NPASS Compound

Natural Product: NPC273668

Natural Product ID	NPC273668
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JIXNEPDMGSNJOM-AUBQSUGRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3632935
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 97101 0 0 0 0 0 0 0 0999 V2000 -8.0884 0.2695 2.7465 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4077 1.5426 2.4531 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3181 1.5828 1.7152 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7292 0.3604 1.1495 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2399 -0.7713 1.3473 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5962 0.4024 0.3811 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9752 -0.7412 -0.1955 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1544 -0.6503 -1.6489 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0590 -1.0705 -2.5530 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2772 0.0421 -3.1865 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7067 -1.8151 -3.7423 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2562 -2.0869 -1.8146 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6212 -1.6119 -0.5433 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5918 -0.9552 0.3677 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8314 -1.8612 1.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4229 -3.0534 1.2027 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1599 0.3517 0.9386 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6154 1.4777 0.2658 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7041 0.4516 1.3332 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6315 1.8176 1.7327 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1778 0.1728 0.1987 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2873 -0.9840 -0.6628 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5679 -1.4676 -1.5482 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9451 -0.9666 -1.8063 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4076 -0.1610 -0.6681 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6083 -0.2647 0.5990 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4541 -1.6974 1.0723 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1435 0.5128 1.7397 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6141 0.7424 1.7793 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2506 0.9016 0.4183 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9277 -0.2576 -0.4349 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3560 -1.5905 0.0318 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5722 0.0007 -1.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0185 0.2862 -1.7470 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6042 0.8279 -0.4971 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6716 1.3038 0.5420 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7696 2.8424 0.5996 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2581 0.8798 1.9008 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5689 -0.0551 0.0619 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3485 1.4544 -0.5803 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7076 2.9139 1.4772 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9977 0.4347 3.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4497 -0.2047 1.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4793 -0.4589 3.2912 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8521 2.4508 2.8778 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6562 -1.5872 0.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0667 -1.2823 -1.9259 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5142 0.3755 -1.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4721 0.3434 -2.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9785 0.9282 -3.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9916 -0.1599 -4.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0650 -2.8135 -3.4261 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5863 -1.2044 -4.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9763 -1.8332 -4.5492 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6578 -2.7450 -2.4266 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0785 -2.8187 -1.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3740 -2.6235 -0.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8690 -2.0713 2.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5435 -1.3740 2.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8398 -3.8376 1.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7002 0.4467 1.9473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7632 1.3351 -0.6857 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5131 -0.1157 2.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9821 1.9458 2.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2121 -2.3238 -2.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8989 -0.3399 -2.7453 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6293 -1.7977 -2.1003 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3545 0.9149 -1.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7301 -2.4590 0.3548 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3877 -1.9092 1.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9778 -1.8353 2.0685 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6579 1.5075 1.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8735 0.0611 2.7240 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8552 1.6792 2.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1846 -0.0595 2.2950 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7009 1.7885 -0.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4574 -1.7834 -0.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8914 -2.3609 -0.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1564 -1.8063 1.1076 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3982 -0.8909 -2.4131 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0154 0.8329 -2.2962 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5891 -0.6599 -1.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2374 0.9322 -2.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2796 1.6834 -0.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7557 3.1515 0.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5950 3.1846 -0.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9364 3.2366 1.2188 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2158 -0.2221 2.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3391 1.1363 1.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8388 1.4471 2.7288 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9154 -0.6605 -0.6614 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5034 1.3351 -1.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1155 2.1254 -0.0840 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5532 2.1374 -0.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0234 3.1578 2.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0795 2.9315 0.5480 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5222 3.6595 1.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 9 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 15 16 1 0 14 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 35 39 1 0 21 40 1 6 3 41 1 0 14 7 1 0 26 21 1 0 36 30 1 0 22 13 1 0 31 25 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 7 46 1 1 8 47 1 0 8 48 1 0 10 49 1 0 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 11 54 1 0 12 55 1 0 12 56 1 0 13 57 1 1 15 58 1 0 15 59 1 0 16 60 1 0 17 61 1 1 18 62 1 0 19 63 1 1 20 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 25 68 1 6 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 28 73 1 0 29 74 1 0 29 75 1 0 30 76 1 6 32 77 1 0 32 78 1 0 32 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 34 83 1 0 35 84 1 6 37 85 1 0 37 86 1 0 37 87 1 0 38 88 1 0 38 89 1 0 38 90 1 0 39 91 1 0 40 92 1 0 40 93 1 0 40 94 1 0 41 95 1 0 41 96 1 0 41 97 1 0 M END

Standard InCHIKey	JIXNEPDMGSNJOM-AUBQSUGRSA-N
Standard InCHI	InChI=1S/C35H56O6/c1-10-20(2)29(40)41-26-18-30(3,4)17-22-21-11-12-24-32(7)15-14-25(37)31(5,6)23(32)13-16-33(24,8)34(21,9)27(38)28(39)35(22,26)19-36/h10-11,22-28,36-39H,12-19H2,1-9H3/b20-10-/t22-,23-,24+,25-,26-,27-,28+,32-,33+,34-,35+/m0/s1
SMILES	C/C=C(C(=O)O[C@H]1CC(C)(C)C[C@@H]2[C@@]1(CO)[C@H](O)[C@H](O)[C@@]1(C2=CC[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)O)C)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	572.41	Volume:	615.966 ? Van der Waals volume.
Dense:	0.929	LogP:	4.497 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.042 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.261 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	28.0
TPSA:	107.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.2	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.352	Fsp³:	0.857
MCE-18:	112.462 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.627	Fluc inhibitor:	0.004 ? 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:	0.293	Promiscuous compounds:	0.281

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.491	MDCK Permeability:	-5.149
Pgp-inhibitor:	0.022	Pgp-substrate:	0.79
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):	0.034
20% Bioavailability (F20%):	0.957	30% Bioavailability (F30%):	0.715
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.182	MRP1:	0.651
Plasma Protein Binding (PPB):	92.372%	Volume Distribution (VD):	-0.056
Fu:	6.594% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.715	BCRP inhibitor:	0.415
BSEP inhibitor:	0.956

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.653	CYP2C19-substrate:	0.994
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.037	CYP3A4-substrate:	0.506
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.962
HLM stability:	0.882 ? 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):

7.014

Half-life (T1/2):

1.502

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.203
Human Hepatotoxicity (H-HT):	0.29	Drug-induced Liver Injury (DILI):	0.06
AMES Toxicity:	0.391	Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.817	Skin Sensitization:	0.686
Carcinogencity:	0.789	Eye Corrosion:	0.004
Eye Irritation:	0.407	Respiratory Toxicity:	0.768
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.783
Hematotoxicity:	0.239	Drug-induced Nephrotoxicity:	0.782
Genotoxicity:	0.381	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.107	Hek293 Cytotoxicity:	0.22
BCF:	1.511 ? 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:	4.061 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.735 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.998 ? 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
NPO33464	cyrilla racemiflora	Species	Cyrillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422131]
NPO40059	Camellia crapnelliana	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29064696]
NPO33464	cyrilla racemiflora	Species	Cyrillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	2
Activity	1

Activity Type	# Activity
Individual protein	1
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	2560.0	nM	PMID[29064696]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	8700.0	nM	DOI[10.1007/s00044-012-9988-y]
NPT21742	Cell line	L02	Homo sapiens	Activity	>	90.0	%	PMID[29064696]

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 NPC273668 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	19324
0.1-0.2	24022
0.2-0.3	5531
0.3-0.4	831
0.4-0.5	114
0.5-0.6	21
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC88349
0.7857	Intermediate Similarity	NPC475263
0.7778	Intermediate Similarity	NPC480921
0.7778	Intermediate Similarity	NPC480920
0.7703	Intermediate Similarity	NPC474190
0.6944	Remote Similarity	NPC480919
0.6842	Remote Similarity	NPC476132
0.6622	Remote Similarity	NPC294360
0.6447	Remote Similarity	NPC175006
0.6377	Remote Similarity	NPC480924
0.6286	Remote Similarity	NPC238992
0.6282	Remote Similarity	NPC473160
0.6145	Remote Similarity	NPC473586
0.6	Remote Similarity	NPC237344
0.5949	Remote Similarity	NPC283343
0.5595	Remote Similarity	NPC476195
0.5476	Remote Similarity	NPC603645
0.5432	Remote Similarity	NPC480923
0.5417	Remote Similarity	NPC474989
0.5405	Remote Similarity	NPC470588
0.5301	Remote Similarity	NPC258547
0.5229	Remote Similarity	NPC277212
0.5229	Remote Similarity	NPC30279
0.5229	Remote Similarity	NPC473918
0.5182	Remote Similarity	NPC71391
0.5135	Remote Similarity	NPC311078
0.5135	Remote Similarity	NPC101475
0.5125	Remote Similarity	NPC49776
0.5125	Remote Similarity	NPC63118
0.5125	Remote Similarity	NPC164349
0.5125	Remote Similarity	NPC474436
0.5067	Remote Similarity	NPC235341
0.5067	Remote Similarity	NPC253807
0.5067	Remote Similarity	NPC158662
0.5065	Remote Similarity	NPC246708

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC273668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7195
0.1-0.2	1895
0.2-0.3	56
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
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
0.5063	Remote Similarity	NPD7645	Phase 2

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