NPASS Compound

Natural Product: NPC304769

Natural Product ID	NPC304769
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LKZDFKLGDGSGEO-FFFMXZAGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10371538
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 73 77 0 0 0 0 0 0 0 0999 V2000 -1.4568 -2.5354 -1.9887 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8663 -2.8107 -3.1926 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3407 -1.8031 -3.9630 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4257 -0.5307 -3.4938 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0393 -0.2592 -2.2477 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5601 -1.2283 -1.4757 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2754 -1.0316 -0.2400 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1372 0.0768 0.5239 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9426 0.0883 1.7235 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8613 1.0808 2.4632 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7718 -0.9388 2.0589 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5419 -0.9103 3.2251 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3698 -1.9679 3.5352 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4432 -3.0650 2.6927 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6774 -3.0475 1.5728 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8304 -2.0212 1.2070 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1139 -2.0333 0.1342 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2912 -4.1254 3.0301 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4408 0.2034 4.0418 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4005 1.1140 0.3663 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6517 2.1766 0.2018 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8113 1.9197 0.3960 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3302 2.6699 1.6651 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2047 4.1562 1.2853 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2601 4.3240 0.9157 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2768 4.8912 -0.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5135 6.0682 -0.5255 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9948 3.2163 1.1446 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5990 4.9078 2.3633 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6857 2.4409 1.7392 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1401 0.5673 0.5641 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2440 0.1532 -0.1164 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1912 -0.5088 0.8672 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0493 -2.0322 0.8447 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3573 -2.5582 -0.5605 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0891 -1.4269 -1.5154 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9960 -1.9186 -2.9359 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7644 -0.8956 -3.8244 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9155 -0.7971 -1.0875 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6791 -2.9891 -0.6347 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7454 -2.3233 1.2104 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5038 -0.0963 0.7091 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2631 -2.1041 -5.1987 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8683 -3.3420 -1.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7982 -3.8193 -3.5639 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0275 0.2856 -4.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1029 0.7633 -1.9547 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9770 -1.9542 4.4463 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7241 -3.8975 0.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4821 -4.4129 3.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3186 0.5739 4.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8963 2.7058 -0.7757 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4682 2.3178 -0.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7417 2.4296 2.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8847 4.3127 0.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6064 5.1832 1.5732 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2457 4.2266 -1.2293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2827 5.1750 -0.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4212 5.9034 -0.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6959 5.8575 2.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1198 3.2174 2.1406 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7575 0.9665 -0.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8828 -0.2272 1.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8095 -2.4295 1.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7035 -3.4051 -0.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9333 -0.6757 -1.5064 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0065 -2.3617 -3.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2113 -2.7003 -2.9756 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1722 -0.0637 -3.4636 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8020 -3.6986 -1.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4207 -3.0487 0.6143 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9240 0.1168 1.5771 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2296 -2.0941 -6.0691 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 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 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 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 3 43 1 0 6 1 1 0 17 7 1 0 28 21 1 0 39 32 1 0 16 11 1 0 1 44 1 0 2 45 1 0 4 46 1 0 5 47 1 0 13 48 1 0 15 49 1 0 18 50 1 0 19 51 1 0 21 52 1 6 22 53 1 6 23 54 1 1 24 55 1 6 25 56 1 1 26 57 1 0 26 58 1 0 27 59 1 0 29 60 1 0 30 61 1 0 32 62 1 6 33 63 1 1 34 64 1 1 35 65 1 6 36 66 1 6 37 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	LKZDFKLGDGSGEO-FFFMXZAGSA-N
Standard InCHI	InChI=1S/C27H30O16/c28-7-14-17(33)20(36)22(38)26(40-14)43-25-21(37)18(34)15(8-29)41-27(25)42-24-19(35)16-12(32)5-11(31)6-13(16)39-23(24)9-1-3-10(30)4-2-9/h1-6,14-15,17-18,20-22,25-34,36-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,25-,26+,27-/m1/s1
SMILES	c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	0.205 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.705 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.506 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.133	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.684	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.615	Fluc inhibitor:	0.293 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.735 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.605 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.376	Promiscuous compounds:	0.58

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.841	MDCK Permeability:	-4.825
Pgp-inhibitor:	0.0	Pgp-substrate:	0.858
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):	0.046
20% Bioavailability (F20%):	0.015	30% Bioavailability (F30%):	0.976
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	82.739%	Volume Distribution (VD):	-0.058
Fu:	15.831% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.399
BSEP inhibitor:	0.018

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:	0.01
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.01 ? 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):

1.662

Half-life (T1/2):

4.199

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.053
Human Hepatotoxicity (H-HT):	0.507	Drug-induced Liver Injury (DILI):	0.742
AMES Toxicity:	0.872	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.024	Skin Sensitization:	1.0
Carcinogencity:	0.156	Eye Corrosion:	0.0
Eye Irritation:	0.561	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.971
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.246
Genotoxicity:	0.903	RPMI-8226 Immunitoxicity:	0.065
A549 Cytotoxicity:	0.378	Hek293 Cytotoxicity:	0.544
BCF:	0.355 ? 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:	2.829 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.386 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.521 ? 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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37111302]
NPO17609	Thevetia neriifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17609	Thevetia neriifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO17609	Thevetia neriifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17609	Thevetia neriifolia	Species	Apocynaceae	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

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

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 NPC304769 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	24120
0.1-0.2	21324
0.2-0.3	3403
0.3-0.4	537
0.4-0.5	212
0.5-0.6	82
0.6-0.7	74
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC170052
1.0	High Similarity	NPC135846
0.9211	High Similarity	NPC163242
0.9211	High Similarity	NPC272068
0.9067	High Similarity	NPC254855
0.9067	High Similarity	NPC94610
0.8608	High Similarity	NPC304741
0.8481	Intermediate Similarity	NPC470405
0.8375	Intermediate Similarity	NPC155877
0.8205	Intermediate Similarity	NPC476215
0.8023	Intermediate Similarity	NPC602448
0.7949	Intermediate Similarity	NPC224530
0.7907	Intermediate Similarity	NPC292929
0.7831	Intermediate Similarity	NPC255157
0.7831	Intermediate Similarity	NPC259896
0.7791	Intermediate Similarity	NPC220173
0.7763	Intermediate Similarity	NPC77672
0.7763	Intermediate Similarity	NPC133671
0.7763	Intermediate Similarity	NPC135391
0.7763	Intermediate Similarity	NPC78263
0.7763	Intermediate Similarity	NPC250069
0.7586	Intermediate Similarity	NPC76831
0.7561	Intermediate Similarity	NPC473682
0.747	Intermediate Similarity	NPC139320
0.7442	Intermediate Similarity	NPC12013
0.7442	Intermediate Similarity	NPC11432
0.7442	Intermediate Similarity	NPC477613
0.7439	Intermediate Similarity	NPC95866
0.7412	Intermediate Similarity	NPC470444
0.7356	Intermediate Similarity	NPC35119
0.7326	Intermediate Similarity	NPC240306
0.7283	Intermediate Similarity	NPC219043
0.7159	Intermediate Similarity	NPC32641
0.7159	Intermediate Similarity	NPC256188
0.7143	Intermediate Similarity	NPC288084
0.7126	Intermediate Similarity	NPC61904
0.7	Intermediate Similarity	NPC145038
0.7	Intermediate Similarity	NPC56077
0.7	Intermediate Similarity	NPC281131
0.7	Intermediate Similarity	NPC64305
0.7	Intermediate Similarity	NPC253662
0.7	Intermediate Similarity	NPC179950
0.7	Intermediate Similarity	NPC88789
0.7	Intermediate Similarity	NPC491374
0.6988	Remote Similarity	NPC136761
0.6931	Remote Similarity	NPC25946
0.6923	Remote Similarity	NPC221342
0.6923	Remote Similarity	NPC476470
0.6915	Remote Similarity	NPC48984
0.686	Remote Similarity	NPC29958
0.6829	Remote Similarity	NPC216496
0.6829	Remote Similarity	NPC472459
0.6782	Remote Similarity	NPC471748
0.6778	Remote Similarity	NPC122467
0.675	Remote Similarity	NPC111929
0.675	Remote Similarity	NPC320283
0.675	Remote Similarity	NPC41121
0.6667	Remote Similarity	NPC470712
0.6556	Remote Similarity	NPC253521
0.6556	Remote Similarity	NPC64425
0.6556	Remote Similarity	NPC113836
0.6548	Remote Similarity	NPC60735
0.6548	Remote Similarity	NPC26230
0.6526	Remote Similarity	NPC203145
0.6517	Remote Similarity	NPC156869
0.6512	Remote Similarity	NPC203050
0.6512	Remote Similarity	NPC225434
0.65	Remote Similarity	NPC480445
0.6471	Remote Similarity	NPC120099
0.6463	Remote Similarity	NPC19388
0.6463	Remote Similarity	NPC240431
0.6463	Remote Similarity	NPC55786
0.6458	Remote Similarity	NPC189564
0.642	Remote Similarity	NPC67037
0.642	Remote Similarity	NPC255615
0.64	Remote Similarity	NPC488734
0.64	Remote Similarity	NPC488735
0.64	Remote Similarity	NPC488739
0.64	Remote Similarity	NPC488732
0.64	Remote Similarity	NPC488738
0.6381	Remote Similarity	NPC21359
0.6381	Remote Similarity	NPC460984
0.6364	Remote Similarity	NPC470718
0.6354	Remote Similarity	NPC89052
0.6327	Remote Similarity	NPC25523
0.6292	Remote Similarity	NPC471079
0.6279	Remote Similarity	NPC259957
0.6279	Remote Similarity	NPC609478
0.625	Remote Similarity	NPC192539
0.6235	Remote Similarity	NPC325555
0.6235	Remote Similarity	NPC226304
0.6222	Remote Similarity	NPC173582
0.6222	Remote Similarity	NPC265885
0.6222	Remote Similarity	NPC181465
0.6222	Remote Similarity	NPC215710
0.6222	Remote Similarity	NPC473438
0.6222	Remote Similarity	NPC253788
0.619	Remote Similarity	NPC297987
0.6176	Remote Similarity	NPC470713
0.6173	Remote Similarity	NPC54802
0.6173	Remote Similarity	NPC197304
0.6162	Remote Similarity	NPC303694
0.6154	Remote Similarity	NPC488737
0.6154	Remote Similarity	NPC605592
0.6118	Remote Similarity	NPC488080
0.6118	Remote Similarity	NPC169977
0.6105	Remote Similarity	NPC473071
0.6105	Remote Similarity	NPC89127
0.6071	Remote Similarity	NPC127546
0.6071	Remote Similarity	NPC57625
0.6071	Remote Similarity	NPC173637
0.6071	Remote Similarity	NPC317489
0.6071	Remote Similarity	NPC223424
0.6071	Remote Similarity	NPC600591
0.6058	Remote Similarity	NPC480444
0.6	Remote Similarity	NPC8573
0.6	Remote Similarity	NPC8856
0.6	Remote Similarity	NPC142142
0.5978	Remote Similarity	NPC65003
0.5977	Remote Similarity	NPC159579
0.5977	Remote Similarity	NPC48093
0.5962	Remote Similarity	NPC488740
0.5962	Remote Similarity	NPC488736
0.5962	Remote Similarity	NPC488733
0.596	Remote Similarity	NPC488075
0.5957	Remote Similarity	NPC297503
0.5904	Remote Similarity	NPC34531
0.59	Remote Similarity	NPC292019
0.59	Remote Similarity	NPC202908
0.5882	Remote Similarity	NPC104677
0.5843	Remote Similarity	NPC116458
0.5843	Remote Similarity	NPC246943
0.5842	Remote Similarity	NPC164704
0.5833	Remote Similarity	NPC603079
0.5818	Remote Similarity	NPC473554
0.5795	Remote Similarity	NPC175107
0.5789	Remote Similarity	NPC480471
0.5789	Remote Similarity	NPC488076
0.5752	Remote Similarity	NPC249560
0.5747	Remote Similarity	NPC24043
0.5745	Remote Similarity	NPC129264
0.5743	Remote Similarity	NPC173837
0.5699	Remote Similarity	NPC67326
0.5686	Remote Similarity	NPC480441
0.5684	Remote Similarity	NPC470125
0.5676	Remote Similarity	NPC103342
0.5667	Remote Similarity	NPC223747
0.5657	Remote Similarity	NPC218161
0.5644	Remote Similarity	NPC473072
0.5638	Remote Similarity	NPC203259
0.5638	Remote Similarity	NPC33054
0.5638	Remote Similarity	NPC176740
0.5638	Remote Similarity	NPC471725
0.5638	Remote Similarity	NPC134532
0.5638	Remote Similarity	NPC602582
0.5618	Remote Similarity	NPC219904
0.5618	Remote Similarity	NPC129217
0.56	Remote Similarity	NPC14187
0.5581	Remote Similarity	NPC135599
0.5581	Remote Similarity	NPC73855
0.5581	Remote Similarity	NPC113968
0.5581	Remote Similarity	NPC328940
0.5581	Remote Similarity	NPC277174
0.5581	Remote Similarity	NPC606877
0.5579	Remote Similarity	NPC115674
0.5579	Remote Similarity	NPC35167
0.5567	Remote Similarity	NPC270448
0.5556	Remote Similarity	NPC85707
0.5543	Remote Similarity	NPC116864
0.5543	Remote Similarity	NPC244776
0.5536	Remote Similarity	NPC231787
0.5534	Remote Similarity	NPC470715
0.5529	Remote Similarity	NPC276222
0.5529	Remote Similarity	NPC274618
0.5529	Remote Similarity	NPC118284
0.5529	Remote Similarity	NPC608147
0.5517	Remote Similarity	NPC289667
0.5517	Remote Similarity	NPC143851
0.5514	Remote Similarity	NPC162394
0.5514	Remote Similarity	NPC470717
0.551	Remote Similarity	NPC221288
0.551	Remote Similarity	NPC194836
0.551	Remote Similarity	NPC91493
0.551	Remote Similarity	NPC605081
0.5506	Remote Similarity	NPC42773
0.5506	Remote Similarity	NPC21100
0.5506	Remote Similarity	NPC45522
0.5463	Remote Similarity	NPC470720
0.5455	Remote Similarity	NPC85751
0.5455	Remote Similarity	NPC265530
0.5455	Remote Similarity	NPC471669
0.5455	Remote Similarity	NPC136042
0.5455	Remote Similarity	NPC19240
0.5444	Remote Similarity	NPC191306
0.5413	Remote Similarity	NPC209550
0.5385	Remote Similarity	NPC197285
0.5385	Remote Similarity	NPC601710
0.5361	Remote Similarity	NPC296018
0.5354	Remote Similarity	NPC205824
0.5354	Remote Similarity	NPC97119

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC304769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6193
0.1-0.2	2869
0.2-0.3	76
0.3-0.4	7
0.4-0.5	4
0.5-0.6	1
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
0.5638	Remote Similarity	NPD6797	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