NPASS Compound

Natural Product: NPC472991

Natural Product ID	NPC472991
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GDUKDXCFCUGUSD-MCXDURLZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3597469
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 70 74 0 0 0 0 0 0 0 0999 V2000 -0.2748 -5.8473 -2.2013 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3346 -4.9203 -1.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5576 -4.0971 -1.3540 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7753 -3.1185 -0.3772 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1803 -1.9276 -0.6942 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1633 -2.1187 -0.9465 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2607 -1.5478 -0.3942 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8778 -2.0927 0.7354 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3112 -3.2369 1.2557 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9964 -1.5149 1.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5475 -0.3621 0.7579 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9562 0.1892 -0.3521 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8313 -0.4038 -0.9094 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3014 0.2205 -2.0268 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5133 1.3350 -0.8846 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9725 1.8401 -1.9009 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6318 1.8768 -0.2871 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1719 1.2878 0.8080 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6142 0.1937 1.2909 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3461 1.8188 1.4708 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0145 2.9464 1.0731 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1286 3.4001 1.7433 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6254 2.7479 2.8411 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9746 1.6058 3.2694 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8713 1.1655 2.5976 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4809 0.9562 4.3743 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7471 3.1951 3.5242 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9447 -1.2167 -1.8091 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6105 -2.3508 -2.6355 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5847 -3.4437 -2.7398 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9229 -4.3813 -3.7146 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0109 -1.8547 -3.8688 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7381 -0.2702 -1.4622 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4529 0.7782 -1.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0319 1.7937 -1.9206 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5891 1.0013 -0.3253 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1727 2.1836 -0.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3058 2.4878 0.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9123 1.6001 1.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9991 1.9549 2.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4768 3.2465 2.2137 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8725 4.1618 1.3782 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8030 3.7780 0.5977 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5489 3.6192 3.0008 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2202 -6.6279 -1.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6160 -4.3922 -1.1402 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4152 -5.4511 -0.1745 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4376 -4.7688 -1.3184 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2614 -1.2272 0.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1718 -3.2600 2.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4544 -1.9719 2.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 0.9430 -1.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0506 2.7666 -0.7137 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 3.4971 0.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6139 4.2903 1.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3820 0.2633 2.9579 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4850 0.7634 4.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6386 3.3713 3.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1733 -0.8323 -2.5756 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4622 -2.6907 -1.9993 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6026 -2.9832 -2.9337 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3503 -5.1938 -3.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8460 -2.2386 -4.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9917 0.2261 0.2845 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7386 2.9611 -0.8740 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5502 0.5715 1.5035 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4637 1.2222 2.9087 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2903 5.1629 1.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3675 4.5354 -0.0387 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1601 4.3847 2.7102 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 2 0 8 9 1 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 12 15 1 0 15 16 2 0 15 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 5 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 41 44 1 0 30 3 1 0 43 38 1 0 13 7 1 0 25 20 1 0 19 11 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 6 5 49 1 1 9 50 1 0 10 51 1 0 14 52 1 0 17 53 1 0 21 54 1 0 22 55 1 0 25 56 1 0 26 57 1 0 27 58 1 0 28 59 1 6 29 60 1 1 30 61 1 6 31 62 1 0 32 63 1 0 36 64 1 0 37 65 1 0 39 66 1 0 40 67 1 0 42 68 1 0 43 69 1 0 44 70 1 0 M END

Standard InCHIKey	GDUKDXCFCUGUSD-MCXDURLZSA-N
Standard InCHI	InChI=1S/C30H26O14/c31-12-22-25(38)27(40)29(43-23(37)8-3-13-1-5-15(32)6-2-13)30(42-22)44-28-19(36)11-21-24(26(28)39)18(35)10-20(41-21)14-4-7-16(33)17(34)9-14/h1-11,22,25,27,29-34,36,38-40H,12H2/b8-3+/t22-,25-,27+,29-,30+/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2c(O)cc3c(c2O)c(=O)cc(o3)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.13	Volume:	573.443 ? Van der Waals volume.
Dense:	1.064	LogP:	1.172 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.266 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.137 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	236.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.084	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.336	Fsp³:	0.2
MCE-18:	108.167 ? 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:	0.88	Fluc inhibitor:	0.87 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.98 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.878 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.419	Promiscuous compounds:	0.914

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.345	MDCK Permeability:	-5.194
Pgp-inhibitor:	0.0	Pgp-substrate:	0.024
PAMPA:	0.957 ? 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):	0.12
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:	0.046
Plasma Protein Binding (PPB):	85.853%	Volume Distribution (VD):	-0.06
Fu:	11.793% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.168
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.047	CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.945
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.651 ? 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):

3.349

Half-life (T1/2):

2.865

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.242
Human Hepatotoxicity (H-HT):	0.667	Drug-induced Liver Injury (DILI):	0.975
AMES Toxicity:	0.872	Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.418	Skin Sensitization:	1.0
Carcinogencity:	0.26	Eye Corrosion:	0.0
Eye Irritation:	0.608	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.813
Hematotoxicity:	0.051	Drug-induced Nephrotoxicity:	0.157
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.874	Hek293 Cytotoxicity:	0.823
BCF:	0.679 ? 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:	3.501 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.762 ? 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
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356064]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283497]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	leaf	Putz City, Chiayi County, Taiwan	2009-Nov	PMID[25999202]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28742368]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29397715]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26700	Tinospora crispa	Species	Menispermaceae	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
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	35700.0	nM	PMID[21920741]

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 NPC472991 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	11157
0.1-0.2	33620
0.2-0.3	4007
0.3-0.4	832
0.4-0.5	190
0.5-0.6	41
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9157	High Similarity	NPC472992
0.7391	Intermediate Similarity	NPC477628
0.6078	Remote Similarity	NPC260504
0.6078	Remote Similarity	NPC89809
0.6038	Remote Similarity	NPC470712
0.5926	Remote Similarity	NPC470718
0.5888	Remote Similarity	NPC164704
0.5826	Remote Similarity	NPC480470
0.5741	Remote Similarity	NPC470715
0.5631	Remote Similarity	NPC139060
0.5577	Remote Similarity	NPC221288
0.5577	Remote Similarity	NPC194836
0.5577	Remote Similarity	NPC91493
0.5577	Remote Similarity	NPC605081
0.5575	Remote Similarity	NPC162394
0.5566	Remote Similarity	NPC218161
0.5566	Remote Similarity	NPC484301
0.5537	Remote Similarity	NPC249560
0.5517	Remote Similarity	NPC480472
0.5481	Remote Similarity	NPC210961
0.54	Remote Similarity	NPC8856
0.5391	Remote Similarity	NPC470720
0.5351	Remote Similarity	NPC470713
0.534	Remote Similarity	NPC115674
0.5339	Remote Similarity	NPC199172
0.5306	Remote Similarity	NPC80188
0.5306	Remote Similarity	NPC224530
0.5304	Remote Similarity	NPC470717
0.5278	Remote Similarity	NPC483767
0.5278	Remote Similarity	NPC483769
0.5278	Remote Similarity	NPC483768
0.5278	Remote Similarity	NPC483766
0.5263	Remote Similarity	NPC76047
0.5229	Remote Similarity	NPC483765
0.5208	Remote Similarity	NPC149011
0.514	Remote Similarity	NPC205824
0.5119	Remote Similarity	NPC100887
0.5094	Remote Similarity	NPC480471
0.5094	Remote Similarity	NPC488076
0.5094	Remote Similarity	NPC476619
0.5093	Remote Similarity	NPC477629
0.5047	Remote Similarity	NPC104883
0.5047	Remote Similarity	NPC488679
0.5041	Remote Similarity	NPC21359
0.5041	Remote Similarity	NPC460984
0.5041	Remote Similarity	NPC35924

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3705
0.1-0.2	5351
0.2-0.3	85
0.3-0.4	8
0.4-0.5	1
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