NPASS Compound

Natural Product: NPC11965

Natural Product ID	NPC11965
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FRCCTBPYYAMKIB-PVVPWINYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44259028
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 81 85 0 0 0 0 0 0 0 0999 V2000 8.8886 -1.7953 0.6386 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2666 -0.6855 -0.2343 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8461 0.6410 0.1228 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9728 1.7200 -0.4950 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6239 1.5723 0.1546 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0759 0.1821 -0.0013 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9376 -0.7990 -0.3474 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2384 -0.1420 1.0787 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8818 -0.3716 1.0597 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2304 -0.6624 2.2731 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8773 -0.9008 2.3218 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0932 -0.8691 1.1997 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6958 -0.5887 -0.0048 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0699 -0.3477 -0.0427 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9622 -0.5576 -1.0716 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3506 -0.7754 -1.1122 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0100 -0.6995 -2.4414 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2611 -1.1668 -2.6997 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8140 -1.0173 -3.9525 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1538 -0.4036 -4.9945 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8849 0.0597 -4.7021 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3136 -0.0754 -3.4678 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7367 -0.2675 -6.2478 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0043 -1.0500 0.0339 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2662 -1.1017 1.2266 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8151 -1.3557 2.3252 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3662 -1.2817 0.1740 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2223 -0.2076 0.5394 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5366 -0.2047 -0.1535 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2423 1.0766 0.3037 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5162 1.8020 1.3850 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8947 0.9047 2.4086 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6511 1.5788 2.9438 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5370 -0.3290 1.9224 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4814 2.5920 2.0585 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5716 0.8366 0.7113 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6526 1.3653 0.0190 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3762 2.0676 -0.9905 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0542 1.1528 0.3943 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3677 -1.2982 0.2870 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9514 -2.1850 -0.6012 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7734 -2.0655 -1.8415 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8116 -3.3138 -0.1399 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2996 -1.1832 3.5665 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7668 1.9130 1.5147 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5102 2.9693 -0.2069 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8475 0.7588 1.5199 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7082 -1.5632 1.6916 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4328 -2.7446 0.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9814 -1.7715 0.3993 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7009 -0.9239 -1.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9047 0.7384 -0.2016 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8907 1.5321 -1.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9566 2.3514 -0.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3612 0.2727 -0.8919 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8640 -0.6858 3.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4723 -0.1364 -1.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8172 -1.6782 -1.9393 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8205 -1.3845 -4.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3253 0.5557 -5.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7026 0.3037 -3.2569 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5630 0.3155 -6.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7529 0.7826 0.4686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5082 -0.2654 -1.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2801 1.7284 -0.6174 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7845 2.5384 0.9724 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6035 0.7215 3.2558 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2682 1.0847 3.8618 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9120 2.6534 3.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9058 1.5988 2.1304 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0562 2.9667 1.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2395 1.2859 1.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6845 1.9132 -0.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4544 0.1696 0.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6461 -4.2132 -0.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8965 -3.0775 -0.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5655 -3.6320 0.8972 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6609 -1.9099 4.1747 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5991 1.1022 2.0367 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7687 3.5662 0.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6115 0.3140 1.9372 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 16 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 31 35 1 0 30 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 29 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 11 44 1 0 5 45 1 0 4 46 1 0 3 47 1 0 7 2 1 0 14 9 1 0 22 17 1 0 34 28 1 0 25 12 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 3 52 1 6 4 53 1 0 5 54 1 6 6 55 1 6 10 56 1 0 14 57 1 0 18 58 1 0 19 59 1 0 21 60 1 0 22 61 1 0 23 62 1 0 28 63 1 1 29 64 1 6 30 65 1 0 31 66 1 6 32 67 1 0 33 68 1 0 33 69 1 0 33 70 1 0 35 71 1 0 39 72 1 0 39 73 1 0 39 74 1 0 43 75 1 0 43 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 46 80 1 0 47 81 1 0 M END

Standard InCHIKey	FRCCTBPYYAMKIB-PVVPWINYSA-N
Standard InCHI	InChI=1S/C31H34O16/c1-11-21(36)24(39)25(40)30(41-11)45-17-9-18(35)20-19(10-17)46-26(15-5-7-16(34)8-6-15)28(23(20)38)47-31-29(44-14(4)33)27(43-13(3)32)22(37)12(2)42-31/h5-12,21-22,24-25,27,29-31,34-37,39-40H,1-4H3/t11?,12?,21-,22-,24?,25-,27?,29-,30-,31-/m0/s1
SMILES	CC1[C@@H](C([C@@H]([C@@H](O1)Oc1cc(c2c(c1)oc(c1ccc(cc1)O)c(c2=O)O[C@H]1[C@H](C([C@H](C(C)O1)O)OC(=O)C)OC(=O)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	662.18	Volume:	616.229 ? Van der Waals volume.
Dense:	1.075	LogP:	0.575 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.137 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.561 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	32.0
TPSA:	241.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.188	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.833	Fsp³:	0.452
MCE-18:	124.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.727	Fluc inhibitor:	0.144 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.934 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.723 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.124	Promiscuous compounds:	0.34

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.064	MDCK Permeability:	-5.156
Pgp-inhibitor:	0.0	Pgp-substrate:	0.998
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):	0.048
20% Bioavailability (F20%):	0.156	30% Bioavailability (F30%):	0.958
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.726
Plasma Protein Binding (PPB):	74.874%	Volume Distribution (VD):	-0.009
Fu:	26.065% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.955
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.33
BSEP inhibitor:	0.504

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:	0.045
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.27
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.406 ? 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):

2.344

Half-life (T1/2):

3.235

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.17
Human Hepatotoxicity (H-HT):	0.752	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.905	Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.157	Skin Sensitization:	0.996
Carcinogencity:	0.062	Eye Corrosion:	0.0
Eye Irritation:	0.033	Respiratory Toxicity:	0.02
Drug-induced Neurotoxicity:	0.03	Ototoxicity:	0.892
Hematotoxicity:	0.262	Drug-induced Nephrotoxicity:	0.468
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.117
A549 Cytotoxicity:	0.583	Hek293 Cytotoxicity:	0.506
BCF:	0.482 ? 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:	3.169 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.719 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.002 ? 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
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[12951487]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16870425]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24013342]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	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 NPC11965 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	17751
0.1-0.2	28933
0.2-0.3	2376
0.3-0.4	356
0.4-0.5	288
0.5-0.6	106
0.6-0.7	26
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	Natural Product ID
0.7875	Intermediate Similarity	NPC249281
0.747	Intermediate Similarity	NPC46420
0.7442	Intermediate Similarity	NPC276377
0.7326	Intermediate Similarity	NPC116458
0.7326	Intermediate Similarity	NPC246943
0.7097	Intermediate Similarity	NPC72016
0.7093	Intermediate Similarity	NPC48093
0.7065	Intermediate Similarity	NPC64425
0.7033	Intermediate Similarity	NPC150164
0.6957	Remote Similarity	NPC186816
0.6915	Remote Similarity	NPC32641
0.6915	Remote Similarity	NPC256188
0.6915	Remote Similarity	NPC35119
0.6744	Remote Similarity	NPC297987
0.6667	Remote Similarity	NPC271692
0.6562	Remote Similarity	NPC606657
0.6556	Remote Similarity	NPC605784
0.6517	Remote Similarity	NPC611303
0.6364	Remote Similarity	NPC298171
0.6322	Remote Similarity	NPC111929
0.6322	Remote Similarity	NPC320283
0.6322	Remote Similarity	NPC331652
0.6322	Remote Similarity	NPC41121
0.6311	Remote Similarity	NPC25523
0.6296	Remote Similarity	NPC138990
0.625	Remote Similarity	NPC108831
0.625	Remote Similarity	NPC182634
0.6186	Remote Similarity	NPC240306
0.618	Remote Similarity	NPC158674
0.617	Remote Similarity	NPC251417
0.6162	Remote Similarity	NPC142142
0.6078	Remote Similarity	NPC14187
0.6067	Remote Similarity	NPC289667
0.6	Remote Similarity	NPC136042
0.6	Remote Similarity	NPC164704
0.5922	Remote Similarity	NPC470455
0.5889	Remote Similarity	NPC19709
0.5889	Remote Similarity	NPC238376
0.587	Remote Similarity	NPC216496
0.5842	Remote Similarity	NPC101399
0.5842	Remote Similarity	NPC217822
0.5842	Remote Similarity	NPC11847
0.5842	Remote Similarity	NPC198938
0.5806	Remote Similarity	NPC159579
0.5804	Remote Similarity	NPC175429
0.58	Remote Similarity	NPC483414
0.58	Remote Similarity	NPC483415
0.5761	Remote Similarity	NPC84362
0.5743	Remote Similarity	NPC483416
0.5714	Remote Similarity	NPC127546
0.5714	Remote Similarity	NPC121703
0.5714	Remote Similarity	NPC57625
0.5714	Remote Similarity	NPC173637
0.5714	Remote Similarity	NPC317489
0.5714	Remote Similarity	NPC223424
0.5714	Remote Similarity	NPC600591
0.5701	Remote Similarity	NPC480441
0.5701	Remote Similarity	NPC470715
0.5676	Remote Similarity	NPC470717
0.5638	Remote Similarity	NPC129217
0.5631	Remote Similarity	NPC188815
0.5625	Remote Similarity	NPC476215
0.5596	Remote Similarity	NPC470716
0.5591	Remote Similarity	NPC27640
0.5579	Remote Similarity	NPC259957
0.5577	Remote Similarity	NPC101636
0.5556	Remote Similarity	NPC173582
0.5556	Remote Similarity	NPC44931
0.5556	Remote Similarity	NPC265885
0.5556	Remote Similarity	NPC181465
0.5556	Remote Similarity	NPC215710
0.5556	Remote Similarity	NPC473438
0.5556	Remote Similarity	NPC253788
0.5543	Remote Similarity	NPC348541
0.5532	Remote Similarity	NPC27942
0.5487	Remote Similarity	NPC470720
0.5439	Remote Similarity	NPC209550
0.5435	Remote Similarity	NPC473043
0.5408	Remote Similarity	NPC265115
0.5376	Remote Similarity	NPC39360
0.5376	Remote Similarity	NPC104677
0.5376	Remote Similarity	NPC77672
0.5376	Remote Similarity	NPC133671
0.5376	Remote Similarity	NPC135391
0.5376	Remote Similarity	NPC29763
0.5376	Remote Similarity	NPC78263
0.5376	Remote Similarity	NPC210003
0.5376	Remote Similarity	NPC250069
0.5368	Remote Similarity	NPC59534
0.5361	Remote Similarity	NPC223747
0.5319	Remote Similarity	NPC323593
0.5319	Remote Similarity	NPC203500
0.5312	Remote Similarity	NPC219904
0.5306	Remote Similarity	NPC66087
0.5269	Remote Similarity	NPC135599
0.5269	Remote Similarity	NPC73855
0.5269	Remote Similarity	NPC113968
0.5269	Remote Similarity	NPC328940
0.5269	Remote Similarity	NPC277174
0.5269	Remote Similarity	NPC606877
0.5263	Remote Similarity	NPC305811
0.5263	Remote Similarity	NPC24043
0.5258	Remote Similarity	NPC85707
0.5258	Remote Similarity	NPC224530
0.5248	Remote Similarity	NPC163242
0.5248	Remote Similarity	NPC272068
0.5248	Remote Similarity	NPC67105
0.5221	Remote Similarity	NPC295625
0.5196	Remote Similarity	NPC65563
0.5196	Remote Similarity	NPC210073
0.5196	Remote Similarity	NPC470949
0.5192	Remote Similarity	NPC75574
0.5192	Remote Similarity	NPC12013
0.5192	Remote Similarity	NPC11432
0.5192	Remote Similarity	NPC477613
0.5189	Remote Similarity	NPC470447
0.5189	Remote Similarity	NPC483413
0.5189	Remote Similarity	NPC483412
0.5158	Remote Similarity	NPC265530
0.5152	Remote Similarity	NPC190003
0.5146	Remote Similarity	NPC473571
0.5146	Remote Similarity	NPC110941
0.514	Remote Similarity	NPC470449
0.5106	Remote Similarity	NPC160515
0.51	Remote Similarity	NPC116864
0.51	Remote Similarity	NPC244776
0.51	Remote Similarity	NPC95866
0.5094	Remote Similarity	NPC486577
0.5091	Remote Similarity	NPC189564
0.5082	Remote Similarity	NPC223860
0.506	Remote Similarity	NPC146679
0.5054	Remote Similarity	NPC288084
0.5053	Remote Similarity	NPC476405
0.5049	Remote Similarity	NPC203259
0.5049	Remote Similarity	NPC65003
0.5049	Remote Similarity	NPC33054
0.5049	Remote Similarity	NPC176740
0.5049	Remote Similarity	NPC471725
0.5049	Remote Similarity	NPC134532
0.5049	Remote Similarity	NPC602582
0.5047	Remote Similarity	NPC89127

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC11965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5264
0.1-0.2	3835
0.2-0.3	42
0.3-0.4	4
0.4-0.5	2
0.5-0.6	3
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
0.5631	Remote Similarity	NPD7251	Phase 2
0.5278	Remote Similarity	NPD7808	Phase 3
0.5049	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