NPASS Compound

Natural Product: NPC29551

Natural Product ID	NPC29551
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VZYBBNWLNANBBV-NSCADYBNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101995289
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 69 74 0 0 0 0 0 0 0 0999 V2000 -1.8388 3.1253 0.5795 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 1.7697 0.8611 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0854 0.7843 -0.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7043 1.1484 -1.1697 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8817 2.4946 -1.4459 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4602 3.4865 -0.5928 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6299 4.8345 -0.8540 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1317 0.1334 -2.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5612 -1.0823 -1.4005 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8331 -0.8082 -0.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1169 -1.2474 0.5363 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3333 -0.9760 1.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2909 -0.2478 0.5336 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0255 0.2095 -0.7456 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8197 -0.0631 -1.3664 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0235 0.9516 -1.3724 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5097 0.0265 1.1640 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5636 -1.4550 2.4620 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4685 -1.6202 -0.5462 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8439 -0.6242 0.3903 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3913 -0.8676 0.5828 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1319 -1.3911 1.7559 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4834 -1.6106 1.9141 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3748 -1.3183 0.9101 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8317 -0.7906 -0.2674 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7491 -0.4462 -1.4133 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8176 -1.5346 -1.3835 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6057 -1.5187 -0.1226 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6385 -0.4907 -0.0235 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9448 0.3258 -1.0735 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9297 1.2858 -0.9419 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6008 1.4061 0.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2876 0.5796 1.3291 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3035 -0.3772 1.1919 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9894 0.7469 2.5123 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5916 2.3583 0.4349 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2396 2.1144 -2.0093 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7378 -1.5205 1.0203 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1003 -2.7544 -1.4248 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4868 -0.5689 -0.4328 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0378 -0.0342 -1.6560 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7284 -1.7039 2.8026 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5208 -2.1889 -1.4083 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4836 3.8694 1.2949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1628 1.5434 1.7981 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3658 2.7623 -2.3601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1910 5.3745 -0.2051 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7009 -1.7975 -2.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4286 -1.8247 1.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6440 0.3086 -2.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9684 1.9575 -1.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3322 -0.3556 0.6792 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4502 -1.8419 2.7089 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8578 -2.4930 0.0371 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3098 -0.7648 1.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8626 -2.0184 2.8359 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1510 0.5515 -1.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2470 -0.5252 -2.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4666 -1.5484 -2.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1339 -2.5160 -0.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4222 0.2208 -1.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0694 -1.0185 2.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9420 1.0565 2.5599 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7680 3.0302 -0.2872 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2272 1.7820 -2.9511 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2239 -3.2730 -0.6125 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5788 0.7498 -2.0428 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6800 -1.2427 3.7079 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9789 -2.5274 -2.2246 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 4 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 13 17 1 0 12 18 1 0 9 19 1 0 19 20 1 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 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 32 36 1 0 31 37 1 0 28 38 1 0 27 39 1 0 25 40 2 0 40 41 1 0 22 42 1 0 19 43 1 0 6 1 1 0 15 10 1 0 40 21 1 0 20 3 1 0 38 24 1 0 34 29 1 0 1 44 1 0 2 45 1 0 5 46 1 0 7 47 1 0 9 48 1 6 11 49 1 0 15 50 1 0 16 51 1 0 17 52 1 0 18 53 1 0 19 54 1 1 20 55 1 1 23 56 1 0 26 57 1 0 26 58 1 0 27 59 1 6 28 60 1 1 30 61 1 0 34 62 1 0 35 63 1 0 36 64 1 0 37 65 1 0 39 66 1 0 41 67 1 0 42 68 1 0 43 69 1 0 M END

Standard InCHIKey	VZYBBNWLNANBBV-NSCADYBNSA-N
Standard InCHI	InChI=1S/C30H26O13/c31-12-1-2-13-21(7-12)43-30(11-5-18(35)27(40)19(36)6-11)28(41)23(13)24-15(32)9-22-14(25(24)38)8-20(37)29(42-22)10-3-16(33)26(39)17(34)4-10/h1-7,9,20,23,28-41H,8H2/t20-,23+,28-,29+,30+/m0/s1
SMILES	c1cc2c(cc1O)O[C@H](c1cc(c(c(c1)O)O)O)[C@H]([C@H]2c1c(cc2c(C[C@@H]([C@@H](c3cc(c(c(c3)O)O)O)O2)O)c1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.14	Volume:	558.733 ? Van der Waals volume.
Dense:	1.063	LogP:	0.73 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.129 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.158 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	34.0
TPSA:	240.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.153	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.67	Fsp³:	0.2
MCE-18:	130.0 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.884	Fluc inhibitor:	0.177 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.124 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.373 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.595	Promiscuous compounds:	0.283

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.318	MDCK Permeability:	-4.846
Pgp-inhibitor:	0.0	Pgp-substrate:	0.004
PAMPA:	0.983 ? 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):	0.013
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:	0.937
Plasma Protein Binding (PPB):	91.307%	Volume Distribution (VD):	0.075
Fu:	12.115% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.009
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.197	CYP2C19-substrate:	0.702
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

7.289

Half-life (T1/2):

4.161

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.961
Human Hepatotoxicity (H-HT):	0.91	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.653	Rat Oral Acute Toxicity:	0.533
Maximum Recommended Daily Dose:	0.996	Skin Sensitization:	1.0
Carcinogencity:	0.008	Eye Corrosion:	0.0
Eye Irritation:	0.789	Respiratory Toxicity:	0.765
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.008	Drug-induced Nephrotoxicity:	0.041
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.004
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.945
BCF:	0.891 ? 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:	3.463 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.544 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.992 ? 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
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29975532]
NPO28288	Calopogonium mucunoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28091	Cantharellus cinnabarinus	Species	Cantharellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28222	Psorospermum glaberrimum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20176	Calia arizonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27871	Erigeron philadelphicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28600	Stryphnodendron adstringens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28338	Balduina uniflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27963	Espeletiopsis guacharaca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28379	Dilophus marginatus	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28203	Beyeria leschenaultii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27871	Erigeron philadelphicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8149	Aspergillus aurantiobrunneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28600	Stryphnodendron adstringens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20176	Calia arizonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28222	Psorospermum glaberrimum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4139	Vellozia plicata	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28203	Beyeria leschenaultii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17184	Akashiwo sanguinea	Species	Gymnodiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27963	Espeletiopsis guacharaca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28379	Dilophus marginatus	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28513	Pluchea rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29404	Xanthorrhoea media	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28091	Cantharellus cinnabarinus	Species	Cantharellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28288	Calopogonium mucunoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28338	Balduina uniflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28676	Chrysanthemum ferulaceum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27871	Erigeron philadelphicus	Species	Asteraceae	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 NPC29551 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	27456
0.1-0.2	20219
0.2-0.3	1913
0.3-0.4	171
0.4-0.5	54
0.5-0.6	28
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8644	High Similarity	NPC82917
0.6812	Remote Similarity	NPC601997
0.6812	Remote Similarity	NPC609211
0.6812	Remote Similarity	NPC610665
0.6714	Remote Similarity	NPC600630
0.6714	Remote Similarity	NPC607896
0.6714	Remote Similarity	NPC611369
0.6567	Remote Similarity	NPC294558
0.6567	Remote Similarity	NPC18185
0.6567	Remote Similarity	NPC263940
0.6143	Remote Similarity	NPC313116
0.6143	Remote Similarity	NPC603340
0.6111	Remote Similarity	NPC226809
0.5972	Remote Similarity	NPC70409
0.5972	Remote Similarity	NPC204770
0.5972	Remote Similarity	NPC600551
0.5972	Remote Similarity	NPC601980
0.5972	Remote Similarity	NPC602065
0.5972	Remote Similarity	NPC611024
0.5942	Remote Similarity	NPC601999
0.5833	Remote Similarity	NPC268266
0.5833	Remote Similarity	NPC42760
0.5833	Remote Similarity	NPC220825
0.5833	Remote Similarity	NPC268342
0.5652	Remote Similarity	NPC96576
0.5238	Remote Similarity	NPC478340
0.5156	Remote Similarity	NPC261619
0.5156	Remote Similarity	NPC61477
0.5156	Remote Similarity	NPC78770
0.5156	Remote Similarity	NPC219876
0.5156	Remote Similarity	NPC126029
0.5156	Remote Similarity	NPC15658
0.5079	Remote Similarity	NPC207179
0.5079	Remote Similarity	NPC167571
0.5079	Remote Similarity	NPC278552
0.5068	Remote Similarity	NPC58190
0.5068	Remote Similarity	NPC108811
0.5068	Remote Similarity	NPC170103
0.5068	Remote Similarity	NPC236202
0.5068	Remote Similarity	NPC262911
0.5068	Remote Similarity	NPC202742

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC29551 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5464
0.1-0.2	3637
0.2-0.3	39
0.3-0.4	8
0.4-0.5	0
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
0.5156	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5156	Remote Similarity	NPD1613	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