NPASS Compound

Natural Product: NPC597833

Natural Product ID	NPC597833
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3~{S},5~{R},10~{R},13~{R},14~{S},17~{R})-14-hydroxy-13-methyl-17-(5-oxo-2~{H}-furan-3-yl)-3-[(2~{S},5~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
IUPAC Name	(3~{S},5~{R},10~{R},13~{R},14~{S},17~{R})-14-hydroxy-13-methyl-17-(5-oxo-2~{H}-furan-3-yl)-3-[(2~{S},5~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
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 85 0 0 0 0 0 0 0 0999 V2000 7.1459 1.3838 1.4825 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6036 0.1809 0.7500 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7534 0.6262 -0.2619 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9361 -0.3990 -0.7332 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7730 -0.3880 0.0170 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6296 -0.0855 -0.7424 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7158 -1.2303 -0.6639 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2746 -0.9932 -0.4410 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0558 0.1592 0.4766 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7839 0.0129 1.7429 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4908 -0.9244 2.0582 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4068 0.4937 0.6835 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0832 -0.4843 1.5886 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3803 -0.9967 1.0147 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2724 0.1318 0.5016 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6228 0.9839 1.6686 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3456 -0.4621 -0.2902 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5564 -0.9249 0.4067 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9491 -2.1899 0.4080 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1556 -2.3400 1.1644 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8387 -3.3974 1.3972 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5273 -1.1203 1.6520 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5552 -0.2011 1.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6606 0.5906 -1.3581 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2252 0.8852 -1.8193 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5307 1.0217 -0.4851 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6088 2.3670 -0.1327 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0734 0.5722 -0.6474 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4386 1.5266 -1.5946 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0441 1.5512 -1.5975 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6467 1.3791 -0.2370 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1263 1.2339 -0.2689 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5719 -1.7527 -0.5792 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0956 -2.5412 -1.6505 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0722 -1.7164 -0.7058 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4587 -1.6771 -2.0494 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7039 -0.6081 0.0982 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6183 -1.1021 1.0366 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9247 1.9132 0.8919 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3337 2.0308 1.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6963 0.9768 2.3786 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0438 -0.4533 1.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7140 -0.1603 -1.8035 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0239 0.0657 -1.7919 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8053 -1.8096 -1.6362 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0568 -2.0053 0.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2110 -0.8525 -1.4279 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1831 -1.9452 -0.0415 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7157 0.8014 2.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4240 1.5132 1.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4186 -1.3623 1.7114 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2343 -0.0268 2.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9580 -1.4841 1.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2070 -1.7580 0.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7053 1.6158 1.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4095 1.7448 1.4553 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7851 0.4315 2.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9042 -1.3039 -0.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4471 -3.0322 -0.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1220 0.2291 2.1529 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1010 0.5736 0.6299 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0853 1.4993 -0.9370 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2432 0.1049 -2.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1687 1.7871 -2.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8085 -0.0054 -2.3530 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8328 2.7264 0.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1688 -0.4723 -1.0554 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7714 1.2306 -2.6331 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8717 2.5609 -1.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4906 0.8303 -2.3430 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3690 2.5580 -1.9695 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3744 2.2609 0.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4965 1.4501 0.7781 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5385 2.0628 -0.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2705 -2.2641 0.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4535 -2.1468 -2.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4516 -2.6849 -0.2896 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4549 -1.5246 -2.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2293 0.0599 -0.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3482 -0.4191 1.0781 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 1 1 10 11 2 0 9 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 17 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 4 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 2 1 0 32 6 1 0 31 9 1 0 28 12 1 0 26 15 1 0 23 18 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 4 43 1 6 6 44 1 6 7 45 1 0 7 46 1 0 8 47 1 0 8 48 1 0 10 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 6 19 59 1 0 23 60 1 0 23 61 1 0 24 62 1 0 24 63 1 0 25 64 1 0 25 65 1 0 27 66 1 0 28 67 1 0 29 68 1 0 29 69 1 0 30 70 1 0 30 71 1 0 31 72 1 1 32 73 1 0 32 74 1 0 33 75 1 0 34 76 1 0 35 77 1 0 36 78 1 0 37 79 1 6 38 80 1 0 M END

Standard InCHIKey	QITDIWRKOXBKAM-BJISRVMWSA-N
Standard InCHI	InChI=1S/C29H42O9/c1-15-23(32)24(33)25(34)26(37-15)38-18-5-9-28(14-30)17(12-18)3-4-21-20(28)6-8-27(2)19(7-10-29(21,27)35)16-11-22(31)36-13-16/h11,14-15,17-21,23-26,32-35H,3-10,12-13H2,1-2H3/t15?,17-,18+,19-,20?,21?,23-,24?,25?,26-,27-,28-,29+/m1/s1
SMILES	CC1O[C@H](O[C@H]2CC[C@]3(C=O)C4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)C4CC[C@@H]3C2)C(O)C(O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.28	Volume:	530.004 ? Van der Waals volume.
Dense:	1.008	LogP:	1.075 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.681 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.508 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	142.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.24	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.233	Fsp³:	0.862
MCE-18:	111.222 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.764	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.086	Promiscuous compounds:	0.006

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.245	MDCK Permeability:	-5.246
Pgp-inhibitor:	0.0	Pgp-substrate:	0.971
PAMPA:	0.996 ? 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):	0.015
20% Bioavailability (F20%):	0.662	30% Bioavailability (F30%):	0.576
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116	MRP1:	0.908
Plasma Protein Binding (PPB):	78.811%	Volume Distribution (VD):	-0.397
Fu:	19.689% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.837
OATP1B3 inhibitor:	0.897	BCRP inhibitor:	0.029
BSEP inhibitor:	0.134

ADMET: Metabolism

CYP1A2-inhibitor:	0.189	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.428	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.104	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	0.267
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.875
HLM stability:	0.126 ? 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):

1.993

Half-life (T1/2):

2.682

ADMET: Toxicity

hERG Blockers:	0.256	hERG Blockers (10um):	0.788
Human Hepatotoxicity (H-HT):	0.853	Drug-induced Liver Injury (DILI):	0.747
AMES Toxicity:	0.927	Rat Oral Acute Toxicity:	0.986
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.941	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.985
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.789
Hematotoxicity:	0.349	Drug-induced Nephrotoxicity:	0.694
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.795
A549 Cytotoxicity:	0.518	Hek293 Cytotoxicity:	0.992
BCF:	0.558 ? 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:	3.432 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.249 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.336 ? 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
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	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 NPC597833 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	13726
0.1-0.2	30659
0.2-0.3	4863
0.3-0.4	370
0.4-0.5	63
0.5-0.6	79
0.6-0.7	57
0.7-0.8	2
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469750
0.8784	High Similarity	NPC480914
0.863	High Similarity	NPC99620
0.8289	Intermediate Similarity	NPC76572
0.8289	Intermediate Similarity	NPC193382
0.8158	Intermediate Similarity	NPC480915
0.8077	Intermediate Similarity	NPC179412
0.8077	Intermediate Similarity	NPC471356
0.7927	Intermediate Similarity	NPC188234
0.7792	Intermediate Similarity	NPC196429
0.7722	Intermediate Similarity	NPC250556
0.7692	Intermediate Similarity	NPC5311
0.7692	Intermediate Similarity	NPC17896
0.7692	Intermediate Similarity	NPC469755
0.7692	Intermediate Similarity	NPC284406
0.7692	Intermediate Similarity	NPC197707
0.7692	Intermediate Similarity	NPC251866
0.7647	Intermediate Similarity	NPC232785
0.7647	Intermediate Similarity	NPC486139
0.7529	Intermediate Similarity	NPC125077
0.75	Intermediate Similarity	NPC240070
0.7468	Intermediate Similarity	NPC77299
0.7468	Intermediate Similarity	NPC480906
0.7436	Intermediate Similarity	NPC99728
0.7436	Intermediate Similarity	NPC87250
0.7436	Intermediate Similarity	NPC244402
0.7436	Intermediate Similarity	NPC50305
0.7356	Intermediate Similarity	NPC329986
0.7356	Intermediate Similarity	NPC140092
0.7273	Intermediate Similarity	NPC486138
0.7273	Intermediate Similarity	NPC276838
0.725	Intermediate Similarity	NPC157376
0.725	Intermediate Similarity	NPC142066
0.725	Intermediate Similarity	NPC603972
0.7059	Intermediate Similarity	NPC30483
0.7059	Intermediate Similarity	NPC470897
0.7024	Intermediate Similarity	NPC480907
0.7	Intermediate Similarity	NPC471633
0.6988	Remote Similarity	NPC471353
0.6977	Remote Similarity	NPC236973
0.6782	Remote Similarity	NPC32177
0.6782	Remote Similarity	NPC292467
0.6782	Remote Similarity	NPC469756
0.6782	Remote Similarity	NPC275901
0.6747	Remote Similarity	NPC199428
0.6747	Remote Similarity	NPC109448
0.6747	Remote Similarity	NPC310341
0.6742	Remote Similarity	NPC486143
0.6742	Remote Similarity	NPC486142
0.6742	Remote Similarity	NPC486149
0.6737	Remote Similarity	NPC486150
0.6705	Remote Similarity	NPC480910
0.6705	Remote Similarity	NPC480909
0.6628	Remote Similarity	NPC72260
0.6556	Remote Similarity	NPC486135
0.6556	Remote Similarity	NPC486137
0.6506	Remote Similarity	NPC84987
0.6506	Remote Similarity	NPC309034
0.6413	Remote Similarity	NPC486146
0.6404	Remote Similarity	NPC27363
0.6395	Remote Similarity	NPC9499
0.6395	Remote Similarity	NPC471360
0.6395	Remote Similarity	NPC469751
0.6395	Remote Similarity	NPC471361
0.6395	Remote Similarity	NPC86159
0.6395	Remote Similarity	NPC469752
0.6395	Remote Similarity	NPC469754
0.6395	Remote Similarity	NPC70542
0.6395	Remote Similarity	NPC305574
0.6353	Remote Similarity	NPC84949
0.6353	Remote Similarity	NPC480562
0.6353	Remote Similarity	NPC74945
0.6353	Remote Similarity	NPC31354
0.6353	Remote Similarity	NPC69576
0.6316	Remote Similarity	NPC486144
0.6316	Remote Similarity	NPC486145
0.6316	Remote Similarity	NPC486147
0.6316	Remote Similarity	NPC486148
0.631	Remote Similarity	NPC219085
0.6304	Remote Similarity	NPC469749
0.6279	Remote Similarity	NPC77319
0.6279	Remote Similarity	NPC471351
0.6279	Remote Similarity	NPC471355
0.619	Remote Similarity	NPC473852
0.6154	Remote Similarity	NPC32793
0.6154	Remote Similarity	NPC116075
0.6146	Remote Similarity	NPC475590
0.6146	Remote Similarity	NPC486136
0.6071	Remote Similarity	NPC158344
0.6023	Remote Similarity	NPC483822
0.6023	Remote Similarity	NPC93883
0.6023	Remote Similarity	NPC277374
0.602	Remote Similarity	NPC120390
0.602	Remote Similarity	NPC74259
0.602	Remote Similarity	NPC475419
0.5974	Remote Similarity	NPC196931
0.596	Remote Similarity	NPC474908
0.596	Remote Similarity	NPC486134
0.596	Remote Similarity	NPC486141
0.5955	Remote Similarity	NPC471354
0.5955	Remote Similarity	NPC27507
0.5938	Remote Similarity	NPC476221
0.5938	Remote Similarity	NPC477709
0.5909	Remote Similarity	NPC88668
0.5882	Remote Similarity	NPC474418
0.5851	Remote Similarity	NPC55532
0.5843	Remote Similarity	NPC484202
0.5825	Remote Similarity	NPC286809
0.5795	Remote Similarity	NPC10823
0.5784	Remote Similarity	NPC474423
0.5745	Remote Similarity	NPC475629
0.573	Remote Similarity	NPC83287
0.5729	Remote Similarity	NPC146857
0.5729	Remote Similarity	NPC247190
0.5684	Remote Similarity	NPC208193
0.5652	Remote Similarity	NPC173555
0.5638	Remote Similarity	NPC475556
0.5638	Remote Similarity	NPC311706
0.5638	Remote Similarity	NPC486130
0.5618	Remote Similarity	NPC604978
0.5579	Remote Similarity	NPC231518
0.5579	Remote Similarity	NPC486127
0.5579	Remote Similarity	NPC488944
0.5579	Remote Similarity	NPC610296
0.5568	Remote Similarity	NPC486129
0.5556	Remote Similarity	NPC253456
0.5556	Remote Similarity	NPC159338
0.5556	Remote Similarity	NPC180079
0.5506	Remote Similarity	NPC6108
0.5506	Remote Similarity	NPC486126
0.5506	Remote Similarity	NPC479356
0.5506	Remote Similarity	NPC89514
0.5506	Remote Similarity	NPC479355
0.5474	Remote Similarity	NPC608063
0.5443	Remote Similarity	NPC268829
0.5443	Remote Similarity	NPC295110
0.5435	Remote Similarity	NPC193893
0.5393	Remote Similarity	NPC484211
0.5385	Remote Similarity	NPC171619
0.5376	Remote Similarity	NPC488161
0.5376	Remote Similarity	NPC16569
0.5361	Remote Similarity	NPC59288
0.534	Remote Similarity	NPC329675
0.534	Remote Similarity	NPC194716
0.5333	Remote Similarity	NPC34390
0.5309	Remote Similarity	NPC222875
0.5309	Remote Similarity	NPC25177
0.53	Remote Similarity	NPC486132
0.53	Remote Similarity	NPC486131
0.5275	Remote Similarity	NPC243196
0.5275	Remote Similarity	NPC480908
0.5258	Remote Similarity	NPC264336
0.525	Remote Similarity	NPC187302
0.5248	Remote Similarity	NPC479360
0.5248	Remote Similarity	NPC486128
0.5248	Remote Similarity	NPC479359
0.5248	Remote Similarity	NPC488943
0.5248	Remote Similarity	NPC488942
0.5217	Remote Similarity	NPC146456
0.5213	Remote Similarity	NPC91
0.5208	Remote Similarity	NPC40749
0.5192	Remote Similarity	NPC117445
0.5192	Remote Similarity	NPC308262
0.5185	Remote Similarity	NPC480913
0.5165	Remote Similarity	NPC99080
0.5161	Remote Similarity	NPC471359
0.5158	Remote Similarity	NPC5883
0.5149	Remote Similarity	NPC475219
0.5122	Remote Similarity	NPC72772
0.5104	Remote Similarity	NPC163365
0.5098	Remote Similarity	NPC488938
0.5098	Remote Similarity	NPC488937
0.5051	Remote Similarity	NPC470094
0.5048	Remote Similarity	NPC486140

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC597833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5849
0.1-0.2	3173
0.2-0.3	110
0.3-0.4	3
0.4-0.5	3
0.5-0.6	7
0.6-0.7	1
0.7-0.8	2
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
0.7722	Intermediate Similarity	NPD7507	Pre-clinical
0.7692	Intermediate Similarity	NPD7319	Approved
0.6628	Remote Similarity	NPD8294	Phase 4
0.5851	Remote Similarity	NPD8377	Phase 4
0.573	Remote Similarity	NPD7327	Approved
0.573	Remote Similarity	NPD7328	Phase 4
0.5652	Remote Similarity	NPD8296	Phase 4
0.5579	Remote Similarity	NPD8033	Approved
0.5217	Remote Similarity	NPD8335	Phase 4
0.5161	Remote Similarity	NPD8380	Approved

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