NPASS Compound

Natural Product: NPC230200

Natural Product ID	NPC230200
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UOMGQSMGUAHMST-LSVBLFBYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5316287
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 62 65 0 0 0 0 0 0 0 0999 V2000 9.3712 -1.2030 -1.8186 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7108 -0.5939 -0.7314 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3146 -0.5324 -0.6958 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5788 -1.0613 -1.7129 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2043 -1.0046 -1.6850 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5093 -0.4168 -0.6388 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2810 0.1134 0.3826 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6515 0.0550 0.3512 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3844 0.5996 1.3972 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5751 0.6950 1.4123 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2274 1.1879 2.3568 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1748 0.7355 1.4065 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5008 0.1896 0.3682 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0528 0.1621 0.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4937 -0.2180 -0.9961 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8678 -0.3046 -1.1927 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7567 -0.0234 -0.1885 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2233 0.3546 1.0447 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1395 0.4329 1.2152 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0540 0.6572 2.1170 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4976 1.0369 3.3541 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1264 -0.0766 -0.2746 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8283 -0.4287 -1.4092 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6649 -1.6646 -1.2001 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0063 -1.6009 -1.8394 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7506 -0.3219 -1.5409 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8116 0.8284 -1.3513 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9052 1.3193 0.0713 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3281 0.5158 1.0117 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5531 0.6703 -1.8229 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5378 -0.4485 -0.3989 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8090 -2.6486 -1.3929 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9800 -2.7548 -1.7350 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2182 -0.3686 -0.6212 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5924 1.3425 2.4763 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3477 2.7529 2.5189 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4577 -1.0913 -1.7145 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1117 -2.2732 -1.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0460 -0.7072 -2.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0813 -1.5353 -2.5597 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6143 -1.4292 -2.5014 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5484 0.0383 2.2206 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1521 -0.4506 -1.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 -0.6086 -2.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5131 0.7070 2.2117 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 0.2867 3.7453 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2940 1.2476 4.0940 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9131 1.9954 3.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1282 -0.6610 -2.2337 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7656 -1.9171 -0.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9471 -1.7011 -2.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4805 -0.0826 -2.3689 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2494 1.6890 -1.9610 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9664 1.4798 0.3501 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4277 2.3385 0.1695 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1556 1.0562 1.8205 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3189 0.1809 -0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7394 -2.4326 -1.6600 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5677 -3.3441 -2.2703 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7411 3.0570 1.6456 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7287 2.9400 3.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3277 3.2395 2.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 7 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 17 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 24 33 1 0 13 34 1 0 12 35 1 0 35 36 1 0 8 3 1 0 19 14 1 0 30 23 1 0 34 6 1 0 1 37 1 0 1 38 1 0 1 39 1 0 4 40 1 0 5 41 1 0 9 42 1 0 15 43 1 0 16 44 1 0 19 45 1 0 21 46 1 0 21 47 1 0 21 48 1 0 23 49 1 6 24 50 1 1 25 51 1 6 26 52 1 6 27 53 1 6 28 54 1 0 28 55 1 0 29 56 1 0 31 57 1 0 32 58 1 0 33 59 1 0 36 60 1 0 36 61 1 0 36 62 1 0 M END

Standard InCHIKey	UOMGQSMGUAHMST-LSVBLFBYSA-N
Standard InCHI	InChI=1S/C24H26O12/c1-31-13-7-6-12-16(17(13)26)19(28)23(33-3)22(34-12)10-4-5-11(14(8-10)32-2)35-24-21(30)20(29)18(27)15(9-25)36-24/h4-8,15,18,20-21,24-27,29-30H,9H2,1-3H3/t15-,18+,20+,21-,24-/m1/s1
SMILES	COc1ccc2c(c1O)c(=O)c(c(c1ccc(c(c1)OC)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)o2)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	506.14	Volume:	473.825 ? Van der Waals volume.
Dense:	1.068	LogP:	1.257 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.658 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.138 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	24.0
TPSA:	177.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.298	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.903	Fsp³:	0.375
MCE-18:	89.182 ? 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:	0.485	Fluc inhibitor:	0.335 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.797 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.79 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.078	Promiscuous compounds:	0.433

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.991	MDCK Permeability:	-5.327
Pgp-inhibitor:	0.01	Pgp-substrate:	0.276
PAMPA:	0.898 ? 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):	0.972
20% Bioavailability (F20%):	0.214	30% Bioavailability (F30%):	0.963
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.648
Plasma Protein Binding (PPB):	93.472%	Volume Distribution (VD):	-0.18
Fu:	4.937% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.673
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.394
BSEP inhibitor:	0.223

ADMET: Metabolism

CYP1A2-inhibitor:	0.053	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.343	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.22
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.153
HLM stability:	0.409 ? 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):

2.323

Half-life (T1/2):

2.939

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.102
Human Hepatotoxicity (H-HT):	0.675	Drug-induced Liver Injury (DILI):	0.968
AMES Toxicity:	0.935	Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.047	Skin Sensitization:	0.997
Carcinogencity:	0.659	Eye Corrosion:	0.0
Eye Irritation:	0.442	Respiratory Toxicity:	0.138
Drug-induced Neurotoxicity:	0.03	Ototoxicity:	0.739
Hematotoxicity:	0.661	Drug-induced Nephrotoxicity:	0.595
Genotoxicity:	0.628	RPMI-8226 Immunitoxicity:	0.202
A549 Cytotoxicity:	0.713	Hek293 Cytotoxicity:	0.431
BCF:	0.446 ? 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:	3.262 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.616 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.877 ? 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
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32004936]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39053741]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28301	Clerodendron cyrtophyllum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28301	Clerodendron cyrtophyllum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28301	Clerodendron cyrtophyllum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4554	Isatis tinctoria	Species	Brassicaceae	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 NPC230200 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	19109
0.1-0.2	26801
0.2-0.3	2698
0.3-0.4	866
0.4-0.5	295
0.5-0.6	69
0.6-0.7	16
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
0.7037	Intermediate Similarity	NPC21666
0.6875	Remote Similarity	NPC603655
0.6667	Remote Similarity	NPC488072
0.6506	Remote Similarity	NPC609451
0.6429	Remote Similarity	NPC101026
0.6429	Remote Similarity	NPC488077
0.631	Remote Similarity	NPC488071
0.6265	Remote Similarity	NPC24043
0.6235	Remote Similarity	NPC609478
0.6163	Remote Similarity	NPC88023
0.6163	Remote Similarity	NPC607707
0.6071	Remote Similarity	NPC488080
0.6071	Remote Similarity	NPC169977
0.6047	Remote Similarity	NPC120099
0.6	Remote Similarity	NPC42773
0.6	Remote Similarity	NPC472459
0.6	Remote Similarity	NPC45522
0.5909	Remote Similarity	NPC203050
0.5909	Remote Similarity	NPC225434
0.5882	Remote Similarity	NPC84362
0.5862	Remote Similarity	NPC243930
0.5833	Remote Similarity	NPC289667
0.5814	Remote Similarity	NPC325555
0.5814	Remote Similarity	NPC226304
0.5795	Remote Similarity	NPC309025
0.5765	Remote Similarity	NPC64305
0.5747	Remote Similarity	NPC60735
0.5747	Remote Similarity	NPC26230
0.57	Remote Similarity	NPC48984
0.5698	Remote Similarity	NPC186807
0.5682	Remote Similarity	NPC148710
0.5647	Remote Similarity	NPC210042
0.5647	Remote Similarity	NPC58053
0.5618	Remote Similarity	NPC206123
0.5506	Remote Similarity	NPC605067
0.5465	Remote Similarity	NPC77672
0.5465	Remote Similarity	NPC133671
0.5465	Remote Similarity	NPC135391
0.5465	Remote Similarity	NPC78263
0.5465	Remote Similarity	NPC250069
0.5455	Remote Similarity	NPC182045
0.5455	Remote Similarity	NPC117260
0.5444	Remote Similarity	NPC602805
0.5435	Remote Similarity	NPC251417
0.5402	Remote Similarity	NPC145038
0.5402	Remote Similarity	NPC93337
0.5402	Remote Similarity	NPC56077
0.5402	Remote Similarity	NPC297987
0.5402	Remote Similarity	NPC281131
0.5402	Remote Similarity	NPC253662
0.5402	Remote Similarity	NPC179950
0.5402	Remote Similarity	NPC136042
0.5402	Remote Similarity	NPC88789
0.5402	Remote Similarity	NPC491374
0.5395	Remote Similarity	NPC176300
0.5393	Remote Similarity	NPC168584
0.5341	Remote Similarity	NPC105025
0.5341	Remote Similarity	NPC45638
0.5333	Remote Similarity	NPC486578
0.5287	Remote Similarity	NPC19388
0.5287	Remote Similarity	NPC240431
0.5287	Remote Similarity	NPC55786
0.5281	Remote Similarity	NPC201292
0.5281	Remote Similarity	NPC599850
0.5278	Remote Similarity	NPC488079
0.5269	Remote Similarity	NPC473682
0.5227	Remote Similarity	NPC95090
0.5227	Remote Similarity	NPC27408
0.5195	Remote Similarity	NPC115798
0.5169	Remote Similarity	NPC27640
0.5165	Remote Similarity	NPC22832
0.5155	Remote Similarity	NPC488073
0.5128	Remote Similarity	NPC605494
0.5111	Remote Similarity	NPC21100
0.5109	Remote Similarity	NPC307518
0.5109	Remote Similarity	NPC116458
0.5109	Remote Similarity	NPC246943
0.5109	Remote Similarity	NPC605784
0.5056	Remote Similarity	NPC8573
0.5055	Remote Similarity	NPC219904
0.5055	Remote Similarity	NPC285197
0.5055	Remote Similarity	NPC611303
0.5054	Remote Similarity	NPC469931
0.5054	Remote Similarity	NPC48773
0.5054	Remote Similarity	NPC601586
0.5053	Remote Similarity	NPC480466

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC230200 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5081
0.1-0.2	3972
0.2-0.3	81
0.3-0.4	12
0.4-0.5	3
0.5-0.6	0
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
		NPD

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