NPASS Compound

Natural Product: NPC483817

Natural Product ID	NPC483817
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FCQSIIVNJCMJLB-CKVFQFCTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	134152616
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 84 88 0 0 0 0 0 0 0 0999 V2000 6.6254 0.2338 -1.4049 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8398 0.6509 -0.4195 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4994 -0.2823 0.6293 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0891 -0.6701 0.8558 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3996 -1.3255 -0.2835 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1818 -2.6175 -0.6441 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0168 -1.7510 -0.1348 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7219 -2.7580 0.9393 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2009 -2.7111 1.1109 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2709 -1.7649 -0.0008 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2679 -2.5874 -1.2629 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5587 -1.0984 0.2892 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7430 -1.9151 -0.2173 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9484 -1.3176 0.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1977 0.0148 -0.1430 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3275 0.7713 0.5278 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6662 0.4976 -0.1509 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4840 0.4403 1.9733 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0379 2.2412 0.3479 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6011 2.5689 -1.0615 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3491 1.8473 -1.4752 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0107 0.8539 -0.3605 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1942 1.3989 0.7170 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6828 0.2960 -0.2362 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6871 0.6426 -1.2900 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7206 0.2354 -0.9987 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9124 -0.7816 0.0461 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9532 -0.1725 1.4292 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2526 2.9168 0.5529 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4109 2.0574 -0.4835 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9766 2.3167 -0.7381 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8868 2.7370 0.7672 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1229 3.2749 1.5843 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2613 2.7443 0.9885 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0133 -0.7871 -1.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9426 0.8535 -2.2427 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8508 0.1865 1.6040 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0971 -1.2350 0.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0958 -1.3273 1.7774 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5516 0.2407 1.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5004 -0.6909 -1.1815 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0841 -3.3050 0.2099 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2064 -2.3837 -0.9354 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7017 -3.1186 -1.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7831 -2.2902 -1.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2646 -2.6290 1.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0012 -3.7788 0.5541 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2407 -3.7008 0.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1009 -2.3746 2.0979 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3251 -2.8811 -1.5378 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2301 -3.5831 -1.1444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0747 -2.0275 -2.1601 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7050 -1.0627 1.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6543 -2.9805 -0.0010 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9622 -1.7120 -1.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7406 -1.2306 1.6064 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8040 -1.9741 0.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6053 -0.2576 -1.1648 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7256 0.9718 -1.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4470 0.9458 0.4847 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8125 -0.5896 -0.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6550 -0.6747 2.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4385 0.8876 2.3203 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6211 0.7271 2.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3214 2.6471 1.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3932 2.3731 -1.8022 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4468 3.6844 -1.0780 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5620 2.5826 -1.6380 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5090 1.2553 -2.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 2.3692 0.6517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3905 1.0571 1.7538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0431 0.1916 -2.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7145 1.7399 -1.4524 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1876 -0.1049 -1.9453 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3185 1.1439 -0.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0295 -0.0982 1.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2713 0.9042 1.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5913 -0.7278 2.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8392 2.8583 -0.2442 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9787 2.6095 -1.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5033 1.6717 -1.4731 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8791 3.3623 -1.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4296 2.4119 0.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6546 2.8634 1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 16 19 1 0 19 20 1 0 20 21 1 0 22 21 1 6 22 23 1 0 24 23 1 1 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 19 29 1 0 2 30 1 0 30 31 1 0 30 32 1 0 32 33 2 0 32 34 1 0 27 7 1 0 27 10 1 0 24 12 1 0 22 15 1 0 24 22 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 6 6 42 1 0 6 43 1 0 6 44 1 0 7 45 1 6 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 11 51 1 0 11 52 1 0 12 53 1 1 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 6 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 18 64 1 0 19 65 1 1 20 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 23 70 1 0 23 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 30 80 1 6 31 81 1 0 31 82 1 0 31 83 1 0 34 84 1 0 M END

Standard InCHIKey	FCQSIIVNJCMJLB-CKVFQFCTSA-N
Standard InCHI	InChI=1S/C31H50O3/c1-19(21(3)26(33)34)8-9-20(2)22-12-14-29(7)24-11-10-23-27(4,5)25(32)13-15-30(23)18-31(24,30)17-16-28(22,29)6/h20-25,32H,1,8-18H2,2-7H3,(H,33,34)/t20-,21-,22-,23+,24+,25-,28-,29+,30-,31+/m1/s1
SMILES	C=C(CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H](CC[C@]54C[C@@]35CC[C@]12C)O)[C@@H](C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.38	Volume:	523.047 ? Van der Waals volume.
Dense:	0.899	LogP:	4.006 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.175 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.515 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.396	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.599	Fsp³:	0.903
MCE-18:	137.186 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.837	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.497	Promiscuous compounds:	0.179

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.587	MDCK Permeability:	-5.073
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
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):	0.0
20% Bioavailability (F20%):	0.001	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.495

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109	MRP1:	0.725
Plasma Protein Binding (PPB):	93.491%	Volume Distribution (VD):	-0.431
Fu:	8.495% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.042
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.194	CYP2C19-substrate:	0.022
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.8
HLM stability:	0.023 ? 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):

2.676

Half-life (T1/2):

1.277

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.076
Human Hepatotoxicity (H-HT):	0.237	Drug-induced Liver Injury (DILI):	0.049
AMES Toxicity:	0.14	Rat Oral Acute Toxicity:	0.308
Maximum Recommended Daily Dose:	0.433	Skin Sensitization:	0.992
Carcinogencity:	0.489	Eye Corrosion:	0.081
Eye Irritation:	0.901	Respiratory Toxicity:	0.919
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.361
Hematotoxicity:	0.54	Drug-induced Nephrotoxicity:	0.567
Genotoxicity:	0.698	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.029	Hek293 Cytotoxicity:	0.114
BCF:	2.373 ? 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:	5.103 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.183 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.78 ? 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
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	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
Activity	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	>	50.0	%	PMID[27466882]

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 NPC483817 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	22995
0.1-0.2	22757
0.2-0.3	3438
0.3-0.4	489
0.4-0.5	123
0.5-0.6	29
0.6-0.7	23
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
0.7091	Intermediate Similarity	NPC254509
0.7037	Intermediate Similarity	NPC607543
0.6964	Remote Similarity	NPC472342
0.6833	Remote Similarity	NPC110923
0.6833	Remote Similarity	NPC74296
0.6724	Remote Similarity	NPC76518
0.6613	Remote Similarity	NPC195366
0.6613	Remote Similarity	NPC114743
0.6607	Remote Similarity	NPC331618
0.6607	Remote Similarity	NPC257191
0.6607	Remote Similarity	NPC196358
0.6491	Remote Similarity	NPC200243
0.6379	Remote Similarity	NPC273366
0.6349	Remote Similarity	NPC85379
0.6349	Remote Similarity	NPC144909
0.6349	Remote Similarity	NPC476304
0.629	Remote Similarity	NPC476186
0.625	Remote Similarity	NPC41577
0.6207	Remote Similarity	NPC85346
0.6207	Remote Similarity	NPC65897
0.6207	Remote Similarity	NPC80237
0.614	Remote Similarity	NPC299948
0.614	Remote Similarity	NPC241085
0.6102	Remote Similarity	NPC195530
0.6061	Remote Similarity	NPC146937
0.5968	Remote Similarity	NPC89747
0.5932	Remote Similarity	NPC604180
0.5902	Remote Similarity	NPC472341
0.5833	Remote Similarity	NPC470830
0.5833	Remote Similarity	NPC479659
0.5738	Remote Similarity	NPC70982
0.5738	Remote Similarity	NPC473279
0.5738	Remote Similarity	NPC22133
0.5714	Remote Similarity	NPC473238
0.5667	Remote Similarity	NPC82623
0.5538	Remote Similarity	NPC18384
0.5522	Remote Similarity	NPC488282
0.5484	Remote Similarity	NPC49168
0.5484	Remote Similarity	NPC5046
0.5469	Remote Similarity	NPC134481
0.5441	Remote Similarity	NPC242864
0.5312	Remote Similarity	NPC12722
0.5312	Remote Similarity	NPC195489
0.5286	Remote Similarity	NPC288906
0.5286	Remote Similarity	NPC475007
0.5224	Remote Similarity	NPC307776
0.5156	Remote Similarity	NPC67872
0.5152	Remote Similarity	NPC474962
0.5147	Remote Similarity	NPC321690
0.5147	Remote Similarity	NPC479654
0.5147	Remote Similarity	NPC479656
0.5079	Remote Similarity	NPC145552
0.5077	Remote Similarity	NPC477858
0.507	Remote Similarity	NPC611460

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6297
0.1-0.2	2753
0.2-0.3	96
0.3-0.4	3
0.4-0.5	1
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