NPASS Compound

Natural Product: NPC483706

Natural Product ID	NPC483706
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KDZXFNCKPSQUPG-ZWYLFFMFSA-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 98102 0 0 0 0 0 0 0 0999 V2000 0.0240 2.1153 2.2022 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9834 2.7386 1.1632 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3797 2.2343 1.3556 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8239 1.5141 0.1391 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8367 0.4422 -0.2779 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4328 1.0349 -0.3205 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4950 2.3985 -0.0568 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1932 0.6851 -1.4793 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3038 -0.0846 -1.3633 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2882 -1.4269 -2.0315 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6787 -2.0025 -2.1950 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6993 -3.1250 -2.9887 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2848 -4.1873 -2.3703 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6149 -4.6627 -1.1085 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3990 -5.8430 -0.6049 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0825 -7.1251 -0.9927 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8037 -8.2263 -0.5243 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8511 -8.0574 0.3384 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1794 -6.7796 0.7351 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4685 -5.6953 0.2735 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2425 -6.6229 1.6084 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5688 -9.1716 0.8031 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5469 -1.0815 -2.7949 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7489 -0.0731 -1.8553 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9131 0.8136 -2.2221 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1111 0.0949 -2.3066 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4954 0.7514 -1.8320 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6558 1.9154 -1.0559 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5580 3.1937 -1.6168 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3243 3.2846 -2.8474 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7268 4.3794 -0.7701 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9660 4.2447 0.5047 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1535 5.3240 1.4604 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0894 6.6423 1.0813 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2769 7.6316 2.0429 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5258 7.3473 3.3675 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5840 6.0089 3.7161 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4023 5.0163 2.7849 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8367 5.6914 5.0608 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7142 8.3509 4.3312 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5534 -2.3507 -1.2993 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9494 -0.6334 0.5850 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1063 0.9936 0.1290 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1127 1.3770 -0.7290 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8264 2.2702 -1.5583 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4540 0.8275 -0.7360 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8818 -0.1128 0.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2296 -0.6678 0.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5730 -1.6849 0.9639 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8380 -2.2321 0.9923 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8193 -1.7960 0.1363 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5134 -0.7938 -0.7581 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2330 -0.2512 -0.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5153 -0.3633 -1.6161 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1105 -2.3514 0.1625 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2094 3.3414 1.5818 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1171 2.6859 3.1686 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2910 1.0810 2.4442 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0219 2.1280 1.8463 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0013 3.8481 1.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3474 1.5812 2.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7935 2.2831 -0.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1221 0.1049 -1.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1054 0.5733 0.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4901 -0.2673 -0.2800 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8430 -1.4045 -3.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1416 -2.2387 -1.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3867 -4.0073 -2.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3107 -5.0380 -3.1160 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5384 -3.8920 -0.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5893 -5.0027 -1.3589 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2609 -7.2701 -1.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5222 -9.2006 -0.8525 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7011 -4.6837 0.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1627 -6.9515 1.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3848 -9.5198 0.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8663 -0.5239 -0.8487 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7406 1.2418 -3.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0707 1.6231 -1.4859 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3263 -0.3920 -1.4716 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2919 1.0843 -2.8822 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6565 5.3592 -1.1837 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0276 3.2114 0.8731 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8925 6.9340 0.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2231 8.6713 1.7270 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4593 3.9695 3.1220 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5617 6.3538 5.7661 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8974 9.2748 3.9572 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7208 -2.3145 -0.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6221 -1.4304 0.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1588 1.2141 -1.4559 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1686 -0.4930 0.7850 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7909 -2.0291 1.6435 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0717 -3.0205 1.6975 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0356 0.5276 -1.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9790 0.5160 -1.3399 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2865 -3.0181 -0.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9012 3.1705 2.2668 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 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 18 22 1 0 11 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 10 41 1 0 5 42 1 0 4 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 52 54 1 0 51 55 1 0 3 56 1 0 7 2 1 0 27 9 1 0 38 33 1 0 53 48 1 0 20 15 1 0 1 57 1 0 1 58 1 0 1 59 1 0 2 60 1 6 3 61 1 1 4 62 1 6 5 63 1 6 6 64 1 1 9 65 1 1 10 66 1 6 11 67 1 1 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 16 72 1 0 17 73 1 0 20 74 1 0 21 75 1 0 22 76 1 0 24 77 1 1 25 78 1 0 25 79 1 0 26 80 1 0 27 81 1 6 31 82 1 0 32 83 1 0 34 84 1 0 35 85 1 0 38 86 1 0 39 87 1 0 40 88 1 0 41 89 1 0 42 90 1 0 46 91 1 0 47 92 1 0 49 93 1 0 50 94 1 0 53 95 1 0 54 96 1 0 55 97 1 0 56 98 1 0 M END

Standard InCHIKey	KDZXFNCKPSQUPG-ZWYLFFMFSA-N
Standard InCHI	InChI=1S/C38H42O18/c1-18-31(48)35(55-30(47)11-6-20-3-8-23(41)26(44)15-20)32(49)38(52-18)56-36-33(50)37(51-13-12-21-4-9-24(42)27(45)16-21)53-28(17-39)34(36)54-29(46)10-5-19-2-7-22(40)25(43)14-19/h2-11,14-16,18,28,31-45,48-50H,12-13,17H2,1H3/b10-5+,11-6+/t18-,28+,31-,32+,33+,34+,35+,36+,37+,38-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](OCCc2ccc(c(c2)O)O)O[C@H](CO)[C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O)OC(=O)/C=C/c1ccc(c(c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	786.24	Volume:	746.972 ? Van der Waals volume.
Dense:	1.053	LogP:	1.495 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.883 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.522 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	34.0
TPSA:	291.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.065	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.136	Fsp³:	0.368
MCE-18:	121.846 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.924	Fluc inhibitor:	0.999 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.18 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.664 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.388	Promiscuous compounds:	0.446

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.77	MDCK Permeability:	-5.189
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
PAMPA:	0.994 ? 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):	0.799
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.007
Plasma Protein Binding (PPB):	70.261%	Volume Distribution (VD):	-0.177
Fu:	21.991% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.001

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:	0.248
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.986 ? 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):

4.132

Half-life (T1/2):

4.702

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.717
Human Hepatotoxicity (H-HT):	0.419	Drug-induced Liver Injury (DILI):	0.913
AMES Toxicity:	0.953	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.317	Skin Sensitization:	1.0
Carcinogencity:	0.041	Eye Corrosion:	0.0
Eye Irritation:	0.102	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.018	Drug-induced Nephrotoxicity:	0.108
Genotoxicity:	0.936	RPMI-8226 Immunitoxicity:	0.008
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.833
BCF:	0.645 ? 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:	3.527 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.156 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.684 ? 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
NPO40190	Lippia rubella	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30817148]

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
MIC	3

Activity Type	# Activity
Organism	3

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
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	>	125.0	ug.mL-1	PMID[30817148]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	125.0	ug.mL-1	PMID[30817148]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	125.0	ug.mL-1	PMID[30817148]

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 NPC483706 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	13309
0.1-0.2	33684
0.2-0.3	2441
0.3-0.4	310
0.4-0.5	48
0.5-0.6	39
0.6-0.7	20
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8077	Intermediate Similarity	NPC472350
0.8077	Intermediate Similarity	NPC197316
0.8077	Intermediate Similarity	NPC89105
0.7848	Intermediate Similarity	NPC483705
0.75	Intermediate Similarity	NPC269141
0.7011	Intermediate Similarity	NPC252292
0.6966	Remote Similarity	NPC96795
0.6966	Remote Similarity	NPC264632
0.6932	Remote Similarity	NPC112
0.6932	Remote Similarity	NPC296954
0.6854	Remote Similarity	NPC100998
0.6747	Remote Similarity	NPC46137
0.6629	Remote Similarity	NPC298257
0.6629	Remote Similarity	NPC175214
0.6628	Remote Similarity	NPC76406
0.6552	Remote Similarity	NPC611289
0.6538	Remote Similarity	NPC886
0.6292	Remote Similarity	NPC263829
0.6264	Remote Similarity	NPC205864
0.6264	Remote Similarity	NPC247032
0.617	Remote Similarity	NPC300894
0.617	Remote Similarity	NPC23845
0.6154	Remote Similarity	NPC34587
0.6129	Remote Similarity	NPC34927
0.6042	Remote Similarity	NPC106818
0.6	Remote Similarity	NPC94871
0.5955	Remote Similarity	NPC68092
0.5955	Remote Similarity	NPC134405
0.5909	Remote Similarity	NPC64141
0.58	Remote Similarity	NPC87403
0.58	Remote Similarity	NPC64195
0.573	Remote Similarity	NPC40305
0.573	Remote Similarity	NPC205195
0.5714	Remote Similarity	NPC476384
0.5682	Remote Similarity	NPC81515
0.5652	Remote Similarity	NPC476377
0.5567	Remote Similarity	NPC610636
0.5556	Remote Similarity	NPC171134
0.5481	Remote Similarity	NPC229505
0.5443	Remote Similarity	NPC100558
0.5437	Remote Similarity	NPC306890
0.5392	Remote Similarity	NPC471062
0.5385	Remote Similarity	NPC473427
0.5385	Remote Similarity	NPC328273
0.5361	Remote Similarity	NPC476397
0.5349	Remote Similarity	NPC473285
0.53	Remote Similarity	NPC476382
0.5294	Remote Similarity	NPC476380
0.5294	Remote Similarity	NPC476381
0.5258	Remote Similarity	NPC105005
0.5208	Remote Similarity	NPC476385
0.5204	Remote Similarity	NPC119537
0.5176	Remote Similarity	NPC287597
0.5165	Remote Similarity	NPC260425
0.5158	Remote Similarity	NPC476383
0.5106	Remote Similarity	NPC321184
0.5104	Remote Similarity	NPC106677
0.5098	Remote Similarity	NPC476375
0.5096	Remote Similarity	NPC470933
0.5093	Remote Similarity	NPC488390
0.5055	Remote Similarity	NPC475530
0.505	Remote Similarity	NPC259347
0.5049	Remote Similarity	NPC196063
0.5049	Remote Similarity	NPC604195
0.5045	Remote Similarity	NPC257970

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4751
0.1-0.2	4334
0.2-0.3	63
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8077	Intermediate Similarity	NPD7266	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