NPASS Compound

Natural Product: NPC578001

Natural Product ID	NPC578001
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},3~{S},4~{R},5~{S},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-4-oxo-2-[4-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxyphenyl]chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{R},3~{S},4~{R},5~{S},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-4-oxo-2-[4-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxyphenyl]chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

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 70 74 0 0 0 0 0 0 0 0999 V2000 -8.0266 -0.8138 -2.5491 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7389 -0.0959 -1.2516 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6830 -0.9707 -0.1695 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9644 -0.2848 0.8405 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7956 0.1666 0.2531 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5118 -0.1709 0.5785 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4740 0.3929 -0.1328 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1508 0.1097 0.1272 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7909 -0.7795 1.1438 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3847 -1.0621 1.3989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0551 -1.9214 2.3764 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4245 -2.1496 2.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8562 -2.9256 3.4511 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3139 -1.4804 1.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6749 -1.6404 1.8585 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2063 -2.4886 2.8183 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5169 -0.9340 0.9914 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0487 -0.0799 0.0212 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8400 0.6347 -0.8527 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2218 0.6225 -0.9114 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7916 1.8819 -0.6900 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1131 1.6694 -0.3048 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1945 1.2511 1.1224 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1483 1.1325 1.8105 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4498 1.0012 1.6548 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7986 0.6634 -1.2074 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8910 -0.5904 -0.6531 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0622 0.6116 -2.5394 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6513 -0.2966 -3.3909 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6197 0.2329 -2.3259 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8627 1.0575 -3.1888 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6549 0.0558 -0.0633 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8185 -0.6323 0.7822 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5156 -0.4736 0.6660 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8302 -1.3409 1.8524 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1687 -1.0485 1.5825 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8835 0.8139 1.3193 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4088 1.4633 2.4430 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2594 1.7753 0.2133 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2748 2.5854 0.6925 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8237 0.9370 -0.9342 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1392 1.7097 -2.0349 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9478 -1.3989 -2.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1554 -0.0185 -3.3246 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1420 -1.4216 -2.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8059 0.4792 -1.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8467 -0.9971 1.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7201 1.0922 -0.9343 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3352 0.5551 -0.4345 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6412 -2.4298 3.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2962 -3.4839 2.6981 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5800 -1.0754 1.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6665 -0.0417 -0.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6437 2.6403 -0.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5250 0.3475 2.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8395 1.0097 -1.4325 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8170 -0.8573 -0.4093 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1456 1.6492 -2.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4625 -0.0017 -4.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3866 -0.8053 -2.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9252 0.8084 -3.2118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2676 0.7307 -0.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5757 -2.0422 2.6557 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9417 -1.5201 2.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8446 0.3042 1.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7526 2.1822 2.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3793 2.3401 -0.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2839 3.4349 0.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6963 0.3675 -0.5692 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9083 1.2826 -2.5155 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 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 15 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 22 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 18 32 1 0 32 33 2 0 33 34 1 0 9 35 1 0 35 36 2 0 4 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 2 1 0 36 6 1 0 34 10 1 0 33 14 1 0 30 20 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 6 4 47 1 1 7 48 1 0 8 49 1 0 11 50 1 0 16 51 1 0 17 52 1 0 20 53 1 1 22 54 1 1 25 55 1 0 26 56 1 6 27 57 1 0 28 58 1 6 29 59 1 0 30 60 1 6 31 61 1 0 32 62 1 0 35 63 1 0 36 64 1 0 37 65 1 1 38 66 1 0 39 67 1 6 40 68 1 0 41 69 1 1 42 70 1 0 M END

Standard InCHIKey	IYSVAHHNEAGSMC-IZAIXGGKSA-N
Standard InCHI	InChI=1S/C27H28O15/c1-9-18(30)19(31)22(34)26(38-9)39-11-4-2-10(3-5-11)15-8-14(29)17-13(28)6-12(7-16(17)41-15)40-27-23(35)20(32)21(33)24(42-27)25(36)37/h2-9,18-24,26-28,30-35H,1H3,(H,36,37)/t9-,18-,19+,20+,21-,22-,23-,24+,26-,27+/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=CC=C(C3=CC(=O)C4=C(O)C=C(O[C@@H]5O[C@@H](C(=O)O)[C@@H](O)[C@@H](O)[C@@H]5O)C=C4O3)C=C2)[C@@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	592.14	Volume:	540.891 ? Van der Waals volume.
Dense:	1.095	LogP:	1.105 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.596 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.482 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	31.0
TPSA:	246.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.165	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.628	Fsp³:	0.407
MCE-18:	119.895 ? 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:	0.513	Fluc inhibitor:	0.436 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.938 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.925 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.253	Promiscuous compounds:	0.402

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.359	MDCK Permeability:	-5.151
Pgp-inhibitor:	0.0	Pgp-substrate:	0.917
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):	0.632
20% Bioavailability (F20%):	0.148	30% Bioavailability (F30%):	0.638
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.823
Plasma Protein Binding (PPB):	81.769%	Volume Distribution (VD):	-0.11
Fu:	14.141% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.065
OATP1B3 inhibitor:	0.726	BCRP inhibitor:	0.007
BSEP inhibitor:	0.002

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:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.918
HLM stability:	0.003 ? 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):

1.227

Half-life (T1/2):

6.003

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.056
Human Hepatotoxicity (H-HT):	0.377	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.932	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.024	Skin Sensitization:	0.918
Carcinogencity:	0.02	Eye Corrosion:	0.0
Eye Irritation:	0.049	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.966
Hematotoxicity:	0.156	Drug-induced Nephrotoxicity:	0.93
Genotoxicity:	0.828	RPMI-8226 Immunitoxicity:	0.176
A549 Cytotoxicity:	0.049	Hek293 Cytotoxicity:	0.095
BCF:	0.233 ? 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:	2.972 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.315 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.475 ? 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
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33264011]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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 NPC578001 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	18164
0.1-0.2	28687
0.2-0.3	2217
0.3-0.4	527
0.4-0.5	176
0.5-0.6	59
0.6-0.7	20
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	Natural Product ID
0.825	Intermediate Similarity	NPC608742
0.7683	Intermediate Similarity	NPC282169
0.747	Intermediate Similarity	NPC20505
0.7073	Intermediate Similarity	NPC331652
0.6988	Remote Similarity	NPC19709
0.6867	Remote Similarity	NPC473043
0.6667	Remote Similarity	NPC46202
0.6512	Remote Similarity	NPC95090
0.6512	Remote Similarity	NPC27408
0.6452	Remote Similarity	NPC22062
0.6452	Remote Similarity	NPC473634
0.6452	Remote Similarity	NPC138811
0.6437	Remote Similarity	NPC181712
0.6354	Remote Similarity	NPC229409
0.6316	Remote Similarity	NPC64051
0.6263	Remote Similarity	NPC253685
0.6111	Remote Similarity	NPC237435
0.6044	Remote Similarity	NPC43211
0.6023	Remote Similarity	NPC39360
0.6023	Remote Similarity	NPC29763
0.6023	Remote Similarity	NPC210003
0.6022	Remote Similarity	NPC600989
0.6	Remote Similarity	NPC44931
0.6	Remote Similarity	NPC27942
0.5955	Remote Similarity	NPC189142
0.5955	Remote Similarity	NPC77660
0.5938	Remote Similarity	NPC210073
0.5914	Remote Similarity	NPC190003
0.59	Remote Similarity	NPC475382
0.587	Remote Similarity	NPC22832
0.587	Remote Similarity	NPC243930
0.5859	Remote Similarity	NPC209296
0.57	Remote Similarity	NPC473623
0.5699	Remote Similarity	NPC601144
0.5667	Remote Similarity	NPC261866
0.5667	Remote Similarity	NPC238376
0.5652	Remote Similarity	NPC101191
0.5644	Remote Similarity	NPC479766
0.5644	Remote Similarity	NPC488089
0.5638	Remote Similarity	NPC607707
0.5612	Remote Similarity	NPC65003
0.5591	Remote Similarity	NPC210094
0.5591	Remote Similarity	NPC611303
0.5588	Remote Similarity	NPC479765
0.5556	Remote Similarity	NPC115674
0.5556	Remote Similarity	NPC160515
0.5532	Remote Similarity	NPC115760
0.5532	Remote Similarity	NPC610187
0.5524	Remote Similarity	NPC11468
0.5495	Remote Similarity	NPC58053
0.5495	Remote Similarity	NPC249281
0.5495	Remote Similarity	NPC108831
0.5495	Remote Similarity	NPC143851
0.5495	Remote Similarity	NPC182634
0.5474	Remote Similarity	NPC311830
0.5426	Remote Similarity	NPC135277
0.54	Remote Similarity	NPC204693
0.5385	Remote Similarity	NPC101636
0.5385	Remote Similarity	NPC298171
0.5376	Remote Similarity	NPC186807
0.5376	Remote Similarity	NPC271692
0.5368	Remote Similarity	NPC80188
0.5361	Remote Similarity	NPC211594
0.534	Remote Similarity	NPC270675
0.534	Remote Similarity	NPC195685
0.5326	Remote Similarity	NPC289667
0.5312	Remote Similarity	NPC220169
0.5312	Remote Similarity	NPC605784
0.5306	Remote Similarity	NPC251417
0.5269	Remote Similarity	NPC158674
0.5229	Remote Similarity	NPC473644
0.5213	Remote Similarity	NPC46420
0.5189	Remote Similarity	NPC472994
0.5182	Remote Similarity	NPC311850
0.5179	Remote Similarity	NPC68592
0.5155	Remote Similarity	NPC116458
0.5155	Remote Similarity	NPC246943
0.5152	Remote Similarity	NPC8856
0.5152	Remote Similarity	NPC606546
0.5146	Remote Similarity	NPC65711
0.5143	Remote Similarity	NPC195257
0.5102	Remote Similarity	NPC276377
0.5062	Remote Similarity	NPC29353

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC578001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3657
0.1-0.2	5383
0.2-0.3	99
0.3-0.4	5
0.4-0.5	4
0.5-0.6	1
0.6-0.7	1
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
0.6111	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7054	Phase 4

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