NPASS Compound

Natural Product: NPC78998

Natural Product ID	NPC78998
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YOXWSUCVDVXAMX-VMJMUREYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5320832
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 74 78 0 0 0 0 0 0 0 0999 V2000 -3.6193 3.2654 -0.8408 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7754 4.0258 -0.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1934 4.7940 0.1968 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4559 4.7938 1.3374 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3212 4.0330 1.3672 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8740 3.2639 0.3144 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6563 2.5048 0.4620 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2115 1.5863 -0.4121 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0044 0.9169 -0.1937 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4681 0.0621 -0.9717 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7172 1.2035 0.9352 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1975 2.1511 1.7994 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8817 2.4662 2.9671 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0677 1.8223 3.2381 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5682 0.8817 2.3611 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9097 0.5472 1.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3796 -0.3671 0.3001 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4549 -1.2274 0.3761 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5697 -2.2322 -0.6946 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8701 -2.9828 -0.5816 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6275 -2.6863 0.6876 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6363 -1.2416 1.0456 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9599 -0.5552 0.9915 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4354 -0.2990 -0.2824 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6725 -0.4801 0.3707 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9444 -3.1279 0.5975 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6418 -2.9246 -1.7328 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4691 -3.0945 -0.7960 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7275 2.1647 4.4280 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9264 2.7628 1.5633 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8682 1.1818 -1.5826 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6852 0.0182 -1.3755 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6123 -0.2345 -2.4970 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4286 -1.5060 -2.1724 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9090 -2.0899 -0.9041 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4293 -2.1571 -0.7912 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8701 -3.4923 -1.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5140 -4.5775 -0.7136 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7741 -1.0996 -1.3880 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3869 -3.4234 -0.8276 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4663 -2.3822 -3.2452 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4774 0.7869 -2.8221 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8597 5.5612 2.4496 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3660 5.5454 0.0891 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3298 2.7388 -1.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3576 4.0139 -1.8211 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7613 4.0794 2.3134 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4628 3.2140 3.6432 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4981 0.4047 2.6177 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4794 -1.6827 1.4062 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6481 -1.6809 -1.6892 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5884 -4.0790 -0.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1696 -3.2973 1.5265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3053 -1.1723 2.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8822 0.4246 1.5239 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7392 -1.1471 1.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0552 0.5003 -0.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2324 -3.3360 1.5456 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0924 -2.5226 -2.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1613 -3.0857 -1.7531 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4134 2.9018 4.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0635 0.0034 -0.3597 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9918 -0.4904 -3.4264 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4786 -1.1207 -1.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3303 -1.5875 0.0052 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1550 -2.1065 0.3013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8704 -3.5644 -2.3751 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7928 -3.4968 -0.9723 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9083 -4.9842 -0.0272 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2336 -3.4460 -0.2655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3368 -2.8557 -3.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6680 0.7919 -3.8100 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4136 6.4682 2.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5503 5.9568 -0.8319 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 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 14 29 1 0 12 30 1 0 8 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 4 43 1 0 3 44 1 0 6 1 1 0 30 7 1 0 39 32 1 0 16 11 1 0 25 18 1 0 1 45 1 0 2 46 1 0 5 47 1 0 13 48 1 0 15 49 1 0 18 50 1 1 19 51 1 6 20 52 1 1 21 53 1 1 22 54 1 1 23 55 1 0 23 56 1 0 24 57 1 0 26 58 1 0 27 59 1 0 28 60 1 0 29 61 1 0 32 62 1 1 33 63 1 6 34 64 1 1 35 65 1 1 36 66 1 1 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 44 74 1 0 M END

Standard InCHIKey	YOXWSUCVDVXAMX-VMJMUREYSA-N
Standard InCHI	InChI=1S/C27H30O17/c28-6-14-17(33)20(36)22(38)26(42-14)41-13-5-9(30)4-12-16(13)19(35)25(24(40-12)8-1-2-10(31)11(32)3-8)44-27-23(39)21(37)18(34)15(7-29)43-27/h1-5,14-15,17-18,20-23,26-34,36-39H,6-7H2/t14-,15-,17+,18+,20+,21+,22-,23-,26-,27+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)O)o1)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	626.15	Volume:	561.108 ? Van der Waals volume.
Dense:	1.116	LogP:	-0.061 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.686 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.11 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	289.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.116	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.795	Fsp³:	0.444
MCE-18:	122.949 ? 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:	0.646	Fluc inhibitor:	0.279 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.733 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.588 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.305	Promiscuous compounds:	0.599

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.694	MDCK Permeability:	-4.93
Pgp-inhibitor:	0.0	Pgp-substrate:	0.114
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):	0.998
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.631
Plasma Protein Binding (PPB):	80.38%	Volume Distribution (VD):	-0.075
Fu:	18.806% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.946
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

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:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.212 ? 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):

1.975

Half-life (T1/2):

4.098

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.039
Human Hepatotoxicity (H-HT):	0.829	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.022	Skin Sensitization:	1.0
Carcinogencity:	0.201	Eye Corrosion:	0.0
Eye Irritation:	0.155	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.984
Hematotoxicity:	0.458	Drug-induced Nephrotoxicity:	0.447
Genotoxicity:	0.983	RPMI-8226 Immunitoxicity:	0.08
A549 Cytotoxicity:	0.995	Hek293 Cytotoxicity:	0.809
BCF:	0.336 ? 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:	2.819 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.607 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.569 ? 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
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	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 NPC78998 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	19271
0.1-0.2	26527
0.2-0.3	2890
0.3-0.4	686
0.4-0.5	283
0.5-0.6	121
0.6-0.7	51
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9275	High Similarity	NPC599850
0.7945	Intermediate Similarity	NPC609879
0.7703	Intermediate Similarity	NPC145038
0.7703	Intermediate Similarity	NPC56077
0.7703	Intermediate Similarity	NPC281131
0.7703	Intermediate Similarity	NPC253662
0.7703	Intermediate Similarity	NPC179950
0.7703	Intermediate Similarity	NPC88789
0.7703	Intermediate Similarity	NPC491374
0.7284	Intermediate Similarity	NPC476773
0.7237	Intermediate Similarity	NPC136042
0.7105	Intermediate Similarity	NPC83283
0.7051	Intermediate Similarity	NPC42773
0.7051	Intermediate Similarity	NPC45522
0.7	Intermediate Similarity	NPC605784
0.6883	Remote Similarity	NPC77672
0.6883	Remote Similarity	NPC133671
0.6883	Remote Similarity	NPC135391
0.6883	Remote Similarity	NPC78263
0.6883	Remote Similarity	NPC250069
0.6842	Remote Similarity	NPC67037
0.6842	Remote Similarity	NPC255615
0.6786	Remote Similarity	NPC471748
0.675	Remote Similarity	NPC488071
0.6709	Remote Similarity	NPC84362
0.6667	Remote Similarity	NPC127546
0.6667	Remote Similarity	NPC19388
0.6667	Remote Similarity	NPC240431
0.6667	Remote Similarity	NPC57625
0.6667	Remote Similarity	NPC55786
0.6667	Remote Similarity	NPC173637
0.6667	Remote Similarity	NPC317489
0.6667	Remote Similarity	NPC223424
0.6667	Remote Similarity	NPC600591
0.6582	Remote Similarity	NPC297987
0.6512	Remote Similarity	NPC156869
0.6471	Remote Similarity	NPC29958
0.6386	Remote Similarity	NPC116458
0.6386	Remote Similarity	NPC246943
0.6375	Remote Similarity	NPC64305
0.6341	Remote Similarity	NPC60735
0.6341	Remote Similarity	NPC26230
0.631	Remote Similarity	NPC203050
0.631	Remote Similarity	NPC225434
0.6296	Remote Similarity	NPC488080
0.6296	Remote Similarity	NPC169977
0.6279	Remote Similarity	NPC480466
0.6265	Remote Similarity	NPC120099
0.622	Remote Similarity	NPC222936
0.622	Remote Similarity	NPC472459
0.619	Remote Similarity	NPC206123
0.6145	Remote Similarity	NPC175107
0.6098	Remote Similarity	NPC305811
0.6098	Remote Similarity	NPC24043
0.6098	Remote Similarity	NPC271692
0.6092	Remote Similarity	NPC139320
0.6076	Remote Similarity	NPC288084
0.6049	Remote Similarity	NPC289667
0.6047	Remote Similarity	NPC254855
0.6047	Remote Similarity	NPC116864
0.6047	Remote Similarity	NPC244776
0.6047	Remote Similarity	NPC94610
0.6024	Remote Similarity	NPC325555
0.6024	Remote Similarity	NPC226304
0.6	Remote Similarity	NPC488073
0.6	Remote Similarity	NPC149127
0.5976	Remote Similarity	NPC277205
0.5976	Remote Similarity	NPC37919
0.5955	Remote Similarity	NPC605592
0.5926	Remote Similarity	NPC111929
0.5926	Remote Similarity	NPC320283
0.5926	Remote Similarity	NPC41121
0.5904	Remote Similarity	NPC27640
0.5882	Remote Similarity	NPC101026
0.5882	Remote Similarity	NPC488077
0.5882	Remote Similarity	NPC609478
0.5876	Remote Similarity	NPC292019
0.5876	Remote Similarity	NPC202908
0.5875	Remote Similarity	NPC34531
0.5795	Remote Similarity	NPC251417
0.5783	Remote Similarity	NPC8573
0.5783	Remote Similarity	NPC189142
0.5783	Remote Similarity	NPC77660
0.5778	Remote Similarity	NPC203259
0.5778	Remote Similarity	NPC33054
0.5778	Remote Similarity	NPC155877
0.5778	Remote Similarity	NPC176740
0.5778	Remote Similarity	NPC471725
0.5778	Remote Similarity	NPC134532
0.5778	Remote Similarity	NPC602582
0.5732	Remote Similarity	NPC135599
0.5732	Remote Similarity	NPC73855
0.5732	Remote Similarity	NPC113968
0.5732	Remote Similarity	NPC328940
0.5732	Remote Similarity	NPC277174
0.5732	Remote Similarity	NPC606877
0.5729	Remote Similarity	NPC14187
0.5714	Remote Similarity	NPC245014
0.5679	Remote Similarity	NPC276222
0.5679	Remote Similarity	NPC274618
0.5679	Remote Similarity	NPC118284
0.5679	Remote Similarity	NPC608147
0.5667	Remote Similarity	NPC67326
0.5663	Remote Similarity	NPC249281
0.5652	Remote Similarity	NPC64425
0.5647	Remote Similarity	NPC59534
0.5647	Remote Similarity	NPC117260
0.5595	Remote Similarity	NPC282987
0.5595	Remote Similarity	NPC168822
0.5568	Remote Similarity	NPC488072
0.5529	Remote Similarity	NPC58716
0.5529	Remote Similarity	NPC46420
0.5529	Remote Similarity	NPC45638
0.5529	Remote Similarity	NPC610763
0.55	Remote Similarity	NPC480441
0.5465	Remote Similarity	NPC201292
0.5455	Remote Similarity	NPC223747
0.5444	Remote Similarity	NPC480463
0.5417	Remote Similarity	NPC471669
0.5412	Remote Similarity	NPC323593
0.5412	Remote Similarity	NPC203500
0.5402	Remote Similarity	NPC219904
0.5402	Remote Similarity	NPC479401
0.5393	Remote Similarity	NPC170052
0.5393	Remote Similarity	NPC135846
0.5376	Remote Similarity	NPC255157
0.5376	Remote Similarity	NPC259896
0.5368	Remote Similarity	NPC37668
0.5368	Remote Similarity	NPC35119
0.5349	Remote Similarity	NPC52550
0.5341	Remote Similarity	NPC21666
0.5333	Remote Similarity	NPC95866
0.5333	Remote Similarity	NPC265115
0.5319	Remote Similarity	NPC126784
0.5319	Remote Similarity	NPC241423
0.5319	Remote Similarity	NPC488074
0.5312	Remote Similarity	NPC64755
0.53	Remote Similarity	NPC189564
0.5294	Remote Similarity	NPC39360
0.5294	Remote Similarity	NPC29763
0.5294	Remote Similarity	NPC210003
0.5263	Remote Similarity	NPC483415
0.5233	Remote Similarity	NPC265530
0.5233	Remote Similarity	NPC158674
0.5227	Remote Similarity	NPC235260
0.5227	Remote Similarity	NPC159579
0.5227	Remote Similarity	NPC168584
0.5227	Remote Similarity	NPC155763
0.5222	Remote Similarity	NPC276377
0.5208	Remote Similarity	NPC32641
0.5208	Remote Similarity	NPC256188
0.5172	Remote Similarity	NPC84265
0.5169	Remote Similarity	NPC197285
0.5169	Remote Similarity	NPC601710
0.5161	Remote Similarity	NPC173582
0.5161	Remote Similarity	NPC470405
0.5161	Remote Similarity	NPC265885
0.5161	Remote Similarity	NPC181465
0.5161	Remote Similarity	NPC215710
0.5161	Remote Similarity	NPC163242
0.5161	Remote Similarity	NPC272068
0.5161	Remote Similarity	NPC473438
0.5161	Remote Similarity	NPC253788
0.5152	Remote Similarity	NPC470446
0.5152	Remote Similarity	NPC223426
0.5116	Remote Similarity	NPC112755
0.5116	Remote Similarity	NPC170675
0.5116	Remote Similarity	NPC238376
0.5116	Remote Similarity	NPC143851
0.5114	Remote Similarity	NPC21100
0.5106	Remote Similarity	NPC150164
0.5104	Remote Similarity	NPC470443
0.5104	Remote Similarity	NPC483414
0.5102	Remote Similarity	NPC76831
0.51	Remote Similarity	NPC81042
0.5098	Remote Similarity	NPC219043
0.5057	Remote Similarity	NPC93337
0.5057	Remote Similarity	NPC146792
0.5057	Remote Similarity	NPC259152
0.5056	Remote Similarity	NPC191306
0.5056	Remote Similarity	NPC182121
0.5056	Remote Similarity	NPC611303
0.5054	Remote Similarity	NPC471079
0.5052	Remote Similarity	NPC483416
0.5051	Remote Similarity	NPC470445
0.505	Remote Similarity	NPC203145
0.5049	Remote Similarity	NPC25523

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC78998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5319
0.1-0.2	3742
0.2-0.3	76
0.3-0.4	7
0.4-0.5	4
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
0.5778	Remote Similarity	NPD6797	Phase 2
0.5258	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