NPASS Compound

Natural Product: NPC546690

Natural Product ID	NPC546690
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1~{R},2~{S},4~{S},5'~{R},6~{R},7~{S},8~{R},9~{S},12~{S},13~{S},16~{S},18~{S})-5',7,9,13-tetramethyl-16-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-spiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-10-one
IUPAC Name	(1~{R},2~{S},4~{S},5'~{R},6~{R},7~{S},8~{R},9~{S},12~{S},13~{S},16~{S},18~{S})-5',7,9,13-tetramethyl-16-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-spiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-10-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic 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 94100 0 0 0 0 0 0 0 0999 V2000 -9.3777 1.1241 -1.7946 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0963 0.1751 -0.6436 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3496 0.9674 0.4119 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9039 1.0682 -0.0920 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2408 -0.2931 -0.0696 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2500 -1.2665 -0.0826 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1419 -0.9257 -1.1052 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3385 -0.4506 -1.1087 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3785 -1.3501 -0.7145 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0288 -1.1103 -1.3761 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1060 -0.9818 -0.2294 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7766 -0.3993 -0.4656 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0041 -1.1609 -1.4721 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2907 -1.7282 -1.0304 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0898 -0.9270 -0.0935 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3056 -0.2686 -0.6613 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1890 0.1691 0.4815 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1357 1.0460 -0.0731 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4351 0.5693 -0.0081 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9671 0.3412 -1.2473 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0159 -0.5735 -1.1951 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6761 -0.7418 -2.5253 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7958 -1.2039 -3.5043 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0353 -0.1770 -0.1531 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1391 -1.1072 0.8783 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7642 1.2232 0.3654 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5819 1.4043 1.4845 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3445 1.4520 0.7889 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0613 2.8130 0.5152 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4851 0.9005 1.5627 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0954 0.4900 1.8631 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3100 0.1798 0.6076 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2206 1.4332 -0.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0509 -0.3584 0.8854 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8118 0.3958 1.9171 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1878 -0.2151 2.0404 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6050 -0.6528 3.0805 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9510 -0.2151 0.7636 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2092 1.1988 0.3685 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1797 -1.0498 0.7738 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4239 -0.3585 1.2179 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1168 -1.2797 2.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1411 2.1744 -1.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7245 0.8721 -2.6640 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4286 1.0520 -2.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0452 -0.2385 -0.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3011 0.4356 1.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7249 2.0108 0.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8780 1.4580 -1.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4033 1.8054 0.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7640 -1.8053 -1.4091 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5497 -0.5495 -1.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6578 -2.4090 -0.8552 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7719 -1.9693 -2.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1376 -0.1678 -1.9477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9723 -2.0072 0.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8773 0.6504 -0.8428 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1861 -0.5634 -2.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6412 -2.0183 -1.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9212 -1.9180 -1.9501 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1047 -2.7731 -0.6389 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4593 -1.6120 0.7270 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8693 -1.0273 -1.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0817 0.5477 -1.3751 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6646 -0.7577 0.8783 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3546 -0.4403 0.4948 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5911 -1.5483 -0.8869 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5235 -1.4514 -2.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0884 0.2355 -2.8521 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6303 -2.1514 -3.3052 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0233 -0.1421 -0.6514 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7782 -0.7541 1.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0873 1.9898 -0.3702 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3815 2.3418 1.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1897 1.2615 1.8755 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8606 2.9550 -0.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5558 2.0158 1.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0914 0.7546 2.5074 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6101 1.2979 2.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0990 -0.4201 2.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0822 2.1379 -0.0067 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1872 1.2981 -1.2841 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3129 2.0048 0.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0598 -1.4076 1.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.4591 1.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2658 0.3477 2.8603 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5708 1.7310 1.2985 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3405 1.7634 0.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0043 1.3250 -0.3789 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9673 -1.9713 1.3529 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2623 0.6461 1.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3467 -1.7971 2.8590 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8212 -0.7349 2.8634 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6056 -2.0921 1.6498 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 1 6 7 1 0 5 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 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 17 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 32 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 6 38 40 1 0 40 41 1 0 41 42 1 0 7 2 1 0 40 9 1 0 41 5 1 0 38 11 1 0 34 12 1 0 32 15 1 0 28 19 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 1 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 7 51 1 0 7 52 1 0 9 53 1 1 10 54 1 0 10 55 1 0 11 56 1 1 12 57 1 6 13 58 1 0 13 59 1 0 14 60 1 0 14 61 1 0 15 62 1 1 16 63 1 0 16 64 1 0 17 65 1 1 19 66 1 1 21 67 1 1 22 68 1 0 22 69 1 0 23 70 1 0 24 71 1 6 25 72 1 0 26 73 1 6 27 74 1 0 28 75 1 1 29 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 34 84 1 1 35 85 1 0 35 86 1 0 39 87 1 0 39 88 1 0 39 89 1 0 40 90 1 1 41 91 1 1 42 92 1 0 42 93 1 0 42 94 1 0 M END

Standard InCHIKey	NVCUAFIUMZCPGV-KZMKVQJGSA-N
Standard InCHI	InChI=1S/C33H52O9/c1-16-7-10-33(39-15-16)17(2)26-23(42-33)12-22-20-6-5-18-11-19(40-30-29(38)28(37)27(36)24(14-34)41-30)8-9-31(18,3)21(20)13-25(35)32(22,26)4/h16-24,26-30,34,36-38H,5-15H2,1-4H3/t16-,17+,18+,19+,20-,21+,22+,23+,24+,26+,27+,28+,29-,30+,31+,32-,33-/m1/s1
SMILES	C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@H]6O[C@@H](CO)[C@H](O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC(=O)[C@]3(C)[C@H]1[C@@H]2C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	592.36	Volume:	595.904 ? Van der Waals volume.
Dense:	0.994	LogP:	2.859 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.249 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.31 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	37.0
TPSA:	134.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.365	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.847	Fsp³:	0.97
MCE-18:	172.385 ? 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:	0.778	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.155	Promiscuous compounds:	0.259

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.173	MDCK Permeability:	-5.08
Pgp-inhibitor:	0.039	Pgp-substrate:	0.19
PAMPA:	0.976 ? 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):	0.006
20% Bioavailability (F20%):	0.165	30% Bioavailability (F30%):	0.617
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.039
Plasma Protein Binding (PPB):	51.592%	Volume Distribution (VD):	-0.268
Fu:	52.808% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.959
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.972	CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.956 ? 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):

3.401

Half-life (T1/2):

1.941

ADMET: Toxicity

hERG Blockers:	0.067	hERG Blockers (10um):	0.545
Human Hepatotoxicity (H-HT):	0.612	Drug-induced Liver Injury (DILI):	0.973
AMES Toxicity:	0.568	Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.333	Skin Sensitization:	1.0
Carcinogencity:	0.283	Eye Corrosion:	0.0
Eye Irritation:	0.045	Respiratory Toxicity:	0.119
Drug-induced Neurotoxicity:	0.049	Ototoxicity:	0.948
Hematotoxicity:	0.203	Drug-induced Nephrotoxicity:	0.73
Genotoxicity:	0.025	RPMI-8226 Immunitoxicity:	0.197
A549 Cytotoxicity:	0.406	Hek293 Cytotoxicity:	0.787
BCF:	1.535 ? 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:	3.541 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.962 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.3 ? 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
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8976	Agave americana	Species	Asparagaceae	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

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

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 NPC546690 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	23432
0.1-0.2	22986
0.2-0.3	2921
0.3-0.4	312
0.4-0.5	124
0.5-0.6	43
0.6-0.7	25
0.7-0.8	1
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
0.8295	Intermediate Similarity	NPC92890
0.7907	Intermediate Similarity	NPC215408
0.7742	Intermediate Similarity	NPC475319
0.7449	Intermediate Similarity	NPC233433
0.7294	Intermediate Similarity	NPC325828
0.7283	Intermediate Similarity	NPC202898
0.7209	Intermediate Similarity	NPC234352
0.7093	Intermediate Similarity	NPC297348
0.7093	Intermediate Similarity	NPC249204
0.7093	Intermediate Similarity	NPC48339
0.7093	Intermediate Similarity	NPC141769
0.7093	Intermediate Similarity	NPC477547
0.6952	Remote Similarity	NPC220836
0.6889	Remote Similarity	NPC107188
0.6778	Remote Similarity	NPC206003
0.6778	Remote Similarity	NPC473610
0.6742	Remote Similarity	NPC477451
0.6739	Remote Similarity	NPC107962
0.6733	Remote Similarity	NPC108072
0.6703	Remote Similarity	NPC211354
0.6667	Remote Similarity	NPC94086
0.6667	Remote Similarity	NPC473817
0.65	Remote Similarity	NPC161035
0.65	Remote Similarity	NPC170438
0.6489	Remote Similarity	NPC6295
0.6477	Remote Similarity	NPC485594
0.6354	Remote Similarity	NPC160426
0.6333	Remote Similarity	NPC177834
0.6304	Remote Similarity	NPC250393
0.6289	Remote Similarity	NPC475351
0.6222	Remote Similarity	NPC181845
0.617	Remote Similarity	NPC19400
0.6078	Remote Similarity	NPC97700
0.6078	Remote Similarity	NPC184617
0.6078	Remote Similarity	NPC30856
0.604	Remote Similarity	NPC249553
0.604	Remote Similarity	NPC182900
0.598	Remote Similarity	NPC128572
0.5914	Remote Similarity	NPC294686
0.5889	Remote Similarity	NPC24960
0.5816	Remote Similarity	NPC125324
0.5688	Remote Similarity	NPC132080
0.5686	Remote Similarity	NPC475643
0.5625	Remote Similarity	NPC222731
0.5607	Remote Similarity	NPC475625
0.5556	Remote Similarity	NPC277715
0.5464	Remote Similarity	NPC474399
0.5463	Remote Similarity	NPC116756
0.5446	Remote Similarity	NPC195297
0.5437	Remote Similarity	NPC161738
0.5429	Remote Similarity	NPC471464
0.5429	Remote Similarity	NPC51172
0.5429	Remote Similarity	NPC49032
0.5424	Remote Similarity	NPC305771
0.5424	Remote Similarity	NPC94072
0.5424	Remote Similarity	NPC169816
0.5413	Remote Similarity	NPC232037
0.5405	Remote Similarity	NPC92297
0.5392	Remote Similarity	NPC113044
0.5392	Remote Similarity	NPC283829
0.5392	Remote Similarity	NPC14704
0.5392	Remote Similarity	NPC161676
0.5364	Remote Similarity	NPC470864
0.5347	Remote Similarity	NPC470432
0.5347	Remote Similarity	NPC230507
0.5347	Remote Similarity	NPC485595
0.5333	Remote Similarity	NPC477809
0.53	Remote Similarity	NPC264101
0.5288	Remote Similarity	NPC473601
0.5283	Remote Similarity	NPC300557
0.5269	Remote Similarity	NPC473774
0.5269	Remote Similarity	NPC481419
0.5269	Remote Similarity	NPC481417
0.5234	Remote Similarity	NPC480555
0.5234	Remote Similarity	NPC150372
0.5169	Remote Similarity	NPC15918
0.513	Remote Similarity	NPC470866
0.5094	Remote Similarity	NPC602423
0.5085	Remote Similarity	NPC273002
0.505	Remote Similarity	NPC54619

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC546690 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7211
0.1-0.2	1855
0.2-0.3	74
0.3-0.4	5
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
0.7-0.8	1
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
0.7294	Intermediate Similarity	NPD8171	Phase 2
0.6848	Remote Similarity	NPD8170	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