NPASS Compound

Natural Product: NPC298692

Natural Product ID	NPC298692
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Schizolaenone B
IUPAC Name	(2S)-2-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-4,5-dihydroxyphenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL479869
PubChem CID	11466031
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

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 72 74 0 0 0 0 0 0 0 0999 V2000 -10.1314 -0.1111 0.2080 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9479 -0.9484 -0.0912 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6821 -0.4883 -0.0544 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5484 -1.3556 -0.3583 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5629 -1.6115 0.7145 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8646 -0.4251 1.2430 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5300 -0.3542 1.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8160 0.8197 1.6418 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9761 1.3793 0.5353 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5997 1.1657 0.5218 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2161 1.6583 -0.4746 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4090 2.3816 -1.4675 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7696 2.6044 -1.4728 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5836 2.0989 -0.4565 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9626 2.3496 -0.5015 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3891 3.3326 -2.4748 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 1.4150 -0.4524 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3343 1.7202 -1.7697 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6196 1.0240 -1.9839 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3112 1.2727 -3.0064 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1123 0.0466 -1.0320 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2519 -0.4251 -0.0679 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7079 -1.3524 0.8402 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0097 -1.8047 0.7867 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8918 -1.3470 -0.1705 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3022 -1.8348 -0.2299 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1435 -1.2340 0.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2395 -0.5002 0.5843 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0170 0.0608 1.7327 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7306 -0.2138 -0.7880 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4208 -0.4192 -1.0722 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2279 0.1030 -2.0730 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4509 -2.7285 1.6975 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9527 0.0616 -0.0574 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5624 0.6555 1.9388 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1699 -2.3753 -0.4520 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9089 0.7603 0.8455 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8481 -0.7725 0.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6643 0.2536 -0.6788 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6047 0.5597 0.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0484 -0.9805 -1.2901 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9633 -2.3620 -0.6707 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8183 -2.3723 0.3350 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0767 -2.1553 1.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9527 -1.1351 0.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1202 0.4888 2.4517 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4570 1.6581 1.9652 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1673 0.5965 1.3189 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1980 2.7971 -2.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3400 3.2586 -0.7545 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6099 2.9212 -3.3651 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1746 2.0551 0.3108 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5460 2.8115 -1.8792 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6551 1.4375 -2.6043 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0132 -1.7142 1.5962 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3122 -2.9472 -0.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6586 -1.6694 -1.2647 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8491 -1.4008 1.8513 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3615 0.1457 2.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9242 -0.5390 1.8969 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3857 1.0721 1.4003 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9081 -0.0906 -1.5199 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3716 -1.0782 -1.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3725 0.6847 -0.7544 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0892 -0.3089 -3.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7558 -2.5237 2.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0773 0.9364 2.9075 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5569 0.2318 2.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7843 1.5281 1.3183 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6308 -2.9937 0.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2475 -2.6347 -0.4105 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8142 -2.6076 -1.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 13 16 1 0 11 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 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 2 3 28 29 1 0 28 30 1 0 25 31 2 0 31 32 1 0 24 33 1 0 22 34 1 0 6 35 1 0 2 36 1 0 14 9 1 0 34 17 1 0 31 21 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 10 48 1 0 12 49 1 0 15 50 1 0 16 51 1 0 17 52 1 1 18 53 1 0 18 54 1 0 23 55 1 0 26 56 1 0 26 57 1 0 27 58 1 0 29 59 1 0 29 60 1 0 29 61 1 0 30 62 1 0 30 63 1 0 30 64 1 0 32 65 1 0 33 66 1 0 35 67 1 0 35 68 1 0 35 69 1 0 36 70 1 0 36 71 1 0 36 72 1 0 M END

Standard InCHIKey	LFIGQOMCYZOIQK-XBPZWBIKSA-N
Standard InCHI	InChI=1S/C30H36O6/c1-17(2)7-6-8-19(5)10-11-20-13-21(14-25(33)29(20)34)26-16-24(32)28-27(36-26)15-23(31)22(30(28)35)12-9-18(3)4/h7,9-10,13-15,26,31,33-35H,6,8,11-12,16H2,1-5H3/b19-10+/t26-/m0/s1
SMILES	CC(=CCC/C(=C/Cc1cc(cc(c1O)O)[C@@H]1CC(=O)c2c(cc(c(CC=C(C)C)c2O)O)O1)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	492.25	Volume:	528.143 ? Van der Waals volume.
Dense:	0.932	LogP:	7.464 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.417 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.392 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	21.0
TPSA:	107.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.234	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.799	Fsp³:	0.367
MCE-18:	71.244 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.994	Fluc inhibitor:	0.701 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.538 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.69 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.548	Promiscuous compounds:	0.158

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.989	MDCK Permeability:	-4.731
Pgp-inhibitor:	0.943	Pgp-substrate:	0.0
PAMPA:	0.072 ? 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):	0.027
20% Bioavailability (F20%):	0.97	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.789
Plasma Protein Binding (PPB):	96.266%	Volume Distribution (VD):	0.122
Fu:	3.798% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.981
BSEP inhibitor:	0.891

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.28	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.967
CYP3A4-inhibitor:	0.112	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

7.953

Half-life (T1/2):

1.229

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.61
Human Hepatotoxicity (H-HT):	0.896	Drug-induced Liver Injury (DILI):	0.934
AMES Toxicity:	0.493	Rat Oral Acute Toxicity:	0.919
Maximum Recommended Daily Dose:	0.813	Skin Sensitization:	0.997
Carcinogencity:	0.215	Eye Corrosion:	0.0
Eye Irritation:	0.546	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.632	Ototoxicity:	0.79
Hematotoxicity:	0.273	Drug-induced Nephrotoxicity:	0.955
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.316
A549 Cytotoxicity:	0.973	Hek293 Cytotoxicity:	0.774
BCF:	2.198 ? 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:	5.698 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.453 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.102 ? 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
NPO16269	Schizolaena hystrix	Species	Sarcolaenaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[15787448]
NPO16269	Schizolaena hystrix	Species	Sarcolaenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15787448]
NPO16269	Schizolaena hystrix	Species	Sarcolaenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16269	Schizolaena hystrix	Species	Sarcolaenaceae	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	1

Activity Type	# Activity
Cell line	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
NPT179	Cell line	A2780	Homo sapiens	IC50	=	11.0	ug.mL-1	PMID[15787448]

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 NPC298692 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	20104
0.1-0.2	26440
0.2-0.3	2645
0.3-0.4	517
0.4-0.5	87
0.5-0.6	36
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8116	Intermediate Similarity	NPC185276
0.8088	Intermediate Similarity	NPC213896
0.7681	Intermediate Similarity	NPC290133
0.7534	Intermediate Similarity	NPC45849
0.7465	Intermediate Similarity	NPC164272
0.7465	Intermediate Similarity	NPC470327
0.7429	Intermediate Similarity	NPC228504
0.7324	Intermediate Similarity	NPC64915
0.726	Intermediate Similarity	NPC278778
0.7222	Intermediate Similarity	NPC470328
0.7222	Intermediate Similarity	NPC209614
0.7067	Intermediate Similarity	NPC472626
0.7067	Intermediate Similarity	NPC210459
0.7027	Intermediate Similarity	NPC226025
0.6842	Remote Similarity	NPC195796
0.6812	Remote Similarity	NPC125855
0.6571	Remote Similarity	NPC106976
0.6447	Remote Similarity	NPC261063
0.642	Remote Similarity	NPC321399
0.6377	Remote Similarity	NPC1089
0.6364	Remote Similarity	NPC321779
0.6234	Remote Similarity	NPC22192
0.6154	Remote Similarity	NPC74924
0.6111	Remote Similarity	NPC166689
0.6049	Remote Similarity	NPC488555
0.6049	Remote Similarity	NPC484418
0.5974	Remote Similarity	NPC472629
0.5897	Remote Similarity	NPC488556
0.5875	Remote Similarity	NPC488554
0.5823	Remote Similarity	NPC472627
0.5823	Remote Similarity	NPC58805
0.5802	Remote Similarity	NPC488557
0.5789	Remote Similarity	NPC35038
0.575	Remote Similarity	NPC488558
0.575	Remote Similarity	NPC470326
0.5696	Remote Similarity	NPC262039
0.5679	Remote Similarity	NPC472628
0.5679	Remote Similarity	NPC472630
0.5676	Remote Similarity	NPC223500
0.5658	Remote Similarity	NPC223787
0.5641	Remote Similarity	NPC96408
0.5641	Remote Similarity	NPC610511
0.561	Remote Similarity	NPC282009
0.561	Remote Similarity	NPC472631
0.557	Remote Similarity	NPC279650
0.5556	Remote Similarity	NPC258630
0.5542	Remote Similarity	NPC472598
0.5455	Remote Similarity	NPC470890
0.5412	Remote Similarity	NPC474055
0.5375	Remote Similarity	NPC470802
0.5366	Remote Similarity	NPC67396
0.5357	Remote Similarity	NPC27337
0.5349	Remote Similarity	NPC472634
0.5349	Remote Similarity	NPC293319
0.5309	Remote Similarity	NPC267375
0.5294	Remote Similarity	NPC287328
0.525	Remote Similarity	NPC484416
0.5244	Remote Similarity	NPC299436
0.519	Remote Similarity	NPC24136
0.5181	Remote Similarity	NPC201800
0.5132	Remote Similarity	NPC109223
0.5132	Remote Similarity	NPC10937

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC298692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4625
0.1-0.2	4483
0.2-0.3	35
0.3-0.4	7
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