NPASS Compound

Natural Product: NPC308621

Natural Product ID	NPC308621
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KGOGPLIYSKLAJZ-GVSGZQIYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11968407
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid 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 78 82 0 0 0 0 0 0 0 0999 V2000 -7.6147 -1.1316 -0.8980 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8366 0.3444 -1.1518 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3988 0.9450 0.1079 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1841 2.4408 0.1391 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7550 2.8101 -0.0152 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9740 1.5666 -0.5160 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7515 1.9632 -0.9312 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5772 1.6384 -0.4494 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0145 0.2519 -0.5294 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8013 -0.8284 0.1344 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7503 -1.8365 0.6807 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7297 -1.9829 -0.4228 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8923 -0.7139 -0.3874 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0730 -0.9066 0.6034 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4229 -0.7629 0.5206 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0570 -0.3803 -0.6393 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4307 -0.2262 -0.7465 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1843 -0.4780 0.3927 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5565 -0.3419 0.3556 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2436 -0.5676 1.3841 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1515 0.0482 -0.8394 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3463 0.2810 -1.9327 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0306 0.1381 -1.8497 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6076 0.1897 -0.8604 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4000 -0.7873 -0.2957 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7903 -0.6702 -0.2988 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4122 0.4182 -0.8625 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6255 1.3949 -1.4271 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2470 1.2753 -1.4225 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7908 0.5184 -0.8557 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3951 1.6608 -1.4460 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5368 -0.8643 1.5602 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1767 -1.0172 1.6676 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6057 -1.4070 2.8714 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4017 -2.7641 3.2009 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2986 -1.1184 2.7069 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7133 0.3307 0.0618 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3048 -2.2311 -1.6399 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1957 -1.2962 1.8195 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4960 -1.6131 -0.8194 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7241 1.0342 -1.5527 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2317 3.0502 1.2769 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7552 2.9277 1.3148 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0267 0.2993 1.2669 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1244 -1.6386 -1.7517 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6259 -1.5954 -0.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0822 -1.3065 0.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5983 0.4237 -1.9910 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5242 0.8285 0.0134 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8212 2.8359 -0.7112 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5626 3.6764 -0.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0162 0.8780 0.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8029 2.2975 -1.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3972 2.0227 0.6185 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8931 -0.0131 -1.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3968 -0.5505 0.9962 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2781 -2.8045 0.8665 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1205 -2.8730 -0.1568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5228 -0.4191 -1.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4913 -0.1743 -1.5481 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8396 0.5838 -2.8556 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9310 -1.6577 0.1579 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3865 -1.4507 0.1521 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1137 2.2481 -1.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6642 2.0569 -1.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9228 2.5594 -0.9891 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4707 1.7036 -1.1693 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2423 1.6132 -2.5317 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3929 -2.8545 3.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3893 -3.3331 2.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1948 -3.1434 3.8519 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7883 -2.0002 2.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7067 -2.7996 -2.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6527 -0.4665 2.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7403 -2.4864 -0.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2070 2.1926 1.7864 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0272 3.8740 1.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7839 0.1718 1.8645 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 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 2 0 22 23 1 0 21 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 27 30 1 0 30 31 1 0 18 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 32 36 1 0 13 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 37 9 1 0 33 15 1 0 23 17 1 0 29 24 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 6 3 49 1 6 4 50 1 6 5 51 1 6 6 52 1 1 8 53 1 0 8 54 1 0 9 55 1 6 10 56 1 1 11 57 1 1 12 58 1 1 13 59 1 6 16 60 1 0 22 61 1 0 25 62 1 0 26 63 1 0 28 64 1 0 29 65 1 0 31 66 1 0 31 67 1 0 31 68 1 0 35 69 1 0 35 70 1 0 35 71 1 0 36 72 1 0 38 73 1 0 39 74 1 0 40 75 1 0 42 76 1 0 43 77 1 0 44 78 1 0 M END

Standard InCHIKey	KGOGPLIYSKLAJZ-GVSGZQIYSA-N
Standard InCHI	InChI=1S/C29H34O15/c1-11-19(30)23(34)25(36)28(42-11)41-10-17-21(32)24(35)26(37)29(44-17)43-16-8-15-18(22(33)27(16)39-3)20(31)14(9-40-15)12-4-6-13(38-2)7-5-12/h4-9,11,17,19,21,23-26,28-30,32-37H,10H2,1-3H3/t11-,17+,19+,21+,23+,24-,25+,26+,28+,29+/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](Oc3cc4c(c(=O)c(co4)c4ccc(cc4)OC)c(c3OC)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.19	Volume:	578.119 ? Van der Waals volume.
Dense:	1.076	LogP:	0.694 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.358 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.395 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	227.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.163	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.687	Fsp³:	0.483
MCE-18:	117.814 ? 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:	0.555	Fluc inhibitor:	0.277 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.722 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.531 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.041	Promiscuous compounds:	0.201

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.218	MDCK Permeability:	-5.389
Pgp-inhibitor:	0.0	Pgp-substrate:	0.88
PAMPA:	0.999 ? 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):	0.879
20% Bioavailability (F20%):	0.071	30% Bioavailability (F30%):	0.817
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.119
Plasma Protein Binding (PPB):	81.76%	Volume Distribution (VD):	-0.321
Fu:	16.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.047
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.061	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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.988
HLM stability:	0.001 ? 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):

1.756

Half-life (T1/2):

4.667

ADMET: Toxicity

hERG Blockers:	0.064	hERG Blockers (10um):	0.265
Human Hepatotoxicity (H-HT):	0.288	Drug-induced Liver Injury (DILI):	0.716
AMES Toxicity:	0.786	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.018	Skin Sensitization:	0.56
Carcinogencity:	0.036	Eye Corrosion:	0.0
Eye Irritation:	0.016	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.987
Hematotoxicity:	0.194	Drug-induced Nephrotoxicity:	0.578
Genotoxicity:	0.037	RPMI-8226 Immunitoxicity:	0.172
A549 Cytotoxicity:	0.117	Hek293 Cytotoxicity:	0.215
BCF:	0.319 ? 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:	3.133 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.63 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.803 ? 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
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(99)00103-X]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19969457]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21314138]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27553	Derris scandens	Species	Fabaceae	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 NPC308621 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	14350
0.1-0.2	31019
0.2-0.3	3639
0.3-0.4	618
0.4-0.5	176
0.5-0.6	37
0.6-0.7	13
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
0.7701	Intermediate Similarity	NPC475155
0.7222	Intermediate Similarity	NPC204693
0.7111	Intermediate Similarity	NPC303913
0.6633	Remote Similarity	NPC475261
0.6632	Remote Similarity	NPC257714
0.6444	Remote Similarity	NPC99957
0.6395	Remote Similarity	NPC160515
0.6292	Remote Similarity	NPC205076
0.6264	Remote Similarity	NPC307518
0.6211	Remote Similarity	NPC479405
0.6146	Remote Similarity	NPC479404
0.6132	Remote Similarity	NPC473895
0.6042	Remote Similarity	NPC22062
0.6042	Remote Similarity	NPC473634
0.6042	Remote Similarity	NPC138811
0.6	Remote Similarity	NPC73511
0.596	Remote Similarity	NPC483707
0.596	Remote Similarity	NPC51326
0.5957	Remote Similarity	NPC211594
0.5895	Remote Similarity	NPC487212
0.587	Remote Similarity	NPC224462
0.5862	Remote Similarity	NPC25547
0.5851	Remote Similarity	NPC48773
0.5686	Remote Similarity	NPC231194
0.567	Remote Similarity	NPC187379
0.5631	Remote Similarity	NPC235575
0.5604	Remote Similarity	NPC259070
0.5604	Remote Similarity	NPC348541
0.5545	Remote Similarity	NPC479403
0.5495	Remote Similarity	NPC135345
0.549	Remote Similarity	NPC209296
0.5435	Remote Similarity	NPC211014
0.5326	Remote Similarity	NPC45165
0.5326	Remote Similarity	NPC114740
0.5294	Remote Similarity	NPC475366
0.5243	Remote Similarity	NPC470443
0.5238	Remote Similarity	NPC473073
0.5233	Remote Similarity	NPC469622
0.5213	Remote Similarity	NPC156457
0.5196	Remote Similarity	NPC473571
0.5196	Remote Similarity	NPC110941
0.5192	Remote Similarity	NPC473327
0.5155	Remote Similarity	NPC181616
0.5149	Remote Similarity	NPC44931
0.5149	Remote Similarity	NPC67105
0.5146	Remote Similarity	NPC126784
0.5146	Remote Similarity	NPC241423
0.5143	Remote Similarity	NPC488089
0.5098	Remote Similarity	NPC233994
0.5098	Remote Similarity	NPC210073
0.5053	Remote Similarity	NPC487213
0.5049	Remote Similarity	NPC186816
0.5048	Remote Similarity	NPC473623

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC308621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4223
0.1-0.2	4834
0.2-0.3	82
0.3-0.4	4
0.4-0.5	4
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
0.549	Remote Similarity	NPD7054	Phase 4
0.5046	Remote Similarity	NPD7472	Pre-clinical
0.5046	Remote Similarity	NPD7808	Phase 3

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