NPASS Compound

Natural Product: NPC475606

Natural Product ID	NPC475606
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TWWHDBCEIQHHFZ-ICEZPICISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509149
PubChem CID	44559851
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

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 77 82 0 0 0 0 0 0 0 0999 V2000 7.9394 -2.1945 -0.7239 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6860 -0.9821 -0.2548 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3275 -0.6823 1.1662 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9237 -0.3347 1.3572 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0442 -0.2351 0.3817 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6478 0.1193 0.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7883 0.2132 -0.3006 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3891 0.5590 -0.0912 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5416 0.6481 -1.0878 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0984 1.0040 -0.8806 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4184 1.4139 -2.1165 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 1.8851 -1.6572 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4612 0.6254 -1.3581 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8843 0.7525 -1.1529 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5247 -0.5283 -1.6406 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9602 0.7449 -1.9387 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8792 -1.3089 -0.4307 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7328 -1.6099 0.4847 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3850 -1.3428 0.0296 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8604 0.0459 -0.0646 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5037 -0.0583 -0.3054 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1136 0.9309 1.1005 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0003 2.3930 0.8046 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2454 2.6495 -0.4717 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0692 2.1727 -0.1680 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0449 4.1083 -0.6675 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1432 4.6829 -1.8391 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6863 4.9750 0.5301 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1862 2.9382 1.8313 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1457 0.5008 2.2134 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5501 -2.2548 0.8436 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3017 -3.2988 1.1428 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6350 -3.1265 0.5557 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4623 -3.9824 0.2093 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8956 -4.5033 1.9549 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0302 -1.2829 1.8107 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5797 -2.4461 -0.8345 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1709 -1.2738 -2.8431 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3425 -1.3520 -3.6464 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6828 -3.0493 -0.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5537 -2.0747 -1.7649 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1277 -2.5351 -0.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4291 -0.1092 -0.9020 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7980 -1.1410 -0.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9610 0.1713 1.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5964 -1.5736 1.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5444 -0.1365 2.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3427 -0.3936 -0.6472 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3691 0.2932 1.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1643 0.0175 -1.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0574 0.7426 0.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9033 0.4569 -2.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1718 2.4622 -2.4680 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1684 -0.1205 -2.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1800 1.0909 -0.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6115 -0.6947 0.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2763 -1.7733 -1.0057 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1139 0.8186 1.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9486 2.9498 0.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9753 5.7816 -1.8758 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3637 4.1565 -2.7378 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4332 5.9949 0.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5557 5.1383 1.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2256 4.6201 1.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3118 2.4329 1.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4902 -0.4912 2.6302 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1150 0.4086 1.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2574 1.1939 3.0874 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5280 -2.0801 1.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8029 -4.6756 1.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1591 -4.3851 3.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4167 -5.4135 1.5736 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9187 -0.8489 1.8696 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4388 -2.5565 -0.3564 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8375 -2.3090 -2.7367 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4383 -0.7856 -3.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8745 -2.1480 -3.4150 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 2 3 5 6 1 0 6 7 2 3 7 8 1 0 8 9 2 3 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 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 2 0 26 28 1 0 23 29 1 0 22 30 1 0 19 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 32 35 1 0 18 36 1 0 17 37 1 0 15 38 1 0 38 39 1 0 21 10 1 0 25 10 1 0 24 12 1 0 20 13 1 0 16 14 1 0 33 18 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 4 47 1 0 5 48 1 0 6 49 1 0 7 50 1 0 8 51 1 0 9 52 1 0 12 53 1 0 13 54 1 0 14 55 1 0 17 56 1 0 19 57 1 0 22 58 1 0 23 59 1 0 27 60 1 0 27 61 1 0 28 62 1 0 28 63 1 0 28 64 1 0 29 65 1 0 30 66 1 0 30 67 1 0 30 68 1 0 31 69 1 0 35 70 1 0 35 71 1 0 35 72 1 0 36 73 1 0 37 74 1 0 38 75 1 0 38 76 1 0 39 77 1 0 M END

Standard InCHIKey	TWWHDBCEIQHHFZ-ICEZPICISA-N
Standard InCHI	InChI=1S/C30H38O9/c1-6-7-8-9-10-11-12-13-27-37-24-20-23-26(15-31,36-23)25(34)28(35)19(14-17(4)21(28)32)30(20,39-27)18(5)22(33)29(24,38-27)16(2)3/h8-14,18-20,22-25,31,33-35H,2,6-7,15H2,1,3-5H3/b9-8-,11-10+,13-12+/t18-,19-,20+,22-,23+,24-,25-,26+,27-,28-,29-,30+/m1/s1
SMILES	CCCC=CC=CC=CC12OC3C4C5C(O5)(C(C6(C(C4(O1)C(C(C3(O2)C(=C)C)O)C)C=C(C6=O)C)O)O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	542.25	Volume:	539.391 ? Van der Waals volume.
Dense:	1.005	LogP:	4.227 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.95 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.374 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	29.0
TPSA:	138.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.215	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.052	Fsp³:	0.633
MCE-18:	107.061 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.161	Fluc inhibitor:	0.034 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.034 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.314 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.407	Promiscuous compounds:	0.035

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.176	MDCK Permeability:	-4.879
Pgp-inhibitor:	0.001	Pgp-substrate:	0.104
PAMPA:	0.892 ? 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):	0.121
20% Bioavailability (F20%):	0.197	30% Bioavailability (F30%):	0.89
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406	MRP1:	0.967
Plasma Protein Binding (PPB):	79.104%	Volume Distribution (VD):	-0.024
Fu:	23.815% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.185
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.022
BSEP inhibitor:	0.88

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.07	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.6	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.033	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.001
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):

4.6

Half-life (T1/2):

1.564

ADMET: Toxicity

hERG Blockers:	0.078	hERG Blockers (10um):	0.367
Human Hepatotoxicity (H-HT):	0.508	Drug-induced Liver Injury (DILI):	0.114
AMES Toxicity:	0.908	Rat Oral Acute Toxicity:	0.791
Maximum Recommended Daily Dose:	0.364	Skin Sensitization:	0.97
Carcinogencity:	0.148	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.338
Drug-induced Neurotoxicity:	0.669	Ototoxicity:	0.95
Hematotoxicity:	0.1	Drug-induced Nephrotoxicity:	0.061
Genotoxicity:	0.309	RPMI-8226 Immunitoxicity:	0.343
A549 Cytotoxicity:	0.034	Hek293 Cytotoxicity:	0.764
BCF:	1.394 ? 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:	3.996 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.822 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.05 ? 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
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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

Activity Type	# Activity
Activity	2

Activity Type	# Activity
Organism	2

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
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.81	nmol	PMID[17822299]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.2	/nmol	PMID[1593279]

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 NPC475606 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	18682
0.1-0.2	30560
0.2-0.3	530
0.3-0.4	18
0.4-0.5	20
0.5-0.6	16
0.6-0.7	25
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9143	High Similarity	NPC475314
0.9143	High Similarity	NPC102997
0.9014	High Similarity	NPC485693
0.7403	Intermediate Similarity	NPC324104
0.7403	Intermediate Similarity	NPC473548
0.7051	Intermediate Similarity	NPC251564
0.7051	Intermediate Similarity	NPC477189
0.6962	Remote Similarity	NPC474508
0.6962	Remote Similarity	NPC473485
0.6962	Remote Similarity	NPC171411
0.6962	Remote Similarity	NPC485701
0.679	Remote Similarity	NPC223356
0.679	Remote Similarity	NPC298697
0.679	Remote Similarity	NPC475500
0.679	Remote Similarity	NPC100017
0.679	Remote Similarity	NPC481742
0.6707	Remote Similarity	NPC182266
0.6707	Remote Similarity	NPC475154
0.6707	Remote Similarity	NPC485700
0.6707	Remote Similarity	NPC75831
0.6707	Remote Similarity	NPC471137
0.6627	Remote Similarity	NPC471136
0.6627	Remote Similarity	NPC116727
0.6627	Remote Similarity	NPC39509
0.6548	Remote Similarity	NPC481744
0.6548	Remote Similarity	NPC481743
0.6404	Remote Similarity	NPC164150
0.6404	Remote Similarity	NPC481754
0.6196	Remote Similarity	NPC130886
0.6173	Remote Similarity	NPC162495
0.6071	Remote Similarity	NPC180902
0.6064	Remote Similarity	NPC481774
0.5914	Remote Similarity	NPC92598
0.5914	Remote Similarity	NPC43304
0.5914	Remote Similarity	NPC481753
0.5914	Remote Similarity	NPC477188
0.5914	Remote Similarity	NPC477190
0.5729	Remote Similarity	NPC101786
0.5638	Remote Similarity	NPC68282
0.5612	Remote Similarity	NPC481773
0.5588	Remote Similarity	NPC191992
0.5517	Remote Similarity	NPC476078
0.5204	Remote Similarity	NPC486153
0.5189	Remote Similarity	NPC69240
0.5119	Remote Similarity	NPC475273
0.5119	Remote Similarity	NPC168849
0.5119	Remote Similarity	NPC217901
0.5119	Remote Similarity	NPC611341

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475606 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7019
0.1-0.2	2125
0.2-0.3	6
0.3-0.4	0
0.4-0.5	0
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