NPASS Compound

Natural Product: NPC106818

Natural Product ID	NPC106818
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DPVXAVLHDIAHDO-CVIHBIPCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL540151
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 103107 0 0 0 0 0 0 0 0999 V2000 -4.7181 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0481 -0.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 -1.1424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -0.1782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1700 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 6.4004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 7.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0105 9.3548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2709 10.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1219 11.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3824 13.2734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7919 13.7864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9410 12.8223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6805 11.3451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3505 13.3353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0524 15.2637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 5.8874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 5.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4681 6.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2077 7.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 8.5069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3567 8.9581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5058 9.9223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3567 10.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6172 12.3636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0268 12.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1758 11.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9153 10.4353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2768 14.1757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2558 8.6232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9410 0.3349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4996 0.7860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7600 -0.6912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1696 -1.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3186 -0.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7282 -0.7531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9887 -2.2303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8396 -3.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4300 -2.6814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1001 -4.6717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3982 -2.7433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9791 3.6241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 0.3349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -2.1065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 -2.1065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2312 1.7444 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.4419 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1277 -0.1782 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 2.1469 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8394 -0.7265 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -2.4414 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4132 -1.3761 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5302 1.9190 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9791 5.5525 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3586 7.3218 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 7.6171 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6844 8.3162 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4667 9.6153 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4877 9.0943 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2877 11.2832 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7667 14.2376 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8296 10.3809 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4996 12.3711 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4619 15.7767 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 3.6241 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3549 6.7016 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2833 4.4034 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2597 9.9810 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3209 7.8090 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9472 11.3995 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4540 9.6885 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3567 13.8409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1172 12.3636 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1758 13.8409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5854 11.3995 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9258 13.2115 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3539 9.0008 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4153 10.4353 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0268 15.4748 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7446 8.4404 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 1.7502 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6110 -1.6554 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0582 1.2372 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8772 0.2111 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2810 -3.6456 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9510 -5.6359 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6587 -4.2205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 4.1372 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5302 1.7051 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9720 -1.7691 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 -2.6196 0.0000 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 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 30 37 1 6 24 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 48 50 1 0 47 51 1 0 10 52 1 0 5 53 1 0 4 54 1 0 3 55 1 0 7 2 1 0 38 9 1 0 49 44 1 0 20 15 1 0 35 30 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 1 3 60 1 6 4 61 1 1 5 62 1 1 6 63 1 6 9 64 1 1 10 65 1 6 11 66 1 1 13 67 1 0 13 68 1 0 14 69 1 0 14 70 1 0 16 71 1 0 17 72 1 0 20 73 1 0 21 74 1 0 22 75 1 0 24 76 1 1 25 77 1 0 25 78 1 0 29 79 1 0 29 80 1 0 31 81 1 0 31 82 1 0 32 83 1 0 32 84 1 0 33 85 1 1 34 86 1 0 34 87 1 0 35 88 1 0 35 89 1 0 36 90 1 0 37 91 1 0 38 92 1 6 42 93 1 0 43 94 1 0 45 95 1 0 46 96 1 0 49 97 1 0 50 98 1 0 51 99 1 0 52100 1 0 53101 1 0 54102 1 0 55103 1 0 M END

Standard InCHIKey	DPVXAVLHDIAHDO-CVIHBIPCSA-N
Standard InCHI	InChI=1S/C37H48O18/c1-18-29(45)30(46)31(47)36(52-18)55-34-32(48)35(50-13-10-20-3-6-23(40)25(42)15-20)53-26(17-51-28(44)16-37(49)11-8-21(38)9-12-37)33(34)54-27(43)7-4-19-2-5-22(39)24(41)14-19/h2-7,14-15,18,21,26,29-36,38-42,45-49H,8-13,16-17H2,1H3/b7-4+/t18-,21-,26+,29-,30+,31+,32+,33+,34+,35+,36-,37+/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](COC(=O)C[C@]2(CC[C@@H](CC2)O)O)[C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	780.28	Volume:	740.222 ? Van der Waals volume.
Dense:	1.054	LogP:	0.9 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.474 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.452 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	33.0
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:	0.07	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.191	Fsp³:	0.568
MCE-18:	131.414 ? 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:	0.714	Fluc inhibitor:	0.655 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.098 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.657 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.103	Promiscuous compounds:	0.551

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.449	MDCK Permeability:	-5.254
Pgp-inhibitor:	0.0	Pgp-substrate:	0.037
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):	0.037
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:	0.005
Plasma Protein Binding (PPB):	66.045%	Volume Distribution (VD):	-0.261
Fu:	29.977% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
BSEP inhibitor:	0.003

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:	0.007
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.939 ? 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):

3.358

Half-life (T1/2):

4.921

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.159
Human Hepatotoxicity (H-HT):	0.677	Drug-induced Liver Injury (DILI):	0.339
AMES Toxicity:	0.86	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.676	Skin Sensitization:	1.0
Carcinogencity:	0.107	Eye Corrosion:	0.0
Eye Irritation:	0.148	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.021	Drug-induced Nephrotoxicity:	0.892
Genotoxicity:	0.734	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.789
BCF:	0.547 ? 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:	3.292 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.031 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.364 ? 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
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19361168]
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28152	Jacaranda caucana	Species	Bignoniaceae	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
EC50	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.	EC50	=	1270.0	nM	PMID[19361168]

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 NPC106818 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	11983
0.1-0.2	33687
0.2-0.3	3660
0.3-0.4	431
0.4-0.5	35
0.5-0.6	31
0.6-0.7	19
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9111	High Similarity	NPC87403
0.8372	Intermediate Similarity	NPC611289
0.8046	Intermediate Similarity	NPC76406
0.7609	Intermediate Similarity	NPC205864
0.7609	Intermediate Similarity	NPC298257
0.7609	Intermediate Similarity	NPC247032
0.7609	Intermediate Similarity	NPC175214
0.7474	Intermediate Similarity	NPC300894
0.7474	Intermediate Similarity	NPC23845
0.7416	Intermediate Similarity	NPC472350
0.7416	Intermediate Similarity	NPC197316
0.7416	Intermediate Similarity	NPC89105
0.6947	Remote Similarity	NPC269141
0.6566	Remote Similarity	NPC100998
0.6531	Remote Similarity	NPC252292
0.6522	Remote Similarity	NPC81515
0.6465	Remote Similarity	NPC112
0.6452	Remote Similarity	NPC46137
0.6436	Remote Similarity	NPC259347
0.6408	Remote Similarity	NPC196063
0.6408	Remote Similarity	NPC604195
0.6383	Remote Similarity	NPC64141
0.6311	Remote Similarity	NPC476384
0.6226	Remote Similarity	NPC64195
0.6146	Remote Similarity	NPC483705
0.6132	Remote Similarity	NPC470933
0.6075	Remote Similarity	NPC470934
0.6061	Remote Similarity	NPC263829
0.6055	Remote Similarity	NPC229505
0.6042	Remote Similarity	NPC483706
0.6038	Remote Similarity	NPC476380
0.598	Remote Similarity	NPC119537
0.5941	Remote Similarity	NPC34587
0.5922	Remote Similarity	NPC34927
0.5918	Remote Similarity	NPC68092
0.5888	Remote Similarity	NPC476381
0.5865	Remote Similarity	NPC96795
0.5865	Remote Similarity	NPC264632
0.5865	Remote Similarity	NPC610636
0.5825	Remote Similarity	NPC296954
0.5664	Remote Similarity	NPC476386
0.5607	Remote Similarity	NPC141455
0.5603	Remote Similarity	NPC257970
0.56	Remote Similarity	NPC134405
0.5556	Remote Similarity	NPC205195
0.5543	Remote Similarity	NPC287597
0.551	Remote Similarity	NPC260425
0.551	Remote Similarity	NPC235294
0.5437	Remote Similarity	NPC106677
0.5413	Remote Similarity	NPC476375
0.5376	Remote Similarity	NPC886
0.5368	Remote Similarity	NPC473285
0.5263	Remote Similarity	NPC94871
0.5263	Remote Similarity	NPC34293
0.5234	Remote Similarity	NPC476397
0.5179	Remote Similarity	NPC476378
0.51	Remote Similarity	NPC475530
0.5093	Remote Similarity	NPC600370
0.5083	Remote Similarity	NPC470927
0.5048	Remote Similarity	NPC476377
0.5043	Remote Similarity	NPC188393
0.5043	Remote Similarity	NPC306890

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC106818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4979
0.1-0.2	4079
0.2-0.3	89
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7416	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