NPASS Compound

Natural Product: NPC479667

Natural Product ID	NPC479667
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MEAHVVNSTHAEJW-AIALLWDPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14314212
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

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 4.0004 -2.7829 -0.4484 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2390 -1.4408 -0.5321 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1015 -0.4238 0.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4497 -0.3383 -0.5884 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2197 0.7200 0.1591 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5218 1.7127 -0.6424 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2829 2.9216 -0.2120 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9971 1.4220 -1.9674 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1304 2.1920 -2.9505 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3691 0.1878 -1.8735 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1793 -1.4950 -0.4612 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9115 -1.7027 0.0358 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8613 -2.1889 1.4651 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4102 -1.9247 1.9133 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 -1.4206 0.6644 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6382 -2.5714 -0.1720 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3653 -0.4825 0.8649 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2336 -0.7209 1.8526 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3606 0.2838 1.9997 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9532 0.3280 0.6087 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3476 0.8205 0.5189 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6532 2.0936 1.2246 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2498 -0.2744 1.1007 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6989 0.8577 -0.9480 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6697 1.5111 -1.2587 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8367 0.1022 -1.8627 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3514 0.4550 -1.7452 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0125 0.9648 -0.3768 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2089 2.4915 -0.4577 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5845 0.7296 0.0505 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5978 0.9574 -1.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5503 0.0407 -1.1650 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9201 -0.5912 0.1057 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3181 0.4333 1.1186 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2579 -3.6330 -0.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6110 -2.9669 -1.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5438 -2.8387 0.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1867 -1.2652 -1.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3046 -0.7164 1.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6880 0.6104 0.0646 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4580 0.6185 1.2036 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0562 2.6127 0.5455 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8356 3.3850 -1.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5820 3.5943 0.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7789 -1.6606 -1.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3821 -2.5361 -0.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5404 -1.7074 2.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0212 -3.2901 1.5287 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3610 -1.2456 2.7585 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0823 -2.8739 2.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4972 -2.4775 -1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7547 -2.7127 -0.0405 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2156 -3.5468 0.1441 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1265 -1.5733 2.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9838 1.2595 2.3371 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1147 -0.1571 2.6687 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9988 -0.7631 0.2816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7972 2.6417 1.6222 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3531 1.9228 2.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2754 2.7320 0.5301 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2414 -0.1384 0.6578 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8584 -1.2539 0.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3124 -0.1467 2.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9883 -0.9991 -1.6799 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1993 0.2706 -2.9128 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8065 -0.4729 -1.9943 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1739 1.2372 -2.5279 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2229 2.7752 -0.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5477 2.7913 -1.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7521 2.9551 0.4203 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3946 1.5700 0.8054 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2441 2.0320 -1.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1803 0.8826 -2.0039 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4449 -0.6869 -2.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4486 0.6473 -1.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4902 0.6632 1.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5052 1.3907 0.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1754 0.2035 1.7446 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 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 4 11 1 0 2 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 1 10 4 1 0 33 12 1 0 33 15 1 0 30 17 1 0 28 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 6 3 39 1 0 3 40 1 0 5 41 1 0 7 42 1 0 7 43 1 0 7 44 1 0 11 45 1 0 12 46 1 6 13 47 1 0 13 48 1 0 14 49 1 0 14 50 1 0 16 51 1 0 16 52 1 0 16 53 1 0 18 54 1 0 19 55 1 0 19 56 1 0 20 57 1 6 22 58 1 0 22 59 1 0 22 60 1 0 23 61 1 0 23 62 1 0 23 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 27 67 1 0 29 68 1 0 29 69 1 0 29 70 1 0 30 71 1 1 31 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 M END

Standard InCHIKey	MEAHVVNSTHAEJW-AIALLWDPSA-N
Standard InCHI	InChI=1S/C30H44O4/c1-18(16-30(33)17-19(2)25(32)34-30)20-10-14-29(7)22-8-9-23-26(3,4)24(31)12-13-27(23,5)21(22)11-15-28(20,29)6/h8,17-18,20-21,23,33H,9-16H2,1-7H3/t18-,20-,21-,23+,27-,28-,29+,30?/m1/s1
SMILES	C[C@H](CC1(C=C(C)C(=O)O1)O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)[C@@H]3CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.32	Volume:	509.269 ? Van der Waals volume.
Dense:	0.92	LogP:	4.278 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.929 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.364 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.386	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.107	Fsp³:	0.8
MCE-18:	97.111 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.7	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.464	Promiscuous compounds:	0.469

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.688	MDCK Permeability:	-4.552
Pgp-inhibitor:	0.824	Pgp-substrate:	0.0
PAMPA:	0.538 ? 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%):	0.036	30% Bioavailability (F30%):	0.243
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	0.966
Plasma Protein Binding (PPB):	92.885%	Volume Distribution (VD):	0.33
Fu:	8.066% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.072
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.947	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.081	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.493
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	1.0
HLM stability:	0.954 ? 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):

8.228

Half-life (T1/2):

0.543

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.337
Human Hepatotoxicity (H-HT):	0.624	Drug-induced Liver Injury (DILI):	0.518
AMES Toxicity:	0.261	Rat Oral Acute Toxicity:	0.423
Maximum Recommended Daily Dose:	0.724	Skin Sensitization:	0.947
Carcinogencity:	0.787	Eye Corrosion:	0.017
Eye Irritation:	0.457	Respiratory Toxicity:	0.694
Drug-induced Neurotoxicity:	0.576	Ototoxicity:	0.463
Hematotoxicity:	0.538	Drug-induced Nephrotoxicity:	0.83
Genotoxicity:	0.849	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.175	Hek293 Cytotoxicity:	0.473
BCF:	1.832 ? 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:	4.319 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.674 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.203 ? 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
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	trunk	n.a.	n.a.	PMID[24224862]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	Trunk	n.a.	n.a.	PMID[26812172]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30063340]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29383	Abies holophylla	Species	Pinaceae	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	5
Activity	1

Activity Type	# Activity
Cell line	6

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
NPT34	Cell line	BV-2	Mus musculus	IC50	=	10200.0	nM	PMID[30063340]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[30063340]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	=	4100.0	nM	PMID[30063340]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[30063340]
NPT81	Cell line	A549	Homo sapiens	IC50	=	9400.0	nM	PMID[30063340]
NPT34	Cell line	BV-2	Mus musculus	Activity	=	15.9	%	PMID[30063340]

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 NPC479667 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	22273
0.1-0.2	23019
0.2-0.3	4146
0.3-0.4	311
0.4-0.5	68
0.5-0.6	27
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
0.6567	Remote Similarity	NPC90652
0.6567	Remote Similarity	NPC155255
0.6567	Remote Similarity	NPC260992
0.6522	Remote Similarity	NPC486521
0.6522	Remote Similarity	NPC262870
0.6462	Remote Similarity	NPC470078
0.6324	Remote Similarity	NPC470052
0.6286	Remote Similarity	NPC471224
0.6286	Remote Similarity	NPC479662
0.6269	Remote Similarity	NPC470223
0.6232	Remote Similarity	NPC470047
0.6232	Remote Similarity	NPC470046
0.6087	Remote Similarity	NPC470417
0.5974	Remote Similarity	NPC484792
0.5972	Remote Similarity	NPC67831
0.5972	Remote Similarity	NPC174051
0.589	Remote Similarity	NPC605437
0.5867	Remote Similarity	NPC73506
0.5769	Remote Similarity	NPC189282
0.5769	Remote Similarity	NPC237402
0.5753	Remote Similarity	NPC470050
0.5753	Remote Similarity	NPC472239
0.5753	Remote Similarity	NPC470051
0.5733	Remote Similarity	NPC273669
0.5733	Remote Similarity	NPC484802
0.5733	Remote Similarity	NPC118647
0.5714	Remote Similarity	NPC63023
0.5714	Remote Similarity	NPC121566
0.5714	Remote Similarity	NPC100955
0.5714	Remote Similarity	NPC95243
0.5676	Remote Similarity	NPC6190
0.56	Remote Similarity	NPC293081
0.5333	Remote Similarity	NPC484798
0.5278	Remote Similarity	NPC82902
0.5211	Remote Similarity	NPC247220
0.5135	Remote Similarity	NPC2983
0.5135	Remote Similarity	NPC469994
0.5068	Remote Similarity	NPC474218
0.5067	Remote Similarity	NPC147066
0.5065	Remote Similarity	NPC154101

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7342
0.1-0.2	1662
0.2-0.3	145
0.3-0.4	1
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