NPASS Compound

Natural Product: NPC476027

Natural Product ID	NPC476027
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2S,3R)-5-Ethyl-2,3-Dihydroxy-6-(Hydroxymethyl)Hept-6-En-2-Yl]-2,3,14-Trihydroxy-10,13-Dimethyl-2,3,4,5,9,11,12,15,16,17-Decahydro-1H-Cyclopenta[A]Phenanthren-6-One
IUPAC Name	(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2S,3R)-5-ethyl-2,3-dihydroxy-6-(hydroxymethyl)hept-6-en-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL522368
PubChem CID	44566371
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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 82 85 0 0 0 0 0 0 0 0999 V2000 -4.5467 2.8782 0.5709 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6072 2.0125 -0.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1575 0.9322 -0.9428 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4345 0.2618 -1.4580 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8024 0.5331 -2.7024 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2219 -0.6645 -0.6316 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7376 -0.1152 0.5332 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2732 -0.1415 -0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8938 0.0054 -0.0854 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2653 -1.3757 0.1863 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9453 -1.3437 0.8303 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4795 -2.8196 1.0432 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0213 -2.8125 0.8309 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2969 -1.3615 1.0987 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2352 -0.7817 0.1456 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4441 -1.3427 -1.2425 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4627 0.6776 0.1582 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8529 0.9277 -0.4578 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9475 0.4458 0.4567 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6415 -0.8937 0.9405 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6337 -1.6998 1.2721 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0384 -1.3173 1.1507 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9811 -2.0511 1.5264 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3608 0.0027 0.5542 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2276 0.4579 -0.3335 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1634 -0.5281 -1.4734 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4557 1.8681 -0.8470 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8903 2.2561 -0.6827 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7334 1.5198 -1.5409 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3155 2.2167 0.7470 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6879 1.0713 1.5363 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7097 2.1318 0.8050 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8063 -1.1476 2.4249 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3762 -2.1588 -0.9544 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2311 -2.0074 1.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6975 0.6606 1.0908 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3886 2.6787 1.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8762 3.9735 0.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6220 2.9273 -0.0372 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3943 1.7261 0.6785 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2024 2.7272 -0.7204 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7740 1.4660 -1.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2282 1.2035 -3.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7054 0.0631 -3.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6605 -1.6027 -0.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1086 -1.0276 -1.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4805 0.4913 0.3352 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7812 -0.8308 0.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2271 -0.8475 -1.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2716 0.4738 -0.8606 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0096 -0.9259 1.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9093 -3.4583 0.2731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6585 -3.1374 2.0734 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3258 -3.1486 -0.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5234 -3.4839 1.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1050 -2.2995 -1.3874 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5044 -1.5777 -1.4399 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1311 -0.5616 -1.9685 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4776 1.0677 1.2127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1785 1.3004 -0.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8463 0.4246 -1.4199 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9452 2.0158 -0.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0137 1.1797 1.3126 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4574 -2.7057 1.6588 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2926 -0.1744 -0.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2035 -0.5920 -1.9020 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 -0.2267 -2.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8573 -1.5401 -1.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8593 2.5999 -0.2447 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1584 1.8849 -1.9003 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0175 3.3234 -1.0581 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6510 1.4518 -1.1794 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0500 3.1783 1.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4772 0.7390 2.2622 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8542 1.4540 2.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0251 2.1629 1.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9619 -1.9695 2.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3681 -1.6165 -1.7774 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6774 -1.2168 1.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9723 -2.6478 0.7206 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6677 -2.6583 1.9201 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1239 1.4395 1.0980 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 2 0 4 6 1 0 6 7 1 0 3 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 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 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 14 33 1 1 10 34 1 6 10 35 1 0 9 36 1 0 15 11 1 0 25 19 1 0 20 14 1 0 31 24 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 2 41 1 0 3 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 9 50 1 6 11 51 1 1 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 16 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 1 21 64 1 0 24 65 1 6 26 66 1 0 26 67 1 0 26 68 1 0 27 69 1 0 27 70 1 0 28 71 1 6 29 72 1 0 30 73 1 1 31 74 1 0 31 75 1 0 32 76 1 0 33 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 36 82 1 0 M END

Standard InCHIKey	ODENAQIZHMFEAO-TYVXGIJNSA-N
Standard InCHI	InChI=1S/C29H46O7/c1-6-17(16(2)15-30)11-25(34)28(5,35)24-8-10-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,3)18(19)7-9-27(24,29)4/h12,17-18,20,22-25,30,32-36H,2,6-11,13-15H2,1,3-5H3/t17?,18-,20-,22+,23-,24-,25+,26+,27+,28-,29+/m0/s1
SMILES	CCC(C(=C)CO)C[C@H]([C@]([C@H]1CC[C@@]2([C@]1(C)CC[C@H]1C2=CC(=O)[C@H]2[C@]1(C)C[C@H](O)[C@@H](C2)O)O)(O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	506.32	Volume:	529.536 ? Van der Waals volume.
Dense:	0.956	LogP:	2.062 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.531 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.559 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	22.0
TPSA:	138.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.291	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.429	Fsp³:	0.828
MCE-18:	85.962 ? 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:	0.334	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.335	Promiscuous compounds:	0.287

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.788	MDCK Permeability:	-4.631
Pgp-inhibitor:	0.0	Pgp-substrate:	0.389
PAMPA:	1.0 ? 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):	0.003
20% Bioavailability (F20%):	0.446	30% Bioavailability (F30%):	0.292
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.219
Plasma Protein Binding (PPB):	72.081%	Volume Distribution (VD):	-0.005
Fu:	33.767% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.549
BSEP inhibitor:	0.356

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.718	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.108
HLM stability:	0.345 ? 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):

5.692

Half-life (T1/2):

2.356

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.245
Human Hepatotoxicity (H-HT):	0.651	Drug-induced Liver Injury (DILI):	0.01
AMES Toxicity:	0.093	Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.735	Skin Sensitization:	0.621
Carcinogencity:	0.729	Eye Corrosion:	0.0
Eye Irritation:	0.08	Respiratory Toxicity:	0.21
Drug-induced Neurotoxicity:	0.042	Ototoxicity:	0.955
Hematotoxicity:	0.177	Drug-induced Nephrotoxicity:	0.814
Genotoxicity:	0.421	RPMI-8226 Immunitoxicity:	0.088
A549 Cytotoxicity:	0.019	Hek293 Cytotoxicity:	0.275
BCF:	0.506 ? 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:	3.291 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.123 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.035 ? 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
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	flowering whole plant	n.a.	n.a.	PMID[10425119]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748375]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17539	Ajuga decumbens	Species	Lamiaceae	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
Activity	8

Activity Type	# Activity
Cell line	4
Others	4

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PubChem BioAssay data set
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[23398362]
NPT2	Others	Unspecified	n.a.	Activity	=	49.1	%	PMID[10560729]
NPT2	Others	Unspecified	n.a.	Activity	=	95.8	%	PMID[10560729]
NPT2	Others	Unspecified	n.a.	Activity	=	72.6	%	PMID[24900585]
NPT2	Others	Unspecified	n.a.	Activity	=	4.6	%	PMID[17158936]

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 NPC476027 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	19243
0.1-0.2	28208
0.2-0.3	2341
0.3-0.4	12
0.4-0.5	8
0.5-0.6	12
0.6-0.7	13
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8226	Intermediate Similarity	NPC296945
0.8065	Intermediate Similarity	NPC214264
0.8065	Intermediate Similarity	NPC475060
0.8065	Intermediate Similarity	NPC85829
0.7778	Intermediate Similarity	NPC50692
0.7778	Intermediate Similarity	NPC260268
0.7778	Intermediate Similarity	NPC48733
0.7778	Intermediate Similarity	NPC171137
0.7778	Intermediate Similarity	NPC152695
0.7778	Intermediate Similarity	NPC319077
0.7778	Intermediate Similarity	NPC83744
0.7778	Intermediate Similarity	NPC97202
0.7778	Intermediate Similarity	NPC601752
0.7692	Intermediate Similarity	NPC202167
0.7692	Intermediate Similarity	NPC49958
0.7656	Intermediate Similarity	NPC220229
0.7656	Intermediate Similarity	NPC601682
0.7353	Intermediate Similarity	NPC49492
0.7353	Intermediate Similarity	NPC266728
0.7	Intermediate Similarity	NPC600136
0.6818	Remote Similarity	NPC302607
0.6714	Remote Similarity	NPC207251
0.6571	Remote Similarity	NPC317210
0.6351	Remote Similarity	NPC109973
0.6232	Remote Similarity	NPC76084
0.6176	Remote Similarity	NPC150531
0.6087	Remote Similarity	NPC204833
0.6087	Remote Similarity	NPC209502
0.6087	Remote Similarity	NPC477915
0.6087	Remote Similarity	NPC600374
0.6053	Remote Similarity	NPC475041
0.6	Remote Similarity	NPC329417
0.6	Remote Similarity	NPC149047
0.5857	Remote Similarity	NPC11710
0.5857	Remote Similarity	NPC217201
0.5857	Remote Similarity	NPC451956
0.5857	Remote Similarity	NPC610677
0.5672	Remote Similarity	NPC603391
0.5526	Remote Similarity	NPC250109
0.5443	Remote Similarity	NPC600372
0.5357	Remote Similarity	NPC28532
0.5325	Remote Similarity	NPC606024
0.5128	Remote Similarity	NPC326542
0.5068	Remote Similarity	NPC108721
0.5068	Remote Similarity	NPC73300

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6788
0.1-0.2	2244
0.2-0.3	118
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