NPASS Compound

Natural Product: NPC154675

Natural Product ID	NPC154675
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KXQIRSPCAUQOEP-ZPMPWWEHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2376819
PubChem CID	73347309
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 73 79 0 0 0 0 0 0 0 0999 V2000 3.1714 -2.8076 -1.4111 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0876 -1.9916 -0.3850 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2119 -2.0913 0.6244 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0165 -1.0243 -0.1750 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3625 -1.3316 1.1542 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4045 -0.1990 1.5099 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2136 0.8750 2.2156 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3130 0.3605 0.3015 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6268 0.9888 0.6726 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6948 1.4908 2.1049 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1491 1.9951 2.0826 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6862 2.2061 3.4549 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8262 0.9156 1.3276 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0185 0.7520 1.2643 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8017 0.0666 0.6609 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2182 -0.5004 -0.6169 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5774 -0.0691 -1.8607 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4364 -0.2969 -3.1172 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6673 -0.6082 -4.2119 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1774 -0.3245 -1.9630 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4369 -0.7336 -0.7045 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9936 -1.0400 -1.2197 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2993 0.1470 -1.9345 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5846 1.0044 -0.8901 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1704 2.2414 -1.4704 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3098 2.3385 -2.8330 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8547 3.4775 -3.4370 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2680 4.5400 -2.6615 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1335 4.4527 -1.3069 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5907 3.3156 -0.7200 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 0.2946 -0.1346 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4781 1.4173 -0.1731 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6869 0.9472 -2.0077 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1361 -1.9151 -0.5632 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5138 -0.9605 1.5916 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7502 -2.5831 1.1580 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0693 -3.6391 1.9889 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9885 -3.4803 2.8234 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3686 -4.9589 1.9369 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0491 -3.4981 -1.4565 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4938 -2.9047 -2.2425 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1786 -2.0780 0.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1361 -3.0255 1.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1004 -1.2495 1.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1587 -1.3228 1.9245 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2923 -0.6658 2.2390 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1748 1.8475 1.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3030 0.5992 2.2694 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9044 0.9563 3.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8319 1.9346 0.0845 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0870 2.3985 2.2689 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6139 0.7301 2.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1691 2.9404 1.5228 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3327 1.4844 4.2045 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8013 2.2396 3.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3873 3.2285 3.7855 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3331 -0.3200 -0.7193 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9957 0.6695 -3.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2248 -1.0610 -2.9184 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5830 -1.6013 -4.2635 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7913 -0.6794 -2.9614 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8357 -1.6428 -0.2552 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9500 -1.8858 -1.9098 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0043 1.5396 -3.4911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9730 3.5740 -4.5069 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6962 5.4345 -3.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4659 5.3019 -0.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5050 3.2901 0.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0459 -2.2968 -1.4593 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4021 -1.2417 1.9623 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3733 -5.0654 2.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0102 -5.1728 0.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1669 -5.7287 2.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 4 2 1 6 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 18 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 24 31 1 0 24 32 1 0 20 33 1 0 16 34 1 0 15 35 1 1 5 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 22 4 1 0 30 25 1 0 31 4 1 0 21 8 1 0 8 32 1 6 15 9 1 0 33 17 1 0 1 40 1 0 1 41 1 0 3 42 1 0 3 43 1 0 3 44 1 0 5 45 1 1 6 46 1 1 7 47 1 0 7 48 1 0 7 49 1 0 9 50 1 6 10 51 1 0 10 52 1 0 11 53 1 6 12 54 1 0 12 55 1 0 12 56 1 0 16 57 1 6 18 58 1 0 18 59 1 0 19 60 1 0 20 61 1 6 21 62 1 1 22 63 1 6 26 64 1 0 27 65 1 0 28 66 1 0 29 67 1 0 30 68 1 0 34 69 1 0 35 70 1 0 39 71 1 0 39 72 1 0 39 73 1 0 M END

Standard InCHIKey	KXQIRSPCAUQOEP-ZPMPWWEHSA-N
Standard InCHI	InChI=1S/C29H34O10/c1-13(2)27-21(35-16(5)31)15(4)28-18-11-14(3)20(32)26(18,34)24(33)25(12-30)22(36-25)19(28)23(27)37-29(38-27,39-28)17-9-7-6-8-10-17/h6-10,14-15,18-19,21-24,30,33-34H,1,11-12H2,2-5H3/t14-,15+,18+,19-,21+,22-,23+,24+,25-,26+,27-,28-,29+/m0/s1
SMILES	C=C(C)[C@]12[C@@H]([C@@H](C)[C@]34[C@@H]5C[C@H](C)C(=O)[C@]5([C@@H]([C@]5(CO)[C@H]([C@H]3[C@H]1O[C@](c1ccccc1)(O2)O4)O5)O)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	542.22	Volume:	522.328 ? Van der Waals volume.
Dense:	1.038	LogP:	1.653 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.138 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.744 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	144.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	7.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.286	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.645	Fsp³:	0.655
MCE-18:	172.0 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.226	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.131	Promiscuous compounds:	0.447

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.38	MDCK Permeability:	-4.914
Pgp-inhibitor:	0.278	Pgp-substrate:	0.062
PAMPA:	0.002 ? 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):	0.0
20% Bioavailability (F20%):	0.007	30% Bioavailability (F30%):	0.751
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.939	MRP1:	0.994
Plasma Protein Binding (PPB):	62.185%	Volume Distribution (VD):	-0.191
Fu:	39.264% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.946
OATP1B3 inhibitor:	0.143	BCRP inhibitor:	0.34
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.014	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.021	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.028	CYP3A4-substrate:	0.02
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.598
HLM stability:	0.712 ? 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):

3.951

Half-life (T1/2):

1.112

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.15
Human Hepatotoxicity (H-HT):	0.529	Drug-induced Liver Injury (DILI):	0.13
AMES Toxicity:	0.781	Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.86	Skin Sensitization:	1.0
Carcinogencity:	0.252	Eye Corrosion:	0.001
Eye Irritation:	0.406	Respiratory Toxicity:	0.203
Drug-induced Neurotoxicity:	0.326	Ototoxicity:	0.766
Hematotoxicity:	0.559	Drug-induced Nephrotoxicity:	0.569
Genotoxicity:	0.828	RPMI-8226 Immunitoxicity:	0.308
A549 Cytotoxicity:	0.695	Hek293 Cytotoxicity:	0.744
BCF:	0.594 ? 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:	3.355 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.049 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.313 ? 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
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	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

Activity Type	# Activity
IC50	10

Activity Type	# Activity
Cell line	9
Non-molecular	1

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
NPT111	Cell line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[23558238]
NPT466	Cell line	U-937	Homo sapiens	IC50	>	50000.0	nM	PMID[23558238]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[23558238]
NPT453	Cell line	HT-1080	Homo sapiens	IC50	<	100.0	nM	PMID[23558238]
NPT81	Cell line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[23558238]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	>	50000.0	nM	PMID[23558238]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[23558238]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	23620.0	nM	PMID[23558238]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	50000.0	nM	PMID[23558238]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	14240.0	nM	PMID[23558238]

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 NPC154675 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	11485
0.1-0.2	36561
0.2-0.3	1706
0.3-0.4	74
0.4-0.5	14
0.5-0.6	7
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8158	Intermediate Similarity	NPC40138
0.7179	Intermediate Similarity	NPC181924
0.7	Intermediate Similarity	NPC325732
0.7	Intermediate Similarity	NPC324769
0.6627	Remote Similarity	NPC481750
0.6585	Remote Similarity	NPC481751
0.6386	Remote Similarity	NPC326328
0.6279	Remote Similarity	NPC479347
0.6154	Remote Similarity	NPC156682
0.6154	Remote Similarity	NPC49297
0.6136	Remote Similarity	NPC275477
0.5862	Remote Similarity	NPC61891
0.5595	Remote Similarity	NPC146310
0.5581	Remote Similarity	NPC323356
0.5444	Remote Similarity	NPC326235
0.5333	Remote Similarity	NPC323001
0.5222	Remote Similarity	NPC12491
0.5116	Remote Similarity	NPC322048

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC154675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3755
0.1-0.2	5305
0.2-0.3	90
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