NPASS Compound

Natural Product: NPC264153

Natural Product ID	NPC264153
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Andrographiside
IUPAC Name	(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
Synonyms	Andrographiside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL519275
PubChem CID	44593583
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

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 76 79 0 0 0 0 0 0 0 0999 V2000 6.9412 1.0511 2.4968 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0886 0.1079 1.4877 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7855 -0.6398 1.2449 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7552 0.1961 0.8685 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9556 -0.3249 -0.1344 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9224 0.5499 -0.4057 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6574 -0.0778 -0.2639 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6498 0.9698 -0.5827 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9525 1.4074 -2.0307 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8414 2.1944 0.2705 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0693 2.1265 0.9599 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2684 2.4026 1.2665 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7779 1.1302 1.8752 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4316 0.3339 0.7373 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7737 0.6005 -0.5709 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1741 -0.5304 -1.4947 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6781 -0.4240 -1.6679 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2788 0.6729 -0.8462 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1319 1.5436 -1.3436 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8902 0.7769 0.5890 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8547 -0.0203 1.3938 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2104 0.5317 1.1491 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2276 -0.1383 0.6615 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2027 -1.5867 0.2631 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8728 -1.7148 -1.0810 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6796 -1.9489 0.3948 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3336 -0.7477 -0.0087 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5744 0.3354 0.3975 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9791 1.5015 0.5134 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3886 -1.1145 1.1784 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7946 -0.4308 -1.3914 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8968 -1.4035 -1.1458 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0277 -1.7748 0.2904 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2755 -2.9086 0.6392 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1173 -0.9457 -1.6883 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9347 -0.8672 -2.4068 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0746 0.9373 2.9994 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8237 -0.6428 1.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4954 0.5497 0.5565 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5021 -1.0899 2.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6280 -1.3305 0.1371 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6419 -0.3766 0.8183 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6579 -0.9171 -0.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0843 1.9679 -2.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1553 0.5385 -2.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8088 2.1129 -2.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8983 3.1268 -0.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7605 2.6900 0.5323 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1303 2.8967 0.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1258 3.0404 2.0806 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0368 0.5535 2.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5736 1.3883 2.5848 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2989 1.4991 -1.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6415 -0.4409 -2.4562 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8743 -1.5187 -1.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8613 -0.1864 -2.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1833 -1.3908 -1.4816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5490 2.3237 -0.7281 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4161 1.4720 -2.3851 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8857 1.8565 0.8658 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8808 -1.0866 1.0955 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6625 -0.0071 2.4815 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3746 1.5770 1.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5860 -2.1680 0.9459 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6361 -1.3718 -1.6041 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9249 -2.7471 -0.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9545 -2.1849 1.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3932 -1.5554 1.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6837 -1.1424 2.2696 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0450 -1.7770 0.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1347 0.5851 -1.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6810 -2.3535 -1.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1013 -2.0906 0.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6298 -3.6388 0.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8824 -0.1775 -2.2798 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4953 -0.9914 -3.2254 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 8 7 1 1 8 9 1 0 8 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 14 30 1 1 5 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 33 3 1 0 15 8 1 0 28 23 1 0 20 14 1 0 1 37 1 0 2 38 1 0 2 39 1 0 3 40 1 1 5 41 1 1 7 42 1 0 7 43 1 0 9 44 1 0 9 45 1 0 9 46 1 0 10 47 1 6 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 15 53 1 6 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 19 58 1 0 19 59 1 0 20 60 1 1 21 61 1 0 21 62 1 0 22 63 1 0 24 64 1 1 25 65 1 0 26 66 1 0 26 67 1 0 30 68 1 0 30 69 1 0 30 70 1 0 31 71 1 6 32 72 1 6 33 73 1 6 34 74 1 0 35 75 1 0 36 76 1 0 M END

Standard InCHIKey	VUEPOIYXKZTLMD-ANZZXSATSA-N
Standard InCHI	InChI=1S/C26H40O10/c1-13-4-7-18-25(2,15(13)6-5-14-16(28)11-34-23(14)33)9-8-19(29)26(18,3)12-35-24-22(32)21(31)20(30)17(10-27)36-24/h5,15-22,24,27-32H,1,4,6-12H2,2-3H3/b14-5+/t15-,16-,17-,18+,19-,20-,21+,22-,24-,25+,26+/m1/s1
SMILES	OC[C@H]1O[C@@H](OC[C@]2(C)[C@H](O)CC[C@@]3([C@@H]2CCC(=C)[C@H]3C/C=C/2[C@H](O)COC2=O)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.26	Volume:	504.019 ? Van der Waals volume.
Dense:	1.016	LogP:	0.789 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.527 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.871 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	25.0
TPSA:	166.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.217	Fsp³:	0.808
MCE-18:	80.426 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.599	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.195	Promiscuous compounds:	0.078

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.75	MDCK Permeability:	-5.065
Pgp-inhibitor:	0.001	Pgp-substrate:	0.009
PAMPA:	0.971 ? 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):	0.045
20% Bioavailability (F20%):	0.107	30% Bioavailability (F30%):	0.971
50% Bioavailability (F50%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	0.053
Plasma Protein Binding (PPB):	73.106%	Volume Distribution (VD):	-0.539
Fu:	25.492% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.029
BSEP inhibitor:	0.094

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.015
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.157
HLM stability:	0.807 ? 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):

2.224

Half-life (T1/2):

2.228

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.856	Drug-induced Liver Injury (DILI):	0.611
AMES Toxicity:	0.914	Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.789	Skin Sensitization:	1.0
Carcinogencity:	0.823	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.082
Drug-induced Neurotoxicity:	0.09	Ototoxicity:	0.986
Hematotoxicity:	0.774	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.426
A549 Cytotoxicity:	0.949	Hek293 Cytotoxicity:	0.808
BCF:	0.629 ? 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:	3.415 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.144 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.265 ? 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
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1111/ppl.12252]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	root	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	aerial parts	purchased in Juhuacun herbal market, Kunming, Yunnan Province, China	2002-Oct	PMID[16562826]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18357994]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21598983]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22026410]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377022]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3578	Andrographis paniculata	Species	Acanthaceae	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
GI50	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
NPT116	Cell line	HL-60	Homo sapiens	GI50	=	28830.0	nM	PMID[18357994]

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 NPC264153 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	16562
0.1-0.2	24415
0.2-0.3	7489
0.3-0.4	1315
0.4-0.5	56
0.5-0.6	15
0.6-0.7	4
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
0.7465	Intermediate Similarity	NPC599990
0.6471	Remote Similarity	NPC159763
0.6471	Remote Similarity	NPC278386
0.6471	Remote Similarity	NPC124512
0.6133	Remote Similarity	NPC305160
0.5823	Remote Similarity	NPC392
0.5823	Remote Similarity	NPC177524
0.5823	Remote Similarity	NPC219900
0.5789	Remote Similarity	NPC240372
0.575	Remote Similarity	NPC479455
0.575	Remote Similarity	NPC479454
0.5571	Remote Similarity	NPC79027
0.5256	Remote Similarity	NPC72817
0.525	Remote Similarity	NPC272576
0.5181	Remote Similarity	NPC479461
0.5068	Remote Similarity	NPC478375
0.5067	Remote Similarity	NPC72845
0.5067	Remote Similarity	NPC242848
0.5063	Remote Similarity	NPC73911
0.5059	Remote Similarity	NPC484732

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC264153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6065
0.1-0.2	2945
0.2-0.3	130
0.3-0.4	8
0.4-0.5	0
0.5-0.6	1
0.6-0.7	1
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
0.6471	Remote Similarity	NPD4225	Phase 3
0.5823	Remote Similarity	NPD6686	Approved

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