NPASS Compound

Natural Product: NPC479497

Natural Product ID	NPC479497
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BIECSHUMCAJDEO-ZVNJSRKKSA-N
IUPAC Name	n.a.
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 82 0 0 0 0 0 0 0 0999 V2000 -6.9769 -2.4246 -0.4497 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6486 -1.1759 -0.5557 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3139 -0.5960 -0.5009 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2304 0.7001 -0.6429 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0870 -1.4629 -0.2823 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9095 -0.5825 -0.3119 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5306 -1.0632 -0.1508 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3297 -2.1006 -1.2795 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0462 -1.5188 1.1626 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6859 -2.6886 1.8390 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 -0.4011 2.1744 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0832 0.7052 1.8214 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1899 1.1135 0.3504 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1722 1.6540 -0.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2139 0.9223 -0.3927 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0365 -0.5429 -0.2997 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7250 -0.8299 -0.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4599 0.0045 -0.5487 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0148 -1.2237 -1.1158 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9474 -2.0911 -0.6111 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9598 -2.3024 0.6269 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9521 -2.7936 -1.4739 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3619 -2.5270 -1.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6355 -2.9623 0.3539 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7328 -1.0873 -1.3326 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9925 3.1641 -0.1564 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9323 3.7846 -0.9533 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7769 4.7999 -0.4995 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6610 5.1509 0.6883 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7556 5.4125 -1.4053 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3153 3.1423 -0.7250 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8978 2.3942 0.3253 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2354 2.5427 0.4018 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8974 3.3108 1.3011 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3322 3.9915 2.1798 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3970 3.3743 1.2728 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3869 1.7617 2.6694 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3768 -2.1837 0.8285 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3412 -3.2729 -0.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0478 -2.7002 -0.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4753 -0.4641 -0.7059 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1008 1.3171 -0.7935 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2934 1.1951 -0.6195 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1622 -2.1651 -1.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0873 0.1312 0.5604 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9478 -0.0736 -1.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3270 -2.3792 -1.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8255 -1.6779 -2.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9529 -3.0529 -0.9084 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0325 -1.8785 0.9983 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9841 -3.4987 1.1810 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4084 -2.3953 2.6298 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8583 -3.1647 2.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0812 -0.0612 2.3144 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7039 -0.8297 3.1420 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9504 0.4388 2.1183 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1585 1.3450 -0.6962 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1929 -0.8947 0.6936 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9354 -0.6613 -2.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6275 -1.9090 -0.8820 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9151 0.4286 -1.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7636 -3.8899 -1.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7830 -2.6368 -2.5384 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0138 -3.1450 -1.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9295 -3.6905 0.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6589 -3.4248 0.4576 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7042 -2.0389 0.9983 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2858 -0.8470 -2.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3607 -0.3813 -0.5748 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8398 -1.0495 -1.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9934 3.5642 0.8662 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0978 4.6956 -2.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 6.3049 -1.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6507 5.7476 -0.8140 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5020 2.9890 1.2273 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7595 4.2346 1.8461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8402 2.4626 1.7057 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7416 3.4317 0.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2479 1.6548 3.1278 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2569 -3.1290 0.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 7 6 1 1 7 8 1 0 7 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 14 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 26 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 12 37 1 0 5 38 1 0 18 7 1 0 18 13 1 0 32 13 1 0 1 39 1 0 1 40 1 0 2 41 1 0 4 42 1 0 4 43 1 0 5 44 1 6 6 45 1 0 6 46 1 0 8 47 1 0 8 48 1 0 8 49 1 0 9 50 1 6 10 51 1 0 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 12 56 1 1 15 57 1 0 16 58 1 1 17 59 1 0 17 60 1 0 18 61 1 6 22 62 1 0 22 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 24 67 1 0 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 1 30 72 1 0 30 73 1 0 30 74 1 0 32 75 1 1 36 76 1 0 36 77 1 0 36 78 1 0 37 79 1 0 38 80 1 0 M END

Standard InCHIKey	BIECSHUMCAJDEO-ZVNJSRKKSA-N
Standard InCHI	InChI=1S/C29H42O9/c1-9-16(4)22(32)14-28(8)17(5)11-24(33)29-21(26(35-18(6)30)38-27(29)36-19(7)31)12-20(13-23(28)29)37-25(34)10-15(2)3/h9,12,15,17,20,22-24,26-27,32-33H,1,4,10-11,13-14H2,2-3,5-8H3/t17-,20+,22-,23+,24+,26+,27-,28-,29-/m1/s1
SMILES	C=CC(=C)[C@@H](C[C@]1(C)[C@H](C)C[C@@H]([C@@]23C(=C[C@@H](C[C@@H]12)OC(=O)CC(C)C)[C@@H](OC(=O)C)O[C@H]3OC(=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.28	Volume:	547.764 ? Van der Waals volume.
Dense:	0.975	LogP:	3.307 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.201 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.721 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	20.0
TPSA:	128.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.197	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.947	Fsp³:	0.69
MCE-18:	95.429 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.832	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.298	Promiscuous compounds:	0.503

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936	MDCK Permeability:	-4.728
Pgp-inhibitor:	0.015	Pgp-substrate:	0.981
PAMPA:	0.974 ? 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):	0.003
20% Bioavailability (F20%):	0.974	30% Bioavailability (F30%):	0.969
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081	MRP1:	0.802
Plasma Protein Binding (PPB):	66.174%	Volume Distribution (VD):	-0.222
Fu:	31.048% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.919	BCRP inhibitor:	0.124
BSEP inhibitor:	0.932

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.017	CYP2C19-substrate:	0.257
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.466
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.461
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.775
HLM stability:	0.998 ? 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):

5.979

Half-life (T1/2):

1.366

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.374
Human Hepatotoxicity (H-HT):	0.552	Drug-induced Liver Injury (DILI):	0.853
AMES Toxicity:	0.957	Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.996	Skin Sensitization:	0.998
Carcinogencity:	0.743	Eye Corrosion:	0.0
Eye Irritation:	0.033	Respiratory Toxicity:	0.973
Drug-induced Neurotoxicity:	0.936	Ototoxicity:	0.744
Hematotoxicity:	0.761	Drug-induced Nephrotoxicity:	0.919
Genotoxicity:	0.972	RPMI-8226 Immunitoxicity:	0.441
A549 Cytotoxicity:	0.899	Hek293 Cytotoxicity:	0.646
BCF:	0.681 ? 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:	3.604 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.575 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.848 ? 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
NPO40811	Casearia kurzii	Species	Salicaceae	Eukaryota	Twigs; Leaves	n.a.	n.a.	PMID[33001650]
NPO40811	Casearia kurzii	Species	Salicaceae	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	1
Activity	13

Activity Type	# Activity
Cell line	14

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
NPT81	Cell line	A549	Homo sapiens	IC50	=	4600.0	nM	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	64.17	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	24.62	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	11.21	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	55.45	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	31.33	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	13.21	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	38.95	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	61.05	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	0.0	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	5.44	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	10.45	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	10.41	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	35.73	%	PMID[33001650]

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 NPC479497 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	18733
0.1-0.2	27571
0.2-0.3	3405
0.3-0.4	50
0.4-0.5	47
0.5-0.6	13
0.6-0.7	29
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	Natural Product ID
0.7812	Intermediate Similarity	NPC479940
0.7812	Intermediate Similarity	NPC81567
0.7812	Intermediate Similarity	NPC488652
0.7273	Intermediate Similarity	NPC488654
0.7273	Intermediate Similarity	NPC479491
0.7231	Intermediate Similarity	NPC479943
0.7077	Intermediate Similarity	NPC602188
0.7015	Intermediate Similarity	NPC201880
0.7015	Intermediate Similarity	NPC7644
0.6765	Remote Similarity	NPC329623
0.6765	Remote Similarity	NPC609711
0.6716	Remote Similarity	NPC488653
0.6714	Remote Similarity	NPC488964
0.6714	Remote Similarity	NPC184512
0.6667	Remote Similarity	NPC330003
0.6667	Remote Similarity	NPC475889
0.6667	Remote Similarity	NPC7613
0.6667	Remote Similarity	NPC470321
0.6667	Remote Similarity	NPC479942
0.6667	Remote Similarity	NPC264867
0.6667	Remote Similarity	NPC473207
0.6667	Remote Similarity	NPC609715
0.6571	Remote Similarity	NPC479941
0.6567	Remote Similarity	NPC488659
0.6567	Remote Similarity	NPC604149
0.6522	Remote Similarity	NPC134270
0.6286	Remote Similarity	NPC488660
0.6286	Remote Similarity	NPC488657
0.6286	Remote Similarity	NPC609880
0.625	Remote Similarity	NPC252296
0.6197	Remote Similarity	NPC238397
0.6197	Remote Similarity	NPC488658
0.6197	Remote Similarity	NPC488655
0.6081	Remote Similarity	NPC127933
0.6056	Remote Similarity	NPC311223
0.6056	Remote Similarity	NPC316974
0.6056	Remote Similarity	NPC128795
0.6027	Remote Similarity	NPC471363
0.5775	Remote Similarity	NPC488656
0.575	Remote Similarity	NPC109376
0.575	Remote Similarity	NPC486751
0.5732	Remote Similarity	NPC224660
0.5541	Remote Similarity	NPC217921
0.5541	Remote Similarity	NPC88013
0.5541	Remote Similarity	NPC135015
0.55	Remote Similarity	NPC116292
0.55	Remote Similarity	NPC87630
0.5238	Remote Similarity	NPC486755
0.5205	Remote Similarity	NPC479936
0.5122	Remote Similarity	NPC179128
0.5062	Remote Similarity	NPC486753

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6892
0.1-0.2	2224
0.2-0.3	34
0.3-0.4	0
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