.279
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.537	MRP1:	0.977
Plasma Protein Binding (PPB):	93.193%	Volume Distribution (VD):	-0.457
Fu:	6.858% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.962	BCRP inhibitor:	0.027
BSEP inhibitor:	0.725

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.015	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

3.104

Half-life (T1/2):

1.173

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.049
Human Hepatotoxicity (H-HT):	0.663	Drug-induced Liver Injury (DILI):	0.68
AMES Toxicity:	0.405	Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.224	Skin Sensitization:	0.954
Carcinogencity:	0.861	Eye Corrosion:	0.037
Eye Irritation:	0.709	Respiratory Toxicity:	0.911
Drug-induced Neurotoxicity:	0.041	Ototoxicity:	0.651
Hematotoxicity:	0.756	Drug-induced Nephrotoxicity:	0.881
Genotoxicity:	0.647	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.326	Hek293 Cytotoxicity:	0.157
BCF:	1.335 ? 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:	3.63 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.034 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.464 ? 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
NPO54842	Styrax camporum	Species	Styracaceae	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	4
EC50	7

Activity Type	# Activity
Individual protein	3
Unchecked	1
Organism	1
Non-molecular	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2681	Individual protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	116000.0	nM	PMID[18517260]
NPT2681	Individual protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	163000.0	nM	PMID[21439694]
NPT2681	Individual protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	162181.01	nM	PMID[21439694]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	115500.0	nM	PMID[17869102]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[27416552]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	29100.0	nM	PMID[27416552]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	24900.0	nM	PMID[27416552]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	EC50	>	30000.0	nM	PMID[27416552]

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 NPC605937 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	25550
0.1-0.2	20713
0.2-0.3	2884
0.3-0.4	415
0.4-0.5	163
0.5-0.6	78
0.6-0.7	26
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC71074
0.8548	High Similarity	NPC32407
0.8548	High Similarity	NPC263548
0.8548	High Similarity	NPC606320
0.8387	Intermediate Similarity	NPC37221
0.7727	Intermediate Similarity	NPC25299
0.7727	Intermediate Similarity	NPC481322
0.7656	Intermediate Similarity	NPC51700
0.7656	Intermediate Similarity	NPC88716
0.7656	Intermediate Similarity	NPC68160
0.7538	Intermediate Similarity	NPC300351
0.7424	Intermediate Similarity	NPC259733
0.7424	Intermediate Similarity	NPC158371
0.7424	Intermediate Similarity	NPC207922
0.7424	Intermediate Similarity	NPC305464
0.7424	Intermediate Similarity	NPC87095
0.7424	Intermediate Similarity	NPC19376
0.7424	Intermediate Similarity	NPC25848
0.7385	Intermediate Similarity	NPC84319
0.7385	Intermediate Similarity	NPC52021
0.7385	Intermediate Similarity	NPC599947
0.7273	Intermediate Similarity	NPC472149
0.7015	Intermediate Similarity	NPC61543
0.7015	Intermediate Similarity	NPC293048
0.7015	Intermediate Similarity	NPC225585
0.6806	Remote Similarity	NPC230151
0.6667	Remote Similarity	NPC173089
0.6667	Remote Similarity	NPC477288
0.662	Remote Similarity	NPC20235
0.662	Remote Similarity	NPC299996
0.6567	Remote Similarity	NPC274050
0.6567	Remote Similarity	NPC162632
0.6522	Remote Similarity	NPC88116
0.6471	Remote Similarity	NPC274330
0.6471	Remote Similarity	NPC477289
0.6429	Remote Similarity	NPC40092
0.6338	Remote Similarity	NPC247139
0.6286	Remote Similarity	NPC231063
0.6286	Remote Similarity	NPC282395
0.6286	Remote Similarity	NPC173744
0.6286	Remote Similarity	NPC204961
0.6286	Remote Similarity	NPC73004
0.6286	Remote Similarity	NPC110308
0.6286	Remote Similarity	NPC609452
0.6164	Remote Similarity	NPC117663
0.6143	Remote Similarity	NPC306541
0.6111	Remote Similarity	NPC485589
0.6092	Remote Similarity	NPC479747
0.6092	Remote Similarity	NPC479746
0.6081	Remote Similarity	NPC479743
0.6	Remote Similarity	NPC96916
0.5857	Remote Similarity	NPC43686
0.5844	Remote Similarity	NPC96693
0.5811	Remote Similarity	NPC477290
0.5802	Remote Similarity	NPC57362
0.5789	Remote Similarity	NPC485586
0.5789	Remote Similarity	NPC485588
0.5753	Remote Similarity	NPC202728
0.5753	Remote Similarity	NPC158059
0.5753	Remote Similarity	NPC293564
0.5732	Remote Similarity	NPC177246
0.5694	Remote Similarity	NPC195019
0.5676	Remote Similarity	NPC610635
0.5641	Remote Similarity	NPC188833
0.5634	Remote Similarity	NPC609710
0.5556	Remote Similarity	NPC480946
0.5556	Remote Similarity	NPC187722
0.5556	Remote Similarity	NPC130577
0.5556	Remote Similarity	NPC142415
0.5556	Remote Similarity	NPC102683
0.5541	Remote Similarity	NPC256247
0.5541	Remote Similarity	NPC188102
0.5526	Remote Similarity	NPC157113
0.5479	Remote Similarity	NPC182797
0.5479	Remote Similarity	NPC307335
0.5479	Remote Similarity	NPC74855
0.5479	Remote Similarity	NPC52169
0.5479	Remote Similarity	NPC479079
0.5479	Remote Similarity	NPC488562
0.5467	Remote Similarity	NPC35239
0.5467	Remote Similarity	NPC201657
0.5444	Remote Similarity	NPC304110
0.5444	Remote Similarity	NPC27518
0.5444	Remote Similarity	NPC611516
0.5432	Remote Similarity	NPC485585
0.5405	Remote Similarity	NPC106112
0.5405	Remote Similarity	NPC261935
0.5405	Remote Similarity	NPC111214
0.5405	Remote Similarity	NPC481360
0.5395	Remote Similarity	NPC127689
0.5395	Remote Similarity	NPC62516
0.5385	Remote Similarity	NPC178093
0.5333	Remote Similarity	NPC488214
0.5333	Remote Similarity	NPC145667
0.5333	Remote Similarity	NPC136697
0.5333	Remote Similarity	NPC479077
0.5278	Remote Similarity	NPC488506
0.5278	Remote Similarity	NPC220498
0.527	Remote Similarity	NPC307282
0.527	Remote Similarity	NPC606443
0.5269	Remote Similarity	NPC479745
0.5263	Remote Similarity	NPC88847
0.5263	Remote Similarity	NPC191412
0.5263	Remote Similarity	NPC114159
0.5263	Remote Similarity	NPC132824
0.5263	Remote Similarity	NPC6818
0.525	Remote Similarity	NPC54909
0.5238	Remote Similarity	NPC485882
0.52	Remote Similarity	NPC38754
0.5165	Remote Similarity	NPC479744
0.5135	Remote Similarity	NPC86372
0.5135	Remote Similarity	NPC136313
0.5128	Remote Similarity	NPC187933
0.5128	Remote Similarity	NPC116457
0.5128	Remote Similarity	NPC174663
0.5128	Remote Similarity	NPC284865
0.5068	Remote Similarity	NPC49320
0.5067	Remote Similarity	NPC270768
0.5067	Remote Similarity	NPC59263
0.5067	Remote Similarity	NPC210106
0.5067	Remote Similarity	NPC282616
0.5067	Remote Similarity	NPC229281
0.5067	Remote Similarity	NPC121798
0.5067	Remote Similarity	NPC234346
0.5067	Remote Similarity	NPC488213
0.5065	Remote Similarity	NPC9613
0.5062	Remote Similarity	NPC233012
0.5057	Remote Similarity	NPC485587
0.5052	Remote Similarity	NPC118033

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605937 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6842
0.1-0.2	2266
0.2-0.3	38
0.3-0.4	4
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