NPASS Compound

Natural Product: NPC262451

Natural Product ID	NPC262451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RLGRBYHBNWLGER-NDWMXOAQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11972315
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 86 89 0 0 0 0 0 0 0 0999 V2000 3.4417 -2.8056 -0.7317 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7908 -3.3687 -1.9776 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1136 -4.6562 -1.6042 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9592 -4.9905 -2.4943 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0305 -3.8572 -2.4875 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6474 -2.6235 -1.9671 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9035 -2.4412 -2.5205 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1492 -1.4933 -2.1202 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5302 -0.9051 -0.9223 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0043 -1.0249 -0.7456 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7825 0.2401 -0.7545 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9304 0.1997 -1.5352 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0769 0.6230 -0.9278 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5182 -0.1263 0.2834 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7930 0.5286 0.7461 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0358 0.1581 0.2983 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1828 0.7845 0.7603 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1143 1.8019 1.6846 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8846 2.1889 2.1458 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7530 1.5604 1.6810 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8077 3.2193 3.0848 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5621 3.6589 3.5945 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2720 2.4226 2.1392 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0334 1.3184 -1.2751 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9215 1.5431 -0.4309 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3282 2.8773 -0.8835 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2676 3.9009 -0.7569 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0687 0.4444 -0.7959 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2082 0.5067 0.0551 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4556 0.8934 -0.3390 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6518 1.2177 -1.5146 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6026 0.9445 0.5901 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7994 1.3250 0.1847 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9774 1.4029 1.0316 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9773 1.0747 2.3660 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1144 1.1677 3.1438 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2741 1.5933 2.5942 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3210 1.9387 1.2383 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1669 1.8336 0.4905 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5256 2.3676 0.7235 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6230 2.7325 -0.6473 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4269 1.6933 3.3583 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3444 -1.8035 0.3737 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0984 -4.2182 -1.6639 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3248 -6.1756 -2.1047 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8057 -4.7340 -0.2583 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2297 -3.5448 -0.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8431 -1.7962 -0.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6691 -2.8795 0.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6237 -3.5977 -2.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8711 -5.4837 -1.7702 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3148 -5.1030 -3.5563 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3875 -3.6422 -3.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7731 -2.7610 -0.8717 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0643 -1.5374 -0.1067 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4107 -1.6403 -1.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0664 0.5833 0.2619 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9505 1.6933 -0.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8923 0.5355 -1.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7335 -1.1923 0.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8042 0.0286 1.1412 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1281 -0.6316 -0.4242 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1507 0.4737 0.3926 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8057 1.8813 2.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7195 4.5854 4.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8390 3.8702 2.7600 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1096 2.8627 4.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3214 3.4359 2.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1850 1.5598 0.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5363 3.1641 -0.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0494 2.8182 -1.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0170 3.8139 -1.3980 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4602 0.7768 -1.8060 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4684 0.6717 1.6118 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8764 1.5966 -0.8840 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0537 0.7312 2.8184 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0086 0.8798 4.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2673 2.1169 -0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6021 3.2298 -0.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7786 3.4427 -0.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5302 1.8241 -1.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3099 1.7244 2.8724 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9079 -1.3643 1.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8602 -4.4275 -2.2499 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3102 -5.9579 -1.3969 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7380 -5.6785 0.0128 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 21 22 1 0 18 23 1 0 11 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 37 42 1 0 10 43 1 0 5 44 1 0 4 45 1 0 3 46 1 0 7 2 1 0 28 9 1 0 39 34 1 0 20 15 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 6 3 51 1 1 4 52 1 6 5 53 1 6 6 54 1 1 9 55 1 1 10 56 1 6 11 57 1 1 13 58 1 0 13 59 1 0 14 60 1 0 14 61 1 0 16 62 1 0 17 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 25 69 1 1 26 70 1 0 26 71 1 0 27 72 1 0 28 73 1 6 32 74 1 0 33 75 1 0 35 76 1 0 36 77 1 0 39 78 1 0 41 79 1 0 41 80 1 0 41 81 1 0 42 82 1 0 43 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 M END

Standard InCHIKey	RLGRBYHBNWLGER-NDWMXOAQSA-N
Standard InCHI	InChI=1S/C31H40O15/c1-15-24(36)25(37)26(38)31(43-15)46-29-27(39)30(42-11-10-17-5-8-19(34)21(13-17)41-3)44-22(14-32)28(29)45-23(35)9-6-16-4-7-18(33)20(12-16)40-2/h4-9,12-13,15,22,24-34,36-39H,10-11,14H2,1-3H3/b9-6+/t15-,22+,24+,25+,26+,27+,28+,29+,30+,31-/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)OC)O)O[C@H](CO)[C@H]1OC(=O)/C=C/c1ccc(c(c1)OC)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.24	Volume:	621.268 ? Van der Waals volume.
Dense:	1.05	LogP:	0.479 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.097 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.53 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	26.0
TPSA:	223.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.114	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.667	Fsp³:	0.516
MCE-18:	99.34 ? 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:	0
Colloidal aggregators:	0.757	Fluc inhibitor:	0.665 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.157 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.521 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.081	Promiscuous compounds:	0.283

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.225	MDCK Permeability:	-5.415
Pgp-inhibitor:	0.002	Pgp-substrate:	0.918
PAMPA:	0.997 ? 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):	0.126
20% Bioavailability (F20%):	0.5	30% Bioavailability (F30%):	0.895
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.047
Plasma Protein Binding (PPB):	69.56%	Volume Distribution (VD):	-0.353
Fu:	30.133% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.011
BSEP inhibitor:	0.658

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.258	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.213 ? 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):

2.534

Half-life (T1/2):

3.718

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.287
Human Hepatotoxicity (H-HT):	0.269	Drug-induced Liver Injury (DILI):	0.201
AMES Toxicity:	0.924	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	0.998
Carcinogencity:	0.043	Eye Corrosion:	0.0
Eye Irritation:	0.015	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.987
Hematotoxicity:	0.312	Drug-induced Nephrotoxicity:	0.654
Genotoxicity:	0.008	RPMI-8226 Immunitoxicity:	0.189
A549 Cytotoxicity:	0.623	Hek293 Cytotoxicity:	0.658
BCF:	0.581 ? 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:	3.135 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.809 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.903 ? 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
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10361686]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25900014]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	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 NPC262451 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	12355
0.1-0.2	31360
0.2-0.3	5223
0.3-0.4	762
0.4-0.5	100
0.5-0.6	26
0.6-0.7	13
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34587
0.9146	High Similarity	NPC100998
0.8916	High Similarity	NPC34927
0.7826	Intermediate Similarity	NPC471062
0.7816	Intermediate Similarity	NPC252292
0.7805	Intermediate Similarity	NPC46137
0.7742	Intermediate Similarity	NPC470934
0.7619	Intermediate Similarity	NPC472350
0.7619	Intermediate Similarity	NPC197316
0.7619	Intermediate Similarity	NPC89105
0.7474	Intermediate Similarity	NPC306890
0.7473	Intermediate Similarity	NPC259347
0.7447	Intermediate Similarity	NPC470933
0.7273	Intermediate Similarity	NPC263829
0.7216	Intermediate Similarity	NPC94871
0.7204	Intermediate Similarity	NPC476382
0.7111	Intermediate Similarity	NPC269141
0.7041	Intermediate Similarity	NPC473427
0.6957	Remote Similarity	NPC112
0.6346	Remote Similarity	NPC476386
0.6316	Remote Similarity	NPC298257
0.6316	Remote Similarity	NPC175214
0.6304	Remote Similarity	NPC76406
0.6264	Remote Similarity	NPC483705
0.6262	Remote Similarity	NPC257970
0.625	Remote Similarity	NPC600370
0.6237	Remote Similarity	NPC611289
0.6196	Remote Similarity	NPC134405
0.617	Remote Similarity	NPC106677
0.6154	Remote Similarity	NPC483706
0.6111	Remote Similarity	NPC470927
0.5979	Remote Similarity	NPC205864
0.5979	Remote Similarity	NPC247032
0.596	Remote Similarity	NPC96795
0.596	Remote Similarity	NPC264632
0.596	Remote Similarity	NPC232992
0.5941	Remote Similarity	NPC106818
0.59	Remote Similarity	NPC300894
0.59	Remote Similarity	NPC23845
0.5865	Remote Similarity	NPC87403
0.5758	Remote Similarity	NPC296954
0.5648	Remote Similarity	NPC188393
0.5542	Remote Similarity	NPC157554
0.5521	Remote Similarity	NPC68092
0.5444	Remote Similarity	NPC473285
0.534	Remote Similarity	NPC610636
0.5294	Remote Similarity	NPC119537
0.5278	Remote Similarity	NPC476398
0.5263	Remote Similarity	NPC81515
0.5263	Remote Similarity	NPC235294
0.5189	Remote Similarity	NPC476384
0.5165	Remote Similarity	NPC35731
0.5155	Remote Similarity	NPC64141
0.5138	Remote Similarity	NPC64195
0.5111	Remote Similarity	NPC886
0.5093	Remote Similarity	NPC476380
0.5093	Remote Similarity	NPC476381

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC262451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4092
0.1-0.2	4874
0.2-0.3	179
0.3-0.4	4
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
0.7619	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