NPASS Compound

Natural Product: NPC110823

Natural Product ID	NPC110823
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CHOMRSQGIORTSD-CMWHQFSMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5318789
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 76 80 0 0 0 0 0 0 0 0999 V2000 7.3914 -1.3579 1.7278 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3510 -0.7324 0.8308 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9900 0.2275 -0.1211 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9653 0.7774 -1.0891 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9895 -0.2831 -1.5375 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4103 -0.9152 -0.2809 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3362 -1.6871 -0.4991 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1721 -1.4333 0.1016 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.2333 -0.2190 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9395 1.1030 0.0930 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9500 2.1751 -0.3010 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4842 1.8621 -0.0910 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8410 0.4562 0.0772 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2092 -0.3229 0.6086 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8948 0.2723 1.0487 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8336 -0.7399 0.8405 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4324 -2.0091 1.3127 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3323 -2.1850 1.8720 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2684 -3.0828 1.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9218 -4.3599 1.6030 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7758 -5.4249 1.4347 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9821 -5.1970 0.8135 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3209 -3.9376 0.3747 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4724 -2.8397 0.5332 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8025 -1.6521 0.1147 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0323 -0.5676 0.2394 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5139 0.7109 -0.2671 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6231 0.6967 -1.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2121 1.8049 -1.6352 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6903 3.0469 -1.2904 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6035 3.1228 -0.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0321 1.9423 0.0487 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0385 4.3499 -0.0721 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5429 5.5761 -0.5218 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3191 1.7370 -2.4901 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8373 -6.2935 0.6516 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6759 -4.4979 2.2230 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1495 2.3446 -1.2498 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2812 3.3119 0.4496 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1343 1.2401 1.4697 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5087 -1.6574 0.2488 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6127 -1.2369 -2.3397 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6007 1.3896 -2.1656 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4641 1.3166 0.6192 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0835 -0.5322 2.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8851 -1.6822 2.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9796 -2.1443 1.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6991 -0.1112 1.5141 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8794 -0.2010 -0.6439 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3932 1.5601 -0.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 0.2004 -2.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2512 -0.1191 0.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2919 -1.4371 1.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4866 -2.3215 -0.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9332 -0.2788 -1.2522 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8582 1.3369 -0.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1808 2.4722 -1.3661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8990 2.4983 0.7475 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1190 -0.0694 -0.8519 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4990 -6.4077 1.7829 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2640 -3.7711 -0.1084 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0136 -0.2852 -1.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1284 3.9628 -1.6744 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1977 2.0115 0.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6562 5.6182 -0.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0530 6.3858 0.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3082 5.7373 -1.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1987 1.9426 -3.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7883 -6.1597 0.9792 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0631 -5.2444 1.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5673 1.6095 -1.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0328 4.1181 -0.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3594 2.1977 1.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5695 -1.3329 -2.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9172 1.6399 -2.8380 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7239 1.9891 0.7142 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 7 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 29 35 1 0 22 36 1 0 20 37 1 0 12 38 1 0 11 39 1 0 10 40 1 0 6 41 1 0 5 42 1 0 4 43 1 0 3 44 1 0 41 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 24 19 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 1 3 49 1 6 4 50 1 1 5 51 1 6 6 52 1 1 8 53 1 0 8 54 1 0 9 55 1 6 10 56 1 6 11 57 1 6 12 58 1 1 13 59 1 6 21 60 1 0 23 61 1 0 28 62 1 0 30 63 1 0 32 64 1 0 34 65 1 0 34 66 1 0 34 67 1 0 35 68 1 0 36 69 1 0 37 70 1 0 38 71 1 0 39 72 1 0 40 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 M END

Standard InCHIKey	CHOMRSQGIORTSD-CMWHQFSMSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-14(31)6-12(30)7-15(17)42-25(26)10-3-11(29)5-13(4-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19-,21+,22-,23+,24+,27-,28-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2cc(cc(c2)OC)O)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	1.131 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.597 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.288 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.811	Fsp³:	0.464
MCE-18:	122.073 ? 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:	0.63	Fluc inhibitor:	0.127 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.721 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.659 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.07	Promiscuous compounds:	0.519

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.432	MDCK Permeability:	-5.21
Pgp-inhibitor:	0.0	Pgp-substrate:	0.899
PAMPA:	0.991 ? 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):	0.016
20% Bioavailability (F20%):	0.167	30% Bioavailability (F30%):	0.866
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.075
Plasma Protein Binding (PPB):	84.691%	Volume Distribution (VD):	-0.061
Fu:	13.934% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.968
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.393
BSEP inhibitor:	0.258

ADMET: Metabolism

CYP1A2-inhibitor:	0.077	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.822
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.992 ? 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):

0.98

Half-life (T1/2):

3.936

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.31
Human Hepatotoxicity (H-HT):	0.456	Drug-induced Liver Injury (DILI):	0.785
AMES Toxicity:	0.868	Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.26	Skin Sensitization:	0.989
Carcinogencity:	0.073	Eye Corrosion:	0.0
Eye Irritation:	0.705	Respiratory Toxicity:	0.08
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.843
Hematotoxicity:	0.127	Drug-induced Nephrotoxicity:	0.493
Genotoxicity:	0.94	RPMI-8226 Immunitoxicity:	0.226
A549 Cytotoxicity:	0.436	Hek293 Cytotoxicity:	0.688
BCF:	0.468 ? 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:	3.194 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.748 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.856 ? 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
NPO13468.1	Cryptomeria japonica var. sinensis	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30485090]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13468.1	Cryptomeria japonica var. sinensis	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13468.1	Cryptomeria japonica var. sinensis	Varieties	Cupressaceae	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 NPC110823 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	18899
0.1-0.2	27188
0.2-0.3	2860
0.3-0.4	454
0.4-0.5	246
0.5-0.6	134
0.6-0.7	49
0.7-0.8	1
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8023	Intermediate Similarity	NPC173582
0.8023	Intermediate Similarity	NPC265885
0.8023	Intermediate Similarity	NPC181465
0.8023	Intermediate Similarity	NPC215710
0.8023	Intermediate Similarity	NPC39834
0.8023	Intermediate Similarity	NPC473438
0.8023	Intermediate Similarity	NPC253788
0.8	Intermediate Similarity	NPC476472
0.8	Intermediate Similarity	NPC294815
0.8	Intermediate Similarity	NPC16194
0.7978	Intermediate Similarity	NPC473327
0.7931	Intermediate Similarity	NPC203259
0.7931	Intermediate Similarity	NPC33054
0.7931	Intermediate Similarity	NPC176740
0.7931	Intermediate Similarity	NPC471725
0.7931	Intermediate Similarity	NPC134532
0.7931	Intermediate Similarity	NPC602582
0.6957	Remote Similarity	NPC156869
0.6923	Remote Similarity	NPC471079
0.6923	Remote Similarity	NPC609888
0.6882	Remote Similarity	NPC473571
0.6882	Remote Similarity	NPC110941
0.6882	Remote Similarity	NPC186816
0.6848	Remote Similarity	NPC67326
0.6809	Remote Similarity	NPC126784
0.6809	Remote Similarity	NPC241423
0.6739	Remote Similarity	NPC187379
0.6667	Remote Similarity	NPC265530
0.6632	Remote Similarity	NPC153755
0.66	Remote Similarity	NPC89052
0.6596	Remote Similarity	NPC65563
0.6596	Remote Similarity	NPC470949
0.6562	Remote Similarity	NPC12013
0.6562	Remote Similarity	NPC11432
0.6562	Remote Similarity	NPC477613
0.6535	Remote Similarity	NPC189564
0.6522	Remote Similarity	NPC116864
0.6522	Remote Similarity	NPC244776
0.6495	Remote Similarity	NPC122467
0.6484	Remote Similarity	NPC223747
0.6471	Remote Similarity	NPC292019
0.6471	Remote Similarity	NPC202908
0.6471	Remote Similarity	NPC173837
0.6444	Remote Similarity	NPC219904
0.6437	Remote Similarity	NPC111929
0.6437	Remote Similarity	NPC320283
0.6437	Remote Similarity	NPC135599
0.6437	Remote Similarity	NPC73855
0.6437	Remote Similarity	NPC41121
0.6437	Remote Similarity	NPC113968
0.6437	Remote Similarity	NPC328940
0.6437	Remote Similarity	NPC277174
0.6437	Remote Similarity	NPC606877
0.6436	Remote Similarity	NPC203145
0.6392	Remote Similarity	NPC470443
0.6364	Remote Similarity	NPC127546
0.6364	Remote Similarity	NPC57625
0.6364	Remote Similarity	NPC173637
0.6364	Remote Similarity	NPC317489
0.6364	Remote Similarity	NPC223424
0.6364	Remote Similarity	NPC89127
0.6364	Remote Similarity	NPC600591
0.63	Remote Similarity	NPC221342
0.63	Remote Similarity	NPC476470
0.6238	Remote Similarity	NPC602448
0.6036	Remote Similarity	NPC192539
0.5978	Remote Similarity	NPC472459
0.5978	Remote Similarity	NPC325555
0.5978	Remote Similarity	NPC226304
0.596	Remote Similarity	NPC488073
0.596	Remote Similarity	NPC488074
0.5943	Remote Similarity	NPC303694
0.5941	Remote Similarity	NPC142142
0.5918	Remote Similarity	NPC605592
0.5882	Remote Similarity	NPC473073
0.5882	Remote Similarity	NPC471669
0.587	Remote Similarity	NPC46420
0.5859	Remote Similarity	NPC129264
0.5849	Remote Similarity	NPC477895
0.5816	Remote Similarity	NPC67105
0.5816	Remote Similarity	NPC227508
0.5804	Remote Similarity	NPC241781
0.58	Remote Similarity	NPC470125
0.5794	Remote Similarity	NPC217520
0.5761	Remote Similarity	NPC64305
0.5761	Remote Similarity	NPC158674
0.5758	Remote Similarity	NPC22062
0.5758	Remote Similarity	NPC473634
0.5758	Remote Similarity	NPC138811
0.5745	Remote Similarity	NPC175107
0.5729	Remote Similarity	NPC203050
0.5729	Remote Similarity	NPC225434
0.5729	Remote Similarity	NPC476215
0.5728	Remote Similarity	NPC85751
0.5728	Remote Similarity	NPC19240
0.5699	Remote Similarity	NPC271692
0.5688	Remote Similarity	NPC139571
0.5686	Remote Similarity	NPC37668
0.5686	Remote Similarity	NPC270448
0.5686	Remote Similarity	NPC209296
0.5684	Remote Similarity	NPC120099
0.5673	Remote Similarity	NPC470449
0.567	Remote Similarity	NPC95866
0.5657	Remote Similarity	NPC44931
0.5652	Remote Similarity	NPC19388
0.5652	Remote Similarity	NPC240431
0.5652	Remote Similarity	NPC77672
0.5652	Remote Similarity	NPC55786
0.5652	Remote Similarity	NPC133671
0.5652	Remote Similarity	NPC135391
0.5652	Remote Similarity	NPC78263
0.5652	Remote Similarity	NPC250069
0.5648	Remote Similarity	NPC25523
0.5641	Remote Similarity	NPC473554
0.5625	Remote Similarity	NPC156785
0.5625	Remote Similarity	NPC162394
0.5625	Remote Similarity	NPC474522
0.5619	Remote Similarity	NPC470446
0.5619	Remote Similarity	NPC223426
0.56	Remote Similarity	NPC210073
0.5591	Remote Similarity	NPC145038
0.5591	Remote Similarity	NPC56077
0.5591	Remote Similarity	NPC281131
0.5591	Remote Similarity	NPC253662
0.5591	Remote Similarity	NPC179950
0.5591	Remote Similarity	NPC88789
0.5591	Remote Similarity	NPC491374
0.5577	Remote Similarity	NPC470447
0.5577	Remote Similarity	NPC220173
0.5566	Remote Similarity	NPC214621
0.5566	Remote Similarity	NPC34267
0.5566	Remote Similarity	NPC81042
0.5524	Remote Similarity	NPC292929
0.5524	Remote Similarity	NPC287889
0.5524	Remote Similarity	NPC470445
0.5505	Remote Similarity	NPC480441
0.55	Remote Similarity	NPC163242
0.55	Remote Similarity	NPC272068
0.5484	Remote Similarity	NPC249281
0.5464	Remote Similarity	NPC209023
0.5446	Remote Similarity	NPC155877
0.5429	Remote Similarity	NPC76831
0.5417	Remote Similarity	NPC60735
0.5417	Remote Similarity	NPC26230
0.5417	Remote Similarity	NPC611303
0.5413	Remote Similarity	NPC48984
0.5408	Remote Similarity	NPC276377
0.54	Remote Similarity	NPC139320
0.5398	Remote Similarity	NPC480445
0.5392	Remote Similarity	NPC204693
0.5385	Remote Similarity	NPC54802
0.5385	Remote Similarity	NPC197304
0.537	Remote Similarity	NPC121703
0.5368	Remote Similarity	NPC305811
0.5361	Remote Similarity	NPC609478
0.5347	Remote Similarity	NPC471748
0.5326	Remote Similarity	NPC288084
0.5326	Remote Similarity	NPC276222
0.5326	Remote Similarity	NPC274618
0.5326	Remote Similarity	NPC34531
0.5326	Remote Similarity	NPC118284
0.5326	Remote Similarity	NPC608147
0.5304	Remote Similarity	NPC480444
0.5294	Remote Similarity	NPC487499
0.5278	Remote Similarity	NPC470455
0.5269	Remote Similarity	NPC67037
0.5269	Remote Similarity	NPC255615
0.5258	Remote Similarity	NPC159579
0.5258	Remote Similarity	NPC182121
0.5248	Remote Similarity	NPC29958
0.52	Remote Similarity	NPC487500
0.5192	Remote Similarity	NPC296018
0.5192	Remote Similarity	NPC154741
0.5175	Remote Similarity	NPC488734
0.5175	Remote Similarity	NPC488735
0.5175	Remote Similarity	NPC488739
0.5175	Remote Similarity	NPC488732
0.5175	Remote Similarity	NPC488738
0.5159	Remote Similarity	NPC487501
0.5152	Remote Similarity	NPC116458
0.5152	Remote Similarity	NPC246943
0.5146	Remote Similarity	NPC303913
0.5146	Remote Similarity	NPC150164
0.5135	Remote Similarity	NPC219043
0.5124	Remote Similarity	NPC275977
0.5124	Remote Similarity	NPC483159
0.5124	Remote Similarity	NPC483160
0.5122	Remote Similarity	NPC487502
0.5086	Remote Similarity	NPC488740
0.5086	Remote Similarity	NPC488736
0.5086	Remote Similarity	NPC488733
0.5052	Remote Similarity	NPC52550
0.5052	Remote Similarity	NPC27640
0.5052	Remote Similarity	NPC349108
0.5049	Remote Similarity	NPC470405
0.5049	Remote Similarity	NPC275454
0.5048	Remote Similarity	NPC240306
0.5048	Remote Similarity	NPC475366
0.5047	Remote Similarity	NPC486577
0.5045	Remote Similarity	NPC470451

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC110823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5360
0.1-0.2	3743
0.2-0.3	38
0.3-0.4	2
0.4-0.5	3
0.5-0.6	1
0.6-0.7	2
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
0.7931	Intermediate Similarity	NPD6797	Phase 2
0.6364	Remote Similarity	NPD7251	Phase 2
0.6275	Remote Similarity	NPD7808	Phase 3
0.5686	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