NPASS Compound

Natural Product: NPC483416

Natural Product ID	NPC483416
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GZZWBJBTMBMOPQ-PZECUPBOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44559738
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 81 85 0 0 0 0 0 0 0 0999 V2000 -8.2309 0.5254 0.3261 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9376 0.8785 1.0119 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2565 1.0097 2.5141 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0938 0.3825 3.2760 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8183 0.8689 2.5706 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7660 0.1505 1.2389 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0537 -0.2008 0.8372 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0727 0.9095 0.2498 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7616 0.6127 -0.1056 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7410 1.2601 0.5991 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9593 2.0975 1.5119 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4049 1.0179 0.3292 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1258 0.1060 -0.6701 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1933 -0.1318 -0.9276 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2595 0.5010 -0.2314 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9583 1.3973 0.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6051 1.6491 1.0189 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3210 2.5655 2.0205 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9269 2.0754 1.4705 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2694 3.4186 1.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5250 0.1529 -0.5936 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7748 0.4784 -0.1742 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3578 -0.7600 0.5196 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7317 -1.1105 0.0069 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6460 -1.3641 -1.4836 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7989 -0.3061 -2.1040 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4853 0.1526 -3.3674 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5482 0.7963 -1.3041 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0267 -2.5995 -1.6625 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6688 -0.1083 0.3366 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7745 -0.4271 1.1042 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9729 -1.6108 1.5251 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7898 0.6016 1.4772 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4495 -0.4641 1.8765 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0952 -0.4761 -1.3094 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3956 -0.2700 -1.0826 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3392 -1.0136 -1.9072 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6662 -0.7572 -2.0446 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5377 -1.5185 -2.7987 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0284 -2.6074 -3.4558 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6944 -2.9249 -3.3625 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8640 -2.1349 -2.5966 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2384 -4.0379 -4.0509 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8926 -3.3908 -4.2242 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7032 0.4591 3.3124 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1516 -0.9982 3.0425 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2719 2.3571 2.8059 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1280 -0.4368 -0.2107 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0711 0.3672 1.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5095 1.2768 -0.4437 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5426 1.8203 0.5920 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2240 0.5402 2.7622 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0966 0.6295 4.3351 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8625 1.9550 2.4874 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1860 -0.7717 1.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4563 -0.8407 -1.7040 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1774 2.2043 2.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5868 3.4649 0.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1282 3.7002 1.7538 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4195 4.0599 1.3723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8437 1.2753 0.5668 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7174 -1.6372 0.4040 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0958 -2.0623 0.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6847 -1.3796 -1.8783 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8081 -0.7383 -2.3636 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1572 -0.6371 -3.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6735 0.3674 -4.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0751 1.0850 -3.1726 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6280 -2.9636 -0.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9997 1.2564 0.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3682 1.2646 2.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7301 0.1335 1.8022 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2716 -0.8137 2.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0849 0.1106 -1.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5718 -1.2496 -2.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8090 -2.3926 -2.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7179 -4.3983 -4.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4423 -2.9288 -4.9197 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5411 -0.4839 3.0636 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5510 -1.4892 3.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4657 2.5009 3.7615 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 16 19 1 0 19 20 1 0 15 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 24 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 23 34 1 0 13 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 41 43 1 0 40 44 1 0 5 45 1 0 4 46 1 0 3 47 1 0 7 2 1 0 36 9 2 0 42 37 1 0 17 12 1 0 28 22 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 6 3 52 1 6 4 53 1 1 5 54 1 6 6 55 1 1 14 56 1 0 18 57 1 0 20 58 1 0 20 59 1 0 20 60 1 0 22 61 1 1 23 62 1 1 24 63 1 1 25 64 1 6 26 65 1 6 27 66 1 0 27 67 1 0 27 68 1 0 29 69 1 0 33 70 1 0 33 71 1 0 33 72 1 0 34 73 1 0 38 74 1 0 39 75 1 0 42 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 46 80 1 0 47 81 1 0 M END

Standard InCHIKey	GZZWBJBTMBMOPQ-PZECUPBOSA-N
Standard InCHI	InChI=1S/C30H34O17/c1-9-18(34)22(38)23(39)29(42-9)47-28-21(37)17-15(45-25(28)12-5-6-13(32)14(33)7-12)8-16(26(41-4)20(17)36)46-30-24(40)27(44-11(3)31)19(35)10(2)43-30/h5-10,18-19,22-24,27,29-30,32-36,38-40H,1-4H3/t9-,10-,18-,19-,22+,23+,24+,27+,29-,30-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(c(c2O)OC)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)OC(=O)C)O)oc1c1ccc(c(c1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.18	Volume:	610.359 ? Van der Waals volume.
Dense:	1.091	LogP:	0.478 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.978 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.82 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	31.0
TPSA:	264.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.117	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.953	Fsp³:	0.467
MCE-18:	127.818 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.677	Fluc inhibitor:	0.242 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.848 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.586 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.1	Promiscuous compounds:	0.399

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.163	MDCK Permeability:	-5.326
Pgp-inhibitor:	0.002	Pgp-substrate:	0.901
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):	0.238
20% Bioavailability (F20%):	0.63	30% Bioavailability (F30%):	0.971
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.516
Plasma Protein Binding (PPB):	81.86%	Volume Distribution (VD):	-0.04
Fu:	18.035% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.98
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.122
BSEP inhibitor:	0.12

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.175
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.96 ? 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):

2.541

Half-life (T1/2):

4.36

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.286
Human Hepatotoxicity (H-HT):	0.432	Drug-induced Liver Injury (DILI):	0.95
AMES Toxicity:	0.783	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.021	Skin Sensitization:	0.997
Carcinogencity:	0.025	Eye Corrosion:	0.0
Eye Irritation:	0.056	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.964
Hematotoxicity:	0.071	Drug-induced Nephrotoxicity:	0.171
Genotoxicity:	0.673	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.611	Hek293 Cytotoxicity:	0.19
BCF:	0.51 ? 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:	3.174 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.851 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.055 ? 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
NPO9114	Kalanchoe brasiliensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724848]
NPO9114	Kalanchoe brasiliensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7853000]
NPO9114	Kalanchoe brasiliensis	Species	Crassulaceae	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 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.	IC50	=	10.0	ug.mL-1	PMID[7853000]

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 NPC483416 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	14983
0.1-0.2	31600
0.2-0.3	2495
0.3-0.4	422
0.4-0.5	241
0.5-0.6	86
0.6-0.7	19
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8621	High Similarity	NPC483413
0.8276	Intermediate Similarity	NPC483415
0.8025	Intermediate Similarity	NPC27640
0.7865	Intermediate Similarity	NPC483414
0.7209	Intermediate Similarity	NPC488071
0.7204	Intermediate Similarity	NPC606657
0.6875	Remote Similarity	NPC483412
0.6782	Remote Similarity	NPC305811
0.6782	Remote Similarity	NPC271692
0.6333	Remote Similarity	NPC59534
0.62	Remote Similarity	NPC473073
0.618	Remote Similarity	NPC127546
0.618	Remote Similarity	NPC57625
0.618	Remote Similarity	NPC173637
0.618	Remote Similarity	NPC317489
0.618	Remote Similarity	NPC223424
0.618	Remote Similarity	NPC600591
0.617	Remote Similarity	NPC265115
0.6129	Remote Similarity	NPC605784
0.6087	Remote Similarity	NPC129217
0.6064	Remote Similarity	NPC488072
0.6044	Remote Similarity	NPC46420
0.6044	Remote Similarity	NPC24043
0.6044	Remote Similarity	NPC52550
0.6022	Remote Similarity	NPC21666
0.598	Remote Similarity	NPC470445
0.596	Remote Similarity	NPC126784
0.596	Remote Similarity	NPC241423
0.5934	Remote Similarity	NPC158674
0.5914	Remote Similarity	NPC611303
0.59	Remote Similarity	NPC470443
0.5824	Remote Similarity	NPC249281
0.5806	Remote Similarity	NPC42773
0.5806	Remote Similarity	NPC45522
0.5769	Remote Similarity	NPC470446
0.5714	Remote Similarity	NPC480466
0.5714	Remote Similarity	NPC488078
0.5638	Remote Similarity	NPC117260
0.5638	Remote Similarity	NPC201292
0.5607	Remote Similarity	NPC470451
0.56	Remote Similarity	NPC233994
0.5591	Remote Similarity	NPC136042
0.5579	Remote Similarity	NPC175107
0.5579	Remote Similarity	NPC219904
0.5567	Remote Similarity	NPC276377
0.5543	Remote Similarity	NPC111929
0.5543	Remote Similarity	NPC320283
0.5543	Remote Similarity	NPC41121
0.5532	Remote Similarity	NPC84362
0.5532	Remote Similarity	NPC349108
0.5532	Remote Similarity	NPC603655
0.551	Remote Similarity	NPC116864
0.551	Remote Similarity	NPC244776
0.5488	Remote Similarity	NPC18772
0.5481	Remote Similarity	NPC64755
0.5464	Remote Similarity	NPC223747
0.5464	Remote Similarity	NPC116458
0.5464	Remote Similarity	NPC246943
0.5455	Remote Similarity	NPC254540
0.5446	Remote Similarity	NPC203259
0.5446	Remote Similarity	NPC33054
0.5446	Remote Similarity	NPC176740
0.5446	Remote Similarity	NPC471725
0.5446	Remote Similarity	NPC134532
0.5446	Remote Similarity	NPC602582
0.5437	Remote Similarity	NPC211532
0.5437	Remote Similarity	NPC488364
0.5429	Remote Similarity	NPC473071
0.5408	Remote Similarity	NPC355481
0.5385	Remote Similarity	NPC72016
0.5376	Remote Similarity	NPC135599
0.5376	Remote Similarity	NPC73855
0.5376	Remote Similarity	NPC113968
0.5376	Remote Similarity	NPC328940
0.5376	Remote Similarity	NPC277174
0.5376	Remote Similarity	NPC606877
0.534	Remote Similarity	NPC488073
0.534	Remote Similarity	NPC488074
0.5312	Remote Similarity	NPC599850
0.53	Remote Similarity	NPC251417
0.5294	Remote Similarity	NPC293626
0.5294	Remote Similarity	NPC150164
0.5283	Remote Similarity	NPC470447
0.5278	Remote Similarity	NPC470455
0.5273	Remote Similarity	NPC292019
0.5273	Remote Similarity	NPC202908
0.5263	Remote Similarity	NPC145038
0.5263	Remote Similarity	NPC56077
0.5263	Remote Similarity	NPC281131
0.5263	Remote Similarity	NPC253662
0.5263	Remote Similarity	NPC265530
0.5263	Remote Similarity	NPC179950
0.5263	Remote Similarity	NPC88789
0.5263	Remote Similarity	NPC491374
0.5259	Remote Similarity	NPC241781
0.5243	Remote Similarity	NPC473571
0.5243	Remote Similarity	NPC110941
0.5243	Remote Similarity	NPC186816
0.5208	Remote Similarity	NPC45638
0.5189	Remote Similarity	NPC486577
0.5158	Remote Similarity	NPC19709
0.5158	Remote Similarity	NPC238376
0.5146	Remote Similarity	NPC605592
0.5138	Remote Similarity	NPC14187
0.5096	Remote Similarity	NPC204693
0.5093	Remote Similarity	NPC470449
0.5052	Remote Similarity	NPC105025
0.5052	Remote Similarity	NPC488080
0.5052	Remote Similarity	NPC169977
0.505	Remote Similarity	NPC211594
0.5043	Remote Similarity	NPC488079

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4970
0.1-0.2	4133
0.2-0.3	40
0.3-0.4	2
0.4-0.5	3
0.5-0.6	2
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
0.5446	Remote Similarity	NPD6797	Phase 2
0.5429	Remote Similarity	NPD7251	Phase 2

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